The Deep End

The Deep End

The Deep End by On Deck is a podcast where visionary builders, creators, and experts discuss world-changing ideas. We skip the surface level and go in depth into ideas that matter including the futures of commerce, higher education, art, governance, longevity, and more with some of the most exciting figures in these fields. The Deep End is hosted by Marshall Kosloff and produced by On Deck—where top talent go to accelerate their ideas and careers. Visit for show notes and additional essays.

Recent Episodes

Navigating Fundraising and Financial Diligence with Sasha Orloff

March 22, 2023

On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of [Puzzle](, a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the…

Minn Kim on Small Group Theory and the Gift of Global Talent

March 8, 2023

Joining me us the Deep End today is Minn Kim. Minn spent a few years as an investor at Ridge, Bloomberg Beta and On Deck, backing founders as early as possible and is now building Plymouth to help extraordinary talent immigr…

Village Global’s Solarpunk: Erik Torenberg on How Startups Can Help Save The World

March 2, 2023

Last week in The Deep End we spoke with David Booth, CEO of On Deck. Today we're continuing our mini-series on the meta problem of how to help more people start more companies by re-publishing an episode of the Solarpunk pod…

Why is Now the Time to Start a Company with David Booth

Feb. 22, 2023

David Booth is the CEO of On Deck, a curated community designed to increase your odds of building a successful venture-backed company. In this conversation, we discuss why On Deck is doubling down on IRL programming, why he…

Telling Your Professional Story with Heyo’s Vivian Chen

Dec. 15, 2022

Vivian Chen is the CEO & Founder of Heyo, a bite-sized pitch platform for professional success. Before starting Heyo,Vivian was an operator who built products across categories from high-growth startups to global enterprises…

Building Web3 Projects on the Frontiers of Emerging Markets with Ani Pai

Nov. 18, 2022

Ani Pai is an investment partner at Dragonfly, where he focuses on highly technical Web3 projects in emerging markets. Ani believes that progress happens on the frontier. Whether it be outer space, the mind/body, and the oc…