Run the Numbers

Mike Wu, founder of Hire Frame and host of the What Worked podcast, interviews CJ Gustafson, a former CFO turned full-time content creator. They dive into CJ's journey after selling his company and immediately firing himself. The conversation highlights the pivotal role of supportive partners in entrepreneurship and the creative process behind his newsletter, Looking for Leverage. They also discuss the struggles of audience engagement and the significance of compound effort in achieving success. Their insights into the intersection of finance and content creation are both engaging and thought-provoking.

Sean Jacobsohn, a partner at Norwest, invests in tech firms targeting CFOs and runs the Failure Museum, showcasing lessons from failed companies. He discusses the fragmented CFO software landscape and emerging disruptors challenging legacy systems. Jacobsohn shares insights on successful partnerships, the significance of domain expertise, and evolving tools like automated expense management solutions. He reflects on the six forces of failure and emphasizes the importance of learning from missteps to drive innovation in finance technology.

Sarah Riley, CFO of dbt Labs and former finance leader at Zoom, shares insights from her time navigating hypergrowth during the pandemic. She discusses the challenges of scaling operations and adapting financial strategies amidst skyrocketing user signups. Sarah highlights her strategic use of Helmer's Seven Powers framework to drive decisions. The conversation touches on evolving pricing models, integrating AI in finance, and converting finance teams from 'doers to reviewers', all while balancing efficiency with innovation.

The discussion centers on the drastic changes in search technology driven by AI, highlighting the repercussions for content creators. There’s a spotlight on ethical challenges linked to uncredited content and the need for innovative strategies in digital publishing. As Google’s influence wanes, the conversation emphasizes community engagement and diverse revenue models as essential for survival. It’s a call to action for businesses to rethink their approach amid this evolving digital landscape.

Alex Immerman, a Partner at Andreessen Horowitz, dives into the shifting landscape of the CFO role influenced by AI. He emphasizes the necessity for CFOs to adopt a founder's mindset and leverage AI to reshape financial frameworks. Alex discusses the stark differences in metrics between AI-native and traditional SaaS companies, underscoring the significance of LTV to CAC ratios. He also shares insights on what makes exceptional CFOs, their dynamic with CEOs, and the transformative challenges they face as they prepare for IPOs in an AI-driven world.

Bill Tole, CFO of TrustRadius, shares his insights on the critical role CFOs play in shaping company culture, particularly in software organizations. He discusses the importance of aligning Objectives and Key Results (OKRs) with team dynamics, emphasizing creativity and collaboration. Tole explains the difference between KPIs and OKRs and underlines how ambitious yet achievable goals foster innovation. He also introduces the Rule of 40 and highlights the necessity for financial literacy among employees to drive success.

Dive into the world of unconventional business success as two CFOs share insights on profitable ventures outside the tech bubble. Discover surprising tales, like a rug-cleaning business raking in millions without the high-tech frills. Challenge the myth that SaaS is the only path to riches, and explore how traditional industries can thrive. The discussion critiques hustle culture and highlights the importance of tangible results over flashy pitch decks. It’s a reminder that success can be found in the gritty details of everyday businesses.

Howard Wilson, CFO of PagerDuty, brings a wealth of experience from his role as chief commercial officer. He shares insights on the unique challenges remote public companies face and how customer trust plays a pivotal role in financial transparency. The conversation dives into innovative financial practices, the importance of customer-focused metrics, and adapting to market shifts post-IPO. Howard also discusses the significance of empathy in leadership and collaborative finance teams, along with humorous anecdotes about quirky expense claims that lighten the mood.

Chirag Shah, CFO of Motive and a whiz at guiding firms through the IPO process, shares his expertise on scaling businesses from $30M to nearly $1B. He dives into the crucial signs that a company is ready to grow, the balance of growth and efficiency, and the pitfalls of expanding sales teams too quickly. Chirag also discusses the emotional rollercoaster of IPOs, achieving great valuations, and whether going public is the right move. His insights provide a roadmap for navigating the complex landscape of hypergrowth and public markets.

In this engaging discussion, Lilly Wyden, host of the Shared Narratives podcast, interviews CJ about his journey from investor to CFO. They delve into the power of newsletters for career advancement and speculate on whether Substack writers will soon need talent agents. CJ shares insights on the memeification of finance, making it more fun and accessible. The duo also discusses the potential effects of corporate gossip on content creation and the importance of authenticity in brand partnerships.