In the last two years, Blaine has become one of the most prolific angel investors in the country. He previously founded Student Brands which he bootstrapped with his co-founders and ran as CEO then chairman through acquisition by Barnes and Noble in 2017. Blaine also co-founded Solve which completed the summer 2017 Y Combinator batch and was acquired later that year. Beyond his success as a founder and investor, Blaine is a deeply thoughtful, humble, and curious human willing to speak openly about numerous aspects of the founder journey and his experience on the investor side. If you have ever felt like investors are ‘the other’ or out of reach, this conversation may be deeply helpful.

Gaurav Bhattacharyya (Co-Founder and CEO of Involve.Ai) shares the very human side of his leadership journey over the last 18 months.

Involve recently raised a $16M round, but a year ago, the founders considered shutting down the business.

We explore impostor syndrome, navigating hard decisions and conversations, and inviting your team and board into the company's most difficult questions.

Sarah is the founder of S’well, maker of arguably the world’s best water bottles. Sarah and I talk about her realization she no longer wanted to stay in the CEO role at the company she founded as well as her decision to eventually conduct the search for a new CEO openly on social media. We also explore leading a team through transition and how to find support in your own big questions.