‘Never Work for Someone Else’: Lessons in Start-Ups

Born in the Philippines and raised in New Jersey, Arabella Santiago has an innate ability to connect with people from all walks of life. She put her people skills to use as a reporter before moving into the tech space, where she’s worked in front of and behind the camera for ventures like StartupLive, a network of entrepreneur-focused videos that she co-founded in 2011.

Our paths first crossed at a news publication way back in 2000, when people actually used fax machines and desk phones. We recently caught up, after Santiago successfully produced this year’s Techweek Chicago event, to discuss start-ups, leadership, and women in tech.

Arabella Santiago

Between Techweek and your work at StartupLive, you clearly love and value the start-up experience. What makes it so appealing?

I find start-ups so fascinating because they epitomize the “American Dream.” The opportunity to create something out of nothing that can change the world, or even just a niche industry, is exciting. Thanks to technological advancements, starting and building a new business requires minimal overhead. And I think that’s just plain beautiful.

What’s something you learned during one of your StartupLive interviews that resonated with you?

One of my most eye-opening interviews was with Hiten Shah, co-founder of Kissmetrics. During the interview, he told me that his father told him never to work for someone else. I love learning about the lives of these start-up founders and what enabled them to become such successful people and entrepreneurs.

At the end of the interview, we went offline and Hiten asked me more about StartupLive. When I told him we were creating shows about start-ups, he suggested a different approach to our content gathering. My co-founder, Suzanne Debrunner, and I thanked Hiten for his advice and have since implemented the idea.

What do you think is the most important component of a start-up?

A solid founder. With strong leadership, an idea can survive many iterations. With bad leadership, you can get lucky that the business will work because of market need, etc., but you will certainly drain resources and compromise team morale. Smart and successful founders know how to rally a team behind them through thick and thin.

What’s one idea, experience, or encounter that has really stuck with you from Techweek?

I found that in Chicago, people are hungry for different ways to become part of the start-up culture. Non-techy people are enrolling in classes at Code Academy, where beginners can learn programming and software development. And a new co-working space called 1871 recently opened up its doors to Chicago start-ups at the Merchandise Mart. I believe that this is just the beginning.

Screenshot of Santiago's network of entrepreneur-focused videos, Startup Live

There was some criticism about the fact that the 2012 Techweek 100 list included just eight women. You took to Facebook to defend the list, but you also noted that the industry has “a lot more work to do.” Are you confident that things are moving in the right direction?

I think that there are leaders in this community that have taken an active role, investing in start-ups founded by women and minorities. For example, Dave McClure and his team at 500 Startups have invested with diversity in mind. In Chicago, I met a lot of entrepreneurial women, but many of them led more “lifestyle” businesses, which usually do not attract VCs [venture capitalists]. I stand by my statement that there’s a lot of work to do in supporting women-owned start-ups. Even if people like Dave McClure are making great waves in supporting this movement, we need more people like him out there.

As far as the Techweek 100 list goes, research shows that only 3.2% of 3,049 publicly traded companies have women CEOs. Placing more women on the Techweek 100 list does not solve the problem. What solves the problem of having more high-achieving women in start-ups and technology is giving them more resources and investing in them.

For more on Arabella Santiago and her work, check out StartupLive or follow Santiago on Twitter and Facebook.

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