Chapter Six
JUDE
Friday was all about ideas.
Saturday we’re crunching the numbers.
Sunday, everything goes into the board deck.
I wouldn’t say I’m used to this pace, but I’ve been operating in it on and off for four years now.
Tight deadlines, high tension. Pressure to deliver.
When I was in school, I used to claim this was when I did my best work, but out in the real world I know that’s not true.
Sleep is vital, fresh air is important, good nutrition is, too.
I look over at Lacey to see how she’s holding up. She’s wearing her blue light blocking glasses and chewing angrily on a gummy peach, like she’s about to kick her laptop’s ass, and my only thought is that I’d rather her anger be directed toward an inanimate object than toward me.
“Fighting with Excel again?” I ask.
“It’s so fucking stupid,” she says. “There’s no reason it won’t work.”
I’m sure there is, but if my last thirty hours spent mostly in her company have taught me anything, it’s that disagreeing with Lacey is more trouble than it’s ever worth. She takes everything so personally.
“How about you put your screen up and let me take a look?”
She sighs and screencasts, showing me where she’s seeing a series of hash marks instead of the numbers she’s expecting.
“Can I give you a suggestion? Edmund humiliated me over this a few times, so I learned it the hard way. It’s okay to copy a formula from one cell to another, but you should never reference a formula that’s in another cell.”
“Why not? It’s efficient.”
She’s belligerent even when I’m trying so hard, when I’m going out of my way and using three times the number of words than I would normally. I give up; if she’s going to be mad anyway, I might as well be blunt.
“It makes it impossible to find and fix your errors.”
I choose to assume the exasperated sigh is directed at Microsoft, not me, and watch her pull apart her formula full of referenced formulas.
“Sorry that I’m being a baby about this,” she says without looking up. “I vastly prefer product development to spreadsheet bullshit.”
“You and me both,” I tell her.
“Ugh. There it is,” she says as the first cell of hash marks is replaced by a number.
“I believe ‘whoomp’ is the correct phrasing,” I tell her. She shakes her head. Not funny.
“But I had this Executive Assessment done, and it said I come off as humorless.”
“It’s better if you don’t try,” she says. With a smile, though.
I wait for her to finish reassembling her formulas, and when she’s satisfied with it, I send her a DoorDash link so she can add her sushi to the dinner order. Then I propose we walk to go pick it up.
“I need to see something that isn’t the inside of this office,” I tell her while she orders. “And while we walk, we can figure out the framing of the story for the deck. That’s just as important as the numbers. Maybe even more important.”
“I’m down for a walk,” she says, getting up. “Are you about to tell me about how Steve Jobs took most of his meetings while walking?”
“No,” I lie. “But you read the Isaacson biography?”
“It’s not about product management, but it’s the most important product management book I’ve ever read,” she says.
I don’t tell her that I see it the same way, but for starting and running a company.
She follows me out of the conference room, waits while I grab my sneakers from my office, and instead of figuring out the framing for my presentation, we talk about our favorite parts of the Jobs book as we walk to get the sushi.
We both want to go to Japan, we both think it’s deeply strange that he ate mostly fruit for so much of his life.
“How about how emotional he was?” she asks me.
“What about it?”
“Just that you don’t really seem, I don’t know. Tapped into that, at least work-wise.”
“I guess I don’t really consider that one of his strengths.”
She raises her eyebrows. “Noted,” she says.
“Ah! Hello, Mountain Carrot,” the woman at Gochiso says when she sees me.
“It’s my favorite roll,” I explain to Lacey. “I come here a lot.”
“He does,” the lady says. “Always for one, though. It’s why I didn’t recognize your order tonight.”
She hands me the bags and wiggles her eyebrows at us. I debate if I should introduce Lacey as my coworker to this person I see at least once a week and haven’t learned the name of, but instead I thank her and pretend she wasn’t insinuating anything. A mistake, it turns out.
“You two should eat here next time,” she calls out to us as we leave. “Date night, Mountain Carrot! It’s more romantic than Netflix and chill!”
I make an involuntary strangling sound and feel my face burning. Lacey, holding the door for me, starts laughing and can’t stop for about half a block.
“I’m sorry,” she says, catching her breath.
“Don’t be,” I tell her. “I’d be laughing too.”
“Except you’re humorless,” she says, with fake concern, like it’s a medical diagnosis. “So young to have such a large stick up your—”
“You know, it’s actually a mountain carrot,” I interrupt to tell her, which sets her off again. We’re almost back at the office before I remember we were supposed to be discussing strategy.
One thing Lacey was right about: it’s going to be a lot of work. But the numbers look fantastic.
“If we can pull this off,” I begin, popping a piece of sushi in my mouth before I can finish my sentence.
She waits while I chew, and something in her face is hesitant.
I think about what I was going to say: that Edmund will be so pumped, that getting funding will be a walk in the park, that we might even add some new investors.
All of these things I’ve grown to think were important to me.
“If we can pull this off,” I say, once my mouth is empty, “Lettercat’s going to be so much more than I ever imagined it would be. People will run entire small businesses from our platform.”
She smiles at me, a genuine smile. “Yeah,” she says. “It’s a total game changer.”
And then it’s Monday morning.
The deck is done, the numbers are solid. My talk track is clear and confident, according to Lacey. I ran through it three times last night, twice with founder friends on a Zoom and once with her and Glenn.
“I don’t have a lot of notes,” Glenn told me. “But if I had my camera on, you’d see how proud I am of you, both of you. Jude, I know you’re my boss, but it’s true. This is great stuff.”
Lacey and I stumbled out of the office at eight o’clock Sunday night, and fewer than twelve hours later I’m back there, getting ready for showtime. Jonnie has texted me three times about the pastries and coffee we’re having brought in. Edmund has confirmed he will arrive at eight forty-five.
In the lobby, I take my pause to feel the gratitude and hope like hell I’m not wrong about any of this.
But even if I crash and burn today, I’ll do it over something I believe in.
That feels nice for a change. Rounding the corner, I expect to turn the lights on, but they’re already humming.
I walk into the pods and find no one sitting there.
I turn back and see Lacey at the end of the hallway, coming out of the kitchen with a coffee. She pauses in the doorway.
I come closer.
“Hey,” she says. “Good morning.”
“Kind of early for you,” I remark, checking my watch.
“Yeah, well, I forgot I don’t live here.”
“I’d like your expense report more if you did. Fewer Ubers.”
She smiles. “You shaved.”
I nod and run my knuckles across my now-smooth jaw. “Yeah, but I probably should have found an emergency haircut,” I tell her. She looks at the pile of hair on my head and twists her mouth to the side.
“Follow me,” she says, heading over to where the sales team sits. I watch her open all the desk drawers in their pod until she stops and pulls something out. She holds up a tube. I’m so glad it’s not a pair of scissors.
“Product,” she explains, squirting some of it into my palm. “I knew these guys would have some.”
“I don’t want to look like I escaped from American Psycho,” I tell her.
“Just go like this,” she says, lightly pushing the hair off her forehead and back at the sides. I do the same, and after a couple of passes she nods her approval.
“It looks nice,” she tells me. “You’re going to kill it.”
“Last chance for you to join me,” I offer. “Sell the vision, hit ‘em with all those stats in your head. They’ll love you in there.”
“Not on your life,” she laughs. “I’ve done enough for you, Jude Mulholland.”
I’m about to tell her she’s more than right, but I hear Jonnie in the hallway, shouting about pastries. I’d better go to her rescue.
Sometimes when I speak with other founders, they talk about their board and use words like guidance and support. They tell stories where their board operates like a team of Avengers called upon to use their business superpowers to save the founder’s ass over and over.
That’s not my board of directors.
It could be my leadership style, or the type of business we have, or the numbers we’re doing. Nope. It’s not any of those things that make it tense, that make every board interaction feel like I’m walking a tightrope in high winds over broken glass and alligators.
It’s Edmund.
I’ve got at least four inches on him, but I bet if you asked people who know us both, they’d think he’s taller.
The most imposing man to ever wear pleated pants and a V-neck sweater, no one will take a seat until he sits down.
Once he does, he’ll direct three or four people on where they should sit.
These are people who have run huge companies, who deploy billions of dollars in investments, but they stand here with me or cower at the corners of the room, waiting for Edmund to suggest they might like to sit next to him.
For me, he points to the seat opposite him, in the middle of the table. I expected this; when he and I are in alignment, he’ll seat me next to him, but when we’re hashing something out, he positions me physically as opposed to him.
I sit across from him, plug my computer in. Glenn’s here, but at the far end of the table. My CTO and part-time CFO have chairs at the back of the room. After some brief opening remarks, Edmund turns it over to me.
“It’s your show,” he says. “Run it.”
I don’t need to fake confidence and enthusiasm today; I’ve got it. It was a brutally long weekend, but this is a plan I believe in. There’s a bright future for Lettercat. I smile like a winner and begin.
There is no applause when I’m done, not that I was expecting any.
It’s oddly silent in the room, and it’s because the entire board is deferring their judgment until Edmund states his.
Be enthusiastic when he’s reticent, and you’re exposed for missing a huge gap.
Poke at a plan he thinks is amazing and you’ve shown you lack the ability to recognize innovation.
They’re a bunch of playground cowards, basically, and Edmund is the bully they’re all afraid of.
He asked only a few questions during the presentation.
He’s now poring over his printout of the deck, reading glasses on, reviewing the numbers.
This is where he shows you why he’s Chairman—the guy can look at the most complicated spreadsheet imaginable and spot a miscalculation, an overestimate, an implausible numerical assumption in an instant. It’s terrible.
“Do you know what I liked about the other plan?” he asks me, peering over the top of his reading glasses.
“It scaled faster,” I say.
He nods. “And more predictably.”
“But it was dependent on relationships. For this we’re building real technology. It’s harder to copy.”
“Throw enough money at anything, and it’s easily copied,” he says, flipping through his printout. A couple years ago I might have offered a counterpoint, but I’ve learned when to keep my mouth shut.
He asks a few board members their opinion. They equivocate; he rolls his eyes.
“You’ve got a mixed bag here,” he tells me finally. “It’s a gamble. But I don’t shy away from making bets.”
I nod like I understand and wonder if he’s intentionally confusing. Everything is a riddle; everything might be chess.
The glasses come off. “What I don’t like is the timeline. And I don’t know your team has proven they can execute on this level.”
“I’m confident that they can,” I say. I follow his gaze to my CTO, who is covertly scrolling social media in the corner.
“I’m sure you are, so I’ll give you a chance to prove it. You get one month. Show me that you can deliver the first phase of this and you get my blessing for the rest. Hell, you’ll get my money for it.”
The rest of the board nods and murmurs in approval. No one appears to notice how insane it is to ask that we do an entire quarter of software development in one month. Or they do, but no one’s going to stick their neck out to say it.
When they all file out for lunch, Edmund asks me to stay back.
“I want to talk about the flip side of this,” he says. “You nail it, and you get everything. But I’ve heard of some acquisition interest, Jude. If your team doesn’t deliver, it might be time to cash it in.”
I nod, I swallow, I make mealy-mouthed pledges that I’m sure it won’t come to that.
We stand up and walk out of the room together. I see Lacey loitering near Jonnie’s desk, trying to catch my eye.
“How did it go?” she mouths.
There’s worry in her face and no way for me to give context, so I nod and give her a discreet thumbs up, which I immediately regret. It feels dishonest; the news was not that good. It was actually pretty horrible.
I decide to focus on the project itself instead of the looming threats. I’m not going to sit on the sidelines while my whole company is at stake, so forget the spreadsheets: I’ll join the team and do some real work. Just the idea of it is energizing, as long as I don’t overthink it.
Is Edmund really this unreasonable, or is he setting me up to fail?
One month until we all find out.