Boothie Starts Podcast For Entrepreneurs

Last November’s presidential election in the United States changed the paths of many. Crissy Costa, who will be graduating with her MBA from the University of Chicago’s Booth School of Business this weekend, is one of them.

The election was partially responsible for Costa quitting her dream job and starting a podcast called 52 Founders. Since the first week of last December, she has interviewed a company founder nearly every week to learn what makes them entrepreneurs. So far, she’s spoken with 27 — and drawn a big following.

She’s also learned lot. One of the most important lessons, she says, is something she’s experienced in her own life: that entrepreneurs are “practical risk takers.”

STARTUP BEGINNINGS

Costa knows “practical risk-taking” well. After graduating Johns Hopkins University with a degree in international relations, Costa, 29, quit a job at Deloitte to switch coasts and work for a small startup in San Francisco, then quit it to work at another startup, then quit it to enter the full-time MBA program at Chicago’s Booth School of Business.

“When I graduated in 2010, it was a radically different time and I got a job working at Deloitte,” she recalls. After a couple years, the financial modeling gig grew old. Costa was bored and did what many bored consultants do — she took the GMAT. Through the application process, she realized that she didn’t want to go to B-school without a plan. And she didn’t have one.

But her older brother, an entrepreneur, was an inspiration to Costa, so she decided to dabble in the startup scene. If she could wear many hats at an early-stage startup, she reasoned, she’d get a better idea of what she actually wanted to do. A friend of a friend tipped her to a potential option at Peek, a travel booking platform.

“I got my job over Skype and moved to San Francisco two weeks later without knowing anyone out there,” Costa says. “I think once you do that once, you become fearless and know everything will work out.”

INSPIRATION FROM AN UBERPOOL

Soon she learned her next important lesson.

“That’s when I realized I liked product and B2B more than consumer products,” Costa says, noting that she ended up working more hours for the startup than for Deloitte. After a little more than a year, she moved to Xamarin, her first key experience at a mobile app development software venture. “The nice thing about living in the Bay Area is, all your friends work at startups,” Costa jokes, adding that another friend of a friend was instrumental in her getting the second job.

With the expiration date on her GMAT score rapidly approaching and a better grasp on her professional interests, Costa decided to go ahead and apply to B-school. Within a week, she met a local entrepreneur in an UberPOOL. After a conversation that spanned the amount of time it takes to travel through Chicagoland in an UberPOOL, Costa was convinced to check out the world of venture capital — and by the start of her second semester, she had secured an internship with Lightbank, a Chicago-based VC firm.

Costa loved it.

‘I WAS SET TO DROP OUT OF BOOTH. I WAS 100%.’

Through Lightbank, Costa met the founders of Ionic, Max Lynch and Ben Sperry. She was wowed by their founding story and impressed enough by their product that she began working as their part-time director of growth — while also working at Lightbank and still in the full-time MBA program at Booth. Something had to give. Costa decided it would be school. “I was set to drop out of Booth. I was 100%,” she says. Costa met with school administrators, the donor who was funding her scholarship to attend Booth, and her friends.

“Booth is one of those schools that lets you finish any time in five years,” Costa reasoned. Plus, “I’ve never really taken the regular business school path. It’s just never been an interest to me. I wanted to win the New Venture Challenge, drop out of school, and start a company.”

This was the closest opportunity to fulfill those dreams. The donor and administrators were on board. Her friends threw her a going-away party. And then the second week of last November happened. The election results rocked Costa’s world even as Ionic was soaring — it had raised a massive $8.5 million Series A round earlier in the year. Their intentions were to hire a chief operating officer — a position that would surely influence Costa’s role in the venture.

Suffering from burnout and peeved from the election results, Costa changed course. She quit the job.

“It was my dream company and then my horror scenario of what’s happening to the country. I was at an all-time low,” she recalls. “I would have to give up my scholarship at Booth to be unsure about who my boss would be in a few months and unsure about my future with the company.”

‘THE COMFORT ZONE IS A MISNOMER’

Three days after the election, Costa attended SeedCon, a venture capital event hosted by Booth’s Polsky Center for Entrepreneurship and Innovation. She also attended FounderCon, hosted by Techstars. Through those events, she had a pair of realizations.

First, she knew her life would revolve around entrepreneurship and venture capital. Second, she knew she wanted to learn the stories of entrepreneurs and learn from them. Costa was also moved by something said by Neil Stevenson, the executive portfolio director at IDEO: “The comfort zone is a misnomer,” he said. “It makes us think it is a great place to be. Instead it should be called the zone of cowardice.”

In her introductory blog post, Costa explains what Stevenson’s words meant to her: “Rather than rest in my comfort zone, I decided I would go back to the girl of my youth, the one that constantly asked questions and voraciously consumed stories, to uncover what really is in a founder’s DNA,” she wrote.

And from the “all-time low,” a passion baby was born.

LESSONS FROM THE SERIES

Costa started with her own network and published her first podcast, a conversation with James Amable of Union Crate, on December 6, 2016. She has since branched out to “cold asking” founders of startups she admires. So far, Costa says, she has yet to hear a “no” from anyone — even her latest cold ask via Twitter direct messages.

Through the process, Costa says, she has picked up on a few more lessons. “There is this trend of not being afraid to start over and reinvent yourself,” she says, “people that moved around constantly and kind of had to figure out how to fit in or just said, ‘Screw it, I’m going to be myself,’ or just adapt to the environment.”

Even if the podcast doesn’t stretch beyond the 52 founders she plans to interview, Costa, who is recruiting for a venture capital position, doesn’t at all regret her zig-zag path through business school.

“I have no idea what I would have been doing with all of my free time in business school,” she says. “Probably the homework that I should’ve been doing.”

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