Run the Numbers

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.
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SPONSORS:
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/richardharem/
Company: https://rapidsos.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:10 What RapidSOS does
4:59 CJ’s own car accident
5:33 What's broken about 911
6:50 Who's the actual customer
7:46 How RapidSOS monetizes
10:13 Sponsors — Pulley | Rillet | Maximor
13:27 Too much data, too much noise
16:35 Data pollution and trust
18:24 The data stack early on
19:25 Should BI have come sooner?
20:45 The framework: questions to decisions
22:43 Building a data culture
23:58 Sponsors — Brex | Anrok | RightRev
26:51 Bottoms-up vs. top-down AI
28:42 Inspiration, not training
32:24 The three-phase AI progression
33:31 Founding an AV company at 8
35:37 Giving people room to grow
38:12 Depending on heroes
39:55 Working under founder personalities
41:23 Do startups undervalue what they sell
42:48 A price hike, zero churn
43:24 Signs you're underpricing
44:57 Lightning round
45:03 Screwed up: refreshed data before a demo
47:15 Advice to younger self
47:41 Finance software stack
48:37 Craziest expense: personal gas
49:29 Credits

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company.
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SPONSORS:
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/seun-sodipo-1498b580/
Company: https://plaid.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
2:12 What Plaid does
3:53 How Plaid makes money
7:04 Eight months in, not new anymore
8:57 Sponsors — RightRev | Pulley | Rillet
11:48 Career path: Stripe, Glossier, Plaid
14:32 Evaluating durability from the outside
15:36 Rising expectations and AI
17:23 Top-down vs. bottoms-up AI adoption
20:06 Sponsors — Maximor | Brex | Anrok
23:20 Coolest AI use case: sorting physical mail
25:21 How her questions have changed
27:11 AI should make you think deeper
27:51 Finance AI Day explained
31:23 A four-month journey to usable tools
32:22 How AI changed her leadership style
33:19 Skills that matter more now
36:22 The Objective, Strategy, Tactics framework
39:56 What planning reveals about an org
41:36 Sequential vs. parallel planning
45:38 Measuring the value of a network
47:33 What people underestimate about Plaid
48:56 Lightning round
48:56 Screwed up: the reversed page order
49:39 Advice to younger self
50:32 Finance software stack
51:43 Craziest expense: the photo shoots
52:20 Credits

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

On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.
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SPONSORS:
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/
Company: https://www.datadoghq.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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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