Chapter Five
LACEY
Because part of my job is to listen to and accept the truths in other people’s points of view, I suppose I didn’t have to start off on such a harsh note.
What I was aiming for, when I think about it, was that same blunt affect Jude uses, the one where his delivery is so flat that it seems like he’s “just asking,” and you don’t realize that he’s stabbed you in the heart until you look down and see the blood.
I’ve seen him do it to Kate about customer satisfaction scores, to Dave about architecture decisions.
We get it, you’re smart. Do you really need to make us look stupid to prove it?
It’s immediately clear that I missed the mark. I see him startle at my opening line, and I wish I could soften it. Though I stand by my point; he wasn’t interested in hearing me out until he was stranded, paddle-less, on Let’s Move Upmarket Island. Instead of apologizing, I get right into it.
I start off with the data, qualitative first. Feedback survey responses, quotes from support tickets, win/loss data from the sales team, all of it showing that our customers are frustrated creators who want to spend their time creating.
They don’t want to have one system for their newsletter, another for their marketing, yet another for their website. Jude nods along. At least he’s engaged.
Then I shift into numbers that show the same thing.
We lose lots of customers not to a true competitor, but to their existing website and email marketing services.
Expanding our offering to include those things would reduce customer churn, and selling it as a premium package would give us a revenue lift.
Before I move to the last slide, I check in with the box on my screen that contains Jude’s face.
He’s not exactly beaming, but he looks less angry than he did when I began.
I see him lean in when I move to the last slide, the one with the revenue projections based on presumed adoption and upsell.
His eyes go to the bottom row, where I’ve highlighted the annual recurring revenue and the return on investment. He sighs. Leans back.
He looks disappointed.
Glenn’s voice crackles through.
“Sorry to chime in from the train,” he says. “But I do think there’s something here.”
“There is,” Jude agrees. “There’s just not enough of it.”
“Lacey’s been a bit conservative with her projections,” Glenn offers.
“He thinks we should price it higher,” I finish for him.
“Do you think that?” Jude asks me.
Here it is, the trap.
“No. Just because you can do something, doesn’t mean you should. We have loyal customers who love our service. They don’t just subscribe; they advocate. So sure, we can squeeze a few more dollars out of them each month, but we’re also changing how they feel about us in the process.”
I watch Jude consider this as Glenn pipes in.
“A reminder for Lacey that we are running a business here.”
I smile. Glenn’s always telling me he can’t wait to see what I can do once I lose my ideals and ethics. The thing is, he’s kidding when he says it.
But Jude looks at me through the screen.
“Our goal here is to make money, not to make people happy,” he tells me.
It surprises me how much it stings to hear him say those words.
Despite the paycheck and the stock options that I happily accept, what he just said is so far from my perception of Lettercat and what it’s all about.
I don’t like him personally, but I guess considered the company itself to be proof that he was different from the rest of the tech bros, that he cared about something more than valuations and IPOs. I guess I was wrong.
“What makes Lettercat special is that we do both,” I say indignantly, perhaps a little angrily. I regret it instantly. He’s the founder; it’s quite literally his company. I don’t get to tell him what it is or is not.
“Can you guys hang on a second?” Jude asks, and his screen goes black.
I wince into my camera. I can’t see him, but I know Glenn is shaking his head at me somewhere in a tunnel under San Francisco.
“Some coaching for you during this intermission,” he says. “Lacey, you’re great at listening to our customers. But when you’re in product, everyone is your customer, not just the ones who get billed. Jude is also your customer.”
During summers in college, I worked for my mom’s friend, a wedding planner.
I’ve dealt with difficult customers, just not always well.
I decide to channel Kate, who has vast reserves of patience when she’s on calls with impossible customers, honey-voiced and sweet until she’s confirmed the call has ended and adds, “you stupid, condescending motherfucker.”
“I’ll be more collaborative,” I promise.
“It’s called managing upward,” he tells me. “Book recommendation landing in your inbox shortly.”
Jude reappears after a couple of minutes. I guess when you’re in charge, you can just do things like this. To his credit, he’s a lot nicer when he comes back. But no one ever said the man is an idiot; of course he’s going to be kind to me when he wants something.
“Okay,” he says. “Let’s do it.”
“Excuse me?” I ask.
“Let’s do your idea. But we need to go bigger than what you’ve laid out today.”
“Bigger how?”
“That’s what we’re going to spend the next three days figuring out,” he declares.
Glenn cuts in to say he can check in throughout the weekend, but he absolutely cannot be physically present.
“No, no,” Jude says. “I get it, your family comes first right now. I meant Lacey and me.”
He pauses and pushes back the swoop of hair that keeps settling on his forehead. He looks right into the camera at me.
“If you’re willing, I mean. I’d like to get started today.”
There’s something plaintive in his voice, something pleading in those soft brown eyes. He’s like a Labrador who wants my cheeseburger.
“Fine,” I say. “I’ll be there in thirty minutes. And I’m expensing everything.”
“He’s waiting for you in Gutenberg,” Jonnie tells me when I arrive, referring to the large conference room.
I’m relieved we’re not in his office, or in Stanhope.
It’s going to be a lot of togetherness already; closer quarters are unnecessary.
She takes my lunch order before letting me go any further.
Jude has already claimed one side of the conference room table.
His laptop is connected to the big screen at one end, and the whiteboard has been rolled over to the other.
On my side of the table is a fresh notebook, three sharp pencils, charging cables for my phone and laptop, a bag of gummy peach rings, a Dr Pepper, and a box of the sourdough pretzels I like to gnaw on while I’m thinking.
I see Jude watching me as I take inventory of all my favorite things.
“Your team knows a lot about you,” he says, explaining.
“I guess they do.” I sit down in front of them and unpack my bag. I can tell he’s waiting, so I might take a little more time than I need to. I open the pretzels and pop one in my mouth..
“Do you need a minute?” he asks, and I shake my head. He gets up and goes to the whiteboard and grabs a marker. “So first of all, thank you. For your vision and ideas, but also for pitching in like this when we’re under the gun. It’s very much appreciated. By me. I appreciate it.”
It’s awkward but sincere, and makes me think Glenn has given him some coaching as well. I nod and tell him I’m glad for the opportunity, which is something you say when you’re managing up. I learned this from a quick google on my way in.
He then tells me about the list of other verticals he’s been working on, how he’s wondering if there’s another market segment adjacent to publishing that we might move into, like maybe education or automotive.
“You mean Trevor’s idea,” I say. “You want to do Trevor’s idea but for mechanics?”
“I was just exploring it,” he said. “Taking a top-down approach.”
I attempt to smooth my forehead and my voice and my entire demeanor. “I’m sorry. I thought I came in today because you were interested in my idea. The one where Lettercat becomes the home of their website and email marketing, not just their newsletter.”
“Yeah,” he says. “Sorry, just wanted to see if there was anything in that other idea.”
I look through my bangs at him and I say nothing.
“So how about we start by just brainstorming,” he says, uncapping the marker and writing LETTERCAT EXPANDED SERVICE IDEAS across the top of the whiteboard.
His handwriting is surprisingly neat. But then I sit there for maybe four or five minutes while he writes his ideas down in a list on the board, all of them about taking over billing and infrastructure for people who never asked us to do that.
I get up and leave the room, and when I return with a stack of Post-it pads and two Sharpies, I don’t think he even noticed that I was gone.
“Jude?” I say. He looks up.
I hand him a sticky-note pad and a Sharpie, explaining how my first Product boss was proudly old school and analog.
We always started off brainstorming by sticky-note, everyone smacking their ideas up on the wall until we ran out, then moving them into categories, then priorities, putting all the goofy ones off to the side until we discovered the core set of features.
“Outcomes,” Jude says. “Not features. We need to think in terms of outcomes and value.”
“Sure,” I tell him, or the business consultant worm that’s currently chomping on his brain. Actual humans don’t speak like that. “Just say your outcome when you put it up. That way our ideas feed off each other.”
It’s rough going at first. I wonder when Jude last worked with anyone, as opposed to calling all the shots.
He persists in adding things like Inventory Management while my Post-its say Contact Us Form.
His ideas refuse to acknowledge mine, and they’re too large and weird for the company and team we are.
“Can’t you think a little bigger?” he asks me when I announce the arrival of Calendar of Events on the board. “And is a ‘calendar’ an outcome?”
“Oh, because ‘International Storefront’ is?”
Jude sits down and puts his head in his hands. I suppose this is better than yelling at me. Unless it’s not.
I disconnect his computer, broadcast my laptop to the screen, and I just start talking.
I show him the newsletters of three of our most loyal and successful clients: a writer, an educator, a chef.
They’ve all built huge followings on Lettercat.
But their websites all look like they were designed in the 1800s.
They’re cobbling together seven different technologies to run their businesses, and if someone else figures out how to make it easier before we do, they’re going to eat our lunch.
“Can you go back a screen?” Jude asks me, and I have a flashback to yesterday. Is this where he makes me find the hole in my own idea?
I click the back button. The screen fills with the web version of our chef’s latest newsletter.
She’s written up a panzanella recipe and has photos of each step and an embedded YouTube video.
I study it, not looking at the delicious salad, but trying to figure out what Jude’s about to have me walk him through.
The trip into the woods with a shovel, where he’ll make me dig my own grave.
Instead, he stands up and removes all the sticky notes from the board, one by one. When he has them all in one stuck-together pile, he drops them into the recycling bin and sits back down.
“Clean slate,” he says. “Is there a possibility that we’re both approaching this incorrectly?”
Fitting that Jude can only admit he might be wrong while lumping me in there, too. But I kind of see his point.
“First principles,” I say. This is where you throw out every single assumption you’re making. It helps you correct the bias you bring along with your perspective. “You’re a creator but you’re also a small business. What helps you succeed?”
Then he uncaps his Sharpie and writes on his pad, stands up and slaps it on the board.
“Podcast platform,” he says.
I look back to the newsletter. Our chef is a hustler, and she’s got a footer full of links to different places, including her own podcast. Another place for her to log in, another system for her to manage.
It’s true to my idea, only it’s bigger. And it’s something that would be very useful to our customers.
Alright. I can do this kind of bigger.
I scribble one of my own. “Merch store.” Smack.
“Booking platform.”
“Premium content for paying subscribers.”
“Live video streaming.”
“Asian salad with tofu. Harvest salad with chicken.”
Jonnie is here with our lunch order.
“When do we stop?” Jude asks me, deep into his second pad of sticky notes. It’s getting dark outside, but I’ve had a lot of Dr Pepper. I’ll be up all night anyway, might as well be here.
“When the ideas get bad,” I tell him through the pretzel in my teeth.
“I think that was ten ideas ago for me,” he says, crumpling the sticky note in his hand into a ball. He tosses it into the recycling bin and pumps his fist when he makes the shot. Nerd.
I look down at my pad, where I’ve written “ads on buses” and decide it’s time for me to retire my Sharpie, too.
Jude approaches the note-laden board and surveys it, then starts moving ideas around, migrating the best ones to the top.
I join him and do the same, while sinking the implausible or out-of-scope items down to the bottom corner.
We work silently, aware of each other but sharing the space.
A few times he rescues ideas I’ve discarded, pulling them back up and back into consideration.
I split the top ideas into two tiers: tier one is reasonable for a first launch, tier two is not.
He moves most of tier two back into tier one.
“There’s no way we can get that done with this team,” I tell him, moving one of them back down.
“Then we grow the team. Or we integrate. Or partner.”
“It feels like too much.” I cross my arms, looking at the massive scope before us.
He pauses mid-shuffle to look over his shoulder at me.
“Yeah? Tell me about all the people who find huge success by doing just enough, Lacey. Show me where they are.”
I move the Post-it back to where he had it.
“I need a break,” I say, and I go sit in the stairwell and call my mom. But I don’t cry.
I got too comfortable during the brainstorming session, and I forgot I wasn’t dealing with Glenn or my team. Jude always finds a way to remind me that he’s not a person I work with; he’s a person I work for.
I feel like the guy from that Instagram video, who’s showing the stitches he needed after his pet raccoon attacked him. He’s very sad and looking for sympathy, but when I watched it, all I could think was: what were you expecting when you let a raccoon live in your house?