Run the Numbers

CJ Gustafson
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Aug 28, 2025 • 1h 12min

From Karaoke With Benioff to the Death of SEO: Alex Konrad on the Business of Media

In this discussion, Alex Konrad, a seasoned tech journalist and founder of Upstarts, shares fascinating insights from his career at Forbes. He recounts memorable moments with tech giants like Marc Benioff and explores how they crafted recognition lists like the 30 Under 30. The conversation dives into the impact of AI on media, the evolving relationship between startups and journalists, and the rise of venture capital firms as media influencers. Alex highlights the significance of authenticity in storytelling and the shifting landscape of content creation.
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34 snips
Aug 25, 2025 • 1h 6min

“Stop Trying To Quantify Risk”: Risk Management Wisdom (& Star Wars Analogies) From CISO Andy Ellis

Andy Ellis, former CISO of Akamai and author of 1% Leadership, shares his vast expertise in cybersecurity and risk management. He critiques traditional risk measurement and introduces his 'Pyramid of Pain' framework. Andy discusses the critical dynamics between CFOs and CISOs, the impact of AI on security, and why the roles are converging. Using captivating Star Wars analogies, he illustrates complex risk management concepts and offers insights on strategic security procurement and the importance of evolving leadership skills in this fast-changing landscape.
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Aug 23, 2025 • 9min

Are Fractional CFOs a Grift?

The world of fractional CFOs is booming, but is it all just smoke and mirrors? Discover the common complaints and misconceptions surrounding these services. There's a critical need for startups to align their financial needs with the right CFO engagements. A checklist is shared to help founders navigate this complex landscape and avoid potential pitfalls. Plus, learn about an innovative ERP solution that’s transforming finance functions for modern teams. Tune in for insights that could redefine your investment in financial leadership!
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Aug 21, 2025 • 1h 21min

From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Field

In this conversation, Jonathan Mariner, former CFO of the Florida Marlins and MLB, shares his insights on the financial rollercoaster of professional sports. He discusses how the MLB transformed its fortunes from $500 million in losses to profits, driven by new financial strategies like a luxury tax. Mariner dives into the evolving value of franchises, the impact of streaming on broadcasting, and the challenges of merchandising and international expansion. His journey from basketball to baseball offers a unique perspective on navigating the competitive landscape of sports finance.
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30 snips
Aug 18, 2025 • 1h 6min

Inside the $5B Plaid Deal That Never Happened and the Massive Business Model Transition That Did

In this engaging conversation, Jason Pate, Chief Strategy Officer at Plaid, who played a pivotal role in Visa's $5 billion acquisition attempt, shares insider insights on why the deal fell through amidst pandemic pressures and regulatory scrutiny. He discusses Plaid's transformation into a thriving network business that fuels major fintech players. Jason emphasizes the significance of understanding customer P&L, the evolution of data-driven business models, and the art of negotiation, all while weaving in personal anecdotes and lessons from the world of sports.
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5 snips
Aug 16, 2025 • 7min

Emergency Capital Markets Update: Stubhub IPO (Take 2)

This discussion delves into StubHub's upcoming IPO, highlighting the contrast between favorable market conditions and the company's declining performance. Experts analyze the intricate dynamics of timing versus actual results in public offerings. Is market sentiment king, or does performance take precedence? The implications for companies preparing to go public are significant, raising questions about strategy and timing in uncertain financial landscapes.
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14 snips
Aug 14, 2025 • 55min

Thinking About Adding Payments to Your Software Product? Listen to This First!

Andrew Mosawi from JMI Equity, an embedded payments expert, discusses key considerations for integrating payments into software products. He emphasizes knowing when you have the 'right to win' and building a strong infrastructure. The conversation covers the evolution of embedded payments, strategic advantages in customer retention, and common pitfalls companies face. Mosawi shares frameworks for sizing market opportunities and insights on revenue forecasting, reminding listeners of the complexities and opportunities within the payments landscape.
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15 snips
Aug 11, 2025 • 59min

Having Gone Through Sh*t Is an Asset: Yext CFO’s Playbook for the Tough Times

Darryl Bond, CFO of Yext with a decade of experience, dives into transformative financial leadership. He emphasizes how navigating turbulent times has shaped his approach, prioritizing growth while tackling tough decisions. Darryl reveals the importance of relationship-building as a key to success and discusses how structured processes, like implementing deal desks, streamline operations. He shares lessons learned from mistakes in his early career and underscores the necessity of listening to customers for effective capital allocation.
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Aug 9, 2025 • 8min

An Unholy Alliance

Dive into a riveting exploration of notorious alliances, from Whitey Bulger's connections with the FBI to the surprising ties between AI companies and venture capitalists. Discover how massive capital fuels AI innovation, similar to historical mobster dynamics. The discussion shines a light on Anthropic's recent valuation surge, reflecting the lucrative dance between tech and finance. Along the way, learn about an AI-first ERP solution that's transforming modern finance, making heavy tasks feel effortless.
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Aug 7, 2025 • 1h 5min

How To Win at Early-Stage Sales (With the Guy Who Helped Take Snyk From $0 to $100M+)

Ethan Schechter, SVP of Global Sales and Customer Success at Qodo, previously scaled Snyk's revenue from zero to over $100M. He shares his insights on building a sales organization from scratch amidst the AI boom. Ethan discusses hiring strategies, the emotional rollercoaster of startup life, and the importance of over-communication in early-stage teams. He critiques LinkedIn’s cringe posts while exploring the nuances of discounting as a competitive strategy in the SaaS industry, all while emphasizing trust and adaptability in dynamic environments.

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