The founder who interviewed a hundred people before she built anything
She lost her father, then built the company she wishes she'd had.
Emily Kyle spent over six years at GitLab, joining when it was around twelve people and staying through its IPO, then ran marketing as employee number four at one of its incubator projects. After her father died suddenly of a heart attack, she went back for an executive MBA and started Good Grief, a company built to handle the brutal administrative aftermath of losing someone. She is about a year in, bootstrapped, and building it with a co-founder.
Here are the five ideas I keep coming back to from our conversation
1. Fall in love with the problem first.
Emily had already pitched a solution in an MBA class before she had a company. The first thing she did once she went all in was refuse to defend it. “I didn’t want to get married to my solution,” she told me, “because people do that all the time. They’re like, this is my solution, why don’t you love my solution?” She read the book Fall in Love with the Problem, from the founder of Waze, then went and interviewed over a hundred people in the space before committing to a fix. She came in, in her words, as “a humble outsider,” there to “be a sponge.” Her test for whether you are ready is blunt: “If you can’t interview 100 people, are you ready for this?”
Try this: Before you build, interview a hundred people about the problem itself. Come in as a humble outsider, full of questions and light on opinions.
2. The validation that feels good teaches you nothing.
Emily’s early interviews flopped for a reason most founders will recognize. “I was so excited to tell people about this idea,” she said, so friends and colleagues told her exactly what she wanted to hear. Her phrase for that warm, useless feedback stuck with me: “Don’t just get validation, it helps you zero. People just saying yes to you helps you zero.” What works instead is coming in with “a neutral framework of what you’re trying to learn,” and avoiding the pitch entirely. As she put it, “the less you can talk and the more you can come prepared with questions, the better.” Now she actively recruits the people who will tell her the truth.
Try this: In your next user conversation, ask only about what they actually do today. Keep your idea out of it. If everyone loves it, you learned nothing.
3. Build the skateboard first.
Emily and her co-founder built their first product too big. “We got the curse of knowledge,” she said. “We had way too much context,” so they shipped something accurate and overwhelming. Users were clear: “It’s a lot of information, but it’s not helpful because it’s too much information.” The reframe she kept coming back to is an old one, and it still lands: “If you’re thinking about building a car, you don’t build a wheel, you build a skateboard.” The smallest usable thing beats the complete unusable one. Her other regret was speed: “I wish we’d thrown money at things sooner. The dragged out pain sucks.”
Try this: Cut your next build to the smallest thing a real user can use this week. If it is accurate but nobody wants to touch it, you built the wrong thing.
4. There is no glory in being a solo founder.
Emily had been on teams her whole career, and she knew she did not want to build this one alone. “I don’t need to be a solo founder,” she said. “There’s no glory in that. It’s very lonely, and I’m more productive with someone.” She brought on a former colleague as co-founder, partly because the problem itself demanded it: “This is not a technical problem. It’s a human problem. It’s a trust problem.” The honest part is what came after. At first they were “too polite,” editing each other’s work and dodging the hard calls. What fixed it was structure, “a DRI on everything, a deadline, what done looks like,” and a willingness to have the uncomfortable conversations early.
Try this: If you are white-knuckling something solo, name the one piece you dread most and find a partner or a hire for it. Then put a clear owner and a deadline on everything between you.
From Emily: “The sooner you can close that gap and have the really uncomfortable conversations, knowing that nobody’s feelings are getting hurt, what’s best for the business, the sooner the better.”
5. Not making a choice is making a choice.
Emily’s father died suddenly, on a day he spent doing exactly what he loved. “This man was living the exact life he wanted unapologetically,” she said. “And if I looked at my day to day, was I doing that? The answer was no.” Her own life had narrowed to her job. “I used to have hobbies, and now I have GitLab.” The contrast cracked something open. Her first week back at business school was the most alive she had felt in years, and she quit her job the next day with no plan. The line she lives by now is the one to sit with: “Not making a choice is making a choice. You’re choosing to stay where you are.”
Try this: Name the change you keep postponing. Staying is a decision too. If you are making it, make it on purpose.
From Emily: “Life is too short to not try.”
Resources Emily mentioned
Fall in Love with the Problem, by the founder of Waze. The book that pushed her to stop defending her solution and obsess over the problem instead.
The Mom Test. How to interview people without leading them into telling you what you want to hear.
Save the Cat. A screenwriting book she calls the best marketing book she has read. Who is the character, and who is this for.
Language and the Pursuit of Happiness. On how changing the way you communicate changes the relationship. Her test: “Do you want to be right or do you want to be happy?”
What Color Is Your Parachute? The career-finding book that first pointed her toward marketing.
The GitLab Handbook. The public playbook she credits as the foundation most all-remote companies copied.
My First Million, a podcast. Practical, actionable tips.
A Typical Disgusting Display, a podcast by two Family Guy writers on craft and business, and how to show up when you don’t want to. The run has ended, and the back catalog is still worth it.
Poker Power, a poker training program for women. Emily uses poker as her best networking, with “captive attention for four hours” among other founders.
P.S. What is the problem you keep circling but have not let yourself go all in on? Hit reply and let me know.
Work with me
I’m Dar Patel, an ICF-certified executive coach (PCC), I have worked with founders and executives, and am the writer behind The Inner Game, the weekly newsletter of Little Pursuits.
My goal is to support founders, executives, and individuals doing one of the hardest things we can do: build and scale something from the ground up.
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