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This past weekend, Chicago celebrated the annual TechWeek Conference at the Merchandise Mart. The conference was full of successful entrepreneurs sharing their stories and the aspiring taking in every word. On Monday, I attended Style 2.0: Lifestyles of the Fashionable & Web Savvy panel with Rick. The presenters were Brian Spaly (CEO of Chicago’s Trunk Club), John Wiseman (CEO of Jack Threads), Raaja Nemani (CEO of Chicago and Dashfire’s BucketFeet), Daniel Saynt (Socialyte CEO and co-founder) and Zach Davis (Co-Founder of Stylitics). We also ran into our friends Swapna and Swathi from Luxemi.
The take away for me was that most entrepreneurs do not succeed. Running your own ventures with limited resources is hard, painful, and lonely. As Brian alluded, everyone in your life will counsel you against starting your own company as it’s “legal gambling on your career.” But that didn’t stop Brian from founding Bonobos and TrunkClub. Why? Because he cares deeply about the e-commerce and fashion space – will Gilt Group go public, who will Amazon acquire next, what will Nordstroms pay for next. His passion is his motivation.
Raaja had a similar experience before co-founding Bucketfeet. He was an investment banker but after meeting his future co-founder, Aaron Firestein, while volunteering in Argentinian slums, he realized his passion was elsewhere. Raaja and Aaron started BucketFeet to follow their passion for discovering underground artists. And of course shoes. The challenge for Raaja was accepting that in this career path that failure is a real possibility. “Taking your first plunge [as an entrepreneur] is getting comfortable with the idea that you may fail” explains Raaja. “You must recognize that the worst thing that could happen is failure, which isn’t too bad.”
So, do you want to start something?
p.s. if you haven’t already, check out what these fashionable entrepreneurs started:
