Page 4 of The Hard Launch

I’d correct her about the g-word if I thought it would do any good, but I’ve given up. When people accuse you of being a genius, saying “no, I’m not a genius” only makes them think you’re trying to be humble in addition to being a genius. Despite what Lacey thinks, I don’t do anything to position myself that way, because I know it’s not true. I spent years waiting for the right idea. And once I had this one, I was stubborn enough to stick with it for a while, that’s all.

Stubborn, obsessive, singularly focused. It’s funny how traits that would anywhere else be considered character flaws are the key to success when you’re a founder. It’s less funny when the thing you put so much energy into starts to feel like it can destroy you.

Or how the thing you built yourself turns into something you hardly recognize. I was at an engineering meeting yesterday, and I could barely follow anything they were saying; it’s been that long since I wrote any code. I don’t know that I was aware of how much my life would change once I got the funding I so desperately wanted. I used to make things, but now it’s become my job to trust the team I’ve put together and then get back to my cap tables and board decks.

And meetings. Like the one coming up shortly with a potential partner, followed by my meeting with Glenn, right before I get my ass handed to me by Edmund later this afternoon. I kick my shoes off, turn on my ring light, and get ready to pretend I’m charming. The life of a founder isn’t anything like I thought it would be.

“So what do you think?” Glenn asks. “Are you happy with it?”

I don’t answer right away, something that in my Executive Assessment was noted as irritating or intimidating to some people. But I’m not a fast processor; I need a little time to assess the question, think about it, and answer. I don’t worry about it bothering Glenn, who is one of the few voices of calm, mature reason in my life. The dude is steady and smart. Sometimes I wonder why he’s not the one in charge.

We’re reviewing the roadmap for the next two quarters, essentially making our big bets on what we can build that will get us more users and get the ones we already have, to spend more. Truthfully, these aren’t supposed to be bets. It’s all anchored in research and data, with projections and considerations built in. And what the data says is, we should go all in on multi-author publications and make our platform a true home for online publishing. It’s not what the original vision was, but we evolve, and we listen to our customers.

“The numbers look good. And the research looks solid,” I tell Glenn. “I think Edmund and the board will be pleased.”

“But are you happy with it?”

“I’m happy when Edmund’s happy,” I say.

Glenn sighs and closes his laptop. I’ve frustrated him, I know.

“I’m not denigrating the work! It looks like a terrific plan.”

The glasses come off, the nose bridge gets rubbed. This means Glenn’s about to hit me with some wisdom, and honestly, I need it.

“Jude. I’m sympathetic to you, I really am. You’re in a tough spot, and I don’t envy you. And I don’t want to be the older guy telling you how to run your company, especially considering how things went with the one I started.”

Glenn’s here because he needed to fire-sale his own startup when it tanked. He spent six years building something that ultimately got sold for parts. Edmund was on his board and thought Lettercat would be a nice place for him to land. Glenn saves my ass regularly. He also frequently reminds me how he’s living proof that failure at business doesn’t mean death, which is unfortunately something I often need to hear. I suppose Edmund’s not entirely evil.

“No way,” I tell Glenn. “Your experience and advice mean a lot to me. Hit me with whatever you’ve got. No gloves, I can take it.”

He laughs. The top of his head comes up to my shoulder, so my metaphor doesn’t really land.

“You’re trying to please the board. You’re trying to please the customer. You’re trying to do right by your employees.”

I nod. All these things are true.

“But you have all those things—a board, customers, employees—because of a thing you built yourself. Using your judgment. When I ask you if you’re happy, it’s not me wanting you to pat me on the head and agree with the plan I laid out. It’s me wanting your judgment. You have agency here, man. Don’t let that get away from you.”

Glenn’s close to teary-eyed with this plea. I know it’s personal for him. He wants me to learn from his mistakes, and a lot of his advice is tinged with his own regrets. So I tell him the truth: that I never wanted corporate customers. I wanted to build the opposite of that, something regular people could use to share their ideas and stories with the world. Looking at a roadmap so far removed from that mission bums me out a little. It makes me wonder what I’m even doing all of this for.

“What are you doing it for?” he asks me.

I swallow hard. Because the truth is, having eighteen full-time employees is the most terrifying thing that’s ever happened to me. Eighteen people relying on my competence to pay their rent or their mortgage, provide their health insurance, buy their groceries. I’m afraid of failing for all the typical, ego-driven reasons, but the impact my failure would have on all these people is more than I can think about for too long.

“I’m doing it to build something that people want. And pivoting is part of the start-up game. I can’t get too precious about the mission. We need to listen to the data, and if this is what the data says we should build, then we do it.”

He nods. I’m aware that my goal in life has become not failing, which is something very different from succeeding.

“How about I get Trevor in here to review the numbers with you in-depth before we go all-in and bring it to the board,” he offers. “This is mostly his work, and I’m sure he’d love to hash it out with you.”

“Okay.”

“But then I want to pull Lacey in too, to serve as a counterpoint. She has an idea she’s really passionate about and she’s getting a strong signal, but the numbers just don’t compare with these. You might want to hear her out and see if it lights more of a fire for you.”

Oh god.

Glenn looks at me with a raised eyebrow, and I realize I’ve said this out loud.