Run the Numbers

Do PE Companies Trade Innovation for Margins?

Private equity firms love to talk about operational excellence… but when “efficiency” comes at the cost of innovation, are they mortgaging tomorrow for today’s margins?

In this episode I break down why 25% operating margins became the magic number in software, how PE-backed businesses chase the Rule of 50, and what happens when cutting R&D tips companies into the “Innovation Death Spiral.”

Today’s podcast is brought to you by Campfire.

You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.

If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.

You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.

Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai.

How do finance leaders enable growth while fostering a culture of partnership, positivity, and saying yes? In this episode, CJ interviews Ed Park, Head of FP&A at Facebook during its explosive hypergrowth years, Head of Finance and Internal Operations at Asana, the current CFO of Daffy, and a “glass-half-full” finance leader. Ed shares stories about working at Facebook in the early days, how he brought finance into the company’s engineering and product-first culture, and how he built trust while navigating rapid user and infrastructure expansion. He talks about his role at Asana, why the company plans in episodes, not quarters, how they discovered their unique “three user” metric, and how they transitioned from bottoms-up to sales-led growth. Ed also gives an introduction to donor-advised funds and how Daffy, his current company, is disrupting this field. The conversation covers how a company's business model shapes its destiny, finding the balance between what’s urgent and what’s important, and Ed’s glass-half-full approach to being a finance leader who enables teams by saying yes.

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LINKS:

Edward Park on LinkedIn: https://www.linkedin.com/in/edwardypark

Daffy:

https://www.daffy.org

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

RELATED EPISODES:

Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor —

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:16) Sponsor – Aleph | RightRev | Navan

(06:43) Ed’s First Job at a Startup: Head of FP&a at Facebook

(11:35) Bringing Finance Into an Engineering and Product-Led Culture

(16:42) Sponsor – Rillet | Pulley | Brex

(20:34) Balancing What Was Urgent Versus Important

(25:02) Monetizing Facebook

(26:48) Becoming a Glass-Half-Full Finance Leader

(33:27) Managing Four Chefs at Asana

(35:38) How Asana Plans in Episodes, Not Quarters

(42:48) Monetization Model Intuition and the “Three User” Metric

(48:13) Transitioning From Bottoms-Up to Proactive Sales at Asana

(53:24) Daffy’s Monetization Model and Donor-Advised Fund Innovation

(57:34) How a Business Model Shapes Destiny

(1:00:02) Ed’s “How Might We” Approach to Being a CFO

(1:01:56) Long-Ass Lightning Round: A Big Mistake

(1:04:38) Advice to Younger Self

(1:05:44) Finance Software Stack

(1:07:57) Craziest Expense Story

—

SPONSORS:

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

#FacebookBusinessModel #FPandA #StartupFinance #MonetizationStrategy #DonorAdvisedFunds

Premji Invest is an investment firm that backs some of the biggest names in the CFO and enterprise tech stack, including Anaplan, Zuora, Coupa, and Looker. In this episode, CJ is joined by Sandesh Patnam, the firm’s Managing Partner, to discuss their approach to investing and the future of CFO tech. Sandesh talks about the evergreen nature of Premji’s investment model and explains how this permanent pool of capital enables the company to focus on deep partnerships and durable growth, rather than chasing fund cycles or portfolio diversification. He breaks down why he views total addressable market (TAM) as a floor rather than a ceiling, how investing across both public and private markets creates a strategic advantage, and how startups should approach capital construction and optionality in today’s market. The conversation also touches on the evolution of the CFO toolkit, how AI is shifting the finance role, what persistent finance problems are still waiting for innovation, how org design is changing inside finance teams, and why he believes AI is a bigger shift than both the dot-com and mobile eras.

—

LINKS:

Sandesh Patnam on LinkedIn: https://www.linkedin.com/in/sandeshpatnam

Premji Invest:

https://in.premjiinvest.com

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

RELATED EPISODES:

BlackRock Managing Director on the Secrets of Durable Companies -

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:08) Sponsor – RightRev | Navan | Rillet

(06:59) Evergreen Capital and Premji’s Approach to Investing

(09:25) Portfolio Construction

(12:58) TAM Versus SAM Versus Product

(15:28) Sponsor – Pulley | Brex | Aleph

(19:51) Seats Versus Outcome-Based Pricing

(23:30) Defining Durability

(26:31) Public Versus Private Investing

(28:44) Why One Team Manages Both Public and Private Investing

(30:47) Capital Construction for CFOs With Evergreen Investors

(32:13) How and When Evergreen Funds Seek Liquidity

(35:32) Building Optionality in Capital Strategy Amid Market Changes

(38:01) Secondary Markets in the Private World

(41:39) The Evolution of the CFO Tech Stack

(43:41) AI and Systems of Action

(45:43) How CFOs Are Starting To Interact With AI Tech

(49:09) A Finance Problem That’s Open for Innovation

(50:25) The Evolution of the CFO’s Role Beyond Finance

(51:33) The AI Era vs. Prior Tech Eras

—

SPONSORS:

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

#EvergreenCapital #PremjiInvest #CFOTechStack #InvestmentStrategy #PortfolioDurability

Cybersecurity company Netskope has filed to go public on the NASDAQ.

Today we’re breaking down their S1 filing, including their financials, valuation outcomes, and potential red flags.

Today’s podcast is brought to you by Campfire.

You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.

If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.

You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.

Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai.

The media landscape is noisier than ever. How can founders and business leaders get their stories heard? And in an age of AI-driven content, how can creators distinguish themselves and build a direct relationship with their audience? In this episode, CJ sits down with Alex Konrad, a longtime tech journalist, former Forbes editor (responsible for curating the renowned Forbes 30 Under 30, Cloud 100, and Midas lists), and founder of Upstarts, a newsletter covering startups, venture capital, and the people shaping the innovation economy. Alex shares insider stories from his decade at Forbes, including how lists like the “30 Under 30” were created and what it was like profiling (and sometimes singing karaoke with) the likes of Marc Benioff, Satya Nadella, and Sam Altman. The conversation explores the evolving landscape of media, the business fund-raising announcements, how startups can actually work with journalists to shape perception, the rise of VC firms as media powerhouses, the shifting role of platforms like Substack and LinkedIn, why relationship-driven content will outlast the race to break news, and the death of traditional SEO.

—

LINKS:

Alex Konrad on LinkedIn: https://www.linkedin.com/in/alexrkonrad

Alex Konrad on X (@alexrkonrad): https://x.com/alexrkonrad

Upstarts Media:

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

LINKS MENTIONED:

No Priors: AI, Machine Learning, Tech, & Startups: https://www.youtube.com/@NoPriorsPodcast

Latent Space: https://www.youtube.com/@LatentSpacePod

The Daily: https://www.nytimes.com/column/the-daily

52 Sourcery with Molly O'Shea https://www.youtube.com/@SourceryVC

The Information: https://www.nytimes.com/column/the-daily

RELATED EPISODES:

“Let’s Just See What Breaks” — Intuit’s CFO on Being a Disruptor When You’re Already the Incumbent -

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:32) Sponsor – Navan | Rillet | Pulley

(07:13) Building the Forbes 30 Under 30, Cloud 100, and Midas List

(11:49) The Meme of SEC Trouble on Forbes List and a Media Tip

(14:08) Why Lists Work So Well

(17:17) Sponsor – Brex | Aleph | RightRev

(21:57) What Might Convince Alex To Start a List

(23:13) Karaoke With Benioff & Interacting With Billionaires

(29:14) Entrepreneurship & Work-Life Integration

(33:25) Sales Skills Alex Learned as a Founder

(37:56) The Dance Behind Fundraising Announcements

(42:30) How To Capitalize on the Media Outside of Funding Rounds

(45:24) Examples of Founder “Oh S**t!” Moments

(47:58) VC Firms As Media Companies

(51:16) Non-Journalists Interviewing in Tech

(55:02) Audience Relationship & Guarding Against AI

(57:41) The Death of SEO

(1:00:45) The Value of Time Sensitivity and News in the Era of AI

(1:02:40) Platform Relationships & Substack

(1:04:55) Bootstrapping Media & VC Pressure

(1:10:55) Wrap

—

SPONSORS:

Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

#TechJournalism #MediaStrategy #AIinMedia #StartupPR #FutureOfMedia

Cybersecurity risks have become more complex and unpredictable than ever, yet many companies struggle to quantify these threats in terms that truly matter. How can CFOs and CISOs effectively communicate about risk, make smart security investments, and navigate the emerging challenges posed by AI? In this episode, CJ interviews Andy Ellis, a renowned cybersecurity leader, former CISO of Akamai, investor, director, advisor, leadership coach, and author of the book 1% Leadership. Andy unpacks why most companies measure risk the wrong way and breaks down his "Pyramid of Pain” framework for categorizing it. He discusses the dynamics between CFOs and CISOs in purchasing security tools, demystifies security budgeting and vendor negotiations, dives into the evolving role of AI in security operations, and explains why the CISO and CIO roles are on a collision course. Andy also reveals insider stories from the frontlines of major breaches, shares a compelling risk analogy inspired by vampires and zombies, and clears up once and for all why the demise of the Death Star was not a failure of risk management.

—

LINKS:

Andy Ellis on LinkedIn: https://www.linkedin.com/in/csoandy

Andy Ellis on X: (@CSOAndy) https://x.com/csoandy

Website:

https://www.csoandy.com

1% Leadership: https://www.amazon.com/1-Leadership-Master-Improvements-Leaders/dp/0306830817

How to CISO:

https://www.howtociso.com

Duha One:

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:49) Sponsor – Rillet | Pulley | Brex

(07:23) Defining Risk: Technical & Human-Friendly Perspectives

(09:20) Actuarial Risk Versus Human-Driven Risk

(15:33) Why the Demise of the Death Star Wasn’t a Failure of Risk Management

(16:58) Sponsor – Aleph | RightRev | Navan

(21:22) How the Death Star Metaphor Relates to Real-World Security Breaches

(23:20) Why Risk Should Not Be Quantified in Dollar Terms

(25:15) The Pyramid of Pain: Risk Severity and Surprise Levels

(30:21) How CFOs and CISOs Should Partner on Security Purchases

(34:03) Are Security Budgets Over or Under-Spent?

(36:22) Balancing Budget for Security Tools and People

(39:48) Tips for FP&As on Brokering the Security Budget With Your CISO

(44:10) Factoring AI Uncertainty in a Three-Year Security Roadmap

(46:38) AI Washing in Security Products and Realistic Impact

(48:55) The Limitations of Security Operations

(50:53) The Future of CIO and CISO Roles and Organizational Reporting

(54:55) Why IT Shouldn’t Report to the CFO

(57:18) Israeli Unit 8200 and Cybersecurity Innovation

(59:50) Startups Versus Public Companies: Differing Risk Models

(1:02:52) Wrap

—

SPONSORS:

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.

#Cybersecurity #RiskManagement #CISO #SecurityOperations #SecurityFinance

On average, I get asked 2x a week for fractional CFO recommendations.

And on average, I get complaints 3x a week about someone’s current setup.

Today we investigate the booming fractional CFO market, and my checklist to making sure you get a good one.

This week’s podcast is brought to you by Campfire (www.campfire.ai)

We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.

Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.

I’m excited to see how they keep reimagining this space – and you should be too.

Check them out at www.campfire.ai

In 1997, the Florida Marlins won the World Series, but they also lost $30 million in the process. In 2002, only three Major League Baseball teams had positive EBITDA. Due to a dramatic collective bargaining agreement, five years later, only three clubs had negative EBITDA, and the MLB had gone from $500 million in losses to a $500 million in profit. Today’s guest had a front row seat to the action. Jonathan Mariner is the former CFO of the Florida Marlins, the Florida Panthers, and Major League Baseball. He is also he founder of TaxDay and a seasoned board member on different boards, including Tyson Foods, OneStream, and Delaware North, among others. In this episode, he takes us inside the complex economics of pro sports. The conversation covers the surprising way sports franchises are actually valued, the massive shift from cable TV to streaming, the complex world of player merchandising, the challenges of expanding sports internationally, and how Jonathan helped implement a controversial EBITDA rule to rein in league-wide debt.

—

LINKS:

Jonathan Mariner on TaxDay: https://www.taxday.com/team/

Tax Day:

https://www.taxday.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

RELATED EPISODES:

The Boston Celtics’ Other Playbook: Business Insights from President Rich Gotham —

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:35) Sponsor – Pulley | Brex | Aleph

(07:11) How Jonathan Became CFO of the Florida Marlins and Panthers

(13:17) The Marlins: Winning the World Series and Losing $30 Million

(16:03) Sponsor – RightRev | Navan | Rillet

(20:08) How Not Having a Salary Cap Affects the MLB

(21:27) The Collective Bargaining Agreement That Changed the Economics of the MLB

(30:00) The Science of How Sports Franchises Are Valued: Revenue

(31:53) The Art of How Sports Franchises Are Valued: Perception

(36:20) How Local Broadcast Rights and Revenue Sharing Work

(37:44) Contractually Obligated Income and Its Ramifications

(41:57) How Player Jersey Sales Really Work

(46:34) The Shift From Cable to Streaming and the Economic Effects

(53:48) The Challenges and Opportunities of Global Expansion

(59:57) Expansion Teams & Franchise Fees

(1:01:58) Being on the Tyson Foods Board During COVID

(1:05:39) Jonathan’s Other High-Stakes Moments as a Board Member

(1:08:03) Founding TaxDay

(1:11:41) Long-Ass Lightning Round: Career Mistakes

(1:14:00) Advice to Younger Self

(1:15:11) The Best Sporting Events Jonathan’s Ever Attended

—

SPONSORS:

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

#SportsFinance #MLB #MajorLeagueBaseball #TeamValuation #BusinessOfSports

If you’re curious about what it’s really like to navigate a multibillion-dollar acquisition deal during a global pandemic, while under intense scrutiny of the Department of Justice, this episode is for you. Jason Pate, Chief Strategy Officer at Plaid, takes us behind the scenes of Visa’s $5 billion bid to acquire Plaid and why it ultimately didn’t happen. Jason also explains the massive evolution of Plaid from a linking infrastructure company to a thriving network business powering some of the biggest names in fintech. The conversation delves into the company’s pivotal moments, including its recent $575 million fundraising round to solve for employee RSU liquidity. Beyond that, Jason shares lessons from his experience, unpacking the importance of understanding a customer's P&L, breaking down how to build durable fintech revenue streams through diversification, and offering candid insights on negotiation, the future of payments, and making big bets to fix something that isn't broken.

—

LINKS:

Jason Pate on LinkedIn: https://www.linkedin.com/in/jason-pate-50735310/

Plaid:

https://plaid.com

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

—

TIMESTAMPS:

(00:00) Preview and Intro

(01:43) Sponsor – Brex | Aleph | RightRev

(06:08) Duke and “I Hate Christian Laettner”

(07:45) Jason’s Product Development Experience and Career Journey

(10:38) The Importance of Understanding Your Customer’s P&L

(12:41) Plaid’s Transition From Linking Infrastructure to Network Business

(15:23) Sponsor – Navan | Rillet | Pulley

(18:55) Building the Plaid Data Network and Ecosystem

(25:41) Friction in Payments: Feature Versus Bug

(27:46) The Future of Payments: Check-In Versus Checkout

(31:21) Negotiations: Less Like Chess, More Like Marco Polo

(35:21) Identifying Gives That Aren’t Actually Gives

(37:10) Plaid’s Unsuccessful Acquisition by Visa

(40:45) Being Interviewed by the DOJ During the Pandemic

(43:49) Plaid’s Recent Raise and the Unconventional Reason for It

(47:00) Valuations: Fundraises Versus Sales

(48:19) Building an Equity Program When Companies Stay Private Longer

(50:48) Multi-Product Diversification: The Key to Durable FinTech Revenue

(53:07) When & How To Transition From an Infrastructure to a Network Business

(59:03) Jason’s Philosophy on Ramping Team Members

(1:01:04) Lessons From Roger Federer

(1:02:52) Long-Ass Lightning Round: A Career Mistake

(1:04:03) Advice to Younger Self

(1:04:48) A Helpful Tactic for Negotiations

—

SPONSORS:

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.

Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.

#Plaid #Fintech #acquisition #fundraise #employeeRSU #BusinessTransition

What matters more: Your company performance, or market conditions?

Stubhub is preparing to go public (again) after initially pulling the plug back in March of 2025. A lot has changed since then. The market is up. And their performance is down. We analyze what’s going on in the capital markets, and how to think about what matters most when you’re preparing to go public.

(Read: Stubhub’s original S1 breakdown on Mostlymetrics.com)

This week’s podcast is brought to you by Campfire (www.campfire.ai)

We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.

Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.

I’m excited to see how they keep reimagining this space – and you should be too.

Check them out at www.campfire.ai