Recently I had the privilege of sitting on a panel with two extremely successful serial entrepreneurs, Sam Yagan (founder of OkCupid and now CEO of Match.com) and Chuck Templeton (founder of OpenTable and now managing director of the ImpactEngine accelerator at 1871). The event was moderated by Rob Wolcott, who runs the Kellogg Innovation Network (KIN), and the official title of the panel was longer than most of my blog posts, so let's just sum it up as "an evening of quips and networking tips from a bunch of very smart and experienced people." I laughed a lot (and learned a few things as well). Here are a couple of the highlights.
1. Walk the walk (and wear the t-shirt)
I'm usually the most under-dressed guy at grown-up events like this, but Sam Yagan was wearing a Match.com t-shirt under his jacket so, from a sartorial standpoint, it was pretty much a draw. The more important point was what Sam said about why he was wearing the shirt, and what wearing the shirt says about Sam. He said that, as the CEO, he's always selling and promoting the business and that it's a critical part of that process that everyone he meets realizes that he's all-in, fully committed, and sincerely believes that Match.com will change your life for the better--and, if you've got the time, he'll tell you how and why.
My friend Slava Rubin, who co-founded Indiegogo (and is now the CEO), always wears a company t-shirt when he travels. He's also plenty proud of the business he's built and it shows the minute you meet him (also, you'll miss your plane if he starts talking about the company and the latest and greatest crowd-funding successes they've helped make happen). He says, of course, that his shirt's a comfy way to roll, but the real reason is that he knows he's going to pass a bunch of people on the trip and it's the cheapest form of subliminal advertising he's come up with so far.
But this is also all about authenticity--believing in your business and yourself and walking the walk. Leaders lead by example or they don't really lead at all. The day you're not comfortable in your role, in the business, or in the company t-shirt is the day you should find another place to be. If you're not excited about what you're doing, and proud of the place you doing it, do something else. This stuff (building new businesses and changing the world) is just too hard and life's too short to go to work every day without a spring in your step and a smile on your face. Not everything will be fun and easy, but as long as it matters and you're making a difference, there's no better place to be.
2. You Never Know Who's Going to Bring You Your Future
Rob Wolcott likes to say that at KIN he tries to never leave serendipity to chance, and Chuck Templeton described two specific ways that, in the early days of his business, he manufactured his own serendipity. One was a process and one was an attitude; both helped him build his earliest networks of supporters and sponsors, and, crucially, helped him fill in gaps in his knowledge and experience.
The process was pretty simple. He'd read every issue of The Industry Standard, which was, for a brief time, the hot tech-industry magazine. When he read about people doing things that seemed interesting and relevant to his business, he would reach out to them and ask them for a few minutes of their time to answer his questions. Not only did he learn a lot about stuff, but he said that he also learned a lot about how many people were so generous with their time and how they would actually take the time to help a total stranger. The moral of the story was pretty simple: It never hurts to ask. Often, in fact, it turns into a real opportunity, and it's always an education.
The attitude part was also pretty straightforward. He said that you should always keep an open mind when you meet people and never underestimate them, because you just never know who's going to turn out to have the keys to the kingdom. Or, as I like to say, you never know who's going to bring you your future. Every encounter, every meeting, every conversation is a chance to learn--and to build and extend your network. Everyone's an example of one kind or another, either to emulate or to avoid like the plague. But you'll never know which ones are which if you don't invest the time to explore the possibilities and have the right attitude while you're at it.