In this episode of Nothing Ventured, host Aarish Shah welcomes Mike Bank, the founder of Underdog, a pre-accelerated syndicate aimed at supporting solo and non-traditional founders in launching revenue-generating businesses while maintaining their day jobs. Mike shares insights from his extensive career in investment banking, early-stage VC, and as a prolific angel investor with around 100 early-stage bets. The conversation covers a range of topics, including the simplicity of starting a business today, the importance of viewing business ideas through desirability, feasibility, and affordability, and the challenges faced by founders. Mike also reflects on his experience mentoring over 100 DayZero founders, which led to the creation of Underdog, and discusses the significance of hard work in achieving success, irrespective of background. Tune in to learn more about the evolving landscape of venture capital and the inspiring stories of diverse entrepreneurs. Timestamps: 00:00:00 - Introduction to Mike Bank and Underdog 00:00:43 - Key Topics of Discussion 00:01:29 - Mentoring DayZero Founders 00:01:57 - Aarish Shah's Introduction and Podcast Details 00:02:49 - Mike Bank's Angel Investing Journey 00:04:07 - Diversity in Angel Investing 00:06:12 - Types of Investments in Mike's Portfolio 00:07:01 - Transition from Investment Banking to Angel Investing 00:09:40 - Mike's Early Entrepreneurial Experiences 00:11:09 - Learning from Failed Deals 00:13:00 - The Importance of Work-Life Balance 00:15:01 - The Reality of Angel Investing and Failure 00:17:35 - The Debate on Agency and Success 00:19:09 - The Role of Safety Nets in Entrepreneurship 00:22:20 - The Importance of Taking Risks 00:25:06 - Building an Ecosystem and Paying It Forward 00:27:10 - Leveraging the Internet for Opportunities 00:28:43 - The Simplicity and Difficulty of Starting a Business 00:29:02 - Tim Ferriss and the Real World MBA 00:31:01 - Learning on Someone Else's Dime 00:33:01 - The Concept of Underdog and Risk Management 00:34:06 - The Challenges of Traditional Accelerators 00:36:02 - The Startup Triangle of Success 00:37:54 - The New Way of Building Businesses 00:39:06 - Venture Capital Returning to Its Roots 00:41:26 - The Contrarian View on Venture Capital 00:42:15 - Misaligned Incentives in Venture Capital Find Mike Bank online at: LinkedIn: https://www.linkedin.com/in/mfbank/ Twitter: https://x.com/mikefb Underdog: https://underdogx.co This episode is sponsored by EmergeOne, fractional CFOs for venture backed tech startups from Seed to Series B. Get in touch at https://emergeone.co.uk/contact-us/ or join the CFO team at https://emergeone.co.uk/join-the-cfo-team/ Sign up for EmergeOne’s weekly newsletter, Off Balance at https://off-balance.beehiiv.com/subscribe