How one founder learned the best way to win is to know when to quit

Bailey Seybolt

Congratulations on your recent fundraise for your company DripShop. You’re going to be the Shopify for livestream commerce. Tell us more.

When Covid hit, I knew everything was going to be about video. So the question was really what problem to solve. My co-founder CEO, Javaughn Lawrence saw this really interesting behavior emerging on Facebook Live, where people were doing live sales of trading cards – trading crazy amounts of money. In China, livestream commerce is already a $60 billion-plus market, but no one’s quite figured it out in the US. Collectibles felt like the right entry point, but our plan is to keep expanding into interesting categories – like NFTs.

DripShop isn’t the first company you founded. Have you always been a founder in search of your idea?

Startups have been my true passion for a long time. I’ve worked on a few different ideas over the last six years. I started my first company, Sensei Hub in 2015. It was all new – we hustled for two years and raised something like $160,000. It was a really humbling experience. And it was incredibly valuable in that way, for the things I learned and brought to my next company.

What was the most important thing you learned?

With SenseiHub, I learned everything that goes into putting a product together. But we really didn’t get the escape velocity we needed. We didn’t know what market traction looked like and we didn’t know when to quit.

This time around, my co-founder and I iterated on this idea for 3 months after tossing out some other ideas. And within five months we were doing $30,000 in revenue. Then it started doubling every month. I learned how to recognize when something is working. Investors can see that too and it becomes a lot easier to raise money.

How do you think about finding market traction as a founder?

It really comes down to your founding style. I wanted ownership, I wanted to see impact directly on the customer, so building consumer products made sense.

The other thing I’d say that’s really important is defining your success metric, so you know what progress looks like. This is something I didn’t do at my first company. And success doesn’t have to be money, it could be the number of new users signing up, monthly growth, how many users are making purchases. But you need a way to know you’re on the right path.

How has consulting with Tribe fit into your journey as an entrepreneur?

Before Tribe, I’d already spent some years consulting to pay the bills, and there was a big learning curve there. I did a lot of projects for people who didn’t have any sense of how much investment was required. With Tribe, I got hired for my actual value for customers who really understand and respect an engineer’s true worth.

What advice would you give to other founders in the community?

A journey to build more sophisticated products has to start with simpler ones. Look at Elon. Before he built Tesla he had many exits from products easier to pull off. So I’d say: execute simply first. Take the long view of your founding journey.

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Bailey Seybolt
Bailey got her start in storytelling as a journalist, before pivoting to tech content development for unicorn startups from Montreal to San Francisco – helping build brands and shape stories to drive business results.