These past 12 months, I've operated in a way many post-MBAs would scoff at.
Last summer, I launched a chess startup alongside a part-time coaching business.
Time to put the side hustle to the side. Coaching is cute and all, but now it's time to do the "real thing". Short-term cash make way for a VC infusion, podcasts, conferences...
...except for the part where I did the exact opposite.
I leaned into Leland and built a fully-fledged coaching practice with their help. I don't operate with a safety net; I can't raise a "family and friends round" at the drop of a hat.
Not to mention, I think my own parents would be harder investors to convince than most VCs who see stamps like Stanford University Graduate School of Business and McKinsey & Company and think they mean something when it comes to starting a business.
(NB: It's 2-0 VCs on the 'term sheets received' scorecard. Turns out mom needs to see more MoM before any allowance comes through)
But even if I accept that I've missed out on growth these past few months at TownSquare Chess by leaning into my coaching practice, here's what I've learned:
1. As someone who built their own freelance practice before, ?????????? ???????????????? ???? ?????? ??????????????: every time you coach someone, be great. You can't be perfect, but go above and beyond.
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2. ?????? ?????? ???? ???? ?????? ???? ???? ???????? ?????????? ??????: know that you represent an organization, even if you're not an FTE: if I come up short, ???? ???????? ???? ???????????? ?????????? ???? ???????? ???????? ?????????? ???????????? ???????? ??????????. Care about that, and it will come back around.?
3. ??????'?? ?????????? ?????? ??????????: you need to really like doing it. Don't manufacture meaning just to fool yourself. Only coach on things you (a) are skilled in helping, and (b) where you feel super-invested in the outcomes of everyone you're helping. I do free events all the time and come away with more energy than I started with.
4. ???? ???????? ???????????? ?????? ???? ????????: define a niche, dig in, and build a layered offering with multiple options. Accumulate testimonials and your practice will grow itself.
5. ??????'???? ???????????????? ?? ???????????????? ????????????: I've learned how to better build my own marketplace, what great customer focus looks like, and how to differentiate a product in my time with Leland. What more could you want from a "side hustle"?
I'm not about the thing that people say to do. I'm about the thing I learn the most from and the stuff I'm excited to get up in the morning to do. In a world where everyone has GenerativeAI at their fingertips, I decided to start my coaching work at Leland around ??????????????. Turns out it's a more valuable skill than ever.
Oh and one more thing. This "side hustle", this "coaching thing", is now what's allowing me to scale TownSquare Chess in 2024. One marketplace fuels another — financially and intellectually.
Just do your thing.