Run the Numbers

In Part 3 of our Token Series with Tabs, CJ and Ali Hussain ask who’s actually paying for AI. They cover the venture-funded subsidy behind today’s AI prices, why more companies are passing token costs on to customers, and how pricing is shifting toward hybrid commits, tiers, and credits. They also dig into overages, revenue leakage, and agentic commerce.

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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

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LINKS:

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

Guest: ⁠⁠⁠⁠linkedin.com/in/ali-hussain786⁠

Company: ⁠⁠www.tabs.com⁠

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

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

0:00 Cold Open

1:16 Who Foots the Bill for AI?

1:25 The Venture Subsidy

1:54 Sizing AI Spend

2:50 The Uber Analogy

4:50 Passing AI Costs Through

5:43 Will Buyers Go Cheaper?

7:17 Pricing and Packaging

8:18 Hybrid Commits

9:31 Where Tiers Fit

10:34 What Is a Credit?

12:42 The Overage Problem

14:51 Agentic Commerce

17:30 Next Up: Tokens as Currency

#RunTheNumbersPodcast #AIPricing #UsageBasedPricing #CFO #AI

In this episode of Run the Numbers, CJ sits down with Brian Neider of Lead Edge Capital, author of the viral “Hierarchy of Metrics Bullshit.” They cover how to spot misleading metrics, the difference between a good company and a good investment, and the worst EBITDA add-backs. They also look at how AI is changing software defensibility, and Brian tells the story of the giant Happy Gilmore check.

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SPONSORS:

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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 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

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LINKS:

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

Lead Edge Capital: https://leadedge.com/

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

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

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TIMESTAMPS:

0:00 Cold Open

2:37 Origin of the Hierarchy of Metrics

4:37 Token Maxing: Today’s Page Views

5:29 What CEOs Get Cagey About

10:07 Selling Well vs. Intellectual Dishonesty

15:26 Asking “Explain It Again”

19:11 Good Company vs. Good Investment

23:25 Defining “Expensive”

24:32 Better Questions with EY

24:50 EBITDA Add-Backs

28:22 Revenue vs. EBITDA Multiples

29:28 The Craziest Add-Backs

35:15 Is Services Revenue Good Revenue?

39:28 Horizontal, Vertical, Infrastructure

41:44 How AI Hits Each Category

45:06 Moats

52:17 The Happy Gilmore Check

#RunTheNumbersPodcast #LeadEdge #EBITDA #VentureCapital #AI

In this episode of Run the Numbers, CJ breaks down Anthropic’s S-1: the revenue growth, 900% net revenue retention, compute costs, gross margin, and whether the company is actually profitable. We also cover the risk factors, the five-class share structure, executive pay, and what a roughly $2 trillion valuation implies next to other recent IPOs.

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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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.

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

—

LINKS:

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

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

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

—

TIMESTAMPS:

0:00 Cold Open

1:08 Ticker, Raise, and Valuation

2:02 Three Big Questions

2:21 Key Stats at a Glance

8:04 The Best Shareholder Letter Ever

11:18 Where Anthropic Sits in the AI Stack

15:20 How Anthropic Makes Money

18:02 Run Rate vs. ARR

20:56 Revenue Efficiency

22:48 The Four Financial Drivers

25:16 Are They Profitable?

26:37 Gross Margin

31:29 Cash Flow

35:22 Wallet Share and Too Many Partners

37:18 Red Flags

40:49 The Cap Table

42:08 Exec Pay and the Board

43:33 Valuation

44:50 IPO Comps

45:12 Odds and Ends

45:55 Bull Case and Final Take

46:57 Wrap Up

#RunTheNumbersPodcast #Anthropic #IPO #S1 #AI

In this episode of Run the Numbers, CJ welcomes back Sid Kumar, who has led go-to-market through perpetual, cloud, SaaS, and consumption models at CA, AWS, HubSpot, and now Databricks. They cover how consumption changes the sales org, why customer success has an identity crisis, how to build a commission stack, and what ARR actually means. Sid also shares how AI is reshaping capacity planning and why he thinks annual planning is giving way to continuous planning.

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SPONSORS:

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

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

—

LINKS:

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

Craig on Linkedin:https://www.linkedin.com/in/craig-bealmear-a375573/

Oklo:https://oklo.com/

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

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

—

TIMESTAMPS:

0:00 Cold Open

2:52 Go-to-Market

5:05 Perpetual, SaaS, Consumption

7:01 The Contract Isn’t the Moment of Truth

10:24 A Different Kind of AE

17:41 Customer Success’s Identity Crisis

20:23 Hunter vs. Farmer

22:44 Motion Specialization

23:50 Building the Commission Stack

28:07 CAC and LTV

29:54 What ARR Means

33:44 Pattern Matching With Data

38:13 Forecasting

38:59 Always Be Planning

41:10 AI and Capacity Planning

43:48 Will AI Change Sales Ops?

46:16 The Player-Coach Is Back

46:44 Getting Hands-On With AI

48:08 Hot Take on Annual Planning

#RunTheNumbersPodcast #Databricks #GoToMarket #SalesOps #ConsumptionPricing

In this episode of Run the Numbers, recorded live at Brex Mode in Chicago, CJ sits down with Craig Bealmear, CFO of Oklo, who spent nearly 30 years at BP before moving into nuclear. They cover raising billions before meaningful revenue, why cash matters more than the P&L, and how he hires the finance team Oklo will need two years from now. Craig also looks back at leading through the Deepwater Horizon crisis.

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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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.

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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

—

LINKS:

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

Craig on Linkedin:https://www.linkedin.com/in/craig-bealmear-a375573/

Oklo:https://oklo.com/

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

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

—

TIMESTAMPS:

0:00 Cold Open

2:38 What Oklo Does

3:38 From BP to Nuclear

6:03 The Power Behind the AI Stack

7:47 Unconstrained Demand

12:38 Risks

13:50 Running a Pre-Revenue Company

14:57 The Say-Do Ratio

17:41 Asking the Dumb Questions

18:13 Raising Capital Before the Projects

21:15 Cash Management Pillars

25:05 One-Way vs. Two-Way Decisions

26:11 Defining Capability

27:35 Hiring for Two Years Out

28:07 Forecasting the Team 8 Quarters Out

30:07 Deepwater Horizon

31:46 Leading Through a Crisis

32:19 Wrap Up

#RunTheNumbersPodcast #Oklo #Nuclear #CFO #BrexMode

In Part 2 of our Token Series with Tabs, CJ and Ali Hussain ask how much AI is too much in finance. They cover why finance may be the most AI-forward function after product and engineering, how MCP became its “ChatGPT moment,” and why headless agents need a leash. They also get into where to start with governance and why deterministic layers still matter.

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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

—

LINKS:

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

Guest: ⁠⁠⁠⁠ linkedin.com/in/ali-hussain786⁠

Company: ⁠⁠ www.tabs.com⁠

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

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

—

TIMESTAMPS:

0:00 Cold Open

1:05 Why CFOs Ask About Org Design

2:25 Finance Is the Most AI-Forward Team

3:43 MCP: Finance’s ChatGPT Moment

5:08 Laying Tracks for Agents

5:53 Vendors, Employees, Customers

6:51 MCP, Harnesses, and Headless Agents

8:34 The New Finance Operating System

11:50 Governing AI in Finance

12:12 Where to Start: Billing and Collections

13:51 Will Deterministic Layers Survive?

14:51 Build vs. Buy

16:28 Why Revenue Work Is So Hard

18:11 Next Up: Who Foots the Bill?

#RunTheNumbersPodcast #Tabs #CFO #AI #AITokens

Episode Description:

In this episode of Run the Numbers, CJ sits down with Erica Dorfman, CFO of Brex, to trace her path from capital markets at SoFi to product to the CFO seat. They cover why Brex moved away from lending, what happened behind the scenes during the SVB collapse, and how Erica keeps reinventing her role and her team as the company scales.

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SPONSORS:

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://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

—

LINKS:

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

Erica on Linkedin: https://www.linkedin.com/in/erica-dorfman-4034b717/

Brex: http://www.brex.com

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

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

—

TIMESTAMPS:

0:00 Cold Open

2:24 Swimming and the CFO Mindset

6:03 The Columbia Finance Mafia

7:48 The Physics of a Business

11:16 VP of Cash at Brex

12:40 How Banking Partnerships Work

17:58 Why Brex Moved Away From Lending

19:23 Great Adjacency vs. Distraction

21:31 AI Auditing Every Transaction

23:00 Operating Through Chaos at SoFi

25:45 The SVB Weekend

29:00 Crisis Meets Opportunity

37:31 Asking “Stupid” Questions

39:44 Rebuilding the Team

43:33 Killing Meetings

46:05 Erica’s Biggest Mistake

47:08 Advice to Her Younger Self

47:36 Brex’s Finance Tech Stack

48:37 Craziest Expense Ever

#RunTheNumbersPodcast #Brex #CFO #Building #FinanceLeadership

In this episode of Run the Numbers, CJ welcomes back Jim Cook, a multi-time CFO (Intuit, Netflix, Mozilla) turned coach, author, and newsletter writer. They dig into “return on compute,” the metric Jim believes every finance leader needs in their vocabulary, and why surprise AI bills echo the early days of the cloud. They cover how to budget for tokens, the “frontier convergence” idea for ramping compute spend by role, and why revenue per compute may join revenue per headcount on the CFO scorecard.

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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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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 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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

—

LINKS:

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

Jim on Linkedin: https://www.linkedin.com/in/cookflix/

Benchboard: https://www.benchboard.com/

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

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

—

TIMESTAMPS:

0:00 Welcome Back, Jim Cook

2:56 Return on Compute

5:51 The $500K Surprise Bill

8:25 Do Execs Know Their Token Usage?

10:05 Tagging Compute Like Cloud Costs

12:03 Budgeting for Tokens

13:19 Revenue per Compute

14:45 The Modern CFO Framework

15:50 What Strategy Really Means

17:44 Communication and Influence

22:27 Lead With a Thesis

24:05 Speaking Up in the Boardroom

26:04 Better Questions with EY

28:11 Where to Find Jim

#RunTheNumbersPodcast #ReturnOnCompute #CFO #AI #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Heidi Robinson, former CFO and COO of Food52, for one of the wildest CFO stories the show has featured. Heidi joined expecting to lead a modest turnaround and within weeks realized the company was in far deeper trouble than anyone understood. She walks through being the newest executive in the room and having to deliver that news and the Monday evening a lender swept the company's cash without warning.

—

SPONSORS:

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com

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

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.

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 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

—

LINKS:

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

Guest: linkedin.com/in/heidilrobinson

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

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

—

TIMESTAMPS:

0:00 Cold Open

2:29 Joining Food52

3:45 Food52's Three Brands

6:14 Building a Cash Flow Model

7:25 Delivering the Worst News

8:09 A Path Without Bankruptcy?

9:05 The Cash Sweep

13:44 The Scramble

18:30 Selling at 60% Off

19:45 Working Through the Holidays

20:10 Filing Chapter 11

21:48 Chapter 7 vs. 11

23:05 The Headline Objective

23:33 The Stalking Horse Bidder

26:17 Meet the Cast29:41 Testifying Under Oath

30:50 The Independent Board Member

35:27 The Live Auction

39:06 Bidding Like Poker

40:50 The Payout Waterfall

44:24 Better Questions with EY

44:41 Rethinking Risk

46:00 CFO/COO Convergence

#RunTheNumbersPodcast #CFOs #Food52 #Bankruptcy #FinancePodcast

In this episode of Run the Numbers, CJ sits down with Shiv Verma, CFO of Robinhood, to unpack the company's 2022 "refounding". They dig into why Shiv personally signs off on every headcount and marketing dollar at a $100B+ company, and how Robinhood's capital allocation philosophy — no loss leaders, minimal variable costs, and a hard $100 million ARR bar for new products — shapes everything from prediction markets to private-market investing.

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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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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

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LINKS:

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

Guest: https://www.linkedin.com/in/shiv-verma-6408249/

Company: http://www.robinhood.com

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

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

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TIMESTAMPS:

0:00 Intro

2:21 The 2022 Refounding

8:46 Using NPS

17:53 Moving to a GM Model

19:58 Finance Partners

17:49 Killing Committees for DRIs

20:04 Headcount Requests

27:02 RPM Teams and Efficiency

32:27 The Art of Capital Allocation

33:34 Core, Scaling, and New Seeds

37:07 Funding a New Idea

38:17 Killing OKRs

44:59 No Loss Leaders

48:36 Building Prediction Markets Fast

51:26 Why Shiv Hates Variable Costs

53:37 Market Share Over Revenue

55:59 Forecasting a Volatile Business

59:53 Shiv's Biggest Mistake

1:02:03 Lessons from the Oakland A's

1:04:04 Advice to His Younger Self

1:04:48 Finance Tech Stack

1:05:30 Craziest Expense

This is Part 1 of our new Token Series with Tabs. CJ calls up Ali Hussain to dig into one of the fastest-growing, least-understood line items on the P&L: AI inference and token spend. They debate whether AI costs ultimately belong to the CTO or the CFO, why the shift from "experimentation budgets" to real operating costs is forcing companies to rethink ownership, what's actually different about AI spend compared to the early cloud transition, and how tools like OpenRouter (acquired by Stripe) and Ramp's new offering are approaching the problem from opposite ends of engineering vs. finance.

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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

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LINKS:

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

Guest: ⁠https://www.linkedin.com/in/ali-hussain786/

Company: ⁠www.tabs.com

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

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

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TIMESTAMPS:

0:00 Cold Open

1:11 From Experimentation Budgets to Real AI Costs

2:43 Who Owns AI Spend Inside a Company?

4:12 Lessons from the Cloud Transition

5:55 Why AI Costs Are Different from Cloud

7:51 AI as "Electricity Through the House"

8:42 Paying for 5 to 10 LLM Providers

9:58 OpenRouter vs. Ramp: Two Approaches

11:47 What the Finance Stack for AI Spend Should Look Like

13:34 Passing AI Costs on to Customers

In this episode of Run the Numbers, CJ sits down with Emily Man of Primary Ventures to map out where value actually accrues in the AI economy. They break down the 5 layers of the AI stack and why Emily believes the next era of AI adoption will be driven by diffusion through apps rather than smarter models alone.

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SPONSORS:

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made.

Go to abacum.ai/mostly-metrics.

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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

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

—

LINKS:

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

Guest: https://www.linkedin.com/in/emily-man-02a1a486/

Company: https://www.primary.vc/

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

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

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TIMESTAMPS:

0:00 Cold Opens

1:12 Meet Emily Man, Primary Ventures

2:01 What's Exciting in Venture Right Now

3:09 The 5 Layers of the AI Stack

4:08 Where Funding Has Focused So Far

5:54 Diffusion Through Apps

9:30 "Enough" Intelligence

17:11 Payroll vs. Compute Ratio

23:01 Alex Karp and "Owning Your Weights"

24:05 On-Prem vs. Cloud, Again?

30:53 Models vs. Loops

32:34 Software Goes Headless

34:14 Pre-2022 SaaS Companies

36:29 The Roadkill Bucket

41:42 The Vibe-Coding Backlash

44:55 Objectivity vs. Subjectivity

48:03 When AI Agents Talk to Each Other

49:43 Creating Alpha Without Being AI-Native

51:01 Better Questions, Brought to You by EY

51:16 The Future CFO Tech Stack

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

In this episode of Run the Numbers, CJ sits down with Todd McElhatton, CFO of Zuora, for a deep cut on pricing, packaging, and value in the age of AI. They dig into how companies are figuring out whether to charge for AI at all, why token-based budgets are starting to sit alongside headcount budgets, and why AI may be increasing — not decreasing — the value of deep expertise.

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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

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.

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

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out http://www.fidelityprivateshares.com

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 athttps://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to http://www.cloudcapital.co

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

—

LINKS:

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

Guest: https://www.linkedin.com/in/todd-mcelhatton-2140761/

Company: http://www.zuora.com

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

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

—

TIMESTAMPS:

0:00 Intro

1:15 Meet Todd

2:24 Debating Price

7:33 Is Software "Going Headless"?

9:18 Is AI Increasing the Value of Experts

9:58 Hiring Specialists vs. Generalists

16:49 Rethinking the Budget Envelope

26:56 Time to Value

31:20 Forward-Deployed Engineers

35:20 Parallels Between On-Prem-to-Cloud

36:10 Rethinking Strategy

37:07 Avoiding the Sunk Cost Trap

38:58 The Art of Pivoting

40:12 VMware

41:31 Experimenting With AI

42:33 What Private Boards Bring

43:13 Short-Term Pain

43:45 One-Way Doors vs. Two-Way Doors

44:57Long-Ass Lightning Round

45:04 Biggest Career Mistake

45:36 Advice45:56 Finance Tech Stack

46:43 The Craziest Thing Expense

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

CJ sits down with Lauren Dillard, CFO of LiveRamp, whose path to the CFO seat ran through investor relations, communications, and even a year as interim CMO. They dig into why storytelling and influence matter as much as technical finance chops, how LiveRamp tore down and rebuilt its entire commercial model — collapsing 25+ usage metrics into 5 and inventing the "token" along the way.

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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

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 athttps://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 athttps://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/

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

—

LINKS:

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

Guest: https://www.linkedin.com/in/lauren-russi-dillard-25502424/

Company: https://www.liveramp.com

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

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

—

TIMESTAMPS:

0:00 Cold Open

1:18 Intro

1:29 Meet Lauren Dillard

4:48 Lauren's Path to CFO

5:06 The "Wrong" Career Move

7:48 Why Storytelling Matters

9:41 Turning the Answer Into Action

10:33 People Plus AI

14:50 Pricing Is a Strategy Exercise

16:43 Rebuilding a Commercial Model

22:29 Simplifying Quote-to-Cash

23:29 Where the "Token" Came From

28:48 Selling a New Pricing Model

29:27 Balancing New Logos

30:17 Upmarket or Downmarket?

34:17 Where Finance and HR Disagree

36:07 The Biggest Mistake

38:23 Will It Make the Boat Go Faster?

42:27 Lessons from the NBA

44:25 Lauren's Biggest Misstep

46:27 Finance Tech Stack

47:42 Craziest Expense

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

Nscale just filed its S-1 to go public on the NYSE — and it might be the wildest IPO filing of the year. This UK-based "NeoCloud" is only 2 years old, is gross margin negative, started life as a crypto miner, and has somehow locked up over $100 billion in contracted value from Anthropic and Microsoft. CJ breaks down the entire S-1 line by line: what a NeoCloud actually is, how Nscale's "power to token" strategy works, why Nvidia shows up as its supplier, investor, guarantor, AND customer, and whether this is a durable business or a well-timed arbitrage on the AI compute shortage.

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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 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

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 athttps://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

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 athttps://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

—

LINKS:

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

Company: https://www.nscale.com/

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

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

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TIMESTAMPS:

0:00 Cold Open

0:53 Intro: Nscale Files to Go Public

2:40 WTF Is a NeoCloud?

4:11 The 5 Layers of the AI Stack

5:55 Landlord vs. Hotel: Nscale's Two Businesses

7:21 How Take-or-Pay Contracts Work

8:28 Sponsor Break

11:43 Breaking Down the Financials

15:37 What's a Contract Actually Worth?

18:45 Is This Just Nvidia Vendor Financing?

20:58 Sponsor Break

22:54 Medium-Term Arbitrage or Durable Company?

24:30 5 Potential Red Flags

27:08 How Does the CEO Get Paid?

28:04 Who's on the Board?

28:26 Is This the CoreWeave of the UK?

31:09 Miscellaneous Filing Oddities

33:31 Final Take

#Nscale #IPO #NeoCloud #S1Breakdown #AIInfrastructure

In today’s Run the Numbers, CJ sits down with Blake Saunders, founder and managing director at Core Advisors (an investment bank focused on media) and founder of The Joint, to go deep on how media companies actually make money — and how that's changing fast.

If you're anywhere near advertising, media, or content monetization, this one's a masterclass.

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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 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

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 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

—

LINKS:

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

Guest: linkedin.com/in/blakesaunders

Company: https://coreadvs.com/

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

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

—

TIMESTAMPS:

0:00 Cold Open and Intro

1:17 Welcome Back: Meet Blake Saunders

3:11 What Does "Media" Even Mean Today?

3:24 AI and LLMs

6:13 How Media Companies Make Money

7:32 Subscriptions vs. Ads vs. Events

8:54 Why Events Are the Riskiest Ad Dollar

9:48 B2B vs. B2C

14:25 Why Advertising Gets Such a Bad Rap

17:58 The Hulu Paradox

20:50 Built to Hold vs. Built to Sell

27:10 Content Decay and the Monetization Mismatch

29:08 Are IP Libraries Becoming Valuable

34:39 How Big-Name Podcast Deals Get Structured

37:50 Bundling, Unbundling, and Subscription Fatigue

39:08 The Bending Spoons Trade

40:20 Inside a Private Equity Value Creation Plan

41:56 The Content-to-Commerce Playbook

44:50 How Narrative-Driven Is Media M&A?

46:49 7 Moments a Deal Feels Dead

49:00 Farewell

CJ sits down with multi-time CFO Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale, to break down what actually happens when you sell a company. They cover why buyers value some businesses on ARR and others on EBITDA (and why being slightly profitable can hurt you), how to negotiate banker fees, what buyers find when they dig into your balance sheet, and why every cap table Rick inherits is wrong.

—

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

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 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

—

LINKS:

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

Guest: https://www.linkedin.com/in/rick-smith-906939/

Company: https://www.linkedin.com/company/bonfire-advisory

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

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

—

TIMESTAMPS:

1:21 Meet Rick Smith and "Six Months to the Sale"
2:44 Why Teach M&A Through Fiction
4:26 CEO/CFO Tension
7:08 Botching the Announcement
8:15 How Staff Really React
9:18 When Personal Life Collides With a Deal
13:50 ARR vs. EBITDA
17:58 What to Optimize Before a Sale
18:50 Churn and Contract Renewal
20:43 Strategics vs. PE
27:46 Investment Banker Fee Structures
29:09 What's Negotiable
29:56 The Realtor Problem
34:53 Big 4 vs. Regional Firms for Audit and QoE
35:47 Negotiating Accounting Fees
37:47 Deferred Revenue
41:23 Warrants, Options, and Carta Cleanup
44:02 QSBS: What CFOs Need to Know
45:28 Quality of Earnings: Who Pays and Why
47:44 What a QoE Actually Digs Into
51:22 Why Deal Momentum Is So Hard to Stop
53:47 The Waterfall
58:19 Who Keeps Their Job
61:31 Why Selling CFOs Feel Intimidated
62:56 Prospect Theory
65:28 Where to Find the Book

#RunTheNumbersPodcast #MandA #CFOLife #SellingACompany #QualityOfEarnings

CJ Gustafson sits down with Nigel Glenday, CFO and COO of Masterworks, to talk about how AI is actually changing day-to-day finance work. They cover why context matters more than model choice, how Nigel runs a dozen Claude Code terminal sessions at once, and how his team solved a 300,000 K-1 problem with Python instead of a $300K tool. Plus: a detour into the 2026 art market and what securitizing fine art teaches you about scarcity and pricing power.

—

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 athttps://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 athttps://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 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

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

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LINKS:

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

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

Company: https://www.masterworks.com/

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

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

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RELATED EPISODES:

Nigel's Previous Episode: ⁠⁠⁠https://www.youtube.com/watch?v=zfmqwIzM0P4&t=9s⁠⁠⁠

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TIMESTAMPS:

2:04 The Dinner Story: AI as Leverage

7:27 AI and the Value of Human-Curated Creativity

12:16 Why Context Beats Intelligence

14:11 What "Context" Actually Means for AI

16:50 Building a Knowledge Map

18:50 Why CFOs Are Uniquely Positioned to Encode Context

21:36 Making Data Cheap to Access

28:55 Claude Code Over the Web App

30:49 Building "The A-Team"

35:24 Solving 300,000 K-1s with AI and Python

42:26 Asking Better Questions Segment

42:50 Adopting Campfire

44:20 When Human Writing Beats AI

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

How did Oura turn a tiny piece of wearable hardware into a $1.4 billion business? CJ breaks down the numbers behind Oura’s IPO filing and the surprisingly powerful business model hiding behind the ring.

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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 athttps://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 athttps://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/

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

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

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

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TIMESTAMPS:

0:00 Oura Files S1

2:24 Key Revenue Stats

3:35 Revenue Per Ring

4:14 Gross Margin Breakdown

5:31 The Weird $924M "Net Loss"

6:11 Adjusted EBITDA and Cash Position

7:20 Headcount and Bankers

11:01 What Oura Actually Does

13:46 Go-to-Market Channels

15:57 Why Oura Rejects the "Fitness Tracker" Label

16:49 Who's Actually Buying It

21:26 Global Penetration Is Still Low

21:54 The $84M Battery Problem

22:56 Aggressive Growth Spend

24:16 Samsung's Patent Complaint

25:00 The Sleep Accuracy Class Action

25:17 Former CEO Lawsuit

25:52 Customer Concentration Risk

26:31 Supply Chain and Tariff Exposure

27:07 Clean Governance, No Material Weaknesses

27:20 The Cap Table

27:44 Oura's Massive Stock Buybacks

29:29 The RSU Vesting Mechanics

30:34 Tax Withholding on Settlement

31:07 Valuation: $16B at 11x Revenue

31:34 Who Do You Comp Oura To

32:34 Miscellaneous Filing Details

33:14 Final Take

In this episode of Run the Numbers, CJ sits down with Matt Hedberg, a sell-side equity analyst at RBC who has covered software for more than 20 years. They break down how AI compares to the cloud transition, why traditional software moats are changing, what separates management teams that will actually capitalize on AI, and why cash, customer relationships, data, and technical leadership matter more than ever.

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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 athttps://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 athttps://www.rillet.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/matt-hedberg/

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

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

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RBC Capital Markets: This content is based on information available at the time it was recorded, and is for informational purposes only. It is not an offer to buy or sell, or a solicitation, and no recommendations are implied. It is outside the scope of this communication, to consider whether it is suitable for you, and your financial objectives. For Required Conflicts Disclosures, see: https://www.rbccm.com/GLDisclosure/PublicWeb/DisclosureLookup.aspx?entityId=1. For Disclaimer, see: https:/http://www.rbccm.com/en/policies-disclaimers.page.