I have had to get creative with how to fund many of my projects that fall squarely in the “Other” category.

Since departing Upcycled Food Association in 2022, I have had the opportunity to work on a number of creative and artistic projects, ranging from poetry to film to sculpture. They have one thing in common: they were all very tough to fundraise for. Without nonprofit status, these projects had to leverage just about every fundraising method I know of to get the capital needed. Here’s a quick breakdown:

Begin Where You Are: The Colorado Poets Laureate Anthology: We created an anthology of Colorado’s poets laureate going back 100+ years to raise money to bring the poet laureate to more rural and low income communities. To accept the startup grant funding we needed, we worked with a professional fiscal sponsor organization, Colorado Nonprofit Development Center (CNDC), an organization whose whole business model is to enable small projects to access the benefits of nonprofit status without going through the lengthy process of gaining IRS 501c3 designation. CNDC is great, and they provided a high level of back office support to our organization, but working with a group of artists creating a book was totally new for them. Their typical sub-project is a small community based nonprofit with staff & ongoing operations, rather than a point-in-time creative project like a book publication.

Durango Poet Laureate Program: We created a local poet laureate program in Durango, Colorado, funded by the City of Durango’s Lodger’s Tax Arts and Culture Fund. A poet laureate program isn’t necessarily an organization, so we partnered with a nonprofit who acted as the fiscal sponsor to accept the grant from the city and dole out the money to the laureates. The Friends of the Durango Public Library is a 501c3 that exists to raise extra money for the Durango library. They were wonderful to work with, but they are not a professional fiscal sponsor organization like CNDC, so this work was outside of their wheelhouse and put a burden on their limited resources.

Durango Solar System: We created a to-scale model of the solar system along the Animas River Trail in Durango, including nine beautiful permanent sculptures at cosmically accurate locations and sizes. I curated about 20 local artists and builders who crafted the planets, pedestals, plaques, and more. To accept the grant awards which funded the project from the City of Durango and Durango Parks and Rec, my personal LLC accepted the contract and subcontracted out the dozens of artists. But there was a problem. The grant was on reimbursement, meaning I had to spend the money before the funders would pay me. I didn’t happen to have $50k laying around, so a local nonprofit loan fund fronted the money and waived the processing fees so I could pay the artists before they purchased their materials. This worked well for the project, but it required me to personally take on a large loan and pay the interest myself (worth it, but still).

Moving Line: An award-winning documentary film about the first ski-crossing of Colorado in 1978. We raised money through the film-specific crowd funding platform, Seed & Spark. This platform is top notch for any independent film maker. They vet the films they let into the platform to make sure only motivated and organized filmmakers can get started, and then provide lots of support to ensure they are successful in meeting their goal. But crowdfunding is not a sustainable solution for the average creative artistic project. It takes a huge network, tons of fundraising experience, and many hours. Very few people are casually browsing crowdfunding platforms, making donations to random projects. Almost all the money we raised was directly from our own network, meaning this isn’t necessarily an avenue that an artist without backers and fundraising strategy can rely on by themselves.

If there is one thing I have found to be true about working with artists, it is that they are not particularly skilled at business. It is as if to make room in their brains for the artistic passion that create the pieces of work that give us goosebumps, they have had to shed the left-brained, technical acumen of running a business with its boring technicalities of financial statements and operational processes.

I have found it blissfully symbiotic to work with artists in the role of curator and producer, because it allows me to lend my skills at funding and running businesses, and leaves the creative work to those with practical skills outside of sending emails (unlike myself).

What we need is a professional fiscal sponsorship organization specifically dedicated to artistic and creative projects. This organization would provide the high quality back office and administrative support of a CNDC, targeted at the wide range of creative projects that need to raise money outside of the 501c3 paradigm. This organization could provide financial literacy training, fundraising strategy consultation, and other technical assistance to help bridge the artistic-business gap.

Fractured Atlas is a artistic fiscal sponsor that has supported thousands of artistic creative projects, moving $4M per year. But as a Model C fiscal sponsor, they are basically a pre-approved grant recipient, rather than providing full blown back office, payroll, bookkeeping, and fundraising strategy. Without this additional support, artists will be limited in their efforts (and we will be limited in our goosebumps).

The beauty is that fiscal sponsor organizations have a built in revenue model. Most take 5-15% of money raised to support their internal operations, meaning they have aligned incentives with their sub-projects and don’t necessarily have to fundraise themselves.

If you took my projects above as an example, which collectively raised $145,000, $16,100 on average per project per year, you could reach 430,000 people and provide $710,000 in social value, while raising $14,500 for the Artist Fiscal Sponsor to provide technical support. CNDC has about 80 sub-projects, which I think could be achieved in five years by this hypothetical Artist Fiscal Sponsor, helping to raise $1.3 million and reaching 3.8 million people. Fractured Atlas has shown that this can be scaled, and with thoughtful technical assistance support I can see these numbers growing significantly.

Any takers?

We enjoyed low flows (8,000 cubic feet per second, CFS) and warm water (68 degrees Fahrenheit, twenty degrees higher than normal), which reminded us of the fragility of desert landscapes, offering a harbinger of climate changes to come. A flash flood worsened by last year’s North Rim fire ripped through Phantom Ranch, destroying infrastructure and tragically killing multiple people. We realized the vastness of the canyon only upon returning to cell signal to learn of the disaster, which occurred over 100 miles away as we relaxed on pristine desert beaches, totally oblivious to the destruction or weather upstream. The river swelled to over 30,000 CFS, but we would be off the river before it reached us.

I am not the first person to call rafting the Grand Canyon life-changing. And I hope I am not the last. I hope humans get to experience this magic for many generations into the future. After weeks surrounded by loved ones in a true wonder of the world, I am filled with awe. And hope.

Yesterday was filled with tearful voice memos sent to dozens of new and old friends I had the opportunity to connect with under the bright moon in a sacred canyon, and trying to wrap my head around returning to the real world after weeks of meditating through the repetitive motions of rowing, setting up camp, and watching the beauty of the canyon reflected through unfathomably ancient rocks.

So, I couldn’t bring myself to post a social enterprise idea yesterday. I wrote a love letter instead.

Love Letter to the Desert

Your quiet stillness, your impossible light, your frigid pitch of night, thank you for being made of water.

As leaves shake and shift the shape of their shadows on the sand below, I am a terrestrial wanderer, and I am dry. Thank god I am dry. Wandering through your deepest cavities, my soul feels like itself.

Terry Tempest Williams says, “Every trip to the desert is an encounter with the soul.” So when I say, “I want to lay on my back in the red sand amongst sage brush at night, looking past the stars to a blackness only replicated by your shadows,” what I mean is: “I wish to know my own deepest nature.”

And when I say, “In the fall, when your cottonwoods along the creek are white and yellow, and the violent heat of summer has given way to a cool scent of mildew, and for once I feel hopeful of living through another winter, and another,” what I mean is, “I love myself.”

I assume my apologies are folly in the light of your intelligent design, so I hope we do not sound trite when we say grace to the last peoples who configured their lives to be congruent with your turquoise and gold contours. My ancestors did not know that every inch of stone is ten thousand years of sediment within a forgotten ocean. Attempting to make their world bigger, they drove their plows over your wise soil, which you concocted to hold the size of the world you needed: small. When there was not enough water to make things big, you created a world of small.

There need not be a grand river—though there is—to flood the world into a mossy chasm. All the world need not be a image of the rain forest reflecting in the sea. Some of the Mother will always be ocotillo growing out of sand, which blowing through your messenger, the wind, burrows into my hair like a prickly seed carried by a big horn sheep across the land for new life. Life that will avoid you in favor of superfluous water, not knowing that a single spindle of the barrel cactus contains a cloud.

And when the rains do come, you draw the eye upward to a wave whose momentum fills the empty canyon, illuminating—finally—the immensity of the space between your invisible red edges, only be heard by the bat or at best seen at night against the sky. Trying to account for your edges, we see your mate, the sky. The only place big enough to contain you, the cosmos was built in every direction forever to make its yolk.

The mate of the desert is the sky.

Thank you for being small. And, thank you for being big. Thank you for making me a wanderer, hands clasped to the open surge of baron heat, the holy blackness of a crow soaring too long overhead. Alone. The soul of the desert is alone.

I am not gullible to say that I am the only human to ever look into this particular birds nest cavity on the sloping face of some Chinle sandstone. Some vishnu schist. Some mauve limestone. Some human articular flesh. Your mass moves so quickly through the canyon. And so slow through the eons. We have all come and gone to chalk colored bones a thousand times by the time your body took its dancing shape across the continent. By the time we know ourselves, the wind has shaved you into something else entirely.

Thank you for being slow. And thank you for being so fast. Fast like together, hands held on a slippery nude granite stone. Fast like wind, carrying us toward each other, a huddled mass praying, crying, missing. The message of the desert is together.

The messenger of the desert is the wind.

The Wind.

when I was young I hated the wind

; fussing with my plans—perfectly curated,

primmed into a sort of logic model, and now,

wrinkled, wrecked, by that old westerly.

when I die, by the time I die, I shall

loosen my grip, embrace the wind back

through its grandmother arms,

and love the wind, as I know it does me,

I thought.

In my middle age, my frustration had not subsided,

for the wind would swirl around my thinning head

of hair, revealing my receding youth, my plans

all the more rushed now, a growing list of topical

interests, a flow of ideas as constant as,

you guessed it, the atmospheric force transport

-ing layers of snow to the paths of my friends, sometimes

swallowing them up, stealing their last breath, or rather

, expediting.

as old age comes, and it will, iIstill look

forward to the moment, perhaps the only one,

when I give up. when I see the wind

for what it was: potential breaths of a bear, butterfly,

tree or me, moving to where there is more space

—who could blame it—a body standing in the way.

In a meeting with a peer of Small Capital, co-founder Jamie Finney and I were a bit stunned when the person across the table remarked that we were both wearing flat-brimmed, snapback ball caps. Jamie and I both live in Durango, which has been called the worst-dressed town in America, and where, yes, a lot of people wear hats.

There is a tongue in cheek adage here in the mountain communities of the American west that says you can tell how much time someone spends outdoors by how many helmets they have (road biking, gravel biking, mountain biking, all requiring different helmet styles to avoid looking like a dork, not to mention climbing, rafting, and skiing requiring three more). The measure of a civilized person in a place like Durango can be approximated by their hat collection. Whether you’re wearing a hat to conceal a receding hairline like mine, or to represent a sports team, you can tell a lot about a person by how they keep the sun out of their eyes.

There are some super touristy places in town that sell Durango hats that moms visiting from Oklahoma will wear, but not actually, you know, fashionable ones that would be worn non-ironically in our beloved town. This is despite the fact that Gen Z’s homogenization of our collective fashion sense has at worst earned us a last place tie.

I was playing volleyball with City of Durango business development manager and bestie Tommy Crosby the other night and he told me that he recently doled out the latest round of Durango Lodgers Tax Arts and Culture Fund grants. The current round has $80,000 to give away. Durango voters approved the tax in April 2021, raising the lodgers tax from 2 percent to 5.25 percent, with 14 percent of it devoted to arts and cultural.

Tourists pay hotels, hotels pay a tiny additional tax, and we all get public art. Pretty good deal. Four projects I have worked on have been awarded about $75k of this funding, and the program as a whole has put $1.9 million into 145 projects between 2022 and 2025, lifting Durango’s arts spending from about $3 per capita to about $37. You can feel it walking along streets increasingly adorned with murals, sculptures, and creative programs made by local artists.

I’d like to contribute to this kitty of money available to local creatives. In rough estimation, I could make $10 per hat gross, donate the fixed costs of my time and tech, and probably sell 500 hats at local farmers markets and online, generating $5,000 to give away to my creative neighbors.

Will I carry out this silly idea? In this case, actually yes, probably. That’s just how my brain works. When I think of something I want, even something as simple as a hat, I inadvertantly start to think about how to turn it into a social enterprise. You can’t take me anywhere…

Just months before, Aaron and I had stood on the top of Quandary Peak, a 14,000 foot peak outside of Breckenridge, Colorado. We began our climb in the dark of the morning, and skied down perfect slopes of light powder under the cold winter sky. Nicknamed “The Best Skier on the Mountain,” Aaron was generous to let me tag along. He could have been, and often was, mysteriously missing from our community climbing gym sessions on weekday mornings. We’d later find out he had buzzed over to Aspen or Summit County for an impromptu ski tour, where his tie-dye shirt and shaggy long brown hair—homages to his upbringing by a father who attended hundreds of Grateful Dead shows—would flap in the freezing wind of the high country.

And now, he was… gone? The finality was as confusing and repulsive as that which arrives with the death of any thirty-year-old. The mysterious circumstances of his passing left his family and community with a grief I have come to learn is unique to avalanche fatalities.

In the backcountry skiing community, fear of avalanches is potent and ubiquitous. We design our lives around avoiding avalanches, spending our weekends on slopes chosen for lower slide risk, practicing rescues, and following the Colorado Avalanche Information Center’s forecast more closely than the local news. Our backpacks contain airbags that expand to create a theoretical asphyxia-avoiding air pocket, and are filled with the mandatory gear that, if forgotten at home upon arriving at the trailhead, is cause for cancelling the day’s mission and going home. Beacon-shovel-probe is like a single word, whose definition is I hope we make it home.

Avalanches have a god-like presence in mountain towns across the west. They control our lives, a source of ambient background fear amidst the pure joy of skiing; a reminder of life’s fragility, avalanches give and take away.

The next five years of my life would come to be dense with the deaths of more friends, including more in avalanches. I have noticed a sibling-like fellowship that is shared among those who have lost loved ones in this devastating way. Our communion is made of a mixture of anger for the injustice of loss, and solace that this loss occurred while participating in the activity that makes life so sweet.

This fellowship is callused, bereaved, and tender. When someone dies in an avalanche, the comment section is cruel, filled with They should have’s and What an idiot’s. The machismo of outdoor culture puts unnecessary pressure on the stoic masculine archetype, preventing the vulnerable flow of emotional energy necessary for holistic mourning. We are a community that needs help, and often does not know how to seek it out or accept it. We pore over the reports from the sheriff and search and rescue (SAR) organizations when an accident is filed, looking for some kind of explanation, seemingly simple yet frustratingly elusive: Where is he? Why is she gone?

There are a growing number of wonderful organizations, such as Survivors of Outdoor Adventures and Recovery (SOAR), which aim to provide critical support to the communities of those closest to friends, family, and coworkers who are lost or injured in the backcountry.

These organizations deserve our support as outdoor recreationalists, as oftentimes those most affected are the SAR teams who risk, and sometimes lose, their lives to provide us a comfortable, often invisible, backstop while enjoying the backcountry.

I see an opportunity to complement these organizations’ work by creating a forum that connects the friends and families of the victims of avalanche fatalities, allowing grieving survivors to connect with support wherever they might be, and fulfill the incessant need to learn about the mountains, culture, and science that led to the deaths of their beloved.

When Aaron passed, his parents hardly knew what backcountry skiing was. They were surprised to know that he was a skilled skier, and shocked to learn that he had been skiing out of bounds, on something so steep. I cannot imagine the terrifying loss of a child being compounded by such utter confusion.

I wish Aaron’s parents had a place to go where they could connect with other parents whose children had died in avalanches. I wish they could easily read about other accidents to find a sense of not being so alone and singled out. I wish they could ask other grieving survivors how they are making it through. I wish they could tell their sacred story, their avalanche story, which connects them to this fellowship across borders and generations.

I envision an online forum designed to connect survivors, share stories, celebrate life, and facilitate mourning. I expect this forum could be vibe-coded and promoted for $10,000 or so, and that it could reach 50% of the families of the roughly 27 people killed in avalanches in the United States each winter, at least 2,700 people supported in the next decade.

Until, and long after this forum exists, I am sending a heartfelt prayer for peace for every one of these survivors. I love you.

As we perused these lovely cities, it occurred to us that the built environment, centuries older than any built environment in America other than the remains of Ancestral Puebloan structures, felt perfectly congruent with our experience, always a step ahead in anticipating our needs. Just at the moment that someone needed a bathroom, one would appear beside a public park. When mom needed a shady, secluded area to feed the baby, such a bench would manifest just in time. And when we all needed to take a load off after logging forty or fifty thousand steps after a long day of touristing, one of these little green roofed kiosk bars would emerge among the cobbled limestone roads.

Quiosques, or kiosks, seemed to be in every park, and to be a common happy hour spot where friends would gather for a small Super Bock beer or a glass of port and perhaps the classic Portugese pastry pastel de nata or some sardines and bread. Groups of college-aged friends laughing, white-haired elders listening to live music, and yes, young families with babies, all made pit stops at these quiosques before the evening fell and the tables and chairs were stacked by the proprietor and locked together outside of the tiny kiosk structure.

I’m not an urban planner or expert on the built environment, so I can’t comment on the actual economics or social implications of such micro enterprises on public spaces. But I can say that the quiosques made us feel particularly taken care of by these cities on the other side of the world.

I wonder whether kiosks like these could make a home in America. I picture all the perfect places for them in the many Denver parks where I grew up. I can’t say I feel confident they would take hold. Not because people in Denver don’t adore an outdoor place to drink a beer. They specifically, infamously do. I doubt they would be allowed, let alone successful, in the US because of our complicated and confused understanding of public and private property.

Many Americans despise public land in a conservative pursuit of efficient land use, efficiency that can only be guaranteed through the magic of privatization. Weeks ago, one of my favorite places in the world, Bears Ears and Grand Staircase-Escalante, were cut by a combined three million acres, more than ninety percent between them, representing the largest rollback of public land protection in American history.

Yet simultaneously we are totally reliant on and adore our public lands. Eighty seven percent of western voters in 2024 visited national public lands. I have seen Trump flags flying high over the side-by-side buggies buzzing through Bears Ears. (Our utter reliance on public spaces to retain and irrigate our waning water supply in the west notwithstanding.)

I can visualize a progressive liberal in Denver protesting a quiosque, Don’t tread on our public parks! You can’t privatize that corner of, say, Washington Park! That would be an abomination, a defilement of our beloved greenspaces in exchange for personal gain.

But I think this makes an honest mistake that we are trained to make of business in an an economic system made of enterprises that win at the expense of low income people and the environment. If that is all we know, then yes, a quiosque in Washington Park is a scary, unjust prospect.

But if we can start to believe in business for good, if we can imagine a world where the quiosque is there not as a selfish money-grubbing exploitative business, but as a service for a tired new mom who needs a shady place to enjoy the early evening outside, then we start to build a community in alignment with my favorite definition of community, Adam Brock’s: a group of people who need each other. Another favorite quote about community speaks to the exchange of resources, value, and culture inherent in social enterprise, and comes from a my mentor, Beverly Grant: “We don’t build community. We weave.”

I expect that a single American quiosque could be constructed for about $250,000, and provide, as an example, 10% of Washington Park’s 1M annual visitors with a comfortable place to weave their community (100,000 visitors per year. On par with a busy coffee shop.)

I’m not a big festival person, but Bluegrass is different. There is a special energy generated each summer solstice in this San Juan Mountains box canyon, where a large waterfall under massive peaks serves as the spectacular backdrop to a baseball field filled with kids running feral with water guns, massive corndogs, swimmers in the chilly San Miguel River, and twelve thousand Festivarians dancing to more-than-just-bluegrass music for a four-day weekend. I have heard professional musicians say, “We measure the passage of time via this festival.”

It is a 50+ year-old music festival steeped in tradition, which makes it a fun place to bring a newcomer, who will laugh at the variety of ingrained social norms taken for granted by the festival’s many long-time religious attendees.

It will be almost impossible to explain this, but imagine hundreds of camp chairs arranged in a long row for people to sleep in all night so they can be first in line to get a number, which entitles an early place in line for the daily ceremony of tarp running, where a stampede of blue tarp-carrying lunatics make a mad dash from the entrance of festival to stake their tarp in a prime spot near the stage. Despite this competition, where you will see hundreds of people of all ages in an all out sprint, tarp tightly under arm, anyone will be happy to host a stranger on their hard-won settled land.

The list of these quirks goes on. Sam Bush has played every festival but the very first one in 1974, and is considered the mayor of Telluride for the weekend. Every year, Chris Thile holds the opening Thursday mornings show, a festival convocation. Many artists have found their start here through the Troubadour competition, which puts young musicians on the main stage (the Chicks, then the Dixie Chicks, won the band contest in 1990). The same stage which has hosted headliners ranging from David Byrne to Johnny Cash, Elvis Costello and Robert Plant, to Brandi Carlile and Tenacious D.

Ever since creating Moving Line, I tend to think in terms of, “That would make a great documentary!” Which in my mind manifests as, “Is this story compelling enough that I would be able to raise the funds to give it justice?” In this case, I think a talented but relatively novice filmmaker like my brother Cameron could pull it off with half a million dollars, creating a long overdue film for generations of Festivarians. Fifty-three years at roughly twelve thousand people a summer puts that audience at well over 100,000, even after you account for how many of us come back every single year.

• Kyle Richardson ran up and down Longs Peak, a Colorado peak that online forums will recommend hikers take 12-14 hours to climb, in under two (1:55:40, in 2020).

• Kelly Halpin completed the 97-mile Wind River High Route in about 2.5 days, a technical route with over 30,000 feet of climbing, roughly two thirds of it off trail, that takes most parties a week or more.

• My friend and Durango local Kyle Curtin ran the 171-mile Tahoe Rim Trail in just over 41 hours, unsupported, a loop most people take 10 to 15 days to hike.

There is a well established organization and online community for FKTs, Fastest Known Time, which manages and verifies the user-submitted database of FKTs, now more than 3,000 routes and 7,000 records. The organization is well worth a follow online. (I have a few FKTs myself, which yes, does call into question the legitimacy of the organization…)

But the current forum has a gap. Their guidelines list skiing right alongside climbing and biking as an acceptable mode on a multi-sport route, yet every route still has to “primarily involve running or hiking.” So a route that is mostly skiing cannot make the database.

Right now is the perfect time to change that. We just watched Skimo (ski mountaineering) make its Olympic debut at Milan Cortina, where Marianne Fatton and Oriol Cardona Coll became the sport’s first champions, and more skiers and regular people than ever are paying attention to ski racing, not just downhill (which has been home to celebrities like Lindsey Vonn and Mikaela Shiffrin for a years) but also uphill and across the land.

One example is the popularity of The Grand Traverse, a 40-mile backcountry ski race from Crested Butte, Colorado, to Aspen, run in two-person teams that start at midnight because that is when the avalanche hazard is lowest. (Humble brag: Emily Olsen, an incredible social entrepreneur in her own right, and I placed third in the co-ed division in 2021.)

I am biased, because a ski FKT of sorts was the subject of the film my brother and I made about the first people to ski the length of Colorado in 1978. Moving Line captures the story of three friends from Boulder as they skied from Durango to Wyoming along the Continental Divide, mapping the basis for the Colorado Trail. In 2024, Kyle Curtin set the overall FKT on the 490-mile CT, running it supported in 6 days and 15 hours and becoming the first person to cross it in under a week.

I think the FKT website should start to allow submissions from skiers so we can lean into this historic opportunity to grow a great sport. If they won’t do it, we will build it ourselves! I’m sure someone could vibe code a website for a few thousand dollars. With a few thousand more for a marketing campaign to raise awareness of the site, user submissions would help the platform reach escape velocity. Eleven million Americans went skiing last season, and backcountry ski touring is the fastest-growing segment in the sport. Within ten years, I predict a well executed initiative could reach 1% of the ~4M backcountry skiers & snowboarders in the US, 40,000 people.

Any takers?

But what story do we tell? Before landing on the one that thankfully made it’s way into the film, we perseverated on numerous story concepts that we thought would help illuminate the nontrivial, human experience we knew was hiding in the margins of the historical photographs and interviews that made up the bulk of our documentary footage.

“I know! We’ll tell the story of how one couldn’t ski across the mountains of Colorado in a single six-week push, scarcely touching dry earth, due to exacerbating drought and shrinking snowpack!” This story felt like a direct infringement on the intellectual property of experts like Protect Our Winters. In other words, it had already been told.

“What if the story is about the evolution of the ski industry, comparing our three amateurs’ ramshackle gear to the ubiquitous, high-tech ski gear of today as an allegory for the transformation of a sport and for mountain towns everywhere within a single generation?” This story ended up failing the storytelling test, which I tell founders should be the story they are telling with every pitch deck, answering, “Why This? Why Now? Why Us?”

After months of rumination and a glorious moment of clarity, we ended up telling a beautiful story about how the skiers saw their adventure as less of a skiing expedition than a journey of self expression ripe with landscape-art. But along the way, we learned about another would-be story: The story of the Colorado Trail.

In 1978, the famous 486 mile through-hike had not been completed, but its construction had been in the works for many years. Our skiers received funding from The Colorado Trail Foundation, who needed winter adventurers to scout remote parts of the Colorado wilderness that were on the short list for inclusion in the Colorado Trail, which is today one of the most popular point to point long distance hikes in the country. When the CT finally opened officially in 1987, it bore an uncanny resemblance thus to the route of our 1978 skiers.

As our skiers were sliding across the continental divide those six weeks in 1978, a woman born to German immigrant parents was years into what would become the decades-long process of coordinating hundreds of volunteers, lobbying politicians, coercing landowners, and shoveling dirt that was necessary to create a continuous trail through the mountains, from Denver to Durango, now visited by about 500 people per year.

Gudy Gaskill was an artist, mother, mountain lover, mover and shaker. Her tall stature was effective at commanding the forestry and trail-building volunteers who scratched the CT into existence one mile at a time. Her genius was in her ability to use her network and negotiation skills to advance a goal that conceded little to no economic motivation in an era when Colorado’s outdoor recreation industry was still nascent.

We were lucky enough to film interviews with Gudy’s adult children, as well as the seventeen-year Colorado Trail Foundation executive Director Bill Manning, whose wealth of knowledge and stories are treasures in light of his ongoing cancer diagnosis. These pioneers were all drawn to speak to the profound impact that the CT has had on thousands of lives since its inauguration. The CT is a place where people have fallen in love, and tragically, passed away. Everyone who makes the hike from end to end is changed, usually in a way that enhances their reverence for mountains and public lands.

This is a story that needs to be told. It’s a less niche story than Moving Line, so I think with $250,000 an independent film outfit could create a film that would reach about 100,000 viewers a year, ten times that of Moving Line, resulting in a $500,000 and 2x social return on investment. Bonus points if the film is used to raise money for The Colorado Trail Foundation.

Any takers? You can have the footage my brother Cam and I shot but never used!

This line of thinking began for me when working with nonprofit clients, where I noticed that not only is there is huge disparity between nonprofits and other businesses in their knowledge and use of AI, there is also a huge gap in the potential to create value.

You have probably heard that many corporations are having a hard time realizing value from AI implementation, which to me makes total sense. For a large business with thousands of data sources, tens of thousands of employees spread across dozens of countries and divisions, it sounds like an uphill battle to implement AI to support business operations, an ambition that relies on structured data that is expensive for LLMs to process.

Nonprofits and small businesses, however, are not only less complex (in general), but their work is naturally more congruent with gaining business value from AI. What they need help with is aligned with what AI is actually good at.

Anyone who is using AI to write copy and generate corny event posters is using AI for what it is distinctly bad at. AI writing sounds terrible, and those posters make me want to not attend the birthday party.

This is an education problem. When I show a client how we can fairly easily use an AI agent to combine multiple sources of data to, say, create a dashboard to track their financials and KPIs in one place, their mind is blown. They thought all AI could do was write bad blog posts.

If anyone is going to be really good at using AI to make their operations more efficient, I think it should be nonprofits and small businesses. When I tell my progressive friends that I’m working in AI they sometimes balk. That’s honestly fair. But even the most staunchly opposed to data centers will soften when I explain that I’m using AI to help nonprofits automate manual tasks that help them spend more time in their communities and create more impact; or helping solar companies install more solar panels to reduce carbon emissions (yes, net carbon emissions).

Assume for a moment that you agree with me and that as a society we’d want to help these types of businesses do better through AI. How could we achieve that? A good place to start would be to ask where these organizations exist.

My answer is that they exist locally. Right in your town or neighborhood, there are businesses you patronize or nonprofits you rely on that could be benefitting from AI. So all we need is a bunch of consultants going around locally and helping these organizations use AI, right? That’s a start, but as long as our beloved local businesses are relying on cloud-based AI through companies like OpenAI, Anthropic, and Google, they will be pawns in an exploitative game, and hamstrung from achieving what they want without paying more and more for usage.

What if we made AI a local utility that was cooperatively governed by ourselves, like our electric utility coop or water treatment plant? In Southwest Colorado, our local electric cooperative recently ended their 50-year contract with their energy provider to be able to purchase more renewable power.

What if we had the opportunity to create our own data centers, instead of being encroached on by outside developers who are oblivious to our values? I’m not the first to propose AI as a public good or even local utility. What is new here is proposing this as a solution to help grow social enterprises (yes, small business is social enterprise).

Here in Durango, Colorado, hundreds of miles from the nearest interstate, we have already built an autonomous little economy that has a miniature version of just about anything you need We have a VC fund and some tech companies and carpenters and a yarn store. The next generation of this self determined, autonomous economy in the middle of the desert will look like locally created, locally managed AI, by and for the benefit of local businesses and residents.

Durango and other towns will be incentivized to maintain effective local compute to attract businesses, assist startups, and support businesses to compete with regional and national competitors. We lose the economy of scale offered by huge tech companies but we gain self-determined, more sustainable AI that is tailored to local values.

Building a local data center sounds astronomically expensive to me. My small amount of research found that an LLM could be set up in on a local utility scale for a few hundred business for as little as $150,000 in startup costs and hardware and $200,000 in annual maintenance. To serve all of the roughly 3,200 local businesses in a town like Durango at these costs, call it $2.4M in startup costs and $4.8M in annual maintenance. This means to break even, each business would only need to generate $2,616 in additional net margin, which for the average business size in Durango is less than a quarter percent net margin. (Comment if you want to see the math in more detail.)

So there is a reasonably conservative, economic rationale for truly local AI (you probably already knew that). Combine that with the self determination for small businesses employing your neighbors, and there are considerable social returns here.

The social returns of the Durango Solar System are ostensibly to educate the public, especially kids, about outer space, getting them to think about their place in the universe, and, you know, become nicer people. The metric for measuring success against this outcome was simple: how many people will interact with solar system. We used a number estimated by Durango Parks and Rec for the number of people annually who travel along the Animas River Trail, a beautiful pedestrian thoroughfare used by tourists and commuters to get around town in Durango, Colorado: 60,000.

I like using this metric to measure success because it relies on an assertion that there is something beneficial to society about personal, individual experience. Whether you’re looking at an immaculately crafted metal orb resembling the planet Saturn, or a mural on the side of a building while you wait at a stoplight, your experience is happening at exactly one place in the entire universe: you’re own brain. And I’m supposed to believe that somehow makes my life better?! I’ll take it!

I recently found this video about the quietest room in the world, which drowns so much ambient sound you can hear your blood moving through your head. I’m now dying to go there. It reminded me of another claustrophobia-inducing venue high on my list: The Tank, a large steel cylinder in Rangley, Colorado that has become famous as a musical venue and recording studio. Both of these projects got me thinking about the physical spaces in which we put our bodies, and the magic these rooms contain to give so many people such profound experiences.

This is how I came up with the idea for the spherical mirror, which I am 95% sure doesn’t exist yet (though I’d love to be proven wrong). Imagine: You step through a trap door and close it behind you. The room where you’re now standing is a perfectly spherical concave mirror, maybe 10 feet across. Like The Bean in Chicago, but the mirror is facing inward and you’re standing on the inside. What would you see? What wouldn’t you see?

Any concave mirror has a focal point some distance from the mirror surface, beyond which makes everything look upside down. As you move past the focal point, things look big. A spherical concave mirror, however, would have a “focal plane” or more accurately, a “focal sphere”, rather than a focal point, since the mirror has no borders; one focal point next to the previous, again and again until there is a new illusory sphere inside of the mirror sphere. This raises some questions I don’t know the answer to. Do you? Is any of what I’m saying accurate? Let’s find out!

What would you see? An “infinite hallway” like a normal dual opposing mirror, or would the image be obscured by the focal sphere? Depending on the material used, inside the sphere would be dark. What would it look like to turn on a flashlight? A laser pointer? (Unless the light was directed orthogonally to the mirror surface, it seems like it would reflect forever until the entire volume was filled with lasers…).

Someone out there could easily do the math and answer these questions; I hope you do. But even if we know the technical answer, there is value to be realized in giving people the experience. I’m about to spend two weeks rafting down the Grand Canyon. I know I will be a different person on the other side. The Spherical Mirror, The Tank, the world’s quietest room are all our humble attempts at mimicking the power of places like the Grand Canyon. They are locations that provide lucky humans with weird awe, the variety of experience that makes us envision the heavens laughing at us, shining a light into the corners of our expectations, reminding us how lovely and confusing the world can be.

I am not particularly good at pricing public art pieces out yet; I originally budgeted the Durango Solar System at under $25k, and it ended up costing more than $50k. Let’s estimate it would cost ten times the cost of the Durango Solar System; half a million dollars. Assuming the cavity can accommodate one person at a time, and each person got to be inside for five minutes, the maximum number of people impacted would be just under 25,000 per year. The total social returns would be increased if the Spherical Mirror were to be used for research, education, or as a way to raise money for another organization.

Any takers?

Founders have now seen many times over what a high-stakes, polished pitch looks and sounds like, and have heard some successful people poke holes in their infallible ideas; a light form of realtime due diligence. (I bet there are some founders out there whose first exposure to raising capital was this show. Anyone?)

The general public has learned a little bit about what investing looks like, and many have probably developed a sense of what they would and wouldn’t invest in (if only they owned a sports team or fashion brand).

What if we created a similarly flashy, highly-produced show where the pitchers are social enterprises and the investors are foundations, donor advised funds, and impact investors?

There are so many worthy nonprofits and social enterprises out there. “Shark Tank for Social Enterprise” would help raise awareness about important organizations and raise money to help them succeed.

A show like this could also do wonders in dismantling the stereotype that your business is EITHER smart/prime-time/profitable, OR naive/cute/impactful. In other words, I think it could help to make impact investing more mainstream, just like Shark Tank made venture capital more mainstream. (If you balk at my claim that Shark Tank has made venture capital more mainstream, keep in mind that almost half of Americans, ~124M people, do not own any investments. And Shark Tank’s audience peaked at over 9M people per episode.)

I’m not suggesting that it would increase the number of dollars donated or invested in impact. US impact investments in 2024 were roughly $142B, and US nonprofit donations total more than $500B per year. So far in 2026, for profit startups have raised over $400B. But the increased mainstreaming of impact investing & philanthropy could bring good outcomes to society and social entrepreneurs themselves.

I think one of the most underrated skills is that of giving and receiving feedback. In the last 15 years, I have hired/onboarded about 100 staff ad board members into my organizations. I can guarantee 100% of them have heard me say, probably too much, Feedback is a gift (which I first heard from my college leadership professor, David Meens). We collectively grow as a society when we develop the skills of feedback (”Here’s how your idea could be improved…”), diligence (”Here’s why I would not invest in this…”), and scrupulousness (”Here’s why this business is not as holy as it appears…”).

When a good founder is interviewed backstage after getting rejected by the sharks, they don’t complain. Effective founders stick to their guns, but graciously accept the feedback for what it is: one more flawed but perfectly useful datapoint in their journey to find product market fit.

I think social entrepreneurs could take notes here. I often hear nonprofit leaders grumble with frustration or even anger when they get turned down by a funder. My head usually goes to, “Well, how good of a case did you make to the funder? Did you custom-write the application in the funder’s own language or did you use ChatGPT? Did you use evidence to show that you will efficiently convert their capital into the social returns they care about at a rate faster than other organizations?”

It hurts, I know. I estimate that I have been declined for funding over 1,000 times. But I try my damndest to respond to declines with thank you rather than f@$% you. The scientific method tells us that evidence is evidence and evidence is useful. Every decline is evidence: either We need to improve how we are asking for money, or simply, That is not the right funder for us.

The real Shark Tank has pledged over $220 million on-screen across its 17 seasons (though roughly half of pledged deals actually close after diligence). With $1 million in investment capital to get the show off the ground and polish it to resemble the real deal (though probably without Mark Cuban), I think a show like this could realistically achieve 1% of that lifetime capital allocation, about $2.2 million, in its first three years.

Foundations and impact investors would love it, too. I just assume they would enjoy being on TV.

Any takers?

As the share of donations that come from fewer, richer donors increases, it is increasingly important for nonprofits to understand how to run effective individual giving strategies, where lots of regular people give small but heartfelt amounts that add up to meaningful sums in aggregate.

Most of my clients revenue was coming from grants from institutional foundations. The client had good, years-old, working relationships with these foundations. In theory, the client’s institutional funders are periodically looking at the client’s financial statements, where they would see a relatively small number in the Individual Donations line. The foundations see this number, but do not think, “That individual donations revenue number could probably be significantly increased with an improved strategy.”

This is confusing, in light of the pervading intuition we nonprofit leaders tend to have: The feeling that our institutional funders do not really want to fund us; they don’t enjoy funding us; they wish we would go away, stop bothering them, and find the money elsewhere.

When filling out a grant application, nonprofits are often asked, “How are you going to support yourself after our grant is gone?” The leading question suggests it is not an acceptable answer to say, We will just keep receiving more grants from you, dear foundation, forever. The answer the foundation is looking for sounds more like, “The rest of our community will support us into the future, and you’ll never hear from us again.” I wish that instead of taking this response at face value, foundations actually invested in the sustainability that they want to see (how else should a nonprofit obtain said sustainability?).

To be fair, many foundations do fund technical assistance, capacity building, etc. But these dollars are typically targeted at general organizational strategy, evaluation, board development, conferences, and other helpful tools that will only indirectly help the grantee raise more money, and become less reliant on the foundation.

Instead of, “How will you sustain yourself when we’re gone?” foundations should be saying, “We’re making this grant because organizations like yours are the only way for us to realize our mission. We have an interest in your survival, because without you, dear operating nonprofit, **we are unable to accomplish anything of value—let alone our own goals—**so we’re going to add a small amount of funding to your grant so you can build some systems that will help you raise money without us.”

My nonprofit client spent about $11,000 to hire me. I conservatively estimated that the strategy will triple their individual fundraising in the first three years, from $40,000 to $120,000 per year. Assuming this growth occurs linearly, the organization will have raised an additional $120,000 by end of Year 3. This represents a 10.9X return their $11,000 investment. Pretty good deal.

But if funded by a foundation, who cares about social return on investment, it’s an even better deal. The net increased social impact provided by the organization as a result of the tripling of annual individual donations is almost certainly greater than the social impact provided by an $11,000 donation, especially in the medium and long term. Simply because $120k > $11k.

Importantly, I think this strategy would work best with organizations of about the size of my client: ~$1.5M in annual revenue, and less than $100k in annual individual donations. It’s unlikely that an $11,000 engagement would be able to triple the annual individual donations of an organization already raising millions. But that’s ok. The vast majority of nonprofits are small, and this is exactly where the types of simple, low-input recommendations I made to my client will have a big impact.

Scaling these assumptions linearly, if a foundation invested $1M in this strategy into a portfolio of similar organizations, they could expect to realize almost $11M in new, decentralized individual donations going towards the organizations the foundation needs to accomplish its mission. This ~11X ROI represents about 154% of what I call internal rate of impact (IRI) which is where you apply the math of internal rate of return (IRR, a common metric for measuring the success of a financial investment) to an investment in a social enterprise. (I’ll talk more about this concept in a future article.) This is an incredible investment, even without including non-financial values of the increased social returns created by the additional revenue. For context, a 30% IRR is enough to make any capitalist shiver with excitement.

Any takers?

No, I’m not a pedal-power purist. I love e-bikes; I ride one every day and love the ability to arrive at my destination with forty pounds of groceries without emitting as much CO2 or being drenched in sweat. I am deeply pleased by the fact that there are something like 380 million e-bike riders in China, and I envision a future in which the US has as many users of sustainable transportation.

But do we really want to incentivize the purchase of e-bikes? Is there something inherently about owning an e-bike that makes the world more just or sustainable? Or is it really about riding the e-bike; or even better, replacing our car miles with e-bike miles?

In my beloved home of Durango, Colorado, there is a great program called Way to Go Durango where you can log the miles you ride and redeem them for prizes: backpacks, ski goggles, bus passes, bells and whistles (literally). Pedal powered bikes get more points than e-bikes (fair enough; an e-bike mile uses a bit more carbon than a pedal mile), and commutes get more points than leisure rides (unfair; why can’t I count my after work mountain bike ride as activism??). It’s a cute program that provides a small incentive to “alternative” travelers who take the time to log their miles.

The other day I was having dinner with a friend who works for the City of Durango. “You know, a lot more people would participate in Way to Go Durango if users submitted their miles on the same website where residents pay their taxes and trash bills,” I lamented.

“Even better would be if you could redeem your miles for things people actually cared about,” said my friend. “You know, like savings on their taxes.”

Bingo!

Why incentivize the purchase of an e-bike when what we actually want is for people to ride the bike? Just putting more e-bikes into the world is good, but building one costs about 300 pounds of CO2 before you ride anywhere. A car mile runs about 400 grams of CO2 and an e-bike mile runs a tiny fraction of that, so a new rider has to replace roughly 350 car miles just to break even. Call it 3.5 months of a regular bike commute.

“But how should people be incentivized to ride an e-bike when they don’t even own one yet? We need to start with ownership!” My response to this hypotheical is of course, great idea, let’s do both. We have a long way to go before we are spending enough on pedestrian and cycling infrastructure.

In the US, we spend between $3.50 and $5 per person per year on pedestrian (pedestrian and cycling together, etc.) infrastructure. Germany targets $33 per person per year. The Netherlands $35. The entire $1B annual US federal bike and pedestrian commitment gets spent on US highways every 48 hours. Now is the moment to pull out all the stops. We can attack the problem from both ends.

Every car mile an e-bike rider replaces avoids roughly 0.4 kg of CO2, which at the EPA’s $210 per tonne is about eight cents of avoided climate damage. Our 100 mile per month commute assumption gives us a financial break even for the $1,000 invested by taxpayers at about 12,500 miles and 10 years of commuting. (I have had my e-bike for about five years and have only put about 2,000 miles on it, but I live in a small town and have a very short commute.) The total SROI is likely faster, though, when you take into account other factors like reduced congestion, improved health, etc. I envision this rolled out as a campaign to advocate for the roughly 50 jurisdictions nationally that have provided an e-bike purchase incentive. If you spent $100,000 to lobby a jurisdiction to allocate $1M in bike riding incentives, you’d have spurred 50M kg of CO2 emissions prevention.

Any takers?

“If a newspaper would only come out every fifty years, it would report how life expectancy rose by twenty years”

The installation is a part of Stefan Sagmeister’s “Now is Better” series, which aims to highlight the fleeting nature of our troubles, and the advancements of our species. Sagmeister was inspired by Danny Hillis’ 10,000 year clock, which, funded at $42 million by Jeff Bezos, is being installed inside a mountain in Texas.

“Short term media like Twitter and hourly news create an impression of a world out of control, with democracy in peril, ubiquitous conflicts and an overall outlook of doom. But if we look at developments concerning the world from a long term perspective - the only sense making way - almost any aspect concerning humanity seems to get better,” Sagmeister says on his website.

Two of my most thoughtful investors, Rich Rainaldi and Martha Records, taught me to respond to this type of neoliberal capital-futurist commentary with the obvious: Yes, everything is getting better… at the expense of low income people and the environment.

I think the better rationale for such a newspaper would be that this hyper-distillation would likely result in more vulnerable, profound, and ultimately honest commentary about humanity. In the same way that people on their deathbed tend to reflect on the importance of family, community, and gratitude, I believe that the Fifty Year Newspaper would read like an obituary of the past generation: The last fifty years was addicted to pills and got some DUIs, but some wonderfully kind people made love and music and held each other close when things got scary.

Of course, my head goes to, well, let’s create that newspaper.

The process of compiling such a newspaper would be a profound statement of importance and priority: When you boil it down, here is what actually matters for people half a century from now to understand about our society right now. Imagine the submissions!

I love the 10,000 year clock, and I love time capsules. This project appeals to me because it is a time capsule that pulses infrequently enough that the commentary becomes an addition to the time capsule itself.

If you played a timelapse film of the forming of a mountain range, a human life would flash by in an imperceivable blip. Within that blip, blackholes are being discovered and familes are born and yes, mountain ranges are still forming (mountaineer Gerry Roach says, “Geological time includes right now.”) If all we get is a blip, it makes sense to be intentional about how we segment news.

When I go for a run up a mountain, I always bring my GPS watch, which tracks my location and altitude with GPS and a barometer at set intervals about seven seconds apart. If the interval had the frequency of the time it took to run up and down the mountain from the trailhead, my Strava would show two dots, a couple hours apart, both at the trailhead. My journey to the summit will have been erased! Is this a tragedy? I think not.

Our data centers are already spilling over with enough useless information. It doesn’t matter that I stubbed my toe on the way up the peak, or that I stopped for five minutes to take in the beautiful view on the way down. What matters is that I am now at home on the couch next to my dog, enjoying some ice cream with my friends.

I’ll estimate the social ROI for such a newspaper via my experience compiling Begin Where You Are: The Colorado Poets Laureate Anthology. We raised about $50,000 to create and market the book. The first six months yielded about 2,000 copies sold (and because we are using the profit to fund rural and low income poetry access, about $7,500 for that cause directly), therefore impacting approximately 4,000 people per year. Assuming linear scale of per person impact, The Fifty Year Newspaper would reach 200,000 people per issue.

While I have raised millions of dollars from community foundations, donor advised funds (DAFs), and family foundations, and have many friends who work in the trenches of philanthropic capital allocation, I have never worked at a foundation myself. That’s my disclaimer.

My goal here isn’t to antagonize philanthropists, who are generally doing their best to support important causes by funneling some of the excess profits generated by our economic system to organizations they care about. My goal is to point toward an orientation philanthropy could adopt to create the world we want to live in, faster.

Gripe #1: Foundations don’t spend enough money.

You might have heard that philanthropists only have to disperse 5% of their corpus annually, roughly half the annual return on their investments assuming they are invested in public securities (many have sophisticated, diversified portfolios, and are making a lot more). For this reason, the balance sheets of foundations of philanthropies have roughly doubled to $1.6 trillion in the decade leading to 2024. There is $327 billion in DAFs sitting around in the US, and the average disbursement is 18%. Once money goes into a DAF, you can’t take it out. Why is it sitting in there, getting stale, being saved for a rainy day, when scientists agree that right now is the most important time to be making radical shifts to avoid the worst effects of climate change, income inequality, etc.?

Gripe #2: Philanthropists don’t take enough risks.

Imagine having a large endowment full of capital specifically intended to be invested, and from which you knew you weren’t allowed to personally reap the financial returns. In light of the urgent need for innovative solutions to our world’s evolving problems, you might have the inclination to swing for the fences. About 63% of foundations operate on the basis of perpetuity, meaning their desired social impact essentially takes a backseat to self preservation (enter, nonprofit industrial complex).

I am absolutely not suggesting that philanthropists should be frivolous with their capital, as I agree with the premise of perpetuity to the extent that institutional knowledge be retained over the long term for the purpose of making better investments. Long term thinking has the benefit of contemplating more risk. But many philanthropists are thinking about risk the wrong way.

For that matter, what even is risk for a philanthropist? It’s not losing the money. The IRS requires you to spend the money. The real risk, the important risk, is that the desired social returns (aka “impact”) are not generated. Avoiding that risk (beta) should be a priority for a philanthropist to the extent that it does not hamper the ability to create value (alpha). This is how all the real investors are forced to behave: generate alpha in excess of beta.

If you have applied for a grant, raised a program related investment (PRI), or otherwise raised philanthropic capital, what are the ways that philanthropists mitigate their risk? Here are some risk assessment due diligence questions I have heard countless times:

• Does your organization have a 501c3 designation?

• Does your organization have audited financial statements?

• How long has your organization been in existence?

• How will you support yourself financially after we stop funding you?

None of these questions speak to the real risk that philanthropists face: that their investments will not produce real, sizable social returns. The reason for this in my experience is that many foundations do not have the internal mechanisms required to assess their social return on investment, which brings me to Gripe #3.

Gripe #3: Philanthropists don’t know what they want.

Like any organization, most foundations have a mission statement. But despite the fact that many funders require a logic model, theory of change, or other evaluation mechanism from their grantees, many do not have an analogous system to delineate the returns generated by their portfolio organizations to their own desired social returns.

Capitalistic investors do not hamstring themselves thus. A venture capitalist, or private equity investor, or hedge fund manager, says to a portfolio company: “How much money will you earn, and over what period of time, and how much of that will we receive if we invest in/lend to you?” The investor is then satisfied if the projected returns are realized. Their returns are measured in dollars, a discrete metric which makes determining the success of an investment falsifiable.

Do foundations, DAFs, and individual philanthropists have such an unequivocal metric for measuring their returns? Some do.

I have been really impressed by philanthropists (and friends) such as Rich Rainaldi and Martha Records, and Betsy and Jesse Fink. For Rich and Martha, they say, and I’m paraphrasing, We want to reduce greenhouse gas emissions. Can you, social enterprise, do that for us? Ok, how many pounds of greenhouse gas emissions can you prevent/reduce with $1. Ok, that’s good, but this other organization is only charging half that for the same amount of CO2. We’ll allocate our capital over there, because that’s the best social return on investment. But because portfolio diversity matters as much to us as it does a hedge fund, we’ll also allocate some capital to this other social enterprise over here, which doesn’t provide as high of a social return, but provides diversity to our overall portfolio, improving its social returns in the long term.

For Betsy and Jesse, they say, (paraphrasing again) We want to reduce food waste, measured in, you guessed it, pounds of food waste prevented/reduced. How many pounds of food waste can you prevent with a dollar…?

The important difference here is that these effective philanthropists are assessing their investments in a similar way that a capitalist would: as a scarce resource, which therefore has an opportunity cost. They are seeking to maximize the social returns of their investments, and they are mitigating risk via mindfulness of their entire portfolio. Importantly, they are letting portfolio companies compete with each other to win their dollars by producing the most value, most efficiently.

This puts the onus on philanthropists to do something most of them miss: decide what you want, and how you will measure what you want.

One friend who works at a foundation pushed back on this argument during a conversation I had with her. She said, But if you’re always chasing measurable social returns, how do you ever innovate or invest in anything new? Sometimes the role of a philanthropist is to breathe life into a sector that needs a boost.

I agree with this framing, and many of my organizations have benefitted from this line of thinking as they sought to raise capital for causes without well defined success parameters. For example, no one cared about upcycled food when we started Upcycled Food Association, but Betsy and Jesse Fink had the foresight to see us as a valuable addition to the food waste movement. Before Small Capital, employee ownership within the context of entrepreneurship through acquisition (ETA) was a niche within a niche within a niche. But Gary Community Investments, Gates Family Foundation, Boettcher Foundation, and others, saw the potential for future returns, even before we knew the form those returns would take.

But my friend’s argument does not undermine my basic assertion. Foundations have flexibility with their dollars because by definition they don’t prioritize financial returns, so they absolutely should be pioneering new trends and exploring unproven sectors and organizations. They should also be taking these risks in virtue of their investments’ ability to produce social returns measured by their trusted returns metrics.

This also puts the onus on us as social entrepreneurs in multiple ways.

In this framework, organizations would need to refine their theories of change, strategic plans, and evaluation methodologies to provide a clean social return on investment statement. This is a good thing! I find it unfortunate how frequently social entrepreneurs balk at sound efficacy evaluation practices as meaningless overhead, forced on them by their philanthropic overlords. If we’re not measuring how much social value we’re producing, how the hell do we know we’re doing anything worthwhile? Vibes? If we don’t set a quantitative definition for what progress looks like in a quantitative metric, we run the risk of, as so many nonprofits have done throughout history: make things worse.

Another resulting onus upon social entrepreneurs is the need to compete: with other organizations and ourselves. I love collaboration with my friends, community, and family. But collaboration between nonprofits breeds stagnation and disorganization. The funds available to propel our missions forward are limited, just like the dollars available to a startup raising venture capital and the money available to buy groceries. If you’re finding it hard to raise philanthropic capital, ask yourself: Am I transforming financial capital into social returns in excess of that of other similar organizations? Have I taken steps to increase the efficiency by which we convert social capital into social value? Do I know how much social value I am producing this year? This month? Today?

In other words: Have I made it easy for funders to invest in me by making a clear case that I will provide more social value than anyone else?

Right now, many philanthropists follow their noses and invest willy-nilly into whatever strikes their fancy. If this is you, it’s your money, and you get to do whatever you want with it, but don’t expect to solve any major problems that way.

Meanwhile, nonprofits are raising money on vibes, branding, and narrative. This does a good job at making people who donate to charity feel good, but it prevents us from creating as much impact as we otherwise could.

It doesn’t have to be this way. By treating philanthropy like a global competition to solve the world’s biggest problems, we will arrive at the future we envision faster, with more precision, and with more integrity.

In the coming weeks, I’ll begin to demonstrate what I mean here by starting to post about some of the hundreds of social enterprise ideas I have, estimating the social return on investment for even the most hairbrained, niche, and immeasurable concepts.

Next month, I’m releasing a new website, which compiles all these ideas into a unified ledger, complete with SROI calculations from projects past, present, and future.

1. There is the enjoying of the waves and riffles, curved cliffs of peach and maroon sandstone towering overhead; and

2. There is the climbing of the walls to take a barometric reading, measuring the width of the river to estimate its flow, and tracking the stars with a sexton in an ever-darkening map of the unknown.

In two previous articles, I discussed the feeling of leaving a business, from an emotional and practical perspective. This article is the thinking: a temperature taken of the lessons learned, and a cartography of the nooks and niches of a mysterious and challenging business, Small Capital, which took co-founder Jamie Finney and me on one wild ride.

Note: I highly recommend keeping an eye out for Jamie’s take, which he’ll likely post on the Small Capital blog, or the highly reputable newsletter, Innovative Finance. Both are worth a follow.

For a quick background on Small Capital, I recommend this article from their blog, or this article from The Social Entrepreneur.

These are the most important lessons I learned at Small Capital.

1. Employee Ownership is Missing Its Biggest Opportunity

Most businesses are small, 99.9% of them, but most employee ownership work is focused on big. This might be too simple of an observation. Just as private equity built an industry on buying and selling large companies, and then migrated down-market to smaller and smaller enterprises, I hope that employee ownership work refocuses on small(er) businesses. For one, that’s where people work. Forty six percent of Americans work in small businesses. It is also where the culture change needed to sustain a successful employee ownership transition can find a toehold.

At first, we at Small Capital tried to ignore the pesky topic of ownership culture implementation. Meddling with a company’s culture seemed too messy, when all we needed to do was show up with the right capital product to spur more employee ownership conversions. We’d planned to hire culture change out to one of the many cooperative ownership nonprofits who can hold the hand of a retiring business owner, rallying the employees to think like owners. More research arrived, finding that the culture was just as important as the financial incentive at unlocking the myriad benefits of employee ownership that we and other EO advocates shout from the tops of cliffs. For example:

• Employee ownership will make your business more profitable.

• You can still get a fair market exit when selling your business to your employees.

• Resources, incentives, and professionals are here to help you with your employee ownership conversion.

There is no perfectly scalable solution to this problem. Scaling business culture change is a concept as rich as scaling…love; sure, a business could take it on, but it’s better left to the small groups of people–friends and families–who will do a better job of it themselves. The best we can do as an industry trying to advance democratic ownership is to show up in the places where culture change is most congruent: small businesses.

2. Employee Ownership is Too Slow

Colorado is the “Delaware of the Co-op,” with its Employee Ownership Office inside of the state government, increasingly generous tax incentives for becoming employee-owned, and many of the leading philanthropic funders and investors in the space. And yet, the number of employee owned businesses in Colorado grew from about 200 to somewhere in the low 200s in the past four years since starting Small Capital. There are over 600,000 businesses in Colorado.

We did not help this problem on paper, as we were unable to get an employee ownership investment deal done in our first four years. This was not for lack of grinding. We had many late nights and long weeks, as we tried our darndest to make good of our number one project: Get A Damn Deal Done.

It is a Messy Marketplace, the world of small business. That will always be true. The best we can do is follow the river-safety instruction for when you fall out of a boat: remain calm, don’t thrash, and go with the flow of the river.

Small business investing happens at quite a fast pace. I was amazed when attending a Colorado Association of Business Intermediaries (brokers) conference and seeing dozens of brokers, all ostensibly buying and selling half a dozen businesses per year. How is there enough work for all these people? Yet, as the Small Capital blog asked, “Where Have All The Employee Ownership Deals Gone?“

The Employee Ownership (EO) movement needs to speed up. There are two ways I believe this can be accomplished: More actors, and faster dealflow.

There are nowhere near enough EO investors, banks, and consultants out there to ensure that even one percent of the 10 million baby boomer-owned businesses convert to employee ownership. Anyone acting right now should be sharing their strategies open-source. The best innovation to come is still a long way out, and no one will win alone.

To move faster, we ought to put our oars right in the thalweg, where the water is moving fastest. There is nowhere I have seen with faster, more urgent dealflow, more ripe for employee ownership than in the entrepreneurship through acquisition (ETA) space. Young “searchers,” individuals seeking to personally purchase a business, might sift through a hundred businesses a day, and when they find the right one they move quickly. These “search funds” are precisely where employee ownership makes most sense: small businesses inherently undergoing leadership transition, where the buyer needs to win their favor as a business imperative.

Whoever solves this problem of bringing EO and ETA together at scale is going to make a lot of money and help a lot of workers make more money, too. I am proud of the progress that Small Capital made to this end.

3. Capital Matters…

When you are working with small business owners at the moment of retirement–that is, when they are trading in decades of passion and dedication; the very substance of how a human being used their one wild and precious life–for a measly one-time payday that will likely neither satisfy their financial nor spiritual needs, you are working with someone through a truly profound chapter. They would be better off with a therapist than a banker.

Yet, the people who are summoned to this occasion tend to be impersonal and explicitly financially motivated: lenders, lawyers, and the like. The small business mergers and acquisitions (M&A) world slaps a sticker on this situation: we promise to take care of your team and your legacy, they say, if a little disingenuously.

While we certainly validated the evidence that legacy and employee wellbeing are top priorities of selling business owners, we also found that simply saying so wasn’t enough. We often found ourselves in hours-long conversations, hearing out an owner’s nostalgic perseverations of the tradeoffs, or simply listening to them tell stories of the good days and bad.

The emotional side of the equation is one of many factors that points out the importance of advocating for employee ownership on a local level. One investor and advisor told us, “If you’re working on employee ownership nationally, that is less interesting to me than if you are working in Colorado, and that is less interesting to me than if you are working in my county, and that is less interesting than if you are working in my neighborhood with the businesses I visit everyday.”

Working in rural Colorado was an advantage, because businesses trusted us. Showing up to a meeting as an “investor” wearing the “Durango Uniform” that won our little town the title of Worst Dressed City in America–a flat brimmed hat and flannel shirt–did more for our credibility than our sophisticated financial modeling or industry insight. These are the businesses that are truly to be “otherwise missed” by the Silver Tsunami opportunity. And they are the most important to protect.

This is all to say that the hundreds of mostly rural Colorado small businesses we talked to cared more about our trustworthiness than our financial innovation. Still, we knew that with the small size and infamous messiness of small business, we would have to innovate on a specific capital product in order to reach our goal of scaling employee ownership to the size of the small business ecosystem.

This was a challenge we were equipped to take on. Jamie Finney ingeniously invented a redeemable equity application that would sit between senior debt and mezzanine financing such as seller financing. This instrument filled the gap that debt wouldn’t touch, and brought a market-rate exit within grasp for the seller, all while transitioning ownership to employees within a few years.

We soft-circled a couple million dollars for a fund with this strategy in 2025. The fundraising was a challenge, but we found that our investors resonated with the concept of earning a return by owning shares in local businesses. We had cash runway to burn thanks to the critical philanthropic capital that kept us afloat. (We had previously started a lightweight, fiscally sponsored nonprofit organization that housed all our open-source research and development of new employee ownership investment methodologies, which, critically, allowed us to solicit grants from foundations to fund our pre-revenue operations.)

But as the variety of unique circumstances exploded exponentially with each small business we talked to, the need for more flexible financing showed its teeth, and the need to fill the equity gap shrunk. Small business owners asked, “What if I only want to sell a portion of my company now, taking “chips off the table” and riding the employee ownership wave for the next few years? What if I am a searcher with an SBA 7a loan? What if I want profit share versus stock share for my employees, or vice versa?

This level of diversity hindered the prospect of a hyper-scalable single capital product, but we were dedicated to the quasi-academic question of what capital product(s) would actually work in this market to scale EO. We pivoted to an special purpose vehicle (SPV) model, theoretically allowing us greater deal-by-deal flexibility to meet each business where it was at. By the time I left Small Capital, Jamie Finney and Stephon Smith were cooking up some incredible systems for running diligenced companies through a model to back into the right capital structure to meet the needs of the unique deal at hand.

I think this hyper-flexible, deal-by-deal investment structure has legs. Because: Relationships matter and local matters, maybe more within small business employee ownership investing than anywhere else in private equity. I foresee the most prolific employee ownership investors of the decades to come being those who can activate small groups of local investors around a single deal, carefully navigating its eddies and rapids.

Those quirks are not going anywhere. If we don’t bend over backwards to make EO fit into small business M&A, then small business M&A will continue to dredge its well worn path towards wealth concentration and power consolidation.

The way to test and validate these myriad solutions will be through philanthropy, which, you guessed it, has a long way to go.

The foundations in the EO space are smart, forward thinking, and knowledgeable about employee ownership, and I’m not just saying that because they supported Small Capital. But I hope in the years to come they use the true power of their philanthropic flexibility by seeding new employee ownership investment strategies rather than investing in the few handful of early winners. We’re all looking for a market-rate solution here, one that will attract even the most rational of capitalists, be there a do-gooder twinkle in their eye. So if a fund has already raised $50 or $100M+, it’s time to go down market and seed new, untested ideas rather than bolster the frontrunners. It’s a messy marketplace. No matter how big an employee ownership fund gets, it will always only be able to invest in a tiny subset of an already niche market. The gap is in the number of diverse investors providing a wide range of solutions, not in the number of dollars we put behind one particular solution.

One employee ownership researcher said to me, “The employee ownership investment industry is in its adolescence. We’re all throwing spaghetti at the ceiling and trying to figure out who we are.” For at least the next decade, I would measure the success of philanthropy on the topic of employee ownership by the number of unique, niche, and weird solutions incubated, rather than the number of dollars invested (or even dollars returned).

4. …But People Matter More

In total, we prospected (identified as potential fit for EO transition) about 550 small businesses, mostly in rural Colorado, but many in the Denver area and across the country. We talked to about 220 of them between the 3.5-ish years between when I founded Small Capital and my departure in 2026. We did basic financial modeling for over 50, and full diligence on about 10. This is prolific progress for a fledgling firm, yet the total companies we connected with was only 0.002% of the 10 million Silver Tsunami businesses that will need new ownership in the coming decade (most of which in the next five years).

But counting the number of small, mostly blue collar businesses you have met with is like counting the friends you’ve made–it’s as futile as attempting to quantify the value of a human life. When you’re dealing with a small company that a regular guy started 30 years ago, when life was still filled with unknown and glimmering opportunities, and then gave his life to the enterprise such that it becomes a defining feature of his spiritual existence, a small business is a human life.

Concrete formers, tree trimmers, plumbers, electricians, pizza chefs, rebar fitters, baristas, well drillers, screen printers, and solar panel installers. The men and women who own the countless small businesses we invisibly rely on for everything from bike parts to furniture are not financiers or MBAs. They were thirty-somethings that knew how to do their craft better than anyone else in their communities. They took a big risk, not usually with debt, but with their precious time. They slept on friends’ couches and ate cheap food for years. They took over running the business when their spouse died. With misty eyes, they told us about the memories they never made with their children.

It’s tempting to make running a small business an allegory for a human life, with its myriad challenges, opportunity cost, and rare triumphs. But as Rainer Herdrich, the man who skied every day for 3,000 consecutive days, points out, eventually the way you spend your time supersedes an allegory. It is just your life.

And now, after decades of that life, 80% of your wealth is tied up in this business. If you’re lucky, you could sell it for four to six years’ worth of profits. “Why not stay another six years and retire later?” we’d ask. “I am ready to return to my family,” one owner said.

It is a profound honor to be with a person at the time of death, say the hospice and medical workers who witness a human life pass on. It is the same honor that one feels when officiating a wedding, or being present for the birth of a child. We felt this same honor in bearing witness to the passing on of a small business. In this moment, an owner’s mind goes to a garden of deep sentimentality. It was common to spend a whole hour with an owner and never talk about capital. “I just want my people to be okay,” they would say. “I have spent more time with my employees over the last twenty years than I have with my partner.” “They built my wealth with their precious labor. I want to take care of them now more than ever.”

Of the thousands of hours and hundreds of conversations, we heard exactly one (1) SMB owner say he didn’t think employee ownership was a good idea. Something to the effect of, “My employees don’t have what it takes to be business owners.” Which reminds me of when Admiral Alexander Shishkov said to Tsar Alexander I, “To teach the mass of people, or even the majority of them, how to read will bring more harm than good.” Every other owner was equally thrilled and ignorant of their options. Their values, their priorities for retirement, the skills of their employees: every facet was perfectly congruent with selling to their employees. They simply didn’t know it was a possibility.

Of course, they have heard the horror stories of selling to private equity, where their employees are fired, the plant is moved out of state, the business is levered up with excessive debt, and once it becomes a single line on a balance sheet in New York City, it is dumped into oblivion.

The small business owners we talked to vividly wished to avoid this fate. Yet their understanding of any alternative option was so opaque, many of them had accepted this well-worn path as unavoidable.

This lack of agency is as tragic and unjust as withholding the desired option for end of life from a dying patient. And the answer is relatively inexpensive.

Educating business owners about the option of employee ownership was not our imperative at Small Capital, but it became one of our most impactful outputs.

The education gap within the nascent employee ownership movement is wide, and reminds me of the education gap I saw in my 10+ years in the food waste movement. In food waste and employee ownership, we have academics, lawyers, philanthropists, and investors waving their findings above their heads, investing vast sums into systematic solutions, when the average person is still throwing perfectly good food into the trash (so to speak). And in both of these movements, the respective critical actors–owners and consumers–easily intuit the solution. Our affinity not to waste food, like our business owners’ affinity to their employees, was natural as if to be evolutionarily engrained.

The easier solution, then, is to activate this natural reflex: tell the truth to business owners. “You can retire comfortably, even earning an exit on par with that of private equity, by selling to your employees.”

Until we build massive demand for employee ownership within owners, each employee ownership actor will continue to chip away the problem 0.002% at a time. This marginal progress is not to be discounted, and my heart goes out to the capital entrepreneurs doing life-defining work building solutions to actualize democratic ownership of business across the globe. Their work gives us the missing link needed to amass owner-demand: success stories.

As I prepare for my own journey down the Grand Canyon (Jamie Finney will also be on the trip), I turn the last page of Beyond the Hundredth Meridian and pick up another book about our nation’s greatest natural beauty. A Walk in the Park by Kevin Fadarko tells the true stories of the few and far between successful attempts at the 200+ mile trek on foot through the Grand Canyon. Fadarko, a long time Grand Canyon river guide, speaks to the substance that carries wonder through the Canyon and through generations. No, not water. Stories.

“If there was a reward to their venture, perhaps a portion of it was being handed to them tonight as something merged with the here and now: a cluster of humans, sitting in a circle, sharing stories beneath the canopy of the night.”

Since then, I have started and later walked away from half a dozen other social enterprises, most recently Small Capital. The process of leaving Small Capital couldn’t have been more different than that of DFR. A fully remote finance organization founded after the Zoom revolution compared to a neighborhood-based food distribution nonprofit, leaving Small Capital required little more from me than sending some emails to investors, lighting a candle in my backyard, and blowing it out as I said goodbye.

Every departure from a job is different, but consistently I find the process of walking away to be one of rich, intense feelings: catharsis, elation, grief, sorrow, and joy.

Or, in other words, leaving your social enterprise shares the same heartbreaking recipe of ingredients with a romantic breakup. Yet much of the common advice focuses on the practical “how-to” questions instead of the emotional “What is the purpose of my life now?” ones.

These questions are ubiquitous among those who brave the sacred act of departure. Sacred, because from departure comes closure. From closure, new beginnings.

Those of us who feel these feelings most intensely seek a thoughtful departure that does justice to the experience of the work; a leaving commensurate with the staying.

When preparing to leave DFR, I read all the books about how to leave your nonprofit as a founding executive director. I thought, Wow, you really have to give your board that much notice? You really need that much money in the bank to pull it off? These best practices are well documented, and I’ve given my take on them in another article. What I want to talk about here is the art, the gift, the grief, of walking away.

As reliable as lilacs in spring, eventually, all my social entrepreneur and nonprofit worker friends will call me. When the call arrives four-to-eight-years-on-the-nose after they took on the job, I can hear it in their voices. By then, the sheen of the fancy title has worn off, and there is increasing certainty about the legacy they will leave as the non-forever leader. I have wondered if this waning uncertainty is what ultimately pushes us away. Certainty is poison to the type of person willing to lead an organization, an act of such utter uncertainty that it’s best described as–to quote John Wesley Powell upon his voyage down the Grand Canyon in 1869–an adventure into the “great unknown.”

Give me uncertainty, we organizational leaders plead, where I can paint the vague margins with a vision all my own. Give me blue sky, where my story is yet unknown.

When they call–these friends who are clearly ready to leave their social enterprise or nonprofit role–they ask the same relatable questions: What will the board think? How will I ensure the organization is in a good place? What if I wait two more years, which is how long I tell myself I need to get the organization satisfactorily efficient, effective, and flush with cash? A tender heart that was attracted to social enterprise in the first place does not want to dump its old job; it wants a conscious un-coupling.

These are fair questions, and they are folly. Like a romantic relationship, there is never a convenient time to leave.

I’m sure you recognize the first few elated weeks after a breakup, when all your crushes are out around town, and you are swiping right on Tinder on dates that do not meet your standards as fast as you can click the “Easy Apply” button on LinkedIn. You know the gleaming allure of possibility.

These are the moments before the loneliness sets in; the realization that yes, you will still be the observer in the new world, with all your disorganized thoughts, habitual fears, and unfolded laundry strewn about a field of view which isn’t as sunny or sexy as you had imagined. Damn.

But the most terrible and important way that leaving a job is like a relationship breakup is the advice: don’t worry.

One of my many favorite Andrea Gibson quotes is, “The universe does not have the ability to give you anything other than exactly what you need to grow.” There is one fact about life that will always remain unequivocal: you do not have control. There is a special and, if you let it be, spiritual opportunity to confront this fact. The moments around when you are leaving a job are an opportunity to tap into the wonder of your “one wild and precious life,” (Mary Oliver, obviously) relating to what is important to you in new ways. Parker Palmer says in his book about vocation, “Let Your Life Speak,” (required reading for anyone undergoing a job transition, as far as I’m concerned) says, “The core message of all the great spiritual traditions is ‘Be not afraid.’” What would these, and the other wisest poets and thinkers, tell us to do about our ex, and therefore, our job?

Don’t worry about your ex.

That is, do not worry about the board, the staff, the funders, the investors, and the volunteers. Your ex is going to be just fine. Your ex is an intelligent, autonomous human, who will find new love just as quickly as you will.

Don’t communicate with your ex.

Unless you possess some unique skill that only you can bestow upon the organization (no, experience and network does not count), then it is likely counter productive for the long term health of the organization to take a strategic advisor or board role.

Do not worry about your reputation.

When leaving Upcycled Food Association, I made the stupid mistake of not telling one of our investors in a PRI we were actively raising that I was leaving the organization, mid-negotiation. Pretty much right after the investor committed to the PRI, I announced I was leaving, which understandably lost the trust of the investor, who ended up not committing to the PRI, and years later, opted not to invest in Small Capital. This is just about the worst case scenario, is it not? I made a mistake related to leaving an organization that hampered future opportunities in a very practical way. And was it bad? Sure, it was pretty bad. But I’m fine. The organization is fine. Everything is fine.

(Consider the thought experiment: the would this be an interesting story at a party test: If you departed your job like Dwayne “The Rock” Johnson leaping from an exploding helicopter to the roof of a skyscraper, then that’s a great story for a party, and therefore, might require some rumination. But if your story is essentially, “I left my job and some people are mad at me,” then don’t bore your new friends: Everything is fine.)

We were still able to raise millions of dollars of commitments into Small Capital, and we learned an important lesson that helped me avoid a similar situation in the future. When planning my departure from Small Capital in early 2026, we were deep in the midst of a years-long cultivation process with a large foundation that was just on the precipice of finally making a grant. This time around, I intentionally conversed with the funder about my departure prior to signing the grant agreement. I explained what was happening, why, and what this meant for their grant: who would be handling my responsibilities, how we would still make good on our promised outcomes. This time, instead of getting an angry grudge, I got a nonchalant, “Good luck on your future endeavors!”

Do not pine over your ex.

You were never your ex’s soul mate; that is, you’re really not that important to the organization. Even if you are CEO or another executive, you really don’t matter that much. Your board, funders, staff, and volunteers, are not participating because of you and your masterful cultivation. They are there because your organization does cool shit. If I’m wrong, and you really are the linchpin of your organization, then we have entered a tundra of circular logic, where I must point out that any leader worth their salt creates an organization that stands on its own damn feet and isn’t propped up too much by the their personal charisma.

In other words, if you have built an organization that cannot survive without you, then you have failed, and should likely find a different organization to lead, or do something else (there are way easier and more fun jobs than leading a nonprofit or social enterprise!). I am, my dear friend, compassionately, dead serious, and, to be sure, have made this mistake myself.

Do take care of yourself during your breakup.

It may feel like folly, especially if you were dumped (a.k.a. pushed out or plain fired), to live in a world where you lack the structure, purpose, and accolades that your work provided. A friend told me that in the midst of his career transition, he was so depressed that his favorite activity, skiing, tasted like ash in his mouth. The worst thing to hear in these moments when your love is gone–your ambition and vigor for life dulled into a monotony of daily tasks and you realize just how much of your waking hours were dedicated to pursuing your dreams–is exactly what you need to hear: just drink more water; eat healthy food; exercise; see your friends; journal; meditate; go to therapy; take meds if that’s helpful; etc. These shallow tasks might feel like fodder for a fatal existence. Yes, exactly. So is your career. And yet you show up every Monday morning.

(I like to think that these wellness activities make a 5% difference, each imperceptible on its own, but making a profound difference in aggregate.)

Two of these “five-percent-better” actions have been particularly helpful to me while wading through the grief of walking away from a role: meditation and therapy. I highly recommend working with a therapist or coach to help build structure around your transition. Just like the Tibetan Buddhist practice of Phowa, where the quality of the meditation at the moment of death can have a profound impact on the result of reincarnation, the days and weeks immediately after your separation from your job will have a lasting impact on your habits and your frame of mind as you endeavor to find something new.

Hold A Ceremony

A long time friend and business partner instructed, as I ruminated with anxiety about leaving Small Capital: light a candle. One important emotion that will almost certainly arise during your career breakup is grief. This most powerful and sacred experience might connect you to countless bereaved ancestors, or it may floor you in desperation.

I took the Emotional Response-Ability course at the Institute of Adaptive Mastery after going through a hard breakup that coincided with leaving Upcycled Food Association. It ended up being one of the most important coaching experiences ever, and remains on my mind to this day, as I try my damndest to transform challenging experiences into productive or even lovely moments.

The Emotional Response-Ability modality asks us to consider how our subconscious minds process hundreds of thousands of times more information than our conscious minds, and therefore negative emotions are useful inventions of the wise and observant subconscious to spur necessary action. For Grief, the subconscious is sending the message, “Hey, I need you to mourn a loss.”

You know, that dream you had for the future of the organization and your place in it. Your face on the magazine, your legacy in the movement; some change for the world, finally on its way. Living in a world where you know this dream will not come to fruition can be excruciating to the point that you may want to disappear underwater. But ERA reminds us there is a path through grief: mourn your losses. This epic and overlooked skill is just that, a skill. Practice it. Light a candle at your altar, journal in the sunshine, and cry in solidarity with your bereaved ancestors, who felt the same way you do now thousands of years ago.

When it finally came time to leave Fresh Food Connect, CEO Kayla Birdsong joked that after eight years, it was the longest relationship of my life. (Hilarious, Kayla!) In this case, though, the typical grief was overshadowed by an immense gratification. I knew Kayla for years in her role as ED of another successful nonprofit. She had become one of those work friends you look at across the boardroom table and wonder, wow, how do you manage to say the exactly right thing all of the time? In every way, Kayla was the right person to lead Fresh Food Connect. She is one of the most talented leaders I know. I felt excited to get the hell out of her way and let her run with it. To let her take it to someplace I never could have.

Same story with Small Capital. Unlike me, co-founder Jamie Finney came to the organization with a decade of innovative finance experience, having served as the GP for multiple funds, raising tens of millions of investment capital, and making dozens of investments. On the other hand, I was learning the basics of accounting, doing this mysterious, scary-sounding thing called “due diligence” for the first time, and raising money on the back of my success having started multiple previous nonprofits, but never having invested other people’s money.

Now, upon my happy departure from Small Capital, it is totally obvious that Jamie is the right person to lead the organization. He is brighter and more connected and beloved in the industry. People actively respect him, whereas they were, and fairly so, dubious of me. Not to say I didn’t have anything to contribute. But herein lies the important lesson in humility that leaving your organization is trying to teach you: your organization is better off without you.

While you may have been the only person in the universe with the vision and volition to get the project off the ground, there is a near zero chance you are the right person to help it soar into the sky. We have all heard that starting and managing are two different skillsets, but what I’m getting at goes deeper than that.

The organization has changed.

The world has changed. You have changed. The unique and wonderful talents that made you the best person for the job when you took it no longer hold true. There is someone out there who contains a more magically congruent set of skills and experiences. They are out there, passionately waiting for the opportunity. If you cared more about the mission than your ego, you would make it your goal to go find that person. Right now.

All of this might sound belittling. I promise it is not. You have your own magic combination of tools, and your next opportunity will relish in your use of them. But in the meantime, you will be heartbroken.

The grief that comes with leaving (or losing) your job is a special breed. I have heard friends discuss the death of our pets as particularly difficult because of the unique way we see their entire lives, start to finish, enveloped within our own timelines. The same is true of your job. You saw the whole lifecycle of your job from the most intimate vantage. You experienced the epic story arc in your bones and blood. You felt the elation of first love, and felt goosebumps after a triumph. You led others through challenging times of their own. And you were celebrated with accolades, a microphone on stage, a viral Linkedin post, an interview in the media. Genuinely, congratulations, friend. You worked hard, even when the work was hard on you.

Who are you without this story? What meaning does your life have, if not as a channel for this epic to speak through? What purpose does life have, short as it is, if you are to slide into the darkness of irrelevance, never to leave a mark on history? One of the most terrifying realizations for an entrepreneur is that you die twice, once when you stop breathing, once when your name is said for the last time. The brilliance, energy, and measured arrogance that gives an entrepreneur the power to create something also makes the prospect of invisibility particularly frightening.

There is no cure for this fear, sadly. The solution will emerge silently, unnoticeably, in meditation, drinking water, exercise, community, five percent at a time. If you reach a serious darkness that is not safe to linger in, I hope you, as I have had to multiple times, seek professional help. I hope you will, as I have failed to do countless times, simply sit with the feelings as they arise and pass through your body, noticing their depths and contours without rejecting them.

Then, eventually, a leaf will fall in your lap, perfect in its autumnal yellow. It will distinctly feel like the right time, in that moment when you least expected it. For there is a cure to the gift of grief that loss bequests us. It is unreliable in its timing, but never falters in its showing up eventually. This solution makes poetry out of your pain, and illuminates a new path you couldn’t have dreamed of, despite your sharp foresight, your broken heart, your mind, spinning with ideas:

To fall in love again.

In fact, I have made big mistakes when leaving my organizations. For example, I left one organization when it was still too reliant on my personal relationships I had cultivated with the industry, resulting in declining revenue. When leaving another organization I founded, I left the organization amidst a cash crunch that resulted in the new CEO having to lay off half our staff.

In other words, I’m not an expert in this because I’m particularly good at it; but I do have the benefit of sample size. For 15 years, my focus has been starting and scaling social enterprises. In five cases, I was able to successfully grow the organization and hand it off for it to flourish under smarter, more qualified leadership. (Four nonprofits, one for profit business.)

I have heard a lot of flack over the years about the right and wrong way for a nonprofit executive director to leave their organization, or how a founder can most eloquently transition out. A lot of what I have heard is bullshit intended to get organizations to hire expensive consultants. Others will likely call what I’m writing here bullshit. Again, this isn’t academic research. It’s my hard won opinion, which has worked most of the time.

Leaving your job, like leaving a relationship, is a spiritually important process. Deep care is required, and you’re bound to break your heart on a path to self actualization. If you want to read my thoughts on the matter, you can see this other article, where I discuss the grief, loss, and elation of leaving.

This article, however–this one you’re reading–gets to the practical matters.

This is mainly written for leaders of social enterprises and not-for-profits, and will likely resonate most with founders and nonprofit executive directors in particular. But I hope that some of this will be helpful to anyone who wants to leave their job in a thoughtful way.

How Much Time Do I Need To Give The Organization?

I have read that you need to give two years of notice when leaving a nonprofit that you founded. I think that is way too much. The two-year approach basically says, “No one can do this except for me, so I need to be the crutch of this organization until it’s able to limp off into the forest without me.” A truer statement would be, “There are many people who could do this job better than I can, and it’s my goal to get them into this organization as soon as possible!” In my five successful departures, I gave my board 10 months, nine months, seven months, four months, and three months, respectively. The difference depended on the financial health of the organization, the organization size (with larger orgs needing more time), and whether there was a pre-selected leader. (In the three months example, co-founder of Small Capital, Jamie Finney, took the reins. It was as much his organization as mine, so it wasn’t necessary to do a long transition of power.)

How Much Overlap Time Do I Need With My Replacement

This has again depended on the shape and size of the new organization. For me, it has ranged from about five weeks of fulltime overlap to about four months. It doesn’t really depend on how much you trust the new leader (if your board has hired them to replace you, it’s now your job to trust them without hesitation, if with a little guidance). Rather, it seems like the time range has more to do with the number of important relationships that need to be passed over. I remember transitioning out of Denver Food Rescue and getting coffee with major donors all day with the new ED, just letting her shine while I encouraged the donor to give her their attention and trust. These relationships are virtually the only thing that the new ED shouldn’t be able to figure out on their own.

When Is The Right Time To Tell My Board?

Now. When you’re thinking about it. Even if you don’t have a plan. Even if you don’t have your next job lined up. As executive director, you hold a significant amount of power over the board, even if it doesn’t always feel that way. They know that if you bail, they are screwed, and will have to swing into action to find a replacement. I have never heard of an ED telling their board “too early” and the board pulling that move that my boss at a restaurant job said when I gave my two weeks: “Naw, you should just go now.” In fact, I think the more insight and advance notice you can give the board, the better. It helps build trust and give everyone a long timeline to do the right thing.

How Much Money Does the Organization Need?

The same amount it needed while you were running the organization. More than nine months you’re golden, more than six months you’re fine, more than three you’re worried, less than three and you’re scrambling. Nothing about your transition necessitates that somehow you need to have more cash than otherwise. Other than the time that you and your replacement are both on payroll simultaneously, expenses don’t need to increase much at all (though other expenses can include consultants, headhunters, and this stuff can be really expensive). If you hire from within, your payroll expenses could actually dip briefly. In any case, the reason for the margin was to cover events like this. Carrying too much liquid cash is just as irresponsible an investment as too little. Besides, if you could have been growing your budget all along, you should have done that already. Save the boost in fundraising for your charismatic new leader. (I certainly recommend a campaign centered around “Hey, I’m the new ED, I want to get to know my community. Want to get coffee?”)

Some other financial metrics I have learned during my time consulting for 20 Degrees, a great business dedicated to helping social organizations make more money:

• Days Cash on Hand (how many days you could cover expenses using just the cash in your bank): aim for 180+ days, or six-plus months of runway.

• Defensive Interval Ratio (the same idea, but counting all your liquid unrestricted assets, not only bank cash): aim for 210+ days, or seven-plus months.

• Program Expense Ratio (the share of your spending that goes directly to your mission): aim for 65-85%, and don’t drop below 60%.

• Government Reliance Ratio (how much of your funding comes from government sources): keep it at 40% or lower.

• Self-Sufficiency Ratio (how much of your operating costs you cover through earned income): aim for 30% or more.

• Return on Enterprise Capital (how fast your unrestricted revenue is growing relative to your unrestricted net assets): aim for 10% or higher.

• LUNA % (the share of your net assets that are both liquid and unrestricted): aim for 60% or higher.

Again, these are the metrics that indicate financial health at a typical nonprofit (and some social enterprises) regardless of whether there is a leadership transition or not.

Who Should We Hire To Replace Me?

Ideally, your organization has a strategic plan and fundraising plan in place that extends at least a couple years in either direction of your departure. This helps solidify your institutional knowledge and gives new leadership a roadmap that was validated by your lived experience. If that’s not the case, then I’d strongly consider making it the case before you leave. If the org does have these plans in place, then the decision of who to hire is quite simple: it’s the person who can most effectively execute on those plans with the budget you have available. That is pretty obvious, but here is my more radical take: that person is likely already a part of the organization. I have seen firsthand how powerful an internal hire can be for morale, continuity, and growth. Four out of five of my successful transitions were internal hires. (I love the benchmark of thinking through every hire across the organization this way: could this person be the next CEO? The answer will often be no, and that doesn’t make them the wrong fit for some other role. But having one or two strong leaders who are subconsciously jockeying for your role at any point is smart.)

When I was transitioning out of Upcycled Food Association after founding the organization four years prior, my 20 (!) board members and I did a thorough, professional search around the globe for the right replacement; someone who could take this ambitious nonprofit to the global scale we knew it could achieve. Ultimately, we found the right person in Angie Crone, who had served as the Program Director for about two years prior. I will never forget the moment when we announced to staff that Angie had been hired. A dozen adults erupted in happy tears. Angie’s direct reports were so damn proud of their boss. The team showered her with congratulations and gifts, including a mug that read in sassy cursive, “The CEO.” Angie had a tough job on her hands. But given how much trust the staff, board, and entire industry in which we operated already had in her, there is no one in the world who could have done it better. If we could have accepted that the right person was right under our nose instead of hiding inside the mystery box, we could have saved time and money. Alas, we made the right decision in the end.

Should I Stay On As An Advisor or Board Member?

Probably not. Unless there is some part of the strategic plan that you can advise on better than anyone else globally for the same price, it’s cleaner for you to walk away entirely. If your replacement calls you in a tizzy asking where to find some document in Google Drive, or for some advice on how to manage a difficult employee, then sure, pick up the phone and help out. If you or someone else is pushing for your continued involvement because you have institutional knowledge, relationships, or experience, here’s why those reasons are too weak: Transitioning those assets is what your overlap period with your replacement is for.

If what you have is technical knowledge about a specific problem that is expensive and painful to the organization, there is a 99.9% chance there is someone more qualified who understands that problem better than you do who can advise the organization for the same price. If you’re in that 0.1%, then go ahead and stick around! (If you want.) Otherwise, you risk making the mistake that many leaders make when they come to expect their replacement will do things their way. Your job during your transition is absolutely not to help the new leader do things your way. Your way is no longer the right way for the organization, that is why you are leaving.

Your job is to eliminate as many barriers to your replacement’s success as possible by transitioning institutional knowledge and relationships so they may succeed or fail on their own accord. If they truly needed your help with the technical or leadership skills needed to do the job, then they are likely the wrong pick to lead the organization. Do everyone a favor and do not become that “Founder from Hell” who sticks around the office micromanaging everyone, speaking from a high horse in the board room.

What Do I Do If I’m Getting Fired?

One of the hilarious, invariable experiences we have when we’re leaving a leadership position is that people will wonder if you’re getting fired. Even if you did a great job and you had a good reputation at your organization, there is still this instinct to whisper questions under the table: “I wonder if there was a controversy with the board president…” Or, “I wonder if they were a bad fundraiser…” This says more about the way adult Western humans naturally gravitate towards drama than it says about you or your organization. The reality is, however, that even if you leave under your own volition, there’s likely to be some hard feelings floating around the organization upon your departure. Even if you pull off your transition with the most seamless eloquence and selfless humility, there will still be winners and losers. Knowing this, holding this tension, and being compassionate to yourself and your team is the way through.

If you are in fact getting pushed out or fired, that’s a completely different situation, but the philosophy holds. Rather than fleeting feelings of resistance or sadness, there might be full-fledged rage and resentment. Do not give in to these unskillful thoughts, which will invariably last a short time. Objectively speaking, it is likely that you are wrong and you are at fault. It is equally true that your adversaries are wrong and at fault, but most true of all is that neither and both of these facts are true and false at the same time.

The best way that you can take care of yourself and the mission that you care so deeply about is to be honest, supportive, and kind. Walk away with integrity, and then tell your family, your future employers, and yourself the truth: You’re a great leader who did the best you could with the constraints you had, and the organization decided someone else was better equipped to accomplish the next chapter’s goals.

You got into this work because you cared about some topic area that, let’s face it–unless your non-profit is focused on distributing photographs of Bad Bunny to populations around the world–is pretty niche. You convinced some people to donate their time, talent, and treasure along the way. You fought for what you believed in and made the world a better place. You honored the opportunity with your presence and dedication.

Or, in other words, you were truly alive.

So, here they are, in order of how much time I spend on them:

Who is going to buy the 70%+ of small businesses that are owned by baby boomers? We think the best case scenario is that the employees do. But employees don’t have the money to buy out their bosses. So we created an investment fund to provide business owners with the liquidity to transition small businesses to employee ownership. Not only can this help increase the wealth of lower income workers, it can make businesses more profitable. This presents an opportunity to invest in stable, established cash flowing local businesses.

Take Our Survey

We are looking for the most beloved small businesses in Colorado. Oftentimes, the best businesses for employee ownership are already local favorites. If you live in Colorado, take this 5 minute survey to tell us who is the most beloved business in our state.

Children in rural and lower income areas don’t have access to as much poetry as their urban and rich peers. Yes, poetry. It’s easy to take this art form for granted. There is a position out there who is meant to fill in this gap, it’s called the poet laureate. In Colorado, we’re grieving the passing of our poet laureate, Andrea Gibson. The poet laureate gets funding from the state to do all kinds of poetry programming and advocacy. But this funding is small and fickle (especially now). So we created a book that does two important jobs:

1) It is the first anthology of Colorado’s state poets laureate, the second oldest state poet laureate in the US dating back more than 100 years

2) Profits from book sales will go to create an endowment for the Colorado poet laureate, strengthening and sustaining the position into the future. Funding will go to allow the poet laureate to do poetry programming in rural and low income areas that are often missed due to funding constraints.

Pre order the book

How big is the solar system? If you created a sun the size of a small car, earth would be the size of a quarter, 263 yards away. From a young age I have been fascinated by outer space. Two years ago, I had the idea to create a to-scale model of the solar system along the Animas River Trail in my town of Durango, Colorado. Thanks to our city’s new Lodgers Tax Arts and Culture Fund, which wisely invests hundreds of thousands per year into creative projects annually, I was awarded a grant to do something I had zero experience in: create a large-scale permanent public art installation. I teamed up with a dozen local artists and businesses, and we created The Durango Solar System, a highly collaborative public art project that features to-scale sculptures of the sun and planets along 6 miles of our beloved river trail. This isn’t the only to-scale model of the solar system, but it might be the most funky and fun. It’s perfectly Durango, and I’m honored to have worked with so many talented people who made it happen.

After two years of navigating city policy, permitting, funding, and the challenges of working with over a dozen artists, the Durango Solar System is getting installed right now. Upon completion we’ll host a community bike ride to visit all the installations (during which we’ll be traveling much faster than the speed of light through its derived space…).

The documentary that my brother, Cam, and I released earlier this year has now traveled to five film festivals and a handful of other screenings. We won the audience choice award for best documentary short at the Durango Independent Film Festival. I wrote about the incredible experience of making a film in a recent article.

After 10 months on tour, we are winding down our festival circuit by returning to our home town at the Denver Film Festival in November. I hope to see you there.

Film Website

Feel free to forward this newsletter to someone who might be interested in one of these projects.

In late 2022, my brother Cam invited me to join him in making his first documentary film. I was leaving my job as founding-CEO of Upcycled Food Association after four years of gratifyingly and terrifyingly hard work. With zero experience in filmmaking, and a desire to do something totally different, I accepted.

Cam called me because he needed help with the business side of filmmaking, and having founded four organizations over the proceeding 12 years, we assumed that enough of my fundraising, project management, and leadership skills from starting businesses would translate into making movies.

Cam had been working in the TV industry for a long time, editing shows on the Discovery Channel and Food Network like Diners Drive-Thrus and Dives. During his tenure, Triple D picked up seven Emmy nominations (or was it eight?). He is a skilled editor. Watching him click and tap at his computer on video editing software is mesmerizing. He's able to transform disorganized raw footage into an entertaining story in seconds. It's a wonder to watch, like observing a seasoned cook dance through the kitchen. But Cam had never made a documentary, which we soon came to learn, involves skills other than expert-level film editing.

Creating a film takes complex project management, fundraising, community development, marketing, and most importantly, storytelling. That last one, storytelling, would prove to be one of the most humbling challenges of our careers.

The film was based on a historic outdoor feat, documenting the journey of the first crossing of Colorado on skis in 1978. We caught wind of the story when a family friend happened upon an event by the Colorado Mountain Club where one of the expeditioners, now in his mid-80s, recounted the journey to a small audience by flipping through 35mm film photographs and reading a scripted account of the adventure.

Three amateurs from Boulder skied 490 miles across Colorado on makeshift gear, did not get buried in an avalanche, and amazingly, did not see a single person in the backcountry the entire way. Their route helped inspire the design of the famed Colorado Trail, then under early construction, and the locations of the 10th Mountain Division Hut system. This was a story from the backcountry of Colorado, before backcountry skiing was a thing, less than a decade after I-70 gave the masses access to the mountains. These skiers had set out to find a new route across the mountains, but what they found instead was a totally new outlook on life, work, and unexpectedly, art.

Someone who had attended the Colorado Mountain Club presentation fatefully called Cam. "This story is good. It deserves more than a powerpoint presentation."

"This will be easy," we thought. Film an interview with the skiers who did the expedition, get some rad drone footage of the Colorado mountains, spend a couple months stitching it into a film, and go win an award at a film festival. Easy.

I'm sorry to say that it was not easy. What we thought would take six months would take thirty.

The expedition’s ringleader, Alex Drummond, was living in a senior center in Boulder. At our first meeting, he brought a backpack filled with immaculate documentation of the 490 mile route, a copy of his published biography of Enos Mills, and hundreds of photographs from along the journey. He also brought hundreds of pages of self-written poetry, including many inspired by the expedition.

The second skier was an eccentric artist named John King, living in Lyons, Colorado, 30 minutes from Boulder. Arriving at his home, we were surrounded by dozens of massive kinetic sculptures, giant flowery metal contraptions that spun in the wind and oscillated when touched. Our interview reminded me of how it must have been for journalists to visit Ram Das in his later years.

The third and final skier, Peter Vanderwall, was a wayward mystic that John and Alex hadn't seen or heard from since completing the expedition in 1978, 45 years prior.

That summer was spent driving around Colorado in Cam’s 2003 Honda Element, recording interviews, sometimes skiing miles into the mountains to capture a few seconds of film from the exact vantage point of one of the original photographs. At one point, we had to re-film an entire three-hour interview after accidentally recording it in time lapse mode on our first attempt. It was a gritty, chaotic, truly amateur filmmaking exercise not unlike the floundering first few months of starting a business.

We started a crowdfunding campaign, which ultimately raised about $30k to finish production, pay Cam his hourly rate for post-production, and distribute the film through film festivals. We built out a communications plan, maintaining an email list and social media presence. We developed relationships with partners, journalists and brands who donated gear for us to raffle off at fundraising events. We created an advisory board of directors, producers and editors to give us feedback on our strategy. All of it felt surprisingly familiar to starting a nonprofit or social enterprise.

But when it came time to start building the story, a creative muscle I hadn't toned began being torqued in uncomfortable ways. We knew we didn't want to tell the same old story that is so common in outdoor films: Three white men do something cool in the outdoors. They tried to do it. Then they did it. And in the end it was done. The End.

What if we told the story of how the route inspired the Colorado Trail? Great idea! We drove around the state multiple times to film the decedents of Gudy Gaskill, the matriarch of the CT who corresponded with the skiers from our expedition. But in the editing room, that story fell flat.

What if we told the story of how this expedition couldn't be done in today's age because of climate change? Another great idea! But when we started to mock up the storyboard, it was incongruent with the material we had filmed. Our story concepts were not true to the skiers and the esoteric, spiritual, seemingly psychedelic adventure that brought them closer to their inner most creative forces.

In entrepreneurship, the phase of finding product-market fit–the coherence between a business offering and the problem it is trying to solve in the market–is the critical, sometimes frustrating, foundation for a successful business. You can know deep in your soul that your business is amazing. But if it doesn’t match the needs of the market, it’s irrelevant. This process of deciding what specific story to tell was our product market fit challenge. We knew we had the potential for a good story, but it was hidden.

In the depths of our frustration, we stumbled across some previously unappreciated footage. The skiers seemed to believe their expedition was really just a massive landscape art installation, being the first people to physically draw a line in the snow along the continental divide. This concept of a moving line in the snow was a creative wellspring for them, ultimately leading to their pursuit of creativity and self-expression through poetry and sculpture for the rest of their lives.

Looking upon these aged faces reflecting on the most important accomplishment of their lives, toward the ends of their lives, and ruminating on the idea of the moving line, we were touched. Not only did this storyline resonate with a deep truth for our subjects, it filled a niche in the crowded outdoor documentary space. We spoke with lots of outdoor enthusiasts who agreed that some of their best ideas, most creative and inspiring moments, came while spending time in nature. But that idea of nature as creative inspiration wasn’t captured in other documentaries, leaving room for us to make a unique film. We finally had our story. And we were invigorated to tell it.

Cam and I were living together in Durango, and our adjacent home offices lent themselves to impromptu meetings when we’d obsess over little details in the post-production process. We set meeting agendas, met regularly, assigned roles, and checked in on progress daily. We were essentially running an organization whose mission was to do justice to our story.

After months of editing and storyboarding, pitching each other on scenes and motifs like Hollywood producers, we had a finished product. Twenty eight minutes of pure gold. We had our film. And it was brilliant.

We sent the film out to our advisors to ask for feedback. The consensus was clear: this film is bad. Or, in their words, it needed some “significant work.” The introduction was too slow, the story disjointed and boring, and who are these random characters that come out of nowhere in the middle of the film? "It feels bad," said one advisor.

The wind in our sails eddied and we were alone in a creative purgatory. The edits they were suggesting amounted to a full overhaul of the film. To make matters worse, we were broke.

Cam had poured everything into this film, working on it full time for months instead of taking on paying clients. I was in the process of starting a new organization myself, I wasn't able to contribute as much energy as I had at the beginning, let alone money. Now, instead of being at the end of the process, nearing the time when Cam would be able to start earning an income again, we were back at the starting line. It was incredibly disheartening. We faced the reality that entrepreneurs always face: this is going to take much longer than we had hoped.

We had already been working on the film for a year, and it would be another year of arduous effort, Cam tapping away at his computer, making minute edits to footage we had by then reviewed hundreds of times, and myself trying to keep our supporters excited about the film despite delays.

Finally, in October 2024, two years after the project began, we finally had a film that we loved and our advisors approved of. It was time to start sharing it with the world.

Applying for film festivals is a lot like applying for grants. You put in the work to establish a relationship with the festival leaders, you develop a compelling application, and then wait around with dreams of winning an Oscar only for them to likely decline your submission.

We applied to a handful of festivals, and then another handful, putting the application fees on our credit cards and hoping that one day we'd get the money back after the film succeeded on the festival circuit and got purchased by an online streaming service.

Miraculously, we got some early wins, making it into the Colorado Environmental Film Festival, The Santa Fe Film Festival, and the Durango Independent Film Festival. We added the laurels to our film poster, and set out to share Moving Line with the world.

The first festival screening was near our hometown of Denver, so we invited friends and family and expected that a handful would show up. Instead, our family flew in from out of state, and countless friends from elementary school, college, work, virtually every phase of life came out and filled the screening room to the brim.

After the screening we got on stage with our guests of honor, the skiers from the 1978 expedition, and spent thirty minutes fielding enthusiastic questions from friends and strangers about the film. Looking across the faces of the skiers on stage, in their late 70s and 80s, I was struck by how gratified they were to share one of the most important moments of their lives with the world. I was overcome by emotion and thought I would cry on stage. What an amazing honor it is, and an immense responsibility, to tell a person’s story.

I have been pretty public facing in my roles as an organizational leader for over a decade. It feels comfortable for me to hold a microphone in front of an audience and “rah, rah” try to get people excited about what I’m building. But the experience of sharing our film felt totally different. I wasn’t just sharing about a new solution to one of the world’s problems. I was exposing my creative soul. It was scary. But in daring to open myself to the critique of my innermost creative force, it became one of the most gratifying experiences of my life.

Since the premiere, I have been trying to answer this question: Why does it feel so different to share a creative project than to share any other entrepreneurial venture?

I think there is something special about the creative process that requires an increased vulnerability. Yes it's vulnerable to start a business–to put yourself out on a limb and ask for money from a stranger to support your mission, to wade through the confusing, discouraging, disorienting entrepreneurial process. But to let our inner creative light shine through our walls and out into the world, carrying all our insecurities with it, is one of the most vulnerable things a human can do. And as Breneé Brown reminds us, the greater vulnerability we express, the greater risk we take in exposing our anxious little hearts, the greater love we can feel.

I had received applause on stage many times after presenting about my entrepreneurial endeavours. But when the audience clapped after our film, it was a different sort of applause, one I had never been on the receiving end of. It had a distinct flavor. The sound of it was different. I suddenly realized how someone might get addicted to this applause. To lay one’s creative guts to bear, and then amidst the risk of being battered, be held.

Leaving the stage I shook hands with the misty-eyed skiers, but I felt I should have bowed.

So, is making a film the same as making a social enterprise? If a social enterprise is just a business that makes the world a better place, then perhaps no. But if a social enterprise is something more, an outlet for us all to expose our creative selves to the world, to open our hearts and accept the barrage of criticism or gratification or whatever might ensue–but finding meaning in the sharing regardless–then perhaps, yes.

Moving Line won the audience choice award at the Durango Independent Film Festival, and screened on PBS for Earth Day. We are still hoping to get the film into more festivals and get it picked up by an online streaming service.

Trailer