Troy Henikoff Speaks: Why You Should Be An Entrepreneur

Three speakers, three weeks. Investment club members are being treated to a delicious course of professional advice and experienced insight; the first dish, which may end up as the one members remember long after this trio, Troy Henikoff, was a presentation crafted and executed to perfection.

Henikoff stepped into N112, comfortably appearing in hiking boots and a Kellogg business school quarter-zip, and already a buzz of innovation and business excitement could be felt. As scores of members packed into rows of seats, Troy (as he insists people call him; he doesn’t like “Mr. Henikoff”) confidently examined his audience, then estimated that his speaking time would be forty minutes. He would hit this number almost exactly, and those forty minutes gave listeners a view of a mighty, intelligent business titan, a man who had brought entrepreneurial rain to the desert of Chicago startups, planting the seeds of a technological revolution. Here is a summary of that wonderful period of time:


Troy argues that he had always been an entrepreneur. As a kid, he mowed lawns, did odd jobs, and ran a paper route. He spoke affectionately of his youthful aspirations of sailing, the graceful sails upon the water; young Troy wanted a boat, and, with the help of a friend, purchased a $200 sailboat, paying half of that, only borrowing $17.  Sailing, as it turned out, was a passion for Henikoff, who became the vice-commodore of Brown’s sailing team, and who even wanted to design sailboats for a living. Taking mechanical engineering classes on his way to a degree, Henikoff had the first of many important epiphanies in his business career; watching the America’s Cup, a glorified sailing championship, and seeing the $70 million sailboats with their aerodynamic design crafted for the sole purpose of circling around quicker than an opponent, made Henikoff reconsider his destiny.


Fresh out of Brown, with his degree, Henikoff approached General Dynamics. They courted him, taking him out for a nice meal, flying him in, before making him a generous job offer; yet he refused. Henikoff would not be imprisoned in a cubicle, with sterilized office-white walls as the only landscape. After taking the advice of a friend (that friend was Michael Krasny who would later grow his company into the multi-billion dollar CDW,) Henikoff had another one of those awesome epiphanies: he moved to Chicago, and started his own company. With no venture capital, his company doubled every year, and was eventually bought by Medline. At each business endeavor thereafter, Henikoff succeeded: “You Don’t Know Jack” sold five million CD-Rom copies, SurePayroll went from being a napkin-scribble to a surefire business which sold for over $115 million, and various data instruments became integral in the way large companies (Google, Yellow Pages) run their businesses. Despite this success, a nagging ate at Henikoff. Chicago, his beloved city, was considered a fly-over country for venture capitalists going from coast to coast; an entrepreneurial desert, parched by the departure of successful startups to other locations.


Inspired by TechStars, a tech-accelerator he had seen in Boulder, CO, Henikoff co-founded Excelerate Labs. Each year, he would bring in business professionals at the top of their fields to mentor the participants, guiding them towards entrepreneurial success. At the end of each session, each of the startups would offer a pitch; “Demo Day,” as it has come to be known, is attended by flocks of venture capitalists and Chicago-area financiers, allowing the entrepreneurs to raise the capital necessary to sustain and expand their businesses. Excelerate has been so successful that it has merged to become Techstars Chicago.

Listening to Henikoff’s list of Chicago startups, one gets the sense that the Chicago-area has gone from a desert to an oasis; Next Big Sound is revolutionizing the music business, Grubhub had an IPO of more than $3 billion, Telnyx, NexLP, Simple Relevance, Trunk Club, GameWisp; the expansive membership heralds a new age of technological innovation. GiveForward, one of Troy’s favorites, raises money for people who are sick and need help paying for medical costs, care, etc; he shared a story of a high school community attempting to raise $10,000 through GiveForward in order to help a terminally-ill, Leukemia patient receive the high school graduation she deserves. Henikoff, who in the early stages of Excelerate made less than a Starbucks Barista, isn’t in it for the money; he loves helping young entrepreneurs, and impacting the world in a positive way.


Forty minutes was up, and the presentation ended with a thunderous applause reaching decibel levels only attainable by a room full of Investment club patrons. “98% of value is execution; 2% is idea” was one of his final quotations.  In N112, as in his programs with tech-accelerators, Henikoff planted seeds, preparing the future generation of entrepreneurs for incredible innovation.

Mr. Henikoff with Club President Noah Silverman
Mr. Henikoff with Club President Noah Silverman

This post was written by Ben Osterlund. Photos by Benjamin Silverman, edits by Noah Silverman.



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