From Politics to Venture Capital, with Colin Van Ostern

The Sydcast

Episode Summary

Careers zig-zag, they don’t go in straight lines. But yet there is a thread that connects our paths over time. This is true if you run for Governor of New Hampshire, grow one of the top online education universities in the US, or lead the biggest collection of angel investors in the country. And it’s true if you’ve done all of these things, as we’ll find out in this conversation with Colin Van Ostern.

Sydney Finkelstein

Syd Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College. He holds a Master’s degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 25 books and 90 articles, including the bestsellers Why Smart Executives Fail and Superbosses: How Exceptional Leaders Master the Flow of Talent, which LinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.” He is also a Fellow of the Academy of Management, a consultant and speaker to leading companies around the world, and a top 25 on the Global Thinkers 50 list of top management gurus. Professor Finkelstein’s research and consulting work often relies on in-depth and personal interviews with hundreds of people, an experience that led him to create and host his own podcast, The Sydcast, to uncover and share the stories of all sorts of fascinating people in business, sports, entertainment, politics, academia, and everyday life.

Colin Van Ostern

Colin Van Ostern is an entrepreneurial general manager with experience leading high-growth ventures and teams. Through many different sectors, he has maintained a focus on successfully democratizing access to previously exclusive markets – ranging from higher education to venture capital, consumer goods, tech, and even politics & government.

Currently, he serves as President & COO of Alumni Ventures, a network-powered venture capital firm which in 2021, was the third-most active venture investor in the world (as per Pitchbook Global League Tables). Previously, Van Ostern was on the founding executive team for Southern New Hampshire University’s online College for America, which he helped launch and grow to more than 10,000 “nontraditional” students and graduates nationwide.

Outside of business, Colin was publicly elected twice to New Hampshire’s five-member Executive Council (which serves as a board of directors for the state government), where he was the first Councilor in state history to share all state contracts online for public comment. In 2016, Colin was the general election nominee for Governor of New Hampshire.

Early in his career, he helped elect several members of Congress, Governors, and US Senators in New Hampshire. He holds an MBA from the Tuck School of Business at Dartmouth and a BA in International Studies from George Washington University. He lived in 16 different houses while growing up before moving to New Hampshire after college. Colin today lives in Concord, NH, with his wife and two boys.

Insights from this episode:

• How Colin got into politics
• What prompted Colin to run for office
• Why Colin didn’t win his race for governor
• Similarities and differences in political and entrepreneurial leadership
• Colin’s thoughts on online education as a business model
• Insights into online learning
• Colin’s involvement with Alumni Ventures
• Colin’s shift from politics to venture capital
• How Colin got his job at Alumni Ventures

Quotes from the show:

• “When you see a way things can be better, that you are passionate about and you have a clear picture of how you could positively impact things, you shouldn’t hold back” -Colin Van Ostern [14:23]
• “I think frankly I didn’t offer a compelling enough reason for people to understand in a sentence or in a moment why this race mattered to their lives and why having me as Governor would be different” -Colin Van Ostern [17.06]
• “When you are launching something new, you have to have a vision of the future that you are so convinced has to happen that nothing can get in the way, even failure” -Colin Van Ostern [19:18]
• “There is so much information available, and so it's possible for some of us to get real knowledge about something in a very cost-effective way on their own terms” -Syd Finkelstein [29:58]
• “The best versions of online education, I believe, are significantly better than the worst versions of in-person learning, but I have never seen an online experience that comes close to a good in-person experience” -Colin Van Ostern [31:42]
• “I think content is the smallest part of education in 2022; I think it’s really important, but they're a very small number of thought leaders who are driving new content” -Colin Van Ostern [32:51]
• “Good online education can still be better than in-person learning and we should be honest that there is bad in-person learning” -Colin Van Ostern [37:34]
• “The folks who have to work twice as hard are accomplished people worth betting on” Colin Van Ostern [55:28]

Stay connected:

Sydney Finkelstein

Website: http://thesydcast.com

LinkedIn: Sydney Finkelstein

Twitter: @sydfinkelstein

Facebook: The Sydcast

Instagram: The Sydcast

Colin Van Ostern

LinkedIn: Colin Van Ostern

Twitter: ColinVanOstern

Facebook: Colin Van Ostern

Subscribe to our podcast + download each episode on Stitcher, iTunes, and Spotify.

This episode was produced and managed by Podcast Laundry.