Best's Review


An Entrepreneur’s Story: Caribou Honig's Questions for Ilya Bodner of Bold Penguin

Insurtech veteran Caribou Honig discusses insurtech strategy with an entrepreneur who launched a company later acquired by American Family.
  • Caribou Honig
  • January 2022
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The year was 2016. Insurtech was barely a recognized term in the boardroom and nascent as a category in venture capital. In that year, a credible entrepreneur by the name of Ilya Bodner came to pitch me to invest in his whimsically named company, Bold Penguin.

Bodner described his intent to better connect carriers and independent agents providing coverage for small businesses. He spoke to the “technology stack” his team was building and how he would get the flywheel spinning by also providing leads to the agents. Bold Penguin was primed, he said, to create a two-sided marketplace with network effects and the cost efficiencies of software.

I passed, thinking,“This is either a genius concept or strategically bankrupt, and I cannot figure out which.”

Five years later, the company was acquired by American Family Insurance Group—by all accounts, a success for its venture capital backers—and Bodner continues at the helm to pursue his vision for the company. American Family is No. 12 in AM Best's ranking of the Top 200 Property/Casualty Writers based on 2020 net premiums written. Following is an interview with Bodner.

Related: The Billion-Dollar Question: What's the Allure of Investing in Insurtechs?

Well, now I know Bold Penguin was actually a genius concept. When did you know as well?

Ilya Bodner

"Underwriting is another area that is very ripe for the next wave of innovation. As an industry, we aren't yet leveraging data and technology to its full potential in this space, to the detriment of the entire value chain."

Ilya Bodner
Bold Penguin

Bodner: Can I say 2015 when I first came up with it? Seriously though—I knew it had legs when I started really talking to agents and carrier leaders and saw how much the concept resonated. We were tackling a problem that had plagued their organizations for years. We visited over a hundred agencies on a massive roadtrip in 2016 and it was clear that we'd hit a hot button focusing on solving small-commercial insurance.

I might argue there are two types of insurtech startups. Some are trying to compete head-on and put the existing players out of business. Other startups are trying to bring the benefits of tech to the incumbents. Bold Penguin falls in the latter category. What are the distinct challenges of partnering with existing players?

Bodner: Certainly there's the initial challenge of getting in the door, of trying to sell a new technology to organizations with many decades of history and layers of stakeholders. You're dealing with technology debt, existing workflows and tackling that “build or buy” decision. But we've been very fortunate with our partners in that each one has truly been a partnership, working side by side to solve their biggest small-commercial challenges. We've learned from each other and grown together and it's been an incredibly rewarding journey.

Well in that case, what advice would you give to the chief strategy officers or heads of business development at brokers, carriers and reinsurers as they think about partnering with insurtechs?

Bodner: First off, you must be able to build and leverage application programming interfaces. With APIs, you can connect to distribution platforms, like the Bold Penguin Terminal, and sell products to hundreds of thousands of small businesses. Also, APIs are required to leverage new data solutions. We have a new data science team tackling submissions and coverage analysis. The insurance industry has to be able to leverage these and other solutions through API feeds.

I've written previously in Best's Review about VC math—the fact that venture capital is fundamentally geared to investing in asymmetrically big winners. Are there any product categories or parts of the insurance value chain you think are especially ripe to produce “asymmetrically big winners?”

Bodner: Underwriting is another area that is very ripe for the next wave of innovation. It hits on several key areas that impact a number of stakeholders relevant to distribution, product and customer experience. As an industry, we aren't yet leveraging data and technology to its full potential in this space, to the detriment of the entire value chain.

Related: Insurtechs' Innovation, Big Data Catch the Attention of Reinsurers

To my own surprise, it turns out that COVID-19 became a tailwind for many startups in the insurance sector. I'd be remiss if I didn't ask how it affected Bold Penguin. While recognizing the human toll, was there a silver lining as it affected your business?

Bodner: I've seen COVID discussed as a forcing mechanism of sorts when it comes to digitization and I think there's some truth to that. The overnight pivot to a largely virtual world removed the training wheels in a sense—it was sink or swim. We were in the fortunate position of being there to support our partners during that time as well as onboard new partners, some of whom were incentivized to fast-track elements of their digital transformations to meet the changing needs of their customers. So I'd say that COVID did increase the pace of adoption and innovation for us and many others across the industry.

Bodner's experience building Bold Penguin holds several lessons for those trying to predict the future of insurance. Partnerships have proven crucial for nearly all successful insurtech startups and that will likely continue. Embracing pivotal technologies—including, but not limited to, APIs—is key to unlocking new opportunities. Finally, a mindset of optimism and commitment to overcome obstacles—such as investors who fail to recognize the genius of an idea—is a key ingredient to driving success in our industry.

Best’s Review contributor Caribou Honig is chairman and co-founder of InsureTech Connect, as well as a partner at SemperVirens Venture Capital. He can be reached at

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