Carl interviews Doug Villhard, a former software company president and co-founder, entrepreneur, investor, philanthropist, author and now a professor teaching entrepreneurship at the Olin Business School at Washington University in St. Louis. Doug was only 49 when he and his partner sold their company for $30 million. He had started his side-hustle--teaching--years earlier and is very happy in his new career. He has 400 students each year, full of bright ideas and eager to learn how to create, launch and manage their own companies. "I teach them to continue to be curious and look for problems to solve in life and work. I encourage students to innovate and take risks." Doug is also the author of the recently published Company of Women, a fictional story based on the life of E.G. Lewis.

Doug grew up in a family of five in St. Peters, Mo. His mother was a teacher with very high academic standards and his father was an engineer. "I thought you were supposed to get straight A's and listen to your parents. I didn't know there was any other path!" Doug tells us. "I was a little Eddie Haskell-ish--good with adults and a little mischievous behind the scenes."

After college, in 1995 Doug landed a job with Disney Interactive in their online division. He says he loved that job and learned a lot. Years later, when he was married with a child on the way, took a job with the St. Louis Post Dispatch in St. Louis, working on their website. where he met Matt Coen, his future business partner. Doug ran various software companies and then Doug and Matt co-founded Second Street Media in 2007.

At Second Street, they focused on how to draw big audiences and then create layers of products and services around them. (Hint: Kids and pets are huge!) "Second Street is where I really learned to listen to the customer. It's the whole trick to being successful in business." (Full disclosure: Carl worked with Second Street for about a year and sold his company to them.) Carl talks about how much he admired the company culture at Second Street. Doug says, "I don't know how you can be successful without a great team behind you."

Jawdropper: When their kids were in school, the nearest Catholic high school was 45 minutes away. So with no blueprint (the last school was founded 80 years earlier) Doug and his wife Diane actually founded a Catholic high school in their area. "It was 1400 families--a whole community came together, " Doug adds.

Since Doug had already started teaching entrepreneurship at Washington University before the company was sold, he easily transitioned to his full-time second act "Teachers get summers and holidays and breaks, so for me there is still time to travel with my wife", (you'll have to listen to the podcast to hear about their unique travel strategy), Doug tells us. "And I just wrote a fictional book based on E.G. Lewis, the biggest magazine publisher in the world in 1904. He was a huge proponent of women's right to vote."

Doug Villhard's 7 Tips on Being a Successful Entrepreneur for Your Second Act:

• All businesses solve a problem.

• Keep listening to your customers.

• You have to be selfless for it to work.

• Ask yourself: Are the customers happy? Are your employees happy? Are your loved ones happy?

• Getting involved with younger people is invigorating and broadens your perspective.

• Never before has it been so easy to have a side-hustle. There are so many ways to put your toe in the water!

• Don't sit around trying to make the Second Act perfect. It's impossible. Just run some experiments and try little things until you find what you want.

• More about Doug Villard -- Book Author, Professor, Investor

• Sponsored by How to Retire and Not Die

• Sponsored by Capital Advantage

Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the “I Used to Be Somebody” blog.

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