Share

cover art for Jason Mendelson on demystifying venture deals

Give First

Jason Mendelson on demystifying venture deals

Ep. 15
•

Jason Mendelson

, co-founder of Foundry Group, can explain what matters in negotiations between entrepreneurs and VCs in just two words: Control and Economics.



It takes enormous expertise to make something complicated really simple, and these bare two words speak to Jason’s profound understanding of venture deals and how they work, for the entrepreneur, the investor, and the lawyers. In addition to being a VC and a company founder himself, Jason has also been a lawyer, a software engineer, and a professional drummer.



Control and economics mean that, in the hundreds of pages of legal documents around an investment, the two things that really matter are control of the company and economic return from the company. Jason and his Venture Deals co-author, Brad Feld, coined this paradigm—and Jason is very proud that it has been used, and stolen, widely.



This is what Jason is most interested in: sharing information. He loves making complex things, like the legal negotiations around VC deals, simple. He works hard to pry open the black box of VC and show everyone how deals get made, and what aspects are most important to the parties involved, whether you’re a startup founder seeking funding, an aspiring VC, or a lawyer diving into the world of venture deals.



Jason has been on this path for over 15 years now. He and Brad started blogging on the subject in 2005, and their book

Venture Deals

first came out in 2011. The fourth edition just published, and Jason explains why they’ve needed every single edition—he cites both better explanations and better writing. Jason and Brad also lead

the free and popular online course, Venture Deals.



Listen for Jason’s insights into the evolution of venture deals, how teaching helps him learn, and, best of all, for the story of a board meeting during which all questions had to be answered with Hall and Oates song titles. See? The professional drummer bit really does connect. 



Get more of Jason’s thoughts, plus a full list of companies, people, and resources mentioned in this conversation.




Techstars personnel and/or guests who speak in this podcast express their own opinions, and not the opinion of either Techstars or any company discussed in this podcast.This podcast is for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. You should consult your own advisers as to those matters. References to any securities are for illustrative and/or informational purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Furthermore, this content is not directed at nor intended for use by any investor or prospective investor, and may not under any circumstances be relied upon when making a decision to invest in any fund managed by Techstars.  Certain of Techstars funds own (or may own in the future) securities in some of the companies discussed in this podcast.

More episodes

View all episodes

  • 112. The Unicorn Reinventing How Healthcare Reaches You with Jon Lensing

    32:13||Ep. 112
    In this episode of the Give First podcast, David Cohen sits down with Jon Lensing, co-founder and CEO of OpenLoop, the unicorn building the infrastructure that lets any company offer virtual healthcare to the people it already serves.Jon shares why he left medicine to reimagine healthcare around convenience, how the company survived a make-or-break pivot when COVID hit, and the mindset he uses to place bold bets without risking the business.He is one of 13 unicorn founders featured in David Cohen and Amir Hegazi's new book, "Chasing Unicorns," which lays out the PRIDE framework behind Techstars' billion-dollar companies.Follow Jon Lensing on LinkedIn - https://www.linkedin.com/in/jon-lensing/Read Chasing Unicorns here - https://www.amazon.com/Chasing-Unicorns/dp/1068476079
  • 111. The Unicorn Giving Parents Peace of Mind with Kurt Workman

    28:18||Ep. 111
    In this episode of the Give First podcast, David Cohen sits down with Kurt Workman, co-founder and executive chairman of Owlet, the company behind the smart sock that tracks a baby's heart rate and oxygen and sends the data to a parent's phone.Kurt shares the personal story that sparked Owlet, the moments that nearly ended the company, and what it took to build hardware that parents and doctors could trust.He is one of 13 unicorn founders featured in David Cohen and Amir Hegazi's new book, "Chasing Unicorns," which lays out the PRIDE framework behind Techstars' billion-dollar companies.Follow Kurt Workman on LinkedIn - https://www.linkedin.com/in/kurt-workman-28707131/Read Chasing Unicorns here - https://www.amazon.com/Chasing-Unicorns/dp/1068476079
  • 110. From a Mall Booth to a Billion-Dollar Unicorn featuring Matt Oppenheimer

    29:38||Ep. 110
    In this episode of the Give First podcast, David Cohen sits down with Matt Oppenheimer, founder and chair of Remitly, the cross-border payments company he grew from a mall booth into a billion-dollar business.Matt reflects on the focus and grit it took to scale Remitly across borders, the fundraising road that tested him, and knowing when it was time to hand off the CEO seat.He is one of 13 unicorn founders featured in David Cohen and Amir Hegazi's new book, Chasing Unicorns, which lays out the PRIDE framework behind Techstars' billion-dollar companies.Follow Matt Oppenheimer on LinkedIn - https://www.linkedin.com/in/mattoppenheimer/Read Chasing Unicorns here - https://www.amazon.com/Chasing-Unicorns/dp/1068476079
  • 109. From Lab Bench to Billion Dollar Unicorn with Etosha Cave

    23:38||Ep. 109
    In this episode of the Give First podcast, David Cohen sits down with Etosha Cave, co-founder and Chief Scientific Officer of Twelve, the billion-dollar company turning carbon dioxide and water into jet fuel.Etosha shares what it really takes to build a deep tech unicorn, from the funding playbook for hard science to the hard calls about focus that shaped the company.She is one of 13 unicorn founders featured in David Cohen and Amir Hegazi's new book, “Chasing Unicorns,” which lays out the PRIDE framework behind Techstars' billion-dollar companies.Follow Etosha Cave on LinkedIn - https://www.linkedin.com/in/etoshac/Read Chasing Unicorns here - https://www.amazon.com/Chasing-Unicorns/dp/1068476079
  • 108. Burn Bright, Not Out: James Oliver Jr. on Founder Mental Wellness

    24:12||Ep. 108
    In this episode of the Give First podcast, David Cohen sits down with James Oliver Jr., Techstars alum, entrepreneur, and author of Burn Bright, Not Out.James shares his journey navigating the pressures of high achievement and the hidden cost of hustle culture. He introduces the Burn Bright Spectrum, a framework to help founders recognize the difference between healthy ambition and burnout, and explains why rest, micro-wins, and alignment are essential to long term success.The conversation explores founder mental health, breaking stigma in the startup community, and how sustainable performance drives deeper impact than constant grind.Follow James Oliver Jr. on LinkedIn ➡️ https://www.linkedin.com/in/james-oliver-jr/ Order Burn Bright, Not Out ➡️ https://www.amazon.com/Burn-Bright-Not-Out-ShatteringThe-ebook/dp/B0GG8FCCQZCheck out the Kabila Founder Mental Health Fund ➡️ https://give.socialgoodfund.org/KabilaMentalHealth?ref=ab_7QGjqr7P0pr7QGjqr7P0pr
  • 107. Finding Your Way Back to What You Love Through Give First with John Fein

    23:16||Ep. 107
    In this episode of the Give First podcast, David Cohen sits down with John Fein, partner at Firebrand Ventures and former Techstars managing director.John reflects on the winding path of his career, from moments of uncertainty to finding renewed purpose through startups, venture, and community building. He shares how small acts of generosity, like answering a random email or making an introduction, can create lasting impact and open entirely new chapters.The conversation explores John’s journey through Techstars, the evolution of Firebrand Ventures and The Hill Fund, and his long term commitment to the Kansas City startup ecosystem. Along the way, David and John discuss imposter syndrome, paying generosity forward, and why Give First is less a philosophy and more a practice that compounds over time.John Fein LinkedIn ➡️ https://www.linkedin.com/in/johnfein/
  • 106. The Long Game of Venture and Generosity with David Hornik

    28:51||Ep. 106
    In this episode of the Give First podcast, Brad Feld talks with David Hornik, founding partner at Lobby Capital.David shares how a relationship driven approach has shaped his career in venture capital, from investing to community building. He reflects on why generosity compounds over time, how trust creates durable networks, and why long term thinking matters in both business and life.The conversation also touches on the origins of the Lobby conference, David’s connection to Adam Grant’s Give and Take, and how the Give First mindset shows up in his work with founders, students, and investors.David Hornik LinkedIn ➡️ https://www.linkedin.com/in/davidhornik/
  • 105. Rethinking Capitalism with Seth Levine

    25:51||Ep. 105
    In this episode of the Give First podcast, David Cohen talks with Seth Levine, Partner at Foundry and co-author of Capital Evolution. Seth looks back on the early days of Techstars, the original Boulder community that shaped it, and how Foundry is approaching its final fund while still actively investing.The conversation explores why so many people are questioning capitalism today. Seth breaks down the decline in economic mobility, the growing wealth gap, and the rise of populism on both sides of the political map. He explains why he believes capitalism can still work, but only if more people have access to ownership and economic participation.Seth also shares insights from interviews featured in his book and highlights ideas like broader employee ownership, baby bonds, and modernized investing rules. He ties these themes back to the Give First mindset and how expanding opportunity can strengthen communities and the future of entrepreneurship.Seth Levine LinkedIn ➡️ https://www.linkedin.com/in/sethjlevine/ Get Capital Evolution here 📖 https://www.amazon.com/Capital-Evolution-New-American-Economy/dp/1637747780 
  • 104. Starting and Closing a Bank in 3 Months with Bala Kamallakharan

    49:08||Ep. 104
    In this episode of the Give First podcast, Brad Feld talks with Bala Kamallakharan, founder of Startup Iceland and a driving force behind the country’s modern startup ecosystem. Bala shares the remarkable story of moving to Mumbai to build an Icelandic bank in 2008, only to watch the entire financial system collapse overnight. Within three months, he went from launching a new bank to shutting it down, navigating canceled credit cards, emergency flights home, and the emotional aftermath of Iceland’s economic freefall.What followed was a personal reset. Returning to Iceland with no clear path forward, Bala began to rethink how the country could rebuild. His belief that new ideas and young founders could reshape the future led him to invest in early startups, create Startup Iceland, and champion the power of community-driven entrepreneurship. That work later earned him the Order of the Falcon, Iceland’s highest civilian honor.Bala reflects on uncertainty, resilience, and why believing in founders can transform not only companies but entire countries.Bala Kamallakharan LinkedIn ➡️ https://www.linkedin.com/in/balakamallakharan