Sunny Gupta, CEO and Co-Founder of Apptio

We’re continuing our build-up to GeekWire Startup Day — taking place Sept. 22 at Meydenbauer Center in Bellevue— with videos from some of the notable presenters from past years. Today, we’re going back into the archive to 2010, featuring Apptio’s Sunny Gupta and his insights on what it takes to raise venture capital.

Gupta is a pro when it comes to raising money, having raised more than $100 million for both Apptio, and his past company iConclude. (You probably saw our past coverage Apptio’s recent $50 million round here).

One thing that stands out about Gupta is that he’s not afraid to swing for the fences, though it hasn’t always been easy for he entrepreneur, as we learn in this video.

Here are a few key takeaways from his talk:

On making the leap: “I wanted to figure out a way to not incrementally grow my career, but really do a drastic, dramatic leap in my career. And, I felt like the only way I could do that was if I took control of my own destiny and started my own business.”

On taking venture money? “Sometimes the opportunity is so big and the market moves at such a fast pace, that if you’re trying to do it organically, you won’t achieve the same style of outcome.  But I’ll also be the first one to say that venture (capital) is not for every style of business…. My philosophy is ‘you go big or go home’ and venture capital really helps you scale to that level.”

Planning to make the startup plunge, or already in the deep end? Don’t miss Startup Day 2012 — Saturday Sept. 22 in Bellevue, as Box CEO Aaron Levie and other startup vets help you find your roadmap to success. Details and tickets here. Early bird rates end Aug. 12.

Be sure to have a great team: “(Have) an incredible team that is complimentary, I can’t say enough about that.  Especially when I got in front of the venture community, everybody asked me: “Hey, what’s your team?” And, I was like: “Hey, why are they asking me about the team? I will make this happen. ‘ Over time, I realized that it’s so critical to have the team, especially a complimentary team.”

Be capital efficient: “Even though you have venture money, the philosophy I’ve always taken is every dollar invested in the business demands a return.  From that perspective, we were hugely capital efficient.  We only spent $1 million even though we had enough money in the bank, and I think that discipline from a venture perspective is really, really important.  The early rounds of venture capital are extremely expensive to the founders because you’re giving up a big part of the company.”

Raise money while you can: “The obvious question is why did we raise so much money (at Apptio)?  Our belief is that this is a pretty big market opportunity and we may end up running into a rainy day.  When you can raise money on good terms, raise as much as you can.”

Look for more talks from the Startup Day archives in the coming weeks, and make sure to join us Sept. 22 for Startup Day 2012 before the early-bird rates expire.

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