Whether you stay on post-transaction, become an investor or write a book, there’s a lot to be excited about after your hard work results in a successful sale.
by Rob Weber, Great North LabImage result for midwest

With so many great startups getting acquired or going IPO here in the Midwest lately, one wonders: What do these founders do when they score these big windfalls? Do they do the kind of flashy things coastal entrepreneurs do? You know, like buy an island or a 100-foot yacht or something?

Turns out, a lot of my Twitter followers wondered, too, when I did a little survey. Sure, following your passion, changing the world, building a great team — all that stuff matters. But capitalism brings rewards to those who work so hard. And money is definitely one of those rewards. No shame there.

As a managing partner of an early stage fund that is “by founders, for founders,” I know many entrepreneurs who have had life-changing exits. We have several who are investors in — and advisors to — our fund. So I thought it would be fun to ask a range of them about their first moves. Or their second and third, for that matter. The answers may surprise you.


One deservedly famous entrepreneur in Chicago is Kristi Ross, co-founder of tastytrade, which will join the ranks of the city’s $1 billion exits with its recently announced acquisition by online trading platform IG Group.

Kristi is no stranger to the world of successful financial services startups, as she previously co-founded Thinkorswim, which was acquired by TD Ameritrade in 2009 for $606 million.

What did Kristi do for herself post-exit? “I am a minimalist,” she told me. “Time is more valuable than money. And if you don’t have your health, you have nothing. So in celebration, I bought myself a brand new pair of my favorite black Nike running shoes.”

But her personal life has caused her to reflect and make a difference. “Raising three amazing girls while balancing mergers, acquisitions and capital raises, I wanted to ensure my daughters were exposed to philanthropic efforts, always striving to make a difference,” she said. So I wrote a book — Lots of Knots — as my first book of a series for busy moms that want to introduce their young children to philanthropy, showing that little hands can make a big difference. Proceeds are donated to charity.”

Kristi takes her role as a female leader in Chicago and the tech industry very seriously. She especially wants to pave the way for others. “Supporting the future generation of entrepreneurs is important to me – whether that is through our show at tastytrade called Bootstrapping in America, or angel investing behind the scenes or giving time to help advise and mentor.”

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