Spotlight: Pogo Wants to Simplify Insurance for Freelancers and Solopreneurs

Spotlight: Pogo Wants to Simplify Business Insurance for Self-Employed Like Freelancers and Solopreneurs

Insurance is a difficult thing for a lot of businesses to navigate, especially freelancers and solopreneurs. But Pogo wants to make the concept simpler. The company is taking a unique approach to helping the smallest businesses understand their insurance options. Read more about the business below in this week’s Small Business Spotlight.

What the Business Does

Provides insurance for self-employed individuals.

Co-founder Hannah Sullivan told Small Business Trends, “We provide business insurance to self-employed people like freelancers and entrepreneurs. We also offer advice, tips, and tricks regarding how to successfully work for yourself.”

Business Niche

Making business insurance easy to understand.

Sullivan says, “Pogo has three founders. Myself, Jade, and Steve. Steve’s my dad and Jade’s my wife. Jade and I met in grad school for branding and innovation and used to work at an ad agency together. My dad owns several insurance agencies and has been in the industry for over 30 years. Because Jade and I don’t come from an insurance background, but rather a design and communications background, we have worked very hard to break down “insurance speak” into easy to understand bits for everyday humans.”

Spotlight: Pogo Wants to Simplify Business Insurance for Self-Employed Like Freelancers and Solopreneurs

Small Business Deals

How the Business Got Started

Because of insurance confusion.

Sullivan says, “Jade and I were working at Wieden+Kennedy in New York as a creative team. We always knew we wanted to do our own thing, and when my dad offered us a chance to work on his new back-end insurance program, we moved back to Richmond. After several months of “what the hell is going on” we figured out that we could probably make business insurance way easier. From there, Pogo was born. And since a lot of our peers are in creative industries, doing work on the side, and are also not insurance experts, we thought the idea could actually help people.”

Biggest Win

Finding a way to help entrepreneurs.

Sullivan explains, “Insurance is very confusing. And when you run your own show, you have a million things to figure out- meaning many hours digging around on the internet. That’s why we want to help self-employed businesses get the right insurance without feeling like their head is going to explode. (Especially because business insurance would be of no help, in that case). So, I guess our biggest win is being able present business insurance in a way that preserves your safety and your sanity.”

Biggest Risk

Breaking into an unknown industry.

Sullivan explains, “For Jade and I, choosing to work in insurance was the biggest risk. Her background is in film and technology, mine is in marketing and design. At the time we were 100% not insurance people. I remember the first few weeks when I got started… I would just constantly black out like, what the heck is happening right now?! How did I get here?! Jade worked in commercials and I was straight out of school. We had a brief stint at an ad agency, but other than that, we didn’t have much “business” experience. I’d say the true risk taker here was Steve, but he must have known that our obsession with making good work could apply to anything.”

Spotlight: Pogo Wants to Simplify Business Insurance for Self-Employed Like Freelancers and Solopreneurs

Lesson Learned

Embrace the challenge.

Sullivan says, “I wish I hadn’t been so hard on myself. It’s like Jade and I would just pass a huge ball of stress back and forth, every day, for months. We were filled with such doubt because we weren’t “insurance people.” Looking back, we should have just owned it! We had fresh eyes, and that’s the reason our company has an edge. It’s relatable to real people because it was made by real people. Not simply by insurance experts.”

How They’d Spend an Extra $100,000


Sullivan explains, “This summer Jade and I traveled throughout Mexico while renting out coworking spaces. It was so inspiring and we were able to meet tons of freelancers and entrepreneurs. It was great to get a chance to talk to them about their lifestyle and how important (or unimportant) they perceived insurance.”

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Find out more about the Small Biz Spotlight program

Images: Pogo; Top Image: The team’s coworking space in Mexico, Second Image: Hannah Sullivan 2 Comments ▼

Annie Pilon Annie Pilon is a Senior Staff Writer for Small Business Trends, covering entrepreneur profiles, interviews, feature stories, community news and in-depth, expert-based guides. When she’s not writing she can be found exploring all that her home state of Michigan has to offer.

2 Reactions
  1. Interesting idea and a tough crowd to sell to. Many don’t see the need for insurance.

  2. This is nice. Freelancers need some insurance too. And their number is constantly increasing.