In this episode, Jack Richardson sits down with Chris Tottman to explore his remarkable journey from entrepreneur to investor. They discuss the founding and growth of MessageLabs, its market leadership, and the impact of the 2008 financial crisis on the company. Chris shares insights into founding Notion Capital and its investment strategy, emphasizing the importance of assessing founder resilience and experience. The conversation delves into finding the right balance in founder traits and lessons learned from 15 years in venture capital. Chris reflects on influential board members and shares his personal inspirations. The episode wraps up with a quick-fire round and social media connections.

(0:00) Introduction and guest Chris Tottman

(1:51) Chris Tottman's transition from entrepreneur to investor

(2:33) MessageLabs founding, growth, and market leadership

(9:45) Company culture, scaling, and 2008 financial crisis impact

(16:00) Founding Notion Capital and investment strategy

(24:49) Assessing founder resilience, experience, and support

(31:00) Finding the balance in founder traits

(33:07) Lessons from 15 years in venture capital

(34:57) Influential board members and their contributions

(37:17) Chris Tottman's inspirations and quick fire round

(41:02) Episode conclusion and social media plugs