Chapter Four
JUDE
After one of the least-bad meetings I’ve ever had with Edmund, I was able to leave the office before ten last night.
I went straight to the gym around the corner — leg day is still leg day — and once I was through with my workout, I checked my phone.
Some friends were meeting up in the Mission, and since I’d given a noncommittal reply, they were texting me updates about what bar, where the table was, what the scene was like.
But it never matters where they are or what they’re doing, it’s always the same.
This friend group is all current founders, former founders, or wannabe founders, which means all they talk about is funding rounds, valuations, share classes, board drama, and product-market fit.
I’m part of the problem, I’m aware. I started hanging out with these guys more after I noticed my college friends, who have lives, would get this glazed-eye look whenever I was talking. Because what I talk about and think about is my startup.
But there are times when even I am not in the mood for stressing or spiraling about business and I wish we talked about baseball or girl troubles or travel plans. Since none of us do anything other than work, there are no games or trips or girls to discuss.
I decided to skip, and instead rode my motorcycle five whole blocks to my apartment where I DoorDashed some saag paneer and found a beer in my fridge. I ate while working on my board deck.
With Edmund’s approval, I was gearing up to present Trevor’s plan as Lettercat’s big swing in Monday’s board meeting.
The trick, I learned after Edmund embarrassed me repeatedly in front of the entire board, was to get his buy-in before the meeting even starts.
No surprises, no hard questions under pressure.
With Edmund such a tireless alpha, having him in my corner at the outset means everyone else will just go along with the plan.
And the plan was to get the board to approve our new direction so we could lock down another round of funding so we could make it a reality, adding thirty-six months of runway at our projected burn rate. That would translate to me breathing a little easier for maybe twenty-four months.
Even the prospect of that was enough to allow me the most decent night of sleep I’ve had in weeks.
I wake up feeling not necessarily refreshed, but less doomed than usual.
I know I’m not in the clear yet; I’ve simply learned to embrace any calm I can find before the next inevitable shitstorm, which is always closer than I think.
While I wait for my Dasher to bring a coffee and egg-and-cheese wrap, I unpack the clean laundry that was delivered yesterday.
One stack of jeans and three stacks of Lettercat tees go into the closet.
I know it’s a cliché to be a founder with a uniform, but it really frees up significant mental space when you don’t have to think about what you’re going to wear each day.
And I figure if even one person a month sees my company shirt and is inspired to sign up, that’s money in the bank.
I’m filling up my sock drawer with twenty-four copies of the same gray sock— I never need to find a match —when my phone buzzes. I pick it up to check where my coffee’s at and instead see a call coming in from Edmund. It’s pretty early, even for him. I brace myself and answer.
“Well, I’m sure you’ve seen it and you’re pivoting,” he says.
I swallow hard and lie my face off. “Yes, sir. You know it.”
“Do you want to discuss how your entire strategy for next quarter was front-run by your competitor right now, or would you prefer to wait until after you’ve sold me on your other plan?”
“After,” I croak. My whole professional life flashes before my eyes, and it is not impressive.
“I’m playing Torrey Pines with Wally today, then taking the wife to Santa Barbara for the weekend,” Edmund tells me as I open my laptop and frantically try to figure out what the fuck he’s talking about.
“That sounds nice,” I say, my face burning.
“For me, yes, it is. But for you, it means no babysitting. You need to come to the board meeting on Monday and wow us all with whatever this other plan is. ”
What other plan? I’m thinking.
“Not a problem,” I say, like a good and respectful foot soldier. “I look forward to sharing it.”
While he’s outlining all the reports he’s going to want on Monday, I open Slack and see Tooity’s LinkedIn post shared in the competitive analysis channel.
I watch it with the volume off and my adrenaline spikes, my stomach churns.
I hit my phone’s mute button to keep Edmund from hearing if I throw up.
“Jude,” he says in parting. “You’re running low on money, but also on my faith. I’ll let you decide which is worse.”
“Yes, sir,” I say, and then realize I’m still on mute and he’s already hung up.
I sink to the floor in front of my laptop, in my rented apartment full of rented furniture, and think about how easy it would be to just leave it all behind. I could go home to Michigan, maybe go to law school. Make all of this a footnote in the rest of my story.
Except for those eighteen people on the payroll. I owe them more than that.
Well, at least seventeen of them. I’ve got some words for Trevor.
While I call Trev repeatedly, my coffee and wrap arrive.
I leave them on the counter to get cold, because I have no appetite and all that adrenaline is better fuel than caffeine could ever be.
My five calls go straight to voicemail. I text him a full paragraph outlining the situation and he replies promptly: Bro that sucks
This isn’t what I’m looking for. I wait for him to send a message telling me he has a backup that might be even better.
Or at least a message telling me he’s on it, we’ve got this.
Nothing comes. I write an entire paragraph about how we need to understand—by Monday —if there’s anything salvageable in that plan.
Either that or pull an entirely new strategy out of our asses.
Super sucks man. PTO today! In an Uber right now. SFO —> LAX for a long weekend
I throw my phone on the couch, hard. Trevor is a great friend and a pretty good employee. He cares about the company, but only when he’s logged in. And no, it’s not okay to say that’s what he gets paid for; he has equity in the company. Equity is supposed to make you care.
I message Glenn, even though he likes to stay offline until his kids are out the door. I usually respect his boundaries, but I’m spiraling here.
He doesn’t respond directly. Instead, he sends me a meeting invitation for a session called Lettercat Next Phase Strategy that will begin at 9 a.m. In the notes he says to start without him, as he’ll likely be a few minutes late.
Also invited are Trevor and Lacey. I know Trevor’s got nothing, but I forgot how Glenn had urged me to hear Lacy out.
I try to remember what he told me about her idea, but I come up with nothing. All I know about Lacey Lang is that she hates me, she’s too immature to handle feedback that isn’t praise, and that she is currently my only hope.
I shower, but I don’t take the time to shave. Again. I throw on my personal uniform and head out the door, skipping the motorcycle. On a good day I’m terrified I’m going to dump it in the road, and this is no good day. I take an Uber instead, annoying my driver.
“Five blocks, man? You better tip me!” he shouts when I get out. I tip him.
Normally, I like to pause for a second when I walk into the office and see the neon sign with the Lettercat logo my sister made.
I try to take a moment to recognize that no matter what happens that day, I’ve built something real, something to be proud of and grateful for.
I don’t do that today. I can’t be thinking about how far I’ve come when I need to make sure this isn’t the end of the road.
The office is dark; no one’s here yet. I turn the lights on and watch all the desks and conference rooms light up under the open-duct, industrial ceiling. It looks like a startup in here, even if it feels like a mess.
I’m glad to be the only person in; it means I have some time before I need to pretend everything is fine.
Lots of Lettercatters will read the news today and wonder what it means for us, and while our list of core values includes Transparency and Honesty, I’ve learned that telling folks that you’re going to run out of cash in six months doesn’t do much for morale.
Glenn and the Amber, the part-time CFO, are the only ones who know the whole story.
I plan to keep it that way until I know the ship is sinking.
Edmund’s always talking to me about his Viking-ass version of leadership and I nod along, but to me, a real leader takes all the blows so their team can focus on what they do best. That’s what I try to do, at least. Today I could use a little help, or maybe divine intervention. Either or.
I kick my shoes into the corner and turn on my computer.
By now the full joint press release is out.
Corday Ford and Tooity are partnering to combine the CF portfolio with the Tooity platform to create the future of online publishing, blah blah blah.
They’ll start with the purely digital publications, then move to the print versions, and finally provide all Corday Ford authors a Tooity community newsletter. Great.
I check Trevor’s deck and find that CF’s three largest competitors combined have a lower market share than they do.
Hindsight being what it is, I see how this strategy is more than a little risky, especially considering the plundering manner in which Corday Ford operates.
They’ll either bankrupt or acquire Tooity within a year, and it’s hard to say which one is better for the founders.
Sure, it might be a lie I’m telling myself, but it’s the story I’m going to go with today.
“Dodged a bullet,” is better framing than “all is lost.” I roll my whiteboard over and angle it so anyone who walks in can’t see that I’m literally starting from square one as I brainstorm things we can build.
Edmund’s voice in my head takes over: where is there a large, underserved market that Lettercat can disrupt?
Enterprise level, small business verticals, the public sector.
I write until my arm is sore, waiting for a lighting bolt that never comes.
And then it’s 8:58. People are starting to drift in.
Glenn’s meeting is virtual, so I’ll take it in my office even if Lacey’s here. I log in but turn my audio and video off, then pop out to the kitchen to get a water and see if all the good fruit has been stuffed in people’s work bags and brought home. I know they do this, I’ve seen it happen.
When I get back to my office with a sad banana and some ice water, Lacey’s just logging in.
She’s working from home, but where she lives could be a Zoom background.
Better than that: it has personality, unlike my apartment.
I consider adding this as a to-do for myself, but writing get personality on my Notion board only seems sad.
“Hello?” she says, but I’m on mute and my hands are still full.
As I go to unmute myself, I see her study herself on camera.
She fluffs her hair up in front. and tucks some of it behind her right ear.
From this close, I notice she has a sprinkle of freckles on each cheek, and that her eyes aren’t brown like I thought they were: they’re hazel.
I should turn my camera on and say hello, but instead I watch her rummage in a bag she’s holding and pull out a lipstick.
It’s bright red. She leans in close to her camera and applies it, tracing the M of her top lip slowly, then a quick stroke along her lower lip before she settles back, smacks her lips together and surveys her work.
I know it’s only a screen, but her face just feels so close to mine.
I’m holding my breath, fully a creeper behind a two-way mirror, and I don’t know how to make it stop. Oh god. Camera first, or mic?
I unmute.
“Hey,” I say. “Sorry, just getting back from the kitchen.” I turn on my camera and show her my water glass and banana, completely unnecessary evidence.
“Good morning,” she says.
I catch a glimpse of myself onscreen and it’s not good.
Has my left eye always been so much larger than my right?
And the hair. I missed an appointment two weeks ago and still haven’t rescheduled.
I grab a Lettercat baseball hat off my desk and put it on, see that it somehow makes it all worse, and take it off again.
“I’m not sure if you saw the news,” I say as a way of opening, and she nods. This is going to be fine. She’s here, at least, which is more than I can say for Trevor.
“I did. I guess that’s why you have time for my ideas now,” she tells me.
Okay. So it’s going to be like that.