Entrepreneur Educator, Program Developer, Facilitator

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How to shoot your shot with an important person 

How I met Tim Ferriss, AOL Founder Steve Case, and San Antonio Spurs owner Red McCombs

It’s 2009 at a party during the SXSW tech conference in Austin. Tim Ferriss, author and angel investor riding high off of the success of the Four Hour Work Week, is in conversation with a conference attendee in the middle of the venue. I am a bright-eyed first-time founder with puppy dog energy, desperate for capital and connections. Landing Tim as an investor would give my startup both. Despite my nerves, I know I should approach him.

But he’s locked in a conversation. How do I break through for a chat without coming off like a pushy used car salesman? Barging into the conversation like a savage would lay a bad foundation for a big ask.

And what if Tim’s conversation partner is making their big ask. I can’t stand the idea of robbing someone else of an opportunity. Forcing myself into their conversation might throw them off their game.

I wish I’d known the move that I know now. After dozens of failed attempts with investors, customers, and internet thinkers, I figured out an approach that worked reliably. The approach I outline below has given me access to people such as Malcolm Gladwell, AOL founder Steve Case, and San Antonio Spurs owner Red McCombs. 

The process involves only two steps: establish your position and create a connection.

Establish your position

When the two people are in conversation, place yourself opposite the important person so you are behind their conversation partner but in the line of sight. Imagine a clock where the important person is at the center. If you’re at the 11:00 or 1:00 clock position, facing them, they will note that you have queued yourself to interact with them. 

Here’s a visual depiction:

Make eye contact to signal to the important person you are interested in a chat. Be non-threatening. If you’re a 6’1” and 220 lbs, soften your face and make frequent glances at your target in between occasional glances at your phone; sneaking the occasional peek reminds them of your intent much better than unwavering eye contact (socially skilled people call staring).

Place yourself a couple of feet behind the person they are talking to; you need to be close enough so that person can register you in their peripherals, so they are aware that you are next in line.

Eventually, the non-important person will peel away. Now your window is open.

I sat and waited at that party for what felt like years for Tim to wrap up that conversation. When it ended, I exploded into Tim’s field of view and burst into his personal space. I’m sure it caught him off guard. To his credit, Tim gave me his full attention and heard me out—something he didn’t need to do.

 He then graciously turned me down. 

Create a connection 

I was missing an important part of the process: creating a connection.

Before you launch into why your startup deserves their funding or why they should hire you, remember that you are a human being connecting with another human being. 

Important people who show up in public spaces get flooded with asks and pitches. Their experience of the world is like that of a lottery winner or a supermodel—everyone wants something from them. (Why don’t we hear more about this? Because no one likes to hear about successful people’s problems. Tim Ferriss is one of the few who has written about the downsides of fame.)

If you can sincerely, authentically offer one word of kindness to them before you make your ask, you are recognizing their humanity. You are signaling that they are worthy of genuine connection, something that well-known people often lack.

If they are a writer, mention something super-specific you loved about a piece they wrote. If they are responsible for a product you love, mention something about a feature you appreciate that only a real user would know.

BAD“I love [x], it’s so great”
GOOD“When you talked about [super specific thing] in [x], it changed how I think about [topic]”  “The way you and your team designed [x] saves me hours a week”

I was at a conference where I spotted Steve Case. Case is a billionaire best known for founding AOL (America Online), the company that got more Americans on the internet than anyone else in the 90s and 00s.

When I struck up a conversation with him, I never mentioned AOL. Not once. Instead, I opened with some kinds words about the book he had just written about growing entrepreneurship in the overlooked parts of the United States. 

He responded with warmth and appreciation. Why?

Well, everyone likes kind words. But in Steve’s case, for the rest of his life, he will be known as the guy who founded AOL. Which is pretty cool…the first thousand times. Decades later, a person moves on and has new passions and priorities. Trust me, Led Zeppelin got tired of playing Stairway to Heaven. 

By acknowledging his new work, I was doing him a kindness. Thanks to that, he gave me his email, and one week later I was speaking to his head of programs (the people who buy entrepreneurship programs, which is what my company does).

So that’s it. When you find yourself out and about and you see someone who could change your trajectory, shooting your shot is simple. All you need to do is establish your position and create a connection. 

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Thanks to early readers: Dave Shepherd, Justine Jones