21 Questions with Mike Troiano / CMO, Actifio

If for no other reason than that his bio blurb reads "Italian kid from RI, NY ad man, Boston entrepreneur. Lyrical gangsta.", you should know Mike Troiano. Follow him on Twitter and read his Tumblr. Maybe he'll even tell you what happened with Rhonda DeStephano...

Easily one of the most inspiring people I've met in the Boston marketing / technology / innovation economy, Mike is a frequent contributing writer on marketing, entrepreneurship, and social media, and is ranked in the top 1% of the most influential people on  Twitter. He serves as a  TechStars  mentor (like me), and as an advisor to some of the more interesting Boston startups. Currently the CMO at Actifio, a venture-funded technology startup outside Boston, Mike spent his early career at top advertising agencies including McCann-Erickson and Foote, Cone & Belding, and became the founding CEO of Ogilvy & Mather Interactive in 1995. Mike co-founded New York-based strategic Internet services firm Brandscape in 1996, and merged it with NASDAQ-listed systems integrator Primix Solutions, where he became president. After the sale of Primix in 2002 he joined venture-funded mobile content pioneer m-Qube, serving as a member of the executive team until the company was bought by VeriSign in one of the largest Boston-based venture capital exits of 2006. He was the CEO of Kraft Group-funded matchmine, a distributed media discovery platform, and then a Principal of Holland-Mark, a Boston-based strategic marketing firm. Mike is a graduate of Cornell University, and the Harvard Business School.

1. What would the headline of your biography be? 

"Italian kid from RI, NY ad man, Boston entrepreneur." Also my Twitter blurb.

2. What is your mission / goal in life?

To connect to the truth. I think in the long run, all the pain in life is caused by distance from the truth... of ourselves, what we need, our relationships, products, markets, whatever. Life is a struggle to get closer to the truth, I think. I guess that's my goal.

3. What do you love to do?

Cook for good friends. Something primal in that, I think. But there's nothing better than an evening making and enjoying good food and good conversation with good friends.

4. What were your “aha” moments - when you realized you were exceptional at something?

I think the first was in middle school. I wrote a comedy skit that really cracked up Rhonda DeStephano, and that after that, she seemed to like me more. I remember thinking, "Hmm. Power in that." Second was beating out Tommy Centore to win Outstanding Senior in high school. That was a big moment for me. I remember it in slow motion. Third was probably getting invited to join the new business team at McCann in NY. After that, my HBS acceptance letter. There were speeches, moments, other stuff later. But those are the big ones.

5. What keeps you up at night?

The stresses of family. With four kids, somebody's always in some kind of crisis. My mom told me once, "You're only as happy as your unhappiest child." She was right.

6. What historical / business figure do you most identify with?

I'm not sure about that, but the one I most aspire to is Churchill. I have tremendous respect for his resolve, his sensitivity, his understanding of people and how to move them. He did all that while quietly overcoming his own challenges. A truly great man. I try to be more like him.

7. What is the trait you most want to improve in yourself?

I'd like to get back in shape. It's a lifelong struggle, really. Right now I'm losing.

8. What are your unique talents?

I have 3. Empathy, to understand what people feel. Pattern recognition, to find clarity in the complex. And synthesis, to combine ideas in ways that create something new. That's about it.

9. What is your greatest extravagance?

Great restaurants. I'm a foodie. I think even a lot of money spent on those experience, with people you enjoy, is well spent.

10. Which brands / businesses do you admire the most?

Apple, of course. I really admire the Patriots organization, and the way Robert and Jonathan have built that franchise. And probably BMW, for their ability to balance unchanging values with cutting edge technology and design.

11. Which words or phrases do you most overuse?

"When everything is a priority, nothing is a priority."

"It's not hard, people."

"Fuck."

12. What is your greatest career regret?

I left McCann in a way that hurt my relationship with my mentor, Craig Middleton, and Ogilvy in a way that hurt my relationship with Martin Sorrell. Same mistake, both times because I was recklessly ambitious. But I never made it again.

13. When or where were you happiest in life?

Senior year of college. Top of the food chain, at the peak of your personal powers, surrounded by the friends of your lifetime. So many options, so few responsibilities. I love my family, my work, and my life now... but it's harder for me to experience that kind of happiness, without that kind of freedom.

14. Which talent would you most like to have?

I'd like to be able to play the piano.

15. What do you consider your greatest achievement?

To this point it's probably getting through HBS. But I think in the long run it will have been my role in making Actifio successful.

16. What is your most treasured business memento?

I won the first ever trophy from the Mobile Marketing Association. We were trying to create an industry back then, and needed something sexy to show it could work. We convinced Warner Bros. to let us do something for Terminator 3, and I designed and wrote the whole thing in a couple of days. It was really groundbreaking stuff, and I was really proud to have gotten the deal, and delivered the creative. Still have that trophy in my study.

17. What do you regard as the lowest depth of misery?

Accountability without control. Stresses. Me. Out.

18. Do you care about money?

Yes. It buys you freedom. And cool stuff.

19. What is your defining characteristic?

Probably that I'm an emotional person. It can be a feature or a bug. I've gotten better at managing it, but it is who I am.

20. Who are your favorite business writers / bloggers / people?

I'm kind of over the whole business book thing. I've read so many, and even the best ones boil down to a single truly great insight or idea. There's more to be learned in great storytelling I think. Tolkien, Scorcese, David Simon. I really respect those guys, for their understanding of human nature.

21. Who is your hero in real life?

Springsteen. He's an artist. The talent, courage, and character it's taken to get to where he is and stay there for as long as he has is just awesome. He's a hero to me, for his work and the way he's lived his life.

Though this photo is b/w, Mike speaks + thinks in full technicolor.