From Epic Failure to Multi-Millionaire with Serial Entrepreneur Ian Ippolito – Episode 79

Today’s episode we talk to Ian Ippolito who shares how he went from a major epic fail with his first software startup to building an $11.1 million company ($135 million in total revenue) that he eventually sold (for an undisclosed price in the millions) to in November 2012. 

Phil and I are the luckiest people on earth getting to sit down every week to Google chat with some of the bravest and most interesting people. Entrepreneurs and small business owners like Ian who have seen major success but still feel fear every day.

[FYI: The video went out from track time 5:44 to 6:15.]


Watch the show (uncensored & unedited)
Listen to the podcast

Share Some Shut Up Love –> I realized it wasn’t just a failure. I did a lot of things wrong I could change. So I tried again. – @IppoDude on #shutupshow (click to tweet)

Fun Facts:

  • Ian is a serial high tech company founder, CEO and entrepreneur.
  • Ian has been featured in Entrepreneur Magazine’s “100 Smartest, Most Innovative and Brilliant Companies”.
  • Ian was awarded Inc. 5000 “Fastest Growing Private Companies in the U.S.” award four years in a row.
  • Ian has been interviewed by Wall Street Journal, Business Week, Forbes, TIME, Fast Company, CBS News, and FOX news.
  • Ian attended Marquette University for Electrical Engineering, which is located a couple miles from Phil’s office in Milwaukee, Wisconsin.
  • Ian’s company vWorker was acquired by Freelancer in November 2012 for an undisclosed price in the millions.

Defining Shut Up Moment:

ON RISING ABOVE HIS FIRST EPIC STARTUP FAIL: I wanted to work for myself at a very young age. When I got out of college, I went to work for someone else but always looking for something on the side. I wanted to build a software company so I spent months creating a piece of software and nobody bought it. Not one. I spent months creating it thinking it was going to be this whole wonderful thing. But I learned some really great lessons from it. I didn’t now what I was doing. I didn’t do any market research to find out if anybody wanted to buy it. I didn’t talk to any customers. I built what I thought was the coolest thing and no one agreed with me. That was one of my first big lessons about how important it is to get out of my brain and get out into the real world. A lot of times there’s a disconnect there and it’s necessary to bridge those things in order to be successful.

ON NOT GIVING UP ON BEING AN ENTREPRENEUR: I always worked for other people but it was always a source of frustration because I would go to work and give ideas but nothing would ever get done. Even though I had failed, I wasn’t happy with the way things were at my job. I was feeling the daily frustration of where I was. I did a lot of things wrong I could change so I tried again. A few projects later, my Rent A Coder business saw moderate success and I ran out of space in my spare bedroom. So I decided to find office space to rent.  I had to sign a lease of 5 years, which meant even if your company fails you’re still on the hook for paying the rent. It scared me to death having to make the payment but I saw the company was on the trajectory to do well so I took a calculated risk, I signed that lease and we moved in. We grew so quickly we outgrew that lease and the next. Fast forward 12 years, I sold the company (vWorker) to Freelancer.

Shut Up Tips:

“Fall down 7 times, Stand up 8.” – Chinese Proverb (via Ian)

Every morning I’d wake up, I was excited to be working on something where I was helping people all over the world who’d never have the opportunity to work. – Ian

I would prefer the business to not be the central focal point of my life, but many times it has to be. It was a lot like having a baby. There were times when the baby was sick and things were broken that need to be addressed. – Ian

People think the ideal of selling a business is I didn’t have to work. What I discovered is I like working. It gives me purpose. It gives me passion and makes my life better. – Ian

The fear does never stop and it’s perfectly normal to have some fear. Just because you’re successful or you’ve done it before doesn’t mean it feels any different than it did the first time. – Phil

Ian Recommends:

Ian will announce his new business and upcoming projects at

Find Ian:

Tweet Ian at @IppoDude