In this episode of Nothing Venture, host Aarish Shah sits down with Oli Harris, a partner at Dream Ventures, to explore the intriguing parallels between poker and venture capital. Oli shares his background as an entrepreneur and discusses the unique approach Dream Ventures takes in investing, leveraging a gambler's instinct to identify elite technology and consumer companies. The conversation delves into the challenges founders face when transitioning to CEO roles, emphasising the importance of adaptability and delegation. Oli highlights the significance of being a great fiduciary, building trust with both founders and limited partners (LPs), and the impact of larger funds on investment strategies. Tune in to gain insights on what makes a successful founder and the evolving landscape of venture capital. Timestamps: 00:00:00 - Introduction to Nothing Ventured 00:00:10 - Oli Harris: Entrepreneur to VC 00:00:57 - Transitioning from Founder to CEO 00:01:37 - The Role of a Fiduciary in Venture Capital 00:01:57 - Investment Strategies and Founder Characteristics 00:02:49 - The Poker Mindset in Investing 00:03:15 - Networking and Understanding Human Behavior 00:04:53 - The Importance of Adaptability in Founders 00:05:59 - The Challenges of Scaling a Business 00:08:09 - The Difference Between Building Revenue and Building a Business 00:10:58 - Self-Awareness in Founders and CEOs 00:12:07 - The Unusual Journey of Founders 00:13:44 - The Anti-VC Approach of Dream Ventures 00:16:05 - Pragmatic Money Management in Venture Capital 00:17:51 - Understanding DPI and Trust with LPs 00:20:10 - The Three Tiers of Investment Portfolio 00:21:07 - The Importance of Early Exits 00:22:14 - The Reality of Venture Capital Returns 00:24:10 - The Shift in Venture Capital Attitudes 00:25:19 - The Velocity of Money and LP Relationships 00:30:10 - The Challenges of Fund Size and Investment Strategy 00:31:56 - Evaluating Founders: Process and Intuition 00:35:10 - The Human Element in Venture Capital 00:38:07 - The Mental and Emotional Toll on Founders 00:40:01 - The Dangers of Shiny Object Syndrome 00:42:05 - The Importance of Focus in Startups 00:44:58 - Normalising Cashing Out for Founders 00:46:08 - The Future of Secondary Investments in Europe Find [guest name] online at: LinkedIn: https://www.linkedin.com/in/oliharris/ Twitter: https://x.com/ohchopper Dream Ventures: https://www.dreamventures.com/ 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