Techstars Sports Accelerator

Jordan Fliegel

Managing Director

Jordan Fliegel is an entrepreneur, startup investor and advisor, and author. He is the Founder of CoachUp, Inc., America's leading sports coaching company, whose online service connects athletes of all ages with private coaches to help them reach the next level in sports and life. As this book goes to press in 2016, CoachUp has more than 16,000 coaches across the country conducting thousands of training sessions every week in some 25 sports. CoachUp has raised more than $15 million in venture funding and won numerous awards, as well as celebrity endorsements from NBA MVP Stephen Curry and NFL star Julian Edelman. In addition, CoachUp has been featured hundreds of times on television and in the press, in outlets such as LIVE with Kelly and Michael, Late Night with Seth Meyers, Fox News, The Wall Street Journal, The New York Times, Forbes, and USA Today.

Jordan also plays several active roles in the startup ecosystem: as an early-stage technology investor in more than 40 startups through Bridge Boys, a seed fund he co-founded in 2012; as an advisor to numerous venture-backed startups; and as a mentor at top incubators such as Techstars Boston and Mass Challenge. He was named to the prestigious Inc. "30 Under 30" list in 2015 and to the Boston Business Journal "40 under 40" list in 2014, and was a finalist for Ernst & Young’s "New England Entrepreneur of the Year" in 2015.

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Notable Investments

Ergatta, Botkeeper, FightCamp

Questions & Answers

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

I founded (backed by $14M VC, Boston HQ) and then was co-CEO of (backed by $6M VC, NYC HQ) which we sold for $48M in 2017. Im co-founder and Managing Partner of Founders First (micro VC fund), and collectively have made 100+ early stage investments over the past 8 years. My experience as a 2X VC-backed founder helped me build friendships with VC partners, angel investors and peer founders, and those relationships form the basis of my deal flow and investing activity.

Investment Approach: What are the key factors you consider when evaluating a founding team?

I like to back teams of high-capacity founders with street smarts, who possess complimentary skills sets, and demonstrated integrity (ie care deeply about their customers, employees, investors, communities), who have had prior key roles on successful teams (whether startups, sports, military, etc).

What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

I try to be hands off, and typically get involved around high-level strategy, prep and intros to other investors for new rounds, and sourcing executive hires. As a founder I benefited most from relationships with other founders who had built bigger companies, and so I try to make a lot of founder-founder intros to our portfolio CEOs.

If I'm coming to pitch to you, what's the one piece of advice you'd give me?

Just be yourself! I want to get to know you are a person, what drives you, what your unique insight is and where it comes from in your prior experience, and what makes your team special.

As an angel investor, how many deals do you aim to do each year?

Between my accelerator, angel fund and syndicate, I backed 25 companies in 2020.

How would you describe your own personal mission and values, and how do they impact the way you invest?

A while back I wrote a personal mission statement (highly encourage everyone to have one): I believe that building successful companies with positive missions is my clearest path to making the world a better place.  Over the course of my life I will positively affect millions of people through harnessing the power of my ideas, ability, energy, relationships, and purpose. My personal mission and values helps me filter who I choose to work with and how I spend my time (ie investing in and mentoring founders).

What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

NYC is obviously one of the best startup cities in the world, and I don't think there is another city that matches NYC's access to talent, capital, industry and nightlife/entertainment for young people setting out to build disruptive companies. Covid did a number on NYC, but it will bounce back. NYC is the heart of capitalism, has leading academic institutions (Columbia, NYU, etc), incredible diversity, and a really engaged early-stage founder/angel/venture community. Most importantly, NYC is a hub for talented immigrants from around the world, who have and will continue to build a disproportionate number of the largest American companies.