Meet the Disruptors: Bryan O’Connell of Huckleberry On The Three Things You Need To Shake Up Your Industry

Jason Hartman
Authority Magazine
Published in
5 min readJan 7, 2021

Huckleberry is disrupting the antiquated insurance industry by focusing on supporting small businesses through transparency and ease in business coverage. We’re disruptive in that a relatively minor mistake in the underwriting process can cost millions and insurance is highly-regulated, so Huckleberry is streamlining the process efficiently with technology.

We are 100% paperless and provide a seamless and easy-to-use digital platform that allows small business owners to get a quote and purchase insurance coverage that fits their needs in just minutes. We’ve eliminated the hours of collecting paperwork and days anticipating quotes.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Bryan O’Connell, co-founder & CEO at Huckleberry, a platform with a mission to rebuild business insurance from the ground up by providing small business owners with the capability to manage all of their insurance needs through its transparent, easy-to-use interface. His career has spanned insurance and tech — he started out in the actuarial department of Canada Life, before joining a San Francisco based venture capital fund where he invested in technology startups. Bryan holds a first class honors degree in Actuarial Science from University College Dublin and an MBA from Harvard Business School.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Huckleberry was born due to the painful process I encountered when purchasing business insurance at a prior startup. Having worked at an insurance carrier, I knew that it was possible to build a platform that eliminates tedious offline paperwork and puts the small business owner first. Since I studied actuarial science in undergrad, I understood the math involved with small business management.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Huckleberry is disrupting the antiquated insurance industry by focusing on supporting small businesses through transparency and ease in business coverage. We’re disruptive in that a relatively minor mistake in the underwriting process can cost millions and insurance is highly-regulated, so Huckleberry is streamlining the process efficiently with technology.

We are 100% paperless and provide a seamless and easy-to-use digital platform that allows small business owners to get a quote and purchase insurance coverage that fits their needs in just minutes. We’ve eliminated the hours of collecting paperwork and days anticipating quotes.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Some may say that the insurance industry is a necessary evil. While the coverage is necessary to ensure protection against unforeseen or unfortunate events, the process of finding coverage that works for your business doesn’t have to be so painful and overwhelming. Huckleberry is working to bring small businesses up to speed through a digital platform that is easy to understand and manage.

I think disrupting an industry is positive when it makes people with in that industry more productive, rather than wholesale eliminating their jobs. We definitely see ourselves in the former category — we don’t seek to eliminate the role of the insurance agent — we seek to eliminate the tedious tasks that they have to perform.

We are sure you aren’t done. How are you going to shake things up next?

Huckleberry is currently working on developing a Pandemic Business Interruption plan. The new policy will be one of the first of its kind, designed for small businesses impacted by pandemic-related stressors and costs, and will be available in 2021.

Unlike other insurance companies coming to market with new pandemic policies, Huckleberry’s will be among the only plans geared directly toward small businesses. We are engineering this new plan to offer quick and automatic payouts based on local, county-level actions and closures, eliminating excessive reporting and saving companies time when they need it most.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

I really enjoyed Sam Walton’s book on the founding of Walmart. Written in the early ’90s, many of the lessons are highly generalizable to today. I particularly liked how its not a book about tech, but that some of its lessons are highly applicable to tech. At its core, Walmart’s key innovation was making a wider variety of goods more accessible to a wider variety of people at a reasonable price, and broke down barriers to purchase. I view Huckleberry through the same lens: we are breaking down what were extremely arduous hurdles to obtaining business insurance, and increasing price transparency.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Bringing the most amount of good to the most amount of people is a high bar, and given that as I write this multiple COVID19 vaccines are being announced, I’m not sure that we can compete with some of the work that is being done there. However, in terms of the movement that we hope to inspire: we’ve always believed that small businesses are the backbone of the US economy, and that small business owners should be able to focus on what they do best: be it cooking delicious food, offering quality fitness instruction and more. But small business owners are often distracted by tedious tasks that bear little relation to their core competency: be it payroll, bookkeeping or insurance. Our fundamental believe is that companies will emerge that make all of these process orders of magnitude more simple.

This was very inspiring. Thank you so much for joining us!

About the Interviewer: Jason Hartman is the Founder and CEO of JasonHartman.com, The Hartman Media Company and The Jason Hartman Foundation. Jason has been involved in several thousand real estate transactions and has owned income properties in 11 states and 17 cities. His company helps people achieve The American Dream of financial freedom by purchasing income property in prudent markets nationwide. Jason’s Complete Solution for Real Estate Investors™ is a comprehensive system providing real estate investors with education, research, resources and technology to deal with all areas of their income property investment needs. Through Jason’s podcasts, educational events, referrals, mentoring and software to track your investments, investors can easily locate, finance and purchase properties in these exceptional markets with confidence and peace of mind. Jason educates and assists investors in acquiring prudent investments nationwide for their portfolio. Jason’s highly sought after educational events, speaking engagements, and his ultra-hot “Creating Wealth Podcast” inspire and empower hundreds of thousands of people in 189 countries worldwide.

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