—

SPONSORS:

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/jay-ritter-1323861/

Company: https://www.ufl.edu/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Cold Open: Three Waves of Tech IPOs

1:43 Welcome to Run the Numbers

3:10 Meet Jay Ritter, Mr. IPO

4:02 The Original 1983 Question

5:08 PCs, Internet, and AI Compared

9:36 Network Effects

14:46 Sitzfleisch: Outlasting the Field

16:10 Where Have All the IPOs Gone

23:29 IPOs as Relationship-Building

26:31 Why Investors Tolerate Founder Control

29:16 Dual-Class Stock’s Origins

30:21 How Jay’s Thinking Evolved

31:36 Why Boards Don’t Get Angry

34:39 Banks’ Real Client: Institutions

37:08 Book Building

38:56 Why Direct Listings Haven’t Taken Over

39:57 What Goldman Is Really Selling

41:57 Sentiment vs. Long-Term Performance

43:13 Does Staying Private Help Society

49:35 Asking Better Questions with EY

52:12 Are Markets Efficient

#RunTheNumbersPodcast #IPO #MrIPO #CapitalMarkets #TechIPOs

CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company. They break down why product-market fit is now a moving target, how AI changes go-to-market, what exploding token usage means for margins and pricing, and how founders should think about building businesses when the underlying technology is changing this fast.

—

SPONSORS:

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guests:
https://www.linkedin.com/in/rebecca-schwartz/

https://www.linkedin.com/in/rahulrekhi/

https://www.linkedin.com/in/fredhavemeyer/

Companies:

https://www.tabs.com/

https://fleetai.com/

https://www.rogo.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics:

https://www.mostlymetrics.com

—

RELATED EPISODES:

Rahul Rekhi, President - Rogo

—

TIMESTAMPS:

0:00 Preview and Intro

1:16 Welcome to Run the Numbers

3:17 Meet the Panel: Rebecca, Fred, Rahul

9:52 How Rogo Found PMF

13:47 How Tabs Found PMF

14:51 Growth Rates: Headcount and Revenue

16:23 The Real Hiring Constraint

17:21 What “Forward Deployed” Actually Means

18:53 What’s Blocking AI Adoption Now

20:19 How Sales Hiring Has Changed

24:34 How Go-to-Market Has Changed

25:28 Pricing Models: Then vs. Now

28:18 Tabs’ Pricing Evolution

29:20 What the Finance Team Looks Like

31:00 How Far You Can Push Outsourced Accounting

32:43 Managing AI Gross Margins

35:07 The North Star Metric for AI Companies

37:02 Token Spend vs. Per-Seat Pricing

39:34 Asking Better Questions: What Counts as ARR

41:38 Biggest Bug in Cash to Collections

43:05 Closing Advice for Founders

#RunTheNumbersPodcast #ProductMarketFit #AIStartups #GoToMarket #CFOLife

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition. They break down why companies underprice, how usage-based and hybrid pricing change the game, and what revenue infrastructure needs to look like as you scale.

—

SPONSORS:

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/wisam-hirzalla-9b20a91/

Company:

https://stripe.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics:

https://www.mostlymetrics.com

—

RELATED EPISODES:

Kunal Agarwal, CFO - Gorgias

—

TIMESTAMPS:

0:00 What Drives Billing Downstream

1:41 Welcome to Run the Numbers

2:37 Wisam’s Path to “Queen of Billing”

4:55 What Head of Billing at Stripe Entails

5:45 Defining Quote-to-Cash

7:50 Layer 1: Pricing and Packaging Mistakes

14:46 Pricing Models Rising Because of AI

18:11 Layer 2: Inside a Quote

19:27 Why Enterprise Deals Get So Messy

24:38 Layer 3: Contracting

27:21 Layer 4: Billing

30:15 Why Usage-Based Billing Is So Complex

34:51 Tokens as a Pricing Unit

36:57 Billing’s Move Out of the ERP

39:53 Layer 5: Provisioning and Entitlements

43:36 Layer 6: Tax

44:27 Layer 7: Getting Paid

48:18 Layer 8: RevRec

50:52 When Billing Stopped Being Back Office

51:47 Asking Better Questions Segment

52:28 Will AI Replace Finance Jobs

#RunTheNumbersPodcast #QuoteToCash #StripeBilling #SaaSPricing #CFOLife

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.

—

SPONSORS:

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/meredithfinn1/

Company: https://front.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Adam Swiecicki - CFO of Rippling

https://youtu.be/JyGJVpmZNac

Aurélien Nolf - CFO of Navan

https://youtu.be/siwzJSRXAvY

—

TIMESTAMPS:

0:00 The CFO/COO Dual Mandate

1:45 Welcome to Run the Numbers

2:52 Front’s In-House Podcast Studio

3:41 Meredith’s Investment Thesis on Front

7:21 The “Portfolio Career” Analogy

8:35 What She Had to Unlearn as an Operator

13:13 Books on Strategy vs. Execution

16:17 When a CFO Should Also Be COO

18:27 What the COO Hat Actually Covers

20:20 Where the Two Roles Conflict

25:42 Budgeting for AI Token Costs

29:16 Using Internal Usage as a Benchmark

35:40 Funding a Series A Bet Inside a Series D Company

38:04 Sizing Bets: Core, Adjacent, Moonshot

40:04 The Secret to Re-Accelerating Growth

41:46 Going Deeper, Not Wider

43:18 What the Pricing Overhaul Taught Her

47:30 Why Customer P&L Matters

50:11 Lightning Round Begins

51:32 Advice to Her Younger Self

52:33 Front’s Finance Tool Stack

53:21 Craziest Expense Ever

#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.

—

SPONSORS:

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/claire-bramley-133b7174/

Company: https://www.xero.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:00 Xero and CJ’s History With It

4:12 Xero’s Size and Scale Today

5:10 The Expanding CFO Role

7:06 Hiring Experts You’re Not

8:47 Imposter Syndrome

11:00 Getting Better at Asking Questions

15:04 Asking the “Stupid Question”

16:21 Finance as the Corporate Junk Drawer

17:48 The Trial Period Idea

18:24 Tripwires: Leading Indicators for CFOs

25:35 AI Hype vs. Main Street Reality

26:44 What Small Business Owners Actually Want

28:45 What Big Corps Underestimate

31:10 Trust as a Competitive Moat

33:45 Why the Line Is Thinner for Small Biz

35:12 AI Inside Claire’s Finance Team

37:23 AI for Investor Relations

39:28 Diversity as Capital Allocation

42:07 A Decision Diversity Changed

44:45 Lightning Round Begins

46:06 Advice to Her Younger Self

48:49 Craziest Expense Ever

#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance

On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics:

https://www.mostlymetrics.com

—

RELATED EPISODES:

Jersey Mike’s IPO: The $4.2B Sandwich Machine

—

TIMESTAMPS:

0:00 Fly Like a G6

0:29 $17M on jets: Alex Karp guess

1:16 Sam Walton starts it all

2:49 The yellow legal pads

4:37 Walmart Aviation founded (1968)

5:14 Piston to Bombardier jets

6:51 Walmart’s modern jet fleet

8:13 Where it hides in SEC filings

9:25 SEC Reg S-K Item 402

13:37 Gulfport Energy scandal

14:42 Tyco: Kozlowski & Schwartz

16:57 When jets are actually useful

17:55 P&L vs. balance sheet treatment

18:40 PP&E and depreciation basics

19:04 Off-balance-sheet leases

19:28 The chartering loophole

19:54 “Uber Jet” fractional ownership

23:14 How activists hunt jet spend

23:36 Flight registries & tail numbers

24:13 Jack Sweeney vs. Elon Musk

25:00 What top companies spend

25:18 Walmart’s fleet is #1

26:17 Charter vs. lease vs. own

29:02 Should we care? 3 angles

30:06 Angle 2: opportunity cost

30:59 Angle 3: company size

31:42 General Electric’s shadow jet

32:50 Back to Alex Karp

34:02 Credits

#RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.

—

SPONSORS:

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/richardharem/

Company: https://rapidsos.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:10 What RapidSOS does

4:59 CJ’s own car accident

5:33 What’s broken about 911

6:50 Who’s the actual customer

7:46 How RapidSOS monetizes

10:13 Sponsors — Pulley | Rillet | Maximor

13:27 Too much data, too much noise

16:35 Data pollution and trust

18:24 The data stack early on

19:25 Should BI have come sooner?

20:45 The framework: questions to decisions

22:43 Building a data culture

23:58 Sponsors — Brex | Anrok | RightRev

26:51 Bottoms-up vs. top-down AI

28:42 Inspiration, not training

32:24 The three-phase AI progression

33:31 Founding an AV company at 8

35:37 Giving people room to grow

38:12 Depending on heroes

39:55 Working under founder personalities

41:23 Do startups undervalue what they sell

42:48 A price hike, zero churn

43:24 Signs you’re underpricing

44:57 Lightning round

45:03 Screwed up: refreshed data before a demo

47:15 Advice to younger self

47:41 Finance software stack

48:37 Craziest expense: personal gas

49:29 Credits

#RunTheNumbersPodcast #CFO #Fintech #AIStrategy #FinanceLeadership

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo to unpack how Plaid’s three-layer network powers digital finance and monetizes financial activity. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company.

—

SPONSORS:

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at

https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you’ve never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

—

LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/seun-sodipo-1498b580/

Company:

https://plaid.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics:

https://www.mostlymetrics.com

—

RELATED EPISODES:

Blake Grayson - Docusign

—

TIMESTAMPS:

0:00 Preview and Intro

2:12 What Plaid does

3:53 How Plaid makes money

7:04 Eight months in, not new anymore

8:57 Sponsors — RightRev | Pulley | Rillet

11:48 Career path: Stripe, Glossier, Plaid

14:32 Evaluating durability from the outside

15:36 Rising expectations and AI

17:23 Top-down vs. bottoms-up AI adoption

20:06 Sponsors — Maximor | Brex | Anrok

23:20 Coolest AI use case: sorting physical mail

25:21 How her questions have changed

27:11 AI should make you think deeper

27:51 Finance AI Day explained

31:23 A four-month journey to usable tools

32:22 How AI changed her leadership style

33:19 Skills that matter more now

36:22 The Objective, Strategy, Tactics framework

39:56 What planning reveals about an org

41:36 Sequential vs. parallel planning

45:38 Measuring the value of a network

47:33 What people underestimate about Plaid

48:56 Lightning round

48:56 Screwed up: the reversed page order

49:39 Advice to younger self

50:32 Finance software stack

51:43 Craziest expense: the photo shoots

52:20 Credits

#RunTheNumbersPodcast #CFO #Fintech #AIStrategy #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Dan Griggs, CFO of Intercom, to break down how finance leaders should think about pricing, forecasting, and resource allocation in the AI era. Dan explains why “it’s not zero” is his guiding forecasting principle, how Intercom landed on 99 cents per AI resolution for Fin, and what it means to build an AI product that could eventually cannibalize a successful SaaS core. A candid look at managing uncertainty while still making bold bets.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

—

LINKS:

Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/

Intercom: https://www.intercom.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown

https://youtu.be/ttedn4AULt8

—

TIMESTAMPS:

00:00:00 Cold Open

00:01:03 Intro to Dan Griggs and Intercom’s AI Pivot

00:02:45 From Ice Cream to SaaS: Early Finance Lessons

00:04:19 Learning the Business by Living the Operations

00:06:26 Why Operational Reality Shapes Better Forecasts

00:08:00 “It’s Not Zero”: Forecasting the Unknowable

00:10:09 Scenario Planning, Ambiguity, and Psychological Safety

00:11:23 Sponsors — Brex | Metronome | RightRev

00:14:43 Keeping a Mental Model of Key Business Metrics

00:16:15 Using Mental Math to Sanity-Check Forecasts

00:17:28 Core Ratios Every CFO Uses to Vet Decisions

00:19:13 The Burn-the-Boats Moment for Intercom’s AI Pivot

00:20:53 Why AI Was an Existential, Not Incremental, Bet

00:22:21 Which SaaS Categories AI Can Fully Replace Work

00:23:04 Why Finance Hasn’t Had Its AI Moment Yet

00:23:39 Sponsors — Rillet | Tabs | Abacum

00:27:05 Why Fin Needed Outcome-Based Pricing

00:28:59 The Tradeoff Behind $0.99 Per Resolution

00:30:46 Why Support Conversations Vary in Complexity

00:32:01 What Drives the Unit Economics of AI Resolutions

00:33:08 How Intercom Chooses Models as Costs Fall

00:35:19 Replacing Generic LLMs With Domain-Specific Models

00:36:08 Selling an AI Product That Could Cannibalize the Core

00:38:50 Founder CEOs Versus Professional CEOs

00:41:47 Hiring Mistakes and Acting on Instincts

00:44:28 Intercom’s Finance Software Stack

00:45:49 The Craziest Expense Request

#RunTheNumbersPodcast #Intercom #AICustomerSupport #OutcomeBasedPricing #CFOInsights

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale.

—

SPONSORS:

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

—

LINKS:

Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/

Company: https://www.huntress.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

How the Best CFOs Lead Without Being the CEO | Ken Stillwell

https://youtu.be/O4cx9NBqQso

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:01 Maria’s Background

00:03:09 People-First Team Building

00:05:16 People, Process, Systems at Scale

00:07:13 Removing Friction Outside Finance

00:09:15 Data Transparency & Decision-Making

00:11:06 Sponsors — Abacum | Brex | Metronome

00:14:22 Forward-Deployed Data

00:16:21 Centralized Data vs. Silos

00:19:23 Finance as Data Steward

00:21:08 Cost-to-Price Feedback Loop

00:22:35 Curiosity Builds Credibility

00:23:43 Sponsors — RightRev | Rillet | Tabs

00:27:12 Trust First, Then Impact

00:30:27 Celebrating Small Wins

00:31:21 From Transactions to Insights

00:33:00 CFO at the Revenue Table

00:34:32 Educating the Org on Metrics

00:36:21 Customer-Level Margin Reality

00:37:13 Using Facts to Change Decisions

00:38:27 Ownership Mindset in Growth Companies

00:39:10 VC vs. PE vs. Public CFO Tradeoffs

00:41:02 Operating Inside Constraints

00:42:18 Finding Your Stage Fit

00:44:17 Building a Personal Advisor Network

00:46:43 Visibility and Women in Leadership

00:47:44 Work–Life Integration, Not Balance

00:48:45 Lightning Round: Biggest Mistake

00:50:10 Advice to Younger Self

00:51:36 Finance Tech Stack

00:52:01 Craziest Expense Story

00:52:44 Credits

#RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.

—

SPONSORS:

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

—

LINKS:

Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/

Pegasystems: https://www.pega.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

https://youtu.be/T2YjdoiJtFA

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:57 Sponsors — Tabs | Abacum | Brex

00:07:26 The Strategic Value of Being Number Two

00:08:46 Earnings Calls, Messaging, and Real-Time Judgment

00:10:41 Using Feedback to Sharpen Executive Communication

00:11:38 CFOs as Storytellers & Message Repetition

00:12:31 Managing Up: Reading the Room

00:13:59 Learning the Hard Way: Misreading Dynamics

00:15:18 Confidence, Aggression, and Early CFO Mistakes

00:15:58 Sponsors — Metronome | RightRev | Rillet

00:19:45 When to Email vs Pick Up the Phone

00:22:48 Tailoring Communication to Different Functions

00:23:23 Audience-Specific Messaging: “Why Me?”

00:25:24 Values vs Behaviors in Leadership

00:28:13 Why Big Changes Need Anchoring

00:31:14 Moving Pega to the Cloud

00:32:43 Rewiring Sales Comp for ARR & ACV

00:34:56 Sales Credibility Breakdowns with Customers

00:36:20 Economics vs Trust in Sales Teams

00:37:48 Balancing Field Feedback with Company Goals

00:39:17 De-Emphasizing New Logos to Fix the Sales Model

00:41:12 The Danger of Over-Obsessing on KPIs

00:42:51 Public vs Private: Incentives and Operating Discipline

00:45:57 Why Companies Go Private: Motivation Over Patience

00:47:29 The Shrinking Public Markets

00:47:57 Private vs Public CFO Mindsets

00:49:39 Meeting Investors Where They Are

00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud

00:51:29 Long-Ass Lightning Round

00:53:24 Ken’s Finance Tech Stack & Craziest Expense

00:54:39 Credits

#RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript’s metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

—

LINKS:

Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/

Postscript: https://postscript.io/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://youtu.be/cgHOtvG1Ces

The IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio’s Former CFO

https://youtu.be/PTKAUD7PSWU

The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

https://youtu.be/Dl8nDZPJMpE

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:22 Sponsors — Rillet | Tabs | Abacum

00:06:55 Interview Begins

00:07:36 First Finance Hire and Early Scale at Postscript

00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel

00:10:31 Partnering With Sales and Building Deal Desk

00:13:16 Pricing Guardrails, Payback, and Deal Economics

00:15:35 How Deal Desk Evolves Over Time

00:16:01 Sponsors — Brex | Metronome | RightRev

00:19:44 Making Finance a Deal-Closing Partner

00:20:44 Automating Deal Desk With a Slack Bot

00:23:48 How Technical Finance Leaders Need to Be

00:25:17 Automating Without Engineering Help

00:27:12 Why Human Touch Still Matters in SaaS

00:27:53 Postscript’s Finance Tech Stack

00:28:30 ERP Migration and Month-End Efficiency

00:29:42 The Reality of Continuous Close

00:30:34 First Real AI Wins in Accounting

00:31:18 Experimenting With AI Forecasting

00:33:32 Metrics That Matter: Usage as a Leading Indicator

00:35:49 How Metrics Evolve as the Company Scales

00:37:41 Understanding the Product in a Usage-Based Model

00:39:27 Micro-Seasonality and Forecasting Volatility

00:42:21 How to Use Benchmarks Without Misusing Them

00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake

00:45:45 Advice to a Younger Finance Leader

00:47:05 The Private Jet Accounting Story

00:49:11 Credits

#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.

—

SPONSORS:

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

—

LINKS:

Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/

Wellhub: https://wellhub.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader

https://youtu.be/iNHbkcG7YEo

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:19 Sponsors — RightRev, Rillet, Tabs

00:06:43 Accidental CFO Origin Story

00:07:34 Consulting to Operations Pivot

00:08:12 Why Finance Clicked for Bruno

00:09:28 McKinsey Prioritization in Real World

00:10:02 Eisenhower Matrix and Prioritization

00:11:08 Investing in Non-Urgent Work

00:13:30 Lessons From AOL Reinvention

00:16:10 Sponsors — Abacum, Brex, Metronome

00:20:01 Career Growth Through Hard Problems

00:20:52 Broadening Skills Through Change

00:23:12 Five Core Finance Principles

00:24:02 Cash Is King

00:25:14 Driving Sustainable Growth

00:26:01 No Surprises and Forecasting

00:26:07 Finance as Business Enabler

00:27:22 Less Is More Philosophy

00:28:47 Hardest Principle: Less Is More

00:29:46 Deterministic vs Probabilistic Forecasting

00:31:11 Marketplace Volatility and Forecast Error

00:32:10 Ensemble Models Explained

00:33:37 Forecast Accuracy Gains

00:34:53 Building Models In-House

00:36:46 Why Explainability Matters

00:37:48 Empower Framework Introduction

00:47:47 Urgency, Compounding, Long-Term Thinking

00:48:10 Advice to Younger Self

00:50:06 Finance Stack and Expense Stories

00:52:51 Credits

#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance

In this episode of Run the Numbers, CJ sits down with Jason Kong, General Partner at Base10 Ventures, to unpack the firm’s focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10’s decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.

—

SPONSORS:

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS:

Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/

Base10 Partners: https://base10.vc/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips

https://youtu.be/vBY6WZBMljw

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:20 Sponsors — Metronome, RightRev, Rillet

00:06:02 Base10 Background

00:06:41 Automation for the Real Economy

00:09:27 Vertical vs. Horizontal Software

00:10:38 Cash Flow and Durability

00:11:19 Product-Market Fit and ROI

00:12:56 Growth Limits Selling to Tech

00:13:19 The Size of the Real Economy

00:14:16 Sponsors — Tabs, Abacum, Brex

00:18:50 Base10’s Giving Model

00:20:30 Access, Education, and Tech

00:21:53 Purpose and Founder Alignment

00:22:51 Radical Transparency

00:23:56 Portfolio Focus and Strategy

00:24:05 Investing Ahead of Consensus

00:26:29 ERP Adjacency as Alpha

00:28:58 Lessons From Hedge Funds

00:32:29 Public Markets Reality

00:34:05 Public vs. Private Investing

00:34:48 The Series B Sweet Spot

00:36:49 A Bifurcated Series B Market

00:38:56 Fast Series Bs and 2021 Vibes

00:42:16 What Series B Looks Like Now

00:44:36 Back Office Automation

00:46:02 ERP-Centric Workflows

00:48:33 Long-Ass Lightning Round

00:49:36 Shorting SaaS in 2022

00:50:16 Fantasy Football and Investing

00:52:57 Career Advice That Surprises

00:55:03 A Contrarian Venture Take

00:56:22 Credits

#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation

In this episode of Run the Numbers, CJ sits down with Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

—

LINKS:

Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/

Company: https://www.samsara.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

https://youtu.be/VRpTNDIfzPY

From SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classics

https://youtu.be/kMuJ6gAuEpg

Driving revenue without selling | Greg Henry of 1Password

https://youtu.be/f5FsNoG8A3E

—

TIMESTAMPS:

00:00:00 Preview & Intro

00:02:40 Sponsors — Brex | Metronome | RightRev

00:06:18 Interview Begins

00:06:46 Dominic’s Early Career

00:08:47 From ServiceNow to CFO

00:09:47 Joining Samsara

00:10:54 COVID, Burn, and a Down Round

00:12:40 IPO Messaging and Investor Education

00:15:50 Sponsors — Rillet | Tabs | Abacum

00:20:27 Hardware + Software Story

00:21:29 What Samsara Does

00:22:30 Data, AI, and ROI

00:23:23 Horizontal Platform and Verticals

00:24:27 Growth Drivers at Scale

00:26:09 Selling Into Operations

00:28:19 Change Management in Legacy Orgs

00:29:46 Non-Discretionary Budgets

00:33:02 Storytelling Lessons from Scarpelli

00:36:14 Managing Analysts

00:39:23 Earnings Timing Strategy

00:41:06 Metrics and Investor Trust

00:42:38 Investor Communication Channels

00:44:22 Investor Days and Long-Term Vision

00:45:37 Annual Planning Maturity

00:48:24 Forecast Accuracy and Cadence

00:49:28 The 1000-Day Strategy

00:50:40 Top-Line and Margin Targets

00:51:59 Capital Allocation by Function

00:54:46 Becoming a CFO

00:58:21 Lightning Round and a CFO Mistake

01:02:41 End Credits

#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets

In this episode of Run the Numbers, CJ Gustafson sits down with Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.

—

SPONSORS:

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

—

LINKS:

Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/

The Coyle Group: https://thecoylegroup.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

The Coyle Group - Business Insurance

https://www.youtube.com/@TheCoyleGroupNY

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:53 Sponsors — Abacum | Brex | Metronome

00:05:39 Interview Begins with Gordon Coyle

00:06:23 Gordon Coyle & The Coyle Group

00:07:21 Explaining Insurance on YouTube

00:08:40 Turning Education into Inbound Leads

00:09:40 Content as a Pull Strategy

00:10:53 Insurance Complexity for Tech Founders

00:13:28 Why Investors Require D&O Insurance

00:14:09 What D&O Covers and Why It Matters

00:15:50 Sponsors — RightRev | Rillet | Tabs

00:20:19 Who D&O Covers and Rising Investor Pressure

00:22:37 D&O Limits and Cost Tradeoffs

00:23:21 Panic Calls and Late D&O Purchases

00:24:39 How Defense Costs Erode Coverage

00:25:31 Common D&O Claims and Employment Risk

00:27:08 D&O vs E&O Explained

00:29:12 Cyber Insurance and Social Engineering

00:31:59 AI’s Impact on Cyber Risk

00:33:50 Real-World Ransomware Stories

00:34:17 Cyber Insurance as Money and Response

00:35:29 Business Email Compromise Scams

00:39:43 Why Tech Still Needs General Liability

00:41:16 What a BOP Covers

00:42:32 Convenience vs Proper Coverage

00:44:29 Surprising General Liability Claims

00:46:45 Insurance Costs for Startups

00:47:36 Higher Costs in High-Risk Industries

00:48:26 Balancing Budget, Risk, and Coverage

00:50:39 PEOs, Workers’ Comp, and EPLI

00:54:39 Choosing the Right Insurance Partner

00:56:42 End Credits

#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk

[Original air date: June 19, 2025]

In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it’s changing in the era of AI. He explains what the components of a company’s AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you’re preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention curves and gross margins, and how this relates to the ever-important LTV to CAC metric. As someone who has worked with prominent CFOs and interviewed many for a16z’s portfolio companies, Alex also describes the qualities of a great CFO, and shares his favorite interview question, before discussing CFOs, CEO, and board dynamics.

—

LINKS:

Alex Immerman on LinkedIn: https://www.linkedin.com/in/immerman

Andreessen Horowitz: https://a16z.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

a16z’s Alex Immerman on the Evolving Role of the CFO in the Age of AI

https://youtu.be/JIvHp-mlnzs

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means

https://www.youtube.com/watch?v=cgHOtvG1Ces

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:46 AI Margins Improve Dramatically

00:02:29 What Separates Great CFOs

00:03:29 Founder Mindset Drives Performance

00:05:31 Founder Intensity and Margin Expansion

00:06:57 Backing Unproven Bets Thoughtfully

00:08:29 Interviewing CFOs for Backbone

00:09:55 When CFOs Push Back on Strategy

00:11:25 CFO Trust With Boards and Investors

00:11:50 How CFOs Engage Investors When Hiring

00:14:44 Building Strong CFO Investor Relationships

00:16:18 Sharing Bad News Early

00:17:21 CEO Vision Versus CFO Validation

00:20:57 How AI Is Changing the CFO Role

00:23:56 Incumbents Versus AI-Native Finance Tools

00:26:24 CFOs Driving Internal AI Adoption

00:28:07 AI Impact on Customer Support Efficiency

00:29:26 Internal Leverage From AI Automation

00:31:29 Why Investors Care About LTV to CAC

00:34:00 LTV to CAC Across Business Models

00:36:26 Retention Curves Matter More Than Growth

00:38:16 Evaluating AI Gross Margins Long Term

00:40:04 Recipe for AI Margin Expansion

00:43:01 What Makes a Public-Ready CFO

00:44:47 Beating Guidance Drives IPO Performance

00:46:56 Growth Versus Profitability Has Rebalanced

#RunTheNumbersPodcast #CFOLeadership #FintechInvesting #AISaaS #VentureCapital

[Original air date: May 8, 2025]

When it comes to investor relations, an organization’s communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson of the Arbor Advisory Group and Jon Neitzell of Andruil Partners, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you’ve attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn’t (but probably should) before suggesting changes you can make to drive impact immediately.

—

LINKS:

Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/

Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/

Arbor Advisory Group: www.arboradvisorygroup.com/

Anduril Partners: https://www.andurilpartners.ai/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Investor Relations as a Strategic Weapon: A Masterclass

https://youtu.be/ac9xmURhAqE

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:02:22 Welcome to Sam and Jon

00:03:12 Linking Business Strategy and Communication

00:05:01 Proactive vs. Reactive Investor Relations

00:06:39 Tailoring the Message by Investor Type

00:08:05 Audience Opportunity and Ideal Shareholders

00:11:05 When the Investor Base No Longer Fits

00:12:21 Shifting Investors as Industries Change

00:13:16 Optionality Comes From Patient Shareholders

00:14:40 Conveying Conviction Through Credibility

00:17:03 Why Investor Days Build Trust

00:18:02 Metrics Versus Storytelling in IR

00:19:10 Choosing Metrics the Market Actually Rewards

00:22:30 Valuation Disconnects and Investor Confusion

00:23:17 Finding Metrics That Truly Drive Value

00:25:33 Avoiding Bad Capital Allocation Decisions

00:26:20 Disclose Versus Guide: Confidence Intervals

00:27:35 Knowing What You Don’t Know

00:29:33 Science Versus Art in Storytelling

00:33:11 When Algorithms Become Your Audience

00:33:56 Passive Investing Now Dominates Markets

00:35:16 Linking OKRs to Value-Driving KPIs

00:36:42 Closing the Strategy-Metrics Feedback Loop

00:38:07 When Investors Sense Operational Confidence

00:39:47 Why IR Becomes Strategy Consulting

00:41:28 Why IR Teams Stay Undersized

00:43:23 Sam’s Accidental Entry Into Investor Relations

00:44:34 Mentorship Over Formal IR Training

00:46:18 How Markets Outpaced IR Practices

00:47:01 Investor Days Go Virtual

00:49:34 Designing a High-Quality Earnings Call

00:50:41 Investor Days as High-ROI Investments

00:51:45 IR Websites as Investor Onramps

00:53:42 World-Class Investor Day Examples

00:54:20 Using AI to Prepare Investor Communications

00:56:19 Building a Proactive IR 2.0 Strategy

00:58:33 Why IR Requires Full Executive Buy-In

01:00:51 Data Transfers Conviction to Investors

01:03:31 Closing Reflections on Trust and Valuation

#RunTheNumbersPodcast #InvestorRelations #CapitalMarkets #ValuationStrategy #CFOInsights

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth

Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3

In this year-end episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman reflect on what it actually takes to build a modern media business around newsletters and podcasts. They unpack CJ’s first year going full-time, comparing creative intuition versus metric-driven operating styles, and discuss what content truly drives growth. The conversation also covers distribution dynamics, the emotional reality of unsubscribes and burnout, and closes with a candid look at monetization, team building, and the tradeoffs between simplicity and scale.

—

SPONSORS:

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

—

LINKS:

Mostly Metrics: https://www.mostlymetrics.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

https://www.growthunhinged.com/p/deep-research-for-gtm

https://www.growthunhinged.com/p/2025-state-of-b2b-gtm-report

https://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stack

https://www.mostlymetrics.com/p/the-great-ai-arr-illusion

https://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-report

https://www.mostlymetrics.com/p/download-the-annual-planning-bible

https://www.growthunhinged.com/p/how-to-sell-annual-plans

https://www.growthunhinged.com/p/get-recommended-by-chatgpt

https://www.growthunhinged.com/p/gtm-vibecoding-ideas

https://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing

—

RELATED EPISODES:

We get roasted for swag and drop some GTM gold

https://youtu.be/uubf_8al95w

Do vanity plates bring serious business?

https://youtu.be/Cm1rubFb-kg

Pricing in the Real World: Babies, Bots, and Billing

https://youtu.be/T1cjFSZR0k0

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:52 Sponsors — Pulley | Metronome

00:04:12 Action Figure Swag and Year-in-Review Setup

00:05:47 Going Full-Time and the First-Year Reality Check

00:07:24 Writing Schedules, Creative Work, and Time Optimization

00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality

00:10:51 Perfectionism vs. Throughput in Newsletter Writing

00:13:03 Creator Burnout, Motivation, and Engagement Anxiety

00:14:08 Playing the Long Game vs. Obsessing Over Metrics

00:15:42 Best Work of the Year and High-Leverage Content Bets

00:17:55 Big Research Reports as Career-Defining Projects

00:19:19 When Memes Outperform Deep Work

00:19:52 LinkedIn Algorithms vs. Content Quality

00:20:51 Writing for the Feed vs. Writing to Think

00:22:03 Optimizing LinkedIn Profiles for Credibility

00:23:47 Subscriber Growth, Audience Quality, and Churn Reality

00:27:20 Reports and Research as Growth Engines

00:28:37 Tactical “How-To” Content That Actually Converts

00:30:21 Tactical Value Beats Sounding Smart

00:30:40 Building a Team and Scaling Beyond a Solopreneur

00:32:05 Simplicity vs. Scale in Early Business Decisions

00:35:37 Avoiding Boredom and Shiny Object Syndrome

00:37:12 Balancing Writing, Consulting, and Energy

00:37:54 Making the Leap Financially as a Creator

00:39:01 Subscriptions vs. Advertising as the Real Business Model

#MostlyGrowthPodcast #CreatorEconomy #IndependentCreator #NewsletterBusiness #YearInReview

[Original air date: June 5, 2025]

How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his “center of the table” framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool.

—

SPONSORS:

Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.

Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt

Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.

—

LINKS:

Russell on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/

Tropic: https://www.tropicapp.io/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Wasted Capital and Where to Find It The CFOs Guide to Spoilage Levers Leakages

https://youtu.be/xOby7CcdljI

—

TIMESTAMPS:

00:00:00 Mostly Classics: Russell Lester on Capital and Alignment

00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares

00:04:07 Russell Lester Joins the Show

00:06:45 Capital Spoilage and Wasted Spend

00:08:34 Why Spoilage Goes Unnoticed Inside Companies

00:10:16 Creating Accountability for ROI

00:11:08 Spoilage Beyond Tools and Software

00:13:04 Strategy Drift and the Sunk Cost Trap

00:14:14 Sponsors — Sage Intacct | Mercury | RightRev

00:17:44 Levers and Leakages: A Framework for Momentum

00:19:27 Identifying Levers Across the Funnel

00:21:48 Efficiency Levers Inside the P&L

00:23:31 Common Spend Leakages in Practice

00:24:21 The Center of the Table Framework

00:26:47 Budget Ownership vs Corporate Stewardship

00:28:49 The CFO as Chief Alignment Officer

00:31:31 Trust, Tact, and Executive Leadership

00:33:35 Helicopter Skills for Finance Leaders

00:35:41 Curiosity as a CFO Superpower

00:36:02 Data Safaris and Asking Better Questions

00:38:16 Breaking Down Net Dollar Retention

00:40:32 Navigating Data Overload

00:42:16 Building a Single Source of Truth

00:43:03 Intelligent Spend Management in Action

00:44:44 Capital Allocation as the CFO’s Core Job

00:46:04 How Spend Management Drives Growth

00:49:14 Why Companies Delay Spend Tools

00:50:49 A Career Mistake with Investors

00:52:49 Auto-Renewals: Revenue vs Leakage

00:54:07 Advice to a Younger CFO

#RunTheNumbersPodcast #CFOLeadership #CapitalAllocation #FinancialStrategy #SpendManagement