Can failure be a foundation for success? Want to hear a few hard truths from the CEO of a huge media company?

Meet Medium CEO Tony Stubblebine.

Tony shares his journey through entrepreneurship, detailing the challenges and failures he faced before finding success. He discusses the importance of leadership, team dynamics, and the strategies he implemented to turn around Medium's fortunes. Stubblebine emphasizes the need for entrepreneurs to focus on distribution and finding unique opportunities in a crowded market, as well as the transition from programmer to CEO.

Tony Stubblebine’s career is a testament to persistence, adaptability, and the lessons learned through trial and error. Starting as a programmer in the 1990s, Tony initially pursued a traditional career path, earning a computer science degree and working on projects he describes as “meaningless code.” While he appreciated the stability of a salaried position, he eventually sought a greater purpose and transitioned into leadership roles, ultimately leading him into the world of startups.

His first significant foray into entrepreneurship was with the podcasting startup Odeo, which famously spun off into Twitter. Though he worked on the podcasting side of the business—only to see much of his work discarded—it was a pivotal moment that sparked his desire to control the direction of his work. This led to the launch of his first company, a social networking platform. Despite lacking a clear revenue model or funding, Tony’s determination helped the company achieve break-even status, albeit without significant success. He used this experience as a foundation to grow, learning what worked and, more importantly, what didn’t.

Tony’s next venture, Lyft (not the rideshare company but a habit-tracking app), was far more aligned with his personal interests in self-improvement and productivity. This focus on passion helped him sustain the company through challenges, including a shift into what he calls "aggressively zombie mode" when funding dried up. Even during this period of survival, the app had a lasting impact, influencing the design of modern habit trackers.

Today, Tony is the CEO of Medium, where he’s applied the hard-won lessons from his entrepreneurial journey to revitalize the platform. When he took the helm, Medium was in financial trouble, losing both money and subscribers. By cutting inefficiencies, focusing on growth, and being upfront about the company’s challenges, Tony led Medium to profitability for the first time, achieving over a million paying subscribers. His career illustrates not only the importance of perseverance but also the value of learning from failures to achieve meaningful success.

Key Takeaways:

1. Failure as a Foundation: Tony reflects on his 15 years as a CEO, marked by trial, error, and persistence. From building a social network to creating a habit-tracking app, his journey taught him resilience and focus.

2. Medium’s Revival: Tony took over Medium when it was burning millions and losing subscribers. Through clear priorities—cutting inefficiencies, focusing on growth, and direct communication—Medium turned a corner to profitability with over a million paying subscribers.

3. Counter-Narratives in Business: Tony advocates exploring overlooked opportunities. Medium’s success is built on avoiding ad-driven models and embracing subscription-based growth—an approach that aligns with its audience’s values.

4. Entrepreneurial Insight: From programming roots to CEO, Tony emphasizes the importance of distribution over product perfection and finding allies when fixing broken systems.

Why Listen? Tony doesn’t sugarcoat the challenges of leadership or entrepreneurship. If you’re looking to understand the reality behind building and reviving businesses—or you want a glimpse into Medium’s evolution—this episode is a must-listen.