‘Learn how to walk the high wire’

9/1/2015 - Gil Penchina has failed in epic fashion, and not just once.

“This is the life of an entrepreneur,” Penchina told the incoming Class of 2017 during the second day of the school’s Complete Immersion in Management (CIM) Week. “Silicon Valley is a town full of people who are failing all the time.”

But failure, he countered, is often the path to success. And as the keynote speaker of the weeklong orientation for new students, Penchina talked about his time during and after Kellogg while advising the incoming class on how they could best use their time in Evanston.

Looks can be deceiving

Penchina’s name might be familiar to some; he’s listed on Kellogg’s LinkedIn page as one of the school’s most notable alumni. When coupled with his impressive resume, "it looks like I just walked straight up the ladder,” he said. “Behind the scenes, it was not such a pretty view.”

While at Kellogg, Penchina landed a coveted summer internship with a well-known consulting company. Though he was “too impatient” to do the job, he expected a full-time offer.

“Basically everyone who gets a summer internship from that employer gets a full time job, except me,” he said. “It was humiliating. I didn’t want to admit I wasn’t a good consultant.”

Still, Penchina spent two more years in consulting before heading to eBay. Over the next eight years, he worked his way up from Manager of Business Development to General Manager, International. He then went on to become the CEO of Wikia in 2006, a successful collaborative website inspired by Wikipedia.

Learning and trying

Penchina now leads what’s known as a syndicate, a curated group of investors who support emerging businesses through crowdfunding. The investors depend on his expertise — as well as his contacts — to find and invest in attractive startups.

Penchina, in turn, gets 15 percent from any investment profits eventually earned by the group, which is built from the online investor platform AngelList. Past successes include investing early in the aforementioned LinkedIn, Paypal and Cafe.com. Currently, Penchina’s syndicate is the largest of its kind, with Penchina leading more than 2,000 backers and more than $6 million in funding.

While he’s had many successes, Penchina says he’s not done failing yet. The difference now is that Penchina isn’t bothered by it. “I look at it as I’m learning, I’m trying,” he said.

‘The chance to learn anything’

Penchina advised Kellogg students to dabble in areas outside of their comfort zone. For example, Penchina took an HTML class at Kellogg — which he wasn’t sure he would like — and started writing pages of content about how to get airline miles, of which he had accumulated more than a million.

Subscribers to his e-newsletter paid $15 to join. By his second year at Kellogg, his online business had generated $80,000.

His advice to the Class of 2017: Take weird classes, but maybe with a little more of a focus.

“Kellogg is a safety net, so you might as well learn how to walk the high wire,” he said. “It’s a great opportunity we have at this school, which is giving you a chance to learn anything.”

And when they find something they like, Penchina said, go after it. “Once you find something where the universe gives you the permission to be awesome, jump in.”


Related reading:

• The Class of 2017 arrives at Kellogg