I gave away half a business to avoid one hard conversation.
New home, new series: everything nobody tells you when you start a business.
Hey y'all,
Quick housekeeping first, then I've got something I've been wanting to build for a long time.
Still Going has a new home. This newsletter now lives on Substack, which means every issue (past and future) lives in one place, you can comment and share, and if somebody forwards this to you, you can join us at the new address:
Yes. That's really the address. I own it, I love it, and if you know me, you know why it fits. More on that in a second, because it's not just a funny URL… it's a foundational piece to something I have been working towards for a while. (I even thought about naming my newsletter "Done Dumber Things"... should I? Hit me back and let me know!)
You don't have to do anything. Your subscription came with me. Hit reply anytime; that still works exactly the same, and I still read every one.
The new series: Done Dumber Things
Here's what I've realized after eight years of building companies: nobody hands you the damn list.
You know the list I mean. Not the "write a business plan, follow your dreams" list. The other one. The list of things that will cost you six figures because nobody told you they existed until you were already bleeding. The list of things that stop your heart and make you question why the hell you started all of this in the first place.
I've paid tuition on that list. Multiple times. So starting with this issue, I'm launching a series where I walk through my experiences; item by item, story by story, scar by scar. I am still going to talk about life and fatherhood and random things on my heart, but some issues will be specific to the Done Dumber Things series. What happened to me, what it cost, what I'd do differently, and eventually, the actual people and businesses I trust and personally use to handle each one. Not affiliates or sponsors. Just the people who actually helped me.
Fair warning: I'm going to be honest about how dumb some of this was. Hence the name.
Let me tell you about my two business divorces (wow I have been divorced alot…smdh)
The first one, years ago with the first business I started: my partner and I stopped seeing eye to eye on the direction of the business. There was no real framework for what happens when partners disagree. So ya know what I did? I basically gave away my half to avoid the conflict.
Read that again. I handed over half a business (that still exists to this day) because having the hard conversation felt more expensive than walking away. It wasn't. It never is. That decision cost me my equity, and worse, it taught me nothing at the time… because I told myself I was "keeping the peace."
The second one hurt more and cost less. Let me explain how that's possible.
In 2021, my original partner at Knowledge Perk and I reached the end of the road together. This was a man I'd shared years of friendship with. Watching that unravel hurt in a way I wasn't prepared for and being completely honest, the process brought out a version of me that was angry, anxious, and checking my email at moments I shouldn't have been. (True story: one of the negotiation emails landed while I was at a Rolling Stones concert. A mentor of mine, in language I'll clean up for print, told me to “put my #&*!@* phone away and deal with it in the morning.” He was right.)
The buyout took over four months. It ended a multiyear friendship. And it was still the best-case version of that story because this time, I had an Operating Agreement.
Your Operating Agreement is divorce papers for your business… written back when everybody still loved each other.
People think an OA is paperwork you sign when you form the LLC and never look at again. Wrong. Mine laid out exactly what happens when a partner wants out: how the offer gets made, how the members consent, how the terms get structured. When everything got emotional (and holy hell did it get emotional and personal) the document didn't care. It just gave us a process to execute and a roadmap to follow.
Without that OA, I'm convinced that fallout would have cost me HUNDREDS of thousands more than it did. With it, the whole thing stayed bounded, unemotional (on paper, anyway), and finished.
That painful buyout became the framework for every partnership since; including my current partnership with Jordan at KP, which is the best one I've ever had. Not because we agree on everything; we don't (and he's usually right). Because the rules were clear before we ever needed them.
The list nobody hands you
Over the coming issues, we're going through all of it. In no particular order:
The Operating Agreement — your business divorce papers (this story, in full)
The right accountant setup — bookkeeper vs. CPA vs. CFO, and why you probably need all three doing different jobs at some point in your business journey.
Real legal representation — finding the attorney who redlines the contract before you're in trouble, not after
Your IP framework — we once discovered our own trademark was sitting in the wrong entity. Fun conversation.
Other people's money — investors, and the strings nobody mentions until the check clears. Every dollar comes with opinions, expectations, and a seat at your table. Some are worth every penny. Some cost you more than the money ever helped.
Buy-sell agreements — and actually funding them — what happens to a partner's equity if they die, quit, or walk away, and where the money comes from
Key man coverage — what happens to revenue if the person who IS the business can't work
Personal guarantees — the debt that follows you home, and your family, if you're not covered (this has caused so much stress)
Disability and income protection — before 65, a long injury or illness is statistically more likely than death. Nobody plans for it. Run your own business and don't have it? You're wrecked.
Succession and estate planning — what happens to the business, and your family, if you're not there
Side agreements and handshake deals — if it's not documented, it doesn't exist. Ask me how I know.
Banking relationships and credit lines — the money you set up before you need it, because when you need it, it's too late (You'd think I would have learned this the first 17 times)
Separating personal and business finances — the boring one that blows everything else up if you skip it
Some of these I learned the hard way. A couple I got right by dumb luck. All of them I wish someone had put in front of me on day one.
Do this one thing before the next issue
I attached a free tool that walks through 11 of these exact questions: partners, buy-sell, key man, guarantees, succession… and shows you where your gaps are. It takes about 3 minutes.
Full transparency: it's from Ember, my insurance company. That's exactly why the recommendations in this series are going to be worth something; I'm not writing about this stuff as a spectator. This is some of the work I actually do now, largely because of everything above. From the companies I've started out of my own need to fulfill what I was missing, to the work I do with the foundation I Co-Founded, I have a real and authentic desire to help others do more with fewer failures by learning from my own experiences and those of others close to me.
Take the 3-minute Business Risk Audit →
Count how many times you answer "not sure." That number is your homework.
Your turn
What's the thing that blindsided you? The clause you didn't have, the coverage you didn't know existed, the handshake that fell apart? Reply or leave a comment. I read every single one; and your story might become an issue in this series.
Still going. Always will be.
Talk soon,
Ryan
Not Quite There Yet Guy
CEO & Co-Founder, Knowledge Perk | Chair, Gravity Center Foundation | EO Charlotte