Run the Numbers

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,...

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, inv...

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...

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...

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...

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 th...

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 “s...

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 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 th...

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 h...

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 innova...

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...

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 mi...

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 change...

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 rea...

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 j...

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, recrui...

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...

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...

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 diffe...

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...

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 lands...

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. I...

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 mor...

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...