Troy R. Underwood is an industry disruptor. Part technologist, part economist, and all innovator, he revolutionized the motor vehicle industry with the nation’s first electronic title system for financial institutions, which was later sold for $106 million. His healthcare venture, benefitsCONNECT, innovated healthcare benefits administration and resulted in a highly successful acquisition. His new book is How to Launch Your Side Hustle: Start and Scale a Business with Minimal Capital. Learn more at 

Podcast Highlights

Who is Troy Underwood? 

Troy considers himself a necessity entrepreneur and has been doing the entrepreneurial thing since elementary school. Troy has sold all sorts of products including greeting cards, seeds, and computers. Whatever the opportunity was, Troy was willing to take advantage of it.

For the average entrepreneurial minded person, the problem is having too many ideas. They need to take these ideas and pick one, then execute, and then when they get bored they have to keep pushing instead of flipping to the next one. Ideas are everywhere, execution, perseverance, and discipline is what’s rare. Even a mediocre idea, when executed well, can work out.

Troy’s original plan was to become a doctor, not an entrepreneur. It wasn’t until Troy took an economics course on a dare that he realized that he loved the study of economics and completely switched tracks. He kept up his involvement in computers and software development, and found himself in the right place and the right time to offer a solution that jump-started a business. 

Is now the right time to start something?

Now may actually be a great time to start a new business, especially for those who have been laid off with nothing to go back to. If you’ve been thinking about it for a while and you have an idea, if everything else is relatively stable, now could be the right time to give it a shot.

Being an entrepreneur isn’t an exact science, you just have to take the cards you're dealt and play them the best you can.

If you’re someone who craves certainty and security, don’t be an entrepreneur. You are able to mitigate some of that risk by being a business owner instead of an entrepreneur, for example opening a franchise which has a higher rate of success. If you’re looking for certainty, you’re not going to find it in your own business. 

Who should be an entrepreneur?

Creative thinkers and risk takers are the people who should be entrepreneurs. There is a lot of risk and opportunity cost in building a business and you need to be okay with taking that on. 

If you’re driven by necessity you are going to have much more motivation to push through the difficult times and figure out solutions to complicated problems that can keep a business running.

Why a side hustle instead doing something BIG?

Troy compares a side hustle to a rocket ship launch. It’s not just about keeping a side hustle, it’s about building something that you know will be big eventually, something that replaces your full time job in time and is worth investing in.

For Troy, it’s not about having a second part time job to make some extra money. It’s about building something that can make a big impact over time.

What is the self assessment?

Being an entrepreneur is like climbing Mount Everest, it’s not something you do on a casual whim. You need to be mentally and physically prepared for both endeavors and take stock of your temperament and if being an entrepreneur is really for you. Troy spends just as much time talking people out of being an entrepreneur as he does strategizing how to launch their side hustle. 

Even if you think you’re unprepared, there is a point where you need to stop reading and start doing.

Reference: How to Launch Your Side Hustle: Start and Scale a Business with Minimal Capital, Troy Underwood

Troy’s Takeaway

You have to be all in and make sure you also have your partner’s buy in as well. There will be bad days and having a support system is very important. Remember that the downsides are more likely than the upsides and if your family isn’t on board with your idea, it’s going to be a struggle. Your mindset and the mindset of the people around you is going to be more responsible for your success or failure than how smart you are.


How To Launch Your Side Hustle

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