Run the Numbers

In this episode of Run the Numbers, CJ Gustafson breaks down the diamond industry as a business model: how De Beers controlled supply, engineered demand, and built one of the most powerful pricing machines in history. From the Central Selling Organization to “A Diamond Is Forever” to the rise of lab-grown diamonds, this episode unpacks monopolies, scarcity, pricing power, and what happens when technology forces transparency.

—

SPONSORS:

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

Rillet is an AI-native ERP built for modern finance teams that want to 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

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

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

—

LINKS: 

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

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

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

—

RELATED EPISODES:

Why Uber Drivers Can’t Escape the 30% Cut

https://youtu.be/LpbH9GpBrSY

—

TIMESTAMPS:

All verified. Here are the timestamps:

0:00 Blood Diamond

1:55 Show intro

2:15 Diamond history: ancient India and riverbed origins

3:56 Brazil supply shock and the mining era

4:39 De Beers: Cecil Rhodes and the PE rollup

6:47 Sponsors — RightRev | Rillet | EY

9:49 The Central Selling Organization (CSO)

10:39 The site system: invite-only, take-it-or-leave-it auctions

12:22 Diamonds are more abundant than gold

13:01 NW Ayer, Bernays, and engineering demand

14:17 "A Diamond is Forever" campaign

15:13 Lab grown diamonds: 20% of US purchases

16:32 De Beers collapses: $3.1B operating loss

17:18 Sponsors — SpendHound | Brex | Aleph

21:07 Lesson 1: Rollups are powered by capital

21:39 Lesson 2: Distribution beats mining

22:11 Lesson 3: Artificial scarcity unravels

22:55 Lesson 4: Price opacity is a temporary moat

23:39 Lesson 5: Demand engineering

24:30 Lesson 6: The real product was risk smoothing

26:30 Credits

#RunTheNumbersPodcast #BusinessStrategy #FinanceHistory #Pricing #Monopoly

In this episode of Run the Numbers, CJ Gustafson sits down with Angela Chen, former CFO of The North Face and Mars Veterinary Health, to unpack how finance leaders build and scale iconic consumer brands. Angela shares how to measure brand equity, why the CFO should act as an architect of growth, and how capital, talent, and strategy connect inside a scaling business. They also get into humanistic leadership, consumer-margin tradeoffs, and what a 39-cent Taco Bell taco can teach finance teams about growth.

—

SPONSORS:

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS: 

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

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

Company: https://sku.is/

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

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

—

RELATED EPISODES:

Minted’s CFO: Half the Year Happens in One Month

https://youtu.be/hD4-exunKMo

—

TIMESTAMPS:

0:00 Preview and intro

2:45 Measuring brand equity

5:09 CFO as architect of growth

7:11 Connecting money, ideas, and talent

7:52 North Face vs. Mars: where to invest

10:52 Sponsors — Aleph | RightRev | Rillet

14:14 Scaling North Face 5x without diluting the brand

16:31 From technical brand to lifestyle brand

19:30 Quality of revenue

21:49 Seasonality and Q4 concentration

24:01 Sponsors — EY | SpendHound | Brex

27:14 Retailers shouldn't own factories

31:30 Supply chain and 18-month product cycles

33:23 Humanistic leadership in finance

34:32 Purpose and profit are mutually reinforcing

36:15 Purpose vs. profit in public companies

38:05 Playing to Win framework

39:47 Operational cadence and the gas gauge

43:02 Killing bad projects: the battery jacket story

44:16 Taco Bell and 39-cent margins

47:10 Lightning round

47:36 Screwed up: hiring on credentials

48:27 Advice to younger self: network is the work

50:07 Craziest expense story: snowcat ski trip

50:50 Credits

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

—

LINKS: 

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

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

Company: https://psgequity.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

2:44 PSG origin story

4:01 Growth to 30B AUM

5:07 Strategy: small software at scale

5:50 Vertical SaaS treasure hunting

8:10 Ministry Brands: software meets payments

9:28 Sponsors — Brex | Aleph | RightRev

12:46 Early M&A work and rollup strategy

15:52 Sourcing is more competitive now

18:28 Smoke signals and relationship sourcing

21:22 Does brand get you in the room?

22:15 Authenticity as a sourcing edge

22:52 Sponsors — Rillet | EY | SpendHound

26:09 Brand name of investor or deal partner?

27:44 Investors are narrative driven animals

29:18 Market, product, then execution

31:26 Danger of falling in love with the narrative

33:40 Operator AI pivot story: GRC company

34:51 Keep it simple: one tab, five key inputs

39:21 Forecasting confidence beyond 12-18 months

41:51 What makes a useful board meeting

45:01 Build vs. buy: the payments decision

47:45 ARR vs. EBITDA multiples

50:30 Lightning round

50:34 Board materials: send 3 days in advance

51:03 LTV to CAC and cap software debates

51:32 First deal at PSG

52:35 What young investors get wrong

54:04 Credits

In this episode of Run the Numbers, CJ sits down with Manu Diwakar, CFO of Virta Health, to unpack why health tech breaks traditional SaaS thinking. They get into the realities of running a business where outcomes matter, half the company are medical professionals, and efficiency can’t come at the expense of care. It’s a conversation about sustainable scaling, smarter reinvestment, and building for durability over hype.

—

SPONSORS:

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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

—

LINKS: 

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

Guest: https://www.linkedin.com/in/manu-diwakar-1aa578/

Company: https://www.virtahealth.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:18 Welcome and guest intro

3:02 What sector is health tech?

4:34 Virta go to market explained

7:01 B2B to B2C model

9:00 Value based care and ROI guarantees

9:18 Half the company are medical professionals

10:36 Sponsors — SpendHound | Brex | Aleph

14:03 Annual planning process

16:42 Shape of the curve

17:33 TAM: metabolic health is massive

20:45 Fee for service vs. value based care

24:16 Sponsors — RightRev | Rillet | EY

27:24 Unique costs of health tech: billing, compliance

30:54 Corporate practice of medicine

31:44 North star: members under management

32:43 The flywheel: $250 charge, $500 saved

33:28 Early stage CFO job is easy

35:28 Bad habits baked in during high growth

38:02 Choosing not to profit vs. not turning a profit

41:15 Running a VC-backed business for sustainability

42:07 People, tech and process framework

44:31 Hiring philosophy: hard work, learning, curiosity

48:26 Athletes vs. experts in hiring

50:03 Clock hands interview question

50:49 Lightning round

51:09 Screwed up: having hard conversations late

51:57 Advice to younger self

52:15 Finance software stack

52:42 Craziest expense story

53:47 Credits

In this episode of Run the Numbers, CJ sits down with Praveer Melwani, CFO of Figma, to unpack the financial model behind one of tech’s most iconic product-led companies. They cover viral growth, forecasting without a traditional sales pipeline, AI credit pricing, margin tradeoffs, and the metric Praveer believes matters most in the long run: free cash flow per share.

—

SPONSORS:

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

—

LINKS: 

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

Guest: https://www.linkedin.com/in/praveer-melwani/

Company: https://www.figma.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:21 Welcome and guest intro

2:55 From banking to Dropbox to Figma

5:04 Inflection points: building trust early

8:36 TAM expansion thinking

10:31 Sponsors — EY | SpendHound | Brex

13:38 Two-thirds of Figma users aren't designers

14:36 Forecasting product led growth

16:22 Cohorts and NDR discovery

17:39 LTV to CAC philosophy

18:57 Product signals for account expansion

20:22 How Figma achieved hypergrowth with 90%+ margins

22:14 AI expands TAM: time to hit the gas

23:22 AI credit pricing model

24:50 Sponsors — Aleph | RightRev | Rillet

28:13 Outcome based pricing consideration

29:00 Where AI margins settle: gross profit dollars

30:08 Free cash flow per share as north star

31:04 NDR and pricing volatility

32:13 Bundled vs. unbundled seats

34:50 Being engaged in sales to understand admin pain

35:17 IPO day experience

36:27 Keeping employees focused beyond the stock price

37:19 Employee stock pressure and lockup reality

39:37 Kitchen cabinet of advisors

41:44 How to ask better questions of advisors

41:47 Lightning round

41:50 Advice to younger self

42:47 Finance software stack

44:09 Claude WTF moment: forecasting model throughput

45:13 Craziest expense story: the haircut

45:59 Credits

In this episode of Run the Numbers, CJ sits down with Wealthfront CFO Alan Imberman to unpack automation as a strategy, the compounding power of retention and trust, and how to balance elite profitability with continued investment. They also discuss why Wealthfront went public earlier than many peers and what’s really happening in fintech right now.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

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

—

LINKS: 

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

Guest: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/

Company: https://www.wealthfront.com/

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:37 Welcome and guest intro

3:11 Wealthfront overview

4:38 Automation as core philosophy

6:50 55K clients per support rep example

7:45 90% gross margins and $1M revenue per employee

8:46 Optimization vs. exploration framework

9:58 Data flywheel: the Path product

10:43 Cash account insight from customer data

11:26 Home lending insight from wire data

13:33 Sponsors — Rillet | EY | SpendHound

16:45 Product led growth and referrals

18:11 Incentives vs. paid marketing

20:46 Compounding philosophy and 120% NDR

22:07 Long term thinking vs. public market pressure

22:40 No guidance decision

26:26 Sponsors — Brex | Aleph | RightRev

29:44 Serving the wealth builder: 80/20 in wealth management

31:45 Decision to go public at $339M revenue

33:46 Does size matter for IPOs?

34:46 Fintech's moment: Chime, Klarna, Circle

36:49 Non-monetary benefits of going public

38:30 Memos over slides

40:31 Hedge fund early career: spreading 10-Ks in Excel

46:45 Don't lose the forest for the trees in modeling

48:31 Lightning round

48:43 Screwed up: de-annualizing a fee rate

49:55 Advice to younger self

50:32 Finance software stack

51:14 Craziest expense story: $100K coffee tab

53:11 Credits

#RunTheNumbersPodcast #CFO

On this week’s Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. 

—

SPONSORS:

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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

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

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

—

LINKS: 

Steve on LinkedIn: linkedin.com/in/steveisomjr

Company: https://bloomerang.com/

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

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

—

TIMESTAMPS:

0:00 Preview

1:25 Intro

2:55 Welcome Steve Isom

3:13 CFO to COO promotion

5:02 Having a pulse on every function

6:51 Defining "strategic CFO"

7:19 Tying strategy to value creation

9:27 Being embedded in the rhythm of the business

10:55 Finance leaders as commentators vs. team captains

12:25 Sponsors — RightRev | Rillet | EY

15:33 Killing projects as a core skill

18:14 Activity doesn't equal impact

19:16 Project Steve killed

20:39 Taking over the customer org at Bloomerang

22:18 Why acquisition is a cash-losing exercise

23:07 LTV lives post-sale

24:39 Most vulnerable area: customer success

25:24 Ruthless CSM segmentation

26:30 Nonprofits don't think about your software

29:21 Sponsors — Spendhound | Brex | Aleph

32:43 CFO running ops

35:52 Metrics vs. humans

37:18 Skip levels and what they reveal

39:01 Incentives drive the wrong outcomes

40:22 Customer-introduced delays as a key sub-metric

40:27 Unit economics become tangible when you're accountable

42:17 Going deep on AI

45:13 Motivating your team to experiment with AI

46:02 AI for personal projects

47:05 Resource allocation in a vibe-coding world

48:42 Does AI efficiency just mean more work?

50:32 What excites Steve about the future of finance leadership

52:08 Finance leaders who don't use AI won't get hired

52:13 Credits

#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO

Secondaries aren’t a niche anymore — they’re the main event. In 2025, the secondary market hit $233B, outpacing IPOs 5:1. This episode breaks down how we got here, why companies stay private longer, and how employees, investors, and CFOs actually navigate liquidity. From Facebook’s wild west to structured tenders and continuation vehicles — this is the new playbook.

—

SPONSORS:

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS: 

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

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

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

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

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

—

RELATED EPISODES:

IPOs Are Being Replaced

https://youtu.be/oGuZf83pdRE

The $10T Question: Who Needs Wall Street?" | Scott Voss

https://youtu.be/szCIZmTs3SQ

Driving revenue without selling | Greg Henry of 1Password

https://youtu.be/f5FsNoG8A3E

Finance vs. Marketing: Who’s Really Right About ROI? | Brandon Sullivan

https://youtu.be/ivcht5N7uRQ

Do the things spreadsheets can’t do | SeatGeek’s Teddy Collins

https://youtu.be/jn0L5KkmMI4

—

TIMESTAMPS:

0:00 The $233B market replacing IPOs

2:57 What is a secondary?

4:24 The dot-com hangover

5:48 The wild west era

8:58 Sponsors — Aleph | RightRev | Rillet

12:21 Why companies stay private longer

13:56 The three stakeholders

18:57 When is it too early?

20:42 How to run one of these things

23:57 Sponsors — EY | SpendHound | Brex

27:04 Not all shares are created equal

31:08 The good, the bad, and the ugly

34:23 GP-led continuation vehicles

36:19 The whole game changed

37:34 Credits

#RunTheNumbersPodcast #PrivateMarkets #SecondaryMarkets #VentureCapital #CFO

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

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

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

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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

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

—

LINKS: 

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

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

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

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

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

—

TIMESTAMPS:

0:00 Preview and intro

1:13 Welcome and guest intro

2:38 Football at Duke and college businesses

5:40 Predecessor to DoorDash story

7:10 IP monetization explained

9:22 All deals are snowflakes

10:36 Partnership KPIs

13:21 Sponsors — Brex | Aleph | RightRev

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

17:15 Single view of the fan

18:39 Multi-business customers spend 4.7x

20:32 Fanatics credit card launch

22:13 AI for personalization

23:01 DTC vs. wholesale margin profiles

24:05 Budgeting process

26:07 Infinite vs. finite: focus on revenue

26:37 Sponsors — Rillet | EY | SpendHound

29:47 Starve your losers, feed your winners

32:58 Capital compounding: revenue, EBITDA, FCF

33:56 Buybacks at IAC

37:02 First negotiation at Lehman

39:17 Outlasting the other side

39:56 Listening in negotiations

40:03 Long-Ass Lightning Round

44:25 Credits

#RunTheNumbersPodcast #CFO #SportsCommerce #CapitalAllocation #FinanceLeadership

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

—

SPONSORS:

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

—

LINKS: 

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

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

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

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

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

—

TIMESTAMPS:

0:00 Preview and Intro

2:14 PE to venture incubator

4:39 Operational empathy from zero-to-one

4:45 First paying user feeling

5:40 Jet ski customer support story

8:49 Hanging with IC sales reps

12:24 Sponsors — Tabs | Abacum | Brex

15:44 Finance as the decision engine

17:36 Gorgias overview

20:20 Pricing structure and iteration

22:11 Outcome based / resolution pricing

24:48 AI success rate as key metric

25:33 Sponsors — Metronome | RightRev | Rillet

28:57 Pricing value split — $1 per resolution

31:17 Vertical specificity as AI moat

33:27 Managing LLM costs

35:41 Falling token costs and model mix

39:28 Order to cash as growth engine

43:31 Auditing order to cash at 25M ARR

44:09 Manual choke points

46:32 Learning density over titles

48:30 SurveyMonkey as the most formative period

50:07 Lightning round

50:17 Listening to respond vs. listening to learn

51:04 Advice to younger self

52:02 Finance software stack

52:45 Cortex — internal AI decision tool

54:21 Craziest expense story

54:52 Credits