Though I’ve had a lot of different day jobs over the years, 3 things have been constant in my career: using creativity, helping people, and doing both of those through technology startups.
From the first day I started work at the software startup that was my first real job after grad school, I was immediately hooked by startup culture and the concept of creative problem solving + technology becoming a solution that can help dozens, hundreds, thousands, or even millions of people at scale. While the company that gave me my first startup job didn’t make it and I had no idea what I was doing back then, the experience set me on a career path that I have truly loved and nearly 30 years later, startup leadership is still a career that I find immensely satisfying and exciting.
I’ve started, invested in, mentored and worked for more than 20 different startups. Not all of them have gone anywhere, but I learned important lessons from all of them. Here are 4 of my favorite startup experiences, starting from the present and going back to the first one I founded.
Smartria
Co-Founder and CEO
Oct 2015-Oct 2023
I had nearly 20 years of startup experience when Smartria was launched, but I still learned a lot of new lessons, and some of them were fairly difficult to go through. But the high points at Smartria were pretty fantastic.
Over 8 years, more than 40 people built Smartria into a best-in-class solution in a highly competitive FinTech industry, earned a hard-won reputation for excellent customer service, and attracted over 2,700 customers comprising more than $600Billion in assets under management.
I feel great about what we achieved together and can’t wait to see where the company is going from here.
KnoxvilleJukebox
Founder and CEO
2010-2011
KnoxvilleJukebox was a music streaming and visual arts portal for local artists, launched before Spotify came to the US. KJ was a lot of fun and it was the first time I combined my love of art or music with a technology business. I added KJ to the KnoxvilleBusiness brand (below) and connected their databases to drive content, traffic and revenue from both sites to the other.
It worked! 1 year after I launched KnoxvilleJukebox, the KB/KJ business was acquired.
More than 10 years later, even though it’s no longer innovative, I still love the idea of a tech-forward portal for local music and art.
KnoxvilleBusiness
Founder and CEO
1999-2011
For a city of its size, Knoxville is a pretty cool place to live. That was true back in the late 90s when the redevelopment of downtown was just beginning to get some legs. I started KnoxvilleBusiness.com with the intention of doing something smaller than my previous attempt with Give2Net. I wanted to help local businesses to be found online and to generally promote our fair city as a place with boatloads of natural beauty, arts, culture and some pretty great people, too.
It was a 12-year journey from basically a local business blog to a full directory of businesses, online advertisers, and community members.
The final design you see to the left was what the site looked like when it and its sister site KnoxvilleJukebox were acquired.
Give2Net
Founder and CEO
1998 – 1999
Give2Net was an online directory and marketplace for non-profit and for-profit companies, and it was my first digital startup. in less than a year, I conceptualized, built, marketed, wildly succeeded, and lost my shirt on this company. I collected information regarding thousands of non-profit entities, attracted for-profit businesses interested in supporting non-profits with discounted and pro bono services, and grew traffic from nothing to being ranked among the top 8,000 websites in the world for site visits. Not bad for a total noob!
I also made several pretty serious rookie mistakes. Ultimately, it was a short-lived company but one that taught me many critical lessons and started me on my path to much more successful ventures.
