Overcome Any Problem

8 minutes

Holloway Editione1.1.1

Updated September 14, 2022
Stop Asking Questions

You’re reading an excerpt of Stop Asking Questions, by Andrew Warner, a veteran podcast host of 2000+ episodes. The book explains how to lead high-impact interviews and learn anything from anyone. Master the craft of interviewing with this complete digital package. Purchase now for lifetime access to the book and extensive audio and video resources.

A few years back, I decided to try something brand new.

I was going to conduct in-person interviews … in Estonia. It would be part of my larger goal of running a marathon and conducting an interview on every continent.

My hosts in Estonia were LIFT99, a community of successful tech startup founders, who invited me to record in their office. As I set up, my mind flooded with the worries of a rookie. I had ten years of interviewing experience by then, but the wildly unfamiliar environment had me nervous. I was recording in person, using new and unfamiliar equipment. What if my microphones and recorder failed? What if I didn’t know enough about the people I was interviewing? What if they regretted giving up time with their families to record with me on the weekend?

Sitting in the conference room they lent me for the day, I tried to think of anything other than my nerves. If I didn’t, I was sure to make a mistake setting up my new equipment or fall back on excessively flattering questions in an effort to be liked. I thought back to my first interviews to remember how I handled anxiety back then. What got me through the early days was focusing on my higher purpose.

I started Mixergy after a massive failure. I poured $300K of my own money into an online invitation site that was so bad that my wife would not even use it. After the company went under, interviewing became my way to learn how other founders built their companies. I wanted to figure out how I could do it better next time. I wanted to remember what was fun about entrepreneurship. And I wanted to provide all that to other entrepreneurs.

Those first recordings were horrendous. I didn’t know how to use an equalizer, so fans had to lower the volume to hear me stammer through questions and raise it when my guests responded. But I didn’t let those mistakes stop me because I needed my guests’ insights. I was desperate. I was on a mission.

Years later, when I asked fans why they listened despite the audio issues, they said they needed those answers too. They were on similar missions.

So that’s what I did in Estonia. I reminded myself what brought me there. It all started when I looked for an old note on my computer and discovered a list of ten-year goals instead. I felt like a failure when I read it. Ten years were nearly up, and I hadn’t achieved any of them. Even though I misplaced the list, those unmet goals lived somewhere in the back of my mind, haunting me.

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I was in Estonia because I decided to start with the goal that excited me most: run a marathon on every continent. I also decided to interview founders on every continent about how they reached their goals. Then I’d find a way to do the rest of the things on the list.

So when I was nervous or worried about the equipment, I shifted my focus to my mission: achieve my ten-year goals.

My trip paid off when I interviewed Ahti Heinla, the Estonian co-creator of Skype. He told me how Skype was built and sold to eBay for $2.6B. Focusing on the weight of my unaccomplished goals, I kept my nerves in check. I asked him how he reached his next goal. He saw how important this conversation was to me and confessed he didn’t hit it.

“Everybody who was early at Skype, and founded another startup after Skype, failed,” he said. “It was a hard landing for everybody.”

I could imagine how tough it was. My failure to hit my ten-year goals was private. His failure was public.

My equipment worries disappeared as I asked what he did next. He told me he stopped trying to build a mega-successful startup. He was going to have a daughter and so decided to take a break. As a hobby, he built robots and entered them in robot battles. That’s when a thought occurred to him. His robots were getting so sophisticated—what if they could be used to deliver food? He launched a new startup, Starship Technologies. Soon colleges signed up to use them for food deliveries on campus. The startup grew. By not trying so hard, Ahti achieved more.

The next day, I sat with my iPad in what felt like an old Soviet coffee shop, and I went through my list of goals again. I realized I didn’t really care about most of them. One of the biggest items on the list was to grow my online invitation site. I had closed that business years ago. Interviewing became my business, and I loved it so much more than running that invitation site. So I decided to liberate myself from the demands of that list. I was free to enjoy life and pursue new interests.

To get to that realization, I had to tune out everything else and focus on my mission.

It’s not just inner chatter that you need to tune out—audience expectations and ratings can distract you from your mission as well. The hosts of the All-In podcast learned this lesson the hard way when they covered the Robinhood vs. Gamestop debacle in early 2021.

The show is hosted by four famous investors who talk about tech, startups, politics, and life. They pride themselves on giving no-BS takes on the biggest issues of the day. When Robinhood, the stock-trading app, halted trades of Gamestop during a massive short-squeeze, the internet erupted with outrage. This was the type of newsworthy story that the All-In pod feasted on. The hosts landed an interview with Robinhood’s founder, Vlad Tenev, to feed the audience’s appetite.

The result? The All-In pod momentarily became the most popular tech podcast in the U.S. and 11th overall on Apple Podcasts. But it nearly destroyed the show in the process.

The hosts felt like they couldn’t be harsh with Tenev because their audience expected them to support entrepreneurs. At the same time, they couldn’t go easy on him for shutting down trading because their audience also expected them to hold leaders accountable. The result was a lukewarm interview that neither pushed Tenev nor satisfied the audience.

Co-host Jason Calacanis said fans of the show “barbecued” them. Another host, David Friedberg, thought the pandering interview was so bad that he threatened to quit. As co-host Chamath Palihapitiya said in a postmortem, “We got caught up a little too much in ratings: ‘Where is it ranking?’ ‘How can we go higher?’ And it’s that gamification of people’s reactions that caused us to do that.”

Whether you’re worried, nervous, or just excited, the way to center yourself as an interviewer is to focus on the mission. What is your higher purpose? For me, that mission is to learn how to be a better entrepreneur and let my audience learn along with me. What is yours?

Listen: Get Back to Purpose

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