In this episode of Run the Numbers, CJ sits down with Glenn Schiffman, CFO of Fanatics. They break down the economics of sports IP, how Fanatics approaches CAC, LTV, and capital allocation across merchandising, collectibles, and betting, and the negotiation lessons Glenn learned from decades in investment banking and leading finance at IAC.

—

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

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

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

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

—

LINKS: 

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

Guest: https://www.linkedin.com/in/glenn-h-s-51440521/

Company: https://www.fanaticsinc.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:13 Welcome and guest intro

2:38 Football at Duke and college businesses

5:40 Predecessor to DoorDash story

7:10 IP monetization explained

9:22 All deals are snowflakes

10:36 Partnership KPIs

13:21 Sponsors — Brex | Aleph | RightRev

16:40 Buy, bet, collect: CAC and LTV

17:15 Single view of the fan

18:39 Multi-business customers spend 4.7x

20:32 Fanatics credit card launch

22:13 AI for personalization

23:01 DTC vs. wholesale margin profiles

24:05 Budgeting process

26:07 Infinite vs. finite: focus on revenue

26:37 Sponsors — Rillet | EY | SpendHound

29:47 Starve your losers, feed your winners

32:58 Capital compounding: revenue, EBITDA, FCF

33:56 Buybacks at IAC

37:02 First negotiation at Lehman

39:17 Outlasting the other side

39:56 Listening in negotiations

40:03 Long-Ass Lightning Round

44:25 Credits

#RunTheNumbersPodcast #CFO #SportsCommerce #CapitalAllocation #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Kunal Agarwal, CFO of Gorgias, to unpack how AI is reshaping pricing and operations. They discuss outcome-based pricing, how to forecast LLM-driven costs, and why order-to-cash isn’t just back-office plumbing—it can be a true growth lever when designed correctly.

—

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: 

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

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

Company: https://www.gorgias.com/

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

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

—

TIMESTAMPS:

0:00 Preview and Intro

2:14 PE to venture incubator

4:39 Operational empathy from zero-to-one

4:45 First paying user feeling

5:40 Jet ski customer support story

8:49 Hanging with IC sales reps

12:24 Sponsors — Tabs | Abacum | Brex

15:44 Finance as the decision engine

17:36 Gorgias overview

20:20 Pricing structure and iteration

22:11 Outcome based / resolution pricing

24:48 AI success rate as key metric

25:33 Sponsors — Metronome | RightRev | Rillet

28:57 Pricing value split — $1 per resolution

31:17 Vertical specificity as AI moat

33:27 Managing LLM costs

35:41 Falling token costs and model mix

39:28 Order to cash as growth engine

43:31 Auditing order to cash at 25M ARR

44:09 Manual choke points

46:32 Learning density over titles

48:30 SurveyMonkey as the most formative period

50:07 Lightning round

50:17 Listening to respond vs. listening to learn

51:04 Advice to younger self

52:02 Finance software stack

52:45 Cortex — internal AI decision tool

54:21 Craziest expense story

54:52 Credits

In this episode of Run the Numbers, CJ sits down with Federico Acabbi, investment banker at RBC, to break down what’s happening across cybersecurity, infrastructure, and the broader software market. They cover why horizontal software is under pressure while security spend holds up, what it really takes to go public today, and how the IPO process actually works behind the scenes—from diligence to pricing.

—

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: 

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

Federico: https://www.linkedin.com/in/federicoacabbi/

rbccm.com

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

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

—

TIMESTAMPS:

0:00 Preview and intro

2:36 Software investability right now

6:46 Cyber — CFO's #2 investment priority

8:17 AI turbocharging attacks

9:08 DevOps disruption

10:30 Sponsors — Rillet | Tabs | Abacum

13:55 IPO landscape overview

14:33 Revenue and market cap benchmarks

19:24 Founder share sales at IPO

22:28 Secondary market vs. IPO market

23:14 How many IPOs can the market digest?

24:20 Investor mix for larger vs. smaller IPOs

25:04 Sponsors — Brex | Metronome | RightRev

28:23 Role of mutual funds in IPOs

30:00 What banks actually do on an IPO

31:49 Book building and allocation

32:43 Research coverage

35:52 NDRs and testing the waters

38:59 Roadshow format — then vs. now

40:41 Direct listings explained

43:57 How banks make money on IPOs

44:56 Fee splits between banks

47:36 IPO vs. M&A — which is more attractive?

51:02 Junior banking story — Nokia and the Vespa

54:31 Craziest expense story

56:08 Credits

In this episode of Run the Numbers, CJ sits down with financial historian and PayPal Mafia member Aman Varejee to explore the recurring patterns behind economic bubbles. Drawing on research from his upcoming book “A Brief History of Financial Bubbles”, Aman explains what defines a bubble, the psychology that fuels speculative manias, and why major technological shifts—from railways to the internet to AI—often coincide with periods of extreme market speculation.

—

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: 

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

Aman: https://www.linkedin.com/in/aman-verjee/

https://practicalvc.com/

Aman’s book: https://bigbubbletrouble.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:38 Welcome and guest intro

3:48 Defining a bubble

6:03 Cognitive biases behind bubbles

10:27 Sponsors — RightRev | Rillet | Tabs

13:56 Do bubbles produce breakthroughs?

14:35 Dot-com bubble — winners and losers

16:00 UK railway bubble

21:24 Bubble warning signs

25:30 Sponsors — Abacum | Brex | Metronome

28:47 Do bubbles attract grifters?

31:11 Role of government in bubbles

35:59 Bubble duration vs. severity

37:32 2008 — roots go back to 1992

40:27 Are bubbles connected through time?

43:38 Are we in an AI bubble?

45:06 Nvidia vs. Cisco valuation comparison

46:52 Circular finance in AI

49:16 FP&A at PayPal under Thiel and Musk

52:02 PayPal's referral campaign and LTV/CAC

54:40 Book plug

55:09 Credits

#RunTheNumbersPodcast #Fintech #EconomicBubbles #FinanceHistory #CFO

In this episode of Run the Numbers, CJ sits down with Jason Lee, CFO of Faire, to unpack the economics of wholesale marketplaces. They break down how Faire connects independent brands with local retailers, the key metrics that matter in marketplace businesses, and ROI as a decision-making framework. Jason also shares lessons from scaling Square through its IPO and how finance leaders navigate valuation resets in private markets.

—

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: 

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

Jason: https://www.linkedin.com/in/jason-lee-11787020/

Faire: https://www.faire.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

3:01 How Faire serves retailers

5:49 Revenue model and retention metrics

8:21 Recurring vs. reoccurring revenue

11:54 Sponsors — Metronome | RightRev | Rillet

15:17 Input vs. output metrics

17:13 The business equation

19:08 Metric ownership

22:07 Killing metrics: signal to noise

23:21 800 metrics at Faire

24:51 Customer count as a misleading metric

26:04 Sponsors — Tabs | Abacum | Brex

29:25 Planning cadences at Faire

32:41 When to reallocate resources

36:40 ROI as a framework

40:25 Portfolio view of investments

43:53 Discipline is knowing where to say yes

47:11 Faire's valuation reset

50:49 Tender offer mechanics

55:33 Screwing up IR at Square IPO

56:52 Advice to younger self

58:44 AI at Faire

59:32 Claude connected to data warehouse

1:00:16 Tariff analysis with AI

1:02:38 Credits

#RunTheNumbersPodcast #Marketplace #CFO #SaaS #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Mike Wilcox, CFO of Blockchain.com, to unpack the economics of crypto exchanges. They discuss how platforms serve both retail traders and institutional clients, the different ways exchanges generate revenue, and the tension between blockchain’s radical transparency and the valuable first-party data exchanges control.

—

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: 

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

Mike: https://www.linkedin.com/in/mike-wilcox-65078a12/

https://www.blockchain.com/

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

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

—

TIMESTAMPS:

Here's the trimmed version:

0:00 Preview and intro2:12 Tradfi to crypto transition3:49 Blockchain.com origin5:45 CFO as business partner6:01 Finance team backgrounds7:02 Banking relationships8:51 On ramps and off ramps8:51 Retail vs. institutional10:53 Sponsors — Brex | Metronome | RightRev14:09 B2C to B2B motion16:04 Shared infrastructure18:31 Go-to-market differences19:00 Brand equity and low CAC20:06 Education as top-of-funnel21:13 Institutional vs. retail volatility22:37 Exchange vs. brokerage model23:56 How brokerages make money24:06 Sponsors — Rillet | Tabs | Abacum27:31 Setting take rates29:13 Distribution flywheel30:13 Data as a moat31:13 Nigeria market playbook31:44 Crypto balance sheet33:25 Duration matching34:37 Transaction-level risk36:12 Latency arms race37:28 Stablecoins and CFOs38:13 Risk vectors40:01 Annual planning41:51 Lightning round43:00 Finance software stack43:31 Advice to younger self44:09 Credits

CJ sits down with Marshall Hawks, a 20-year veteran of venture lending and author of Venture Debt Deals. They cover the real rules of thumb behind deal sizing, why lenders underwrite likelihood of raising again (not breakout outcomes), how banks and private credit differ, the three real sources of repayment, and how to actually run a venture debt process without blowing your legal budget.

---

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:

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

Marshall: https://www.linkedin.com/in/marshallhawks/

Marshall's website: https://www.marshallhawks.com

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

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

TIMESTAMPS:

0:00 Preview and intro

3:23 Marshall's background and the book

4:47 Venture Deals as inspiration

6:30 Companies Marshall has worked with

6:49 The venture debt sweet spot

8:01 Why venture debt follows equity raises

10:55 The 25–40% rule of thumb

12:08 AI companies and the limits of the rule

13:58 Sponsors — Abacum | Brex | Metronome

17:15 How lenders think vs. investors

19:12 The three sources of repayment

21:37 Venture debt and the AI boom

23:52 Banks vs. private credit

26:28 Sponsors — RightRev | Rillet | Tabs

29:57 Private credit pricing and warrants

33:04 Syndicated deals

35:04 Legal timelines

38:13 Who pays the legal bill?

40:06 Why your GC shouldn't quarterback the deal

41:30 What forecast to give your lender

43:37 Reporting cadence

45:57 Bad news should travel fast

47:49 The Twitch case study

50:19 Are we over our skis in 2026?

54:50 Where to get Venture Debt Deals

55:09 Credits

In this episode of Run the Numbers, CJ sits down with Superhuman’s Head of Analytics Chris Byington. They break down where analytics should sit inside a company, why dashboards often fail, and how the best teams connect metrics, OKRs, and forecasting to real decisions. Chris also explains why “ship goals” can mislead teams and what CEOs and CFOs should expect from a truly decision-driving data function.

—

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: 

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

Chris: https://www.linkedin.com/in/chris-byington/

Superhuman: https://superhuman.com/

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

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

—

RELATED EPISODES:

Matt Hudson Episode

https://youtu.be/_FWGYkzhymQ

—

TIMESTAMPS:

0:00 Preview and intro

3:29 Centralized analytics team

7:29 Start analytics with problems not tools

9:41 Lead with the problem

10:14 Align on growth model

11:46 Pre-commit to decisions

13:14 Sponsors — Tabs | Abacum | Brex

16:35 Dashboards need growth context

19:10 Where analytics should sit

21:18 Pros and cons of analytics in finance

23:18 Operations vs revenue org placement

24:11 Hub-and-spoke analytics model

25:18 What “embedded” actually means

26:14 Sponsors — Metronome | RightRev | Rillet

29:38 When self-service analytics works

32:04 Self-serve pitfalls

33:44 Buy vs build BI

35:44 Analytics owns metrics

38:26 Hero metric example

41:41 Outcomes > shipping

42:14 Set goals before build

43:57 Metrics are outcome proxies

46:40 Easy way to say no

48:29 Start answers with yes

52:17 Proving analytics impact

56:19 Credits

#RunTheNumbersPodcast

In this episode of Run the Numbers, CJ breaks down the 5,000-year history of marketplaces—from Mesopotamia to Amazon—and the economics behind take rates, trust layers, and vertical unbundling. We unpack Airbnb’s fee backlash, Facebook Marketplace’s hidden value, why inventory kills platforms, and how AI will reshape discovery—without eliminating the middleman.

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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

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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

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

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

—

RELATED EPISODES:

The Mindshare Advantage Marketplace Success With Boris Wertz of Version One Ventures

https://youtu.be/kN61sAxw_yk

The Marketplace Plus Model Explained | Colin Gardiner of Yonder VC

https://youtu.be/VIWFVwCfyLE

A CFO Explains the History of EBITDA

https://youtu.be/JySZv_fSNqs

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TIMESTAMPS:

0:00 Preview

1:34 Marketplace Origins

2:48 The Digital Shift

5:55 Unbundling of Craigslist

9:56 Sponsors — Rillet | Tabs | Abacum

13:21 Smart Phone Revolution

17:33 Take Rate Calculations

21:08 When the Marketplace Crosses the Line

24:49 Sponsors — Brex | Metronome | RightRev

28:09 When Fees Become Friction

30:37 The Marketplace Plus Model

33:26 The $100B Flea Market

36:14 The Inventory Trap

40:07 The Disintermediation Problem

42:35 Convenience Beats Inspection

45:09 AI Compresses the Marketplace

47:56 You Can’t Cut Out the Middleman

50:03 Credits

#RunTheNumbersPodcast #Marketplaces #PlatformEconomy #Middleman #TechStrategy

CJ sits down with Mike Jung, Co-Founder and Managing Partner of Founders Circle Capital. They unpack the rise of structured liquidity, how secondaries went mainstream, and what CFOs should know before running a tender. Mike shares lessons from the dot-com era, AI’s “super cycle,” and what separates durable growth companies from hype.

—

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: 

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

Mike: https://www.linkedin.com/in/mikjung

https://www.founderscircle.com/

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

https://www.mostlymetrics.com

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TIMESTAMPS:

1:08 Founder Circle origin

3:15 The founder liquidity insight

5:16 Staying private longer problem

6:04 Secondary market control vs chaos

8:44 Secondaries over IPOs

10:12 Liquidity keeps VC alive

11:27 Ask Jeeves dot-com lesson

12:26 $190 to $1 + AMT reality

13:10 Sponsors — RightRev | Rillet | Tabs

16:39 Private share opacity risk

20:25 Founder + employee liquidity playbooks

21:55 Early investors need liquidity too

22:31 Cap table math actually matters

24:17 SPV fee stacking insanity

25:37 Sponsors — Abacum | Brex | Metronome

28:54 Tender offer guardrails

30:09 Minimum vs maximum liquidity balance

33:01 Growth stage sweet spot + IPO bar rising

34:17 AI Cambrian explosion

34:58 Buying fear vs buying hype

36:29 AI growth sustainability

37:19 Founder-led advantage + product velocity

38:47 TAM is created, not measured

41:06 Anti-portfolio lessons

43:01 What is a supercycle

44:34 Do supercycles end in crashes?

46:16 AI’s unprecedented adoption curve

48:31 Community as a moat

52:50 Earning the right to be on the cap table

In this episode of Run the Numbers, CJ sits down with Mateo Bryant, CFO of Minted. They break down Minted’s life-event flywheel and decades-long LTV, managing extreme seasonality when half the year happens in one month, and balancing long-term CAC with short-term monetization. Mateo also shares lessons from scaling Uber and Amazon globally, localization missteps, and making marketplaces work in emerging markets.

—

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: 

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

Mateo: https://www.linkedin.com/in/bryantmatt/

Minted: https://www.minted.com/

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

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

—

RELATED EPISODES:

Peter Oey, CFO of Grab:

https://youtu.be/tdq0AZO0dLU

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TIMESTAMPS:

00:00 Intro

03:16 Fixer to CFO

05:32 Mexico City Startups

09:00 Minted Flywheel

10:24 LTV Expansion

11:04 Entry Points

12:18 CAC and Cohorts

13:42 Sponsors: Metronome | RightRev | Rillet

17:06 Wedding Lifecycle

19:49 Holiday Forecasting

22:23 Retail Calendar

24:03 Cash Flow Swings

25:05 Marketing Over Sales

26:06 Email Limits

27:41 Sponsors: Tabs | Abacum | Brex

31:02 Retail Strategy

35:08 Global Experience

40:47 Uber Cash Economics

46:04 Cost of Not Localizing

50:19 Importer of Record

53:17 No Google Lesson

55:34 QBR Mistake

56:48 High Leverage Hours

59:03 Finance Stack

59:50 Seven Day Cruise Expense

#RunTheNumbersPodcast #MarketplaceStrategy #EcommerceFinance #GigEconomy #CFOInsights