Eric Simone, Cup 67 Coffee WIth A Stranger

Cup 67: Eric Simone – Risk taker, family man and shy introvert.

Eric Simone, Cup 67 Coffee WIth A Stranger

The Place: Second Bar and Kitchen

The Cup: We opted for a lunch meeting – so iced tea was our coffee equivalent.

Background: Cup 52, Brett Hurt suggested Eric as great guy with a terrific story who would be perfect for the project. He made an email introduction and once summer vacations were behind us, we were at last able to get together.

Brett was spot on – Eric is indeed terrific, and his insights on life and business were fresh and surprising. We’ll get to his story in just a bit, but first, let’s cover some:

Common Ground:

  1. What’s a food you can’t live without? Pizza
  2. If you could swap lives with someone for a day, who would you pick? Patrick Kane from the Blackhawks on the day they won the Stanley Cup. (Eric was in Boston and saw that game live.)
  3. How did you make your first buck? Washing dishes in a pizza place.
  4. What’s your favorite way to unwind? Besides going to the gym, it’s doing silly stuff with my kids. Like going to see “Cloudy With a Chance of Meatballs”, or playing Minecraft on the Xbox.
  5. What is the last thing you fixed? I just installed a Nest thermostat. It was was easy enough.
  6. What’s the best place to eat in Austin?  Uchiko 
  7. What was your favorite TV show as a kidMASH – a unique combination of humor and war.
  8. What is your guilty pleasure? Gambling – pro sports.
  9. What is the best gift you ever got? My wife threw a football party for me the Sunday after our wedding. It was great – all my friends were there in their jerseys watching the game, before we left for our honeymoon.
  10. What is your best feature? The ability to take a risk. To believe either in myself or in someone else. That makes me a very open investor. Also a somewhat dangerous investor, because sometimes I believe too hard.  But it’s gotten me where I am today. If I hadn’t been a risk taker, I’d still be working at IBM, or running the same business I was running.

After graduating from Purdue University with a Computer Science degree, Eric jumped right in with the big dogs when he was hired on as a programmer at IBM. He spent several years programming – both at IBM, and later at Johns Hopkins Hospital, and then had the chance to move back to his home state of Illinois, and back to IBM, for an opportunity that would stretch him beyond his technical skills. His new role was part technical, part sales. It turned out, Eric was one of the rare individuals who excelled at both. And when I say excelled, I mean he was a rock star sales guy – winning awards for being a top performer. (Being somewhat modest, Eric didn’t actually tell me that, but a quick glance over his LinkedIn profile revealed this tidbit.)

Only a few years into his professional resume, and Eric was already on his way toward a promising career at IBM. So you might imagine everyone’s surprise when the 27-year-old decided to take a huge risk – leave IBM and start his own company. In hindsight, he says that while it felt risky at the time, he now looks back and realizes he really didn’t have anything to lose.

At a time when most everyone around him was staring at him with jaws dropped, wondering what on earth he was thinking leaving his stable career and leaping off into the unknown, he found an unlikely champion who offered up what Eric cites as the best advice he ever got.

During an exit interview with his second-line boss, Eric found himself a little nervous as he waited to hear the same message he’d heard from everyone else, “You’ve got a great future here at IBM…” and he prepared to defend his decision. Instead of the same old company line, Eric’s boss said, “I think what you’re doing is really exciting and I think you’ll be really successful with it. You’ve had a great career here at IBM and guess what? If it doesn’t work out, you’ll find another job here if you want it. Go do it!” Eric says, “Those words helped me take a big risk. He basically said, ‘Don’t be afraid. Go after it!'”

Eric did go after it. And he found big success. The company he started in 1994 went from one employee to 80 by 1999. In 2000, he got a call from Perficient, an Austin company who’d been keeping on eye on the business and had decided they’d like to buy it. In 2000, Eric’s company, Compete, Inc., was bought by Perficient (PRFT:Nasdaq) for $63M. He moved to Austin and stayed on until 2003, when as Eric says, “It was time for a new challenge.”

A gifted programmer turns out to be a stellar sales guy, who then turns out to have huge talents in starting, running and growing companies. So what was next? Well, fashion of course!

Actually, I’m serious. Well, sort of.

When I asked Eric about his greatest achievement to date, he said, “It was finding the right partner. I can’t imagine doing the things I do without my wife’s support. It’s the one thing I got most right in my life.” After moving around the country for his business, Eric said, “It was time to help my wife do her thing. It was her turn.”

Eric’s wife Toni had a career in fashion before the couple left San Francisco for Austin, TX. In 2003, Eric, Toni and friend Koshla started a women’s upscale fashion boutique called “Girl Next Door”. Eric left the fashion to the experts, but did lend his start-up expertise to the business and handled operations for the store until, once again, he was ready for a new challenge. Since 2007, when Eric left to start another company, Girl Next Door  has been run exclusively by Toni and Koshla. If you haven’t been there, it’s time to check it out.

ClearBlade, an enterprise mobile software and services company which launched in 2007, is Eric’s most recent successful start-up. Fortunately for many other local budding entrepreneurs, Eric is also a passionate investor. In fact, that’s how he and Brett first met one another. Brett had an idea that would eventually be called Bazaarvoice. He and Eric were neighbors, and Eric assures me the fact that he was an early investor in the company that would become one of Austin’s biggest success stories and best investments has nothing at all to do with his ability to spot a winner. It was Brett’s unassuming persistence which caused Eric to eventually write the check. That, and a really great idea. But without that persistence, Eric would have continued to turn Brett down.

What might we be surprised to learn about Eric? He says, “I’m really shy. I overcompensate by being open. I trust people more when they are open and I find it breaks down the shyness. I give a lot of information and that helps me connect with people.”

The most significant thing that’s happened for Eric in the last 30 days was his youngest son heading off to kindergarten. Eric tells me, “I’ve never seen a kid more ready to be socially involved. He walked in and on day one, he was Mr. Popular. Unlike his dad, but very much like his grandfather.” I asked Eric how dad handled the first day of school and he admits, since this is his second, he wasn’t at all worried like he was with his first. He was just excited for him.

Eric spends most of his life in a state of fearlessness. From racing cars to starting businesses, he doesn’t let worry get in his way. When I ask where this comes from, he suggests it may be from seeing his dad start a business at a less than optimal time – when Eric was just a year or so from heading off to college. His dad had spent his career in insurance, and when Eric was in high school, his dad left and started his own company. It was this example, coupled with an innate drive within himself. Eric says, “I was always the introverted underdog, and I overcompensated by taking big risks and placing big bets. Sometime I failed, but it worked out over the long run. We could spend an hour just talking about the failures.”

I press him on this topic of failure because I’ve had a few conversations lately about the shame that keeps people from talking about the “f” word. Eric tells me, “Failure is just part of the game. Sometimes the story changes, and it’s like it was perfect the whole time. I would like more honesty in terms of, ‘Here’s what we didn’t do well, here’s where we ran into a rough time.’ The press tends to look for the interesting story.” And details like hard work, missed opportunities, or bad choices just get glossed over and don’t make the final edit. We want the happy ending, but the fact is, failures are as much a part of the success story as the victories.

Want to get better at failing? Eric shares the surprising way he got more comfortable with it. He and a friend spent a year doing improv at The Hideout. Wow, that’s brave! I’m eager to shake off the perfectionism cloak too, but not sure I’m ready for failing in front of a live audience. Eric says, “It was one of the best things I ever did because it taught me it’s okay to fail. They teach you if something isn’t going well on stage, you accept it, you own it and you take a big bow. They call it ‘failing fantastically’. It’s okay to fail and in business, you need to let your people know it’s okay for them to fail too. It’s like saying, ‘I’m not perfect. And I don’t expect you to be either.'”

If happiness were the national currency, I want to know how Eric would make his living. He tells me, “I’d do the same thing. I’m lucky enough to not be doing this for the money. I enjoy the challenge. The least happy I’ve ever been in life is when I’ve been successful but not challenged. I was just coasting. When I coast, I get restless. I have a constant drive to be challenged. And sometimes it gets tough and I have to remind myself, ‘You asked for this.’ I feel blessed and lucky. I have a great family. A great wife. Great kids. My wife is running a clothing business and I’m happy doing start-ups and investing. I wouldn’t change any of it.”

OK, there is one thing he’d change – it’s the thing he’d change about himself if he could. Eric says he’d be more patient and tolerant. The drive he has within him is great for getting things done, but he says he’d like to be more even-keeled. Eric’s wife helps balance him. He says she’s “calm and steady”.

What is something Eric believed to be true for a long time, but now knows differently? He says, “I used to think that we were more a function of our experiences than our genetics, but realize now we’re more influenced by our genetics than I believed. My father passed away a few years ago and when I see friends of his they tell me ‘You’re just like your dad.’ We like to believe we’re more in control than we actually are.”

If given 30 seconds to make a speech to the world, Eric would have this to say: “There are so many people who just mark time. They don’t change things when they’re unhappy. For those people I’d say, ‘Go do something completely different. Find your passion. If you don’t know what you’re passionate about, go help people.’ I just came across something I wrote a few years back that said, ‘I don’t want to look back five years from now and say, ‘I wish I had done that.’ I know many brilliant people who are just staying the course. There are times when you need to shake things up.”

This meeting couldn’t have come at a better time for me. Eric’s message, while not exactly what I wanted to hear, it totally what I needed to hear.

Are you taking chances? Risking? Betting big? I’m not. My preference is to play it safe and for me, taking chances only happens when the odds are stacked heavily in my favor. I spend far too long ‘getting ready for success’ and am terrified of making a mistake and looking like a fool. Failure is my second to worst nightmare. Second only to not succeeding. I know, those sound like the same thing, right? Trust me when I tell you, they are not.

Not failing – that’s good stuff. But not nearly as amazing as succeeding. In order to experience the thrill of victory, I know I have to take a few chances. Meeting with Eric was like a shot of truth straight to the heart. I’m playing small. As much as it pains me to admit, I know it’s the truth and it’s time to shake things up.

Eric offers a powerful reminder to all of us, that failure is just a part of life. It’s going to happen. So when it does, embrace it, take a bow and fail fantastically. Then get up and move on.

Merely staying the course – coasting – that’s not living. What are you not doing right this minute that in one, five or ten years you’ll look back and wish you had? The truth is, that time’s going to pass whether you do the thing or not – so go do it! And encourage the dreams of others. Help other people achieve their dreams. Like Eric’s boss at IBM, you never know the lasting impact your words may have. So why not shine a light on everyone?

Finally, Eric’s story is a reminder that while the destination matters, what matters even more is choosing the right companions for the journey. Surround yourself with the right people who encourage you, inspire you, love you and believe in you. There’s an African proverb that says, “If you want to go fast, go alone. If you want to go far, go together.” Find your people and go for it – together!

6 thoughts on “Cup 67: Eric Simone – Risk taker, family man and shy introvert.

  1. I love this! I have some friends who just started improv classes to help boost their creativity, so his words on failure connected with me. I’m sending this to them!

    1. Wow! I’m truly in awe of anyone brave enough to do Improv. Which means it’s probably THE thing I most need to do. Thanks for stopping by for sharing!

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