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 the Idea Maze to Reinvent Children Education with Ryan Delk

June 8, 2023

Joining us on The Deep End today is Ryan Delk. Ryan is the CEO & Co-Founder of Primer, a startup creating a new education system for children, centered around microschools. Last year, Primer announced that they’ve raised $…

Raising $2.2M to Make Home Ownership Flexible with Lauren Self

May 31, 2023

Joining us today in the Deep End is Lauren Self. Lauren is the founder of Roots Homes, a fractional home ownership company, that allows you to build equity in your home while paying rent, which recently raised a $2.2M seed r…

Housing and Regulation with Kim-Mai Cutler from Initialized

May 24, 2023

Joining us in The Deep End today for our housing series is Kim-Mai Cutler, a partner at Initialized who invests in proptech, real estate, and climate. Kim's background as a financial markets reporter and early-stage venture…

Intro: How to Increase Access to Housing

May 24, 2023

Over the past two years, we've interviewed 100+ people for our podcast, The Deep End. Now we're relaunching The Deep End as a multi-media publication, focused on problems worth solving. In the first series, we are tackling…

From Pivoting to Raising $180M to Build Stripe for Transportation with Vignan Velivela

May 10, 2023

Joining us in The Deep End today is Vignan Velivela. Vignan is the co-founder and CEO of AtoB, a fintech payments platform modernizing the trucking industry’s financial system, which raised a $155M Series B last year. He was…

Curiosity as an Ideation Mechanism with Tory Reiss

May 3, 2023

Joining us in The Deep End today is Tory Reiss. Tory is the CEO and co-Founder of Equi, an alternative investment hedge fund. Tory previously co-founded Archblock, a decentralized alternatives marketplace, and Harvest Money,…