Everyone has thought about going into business with their best friend at some point or another—even if it was just that time in preschool that you had an entrepreneurial itch to start selling macaroni necklaces on the playground or undercut the lemonade stand down the street by a nickel per cup. As adults, though, tackling co-ideation, co-financing, and pretty much co-everything involved in starting a business with a friend is much more complicated and can feel at once daunting and exciting. But it’s still not impossible to successfully hack the very unique relationship that is “co-founder and BFF.”
Best friends Stephanie Simbari and Elizabeth Kott know this well as the co-creators and voices of That’s So Retrograde, a podcast at the intersection of pop culture and wellness that launched its first episode back in early 2015. “It started as the show that we would want to listen to,” says Kott of the podcast’s early beginnings. Five years later, the pair still considers themselves the very best of career partners and friends. The podcast stoked their twin flames—and neither one has burned out.
The duo has plenty of advice to offer any friends on the precipice of a lucrative, fulfilling partnership. Below, Simbari and Kott—along with career coach Maggie Mistal—share their best tips for combining your personal life with your career ambitions.
5 tips for starting a business with a friend
1. Acknowledge each other’s strengths—they will become the business’s strengths, too
We all have our strong suits, and Simbari, Kott, and Mistal all agree that your business strategy should center those core strengths above all else. “In the beginning, Stephanie was a comic. I was an entrepreneur in fashion, coming from a PR background and working in a digital fashion space for a number of years,” says Kott. “What we love so much about That’s So Retrograde is it really feels like this melting pot of both of our strengths and our passions. Stephanie is just so good at just getting on the mic and speaking her truth while I’m really good behind the scenes.”
Once you’ve talked in a more abstract way about each other’s strengths, Mistal says you can dive into the nitty-gritty details to see how those skills translate to your shared business. Ask questions like, “Are there areas of the business we are each more passionate about than others?” and “What roles will we each play in the business?” and “Are there responsibilities that it makes sense we share? Others we should divide?” If your co-founder loves numbers while you love production, they can balance the books while you bring your business venture to life, for example.
2. Use compatibility quizzes to learn more about one another before you kick off your co-career
When two friends approach Mistal with the idea of starting something together, she always recommends they take quizzes and assessments that will help each learn more about one another, be it through the Five Love Languages, Myers-Briggs, or another model that speaks to both of you. “It can help each person understand the other’s preferred communication style,” she says. “This will enable and empower each person to best communicate and be understood while also limiting the opportunity for miscommunication and misunderstanding.”
In true That’s So Retrograde fashion, Simbari and Kott regularly use astrology to learn more and more about one other. “Just recently, we had someone read our charts together because I was feeling so unmotivated,” says Simbari. “I was feeling guilty, Elizabeth was feeling driven. Then someone read our charts, and they were like, ‘Oh, this is where you guys are both at.’ And then we were like, ‘Okay, cool, great. We can drop this.’ No big deal.”
Any tool that helps you better understand one another—whether it’s a personality assessment, astrology reading, or otherwise—will be an asset to your relationship and the business.
3. Work directly with a career coach
“I think that it’s important when you’re working with a friend to get to the place where you can feel comfortable speaking your truth. That takes work, and I really recommend bringing in a third party to be able to hold space for those conversations,” says Kott. “We work with an incredible business coach, Amina AlTai. She’s based in New York, and we do a yearly workshop with her that goes over our broad-strokes goals for the next year. Then we do check-ins with her about just kind of how we’re doing and all of that,” says Kott.
4. Check in with each other on the regular—and know when it’s time to just be friends
It’s important to keep a boundary between friend time and work time, otherwise you run the risk of letting your business arrangement overtake your personal friendship. “Schedule fun time where you can just hang out and enjoy each other’s company as friends,” says Mistal. “By compartmentalizing your time at work, you can still leave room for your friendship.” After all, you were friends first.
During the workday, you can also look out for each other as friends by honoring what the other one needs. For example, if your co-founder needs time off, they should feel like they can come to you so you can make a plan for that to work, and vice versa. “Remember that you’re friends at the end of the day,” says Simbari. “We get so caught up in achievement and our ego and what things look like, but just ask yourself, ‘Why did you start this in the first place?'”
5. Go with the flow as your business evolves
So sorry to all the Virgos out there, but, as 2020 has made abundantly clear, you just can’t plan everything in life, and businesses are no exception. Your business will never be a stagnant thing—and you’ll have to roll with the punches (and delights). Kott says that COVID-19 changed the That’s So Retrograde business, but ultimately, it was for the better. “We were no longer going into a studio, and we no longer had this schedule that we were working off of, so it was a huge opportunity to reframe. And in the process, we’ve completely retooled the structure [of the show]. Now, we’ll do two weeks straight of interviews that will then sustain us for a month to two months of shows,” says Kott. Just like a friendship, a business grows with change.
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