"I'm still super insecure in many ways, but I'm also happy to say that I'm super insecure."

My favorite activity is: Snowboarding Something people don't know about me: I can rotate my legs and feet to point 180 degrees behind me. It’s freaky.

Ben Elowitz

Advising CEOs and founders with a sense of compassion

OFFERING A FRESH PERSPECTIVE. A long-time entrepreneur and investor with a rich portfolio of experience that extends over 26 years, Ben Elowitz is now using his expertise to help other CEOs and management teams on their most strategic challenges. "Throughout my career, I've been involved in over 70 startup fundraises. My specialty is ensuring companies are well-positioned to be successful at these defining events. To do that, it's about seeing things from a 360-degree view of not only what the entrepreneur sees, but also what the investors see."

Ben's entrepreneurial career began, unbeknown to him at the time, at the age of 14, selling cans of Coca-Cola out of his locker to classmates and soon after, software products via adverts in the back of PC Magazine. During high school and college, he worked as a software engineer, doing consulting work for projects at A&M Records and Kaiser Permanente before landing an internship at Microsoft.

After being encouraged by a friend to expand his career options, Ben took on a role at the management consulting firm Bain & Company. The experience shifted his perspective on business, and was a launching pad into the startup world in 1996. The first company he joined, pioneering e-commerce platform Fatbrain.com, was an early success, going public within two years.

In 1999, Ben co-founded online jewelry retailer Blue Nile. From the company's "exhilarating" early days to its post-dot-com boom years, he says the experience was "invaluable at helping me understand what it means to be out of favor in the sector and what it means to be sure you're building business fundamentals as you go."

Among Ben's many success stories since then is Wetpaint, a TV and entertainment web platform that marked his first time being a CEO. It was another experience that proved pivotal in informing his advisory work today. "I felt the pressure of having all the decisions on me. I think if I'd appreciated sooner that my job isn't to have all the answers but rather to motivate others, acquire resources, and make the best decisions possible with an appreciation they're not going to be perfect, my experience there would have been a lot easier."

A SENSE OF PRIDE. Work has been an anchor throughout Ben's life, especially during his twenties, before he came out as gay. "Before I was out, my work was the thing that gave me a sense of self and self-worth. I found that because I’d worked in a world with this huge avenue for success, where I felt a sense of achievement and had respect for who I was, that when it came to my startup, I was ready to come out because I felt secure in myself."

Ben has been grateful to have been guided by several mentors throughout his career, but the best advice he continues to hold on to is "'be compassionate to yourself. CEO and founder jobs have so much pressure on them, and you have to take on every responsibility in the company's decision-making. If you recognize and appreciate that you're not necessarily qualified for everything you do, you can go to your team, advisors, and board and have much more honest conversations with them.

"I'm still super insecure in many ways, but I'm also happy that I am comfortable enough to say that I'm super insecure. There's a whole bunch of stuff I know and feel pretty confident about, but boy, there's so much stuff I don't know. To be able to live with both of those at the same time, with a sense of compassion, I think, is really powerful."

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Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.