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 m...
Aug 25, 2025•1 hr 6 min
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 tha...
Aug 23, 2025•9 min
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 ...
Aug 21, 2025•1 hr 21 min
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 b...
Aug 18, 2025•1 hr 6 min
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.a...
Aug 16, 2025•7 min
If you’re thinking about adding payments to your software company’s tech stack, listen to this first. Today’s guest knows that turning payments into a prolific growth engine isn’t as simple as plugging in a processor; it’s about knowing when you have the “right to win” and building the infrastructure, team, and go-to-market strategy to make it work. In this episode, Andrew Mosawi of JMI Equity and a self-named “dinosaur in the world of embedded payments”, joins CJ to unpack how embedded payments...
Aug 14, 2025•55 min
With a decade of experience at Yext, a company now approaching half a billion in ARR, Darryl Bond has seen it through negative EBITDA margins, executive turnover, and company-wide resets. In this episode, he sits down with CJ to talk about his approach to the finance function, which involves prioritizing growth over compensation, tackling the messy problems head-on, making the hard P&L calls in the “grey zones,” knowing when to ask for help, and staying focused through the tough times. Darry...
Aug 11, 2025•59 min
What do Whitey Bulger, FBI Agent John Connolly, AI and Venture Capitalists have in common? In today’s episode we explore an unholy alliance between two forces that need each other—massive capital piles and foundational model companies that can actually absorb that capital. 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 spreadsheet...
Aug 09, 2025•8 min
Are you building a sales org from scratch? Or rebuilding one in the middle of an AI boom? If so, this episode is your field guide. CJ sits down with Ethan Schechter, SVP of Global Sales and Customer Success at Qodo (and the guy who helped take Snyk from $0 to $100M+ in revenue), to talk about the wild days of early-stage sales leadership. Ethan shares how he navigates “basecamp” moments and the “smile” and “cry” days of year one. He explains his approach to hiring for a new org, building interna...
Aug 07, 2025•1 hr 5 min
Have you ever tried running a business like it’s a utility function? Today’s guest has. CJ is joined by Michaela Lehr, a seasoned FP&A leader and former CFO of ActionIQ, who breaks down how CFOs can pull levers like growth, retention, margin, and cash runway to maximize value without blowing something up. Michaela explains how not all growth is created equal and why how you grow matters as much as how much you grow. She talks about gross margin as the most sensitive area of the P&L and h...
Aug 04, 2025•1 hr 6 min
Today we’re reviewing the state of the private markets using the NEW benchmarks released by Mostly Metrics. We surveyed our readers to see how their company’s are doing… And it's tough to be a company between $5M and $25M in revenue right now.Three other things that stood out from the benchmarks this quarter:1️⃣ CAC Payback is up across the board. It’s taking longer to earn back customer acquisition costs. AI is disrupting traditional search channels, and companies are building internal tooling ...
Aug 02, 2025•12 min
How do you keep innovating and disrupting when you’re already the incumbent? And how do you prevent a $200B+ company from becoming slow and complacent? In this episode, CJ is joined by Sandeep Aujla, CFO of Intuit, who shares how one of the world’s largest software companies continues to operate with the agility of a startup. With QuickBooks, TurboTax, Credit Karma, and MailChimp all falling in the Intuit family tree, serving both consumers and businesses, Sandeep breaks down the company’s platf...
Jul 28, 2025•1 hr 8 min
Pricing and packaging has undergone a radical transformation since the early 1950s. And the clear through line is a changing unit of value and how it’s tracked. Historically, the tech industry has undergone six waves of change. * Hardware + Software sold together * Software Sold for Hardware * Application Service Providers * Outsourced Infrastructure + SaaS * Usage Based Pricing * Hybrid We’ll walk through each evolution, and leave you with some tips for overcoming common pricing challenges in t...
Jul 26, 2025•16 min
How do you build a sales culture where top performers are empowered and poor performers are not protected? In this episode, CJ is joined by Daniel Lentz, whose career has spanned sales, taking an e-commerce platform public during a global pandemic, and, interestingly, seminary. Daniel Lentz is the CFO of BigCommerce and an expert in designing comp plans that work. In this episode, he breaks down his approach to this and how to avoid the pitfalls that can easily discourage your salespeople. He ex...
Jul 24, 2025•1 hr 13 min
In this episode, CJ is joined by Chris Greiner, CFO of Zeta Global and former CFO of IBM’s analytics division, where he worked on AI during the development of Watson. He’s had a front-row seat to the evolution of AI across industries. He’s also on a 15-quarter streak of beat-and-raise performance in his current role. Chris breaks down how strong financial stewardship can be a launch pad for innovation, not a constraint, and unpacks his “Closest to code, closest to customer” philosophy. The conve...
Jul 21, 2025•1 hr 7 min
Today we’re talking about capital allocation, and how it’s one of the most powerful, yet least discussed, skills a CEO needs to learn. Every CEO has three core jobs: * Run a good company (Operations) * Tell a good story (Investor Relations) * Deploy capital effectively (Capital Allocation) Most CEOs focus 80% of their time on the first two. Yet it's the third, capital allocation, that often has the highest leverage and the least guidance. You can read more about this topic at lookingforleverage....
Jul 19, 2025•14 min
If you’re an accountant, AI might be coming for your job, but today’s guest believes that there’s never been a better time to be in the profession. CJ is joined by Scott Spiegel, the COO and former CFO of the American Institute of Certified Public Accountants (AICPA). He has decades of experience in finance and leadership at the intersection of business, mission, and membership. He breaks down how the accounting profession has changed and what skills you need to embrace in order to thrive in tod...
Jul 17, 2025•1 hr 2 min
M&A deals usually involve a vast amount of legal fine print, and small oversights can have very costly consequences. To help you navigate this, CJ is joined in this episode by Trey O'Callaghan, a partner in Tech, M&A, and Emerging Companies at Goodwin. Trey breaks down the strategic role M&A lawyers play throughout the deal process in terms of both legal and business advice to help avoid costly missteps. The conversation explores when to involve legal counsel, issues like sales tax a...
Jul 14, 2025•1 hr 2 min
Over the past 30 years, the number of publicly traded companies in the U.S. has been sliced in half, falling from a peak of ~8,000 in the late '90s to just ~4,000 today. That stat shocked me. I knew IPOs were a slow drip, but I didn’t realize that the number of companies being taken private was far out pacing the number joining the NYSE and NASDAQ ranks. Today we discuss: * Three structural changes in the capital markets that brought us to this point * The rise of private credit * How companies ...
Jul 12, 2025•15 min
In the current tech landscape, everyone is experimenting with AI, but when it comes to finance, we tread more carefully. In this episode, CJ is joined by Amy Butte, the CFO of Navan, one of the most AI-forward travel and expense platforms in operation. Amy highlights how the company is weaving AI into its operating system, not just to summarize documents, but to manage financial workflows with real impact. With a career spanning Wall Street and Silicon Valley, Amy also discusses her journey from...
Jul 10, 2025•1 hr 4 min
Elon Musk, Peter Thiel, Reid Hoffman, Max Levchin, David O. Sacks, Roelof Botha, Chad Hurley, Russel Simmons, and Jeremy Stoppelman are among those considered the “PayPal Mafia”. These are cofounders or early team members of PayPal who went on to found or invest in major tech companies like Yelp, Palantir, YouTube, Facebook, SpaceX, X, LinkedIn, Affirm, Airbnb, and others. In this episode, CJ is joined by Jimmy Soni, bestselling author of The Founders , which chronicles the early years of PayPal...
Jul 07, 2025•1 hr 17 min
Figma Figma just raised the bar for IPOs in 2025. Today we break down their revenue, margins, retention, and potential valuation in the public markets. You can find the full analysis in written form at: https://www.mostlymetrics.com/p/figma-ipo-s1-breakdown 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 fixe...
Jul 05, 2025•18 min
In many companies, the CFO is more important than the CEO. And the majority of private equity-backed CFOs are actually not up to par. In this episode, CJ is joined by Scott Engler, of LinkedIn fame, to explain why he believes these bold statements to be true. Scott is the CEO and co-founder of Sync Executive Partners and the co-founder of PE-Xcelerate. He has decades of experience studying, recruiting, and coaching CFOs. He shares insights on the evolving role of the CFO, the many hats they wear...
Jul 03, 2025•1 hr 19 min
The number one thing listeners of the pod ask me for is to flip the script and let someone interview me. I’ve historically been reluctant to do it because it feels little self aggrandizing or whatever the term is. But you gotta give the people what they want. On this episode my friend Mike Wu, founder of Hire Frame , interviews me on my transition to full time content creation. We talk about * How I sold a company as CFO, and then fired myself immediately * Why having supportive partners in any ...
Jun 28, 2025•42 min
The CFO software ecosystem is highly fragmented and ripe for disruption. Sean Jacobsohn, partner at Norwest, has a front-row seat to the action: He’s backed 10 companies selling to CFOs, while Norwest has invested in 20. Having identified 300 companies in 15 different categories operating in the space, he joins CJ to share takeaways from his market map of the evolving CFO software stack. They dig into what’s driving disruption, how new players are challenging legacy systems, and what it takes fo...
Jun 26, 2025•48 min
When the COVID-19 pandemic hit in March 2020, Zoom went from steady growth to hyperscale almost overnight, even generating a backlog of a million tickets. Sarah Riley was a finance leader in the company at the time. She joins CJ to talk about what she learned from the experience and how it impacted her in her current role as CFO of dbt Labs. She also explains the influence of Helmer’s Seven Powers framework on her strategic decisions. The discussion covers how Sarah’s evolved pricing models, and...
Jun 23, 2025•57 min
We’re heading towards a world where Google not only stops sending us traffic, but uses our own content against us. In today’s podcast we discuss how Google’s incorporation of AI summaries into search is changing the shape of the search funnel. For those responsible for making resource allocation bets across their companies to drive new users, this is a fundamental shift. How are you preparing for it? And what are we seeing? Tune in. Run the Numbers is brought to you by Zenskar . Zenskar is an AI...
Jun 21, 2025•14 min
In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it's changing in the era of AI. He explains what the components of a company’s AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you’re preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention...
Jun 19, 2025•56 min
If you work for a software company, odds are that people make up 80-90% of your business’s costs. Today’s guest argues that in order to effectively manage a company’s greatest asset, the CFO should be heavily involved in shaping the company culture. Bill Tole is the CFO of TrustRadius, a trusted platform where tech buyers find real reviews. He is skilled in creating structures around ambition and breaks down how TrustRadius creates and implements Objectives and Key Results (OKRs). He explains ho...
Jun 16, 2025•59 min
This one’s for anyone who’s ever mistaken SaaS metrics for gospel. I sit down (ok, dine out) with two CFOs—one from a dating app, the other from an HVAC parts company—and come away questioning the whole tech-is-king narrative. Turns out, the guy replacing dirty rugs in Georgia public schools pulled in $22 million last year. And no, he doesn’t have a Substack. In this episode: * A billion-dollar business that makes… bolts * SaaS dreams vs. rug-cleaning realities * The myth of “build it once, sell...
Jun 14, 2025•9 min
