Tim Guleri

Tim Guleri is a former serial entrepreneur, having built two successful software infrastructure companies: Scopus Technology (IPO in 1995) and Octane Software (M&A – Epiphany $3.2 billion). He joined Sierra Ventures as Managing Director in 2001, focusing on Big Data and Artificial Intelligence. Since joining, he has taken two companies public (Sourcefire – $FIRE, and MakeMyTrip – $MMYT) and has been responsible for several M&As.

Tim holds a BA in Electrical Engineering from PEC University of Technology (India) and an MS in IEOR/Robotics from Virginia Tech. His passion (outside of his family and companies) is soccer.

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Insights from Tim

Where does your resilience come from?

My dad was in the Indian Army, in the infantry, so life was hard growing up. He had this phrase: box on. When a boxer goes down, the referee asks if he can continue. Box on. You get up and you keep going.

That came back to me at Virginia Tech. I lost my scholarship one term. Instead of calling my dad for money, I went to Sacramento and sold books door to door, earned about twelve thousand dollars, and paid my own tuition for the next quarter. Adversity happens. You pick yourself up and keep going. That job led to my first entrepreneurial role, and everything after.

You have to be good at your craft. But once you have some liftoff, you go back to your core as an individual. What makes you you.

Can entrepreneurship be learned, or are you born with it?

It can be learned. Nobody talked business at my dinner table growing up. I had no exposure to it at all.

What changed things was California in the early nineties. Every conversation at the water cooler or at a friend's house on the weekend was about entrepreneur X who built company Y and did great. That is the remarkable thing about America. The can-do is in the water. You just have to reach for it.

At some point I looked at my own skill set and thought, I can be the guy they're talking about in the third person. That lit the fire. I was in my twenties, through grad school, already working. You are not born with it. It gets switched on.

What do you do outside of investing, and has any of it changed how you think about backing founders?

Racing vintage cars is one of my hobbies. Ours is a 1928 Bentley Bobtail, from an era when Bentleys were the fastest and most advanced cars on the road. We don't just run it around a track. I have competed in several multi-week endurance rallies, including the Peking to Paris, roughly 15,000 kilometers across Eurasia. There is no pit crew. The route crosses the Gobi Desert, rugged steppes, high-altitude mountain tracks, and back roads through multiple countries. Something breaks every day, and you fix it on the side of the road with whatever you brought with you.

It reminds me of being an operator. I built two startups from the ground up, and the pattern is the same. A new obstacle every morning, solved with grit, ingenuity, and heart. Most days are not glamorous. You learn to enjoy the journey anyway.