Raising capital? Check out my ebook, Pitching Angels, as you prepare your pitch.
Sean Harper built a product that helped customers compare payment processors. There was just one problem: none of the options were very good.
Customers would study the comparison, then ask which provider they should choose. A year later, they'd come back with complaints about broken APIs, confusing billing, and underwriting problems.
Sean told me:
“We realized we were doing a really good comparison of really lousy options.”
The company was FeeFighters, which eventually sold to Groupon. Today, Sean is co-founder and CEO of Kin Insurance, with roughly 850 employees at the time of our conversation.
I recently caught up with him about the lessons he carried into Kin. The biggest one challenged something founders hear constantly: start with the smaller, safer idea.
1. The “Safe” Idea Cost Him Time
Sean and his team understood that payments needed to become easier. But starting their own payments company felt out of reach, so they built a comparison engine instead. Some early investors liked the less ambitious model because it was safe and achievable.
Customer feedback eventually pushed them toward the product they should have built first: their own payment processor.
They paused the business for a year to build it. By the time they launched, Sean felt they'd lost their window to establish themselves ahead of better-funded competition.
“It's actually risky to do the thing that looks safe. We ensured we wouldn't win by doing the safe thing.”
That's Sean's assessment of his own experience, not a guarantee that the biggest idea always wins. But his point matters: a less ambitious business can consume just as many years of your life.
2. Choose the Opportunity Deliberately
FeeFighters grew out of a frustrating experience with a payment processor. For his next company, Sean didn't want to limit himself to problems he'd personally encountered.
After the exit, he spent about a year exploring financial services. Having worked in venture capital, he approached the search with an investment thesis.
He looked for two things: intermediaries earning substantial money without adding enough value, and new data sources that could improve pricing and underwriting.
Homeowners insurance scored best.
When we suggested he'd systematically de-risked the opportunity, Sean pushed back:
“I wouldn't say we de-risked it. We just had a thesis.”
I liked that distinction. Research doesn't make a startup safe. It gives you a better basis for deciding which risk to take.
3. At 850 People, Context Doesn't Travel on Its Own
Sean wants decisions made by the people with the most relevant knowledge, rather than automatically sent up the management chain.
The best messages get harder to spread as a company grows.
When Kin was small, information spread almost by osmosis. A conversation would happen, and the context would work its way through the company. At 850 people, that no longer works reliably.
Sean now writes a weekly note. Kin holds all-hands meetings every two weeks. He has a chief of staff, communications support, and AI helping with internal communications.
“You have to build infrastructure just to keep people coordinated.”
If you want people to make good decisions independently, you have to give them the vision, freedom and boundaries to do it.
4. Learn Which Problems Not to Fix
Delegation is still something Sean struggles with.
“You have to accept that other people will do the job differently than you would, and that's okay, even when a lot of the time it's worse.”
At 10 people, Sean could participate and fight every battle. Now, he sometimes notices something wrong and deliberately leaves it alone because something else matters more. Sometimes it improves without him because another person is already on it.
This led to a friendly disagreement. Sean initially said being a founder and being a CEO weren't all that different. I pushed back: running around fixing everyone's problems eventually means going over your executives' heads.
We landed on a useful distinction. A founder should retain the ability to zoom in, without zooming in everywhere.
5. Keep the Startup Mojo
What worries Sean now is losing Kin's entrepreneurial energy as it gets larger.
He's still excited enough about building software that it sometimes keeps him awake. He wants to preserve that spirit inside a much bigger organization.
Kin's mission remains practical: make homeownership easier, better, and cheaper. Sean described work beyond insurance, including help with mortgages, property taxes, and preventative maintenance.
The ambition is bigger, but the focus is still on solving customer problems.
The One Thing: Make the Shot Count
Sean spent roughly six years building FeeFighters and working inside Groupon afterward.
His calculation was simple: if each company takes six years, you don't get unlimited attempts.
“I didn't want to waste another shot doing something small.”
My takeaway: be disciplined about how you build. But don't let the desire to be capital efficient talk you out of building something worth the years you're going to put into it.
Ready to pitch your big idea to angel investors? Check out my ebook, Pitching Angels, as you prepare for those conversations.