Run the Numbers

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.

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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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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

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LINKS: 

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

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

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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

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.

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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

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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

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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

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.

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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/

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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

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RELATED EPISODES:

Adam Swiecicki - CFO of Rippling

https://youtu.be/JyGJVpmZNac

Aurélien Nolf - CFO of Navan

https://youtu.be/siwzJSRXAvY

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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.

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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

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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

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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.

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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

https://youtu.be/ZL6AbqHI-0g

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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.

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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

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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

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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

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. 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.

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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

—

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

On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.

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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 an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

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 cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

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LINKS: 

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

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

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

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TIMESTAMPS:

0:00 Preview and Intro

3:27 Alex Immerman's favorite CFO interview question

4:54 What a weak answer looks like

5:26 When the hard calls actually matter

6:37 Walt and Roy Disney

7:36 Liked even when making unpopular calls

8:43 Sponsors — Anrok | RightRev | Pulley

11:35 Curt from Clio: ego in the bottom drawer

13:52 CFO as supporting cast

15:10 Backbone vs. ego: when to use each

16:23 Daniel Kang: don't use the purse strings as power

17:36 Earn the seat, don't demand it

18:52 Money is one arrow, not the whole quiver

20:39 Sponsors — Rillet | Maximor | Brex

23:54 Adam Ante: finance people pigeonhole themselves

26:46 The CFO can sit in any meeting

27:30 First 90 days: listen before suggesting

28:46 David Laptor: listen, observe, think, speak

30:50 Build a culture where speaking up is welcomed

31:51 Curt from Clio: don't come in as a know-it-all

33:08 Earn trust through curiosity

33:46 Beware of all-green dashboards

35:28 What would CJ say to Ballmer?

37:14 Parting thoughts from Ben

38:00 Credits

On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.

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SPONSORS:

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. 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 an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

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 cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

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LINKS: 

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

Guest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/

Company: https://www.datadoghq.com/

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

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

—

TIMESTAMPS:

0:00 Preview and Intro

2:42 FP&A as a product team

4:53 The five pillars of AJ's team

6:39 How far FP&A has come

7:33 How do you know you're doing a good job?

10:20 FP&A as the dashboard, not the engine

10:20 Sponsors — Brex | Anrok | RightRev

13:18 The four-stage FP&A maturity model

16:00 Can you reach all four stages at Series B?

16:45 Why AJ holds weekly forecast meetings

18:24 How often to actually change the forecast

21:42 Sponsors — Pulley | Rillet | Maximor

24:49 Single source of truth: still on the vision board

26:12 AI and the self-serve data risk

26:21 CAC payback over LTV to CAC

29:39 Inside sales vs. enterprise payback comparison

31:47 Finance as the yes, but people

34:02 FP&A vs. IR: which is harder?

36:14 How IR makes you a better FP&A leader

37:19 Is the IR profile shifting?

42:01 IPOs are branding events, not finish lines

43:27 The Datadog IPO during the WeWork meltdown

45:15 Career philosophy: do great work where you are

49:52 Datadog didn't have a role for AJ when he started

52:16 Lightning round

52:24 Screwed up: forgot the currency guy

54:37 Finance software stack

56:16 Advice to younger self

57:13 Credits

On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market.

—

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 cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. 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 an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

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

Guests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/

Company:https://practicalvc.com/

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

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

—

TIMESTAMPS:

0:00 Preview and Intro

3:00 Writing as a distribution strategy

5:17 How Dave's blog led to Founders Fund

7:24 Aman: writing at PayPal and law school

9:29 PayPal: the red pen of David Sacks

11:44 Sponsors — Rillet | Maximor | Brex

14:59 500 Startups: the original thesis

16:22 The volume strategy: more shots on goal

18:44 Twilio, Lyft, Sendgrid, Credit Karma

20:15 60x returns: right place, right time

23:07 Sponsors — Anrok | RightRev | Pulley

25:58 Accelerator ecosystem evolution

28:42 500 vs. YC: scale as a weapon

32:52 Globalizing the accelerator model

35:04 Seed to secondaries: how it happened

37:00 Scratching their own itch for liquidity

38:10 The secondary market explained

40:50 Types of secondaries

43:29 Why would a VC sell a winner?

46:07 Managing DPI as a late-stage manager

47:02 The five horse framework

49:15 Skipping the J curve

51:44 Imperfect information as a feature

55:22 Landmines: fraud, mismarked valuations

57:00 VCs lie about valuations three ways

57:58 Forward contracts and counterparty risk

1:00:29 Credits