Land Guests with the Help of Their Heroes

5 minutes

Holloway Editione1.1.1

Updated September 14, 2022
Stop Asking Questions

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It can be hard to persuade guests to do interviews. So I call on stories of their heroes to help me like I did the time I wanted to interview a writer who was at the center of a scandal.

I used to check TechCrunch the first thing after waking up. I wanted to see what was new in the startup world that I loved. One Friday morning, I woke up and read that a TechCrunch writer, Daniel Brusilovsky, “allegedly asked for a Macbook Air in exchange for a post about a startup.”

I emailed Daniel about doing an interview. He told me he was a big fan but couldn’t do it. The news just broke. It was too soon.

I could understand the embarrassment of being called out by the tech press, including VentureBeat, Gawker, Silicon Valley Watcher, and Huffington Post. I wanted to reassure him that he shouldn’t view this scandal as a reputation killer—that sharing his side of the story in an interview could actually help him.

Daniel was a startup junkie like me. He respected entrepreneurs who took risks and bounced back from failures. Instead of pleading with him to do the interview, I emailed him this:

The entrepreneurs you admire have done some crazy stuff in the past. Here’s a line from Richard Branson’s Wikipedia.

“In 1971, Branson was arrested and charged for selling records in Virgin stores that had been declared export stock.”

A few minutes later, he agreed to a phone call. Then he agreed to do an interview with me.

Stories like Branson’s arrest are iconic—almost startup folklore at this point. The more common stories I share come from guests I previously interviewed. If a founder raised money from Y Combinator, I might tell them about how the founders of Y Combinator did my podcast, and I’ll mention a few other startups who raised money from them. If a potential guest is an investor, I might reference my past guest David Rubenstein, founder of the Carlyle Group.

Referencing the heroes of your potential guest is a powerful form of social proof. But when I first started Mixergy, I didn’t have enough well-known guests on my show. People I interviewed, like Zappos founder Tony Hsieh, were successful but not yet well known. I needed to find a way to get interviews with instantly recognizable people.

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Conference organizers know that industry celebrities draw large crowds. Those speakers were the type of heroes that would be perfect for helping me recruit interviewees.

I decided to go to startup conferences and seek out these well-known speakers. I would attend their keynotes and wait for them to get off stage. Then I’d ask them, “Can I interview you right now?” After grabbing their attention (and typically overwhelming them), I would dial back my request and say I just wanted to ask a few quick questions. They still weren’t enthused to do it, but asking a couple of questions seemed reasonable compared to an entire interview, so many of them agreed. This is how I got interviews with Tim Ferriss, influential blogger Brian Clark, and Apple co-founder Steve Wozniak.

These recordings didn’t set the world on fire. Tim’s lasted only 39 seconds, and Steve’s consisted of him telling a joke about Steve Jobs. Still, these short interviews gave me social proof and allowed me to show off my interviewing skills. In some ways, the short clips worked better because potential guests just wanted a quick understanding of who I was.

When I reach out to founders I want to interview, I usually send just a three-line message. For many years, this was my pitch:

Can I interview you on Monday at 9:00 a.m., Pacific about how you built your business?

This is for, where I interview founders about how they built their businesses.

You can see a sample of my style in these short interviews with Tim Ferriss (link), Brian Clark (link), and Steve Wozniak (link).

Over time, as I landed higher-profile guests on my main show, I replaced these short interviews with lengthier ones.

People want to emulate their role models and heroes. You can use this desire to land interview guests. But if you’re low on potential guests to contact, you need to start thinking like a salesperson. That’s next.

Listen: Role Model

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