I Hold Posters to Meet Billionaires at Sun Valley. What I’ve Learned.

This as-told-to essay is based on a conversation with Dushime Gashugi, who has attended the annual Allen & Co. Sun Valley Conference several years ago to seek advice and business opportunities from the event’s billionaire attendees. It’s been edited for length and clarity.

In 2014, my first small business tanked, and my mentor from college died. I just kind of felt lost. I thought, I need to go find people, I need to find the best. So, what’s the best conference in the world?

In the first few years I went, from 2015 to 2017, I made a list of the CEOs I wanted to meet. I’d say, “Hi, my name’s Dushime. I’m an entrepreneur, and I flew here to ask you about your habits of success. Do you have a moment?”

Those first three years I went, it was about building my Rolodex and finding mentors in different areas. I wanted to find the best people in the world at building teams, raising money, scaling, all those things. I thought, I’m just going to swing for the fences; no one else is out here doing this.

Meeting people and lessons learned

Back then, the security wasn’t like it is now. You could literally be on the premises and talk to 20, 25 people in a day. I’ve sat and talked with some people for like 15, 20 minutes before. It was just open. I stayed in an Airbnb on the property, and there were a lot of open areas, cafés, so if they were walking, I’d just stop them on the sidewalk.

I met Jeff Bezos that way. I stopped him to introduce myself; he shook my hand and said, “Hey, I’d love to chat, but I have to run to a meeting.” He saw me carrying a book and said it was one of his favorites and that he’d try to catch me later. It was the kindest, “I’m busy and I’ve got to go.” He was still very present, complimentary, and really nice.

I’ve also met other well-known people, such as NBA commissioner Adam Silver, Kering CEO François-Henri Pinault, and Disney CEO Bob Iger.

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I was banned from being on-premises in 2016, so in 2017, I started holding up signs, since I couldn’t get as close to the action. I didn’t anticipate the publicity; that was just as close as I could get.

Bloomberg actually did call me later, saying he and Gates had been told about my sign.

My biggest surprise across the board was just how present everyone was. You think, “Why would they talk to you? They’re busy.” But the people I spoke with had a really great skill of making you feel like you were an important person. That’s not necessarily advice they gave me, but something that made me say, “Man, I see why you’re really successful.” If you make people who you don’t need feel like this, imagine how effective you’d be if you treated people you do need in the same way.

Going to space?

In later years, I started thinking, “Okay, it’s cool to meet these people, but how do I creatively think about a situation where we can do business together?” There was no other time when all these people were in the same place.

I live in California and used to work in real estate, but then pivoted into insurance.

I thought, “Who’s the biggest guy in California?” At the time, it was Elon Musk. He’s talked about wanting to build colonies on Mars and die there.

Bezos is also focusing on space with Blue Origin and has talked about a vision of a trillion people living in the solar system.

I said to myself, “Listen, I’m not smart enough to figure out space, but someone’s going to have to the real estate and insurance for that. I can be that guy; I just want to sell their real estate and insurance.”

So in 2021, I came back wearing a spacesuit and a sign targeting Bezos; the rental alone was like $1,500.

In 2022, I couldn’t come, so I paid like $5,500 for a company to fly a plane with a banner for two hours to try to get Musk’s and Bezos’ attention. But it was so high up in the air people couldn’t read it, so it didn’t work that well.

Whether we make it to space or not is fine with me. In real estate, in most sales businesses, if you’re not the first or the second person people think about, you basically don’t exist. I’m trying to get to a point where if you think insurance, if you think anything real estate, the first person you think about is me.

Trip logistics

When I go to Sun Valley, I usually go Tuesday through Thursday. Roughly, each trip might cost me $2,500, including gas, food, and incidentals.

It’s like 13 hours each way by car, but I drive because my signs are too big to be carry-ons if I were to fly, and I don’t want them to get damaged before I arrive.

But the more recent trips have cost me like $800 to $1,000; over time, locals started recognizing me, so the last two times, people reached out offering to let me stay with them. Sun Valley has become kind of a second home of sorts for me because people get used to you. They say, “Oh, the astronaut man’s back. Welcome home.”