Why I wrote Founder Fallout

People ask me why I wrote a book about equity. They want a marketing answer. I don't have one.

I wrote it because I have watched four partnerships end. Two of the endings were planned. Two ambushed me. Both times I was the last person in the room to see it coming.

That is the whole reason. Everything else is footnote.

The first one that ambushed me

The first ambush came out of a room where I thought we were building something. The paperwork said we were. Cash was moving. Product was shipping. My name was on the wall.

Then the wall changed. I found out from a lawyer.

I am not going to name names in this piece. The reason is not that I am hiding anything, but that a founder who spends the rest of his life pointing fingers is a founder who never builds again. The point is that I signed the paperwork that let it happen.

Every clause that hurt me was in a document I had signed. Every carve-out that mattered was in a section I had skimmed. Every trigger event that got pulled had been sitting there in black and white for years, waiting.

I didn't lack a lawyer. I lacked a list of questions.

The second one that ambushed me

You would think the first one would have taught me. It did, in the way pain teaches. What it didn't do is give me a checklist.

The second ambush was different in the details. Same in the shape. I signed papers I understood clause by clause but did not understand as a system. I trusted a person who was trustworthy inside the deal and dangerous around the edges of it. I ran a company that could survive the market and could not survive its own governance.

By the time I realized what was happening, the moves that would have saved me were three years in the past. There was no unwind. There was only how much I was willing to lose to walk out clean.

What I started doing after

After the second one, I sat down with a legal pad and started writing every question I wished someone had asked me before I signed anything, in plain English questions, not legal terms.

Some were about equity. Most were not.

They were about assumptions. About what happens on a bad day, not a good day. About what your partner does when the numbers are ugly, when their family is stressed, when they get an offer, when you get an offer, when you disagree in a way that will not go away.

The list grew. It kept growing. I hit thirty and thought I had it. Then I remembered a fight from 2016 and added six more. Then I talked to another founder who had been through the same shape of ending and got twelve more.

I stopped at one hundred because a hundred is a number you can finish. One hundred questions is a workable number. There is nothing magic about it.

Why a workbook, not a memoir

I did not want to write a book about me. Nobody needs another founder memoir. What I needed, back when the first ambush was still in front of me and I did not know it yet, was a workbook.

Something you could sit down with, alone or across a table, and just answer. Question one. Question two. Question three. If you could not answer, you knew where the gap was. If your partner could not answer, you knew where the gap was.

The book has a hundred questions and almost no prose between them. That was on purpose. The value is what you say when you look at the question.

Who told me not to publish it

Two people I respect told me not to publish it.

The first told me it would make me look bitter. That anyone who reads a hundred equity questions from a guy who has been through four partnerships is going to assume he is the bitter one, not the wise one.

The second told me it would tank future deals. That the sharks in the market would see the book and assume I had trust issues. That my next deal would be harder because of it.

I heard both of them. I published anyway.

Here is why. I am writing this book for the founder who is right now, today, sitting across from a person who wants their equity, not future deals. That founder wants to know what to ask before the pen hits paper, and won't care whether I look bitter or wise on the way there.

If publishing this makes me a harder deal, good. I would rather do business with people who read Founder Fallout and want to talk about the questions than with people who see the book and get quiet.

Who this book is for

It is for founders. It is for co-founders. It is for the operator who is about to be handed a slug of equity and is not sure what strings come with it. It is for the family member who is being told to sign into a family LLC. It is for the friend who is being asked to invest.

It is also, and I will say it and mean it, for a couple sitting at a kitchen table before they get married. That is the biggest partnership most people ever enter. The questions in the book are equity questions, but the shape of them works for anyone about to bet their name on someone else's decisions.

Every partnership has a shelf life. Founder Fallout gives you the questions to ask before the clock starts running on yours.

The part nobody warned me about

The part nobody warned me about was the aftermath. Both ambushes were bad. What came after was worse in ways I did not expect. The legal fees kept coming for a year after the disputes were resolved. The tax cleanup took two years. The reputational drift with mutual friends of the partners took three. Every one of those years was a tax on the original mistake of not writing enough down on day one.

If founders knew how long the tail of a partnership dispute lasts, most of them would spend more time on the front end. They don't know, because the founders who have been through it stop talking about it, and the ones who have not been through it cannot imagine what years of legal, financial, and emotional cleanup feels like. Founder Fallout tries to shorten that tail by making the front-end work impossible to skip.

Why a workbook instead of a lecture

I chose workbook format because a lecture does not survive contact with a real partnership conversation. You can read a chapter of business advice, agree with every word of it, and then sign a paper the next week that contradicts every word of it, because the paper was written by a lawyer using different language than the book. A workbook forces you to draft your answer in the exact form the paperwork will use. That is the only kind of prep that survives the room.

The questions in the workbook are also written to be handed to your potential partner. You answer, they answer, you compare. That comparison is where most of the value is. A lecture cannot do that. Only a workbook can, and only if the workbook is priced low enough that the two of you can each buy a copy without thinking about it. That is why the book is twenty-four dollars and ninety-nine cents and not one twenty-nine. It is designed to be bought in pairs.

What I hope you do with it

Buy it. Don't read it. Work it.

Sit down with a pen, at a table, alone or across from the person you are about to sign with. Answer question one. If it opens up a fight, that fight was already there. You just found it before it cost you the company.

Do that with all one hundred.

If, at the end, you still want to sign the paperwork, sign it. You will sign it with your eyes open and with a document you will actually be able to defend in a hard conversation two years from now.

If you don't want to sign it, don't sign it. That is the point.

The compressed paperwork version of what the book covers is the seven-move co-founder equity playbook. That is the short-form version of the same discipline.

I wrote Founder Fallout because I have paid the tuition for these questions in cash and in years. You don't have to.

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