Chapter Twelve
JUDE
I wish someone had told me that starting a company is like getting on a ride that you think is going to be fun, only to find, thirty seconds in, that you hate this awful ride that will take all your time and become a substitute for your life, and that in the best case scenario, you can’t get off for years.
I’ve had highs and lows, demonstrated questionable judgement with one employee, and almost cried over another, and that’s just since the alpha demonstration, two very long days ago.
I arrive at the office and pause to remind myself of Glenn’s insistence that we celebrate the wins.
The continued existence of Lettercat counts as one of those.
As does the overall positive energy I sense around the office lately.
Glenn’s family is fine, and I was up late making real progress on the next phase of the ad network.
If Lacey’s in the office today, I can tell her some news: I think she’ll be able to launch a beta in the next week.
And speaking of Lacey, I’m thankful we’ve moved on with no signs of fatal weirdness from the other night. I will be careful going forward.
It’s going to be a good day, I silently tell the Lettercat sign.
I badge in and stow my helmet under my desk, plug my laptop into my workstation, and go look for my water bottle, which I have a bad habit of leaving all over the office.
I find it near the foosball table, where Dave and I played a few points while sorting out the caching problem he wanted my thoughts about.
I’m heading to the kitchen to fill it up when I see Jonnie walking out, carrying a coffee and a bottled water. The ones we save for guests. She looks rattled.
“Good morning,” I tell her, because it is one.
“You didn’t see my messages,” she says.
My eyes revisit the water bottle in her hand.
Edmund is here, and he’s waiting for me in the conference room.
“Am I crashing your party?” he asks me, after I’m done shaking his hand and over-boisterously telling him what a great surprise it is to have him here.
“Not at all,” I say. “We’ve got some great stuff going on. I can show you if you like.”
“Absolutely. Sit down,” he says, gesturing to the chair across from him. “But let me dial Wally in first.”
This is when I know for sure that this isn’t a friendly drop-in, or a helpful unannounced coaching session. Edmund will hand me my ass in those settings regularly, but when he’s after full course devastation, Edmund likes to have an audience.
“Wally, I’m here with Jude.”
“Hello Edmund,” Wally’s voice says from the speaker on the table between us. “Jude.”
“Good morning, sir,” I say, still pretending to be jovial.
“I was just about to ask Jude how he’d feel if someone took one-point-four million of his dollars and then stopped answering his calls,” Edmund tells the telephone.
“Ah,” Wally says. “I’d be interested in knowing that answer myself.”
“Oh, gosh. Not my intention,” I tell him. “I apologize. I’ve been so busy trying to hit that deadline that I suppose I could have communicated better. Always happy to make time for you both.”
I feel like such a loser spouting these blatant lies, and I know all of it is what Edmund wants. It’s not enough for him to take you down, he wants to see you do it to yourself.
“And therein lies the crux of the problem,” Edmund says with a smile, relaxing back into his chair. “Remember that video about the triangle I sent you, Jude?”
I nod.
“Let’s do a little refresher. Play it again for me here.”
I find the link, share my screen, and we watch the little cartoon about the Karpman Drama Triangle that we’ve talked about before, which is apparently the cause of all problems that exist at Lettercat and is a direct result of my leadership or lack thereof.
Villain, Victim, Hero. I am always required to self-identify after a viewing.
“Hero,” I say when it ends.
I was the Victim the last two times, I am not sure this is progress.
But the lecture is different at least. I’m in the weeds, I’m told.
True leaders do not go into the weeds and solve the problems, so how do I explain my current situation, where I’m spending my days writing code?
How do I think the company is suffering from my lack of leadership?
What is the opportunity cost of me behaving like an engineer instead of a CEO?
I don’t tell him that I’ve been forced to write code because of a possibly arbitrary deadline he gave me in order to continue funding the company; that’s a ticket to the Victim lecture.
Instead I try to recast myself as a Warrior, because it’s good to be one of those.
I assure him that I’ve got a great team with me, that I am being a Killer in the weeds as I lead my amazing team of warriors to a win.
I’m not sure if I’ve convinced him or confused him, but he seems to be considering this.
“It’s true that outside of you and Glenn, I don’t know too much about who you’ve got on board here.”
Then he says he looks forward to meeting this team of mine. He’s going to play nine this afternoon but will be happy to take us out for steaks tonight; it’ll give him a chance to get to know the team.
“Ahem,” Wally says. “Jude’s a vegetarian.”
“He’ll find something,” Edmund says, and he hangs up.
“Bro,” Trevor tells me. “We’re fuuuucked.”
“Conference room,” Lacey says. ‘Both of you. I’ll get Kate and be right there.”
I spent an hour in my office crashing out, reminding myself I couldn’t call Glenn to congratulate him and then shovel this new problem onto his doorstep.
So I waited for the rest of his team to arrive, and walked over to their pod to casually let them know they’d be having dinner with me and Edmund tonight.
I thought maybe they’d take it in stride and prove to me that it was nothing to be concerned about.
This is distinctly not the case.
“I’m supposed to go to the game tonight, bro,” Trevor is telling me. I’m debating just letting him go, unsure what a conversation between him and Edmund would be like.
“The fuck you are,” Kate tells him, sitting down. “You’re coming to dinner and you’re going to speak like the educated adult you are.”
Trevor blinks but doesn’t disagree.
Lacey snorts from the whiteboard, where she’s drawn a three-column table in the corner. The headings of which are +, ?, and -. I’m about to ask what she’s doing when she writes Trevor’s name down in the ? column. I’m assuming this isn’t about attendance.
“Kate, you’re good, I’m good. Jude, I’m putting you as good because you kind of better be.”
“Can we get Amber?” Trevor asks. “She’s smart.”
“I already messaged her, she’s going to do her best to make it.” I say.
“What about Rob in sales?” Kate asks. “He has an MBA.”
“MBAs are a waste of money,” Trevor tells her. “You learn more in one month of starting an actual business than in two years of business school.”
“Someone’s defensive,” Kate says under her breath.
“You’re going to join Trevor in the questionable column, Kate, if you can’t stop sniping at him.” Lacey says, adding Rob to the ? list.
She raises her marker to the - column and looks at me.
“I know who you’re going to put there,” I say.
“Do you disagree?” she asks me.
“Who are we talking about?” Kate whispers to Trevor.
“Keith. Our CTO is a dumbass,” Trevor whispers back.
I can’t deal with this right now. Give me a time machine dialed back half a year and sure, I’d hire someone better.
At the time, Edmund was pressuring me to bring on a CTO, and what I liked about Keith—that no one else seems to appreciate—is that I knew he wouldn’t fight me on anything.
The trouble is, he doesn’t fight the engineers on anything, either. Because he might be a dumbass.
“What if we don’t tell him there’s a dinner?” Lacey suggests.
“Or—hear me out,” Trevor says. “We bring Dave, but we gaslight Edmund by just insisting that he’s Keith.”
They all start laughing and I would too, except for the part where I start to see Edmund’s point about my leadership.
“I promise you two things,” I tell the team. “One, Keith will be fine. He’s at least clever enough to talk like a CTO. Remember, Glenn didn’t hate him at first. And two, if we survive the next month, I’ll bring in a proper CTO. I mean it.”
And I do. First I go check in with Rob, and discover he likes to talk about sports too much. Edmund only likes golf, and Rob’s entire personality outside of sales is college football. He’s not going to do us any favors. I mentally demote him from the ? list.
I spend an hour coaching Keith on the vision, the tech, and why he believes in this as the future of Lettercat.
He might be a man out of his depth, but he’s a survivor.
He certainly won’t wow anyone, but the bar for personality is basically on the floor when it comes to CTOs.
After I decide he’s ready, I set a reminder for myself to check in with Keith after the next board meeting.
Whether Lettercat survives or not, I owe the team something better.
I spend so much time on the business side of things that when Lacey pops into my office two hours before our dinner reservation, I don’t tell her we’ll be in beta next week. Because we won’t be. Instead I ask her if she thinks adding two contractors to the team would be at all worthwhile.
She sits down on my couch.
“We’ll figure that out tomorrow,” she says. “I want to hear your strategy for tonight.”
I confess that I don’t really have one outside of my usual, which is Try Not To Piss Off Edmund.
“I’m not claiming to be an expert in this—I’m not even done with the book Glenn recommended about it.
But it’s called managing up; basically using empathy to improve your relationship with your boss.
Just like when you talk about framing the Lettercat story for the board.
Only it’s your story, and it’s for the person who manages you. ”
I sit on the other end of the couch and listen while she tells me how I might adjust my communication style and method to suit the people in charge of me, how it’s especially helpful when they’re difficult.
I need to be better at anticipating what Edmund wants from me and offering it to him before he even asks.
We go through all the things we think Edmund is looking to see from me tonight, and what I can do to reinforce that I have them. It requires a shift in my thinking, but I’m happy to do it. Whatever I’ve been doing hasn’t been working.
“Thank you,” I tell her. “I mean it. It makes a lot of sense.”
She nods and gets up, smooths her skirt. “You’re going to do great tonight. Don’t stress.”
She might say this last part because my head is in my hands.
“Lacey,” I say, looking up as she leaves. She turns around in the doorway.
“Did Glenn recommend that book to help you deal with me?”
She looks like she’s about to crack a joke until she sees how serious I am.
“Yes,” she admits. “But not because you’re a tyrant, Jude. I just never tried to see things from your point of view.”
I think about what I heard her saying on the elevator that day, but decide to let it be.
“Before I go, one more bit of unsolicited advice,” she says.
“Anything. I’ll take all of it,” I tell her.
“This one’s more of a question: do you have any shirts that don’t say ‘Lettercat’ on them?”