The Founder's Journey: Risk, Resilience, and Rewards | Sam Silvey and Jonathan Bragdon

Spectruss Speakeasy Podcast

In this episode of Spectruss Speakeasy, Sam Silvey sits down with Jonathan Bragdon, founder of Capacity Ventures, to explore the contrarian approach to venture capital in today's economy. Jonathan shares his journey from building and exiting companies to launching a venture fund focused on capital-efficient businesses in the Southeast.

With decades of experience as both founder and investor, Jonathan offers invaluable insights on the relationship between founders and capital. He challenges conventional wisdom with his "hiring money" philosophy—the idea that founders should view fundraising as bringing on a partner rather than chasing validation.

The conversation covers the psychology of entrepreneurship, the importance of T-shaped team members, and why economic downturns create the perfect environment for startups. Jonathan also explains why raising less money and maintaining optionality often leads to better outcomes for founders.

Whether you're a founder looking to raise capital, an investor seeking better returns, or simply curious about the venture world, this episode provides a refreshing perspective on building successful companies in today's rapidly changing landscape.

#VentureCapital #Entrepreneurship #Startups #BusinessGrowth #Investing

Chapters

1. Taking Risk in Early-Stage Investments (00:00:00)

2. Building Tricycle: Changing an Industry (00:05:14)

3. Surviving the 2008 Market Crash (00:16:07)

4. The Emotional Cost of Business Layoffs (00:23:48)

5. The Venture Capital Philosophy at Capacity (00:34:31)

6. Raising Money: Venture Capital vs. Other Options (00:46:29)

7. Founder Obsession and Problem-Solving Mindset (00:59:48)

8. AI and Its Impact on Knowledge (01:09:24)