Page 11 of The Hard Launch

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.