5 Questions with Reid Holzworth of TechCanary

Startup Milwaukee has partnered with Cognition for 5 Questions, a series that highlights entrepreneurs, investors, and leaders committed to advancing Milwaukee’s startup ecosystem.  This edition features Reid Holzworth, Founder and CEO of the insurance software company, TechCanary, which was recently ranked #393 on Inc. 5000’s fastest growing companies.  This interview has been edited for length and clarity.


How did TechCanary get started and then grow into the #1 insurance solution on Salesforce.com?

TechCanary was born when I owned my own insurance agency.  As an entrepreneur, I was always looking for ways to streamline the business and found myself seeking a software solution that didn’t exist. I decided to build it myself by partnering with Salesforce.com, who then saw its value to the insurance industry and approached me to bring it to market. So I started operating TechCanary and rebuilding the product out of an apartment in Riverwest.  Once we took it to market in 2013, it exploded and we’ve grown 300-400% year-over-year since. It was a lot of luck but also a lot of days riding my bike to work from 4:00am to 8:00pm. It’s been hard work, but we’ve done it by assembling the right team, working with the right people, and developing the right culture.

What’s the “right” culture?  Lots of companies tout a great culture with ping pong tables and free snacks.  Is that TechCanary?

The right culture has to do with hiring people that share the same core values as our organization.  When people walk into our office, they see that everyone is grinding and working hard but they’re happy and having fun.  Yes, we have all the cliché stuff like foosball tables, and snacks -- there’s even a racecar in the middle of our office.  But we don’t do all that to dangle a carrot in front of people, it’s so they can grab a quick bite or detach for 20 minutes with a game of ping pong.  Just this past week, one of our employees told me this is her first job where she actually prefers coming in to the office instead of working from home. That’s the kind of culture you want.  

It’s great you can offer that as a successful entrepreneur.  What do you think it takes to become one?

Entrepreneurs have to be a little crazy.  It requires self-confidence, getting lucky, honoring your word, and the gift of gab.  You also have to be able to pivot. It’s been interesting for our company to have grown so fast because just when we hit the next level everything we thought we figured out no longer works.  Just 60 days ago we went through an entire reorganization because after growing so fast various departments weren't aligned.  Even though we were under the gun on a lot of things, I threw in a grenade and blew up an entire department and now it’s awesome. We broke out of our silos and even though it may have set us back a little at the time, we’ll now move forward way faster with everyone aligned. So you have to be a little crazy and willing to make tough decisions then deal with the outcomes.  

With that in mind, what’s been your toughest business decision to date?

Shortly after we launched, I was renting a tiny office above a Panda Express for me and 2 employees when I was approached by a private equity company.  They were looking to get into the insurance software business with a product exactly like ours so they ended up putting a huge offer in front of me. It was the most money I had ever seen in my life, so I had to make the hardest business and personal decision ever because I had to have confidence.  I had to decide whether I take their money, run with their cushy job, and bail on my employees, or say I don’t care that I smell like Chinese food right now, I can do this myself. Most people seeing that check would have decided that was a win right there, but because I didn’t the business is now worth 20 times more than that check was.  

That’s awesome!  And now I’m hungry for Chinese, so let’s wrap up with one more question.  As an industry leader that could be located anywhere, why have you chosen to stay in Milwaukee?

A lot of people we work with also wonder that, but Milwaukee really is a hidden gem.  It’s a cool culture where people are down-to-earth and not pretentious. People are also loyal, I love that the core values of the city’s culture match the core values of our organization.  The cost of living is also great, and if you want the big city, Chicago is super close. Logistically, we’re in the middle of the country so it’s easy to fly anywhere in the country in 3 hours. And as a tech company, there’s no one else in the state that does what we do.  So culturally, logistically, business-wise, it’s all great.

Asha Dewan is the owner of Cognition, a writing agency located in Milwaukee, WI.  Cognition specializes in creating digital content to help businesses save time and bandwidth while maintaining visibility.