Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: Rules of Thumb

This fall, a local high school senior reached out to me as part of his mentorship class, and we’ll spend an hour or two a week together, for the next 10 weeks.

When thinking about the topics we’ll explore, it made me wonder if things have changed since I was choosing a college and starting to explore career possibilities. For some reason, I got to thinking about our country, and the old cultural mantra, “you can make it if you try.” Do young people still believe that? And what does that really mean in the AI age?

My belief is that our culture continues to move the goalposts on the definition of “making it,” and there are ongoing concerns around conventional careers and college, both regarding declining reading levels in schools and stagnant employment for recent grads.

While I don’t know the new rules of the game, or if they have changed, I plan to focus on the things that I believe are unchanged in this new era: self-discovery, relationships, exposure to new ideas, intentionality and goal-setting.

Borrowed Wisdom: Harold Bloom

One of my favorite achievements of non-fiction literature can be found in a lesser known book by the late Yale Professor Harold Bloom. In his 2004 book Where Shall Wisdom Be Found, Bloom explores insights from various schools of wisdom: The Hebrews, Greeks, Shakespeare, Cervantes, Emerson and more. Something I think is so brilliant about Bloom's work is that he lays the foundation for the book using the stories of Ecclesiastes and Job, highlighting that (1) without a soul, life is meaningless and (2) there will be some things in life that we won't fully understand.

Reading, Watching, Listening: Poem by Rumi (13th Century, translated by Coleman Barks)

Little by little, wean yourself
This is the gist of what I have to say.

From an embryo, whose nourishment comes in the blood,
move to an infant drinking milk,
to a child on solid food,
to a searcher after wisdom,
to a hunter of more invisible game.

Think how it is to have a conversation with an embryo.
You might say, “The world outside is vast and intricate.
There are wheatfields and mountain passes,
and orchards in bloom.

At night there are millions of galaxies, and in sunlight
the beauty of friends dancing at a wedding.”

You ask the embryo why he, or she, stays cooped up
in the dark with eyes closed.

Listen to the answer.

There is no “other world.”
I only know what I’ve experienced.
You must be hallucinating.

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: Life Rewards Focus

It seems that optionality is rewarded in youth, and focus is rewarded with age. In truth, life always rewards focus, it just gets clearer over time.

Big Idea: Conflicting Truths

My working definition of wisdom is the ability to hold conflicting truths in your hands at the same time, and still move forward.

There are endless scenarios where we have to rely on judgment.

I think the most zoomed-out version is our own lives.

It’s powerful to recognize simultaneously both the importance and the insignificance of our individual life experiences.

In so many respects, our lives matter immensely, even if it’s just to a small group of people.

And at the same time, we must recognize our utter smallness compared to space and time.

I think about this often. When I'm in a meaningful one-on-one conversation, I'll say to myself, 'wow, we're really doing something here.' It reminds me of an excerpt from Bessie Anderson Stanley's poem on success (often misattributed to Emerson): “to know even one life has breathed easier because you have lived, that is to have succeeded."

There is power and comfort in both of these, especially when held simultaneously.

Borrowed Wisdom: Renoir’s Last Words

Legend has it that the final words from French Impressionist master painter Pierre-Auguste Renoir came at age 78 in 1919, after he finished painting a small bouquet of flowers.

He said “I think I’m beginning to learn something about it,” then simply “flowers.”

To me, this story about Renoir is such an inspiration and a masterclass in humility and wonder, a reminder that the lessons in life take a full life to learn.

Reading, Watching, Listening: Scott Galloway

Author, professor and entrepreneur Scott Galloway does not pull punches, and he and his team have proven to be great data aggregators and researchers. Since 2024, Scott has published a series of essays, videos and posts entitled “America’s War on The Young.” They are thought-provoking pieces about our country’s demographics, socio-economy and a changing American Dream. Here are a few of them.

• Essay

• TED Talk

• Post

Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

This is the eighth edition of this newsletter. When I started playing with this format, I committed to eight weeks. I definitely have enjoyed the weekly output, although I’m considering the path forward, both whether to continue or not, and updates to the format. I’m considering include reducing the newsletter into three short sections or pivoting to a short weekly passage on one idea. If you have any thoughts about the content or format that have worked well, or could be improved, definitely let me know.

Top of Mind: Disproportionate Value

A common human pitfall is the attempt to try to get disproportionate value from things that were never meant to provide it.

Big Idea: Practical Spirituality

If you were to ask a Buddhist what they thought about the origin of the universe, they might say that they don’t give it much thought, because the origin of the universe doesn’t change the reality of the present.

We can be so focused on whether something is true that we overlook the simpler reality that spirituality is the most practical way to live.

Jordan Peterson would ask, “in a world where you can choose meaning or meaninglessness, why would you settle?”

What practical benefit is there to abandoning any of the following beliefs?

• that things happen for a reason

• that we are put into circumstances in life for the purpose of growth and transcendence

• that there is a divine spark within our parents, siblings, friends, or any life form

• that the actions we take matter, and that we ought to take ownership over our experience

• that it’s safe to operate with an underlying sense of trust

I believe the underlying principles of religion and spirituality are true, and it’s deeply fulfilling to feel that at a somatic level in addition to thinking it. But I also believe much of life is giving up our default sense of control and adopting a set of empowering beliefs that support our ability to navigate and thrive in our daily lives.

Borrowed Wisdom: On Society and Consumerism

Italian poet and writer Pier Paolo Pasolini in 1975: “no fascist centralism managed to do what the centralism of consumer civilization has done”

Comedian Keith Lowell Jensen in 2014: “what Orwell failed to predict is that we’d buy the cameras ourselves, and that our biggest fear would be that nobody was watching”

Reading, Watching, Listening: “Tony”

With the release of the new Anthony Bourdain biopic, Tony, there have been a lot of different outlets publishing pieces on the life and work of Anthony Bourdain. I listened to a Bourdain themed episode on The Watch and read a NYT Magazine piece called “The Gospel According to Anthony Bourdain”. In both, there are a lot of fun stories that inspire wonder, which is what Bourdain did best, and exploration of the broader cultural impact of his life.

Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: Keeping Things Light

Something that is a constant practice is reminding myself to “stop taking things that are supposed to be fun, and finding ways to make them stressful”.

Big Idea: Defining Love

Last week I had a wonderful coffee meeting with a long-time mentor and friend. We often find ourselves trying to define the indefinable, and this week we were talking about love.

I thought back to an article I wrote a few years ago called Love and Alignment about the people in our lives over different seasons of life.

For purposes of this exploration, I believe love can be defined as is simply wanting the best for someone or something.

I like this definition because it’s sufficiently broad. It’s an act of love to take yourself to the gym. It’s an act of love to pursue a promotion that allows you to lead better and differently. It’s an act of love to tend to a garden, or to have a hard conversation that inspires growth in another.

When I think of love, I also think of the importance of capacity. As we increase our capacity, a process that I describe as emotional-spiritual growth, it gives us the opportunity to love more things.

For example, with increased capacity comes a greater comfort with self and underlying sense of trust, which gives you greater ability to be happy for more people rather than experience emotions such as envy, jealousy or greed, which can be inspired by the same stimulus, depending on the state and capacity of the receiver.

Borrowed Wisdom: Richard Feynman

Richard Feynman is one of the most brilliant theoretical physicists and intuitive thinkers of the 20th century. His advice on living: “Fall in love with some activity, and do it! Nobody ever figures out what life is all about, and it doesn’t matter. Explore the world. Nearly everything is really interesting if you go into it deeply enough. Work as hard and as much as you want to on the things you like to do the best. Don’t think about what you want to be, but what you want to do. Keep up some kind of a minimum with other things so that society doesn’t stop you from doing anything at all.”

Reading, Watching, Listening: Italian Cinema

Over the years, I’ve come to appreciate Italian films because I feel they capture themes of beauty, nostalgia and seasons, better than most. If you can put up with subtitles, here are a few of my favorites.

• La Dolce Vita by Federico Fellini (1960) - 95% on Rotten Tomatoes, 4/4 stars from Roger Ebert

• Cinema Paradiso by Giuseppe Tornatore (1988) - 90% on Rotten Tomatoes, 3.5/4 stars from Roger Ebert

• The Great Beauty by Paolo Sorrentino (2013) - 91% on Rotten Tomatoes, 4/4 stars from RogerEbert.com (reviewed after Roger’s death)

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: Predicting the Future

One of my mentors used to say: “if you want to predict the future, pay very close attention to what you are attached to.”

I like this as a reminder to help identify where in life I am too attached to an individual outcome, and have an opportunity to hold things a little looser.

Big Idea: Souls Between Lives and Uncertainty

A picture that comes into my head periodically is a scene of two souls, both between lives, speaking to one another.

I am not sure what form they would take, or what a soul would look like, but I think about a conversation they might have about making the decision to enter the world as a human, with all the uncertainty that comes with it.

It’s remarkable that of all the lives we could live, we end up with the one we have. It’s an idea I’ve found sparks a lot of gratitude and wonder for this experience.

Borrowed Wisdom: Right Place, Right Time

In the prologue of Scott Anderson’s Lawrence in Arabia, he includes this quote: “History is often the tale of small moments—chance encounters or casual decisions or sheer coincidence—that seem of little consequence at the time, but somehow fuse with other small moments to produce something momentous, the proverbial flapping of a butterfly’s wings that triggers a hurricane.”

It’s amazing what role chance can play in a life experience. For T.E. Lawrence, of Lawrence of Arabia, it was an example of a British guy who had a particular depth of knowledge of the Middle East, at a time when there was a war in the region and a need for someone with such knowledge, which otherwise would have been largely useless. With a background as a scholar, Lawrence became a great military leader and was instrumental in shaping the modern Middle East.

It reminds me of the key formula from Malcolm Gladwell’s Outliers as I understand it: success = hard work (i.e. 10,000 hours) x opportunity.

Reading, Watching, Listening:

Kiss Me Like A Stranger: My Search for Love and Art by Gene Wilder - This is one of the most honest books capturing one man reflecting on his own life, and a lot of fun to read given Wilder's sense of humor and personality. Most know about Wilder's on-screen success. But few, particularly younger people, know about his personal journey, including being married four times. While by conventional standards this seems like a failure in relationships, what I find so refreshing about Gene's experience is how he writes that it wasn't until later in life, and on his fourth marriage, that he really understood love. That's moving to me as a counter to our society that wants to figure out life by 20, 25, 30, 40 and certainly by 50. Gene is a reminder that perhaps life is long because it takes a long time to learn the lessons that we're here to learn, and maybe it will be later in life when the big ideas really click.

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: AI and Intuition

I’ve been thinking a lot about answer platforms. With LLMs and AI, we have more answers than ever. But does it really solve anything?

I think about a high school student analyzing their college or life design decisions. No doubt, AI will be able to provide answers, but without discernment, one might forget to question whether the machine is offering a useful answer.

AI often reverts to the mean. It’s good at making things rational and average.

Psychiatrist and philosopher Iain McGilchrist talks about left brain dominant cultures, and how they lead to hyper-rationalism and reductionism. He goes on to say that “mentally ill individuals attempt to reduce areas where a normal person would rely on intuition, feeling, and instinct to a graph or equation.”

Across human history and the great myths across civilizations, there are stories that celebrate intuition: someone, perhaps a hero, acting without complete information and trusting their gut.

As we outsource more of our thinking and decisions to LLMs, will we lose the muscle memory around intuition, and what is the impact at a generational level?

Big Idea: The Meaning of Life

I have spent a disproportionate amount of time exploring meaning. As part of that, I have asked many mentors about what they think about the meaning and purpose of life. Here are a few examples I’ve heard:

• The purpose of life is to go through it.

• The purpose of life is to learn the soul lessons that cross your path.

• The purpose of life is to work to bridge the world as it is with the world as it should be.

I think all of these are fair. When I think about the meaning and purpose of life through the lens of a human, it’s important to remember that humans have a unique ability to wonder. A good friend of mine often talks about the model that suggests our brain evolved this way. The reptilian brain is wired to survive, the mammalian brain is driven to love, and the human brain (i.e. the higher self) is driven to wonder.

So when I think about the meaning of life, the best definition I’ve come up with to date is:

To dream the perfect dream, and work to make it a reality…

With a few caveats:

First, everyone’s dream will be different.

Second, to truly be meaningful, the dream should be big enough to serve a larger population than just the self or a person’s ego.

Third, the original definition of perfect did not mean free of all defects. It meant complete, mature, whole, or in the Hebrew sense of the word shalom, the root of which points to the world “as it should be”.

In my current definition, I believe we need to revert to the original definition of perfect, because the wisdom to recognize that there are some things in life that we won’t understand, and the acceptance of the surprising, the unknown, and the beauty that comes from knowing the world is complete and perfect as it is, and has the ability to continue to evolve and grow, are primary ingredients of meaning and purpose.

Borrowed Wisdom: The Change Formula

So much of life is a process of enacting change, whether in our personal lives, relationships or careers. I was recently reflecting on my conversation with Diana Chapman, co-founder of the Conscious Leadership Group and co-author of The 15 Commitments of Conscious Leadership.

One of the concepts in her book is the “change formula”, originally developed by Beckhard and Harris:

(Vision x Dissatisfaction) + First Steps > Resistance = Change

During our conversation, I asked Diana whether people are more motivated by a compelling vision or from dissatisfaction. Diana confirmed that more often people are driven by dissatisfaction, akin to the idea of being “sick and tired of being sick and tired”.

The concept of resistance makes sense. Whenever we aim to change, there will be inertia, and our efforts must be greater than that resistance (for more on resistance, see the episode we did with the legendary author Steven Pressfield).

To me, what stands out is dissatisfaction. Especially in our culture that promotes acceptance and gratitude, both of which are incredibly important to a fulfilling life, I think we can underappreciate how adverse feelings like dissatisfaction serve a purpose, and can drive change in specific arenas or seasons of our lives.

Reading, Watching, Listening:

Instructions Before Visiting Earth by James McCrae - When I read this poem, I think about the idea of being “in this world, but not of it”, or a concept that my mentor calls “the ocean and the wave”. This is one of the best poems I’ve found to capture the strange and profound nature of the human experience, and what may be really going on at a deeper and spiritual level.

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I’ve encountered through books, other media, and my network.

Top of Mind: The Power of Coffee

I’ve been thinking about the power of coffee. One some days, the power that 2 ounces of liquid can have is pretty crazy. In Michael Pollan’s book This Is Your Mind on Plants, he asserts that from an evolutionary sense, we didn’t domesticate coffee, coffee domesticated us.

Big Idea: Career Leverage

Most people consciously or subconsciously assign values to different parts of their lives.

For work, I find that many people define their primary work value as freedom. People want a job that they somewhat enjoy, that somewhat ties back to their larger purpose, and provides for their life in some combination of money, time and fulfillment.

As I approach mid-career, and think about the role that career plays in broader life design, I have been playing with a concept that I call “career leverage”.

I believe career leverage is the way to get to the ideal combination of money, time and fulfillment.

Leverage = Credibility x Relationships x Ownership

• Credibility - Experience and training that creates a unique value proposition that addresses a need in the marketplace. Years of experience, results you can point to, big name affiliations that provide street cred.

• Relationships - Channels of distribution such as a network within a particular place or community where people think of you and associate you with offering a particular solution. The community can be as small as the company you work within. At the end of the day, it’s great to know the right people, but it’s better if the right people know you.

• Ownership - This is essentially a platform to operate. It might be your own venture, or a senior role at an existing company where you own certain relationships. You need a place and platform to deliver the service that are driven by your credibility and relationships.

These elements are multipliers because they amplify each other. If you had credibility, but no one knew you and you didn’t have a platform, you wouldn’t have much leverage. It would be like being the best painter in the world in a cave.

Career leverage can come in many different forms. There are plenty of vehicles such as law firms, accounting firms, financial institutions that if you stick it out you will end up with career leverage. There are also other ways to accumulate leverage, such as differentiating experience and combination of skills that offer a unique perspective, network or offering. When I think about the second path, I think about the episode we did with Mike Ablon and his concept of “Master Craftsmanship”.

Borrowed Wisdom: Ralph Waldo Emerson

One of the first books I really dug into in adulthood was Self-Reliance and Other Essays by Ralph Waldo Emerson. Many people may be familiar with the title piece Self-Reliance, but there were several other great essays including Experience, History, The Over-Soul, and Friendship. It’s a fun look into the mind of a great thinker and his thoughts on a variety of topics.

What I find so interesting is that despite living in a very different time, he captures so clearly timeless truths around the power of the mind to pull us out of the present, and the role of action and values in creating meaning.

Here are some of my favorite excerpts from this volume:

• "Nothing can bring you peace but yourself. Nothing can bring you peace but the triumph of principles." (Self-Reliance)

• "Travelling is a fool's paradise. Our first journeys discover to us the indifference of places. At home I dream that at Naples, at Rome, I can be intoxicated with beauty, and lose my sadness. I pack my trunk, embrace my friends, embark on the sea, and at last wake up in Naples, and there beside me is the stern fact, the sad self, unrelenting, identical, that I fled from. I seek the Vatican, and the palaces. I affect to be intoxicated with sights and suggestions, but I am not intoxicated. My giant goes with me wherever I go." (Self-Reliance)

• "Every ship is a romantic object, except that we sail in. Embark, and the romance quits our vessel, and hangs on every other sail in the horizon." (Experience)

• "Of what use is genius, if the organ is too convex or too concave, and cannot find a focal distance within the actual horizon of human life?" (Experience)

Reading, Watching, Listening:

The Score: How to Stop Playing Somebody Else’s Game by C. Thi Nguyen. I found this book through Daniel Pink’s newsletter, and have been enjoying it. The author is a philosopher at University of Utah who studies games and data. Essentially, Nguyen outlines that games are interesting because there is an objective in each game (i.e. usually to win) but it is different than the purpose (e.g. learning, fun, growth), and that games present an opportunity for each of us to create our own scoreboard for our lives (i.e. values) and hold our aims, goals and desires more loosely, as separate from our true purpose.

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday. Each week I share some thought-provoking insights of my own, along with wisdom from the great thinkers I've encountered through books, other media, and my network.

Top of Mind: Defining Adulthood

A definition of adulthood I’ve been playing around with: adulthood is when the things you never thought would happen to you, happen to you.

I see this as a continuous shift from theoretical to lived wisdom, both through my own life and through what I see in others and the world.

There are a lot of things that are hard to fathom when you're younger, that only make sense once you, or the people in your life, find yourselves in certain scenarios.

Big Idea: Great things are often simple but tough to replicate

A lot of the greatness we experience in life is simple, but not easy. The idea of pursuing a craft or way of being that is simple but tough to replicate is something worth striving for.

A few examples come to mind:

• Erling Haaland’s regimen for peak performance is fairly simple: a healthy diet, good sleep and intense exercise. When you watch Erling Haaland on an exercise bike say “Do I want to do this? No, I don’t. Will I do it? Yeah. Am I doing it? Yeah. Because why not? ... It’s good for my body, it’s good for my mind”, it’s easy to understand the role of this mindset through the greatness, but it’s still hard to do consistently.

• The other day, my girlfriend and I were at Bufalina in Austin. They have a fantastic cavatelli, and they tell you, right on the menu, what’s in it: heirloom tomato, ricotta salata, tomato water. Even though we know the ingredients, and they’re incredibly simple, it’s hard to go home and recreate the dish.

• The founder of the clothing brand Husbands, Nicolas Gabard, talks about craft and imitation on the Throwing Fits podcast (minute 46): "you can copy the result, but you cannot copy the process." It took him years to get the button placement right on a double-breasted jacket, and he points out that anyone could put the button in the same spot, but they still won't understand why it goes there. That's what makes the difference.

• Finally, there’s Picasso’s Le Taureau, in which, over the course of a month, he distilled a bull into its purest, simplest form. Fernand Mourlot, the master printer who worked with him on the series, commented that “in order to achieve his pure and linear rendering of the bull, he had to pass through all of the intermediary stages.”

  

As I think about the throughline across these examples, I think back to when I interviewed James Kerr, author of Legacy: What The All Blacks Can Teach Us About The Business Of Life, he talked about the countercultural nature of success:

“Success is countercultural. Not doing what everybody is doing is a pretty good way to be outstanding. Literally you stand out.”

In many cases, the things that make the difference are the easy things: easy to do, and easy not to do.

Borrowed Wisdom: Abraham Joshua Heschel

Abraham Joshua Heschel was a Polish-American rabbi known for his profound writings on mysticism and marching alongside Martin Luther King during the civil rights movement. As far as I understand it, this guy was really wise, and really felt the spirit. To give you a sense, he’s the one who said, after marching with MLK at Selma, that he felt “his legs were praying”, and one of the main biographies about him is titled A Life of Radical Amazement.

Here are a few ideas from Heschel that have stuck with me and stand on their own, no commentary necessary (some are honest paraphrases from my notes):

1. Wonder: “The beginning of awe is wonder, and the beginning of wisdom is awe. Wonder precedes wisdom.”

2. Creativity: “The creative man is he who succeeds in capturing the exceptional and instantaneous before it becomes stagnant in his mind.”

3. Freedom: “Freedom does not mean the right to live as we please, it means the power to live spiritually, to transcend our nature and rise to a higher level of existence.”

4. Faith: “One must take a leap of action rather than a leap of thought. We are asked to surpass our own needs, to do more than what we understand, in order to understand more than we do.”

Reading, Watching, Listening:

Same as Ever: A Guide to What Never Changes by Morgan Housel. I was excited to come across this book, and surprised I'd never heard of it. It's a series of stories about the enduring nature of the human experience. I found it timely given where the country is right now. With AI reshaping the job market, it feels like things are going to be permanently changed. Housel's concepts have been an important reminder and a welcome recentering, anchored in a longer time horizon.

Let me know if anything stands out. Hope you have a great week.

Adam

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Happy Tuesday.

Top of Mind: More Gratitude

Earlier this week I caught up with a friend in his early 70s. He and his wife have no living parents, and no grandchildren. He mentioned the grandchildren part might seem sad, but commented on many things about their experience that are positive and freeing. It reminded me of something he shared with me once that his father would say: "If you can't afford a steak, eat a burger." It's easy, at least for me, to be so focused on my ideal scenario or outcomes that I forget about the good stuff that's already present. There are many ways, and endless circumstances, to be happy.

Big Idea: Free Will vs. Destiny

Years ago, I took the opportunity to ask an honest question to a well-known spiritual teacher.

I asked him a two-parter: “How do you think about free will vs. destiny, and separately, how do you think about our role in pursuing the things we want in life, whether that’s love, success, purpose or the divine, vs. the potential reality that the things we want in life are actually pursuing us?”

His answer: “First, let’s agree that there is some level of determinism, as evidenced by the fact that we didn’t choose our parents on a conscious level, so there are at least some things that happen that seem predetermined. The problem is that we don’t know if it’s 1% or 100%, but we have the perception of free will, so our job is to honor that perception and use it.

When you are setting out, take responsibility for your life as if it’s based on free will, and when you are looking back, accept that what happened as meant to be.

Now in regard to the search for all the things we want in life. We must go out with an intention, but we also must have a level of openness to receiving the things that are trying to come in.”

Borrowed Wisdom: The Beauty of Ripe Fruit

When I think about all the books I've read or concepts I've explored, I can trace a lot of them back to a spark that Marcus Aurelius's Meditations lit in me circa 2013. Lots has been written about the book, since it's an inside view into the mind of the richest and most powerful living person of his time.

When I think back on the book, I always return to an overlooked comment about the beauty of ripe fruit. Aurelius’s comment always leaves me wondering whether the beauty comes from the fruit being in its prime state for consumption, or from the reality that tomorrow the same fruit will be rotten.

Like most either/or questions, the answer is undoubtedly both. However, I believe the brilliance of the question is that it brings to our attention how often we overlook one or the other: so focused on something being rich in the present, or on the tenderness that this present will pass, or, most commonly, missing both altogether.

Here is the actual passage: "We ought to observe also that even the things which follow after the things which are produced according to nature contain something pleasing and attractive. For instance, when bread is baked some parts are split at the surface, and these parts which thus open, and have a certain fashion contrary to the purpose of the baker's art, are beautiful in a manner, and in a peculiar way excite a desire for eating. And again, figs, when they are quite ripe, gape open; and in the ripe olives the very circumstance of their being near to rottenness adds a peculiar beauty to the fruit."

Reading, Watching, Listening:

Reading: Monet Refuses the Operation: A poem by Lisel Mueller, from her collection Second Language (1986). I find myself coming back to it a few times a year. It took me six or so readings for it to click, and for me it has the qualities of a great music album, in that over time I’ve come to appreciate different elements of its greatness. I’ll let you come to your own conclusions and appreciations if it speaks to you.

Let me know if anything stands out. Hope you have a great week.

Adam

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I feel best when I am learning, creating and sharing, and I’ve been thinking about how to lower the bar when it comes to creation. In response to my growing stack of unfinished and unpublished longer form writing and podcast projects, I’m thinking that maybe the answer is simply to start smaller and share.

Top of Mind

• Presence & Gratitude - Every once in a while I have a realization that makes me feel simultaneously enlightened, and a bit sheepish. Perhaps like many others, I can be guilty of comparing my life to the most extreme idealistic scenarios I can imagine. Not shockingly, this causes quite the spiral, and the goalpost always moves. I’ve been trying to lean into simple practices of presence and gratitude as a foundational state, and needless to say have been enjoying it. If only there were volumes of texts about this concept…

  

  A fun reminder from 19 Cleveland, an excellent Telavivian restaurant on the border of the SoHo & Nolita neighborhoods in NYC.

Big Idea

• Beauty & Luxury - With the rise of aspirational lifestyles through social media and the K-shaped economy, I’ve been playing with an idea that the concepts of beauty and luxury are being inappropriately merged. What I mean by that is there’s an idea being promoted that in order for something to be worthwhile, it must be luxurious. Of course, many luxurious things are beautiful. However, a lot of things that are celebrated and known to be luxurious, such as excess consumption and vanity, often aren’t beautiful at all. In my own life, many of my most beautiful moments weren’t luxurious, but rather pulled at much simpler, deeper and more universal elements of the human experience. Especially with the proliferation of cultural ideals through the megaphones of social media, I predict a cultural re-wiring will be necessary over the coming years or decades, but maybe this is nothing new.

Borrowed Wisdom

• Lessons from Jim Rohn - I recently came across a few thought provoking ideas from the American entrepreneur, author, and motivational speaker Jim Rohn. Rohn describes the ingredients for a good life as (1) productivity, (2) friendship, (3) heritage and culture, and (4) experiences. If you watch this video clip I think you’ll agree that he nails it. Especially in our culture of external validation and comfort, productivity was the one that surprised me the most. It’s easy to think that a good life is circumstantial. However, I’ve been in many conversations with friends over the years, and experienced it myself, whereby everything is fine and going well, but there’s a sense that something is missing. For me, it’s usually about learning and growth, and sometimes I have to look to places outside my daily and weekly routines to get that. Rohn describes it as doing the things that are easy to do but also easy not to do. For me, these are things like making an effort to connect with friends or family, reading, sitting down at the keyboard, or lacing up my running shoes.

Reading, Watching, Listening

• Reading: The Leopard: This is known as one of the greatest Italian novels from the 20th century. It’s about a fading Sicilian family dynasty in the 1860s. I haven’t gotten to the lightbulb moment yet, but the characters, settings and scenarios have been pretty fun.

• Watching: Cinema Paradiso (Rotten Tomatoes: 90%): A classic Italian film from 1988, also set in Sicily, like The Leopard above. A beautiful movie about love and loss, and the stories we tell ourselves about the past.

• Listening: Streetwise: This is the new autobiography of Lloyd Blankfein, former CEO of Goldman Sachs. Lloyd grew up in the public housing projects of East New York, Brooklyn, and went on to attend Harvard, Harvard Law and ultimately to lead the pre-eminent investment bank. Lloyd's story is such a radical example of the American dream and economic mobility that seems increasingly less common today, and potentially at further risk given the ongoing socio-economic changes. The book follows a familiar modern autobiographical structure, similar to Danny Meyer's Setting the Table and Stephen Schwarzman's What It Takes.

Let me know if anything stands out. Grateful for the chance to create and share.

Adam

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Many companies set out to do something hard, Firefly Aerospace set out to do the impossible.

After 10 years and several existential moments, in 2025, Firefly became the first commercial company in human history to successfully land on the moon. Before Firefly, only countries had landed on the moon (for context, the Apollo program consumed roughly 4% of US GDP).

Following the landing, Firefly went public on the Nasdaq in the largest Aerospace & Defence IPO in history, with a valuation of roughly $8.5 billion.

Eric Salwan, one of the founders of Firefly, joined the show to discuss the Firefly journey, The New Space Race, and his own view on the power of pursuing the impossible.

Episode Highlights (90 Seconds - Full Episode Linked Above)

Top Takeaways

• The Firefly journey was part of Eric’s spiritual path. Firefly launched in 2014, ran out of money in 2016, and shut down. Eric had invested his own money, brought in family and friends as investors, and had to lay off the entire team. On New Year’s Day 2017, with no company and no clear path forward, he made the decision he was not leaving until someone physically removed him from the building. Firefly Aerospace relaunched May 1st, 2017 with 20 employees.

• There is a power to relentlessly sharing the vision, even with people who have no way to help you. When Firefly needed capital at its most desperate moment, two of Eric’s friends went to their networks and raised $170 million of a $175 million round. None of those investors knew Eric personally, but they trusted the people who made the introduction.

• People underestimate the personal cost of being a founder. Eric didn’t take a real vacation for nearly eight years. Firefly shut down once, had a rocket explode on the launch pad, watched tens of millions of dollars of work burn in a field during a test fire, and had to lay off 160 people who trusted the leadership to find a way. The Firefly story is an incredible one from the outside, but the lived experience was not always glamorous.

• We are in the very early innings of the new space race and the stakes are high. Eric walked through the key players and the orbital markets being created, and how competition between the US and China continues to grow. His frame: when the first ships landed in America, nobody could have predicted what would be built there 250 years later. Space is the next frontier.

Resources

• Eric Salwan on LinkedIn (best way to follow updates on the upcoming Firefly documentary)

• Firefly Aerospace Website

Full List of Topics Covered

• Eric’s background and how he came to co-found Firefly Aerospace

• The original founding of Firefly in 2014, the shutdown in 2016, and the decision to restart

• The capital requirements of building a rocket company

• NASA’s Commercial Lunar Payload Services program and how government contracts seeded the commercial space economy

• The personal toll of the founder journey, including layoffs, rockets exploding, and years without a real vacation

• How Firefly became the first commercial company in history to successfully land on the moon

• What the lunar landing felt like in the room when it happened

• How to think about the new space race and the roles of SpaceX, Rocket Lab, Firefly and others

• Big power competition and the militarization of cislunar space between the US and China

• Lessons Eric would share with students and young entrepreneurs

• The Firefly documentary coming to Amazon Prime

I hope you enjoy the conversation. Feel free to share and let me know what resonates with you in the comments.

– Adam

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When I set out a few years ago to create a show that explored leadership, meaning and purpose, it was episodes like this that I had in mind.

For those who aren't familiar. The All Blacks are the national rugby team of New Zealand, and are considered by many to be the world’s most successful team, maintaining a nearly 80% winning percentage over 120 seasons.

James Kerr is an international leadership speaker, performance coach, and the author of the bestselling book Legacy: What the New Zealand All Blacks Can Teach Us About the Business of Life.

James works with sports teams from The Premier League to F1, businesses from Wall Street firms to leading technology companies, as well as military units.

In this episode, we discuss leadership lessons from The All Blacks and other elite teams.

Episode Highlights (75 Seconds - Full Episode Linked Above)

Top Takeaways

• Success is always countercultural. Great teams and individuals standout as a result of doing something different, sometimes it is the simple and obvious things like showing up consistently, orienting towards service, lifting up others or playing the long game. In the episode, James paraphrased Anna Karenina “Dysfunctional teams are dysfunctional for all sorts of reasons, highly functional teams are highly functional for the same reasons”.

• The best teams whether in sport, cultural or business, have a shared identities, beliefs and a sense of belonging. The All Blacks for example, represent a nation and have a commitment to the team is bigger than the individual as captured in the players effort to “leave the jersey better than you found it”. When you look at great teams and cultures, they usually have a sense of a shared story, mission, vision, and values. James commented that “first we shape our story, and then our story shapes us”.

• Greatness often comes from humility and doing the little things right. The All Blacks have a practice of cleaning their own locker room after each game, known as “sweeping the sheds”. In each of our domains, there are things that seem small, that the true masters of the craft understand the importance.

• Meaning comes from the decision that something matters, then choosing to take responsibility for it, whether at your job, in your fitness routine or at home, there is a shift when you make a commitment to a particular thing and then own it. James gives the metaphor around levels of maturity and meaning being the number of keys on your keyring, representing the different things that you are responsible for or looking after.

• Emotional regulation is leadership. This has been a consistent theme throughout the 65+ episodes of the podcast. In order to lead others, we must lead ourselves, and in times of crisis, people often turn to the person that is the most calm. If we can’t regulate ourselves, then we risk repeating patterns and may lose the ability to lead ourselves or others forward.

Resources

• James Kerr LinkedIn

• Legacy: What the New Zealand All Blacks Can Teach Us About the Business of Life

Full List of Topics Covered

• Why the All Blacks are the most sustained high-performing team in history

• Culture versus talent in elite performance

• Identity, story, and belonging in leadership

• Humility and responsibility as cultural pillars

• Sweeping the sheds and servant leadership

• The haka as ritual, meaning, and psychological preparation

• Cohesion as a competitive advantage

• Self-regulation and calm under pressure

• Leadership as responsibility

• Culture built through teams

• Contribution, meaning, and legacy

• Long-term thinking in sport, business, and life

I hope you enjoy the conversation. Feel free to share and let me know what resonates with you in the comments.
– Adam

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Mike Ablon is the founder of Pegasus Ablon, a Dallas based real estate development firm behind the transformation of the Dallas Design District, and a former Dallas mayoral candidate.

Mike has spent his life striving to “build things that matter”, focusing on places where culture and commerce intersect, through a deep commitment to craftsman and long term thinking.

In this episode, we explore Mike’s counter cultural view of entrepreneurship, the ingredients for great cities, and how authenticity, neighborhoods, and talent migration will shape the future of American cities.

Episode Highlights (~60 seconds) | Full Episode Linked Above

Top Takeaways

1. Mike’s path to entrepreneurship came after decades of working with great real estate developers such as Robert Venturi, and he saw starting his own firm as the best way to continue his pursuit of becoming a master craftsman. I find this to be a refreshing view on entrepreneurship as our culture has become more and more fixated on founders, and anything less than that can be seen as playing small. Mike’s journey is a story of taking the long road and a focus on crafts.

2. Great cities are defined by distinctive neighborhoods, such as New York’s SoHo, West Village and Meatpacking District, and by their ability to support people through different seasons of life from early career, family formation, and later years.

3. Mike places a lot of emphasis on the space between the spaces, and how walkability is more than sidewalks, it’s how you feel when spending time in a particular area. People remember how a place makes them feel more than what buildings they were in or around, and they intuitively know which places are authentic versus manufactured. In the Dallas Design District, Mike implemented a “no nationals” policy so the neighborhood would be made up entirely of local stores and restaurants, preserving its creative character.

4. The future of cities will be shaped by talent migration. The old model was that people went where the jobs were. The new model is that talent goes where it wants to live, and the jobs follow. The cities that will win over the next 100 years will be the ones that create places people actually want to be part of, with real culture, character, and a sense of belonging.

Resources

• Mike Ablon LinkedIn

• Pegasus Ablon Website

Full List of Topics Covered

• Mike’s counter cultural view of entrepreneurship as a byproduct of craft

• Why founder identity is overrated and mastery is underrated

• The role of mentorship in becoming a master craftsman

• What actually makes a great city

• Why neighborhoods matter more than skylines

• The space between the spaces and why it defines urban life

• Authenticity versus manufactured development

• How Dallas evolved and what young cities can still become

• Experience economy versus ownership economy

• Density, walkability, and suburban urban cores

• Why talent now moves first and jobs follow

• What gives a city soul

• Building places that make people feel they belong

• Long term thinking in decades, not development cycles

• The responsibility of builders in shaping culture

I hope you enjoy the conversation. Feel free to share and let me know what resonates with you in the comments.

Adam

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In many ways, I’d say this is one of a few defining lessons from my life. For years I tried to get value from all sorts of things: school, sports, work, social life, traveling, the next coffee or meal out.

And I still struggle with it. I know the next trip, fancy dinner or purchased life upgrade isn’t going to bring lasting satisfaction but it often feels like a high school version of myself wrestling with a more evolved self that has learned and then forgotten many of these lessons.

Perhaps my favorite line from any Tuesdays with Morrisey episode was when Jerry Colonna, famed venture capitalist and executive coach, commented that much of his life is a continued struggle, striving and failing to integrate the wisdom discovered in his own life and of the great thinkers throughout human history.

What I see playing out in my own life, I increasingly see reflected at a cultural level as well.

I may break some of these topics out into longer form observations, but for now here are the highlights:

• Socioeconomic - Between “the scariest chart in the world”, the fact that the top 10% of earners make up 50%+ of consumer spending, and general cost of living (e.g. housing as a percentage of income), I foresee a return for more traditional values and even multi-generational living as society questions whether American hyper-individualism still serves us. For more on this topic check out the TWM episode with Dr. Corey Keyes, or my article on Family Values.

• Meritocracy - Last year, David Brooks wrote an article in the Atlantic titled How the Ivy League Broke America. While I don’t necessarily subscribe to the idea that America’s effort to optimize everything is directly related to the Ivy League, I do wonder if it’s working. A few years back, I attended a well-known men’s retreat. The core demographic was 35-year-old guys that sold a company, made a bunch of money, and were trying to figure out what to do with their lives. Seeing this pattern from guys that “won the game” should be a caution that perhaps there are other things we should be optimizing for, whether that’s presence, enjoying the process, focusing on the inputs, or having fun.

• Homogeneity - When I was in college, our friend group got the opportunity to create our own vernacular. These days kids from coast to coast all sound the same with terms like “mid”, “gyat”, “bet”, “skibidi”, “rizz” and “67”. I suspect we’ll see a more homogenous generation emerging, going after the same career paths, in the same cities, and foregoing the essential life opportunity of cultivating their individual uniqueness. One of my mantras is “if you don’t know what you want, you’ll only be left with comparison”. There is a lot of danger to our young people failing to create their own dreams, and falling victim to comparison as expectations for what life should be continue to rise.

• Luxury and Leisure - Concepts and experiences seem to be more built for the digital world rather than the material world driven by influencer culture. What I find interesting is that many of the “creators” we celebrate are not creators at all, but super consumers. I’m also seeing this continued trend I call “minimalist luxury” where hospitality operators offer a lower level of service at higher prices in exchange for “the vibes”. I discussed how social media impacted society, culture and the human need for status in the TWM episode with an American author living in Tokyo, David Marx.

• Technology, AI and ChatGPT - It’s concerning how much time people spend on phones and ChatGPT, and outsourcing brain capacity to technology. I worry about college and school-aged kids who may never learn the foundational skills behind the things they are automating, whether that is financial analysis, programming, or writing. I also worry about what “answer platforms” will do to human intuition, judgment, and ultimately the future of work.

• Amazonification - Last month I spent 10%+ of my after tax income with Jeff Bezos’ owned companies, specifically Amazon and Whole Foods. I “woke up” when realizing that I am giving Amazon 8-15% of the proceeds from private businesses that I really like simply out of convenience and habit without any critical thought. It’s a reminder that financial decisions are moral decisions and we have the opportunity to “vote with our wallet” every day to support communities and businesses with intention. This month my goal is to spend $0 with Bezos.

In my view, a lot of what we are seeing societally is a derivative of the attempt to get disproportionate value of things that aren’t going to be able to provide it, whether that is comfort, convenience or status.

So where do we go? There is a lesson to be learned from Gay and Katie Hendricks, a couple that I consider to be some of the original conscious leadership and personal development thinkers. In our podcast conversation, they shared their view greatest expressions are creativity, authenticity, and love, with the inputs for these being presence, ownership, wonder, honesty, and courage.

I think they are right, and these observations serve as a reminder that the things that really bring value and richness are internal and enduring: authenticity, presence, emotional capacity, comfort with self, an underlying sense of trust. Ideals that stand in contrast to where society and powerful forces point our attention.

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I have always been interested in leadership, meaning and purpose. More specifically, why people do what they do and the underlying, often unexamined, meaning beneath it.

In this case, I wanted to go a little deeper on some commercial themes that are impacting our broader economy to challenge my less researched understanding on a few of these topics.

While I believe a sense of meaning is of utmost importance, I have also learned and observed that without economic security, societies don’t have the same agency to pursue meaning on their own terms which makes it interesting and important to include economics and business concepts as part of my historical focus areas.

We covered bitcoin, sports ownership, private credit and private equity.

Here were the top takeaways from the series:

• Bitcoin and Cryptocurrency - Crypto and the underlying technology continue to have a lot of promise, however practical applications are still relatively untested and the primary benefit remains being a store of value. Despite the fluctuations that occur when the economy tightens, and noise of memecoins and yolo bets, the majority of bitcoin holders specifically are long-term holders.

• Sports Ownership - Sports is remarkable in the digital age as vehicle for community, identity and among the last frontiers for live entertainment. As sports continues to converge with entertainment, media and tech, we’re seeing what seem to be more non-linear investments in media rights, stadium development and within the sports teams and leagues themselves through private equity and venture investment.

• Private Credit - Lending outside the regulated banking environment has grown from $500B to $2T in AUM in the last 10 years, and is expected to grow to $3T by 2030. It’s particularly popular among private equity firms to allow them to access capital tailored to their needs. While the asset class has performed well historically, there are concerns that the industry is overextended as well as concerns as to who is really holding the risk for these loans, whether pension funds or HNW individuals, and what’s the impact of a correction in this asset class.

• Private Equity - There has been such a massive growth in this space with statistics showing that there are more private equity firms in the U.S than there are McDonalds locations. With concerns of a private markets correction, many pension funds and historical funders are reallocating away from private equity. Concurrently, with valuation adjustments over the last 5 years, many firms are struggling to exit prior investments and those observing the industry say that the rise in retail access to private equity funds are the firm’s efforts to tap a new market to make up for the liquidity needs associated with pension fund reallocation and longer hold periods for investments.

As always, I would love to hear your thoughts and feedback on the series, as well as content and guest suggestions for the future. Thanks for a great year, looking forward to 2026.

- Adam

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Welcome to the fourth and final episode in our mini-series on the alternative asset market.

Dr. Ken Wiles is a clinical professor of finance and the Executive Director of the Private Equity Center at the McCombs School of Business at the University of Texas at Austin. With decades of experience across investment banking, software, restructuring, and academic leadership, Ken brings a rare mix of practitioner and academic insights on private markets.

In this episode, we explore the evolution of private equity from the early LBO era to today’s liquidity constraints, and why Ken believes this is the best time in history to be an entrepreneur.

Episode Highlights (75 seconds) | Full Episode Linked Above

Top Takeaways

1. Ken explains how lower discount rates, the development of the junk bond market, and abundant inefficiencies in the 1980s created the perfect runway for PE to grow from a niche into a $22T asset class.

2. When the Fed raised rates at the fastest pace in its history, valuations dropped sharply. But unlike public markets, private-market declines happen in the dark. Even though fundraising slowed 40%, deal flow dropped 30%, and firms quietly extended maturities, restructured, or “extended and pretended”, without many people outside the industry noticing.

3. “Liquidity doesn’t matter until it does and then it’s the only thing that matters”. According to Ken, Liquidity is the biggest risk in private equity today. Pension plans, which provide two-thirds of all PE capital, aren’t receiving distributions as quickly. Without liquidity, returns fall, fundraising slows, and many funds will struggle to raise their next fund, which may lead to consolidation across PE and VC.

4. Ken sees the rise of new technologies leading to a new golden age in entrepreneurship. “This is the  greatest period to be an entrepreneur or have an idea in history. It’s amazing. Thanks to AI, cloud infrastructure, and on-demand development talent, the cost of building a company has collapsed. Tasks that once required millions and large teams can now be executed by small groups in weeks. Barriers to entry have never been lower.”

Resources

• Ken Wiles on LinkedIn

Full List of Topics Covered

• The origins and evolution of private equity

• The impact of interest rates four decades of PE returns

• The 2022–2024 “private market crash” no one saw

• Liquidity challenges and their impact on pensions and funds

• How private credit prevented a maturity crisis

• Manipulated unicorn valuations and extend-and-pretend dynamics

• The new economics of entrepreneurship in an AI-enabled world

• College students, AI, and modern career preparation

• The shrinking operating costs of building software

• Entrepreneurship through acquisition and the rise of search funds

• Why more businesses will be built with smaller teams

• The growing consolidation of trades, CPA firms, and local service businesses

• The future of private equity, venture capital, and public markets interplay

Hope you enjoy the conversation. Feel free to share and let me know if anything resonates with you in the comments.
– Adam

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Welcome to the third episode in our mini-series on the alternative asset market.

Brent Humphries and Marc Cooper are leaders in AllianceBernstein’s Private Credit Group, part of a global investment firm that manages roughly $800B in assets.

With private credit getting a lot more attention in the news, we break down what private credit actually is, why it has grown so rapidly, and what its rise means for investors, lenders, and the broader financial system.

Episode Highlights

Top Takeaways

1. Private credit has quietly become one of the biggest shifts in modern finance, growing from about five hundred billion of assets under management to roughly two trillion in the last decade. It is now the primary way many private companies access capital, replacing what used to be a market run by the traditional banking system.

2. The rise of private credit was largely created by regulation. After the financial crisis, new rules made it harder for banks to hold certain loans, and private lenders stepped in with faster, more flexible financing that met the needs of private equity and middle-market companies.

3. Investors have been drawn to private credit because of its combination of yield, downside protection, and floating rates. It has delivered strong, steady returns without taking on other risks tied to interest rates, foreign currency, or market volatility.

4. The big question now is where the risk sits. As more lending moves outside the regulated banking system, pension funds, insurance companies, and individuals hold a growing share of the credit exposure.

5. The next phase of private credit will include more retail access, more participation from insurers, and continued specialization among lenders. At the same time, AI is beginning to reshape underwriting, research, and operations, making investment teams faster and more efficient.

Resources

• AB Private Credit LinkedIn

• Brent Humphries LinkedIn

• Mark Cooper LinkedIn

Full List of Topics Covered

• What “private credit” means and how direct lending works

• How bank regulation after 2008 shifted lending outside the traditional system

• The role of the “unitranche” structure in simplifying deal execution

• Why private credit returns have attracted pensions, institutions, and high-net-worth investors

• How to evaluate private credit fund managers (track record, team retention, sector edge, platform model)

• Perceived risks and the “shadow banking” debate

• The role of insurance capital and the rise of investment-grade private credit

• How AI is influencing underwriting, research, and software-sector lending

• The outlook for the next 5–10 years in private credit

Hope you enjoy the conversation. Feel free to share and let me know if anything resonates with you in the comments.
– Adam

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When we think of great storytellers, we generally think of someone with a lot of stories. However, after 60+ podcast episodes with many great authors, entrepreneurs and thinkers, something that has become clear to me is how common it is for a person to have a primary story or concept that has become the foundation of their career and work.

I don’t think it is because these individuals lack new material as much as they discovered a vehicle for outsized impact: one great story, told extremely well.

Simon Sinek is great example of this idea. His concept “Start With Why”, as captured in his 2009 TedTalk “The Golden Circle”, was the original story that eventually evolved into a massive platform. Here are a few more examples from prior Tuesdays with Morrisey podcast guests:

• Kim Scott realized the power of Radical Candor when Sheryl Sandberg showed her that the best feedback happens when you care personally and challenge directly.

• Liz Wiseman saw that the best leaders make the people around them better while watching leaders operate at Oracle, which eventually became her work on the concept Multipliers.

• Steven Pressfield named the invisible force that stands between our current selves and our potential, calling it resistance, which became the central idea of The War of Art.

• Lisa Sun received feedback early in her career that she lacked “gravitas,” which sent her down the path of unpacking and codifying confidence.

• Antong Lucky was told in prison that if he could lead people to do wrong, he was just as capable of leading people to do right

I had a friend who left his job in corporate to pursue screenwriting. One of the things he shared with me about great screenwriters and authors is that they build a script like a lightbulb and wait to turn it on at exactly the right moment. Someone who I believe does this incredibly well is Amor Towles in his books Gentleman in Moscow and Rules of Civility.

The speakers mentioned above also create the lightbulb moment for listeners, by presenting their ideas as if they are sharing them for the first time, inviting listeners through their own process of discovery.

I admire the discipline and commitment to craft that comes from committing to perfecting one powerful story. And just like we discussed the power of heroism on a small scale during our conversation with Dr. Scott Allison, I believe there are lessons in the power of a single story. It invites us to consider the singular elements in our own lives that might lead to outsized impact, whether that is a story, an insight, or a gift we are meant to share with the world.

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Welcome to the second episode in our mini-series on the alternative asset market.

Gennaro Leo is a sports executive and the co-founder of Austin Sports Ventures, a firm that partners with venture capital and private equity firms to invest in and operate assets across professional sports leagues, teams, and high-growth technology startups.

In this episode we discuss how sports ownership is changing and growing into a sophisticated asset class that combines real estate, technology, media and entertainment.

Episode Highlights

Top Takeaways

1️⃣Sports ownership continues to evolve from a local, passion-driven pursuit into an institutional asset class.

2️⃣Media and entertainment continue to be at the center of sports. Many consider sports to be the last frontier of live entertainment, and the emergence of deals like Amazon’s Thursday Night Football, shows like Netflix’s Drive to Survive series, the popularity of the TikTok sensation Savannah Bananas show the intersection of modern media and sports.

3️⃣Stadiums and sports related real estate development, like SoFi Stadium and The Star in Frisco, show how real estate can unlock new revenue streams for ownership groups or “StadCos” through seemingly non-linear investments into communities through architecturally significant year round venues.

4️⃣Italian soccer has become a case study in global sports ownership with American investors now owning more than half of Serie A clubs. Gennaro’s experience at AS Roma and Hellas Verona highlights the need for process, discipline, and respect for tradition when foreign owners enter a league.

5️⃣ As ownership and media distribution models continue to evolve, opportunities open up for players, fans, and investors. We’re seeing athlete-led venture funds to mixed-use developments, and increasingly the merger of sports with media, tech, and real estate.

Resources

• Gennaro Leo LinkedIn

Full List of Topics Covered

• Gennaro’s career from tech, media, real estate and sports ownership

• The evolution of stadiums as community and economic hubs

• U.S. investment in European football and its impact

• How media innovation drives sports growth

• The intersection of sports, tech, and real estate

• Building sustainable value in a global sports ecosystem

• The future of the player and fan experience, and ownership models

Hope you enjoy the conversation. Feel free to share and let me know if anything resonates with you in the comments.

– Adam

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I’ve always been fascinated about how people make decisions, and mentorship has been a very important part of my journey, both through direct relationships and books.

So in college I started asking successful people a question, beginning with then KPMG CEO John Veihmeyer in Miami University’s Farmer School of Business main auditorium in front of 500 other students.

I said from the back of the upper deck:

“John, you’ve been really successful. So assuming since you’ve been successful at this you must have had other things you could have done. How did you evaluate opportunities and ultimately choose the right path for you?”

In the beginning I got a series of answers that weren’t satisfying to my 20 year-old self. Stuff like “I just kept learning”, or “I never got a better opportunity”.

It wasn’t until 5 or so years later when I was speaking with a SVP of Legal at one of my consulting clients where I got an answer that really resonated.

“To be honest I don’t believe that I critically evaluated opportunities, and if I could do it again, I would more fully evaluate the opportunities that crossed my path...

I also wouldn’t have looked at things so long term, but rather in 2 - 3 year time slots to learn something new about myself and the world...

and if I would have done that I would have had a much more interesting path”.

While I don’t necessarily believe this advice suggests that one should change careers or jobs every few years, it has been a helpful frame for me to get present and focus on more actionable time periods.

One of my mentors speaks a lot about the concept of being a “master craftsman” which inherently implies a long game, but often involves spending dedicated time developing a combination of skills and experience that is uniquely valuable.

It reminds me of Christina Wallace’s idea in The Portfolio Life, that we don’t have one linear career or path, but a collection of experiences that compound over time.

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