Page 62 of The Hard Launch

Jude walks past our bench and they both go quiet. He’s wearing headphones, and whatever he’s focused on has him distracted enough not to notice us. Or he pretends not to.

“You kind of have to feel sorry for the guy,” Dave says, once Jude’s out of earshot.

“Do you?” I ask.

“Maybe he didn’t handle it so well, but this can’t be what he’s been working for all these years. You guys want to go get a cookie?”

Every day I think about walking into Jude’s office to just say hello. Each night I consider texting him to see how he’s doing. But I can see how busy he is, and I know that he’s miserable. It could be that I owe him an apology, only I don’t think I’m sorry.

I’m not sure what we were before, but we’re not that anymore. Instead, Jude and I are just two people who work at the same company.

At least we do for now.

For our next meeting, Faith and Layla have given me a case study to work on. I open it, hungrily; they want me to propose an AI agent that assists families with travel. I promptly send a text to a few people I know with kids, asking them what the worst part about booking travel is for their family. I get a few replies, ask some follow-up questions, then put on my sneakers. Coming home when it’s still daylight means I can walk around my neighborhood, up to the top of Nob Hill and sit in the park and watch people walk their dogs while I think great thoughts about the future of travel.

It’s nice to have a place for my brain to land. I’m surprised at how refreshing it is to have a new problem to solve, one completely separate from email deliverability issues and founders with soft brown eyes who separate your chopsticks for you.

Despite their request that I spend only four to six hours on the exercise, I dig in until I’ve designed a true flywheel, that not only optimizes travel with kids but learns from the customer’s own preferences but also the habits of others with similarly-aged children. The more often you book, the better it gets.

I put a presentation together, along with interactive wireframes and some market data. I practice my presentation on FaceTime for my sister, who doesn’t understand anything about software development but swears she finds my work gripping nonetheless.

I’m ready, then. The only way I know how to make it better would be if I could run it past Jude.

“This is brilliant,” Layla says.

“Truly,” Faith says. “We’re not blowing smoke. It’s fascinating to see your thinking on a problem we’ve been poking at for so long. I’m sort of embarrassed we didn’t come up with this ourselves.”

“Thank you,” I tell them. “I’m sure if we collaborated it would be even better.”

“Absolutely,” Layla says. “Though our goals have shifted since we spoke last. We’ll get you an NDA to sign before we get into the details, but we’re cultivating some major airline relationships right now.”

“We’re going to be so focused on the business side that we’ll be counting on product and technical leadership to just take the reins and build,” Faith tells me.

I nod like it’s exciting, like it’s not filled with unknowns. Such as, what’s the technical leader like and will I get along with them? When there’s a disagreement, how will it be resolved? Do a marketing and an ops person have the focus and vision to lead a software company, especially if they’re busy chasing relationships with airlines?

I tell myself to relax. These are all questions I can ask if I get an offer.

“So what would your timeline be,” Layla is asking me, “if we were to make you an offer next week? Because I don’t want to speak for Faith…”

“No, go ahead, you can.”

“We’ll probably be making you an offer next week.”

I take the bus home and try to feel elated. I shook Faith and Layla’s hands when I left. I told them how much I’d enjoyed working on the case study, how it gave me a real-life feel for what it would be like to solve the type of problems I’d be solving, and that I liked it.

All of that is true, every bit of it. But a pair of founders who uninterested and uninvolved in the product seems like the biggest, reddest of flags. When I pressed them on technical leadership, they seemed cagey and mentioned offshore teams and an open role they’ll be filling soon. Either they’re not trying to build anything more than a sales and marketing operation, or they’re going to perpetually drive the dev teams crazy by not engaging until the last minute, when they surface just in time to swoop and poop.

There’s a small chance that I’m afraid of the unknown. There’s a decent chance I’d be jumping into a shitshow where the team I get to build is miserable and the product I’m working on is stuck together with AI and Scotch Tape.

No job is perfect, but some of them come a lot closer than others. And the one person who can help me make this decision is the person I’d be giving notice to.

I dig my phone out of my bag so I can text Glenn to tell him I need an awful lot of advice, and I see I have a message from Ella, asking me to please call her when I have a second.

I put my phone back in my bag. I’ll find a second later.

At home I sit at my table/desk and check LinkedIn to get an idea for what else is out there. While I’m there I see just how many Lettercatters are requesting and leaving recommendations for me and each other, how many have the public Open To Work setting on. All I can think of is how sad Jude will be if he sees this. The people he wanted so badly to not let down are all softly moving on.

I send the text to Glenn, and then I call Ella.