Q&A: Chicago entrepreneur coaches LGBTQ-owned businesses

Kristina Wynne became immersed in Chicago’s small business community as a 16-year-old working at her family’s Calumet Heights pharmacy, called 200 Pharmacy.

Wynne, 35, now runs her own company The Wynners Club, which provides consulting to startups and early-stage businesses. But it’s in educating entrepreneurs that she’s found her passion.

Last month, Wynne kicked off her fifth year running an eight-week business boot camp for the LGBT Chamber of Commerce of Illinois. The annual program was developed by Wynne in 2019 with the chamber's former executive director Jeromé Holston.

Wynne meets with a cohort of 10 to 15 LGBTQ small business owners for four hours each Saturday, helping them develop business plans and practice investor pitches as well as bringing in expert speakers. At the end of the program, the entrepreneurs compete in the LGBTQ+ Biz Boot Camp OUT-Pitch Competition, where first- and second-place winners receive grants of $2,500 and $1,000, respectively.

“It’s exciting for me to know, 'OK, this is week one, but wait ’til you see yourself week eight,'” Wynne said.

She recently spoke to the Sun-Times about how the program has grown and why it matters to Chicago's business community. This interview has been edited for length and clarity.

Q. How did you get involved in the chamber's program?

A. I created the curriculum, and [the previous executive director of the chamber] really helped structure the programmatic side, as far as the external professionals that we partner with. So I actually was a part of the creation team five years ago. It’s so cool to see how it’s continued to evolve and grow and pull in different partners and different entrepreneurs from all over the city.

Q. With this being the fifth year of the program, how has it evolved?

A. The first year, as amazing as it was, when I look back I’m like, “Oh, man. I just had a really good group who was mature enough to apply the information.” But it was not as structured as year two through five. At first, it was a six-week course. Year two through five, we turned it into an eight-week cohort to now be able to have very clear outcomes for those participants, which is a fully fleshed out business plan, which is really like a 30-, 40-, 50-page document.

Q. What has it been like working with entrepreneurs?

A. I’m an entrepreneur so I just understand the ebbs and flows of being a solo entrepreneur. I can empathize, and I can offer insight and wisdom on ways to deal with it. I’m doing the interview alongside other people from the chamber so I get to understand — before they are actual participants — what they have going on and where those pain points are. This cohort is very, very cool. We have some service-based businesses, some product-based businesses, we have somebody that has been on "Shark Tank." They all get a mentor. I know that they're going to do well on the other side once they get all of these amazing resources and information under their belt.

Q. What challenges do participants face that are unique to the LGBT community?

A. You have to have a [certain] level of confidence to be an entrepreneur. You are, most times, the salesperson. You’re the face. The lack of confidence is higher in the LGBT community. A lot of the work that comes along with this cohort is some mental shifts about how they are seeing themselves; how they’re seeing themselves as entrepreneurs, specifically, how to be empowered and confident.

Q. Where do you think the lack of confidence comes from?

A. Most industries are going to be heterosexual dominant, so [they're] already feeling different. But there is a push and a move for the LGBT community to be more integrated into the business space. We focus on their elevator pitch. We practice that every single week, twice a day, so that at the end of it they are more confident speaking about their businesses, which is going to make them more confident in other areas of entrepreneurship as well.

Q. You’ve had a lot of business success stories like Taylor’s Tacos, crowned best taco in Chicago by "Good Morning America," and powerlifting gym Goals Not Dreams, which recently opened its second location in Austin, Texas. How does it feel to see them do so well?

A. Oh, that’s what I do it for. Honestly, it’s more of a ministry for me. I just feel like God allowed me to be exposed to these things, not for me to keep it but to really share. People don’t know where to begin most of the time so when I can see tangible impact, that’s what I do it for. So yeah, it’s everything to me.