Run the Numbers

In this episode of Run the Numbers, CJ sits down with Jay Ritter. They break down what Apple, Nvidia, the dot-com boom, and today’s AI giants can teach us about IPOs, why companies leave money on the table on day one, why firms stay private longer, and what the data actually says about long-term IPO performance.
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SPONSORS:
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/jay-ritter-1323861/
Company: https://www.ufl.edu/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:10 Meet Jay Ritter, Mr. IPO
4:02 The Original 1983 Question
5:08 PCs, Internet, and AI Compared
9:36 Network Effects
14:46 Sitzfleisch: Outlasting the Field
16:10 Where Have All the IPOs Gone
23:29 IPOs as Relationship-Building
26:31 Why Investors Tolerate Founder Control
29:16 Dual-Class Stock's Origins
30:21 How Jay's Thinking Evolved
31:36 Why Boards Don't Get Angry
34:39 Banks' Real Client: Institutions
37:08 Book Building
38:56 Why Direct Listings Haven't Taken Over
39:57 What Goldman Is Really Selling
41:57 Sentiment vs. Long-Term Performance
43:13 Does Staying Private Help Society
49:35 Asking Better Questions with EY
52:12 Are Markets Efficient

CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company.
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SPONSORS:
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
https://www.tabs.com/
https://fleetai.com/
https://www.rogo.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
1:16 Welcome to Run the Numbers
3:17 Meet the Panel: Rebecca, Fred, Rahul
9:52 How Rogo Found PMF
13:47 How Tabs Found PMF
14:51 Growth Rates: Headcount and Revenue
16:23 The Real Hiring Constraint
17:21 What "Forward Deployed" Actually Means
18:53 What's Blocking AI Adoption Now
20:19 How Sales Hiring Has Changed
24:34 How Go-to-Market Has Changed
25:28 Pricing Models: Then vs. Now
28:18 Tabs' Pricing Evolution
29:20 What the Finance Team Looks Like
31:00 How Far You Can Push Outsourced Accounting
32:43 Managing AI Gross Margins
35:07 The North Star Metric for AI Companies
37:02 Token Spend vs. Per-Seat Pricing
39:34 Asking Better Questions: What Counts as ARR
41:38 Biggest Bug in Cash to Collections
43:05 Closing Advice for Founders

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.
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SPONSORS:
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups
—
LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/wisam-hirzalla-9b20a91/
Company: https://stripe.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 What Drives Billing Downstream
1:41 Welcome to Run the Numbers
2:37 Wisam's Path to "Queen of Billing"
4:55 What Head of Billing at Stripe Entails
5:45 Defining Quote-to-Cash
7:50 Layer 1: Pricing and Packaging Mistakes
14:46 Pricing Models Rising Because of AI
18:11 Layer 2: Inside a Quote
19:27 Why Enterprise Deals Get So Messy
24:38 Layer 3: Contracting
27:21 Layer 4: Billing
30:15 Why Usage-Based Billing Is So Complex
34:51 Tokens as a Pricing Unit
36:57 Billing's Move Out of the ERP
39:53 Layer 5: Provisioning and Entitlements
43:36 Layer 6: Tax
44:27 Layer 7: Getting Paid
48:18 Layer 8: RevRec
50:52 When Billing Stopped Being Back Office
51:47 Asking Better Questions Segment
52:28 Will AI Replace Finance Jobs

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.
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SPONSORS:
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/meredithfinn1/
Company: https://front.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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RELATED EPISODES:
Adam Swiecicki - CFO of Rippling
https://youtu.be/JyGJVpmZNac
Aurélien Nolf - CFO of Navan
https://youtu.be/siwzJSRXAvY
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TIMESTAMPS:
0:00 The CFO/COO Dual Mandate
1:45 Welcome to Run the Numbers
2:52 Front's In-House Podcast Studio
3:41 Meredith's Investment Thesis on Front
7:21 The "Portfolio Career" Analogy
8:35 What She Had to Unlearn as an Operator
13:13 Books on Strategy vs. Execution
16:17 When a CFO Should Also Be COO
18:27 What the COO Hat Actually Covers
20:20 Where the Two Roles Conflict
25:42 Budgeting for AI Token Costs
29:16 Using Internal Usage as a Benchmark
35:40 Funding a Series A Bet Inside a Series D Company
38:04 Sizing Bets: Core, Adjacent, Moonshot
40:04 The Secret to Re-Accelerating Growth
41:46 Going Deeper, Not Wider
43:18 What the Pricing Overhaul Taught Her
47:30 Why Customer P&L Matters
50:11 Lightning Round Begins
51:32 Advice to Her Younger Self
52:33 Front's Finance Tool Stack
53:21 Craziest Expense Ever
#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.
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SPONSORS:
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
—
LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/claire-bramley-133b7174/
Company: https://www.xero.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:00 Xero and CJ's History With It
4:12 Xero's Size and Scale Today
5:10 The Expanding CFO Role
7:06 Hiring Experts You're Not
8:47 Imposter Syndrome
11:00 Getting Better at Asking Questions
15:04 Asking the "Stupid Question"
16:21 Finance as the Corporate Junk Drawer
17:48 The Trial Period Idea
18:24 Tripwires: Leading Indicators for CFOs
25:35 AI Hype vs. Main Street Reality
26:44 What Small Business Owners Actually Want
28:45 What Big Corps Underestimate
31:10 Trust as a Competitive Moat
33:45 Why the Line Is Thinner for Small Biz
35:12 AI Inside Claire's Finance Team
37:23 AI for Investor Relations
39:28 Diversity as Capital Allocation
42:07 A Decision Diversity Changed
44:45 Lightning Round Begins
46:06 Advice to Her Younger Self
48:49 Craziest Expense Ever
#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance