Chapter Two
JUDE
Six meetings down and three more to go.
Only fifteen minutes until my next one, which was going to be plenty of time to make it to Blue Bottle for a coffee and back.
But no way am I going to head there now.
Nope, I’m going to walk two extra blocks to a Starbucks and probably be late to my next call, just to avoid my own employees. How’s that for executive leadership?
Edmund James, big-shot venture capitalist and chairman of Lettercat’s board of directors, would be horrified but unsurprised.
He’s constantly telling me I need to be a killer, a winner, and a warrior if all of this is going to work out.
I lie awake at night stressing about that, in addition to dozens of other issues Edmund thinks would be rectified if I could only change everything about myself.
The sad thing is, I didn’t even want coffee.
I heard where they were heading when they passed my office, and I thought if I went to Blue Bottle too, I might end up in line behind them, and Lacey and I could toss around some ideas about where else we can improve engagement.
It seemed less awkward than walking over to her desk and striking up a conversation.
At least it did until I hit the down button for the elevator and got yet another perspective on everything that’s wrong with me. Get in line, Lacey Lang.
But she certainly does have her head around our user data; the way she was spouting out stats reminded me of the days when I first started Lettercat, when I was obsessed with our customers and nothing else.
Back before my days were a blur of cap tables, board decks, and trotting around begging venture capitalists for money.
I’ve tried to explain to Edmund that I’m a killer and a winner and a warrior when it comes to building things—that’s why there’s even a company here to run—but he says those are problems for other people now.
I’m so focused on the forest that I never get to see the trees.
I couldn’t tell you what was in our last release.
And apparently that’s for the best, since I can’t ask a Product Manager a question about a new feature without inspiring an angry elevator TED talk.
It took me a second, honestly, to compute that the person she was spouting off about was me.
All I did was ask a question. I thought that was why we have an All Hands in the first place.
But I had my AirPods in, giving me plausible deniability that I heard anything she said.
So sure, my Executive Feedback Assessment said I can be conflict-avoidant at times and identified open dialogue to resolve challenges as an opportunity for my professional growth.
Maybe I’d do some soul-searching on that if I didn’t have three more meetings this afternoon and a deck I’d claimed was mostly done when it isn’t even started. I have an outline, though. In my head.
I imagine what Edmund would have me do in this situation.
He’d say I should fire her on the spot. Don’t tolerate gossip or insubordination or people who question your authority.
He would absolutely not recommend scuttling off to Starbucks to wait in a too-long line for a coffee that’s going to sit and get cold on my desk.
Fine then, I’ll take a walk around the block.
It’s not weird to go back to the office empty-handed.
Steve Jobs used to go for walks all the time.
“Where’s your coffee?” Jonnie asks when I get back. I forgot I’d told her where I was going. She keeps my schedule up on an iPad on her desk so she can make sure I’m at my meetings on time, and any last-minute departures get her a little worked up.
I look down at my hands, like I’m expecting to see a coffee there or something. I shrug and walk into my office, hearing her cluck to herself about absent-minded geniuses and how it’s a wonder I remember to put on my jeans each morning.
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.
“She’s really talented,” he says.
“I don’t disagree. I’m sure she’s smart. She seems a bit… hostile, is all.” And defensive, I could add, but I don’t. Also, abrasive and unprofessional.
He blinks a few times. Puts those glasses back on and stands up.
“I’ll go grab Trevor. But regarding Lacey—you might think about how your feedback lands when it’s delivered in front of the entire company.”
“So I’ve heard,” I say after he leaves the room.
“I’ve been told Jude wants to take a look at my spreadsheets,” Trevor is telling Jonnie in a fake-sexy tone.
“Just go in,” Jonnie tells him.
I know he can be obnoxious, but Trevor is my guy.
I love this dude; I brought him on board as my first employee as soon as I could make a hire.
Back in college, he was starting companies left and right, doing things as an undergrad that I thought we weren’t allowed to do until we had a diploma.
When I told him about my idea for Lettercat, he was the one to ask me why I was talking about it instead of building it.
“What are you waiting for?” he said.
Trev has confidence and moxie, but when the first investors came on board, they were more interested in experience.
Trev’s more of a Swiss Army knife than a specialist; he’s moved from Ops to Sales to Product.
But he’s been cool with working under Glenn, says he’s learning the right way of doing stuff so in his next company he can fuck shit up and do it all the opposite.
“Bro,” Trevor tells me.
“Bro,” I reply.
“We build this shit, and you’re not talking Jimmy Jo-Bob’s Antique Newsletter anymore.
We’re not making shit for that lady who draws a cat every day and sends it out to two hundred people.
We’re talking marquee-level shit. We’re talking Lettercat is the platform for major news outlets, media corporations.
Sports teams. High volume, big dollars. That means courtside, ringside for you and me. All of it.”
“Show me the data,” I say. And he does. For forty minutes I dig in and find his ideas are solid, the numbers are beautiful.
I’d be an idiot not to follow this direction.
It’s what’s going to usher in our new era and, more importantly, it’s what will get me that next round of funding we so desperately need.
It’s the type of growth the board has been pushing for.
“You love it?” Trevor asks me.
“I love it,” I say.
I message Glenn and tell him this same thing. And then:
Me: Hey did you ask the other product manager to brief me on her idea?
Glenn: Sure did, asking Jonnie to find some time for Lacey and you.
Me: Tell her not to worry about it. We’ll go with Trevor’s vision
I see the bubbles indicating that Glenn is typing something, and while I have better things to do, I’m curious what he has to say, so I wait. And wait. Then:
Glenn: OK
I wonder what he typed out before he wrote that instead. No, that’s a lie. I know exactly what he was typing: do I love the idea, or do I love the projected results? Because there’s a difference between those things, a difference Glenn thinks I should spend more time exploring. But I can’t.
It’s time for me to steel myself for Edmund.
I’m a killer.
A warrior.
A winner.