Run the Numbers

On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.
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SPONSORS:
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:27 Alex Immerman's favorite CFO interview question
4:54 What a weak answer looks like
5:26 When the hard calls actually matter
6:37 Walt and Roy Disney
7:36 Liked even when making unpopular calls
8:43 Sponsors — Anrok | RightRev | Pulley
11:35 Curt from Clio: ego in the bottom drawer
13:52 CFO as supporting cast
15:10 Backbone vs. ego: when to use each
16:23 Daniel Kang: don't use the purse strings as power
17:36 Earn the seat, don't demand it
18:52 Money is one arrow, not the whole quiver
20:39 Sponsors — Rillet | Maximor | Brex
23:54 Adam Ante: finance people pigeonhole themselves
26:46 The CFO can sit in any meeting
27:30 First 90 days: listen before suggesting
28:46 David Laptor: listen, observe, think, speak
30:50 Build a culture where speaking up is welcomed
31:51 Curt from Clio: don't come in as a know-it-all
33:08 Earn trust through curiosity
33:46 Beware of all-green dashboards
35:28 What would CJ say to Ballmer?
37:14 Parting thoughts from Ben
38:00 Credits

On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.
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SPONSORS:
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/
Company: https://www.datadoghq.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
2:42 FP&A as a product team
4:53 The five pillars of AJ's team
6:39 How far FP&A has come
7:33 How do you know you're doing a good job?
10:20 FP&A as the dashboard, not the engine
10:20 Sponsors — Brex | Anrok | RightRev
13:18 The four-stage FP&A maturity model
16:00 Can you reach all four stages at Series B?
16:45 Why AJ holds weekly forecast meetings
18:24 How often to actually change the forecast
21:42 Sponsors — Pulley | Rillet | Maximor
24:49 Single source of truth: still on the vision board
26:12 AI and the self-serve data risk
26:21 CAC payback over LTV to CAC
29:39 Inside sales vs. enterprise payback comparison
31:47 Finance as the yes, but people
34:02 FP&A vs. IR: which is harder?
36:14 How IR makes you a better FP&A leader
37:19 Is the IR profile shifting?
42:01 IPOs are branding events, not finish lines
43:27 The Datadog IPO during the WeWork meltdown
45:15 Career philosophy: do great work where you are
49:52 Datadog didn't have a role for AJ when he started
52:16 Lightning round
52:24 Screwed up: forgot the currency guy
54:37 Finance software stack
56:16 Advice to younger self
57:13 Credits

On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market.
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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 cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/
Company:https://practicalvc.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:00 Writing as a distribution strategy
5:17 How Dave's blog led to Founders Fund
7:24 Aman: writing at PayPal and law school
9:29 PayPal: the red pen of David Sacks
11:44 Sponsors — Rillet | Maximor | Brex
14:59 500 Startups: the original thesis
16:22 The volume strategy: more shots on goal
18:44 Twilio, Lyft, Sendgrid, Credit Karma
20:15 60x returns: right place, right time
23:07 Sponsors — Anrok | RightRev | Pulley
25:58 Accelerator ecosystem evolution
28:42 500 vs. YC: scale as a weapon
32:52 Globalizing the accelerator model
35:04 Seed to secondaries: how it happened
37:00 Scratching their own itch for liquidity
38:10 The secondary market explained
40:50 Types of secondaries
43:29 Why would a VC sell a winner?
46:07 Managing DPI as a late-stage manager
47:02 The five horse framework
49:15 Skipping the J curve
51:44 Imperfect information as a feature
55:22 Landmines: fraud, mismarked valuations
57:00 VCs lie about valuations three ways
57:58 Forward contracts and counterparty risk
1:00:29 Credits

On this episode of Run the Numbers, CJ breaks down Cumberland Farms’ IPO filing and the surprising business behind it.
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SPONSORS:
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
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
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
2:57 Key metrics
4:28 Europe now out-earns America
5:01 $5.8B debt at 8x leverage
6:20 TLDR: snacks, gas, borrowed money
7:58 Fuel vs. inside: the gross profit photo finish
8:58 COCO, CONCO, and OTHER explained
10:57 Sponsors — Maximor | Brex | Anrok
14:02 Why scale matters: four reasons
16:02 The US convenience store market
17:42 EVs: long the birth rate
18:05 Back to the debt
19:10 The sale leaseback
20:24 Sponsors — RightRev | Pulley | Rillet
23:26 Does the deleveraging math work?
24:27 The growth thesis
25:06 600–700 stores become Cumberland Farms
26:16 The chicken fryer ROI
27:00 Coffee and loyalty: 6M members in 13 months
28:15 Red flag 1: five-for-five COSO failures
28:41 Red flag 2: entire C-suite is new
29:04 Red flag 3: lending to their own parent
29:42 Red flag 4: Big Tobacco funds loyalty
29:57 Red flag 5: foreign issuer, Cayman charter
30:10 Red flag 6: one supplier is 31% of costs
30:32 Red flag 7: balance sheet is stale
30:45 Cap table: TDR Capital and the Issa brothers
31:55 Casey's vs. ARCO
33:47 Goldman got bumped
34:08 Massachusetts banned the pump clip until 2015
34:57 No health insurance disclosure for 16K US workers
35:30 Robert Swan (ex-Intel CEO) is on the board
36:08 Credits

In this episode of Run the Numbers, CJ sits down with Rogo president Rahul Rekhi to unpack what AI actually changes in investment banking and finance. They dig into token economics, why adoption without ROI is a trap, how vertical AI wins, and why domain expertise still matter.
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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 cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/rahulrekhi/
Company: https://www.rogo.ai/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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RELATED EPISODES:
A CFO Explains the Stock Exchanges
https://youtu.be/pooOE6ZNGR4
A CFO Explains Marketplaces
https://youtu.be/LpbH9GpBrSY
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TIMESTAMPS:
0:00 Preview and Intro
2:44 Why finance was first to verticalize AI
6:28 What the president title means at Rogo
9:55 Sponsors — Pulley | Rillet | Maximor
13:02 The problem Rogo is solving
16:16 Token maxing is not transformation
17:43 Why ROI is so hard to measure
19:39 Sponsors — Brex | Anrok | RightRev
22:37 ROI is business-unit specific
24:03 Budgeting tokens like a benefits load
25:00 AI incentives aren't aligned to efficiency
26:26 The model broker function
32:03 Not all token spend is equal
37:14 Who owns AI efficiency?
40:59 The forward deployed banker
43:00 Domain expertise: the Interstellar analogy
49:21 Lightning round
49:28 Screwed up: DCF error in a live deal
51:13 Will new grads have the spidey sense?
53:03 Meeting Pope Francis
55:04 Fact-checking jobs numbers at the White House
57:39 Advice to younger self
59:21 Credits