In Episode #7 of Spectruss Speakeasy, Sam sits down with Jonathan Bragdon, founder of Capacity Capital and a seasoned entrepreneur, to unpack what it really takes to build successful businesses, survive economic crashes, and rethink how we fund early-stage companies.
Bragdon, who helped build and exit multiple businesses (including Tricycle, which exited to a Berkshire Hathaway company), shares personal stories of growth, failure, and resilience. From losing half his customers during the 2008 crash and laying off half his team in a day, to bouncing back with smarter decisions and systems, Jonathan’s experience is raw, real, and full of wisdom.
The two also dive deep into what separates founders who survive from those who thrive: obsession with the problem, T-shaped collaboration, and a willingness to adapt capital strategy. Bragdon emphasizes that venture capital should not be the default funding route, “You’re hiring money,” he says. “It needs to match what you’re trying to build.”
The episode touches on a wide range of topics: creative capital stacks, the danger of overvaluing AI answers, the emotional toll of leadership, and why now, in the wake of layoffs and AI disruption, might be the best time in years to build something new.
Key Themes:
- Real talk on venture funding and dilution
- Why founders should obsess over problems, not headlines
- The rise of AI and the disappearing line between real knowledge and generated content
- Stories from building companies through economic downturns
- The importance of risk, resilience, and asking: “What am I missing?”
Whether you’re a startup founder, investor, or just someone curious about the business-building trenches, this episode is packed with practical takeaways and deep philosophical reflection on where entrepreneurship is headed next.
Listen to Episode 7 of Spectruss Speakeasy to hear Jonathan’s full story:
Watch it on YouTube here
Hear it here on Spotify
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