When PagerDuty went public in 2019, it was generating just $100 million in annual revenue which made it relatively small for a SaaS IPO. One of the main motivations for this was that visibility into the company’s financials would inspire customer trust. In this episode, CJ speaks with Howard Wilson, PagerDuty’s CFO, who shares the unique challenges of going public as a small company, how the landscape has changed since then, and how to approach an IPO when you don’t have the experts you need in-...
Jun 12, 2025•1 hr 5 min
How do you know when a company is ready to go public? And what do you do to prepare for this? Chirag Shah, CFO of Motive and former CFO of Kong and Cornerstone OnDemand, joins CJ to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. He talks about taking companies public and how he helped take one private again in a $5.2 billion deal. In this episode, he explains what signals indicate that a company is ready to accelerate its growth, ...
Jun 09, 2025•1 hr 7 min
The tables are turned: CJ is interviewed by Lilly Wyden, host of the Shared Narratives podcast, to talk about the intersection of tech, finance, and writing. We discuss: * How I found a CFO job via my newsletter * The power of owning specific patches of real estate on the internet * If big Substack writers will have talent agents someday * How the memeification of finance has made the industry more fun and approachable * Whether I would ever write about corporate gossip or finance junk food * Wh...
Jun 07, 2025•51 min
How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum...
Jun 05, 2025•1 hr
Is it true that founders should still own 50% of a company after a Series A fundraising round? Is 10% ownership at IPO a win or a loss? This episode delves into the topic of dilution, breaking down how much of your company you should sell at each stage, how to approach employee and advisor equity, and what employees should know about equity before taking a job. To answer these questions is Peter Walker, Head of Insights at Carta, and someone with a strong read on where the private tech market is...
Jun 02, 2025•1 hr 7 min
Welcome to our inaugural mailbag. I grew up worshipping the mailbags of Bill Simmons (Grantland) and Drew Magary (Deadspin). We needed one of our own. If you have a question for next month, drop it in the comments. And please give us five stars!!! This month’s questions: * Career Screw-up Story – “You ask CFOs for mistakes. What’s yours?” (Matthew from CO) * OnlyFans Valuation – “Is OnlyFans worth $8B?” (Lewis from MN) * Excel Model Versions – “What’s the highest version number you’ve had in a m...
May 31, 2025•19 min
Serving SMB mid-market customers is one thing, but when you go upstream to enterprise sales, everything changes: go-to-market strategy, the sales process, how you structure deals, even how you define customer value. Today's guest, Andrew Casey, has helped scale four SaaS companies: ServiceNow, WalkMe, Lacework, and his current company, Amplitude. At ServiceNow, he worked closely with Snowflake’s Mike Scarpelli and Coatue’s David Schneider, and he was instrumental in establishing the company’s de...
May 26, 2025•1 hr 16 min
Chime, the consumer fintech powerhouse, just filed to go public on the NYSE. On this podcast we’ll cover everything you need to know before they hit Wall Street👇This is a fintech that: → Doesn’t take deposits → Doesn’t lend off its balance sheet → Still did $1.67B (+31%) in revenue last year, mostly from swipe feesIt’s built for the 70% of Americans who live paycheck to paycheck — and earns their trust (and interchange) by becoming the #1 card in their wallet.But here’s the tradeoff: ✅ 88% gros...
May 24, 2025•22 min
To be a great finance leader, one needs to have both hard and soft skills. Today’s guest believes in running towards the hard market, asking dumb questions, and showing up as your whole self at work. Craig Conti is the EVP and CFO of Verra Mobility, the almost $900 million in revenue, publicly-traded company that is responsible for the silent infrastructure behind seamless tolling, traffic enforcement, and smart mobility. Apart from providing a visual breakdown of his approach to mitigating risk...
May 22, 2025•1 hr 15 min
As a CFO, how should the way you navigate risk and return change from venture-backed companies to publicly-traded companies to private equity companies? To answer this question, CJ speaks with Mohit Daswani, a seasoned CFO with experience across multiple stages, including roles as CFO of Payments, Platform, and Risk at PayPal, and Head of Finance & Strategy at Square. Mohit shares the lessons learned from his time at Square, including when Jack Dorsey seeded a second billion-dollar business ...
May 19, 2025•1 hr 11 min
This is going to make all the PLG fan boys & girls angry...Today we talk about why Romanticizing PLG is dangerous.With AI companies hitting $50M ARR overnight (amazing product, credit cards, and a golden retriever named Kevin), a dangerous myth is spreading:👉 “You don’t need a sales team. The product sells itself.”Wrong. That was the dream of PLG. Now it’s become the CFO’s favorite excuse to avoid hiring reps. But romanticizing PLG as a cost-saving silver bullet? That’s corporate delusion.S...
May 17, 2025•15 min
To explain why portfolio operations are increasingly the secret weapon in private equity, CJ interviews Paul Stansik. Paul is the writer of the Hello Operator Substack and Operating Partner at ParkerGale. He shares hands-on insights into how his team helps portfolio companies scale by transforming sales data into decisions, navigating post-acquisition go-to-market challenges, and driving the shift from being merely data-aware to fully data-driven. He also discusses sales teams, from hiring the r...
May 15, 2025•1 hr 8 min
The venture debt landscape has changed dramatically over the past few years, and CFOs can’t afford to be left behind. Catherine Jhung, Senior Managing Director at Hercules Capital and a seasoned expert in venture lending, joins CJ to explore the landscape of venture debt in 2025. Together, they unpack important questions for CFOs approaching lenders, the delicate balance between rate and flexibility, and a surprisingly overlooked use case for venture debt. You’ll also hear when not to raise debt...
May 12, 2025•52 min
This past week I spoke to a group of 50 CFOs at Premji’s CFO Conference. I gave a presentation on how CFOs are using AI to improve efficiencies internally. There’s a lot of information on how to build AI into your product, but not nearly enough on how to use it internally within your company to drive results. Today I’ll take you through that presentation, and a survey I conducted, to show you where AI is being leveraged, and if you are actually behind. For more on the topic visit: mostlymetrics....
May 10, 2025•18 min
When it comes to investor relations, an organization’s communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson and Jon Neitzell of the Arbor Advisory Group, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you've attracted the wrong investors...
May 08, 2025•1 hr 8 min
How does a surf forecasting platform evolve into a multi-pronged company with B2C subscriptions, advertising, B2B SaaS, and even some hardware? Dustan Berg, former equity analyst and current VP of Finance at Surfline Wavetrak, Inc., joins CJ to discuss the evolution of Surfline's business model and the nuances of running this 40-year-old startup. Dustan explains the role of data as a moat and how Surfline navigates retention and increasing wallet share in a business model that’s tied to user ide...
May 05, 2025•59 min
This is State of the Private Markets , a monthly series where we deliver the most compelling valuation , hiring , and revenue insights on pre-IPO candidates . Think of this as your backstage pass to the companies shaping the future before they hit the public markets. Today we will cover: * Valuation: The most valuable private tech companies * Hiring: The fastest-growing teams * Layoffs: Companies making cuts * Sector Highlights: A deep dive into Data Infra , Design Tools , and Direct to Consumer...
May 03, 2025•24 min
Irrespective of the numbers, financial storytelling and strategic communication play a massive role in influencing market perceptions. Hamza Fodderwala, Executive Director at Morgan Stanley, joins CJ to discuss the critical role of CFOs in shaping and communicating a company's financial story. Hamza explains the role of storytelling in driving stocks, the significance of aligning company narratives with prevailing market themes, the metrics that software investor analysts do and don’t want to se...
May 01, 2025•56 min
What's the real difference between a CFO and a COO? Can you do both roles simultaneously? And which title is more desirable from a career perspective? Today’s guest, Colin Sims, who is currently the CFO of Hunters but has held both titles multiple times, joins CJ to answer these questions and to talk about channel sales. They discuss what it takes to build a successful channel sales model and how companies need to “feed the channels" before expecting them to feed the company in return. You’ll he...
Apr 28, 2025•1 hr
Today we give the straight talk on the state of the economy that operators running tech companies need to hear. We cover: * Ripple Effects : Even if your company doesn’t ship atoms, your customers probably do. Expect slower procurement, deferred renewals, and CFOs eyeing legacy tools. * Investor Vibes : Market uncertainty = deal drag. Think longer diligence cycles, cautious boards, and DCF models sweating in real time. * ERP Economics : When Nike gets budget clotheslined, your cloud spend might ...
Apr 26, 2025•14 min
Nick Rose, CFO of Enable, joins CJ to discuss one of the most overlooked yet powerful levers for growth, trust, and alignment in B2B commerce: rebates. They talk about how rebates are often dismissed as accounting clean-up or mistaken for discounts, but they are actually critical pricing incentives that foster long-term relationships. Nick describes how he first came to Enable as a customer and how it helped him uncover more than $7 million in missed rebates. He breaks down how rebates differ fr...
Apr 24, 2025•58 min
Russ D'Argento, CEO and founder of FINTRX, sits down with CJ in this episode to discuss building a Data as a Service (DaaS) business while also sharing insight into the highly lucrative world of family offices. He explains what a family office is (name a billionaire, they probably have one), their roles in wealth management, and how he identified this niche. He sheds light on FINTRX, what it does, and why building a verticalized data business for a niche market can be both exceptionally complica...
Apr 21, 2025•1 hr 6 min
Everyone loves talking about finding product-market fit. But what if the real challenge in 2025 is keeping it? In this solo episode, I riff on why PMF has become more fleeting than ever. I unpack what Harry Stebbings, Jason Lemkin and Rory O’Driscoll observed —companies that once had a five-year runway now fall out of PMF in five weeks. We explore AI-fueled growth curves, the myth of “escape velocity,” and why today's go-to-market edge can vanish overnight. I also shares a brutal hill from a rec...
Apr 19, 2025•7 min
In this episode, CJ sits down with Rob Paterson, CFO of Employment Hero, to talk about smart growth, why not all revenue is good revenue, and Australia's startup scene. They start by discussing when to turn down growth opportunities and which financial metrics are more distracting than helpful. Rob explains the challenges of holding people accountable when you are a growth CFO and how to be a Chief Reality Officer instead of a “CF-No”. He offers a view into the Australian startup ecosystem, high...
Apr 17, 2025•50 min
Rick Smith, multi-time CFO, founder of Bonfire Advisory, and author, joins CJ to discuss the complexities and nuances of the CFO role in venture-backed companies. They delve into the dynamics of the CEO-CFO relationship and examine the qualities CEOs think they want in a CFO versus what they need. Rick introduces the concept of “The triangle of doom” that exists between the CEO, the CFO, and the board, and how to navigate situations when forced to pick sides. Having been a CFO of five different ...
Apr 14, 2025•1 hr 12 min
Welcome back to Run the Numbers. Now that I’m full time, I promised that I’d let you all in on the Business of Mostly Metrics. And chapter of that story is the my own failed startup - Bubba Booking. On this episode we’ll cover ten lessons I learned, how I lost over $200K, and what came of this face plant. Check out our sponsor Gelt, who makes this podcast possible. You can get 10% off year one - https://go.joingelt.com/mostlymetrics At Gelt, they work with CFOs who aren’t just looking to stay co...
Apr 12, 2025•12 min
In this episode, CJ Gustafson sits down with Brad Channer, the CFO of UBIO and possibly the world's most interesting CFO and accountant. He describes his unconventional career path from acting to accounting and the he lessons learned from some entrepreneurial failures along the way. Brad also discusses communication and leadership, including how his acting background shaped his style in the boardroom. He breaks down the biggest mistakes CFOs make when explaining financials and why some accountan...
Apr 10, 2025•1 hr
Sanjay Datta, CFO of Upstart and former senior finance exec at Google, joins CJ to discuss leadership, scaling, and the future of lending with AI. Sanjay spent 12 years at Google, helping grow it into an $80B global ads business. He sheds light on Google’s monetization model, the simplicity of its forecasting, and the power of centralized analytics. He also reflects on scaling Upstart from $10M to $500M, going public, managing investor and employee expectations, and staying agile through macroec...
Apr 07, 2025•1 hr 5 min
Stubhub has filed for it’s upcoming IPO. In this podcast I dive into the meaty details you need to know before one of the most valuable privately held marketplaces makes it’s NYSE debut. We cover: * Business model * Key metrics * Market opportunity * 12 Key themes * 3 Red Flags * Bull / Bear case None of this is investment advice. If you want the full breakdown go to mostlymetrics.com This podcast is sponsored by Gelt. You already know tax season isn’t just a deadline—it's a lever. At Gelt, they...
Apr 05, 2025•17 min
In this episode, CJ sits down with John Connolly, Managing Director at Spectrum Equity, to explore the evolution of consumer investing. They discuss how investor sentiment toward consumer companies has shifted over the past 15 years and why traditional SaaS metrics like net dollar retention (NDR) don’t always apply in this space. John explains what signals indicate a strong consumer business, whether brand or product wins in the long run, and how consumer companies have adapted their monetizatio...
Apr 03, 2025•47 min
