Sean Harper – Iterate Until You Come Up With a Good Market Fit

Nov 6, 2022

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BIO: Sean Harper is the co-founder and CEO of Kin, an insurance company built from scratch on modern tech to make it easier and more affordable to insure a home.

STORY: When Sean started his first business, things got so hard that when a company offered to buy it, he sold it without a second thought. Ten years later, he still regrets this decision.

LEARNING: Believe in yourself. Be systematic when setting up your business. Iterate until you come up with something that the market appreciates.

“You make things happen by convincing people of your vision, and that’s what selling is.”

Sean Harper

Guest profile

Sean Harper is the co-founder and CEO of Kin, an insurance company built from scratch on modern tech to make it easier and more affordable to insure a home.

A self-proclaimed tech geek, Sean has spent his career developing apps to revolutionize antiquated industries. When he realized that the homeowners insurance industry was still being managed unlike any other consumer financial products today (relying on paperwork, legacy IT systems, and distribution through local brokers), he saw an opportunity.

Sean co-founded Kin as a tech-based insurance agency in 2016 and has grown it to a fully-licensed home insurance carrier supported by a team of over 400 employees. With a focus on ease, affordability, and exceptional service, Sean and his team are changing the way insurance is done.

Worst investment ever

Sean started his previous company, a payment processing business, in 2009. It was tough for Sean to start this company. He raised a bit of angel money and tried one version of the product, but it didn’t sell well, so he pivoted and rebuilt the product from scratch.

Growing the business was getting harder by the day, and Sean’s investors were losing patience. A prominent public company came along and wanted to buy Sean’s company for its technology. Sean sold the company.

Three years later, companies in the same industry, like Stripe, were now big multibillion-dollar businesses dominating the industry. These companies wiped out Sean’s business. Just three years after selling the business, there was no trace of it. This was a very disappointing outcome, and it made Sean regret selling the business. He should have stuck with it, even though it was hard. Ten years later, he still regrets that decision.

Lessons learned

Believe in yourself.
Be systematic when setting up your business.
Have the right investors, supporters, and mentors.

Andrew’s takeaways

If you’re struggling to raise capital, chances are you need a better market fit with your product.
Iterate until you come up with something that the market appreciates.
When you sell your business, don’t go work for the buyer.
When you start a business, go as fast as possible to get between $3 million and $5 million in revenue.

Actionable advice

Surround yourself with people who have conviction and who believe in your idea.

Sean’s recommended resources

Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein. The book is about statistics, probability, and early capitalism before we even had an economy.

No.1 goal for the next 12 months

Sean’s number one goal for the next 12 months is to get to profitability and not have to raise money every year from investors.

Sean Harper – Iterate Until You Come Up With a Good Market Fit

Guest profile

Worst investment ever

Lessons learned

Andrew’s takeaways

Actionable advice

Sean’s recommended resources

No.1 goal for the next 12 months

Parting words

Connect with Sean Harper

Andrew’s books

Andrew’s online programs

Connect with Andrew Stotz:

Further reading mentioned