Why I’m Working at an Insurance Company

I just finished a year off.

As I mentioned here (Why I’m Taking a Sabbatical), I set out to have an adventure with my family and to better answer the question “what am I on this earth to do?”  It was an incredible opportunity to step out of regular life and take a long, hard look at myself—an out of body experience. Sure it was scary to be on the sidelines and my bank account hated it, but it was one of the most valuable things I’ve ever done.

There are obvious reasons it was awesome, like precious, 100% time with my family and teaching my son. But I also learned something very valuable about myself. I learned that I love to create things—it’s what makes me come alive.

This is sort of a hard thing to realize because my creative outlets are limited by my lack of skills. I can’t paint or draw or sculpt. I can’t sing or play an instrument or compose a symphony. I can’t dance (at least not well). What does that leave? Thankfully, it leaves something I’ve already done . . .

Create Ideas.

To me, there is nothing quite as amazing as taking an idea that develop in your mind (often with people smarter than you) and help to launch that idea and see it take on a life of its own. To see it solve a problem and make a difference in peoples’ lives. Ask any grizzled entrepreneur and they will likely agree that the experience is intoxicating and will have you coming back time and time again for more.

I want to continue working in the world of ideas.

That’s why I’m excited to announce that I just started a new role as an “Entrepreneur in Residence” at American Family Ventures. It’s a great opportunity for me to support the innovation initiatives that American Family has underway, at the same time that I explore solutions to the problems that matter to me.

This is only the second time in my professional life that I’ve worked* for a company that I didn’t help start, but the decision was a no-brainer for me for several reasons.

Here’s why:

“You are the average of the five people you spend the most time with” Jim Rohn

The innovation team at American Family has some serious horsepower. I love working with people that are smarter than me. There is no better way to become better at what you do.

The phrase “Insurance Startup” is no longer an oxymoron

Timing is everything and the insurance space is reaching a tipping point. Industries with high barriers to entry because of complicated legal structures and/or high capitalization requirements used to be insulated from the Mark Zuckerbergs of the world, but one look at what is happening in markets like financial services (e.g., Lending Club) and transportation (e.g., Uber) shows that this is no longer the case. The traditional insurance incumbent moat is eroding, a fact not lost on smart incumbents. The space is wide open.**

American Family isn’t just giving lip service to being innovative

Entrepreneurship is hot right now, and almost every Fortune 500 company is talking about innovation. But a lot of it is just talk while the C-Suite continues to focus myopically on making its next quarterly number. American Family’s innovation push, in contrast, is coming from the CEO and leadership with a real mandate. They are taking the long view. And backing it up with real actions. Case in point—a company using innovation for their public window dressing wouldn’t quietly (and massively) increase the $’s allocated to their Venture Fund. But guess who did just that?

Brown Star this is not


Empathy is a super power

I’ve sat across the table from venture investors and big company biz dev and M&A folks for 15 years. I now get to sit on their side of the table—get an inside view of how they make decisions, what keeps them up at night, better understand their incentives and what their world is really like. Empathy is a hidden super power of really good entrepreneurs (a fact I’ve written about before) and this experience is going to make me a better/stronger/faster entrepreneur.

A person’s value system is the sum total of their actions. A person’s words, thoughts, decisions, promises have no value until they act upon them. Christian Hacker

I’ve done a lot of reading and thinking during my year off. I’m excited to jump back in and start making things happen again.


*I’m an independent contractor, like an Uber driver 🙂

**This is not a guarantee that I’m going to start something in the insurance space or even launch another stand alone start-up from scratch, but many of the themes being addressed in this space (consumer data, customer relationships, social risk, Aggregation theory) fascinate me.

6 thoughts on “Why I’m Working at an Insurance Company

  1. Congrats on the new role. American Family Ventures has a great focus compared to other current and past fortune 500 VC programs.

    I’m looking forward to you sharing more insight with your new role.

  2. Pingback: Find the Experts-How to use Podcasts, Curated Lists and other Online Sources to get Smarter/Faster/Better | Blog of Mark McGuire

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