Holloway Editione1.1.1
Holloway Editione1.1.1
Updated September 14, 2022To Olivia, who has embraced my curious spirit since our first date.
This book and the interviews it’s based on couldn’t have happened without the support, mentorship, and hard work of the people who helped me through it all.
Without the Damn Gravity Media team, this book wouldn’t have been as good and hardly anyone would have known about it. I’m especially grateful to Ben Putano, the founder, who has talked with me practically every weekday since we started working together. Thank you for spending hours at your laptop telling people about my book and pushing me to stop being shy about promoting it. I don’t know how you could be such a calm, encouraging coach with all the work you have on your plate. Thank you.
John Hernandez, thanks for turning the ideas in this book into content that spreads. My Twitter account never had as much action before you.
To the Holloway team—especially Joshua Levy and editor Carolyn Turgeon—thank you for helping me turn this book into something much more—an interactive digital resource for interviewers and conversationalists.
Thank you, Seth Godin and Tim Ferriss, for being some of my earliest guests. For years, every single one of my interview requests included a line about how you two did interviews with me. You helped me land great interviewees.
Paul Graham and Jessica Livingston, thank you for letting me promote my early interviews on Hacker News and introducing me to Y Combinator founders to interview. Your community created a solid foundation for me to build mine on.
Jason Fried, when I started charging for my interviews it felt like a world of criticism hit me online. Your supportive message kept me from backing down and helped me turn interviewing from a passion project to a business.
Jeremy Kareken, thank you for analyzing my interview transcripts with me in the hunt for the perfect questions and helping me realize that asking questions isn’t the only way to get answers.
Noah Kagan, thanks for introducing me to your seemingly infinite number of friends. How do you know so many people?!
Neil Patel, when my site wasn’t optimized and you got tired of telling me how to fix it, you took my username and password and fixed it yourself. Thanks for always being the person I could trust with my private information and jumping in to help so many times.
Arie Desormeaux, I once learned about a friend and interview guest who cried during their pre-interview with you. He thanked me for finding a producer who was so good at tapping into old memories. When I asked you why you didn’t tell me about this, you said it happens too often to tell me every time. You have a gift for conversations. I’m lucky to have you at my side, shaping the stories we publish on Mixergy.
Andrea Schumann, you started out taking on small tasks at Mixergy and were always so good at your work. Over the years, you’ve done every job at the company. Thank you for keeping the company going and being someone I could count on.
Sachit Gupta, thanks for seeing our revenue and saying, “Andrew, you can do better.” Then taking on the work of growing that revenue.
To the producers who’ve worked on Mixergy, you were responsible for preparing Silicon Valley’s top founders to tell their stories and building an audience to hear them. Thank you, Giang Biscan, David Saint, AnneMarie Ward, Brian Benson, Tristan De Montebello, Joe Garcia, Rebecca Lay, Adrian Palma, Tam Pham, and Megan Johnson.
Jeremy Weisz, I used to get frustrated when you told me after each interview, “Yeah, but let’s see how it could have been better,” and “We need to talk every week.” I thought I didn’t have time. I’m glad you pushed me to make time.
Thank you, Michael and Marisela Khalili, for running Mixergy better than I ever could.
Bob Hiler, on our weekly calls you helped me understand that I needed to put a proper structure behind the loose collection of habits that formed Mixergy. The podcast couldn’t have grown without you, and neither could I.
Rachel Kersten, you always had a better sense of the business side of content creation than I did. Thank you for professionalizing it.
Listeners who listened to my podcast over the years heard me mention several times that I was writing a book, but I could never sit down long enough to actually finish it. Then COVID-19 hit and Robbie Abed asked me to write a chapter for his book. He then encouraged me to keep writing and introduced me to people who could help. Thank you, Robbie.
Merry Sun, this book wouldn’t have been finished if you hadn’t gotten on calls with me every week to check on my progress, give me feedback, and guide me. Thank you for not quitting on me on all those times I said I needed to stop writing.
Ryan Holiday, I wanted support when I told you this book was too much work and I wanted to hire a ghostwriter. Thanks for giving me tough love instead. Writing it myself was the tougher, but better, approach.
Thank you, Taylor Jacobson and everyone at Focusmate. Whenever I needed to stay focused on writing, I’d start a session and instantly have a stranger to keep me going remotely via webcam on my phone.
To Chemda of the Keith and the Girl podcast, for showing me how powerful podcasts can be by sending me photos of fans with your logo tattooed on them.
To Mom and Dad. When my grade school teachers complained to you that I was a jack-in-the-box who couldn’t sit still in class, instead of telling me I had to sit down, you asked the teachers if they’d allow me to have a desk in the back of their classes so my occasional need to stand up wouldn’t disturb the other students. Thanks for always showing me that I don’t have to accept the rules.
Thank you, River and Shepard, for being interested in the endless stories I tell at the dinner table about the amazing people I meet at work. And for always asking, “Can I do that?” Yes, you can do all of that. And more.
Finally, thank you, Olivia, my wife and soulmate, for always being patient when I use my interview skills to meet new people wherever we go. And for supporting me as I made one last attempt to write this book on that gorgeous dining room table you bought us. I love you.
Billionaires turned to finance legend Alan “Ace” Greenberg for advice. He ran the Wall Street firm Bear Stearns at its prime. I was an unpaid college intern and wanted to learn from his experience. So I asked for a meeting and hoped he’d agree to the type of connection that could change my life. He said he wanted to help ambitious employees like me, so he set aside time for us to talk.
I walked in to see him, holding a notebook full of research I did based on obscure articles and conversations with people who followed his career. He sat at the end of a giant table he shared with dozens of his employees, most of whom seemed to be talking on two phones at once. It was loud, but his eyes and attention were only on me, eager to help. That’s when it hit me. I didn’t know how to access any of his wisdom.
I asked him about his start. He told me how he sat next to the firm’s chairman and slowly took on more of the man’s work until he was the firm’s leader. I had already read that in an old Forbes article. So I asked what makes someone successful. He told me that instead of an MBA, he likes people with a PSD, which stood for “poor, smart, and a desire to be rich.” I had read that in an old BusinessWeek article.
He was warm and attentive, but I couldn’t figure out how to go deeper and learn anything new. Finally, he stood up and ended our mutual discomfort. Shaking my hand to indicate it was time for me to leave, he said, “A fella once told me, ‘If you’re doing what you enjoy, you never have to work a day in your life.’ I hope that quote helps you.”
I knew I’d missed a golden opportunity, but I wasn’t sure what I’d done wrong. It was my one shot to tap into Ace Greenberg’s wisdom, and all I got were facts I’d read before and some canned advice I could have found on my college bulletin board.
Today, we all have a world of opportunities to have conversations with people who could change our lives. Anyone with a computer or phone can record an interview, learn from people they admire, and share it with the world. Interview podcasts democratized access to these conversations. YouTube allows anyone with a camera to distribute their video interviews instantly. Blogging offers a place for text-based interviews. I’ve even seen one-minute interviews on TikTok gain hundreds of thousands of views. New online platforms are popping up constantly.
Offline opportunities are growing too. Conferences, meetups, and other events use interviews as an alternative to the traditional presentation.
Let’s be real, though. Most of these interviews are simply insipid content thrown together by people who don’t know how to tap into someone’s greatness. I don’t blame the interviewers. Nobody taught any of us this new craft.
Until the 1900s, publishing interviews was virtually unheard of. It was an ingredient in good journalism but hardly ever the finished product. Late-night TV talk show hosts were the ones who popularized the interview format. They needed an easy way for celebrities to shine without roping them into skits or other elaborate performances. From there, interview-based news shows became the work of serious journalists, who made their reputations by getting politicians and other newsmakers to reveal shocking information.
It was never my goal to create “gotcha” moments in interviews. I wanted to learn from people I admired—my heroes. I was desperate to improve.
Even though I graduated with a degree in finance, I didn’t end up working in a bank or investment firm. I fell in love with entrepreneurship and started an online greeting card site that did over $30M in revenue. After selling it and taking a few years off, I came back to the startup life with an online invitation site. It completely bombed. It was so bad that even my wife refused to use it when she threw me a birthday party. I blew $300K on the business, but what really hurt was that I didn’t know why I’d failed. I couldn’t move forward with my business life until I knew how I could do better next time.
I became obsessed with interviewing after that second company failed. I sought out conversations with successful founders I admired to understand how to build a better business. I wasn’t just hanging out with my guests. I was determined to use my interviews to become a better entrepreneur—a better me.
Unexpectedly, interviewing became my business. I started a podcast interviewing proven tech startup entrepreneurs like the founders of Airbnb, Dropbox, and Y Combinator. In each interview, I learned a bit more about how to run a company, including growing an audience, systemizing operations, and hiring. That grew into Mixergy, a site for ambitious entrepreneurs.
Other entrepreneurs were equally eager to learn how to build a better company. As they showed up to listen to my episodes, advertisers bought ads to reach them. My interviews got so good that fans paid to listen to them and take my master classes.
Over the course of ten years, I interviewed more than two thousand people I admired. No one ever taught me how to interview, but I seized the opportunity behind every conversation by studying the hell out of the questions I asked and the responses I got.
In the years that followed, I spent $38,188 to have my interviews transcribed. Then I hired producers and coaches to go over my conversations to help find patterns in the responses. If a technique worked, I added it to a doc so I could keep reusing it. When something didn’t work, I deconstructed it to understand how I should have done it better. The improved version went into the doc.
I realize now what was missing when I talked with Ace. I wanted to learn, and he wanted to teach, but that desire is not enough. Interviewing is more than just asking questions. It takes skill to help someone teach what we want to understand—skills I’ve spent thousands of hours learning to master. The doc I created organized the skills I’d accumulated through interviewing. I’m sharing them with you so you can improve your podcast or in-person interviews, or simply have better conversations with people you care about.
This book is organized into four parts, following the order I’ve used when teaching new interviewers over the years. I noticed people first want quick, actionable techniques. So Part I is full of conversation tips you can master quickly and use for the rest of your life, in both interviews and daily conversations.
Once I give you the quick wins, you’ll probably want to do the deeper, harder work of learning how to prepare for and structure an interview. So that’s Part II. Then, when you have your skills nailed, you’ll be eager to land your ideal interviewees. Part III focuses on how to identify good guests and convince them to sit for an interview. Finally, Part IV will give you the fundamental aspects of the business side of interviewing. If you can’t make interviewing profitable, it’ll be harder to make it sustainable.
As I mentioned, this format is based on how others I worked with preferred to learn. If you have different preferences, feel free to jump around. Just avoid limiting yourself to what you think you need. Conversations are unpredictable.
caution One final piece of advice: Don’t be rigid. You can’t force each of these techniques into a conversation. Use them as guides, but don’t be obsessed with using them perfectly. I don’t. You’re about to get to know and learn from your heroes. Enjoy it.
This Holloway Edition includes additional exclusive digital content. You will get more out of this book by hearing actual conversations with the author.
When reading online, throughout this book you will find audio clips selected to illustrate different conversational techniques.
Also included is a three-part podcasting tutorial, presented in conversation with the author, plus additional resources for that course.
Details are at the end of the book.
In this first part, I’ll fire you up with quick wins. These are conversation superpowers that you can master quickly. They’ll get you past the toughest parts of your interviews, but they’ll also work in non-interview conversations like dinners, parties, and meetings.
They’re so fun and effective that they feel like party tricks. Using them is an easily mastered way of leveling up your interviews in the short term. In the next part, I’ll cover how to make interviews meaningful and interesting.
A roadmap of the techniques covered. Graphic is available for download and may be shared freely, with attribution to Andrew Warner and Holloway.
Timothy Sykes was at it again.
Looking at him through my webcam, I could see the winning smile of a man who expected to get the better of any conversation.
I asked him about his work ethic, and he managed to turn it into a pitch. “I have a DVD called Penny Stocking where I teach people … And not surprisingly, my real-time stock trade alert service is fifty times more popular than this DVD that would actually teach them to do it on their own.”
I asked him how he started blogging. “Wall Street Warriors,” he said. “It’s a hit TV show now in fourteen countries, so I was in that show, in five to six episodes of season one.” Then he artfully mentioned his book, telling me, “People were emailing me what they wanted to know. So I wrote a book called An American Hedge Fund.”
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🎤 With Timothy Sykes: “How A Self-Promoting Blogger Makes $1.3 Mil A Year And Still Gets No Respect.”
🎤 With Adam Jackson: “Braintrust Guts the Marketplace Model.”
I wasn’t being a jerk when I pushed Jason Fried to tell me about his failures. I acknowledged and admired how he bootstrapped Basecamp into a project management tool that was bringing in millions of dollars a year in profits.
Still, I wanted to hear about his failures. I learn a lot about growing a business by understanding how people overcome failures. But if I’m honest, I was also hoping to see that he was like me: a human being with failures I could relate to.
So I pushed. And pushed. And pushed. Finally, he looked right at his webcam—on a video call, the closest thing to looking someone in the eye—and told me that it’s not helpful to even think about failures or look back.
Years later, when I hired Jeremy Kareken, an interview coach, I brought up this interview as an example of a big problem I have. In conversations, pushing harder for a goal often leads me further away from the goal.
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🎤 With Jason Fried: “Bootstrapping Lessons From 37 Signals.”
🎤 With Jason Fried: “Hey.com’s founder reinvents email & battles Apple.”
A few years ago, I had several guests over for dinner.
We all sat around my living room, waiting for the last guest to arrive.
Finally, as he came in, he said, “Sorry I’m late, everybody. When you go through a divorce, everything takes longer, like finding your daughter’s sweater. Plus, traffic is getting rough in this city.”
One of the other guests said, “I know what you mean about traffic. As the tech industry grows, people keep piling into San Francisco and causing congestion everywhere.”
After I sold my greeting card company, I moved to Santa Monica and took a few years off work to focus on personal development.
One of the best things I did was go to weekly Toastmasters* meetings to become a better speaker. I was still new there when one of the members invited us all to her house for drinks.
For the first hour, the conversation was stilted, limited to whether our cars could make it to the top of Bear Mountain without snow chains. Elena, one of the other guests, said: “I don’t know if it could make it up a mountain, but I know it could go across the country. After my sister committed suicide, I put all my things in the backseat and drove till I got to California. It didn’t give me any trouble on the way over. I’ve had it for seven years, and it’s always held up.”
Someone asked what type of car it was. By then I already knew how to spot a shoved fact, and how it’s a signal that someone is eager to talk about a topic. So after she answered that she had a Ford Bronco, I asked a more meaningful follow-up.
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🎤 With Robert LoCascio: “LivePerson: From A Founder’s Most Painful Moment In Business To $100 MM / Year.”
🎬 With Pablo Fuentes: “A founder faces pivoting or failure (8 separate times).”
After I started writing this book, I offered one-on-one coaching sessions with new interviewers to ensure I was addressing their real needs. Over and over, I saw that one of their biggest challenges was curbing excessive promotion. In the “What’s a Win for You?” section, I addressed how to show a guest you understand their need for promotion. But when is the right time to finally help them promote?
In most cases, the answer is when you’re interested in what they’re promoting and when you think your audience would be curious about it. So if you’re interviewing an author of a new book you enjoy, absolutely start by asking about it.
But if the promotion has nothing to do with why you’re talking to them, wait until the end, when you and your audience are emotionally connected to the guest. That’s how it’s been done on television for years. When I was a kid, if Robert De Niro was doing a late-night interview, it wasn’t because he enjoyed wincing through questions about his childhood. He had a new movie to promote. The deal was he’d give the interviewer a little peek into his life so fans like me could get to know one of our favorite actors. In return, the host’s job was to help De Niro promote his latest movie.
I found that it’s best to clarify the agenda with guests before we start recording by using a promotion stopper. I get their buy-in by phrasing it as a question, like, “Of course I’ll mention your new project in my intro, but since my audience isn’t emotionally connected to it yet, do you mind if we build your credibility first by talking about the big company you sold?”
Have you ever met someone who seems so perfect that they feel fake? I was starting to feel that way in my interview with Taro Fukuyama. So I wanted him to tell me about something that didn’t go well.
I asked if Fond, the employee reward company he launched (previously called AnyPerk), had hit its first million dollars.
“More than that,” he shot back.
Well, how about the customers? He started listing blue chip brands that signed up with him: Virgin America, Salesforce, Cushman & Wakefield. Then he explained that they were just the tip of the iceberg.
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Even if you listened to each of my 2,000-plus interviews, you would probably miss my best question. That’s because it’s my shortest question. Ironically, it’s also a question I stole from Charlie Rose.
Rose’s iconic interview show lasted for a quarter century on PBS. But critics initially hated it because he asked questions that were longer than his guests’ answers. It became so bad that Rose’s long-windedness was parodied on Saturday Night Live. In the skit, Rose (played by Jeff Richards) interviewed Donald Rumsfeld (Darrell Hammond) and droned on for so long that Rumsfeld erupted, “I think you just spent ten minutes asking me a question, but I have no idea what it is!” Finally, Rumsfeld walked off as Rose continued to struggle to explain what he’s trying to ask.
I totally relate to Rose. There’s so much I’m trying to cram into each question. I want people to go deeper and also know that I’m giving them a safe space to do it. I want to understand their motivation and tell them why I care. Sometimes I just get lost in my own sentences and can’t find a way out.
But Rose kept improving. By the time I started interviewing, he was so smooth that everyone from Bruce Springsteen to Bill Gates appeared on his show. Business leaders paid him more than $50K to come to their corporate events and interview them onstage. They weren’t paying for Charlie Rose per se, but for his ability to help them express themselves better than they could on their own.
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Over the years, I’ve been known to host events called Scotch Night at my office, where I invite a few Mixergy listeners to join me for a drink and conversation. I remember one particular evening well. Sitting on tall chairs around a long table, few paid attention to the variety of Scotch bottles I put out. It was all about the conversation. Each founder was eager to hear what was working at other companies, so the group was boisterous.
After an hour, a founder that the group called “College” (because he was still in school and not old enough to drink) asked, “Andrew, do you ever have a guest who won’t say anything about their financials? How do you get them to be so open?” Everyone quieted down. As information hunters, it was something they also wanted to learn.
“Yeah,” I said. “A few days ago, Shradha Agarwal, founder of ContextMedia, which does health videos for waiting rooms, wouldn’t tell me anything about her revenue. I wasn’t trying to pry—I just needed a sense of how big her company was so the audience could understand what we were talking about. She wouldn’t give me anything.”
“What’d you do?” he asked.
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🎬 With Shradha Agarwal: “ContextMedia: How One Female Entrepreneur Is Killing It.”
When Gregg Spiridellis sat down for an interview with me, I had a sense he wasn’t sure why he even agreed to do it. His production company, JibJab, was cranking out viral video after viral video. He’d even been featured on The Today Show. I wouldn’t blame him for feeling odd about sitting in front of a webcam with someone he had never met as a favor to a friend whom I had interviewed a few days before.
“It’s a challenging day,” he told me when I asked how he was doing. How could I get his best effort when there was so much pulling at his attention?
Gregg was running one of the hottest content brands in the country. ABC News named him and his co-founder People of the Year because their video, “This Land,” went viral with a message of unity at a politically divisive time. Meanwhile, my podcast hadn’t yet broken the 100-download barrier.
When I doubt myself, I remind myself of my mission. I want to get the true stories of how founders built their companies. I sensed that telling Gregg my vision in a way that showed him the benefit of participating would get him engaged.
🎬 With Gregg Spiridellis: “The JibJab Story. Maybe The Most Inspiring Mixergy Interview Ever!.”
🎬 With Nikki Durkin: “How 99dresses failed (with three cofounders, funding, and a mentor).”
🎬 With Marcus Weller: “Skully founder opens up about failure (and tells me what he learned).”
Most people think an interviewer’s job is to ask questions. I can tell you from experience that it’s not.
I learned this at a hilltop house in Los Angeles overlooking the ocean. While my friend Steve and I had a beer by his pool, I asked him what he did to earn such a gorgeous place.
“We’ve known each other a long time because our wives are friends,” I said. “But I never asked you about your business. What do you do, Steve?”
He said he made apps. I saw a quick smile come across his face, so I followed up with, “How’d you get started?”
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🎬 With Rod Drury: “The Entrepreneur Who Sold 3 Companies.”
🎤 With Sara Rodell: “Addressing customer gifting at scale.”
I grew up in New York City, so I prefer to be blunt and ask for what I want. But as an interviewer, if I don’t take some of the sting out of my questions, my guest could become defensive, stop paying attention, and maybe even walk off.
A good example of this comes from a BBC interview with conservative commentator Ben Shapiro. The video went viral because he stormed out before it was over. I had the interview transcribed so I could study it and understand what the interviewer said to elicit that response.
Right from the start, the interviewer asked tough questions. “Haven’t the conservatives run out of ideas in America?” he asked. Then he hit Shapiro with an observation that new ideas were really coming from the Left, instead of Shapiro’s conservatives. Then he got under his skin by asking, “Why is it that a bill banning abortions after a woman has been pregnant for six weeks, is not a return to the Dark Ages?”
These are all legitimate questions for a conservative thinker, but reading how question after question unfolded, I understood why the barrage might make Shapiro feel personally attacked.
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🎬 With Ryan Hoover: “How to build an engaged community online.”
What do you do when you want to ask a question so difficult, it won’t cut it to just use someone else’s words? Here’s a technique I use to ask my toughest questions without scaring away my guests: pre-ask the shocking.
I used it when I was invited to interview investors on stage at LAUNCH Festival, the startup conference. After investor Jonathon Triest answered some of my questions about startup advice, I said to him, “You’re a photographer. You weren’t a startup guy. And the money you invested is family money.” Then I asked him what credibility he had telling entrepreneurs how to run companies when he built his business on his family’s money.
It might seem like an unfair question. But when I researched Jonathon, his family’s money and his lack of entrepreneurial experience are what stood out. Anyone who knew him might wonder the same thing and feel that leaving it out was avoiding a big, obvious issue.
The challenge with asking threatening questions like this is that the interviewee can feel so insulted that they stop trying to give helpful, interesting answers. Then the interview becomes painful for the audience to sit through—not to mention you.
A lot of advice can sound cliché. But when you share advice through stories, it becomes memorable and actionable.
When I interviewed Brad Feld, an entrepreneur turned investor, he told me that business is a series of successes and failures. That’s a fact, but it seems so obvious that it doesn’t have much impact on an audience.
I needed a story. So I followed up with, “Can you give an example of that?”
Brad said he invested in the startup BeMANY. After a strong effort to grow it, the founder, George Jankovic, “got to the point where the business simply wasn’t working.”
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🎬 With Brad Feld: “When You’re Ready To Get Past Clichés Like ‘Never Give Up,’ Listen To This.”
Many folks that offer interview advice to new podcasters include lists of questions to ask guests. These lists are often packed with what I call “most” questions:
What book had the most influence on you?
What’s the worst thing that happened to you?
Who was the most helpful person in your life?
I have a simple way to get relative strangers to talk to me about their parents, sex lives, and other personal topics.
I can almost hear you say, “That seems inappropriate, Andrew.” So first I need you to understand why I do it. Then I’ll show you how.
Years ago, I pressed Alexis Ohanian, co-founder of Reddit, to help me understand the business rationale behind selling his company so early. Today Reddit is worth over $6B, but he sold it for $10M–$20M.
Despite my efforts, I couldn’t get an answer that made sense to me.
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🎬 With Alexis Ohanian: “No, Reddit Didn’t Copy Digg. Here’s How It Was Built.”
Entrepreneurs are scrappy by nature. But not everyone sees this as a positive trait.
I’ve been criticized for the way I funded my first internet company. When no investor would bet on me, I called up J.Crew and asked, “Can I return all the clothes I bought when I was at New York University?”
The rep said, “Yes. We have a lifetime return policy.”
“Are you sure? I wore clothes throughout college. And I took the subway to school.”
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🎬 With Matt Mullenweg: “The Biography Of WordPress.”
I thought he’d be livid.
After months of convincing an entrepreneur to come onto Mixergy for an interview, I spent much of the conversation interrupting him. Talk about a terrible host, right?
But I had to do it. He was going on and on and taking us off-track. I couldn’t let my listeners put up with that. So I interrupted him—quite a bit.
After the interview, I prepared for him to rip into me.
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🎤 With Jeff Sawyer Lee: “$80M ARR by year two??!?”
A few years ago, I helped a few dozen members of my audience start interviewing. In a weekly meeting, one of them said, “I worry about not paying attention to my interviewee’s answer and being stuck finding a way to respond.” That’s much more common than people realize because many interviewers edit those goofs out.
I was sweating when that happened to me in my interview with Mike Jones, an entrepreneur who sold his company to AOL. My audience, at the time, was limited to the small Los Angeles tech community, where everyone knew Mike as one of its most successful members. I felt pressure to get the interview right.
To do that, I put together pages of notes. Then I took more notes during our conversation because I think better when I take notes. At one point, while he answered my question, I tried to find a note, but it was lost in the pages floating around on my desk. I didn’t hear his answer to my question. He paused. It was my turn to talk.
What could I do? If he had said something poignant and I shot back an irrelevant question, I’d seem insensitive. If I admitted I didn’t pay attention, I could lose credibility. I paused for a moment and suddenly came up with a question that I felt would always be relevant: “What’s your motivation?” Then I explained that I admired the hard work he put in, years after selling his company. Why was he putting himself through it?
One day, as I was leaving my office, I got a call from a prominent Silicon Valley founder I interviewed earlier that morning.
“I’m upset with you,” she came right out and said.
I was stunned. I racked my brain trying to figure out why she’d be mad. Her interview went off without a hitch. If anything, I felt like I was more accommodating than usual. She was in a relationship with someone famous. To preserve her privacy, I didn’t bring it up, even though it could have given my show a traffic boost. We focused strictly on her business, and I even let her promote more than I normally would.
My only tough question came at the end. We had scheduled the interview multiple times, and she didn’t show up. She seemed to have done that to another interviewer, who mentioned it on his podcast. So I asked why she didn’t show up when she said she would.
Before we leave this section, I want to leave you with one important message: if you fail with every tip I gave you so far, you’ll do well if you simply let your guest talk.
I realized the importance of this years ago at a quiet dinner with my brother, Michael. I got a call from one of the employees at the greeting card company he and I founded.
“Andrew, I can’t stop crying,” she said.
I was surprised, not that she was crying or the reason why she was crying. I knew about the tough breakup she was going through. What took me by surprise was that she wanted to talk to me, not Michael.
In Part I, you learned high-impact conversation techniques that will elevate every interaction and interview. But great conversations are created before they even begin. If you’re ready to uncover deeper insights from your guests and people you admire, it’s time to learn how to prepare for each interview.
Preparation is what separates the great interviewers from the good ones. It’s also why some people can walk into a room and immediately make a deep connection with everyone they meet. In this part, we’ll take a step back and look at the interview process as a whole. We’ll start with teaching you how pre-interviewing will improve your conversations. Then we’ll look at five different interview structures you can use to organize your conversation. After that, I’ll share how I conduct research on my interviewees.
Finally, we’ll close with a few more techniques to keep conversations meaningful and interesting.
The pre-interview is an underappreciated part of the interview process because it’s hidden from the audience. But if you spend even a few minutes doing it, your interview will be noticeably better.
I added pre-interviews to my process to fix a common problem: guests forgetting to share their most memorable stories.
After recording one of my first interviews, I saw my guest exhale and let out the pressure he built up. “You did great,” I said.
“Thanks, but I wish I told you the story of how I got my first customers. I found a way to automate posting my ads on dozens of Craigslist sites. It violated their rules, but it helped my company take off. I forgot about it when you asked me. When I remembered, the conversation felt too far along to return to it.”
Most people aren’t familiar with pre-interviews, so explain what you’re going to do and why. This is especially important if you’re doing the pre-interview yourself. You don’t want your guest to confuse it with the actual interview.
Focus on the key parts of the interview. This isn’t a dry run of the interview—it’s information gathering, or as I like to call it, story gathering.
If you’re doing the pre-interview yourself, always interrupt good stories and explain that you want your guest to sound unrehearsed and fresh in the interview.
The output of a successful pre-interview is a list of stories your guest tells well and maybe a few that you should stay away from.
Throughout human history, knowledge has been passed down from generation to generation. Not with charts and spreadsheets, but with stories.
Stories have a way of embedding lessons into our minds. They help us remember hard-earned wisdom we’d otherwise forget. That’s why, as an interviewer, my goal is to get guests to tell me stories from their lives—not just share what they’ve learned.
The quintessential human story is what Joseph Campbell dubbed the Hero’s Journey. But before we get into that, let me tell you a story of my own.
Shortly after starting my first company—an online greeting card business—I was struggling to make sales. Banner ads were an important part of my business model, but I didn’t have the chops to convince sponsors to take a chance on my site. That’s when I learned about Rosalind Resnick, a seasoned entrepreneur whose company sold ads for online businesses. I thought, if I could just get Rosalind to help me, my business might survive.
Most interviewers guide their how-to interviews based on the questions they think up when they’re trying to learn the topic. That approach works fine, but it’s not the optimal way to teach something.
My how-to interview structure is so effective that I call those interviews “Master Classes,” and I charge for them. That’s because by the end of the interview, my audience will have acquired a useful new skill, like growing their website’s sales. But how-to interviews also take more work to put together. I can’t do these interviews well without an extensive pre-interview or doing heavy research.
In this section, I’ll show you how to prepare a how-to interview that’s so good, your audience will pay you to teach them. At the very least, you’ll know how to structure conversations to learn more effectively from experts you admire.
Before we get into it, let’s talk for a minute about Blue Apron.
Below is an actual outline my team and I created before interviewing Scott Bintz.
We based this outline on his book, Principles to Fortune, as well as our own research and a short pre-interview. You’ll notice the outline doesn’t include full stories. I just need a short prompt that will guide my guest to his story.
Topic: How to Create a Company Culture That Grows Sales
Interviewee: Scott Bintz, founder of RealTruck, an online auto-part store
Before: Scott’s story about how he started to hate working at the company he founded and led. He tried creating a company culture by writing down the company values, but his team ignored them and the effort fizzled out.
After: After a recommitment to his company’s culture, Scott’s team focused on hitting goals while still having fun. They even convinced Scott to shave his head if they reached their goal of $10M in sales. After they hit the goal, Scott cut off his shoulder-length hair and donated it.
Tactic 1: Ask your employees what they already value.
Story: Instead of writing the values he wanted his company to follow, he asked everyone on his team to write down what makes the company meaningful to them.
Tactic 2: Condense the team’s responses to core company values.
Story: Scott sat down with all the responses he got and looked for common values. Then he picked the ones that he thought would create a fun environment and help his company grow.
Tactic 3: Track only metrics that matter.
Story: Scott eliminated his customer support team’s sales goals because they blocked a core value: “deliver more.” As a result, the team started delighting customers. Once, the wife of a customer called to say her husband loved his truck like a mistress, and she wanted to buy a surprise treat for it. After placing her order, the support person sent her a surprise bouquet of flowers with a note that said, “We think the wife deserves a little treat too.”
Tactic 4: Roll out values one at a time.
Story: In the past, Scott posted his company’s values and was disappointed that no one lived up to them. His new approach was to roll out each value individually and spend an entire month teaching and reinforcing each one.
Tactic 5: Embed each value into the company.
Story: At a meeting, he asked everyone to think of ways they could live one of their core values. Everyone wrote down a suggestion. He picked some and got the company to implement them. That’s how the company ended up writing cards to customers, sending them free fuzzy dice for their rearview mirrors, and surprising them with gifts.
Tactic 6: Recognize and reward employees who live the core values.
Story: Scott’s team had many prizes made up so employees could give them to coworkers who were living out the company’s values.
🎬 With Scott Bintz: “How running a truck accessory company with an e-commerce culture led to $100M ARR.”
🎤 With Chris Ronzio: “Chris Ronzio streamlines the onboarding and training process with Trainual.”
🎤 With Shilpi Sharma: “YEC Founder Series: Kvantum.”
I don’t like to focus on the news because its relevance expires fast. When Jon Stewart hosted The Daily Show, he was the comic that millions of people turned to when they wanted to understand world events. After he was off the air, his episodes were removed from The Daily Show’s website.
Meanwhile, video platforms are outbidding each other for the rights to play reruns of timeless shows like Seinfeld.
I prefer to record interviews that will be as useful decades from now as they are the day I publish them. Still, news-based interviews have their place. When controversy strikes, interviews with the person at the center of the storm will draw a large audience. For me, it’s also a chance to better understand how entrepreneurs think.
Unlike the Hero’s Journey and how-to structures, news-based interviews don’t follow a clear structure, but they do have common elements. Most interviewers will launch right into the issue that made the news. That’s why everyone’s there, right? To hold off would be like forcing a thirsty man to listen to a sales pitch before handing him a glass of water.
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🎬 With Joel Spolsky: “Breaking News: Why Didn’t Stack Exchange Work?.”
This interview format was popularized by Joe Rogan, the comedian-turned-podcaster who signed a $100M deal to make his show exclusive to Spotify listeners. Rogan can talk to his guests for more than three hours per interview, often with a whiskey in his hand. His conversations bounce between topics like discipline, nutrition, drugs, and exercise, without much more connecting them than Rogan’s interest.
These types of interviews seem to lack structure, but when I studied Rogan’s transcripts, I saw a clear methodology. I call these interviews “serendipitous” because the host moves quickly through topics, looking for surprise gems. They’re like a pub crawler who goes from bar to bar, spending more time in the ones that are fun and moving on the moment things get stale.
A good example is Rogan’s interview with Elon Musk, the billionaire behind SpaceX and Tesla. Listen to how fast they zip through topics. They take just seven seconds to greet each other. Then Rogan asks about flamethrowers. Musk gives answers I’ve heard him give before, so three minutes and 45 seconds later, Rogan ditches the topic.
“Forget about the flamethrower,” he says. “How does one decide to fix LA traffic by drilling holes in the ground?” He moved on to Musk’s Boring Company, which aims to ease Los Angeles traffic with tunnels.
Panels tend to be a refuge for the lazy. That’s why they’re painful for audiences to sit through. It’s true of both traditional in-person conferences and emerging online panels, like the social audio pioneered by Clubhouse and video summits done by virtual conferences.
To understand the problem with panels, let’s look at a conference I spoke at. As I waited in the green room for my turn on stage, I watched the conference organizer introduce a moderator to his panelists moments before they were to go on stage. The moderator laughed as he told his panelists, “I prefer leading panels to giving presentations because I hate the work of putting slides together.” The panelists nodded in agreement. They masked their laziness as a hack, congratulating themselves for getting attention by being on stage, without doing any work.
On stage, the moderator sat limply as he tossed softball questions, like, “Could you tell us about yourself?” Even when they talked for too long or were too self-promotional, he let them go on. Many moderators blame their panelists for not knowing how to give good answers instead of taking responsibility as the leaders of the conversation.
With a bit of effort, you can make your panels engaging and useful. Moderating a panel well is similar to leading an interview. The work is multiplied by the number of panelists you have, but so are the benefits. To do it right and stand out in a crowd of mediocrity, you need to use all the usual tools of a good interviewer. Let’s break that down.
Once you decide on the structure of an interview, it’s time to start researching.
I begin by thinking of all the questions I want to ask my guest. Then I research as many possible answers as I can to give me insight into how they might respond. During the interview, I use the information I gathered to guide my guest and fill in any missing pieces that I couldn’t find online.
Many interviewers skip doing research. In fact, some interviewers believe a lack of research is the best way to empathize with the audience. By not doing research, the argument goes, the interviewer can ask the questions the audience would ask if they could talk with the guest.
This isn’t just bad advice—it could ruin your reputation with your guest and audience.
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🎤 With Derek Sivers: “How A Musician Built A $22 Million Dollar Business From His Home.”
🎤 With Rasty Turek: “Investors hated Pex until this…”
Beyond the research that I do to find content for the interview, I also like to do a bit of homework to improve my relationship with the guest.
Attention to detail comes in handy in situations like the pre-interview I did with Gregory Galant, founder of the Shorty Awards (a coveted award for social media stars) and Muck Rack (a tool for helping companies in media.)
The pre-interview with Greg was productive, but he kept leaning back from his webcam for much of it, as if he was trying to protect himself from me. I get it. Doing a good interview is challenging, but being interviewed also comes with landmines. Some guests worry they might reveal too much about their companies. Or maybe they’ll take credit for something that others did, and their team will think they’re self-aggrandizing. Or maybe they think the interviewer has some hidden agenda to bring them down. Whatever their worry, guests can be a bit cagey.
Through my research, I saw that Greg posted about his bike on his personal blog. When I talked to him about it in the pre-interview, he smiled. He went on to tell me about the multi-day bike rides he did. He shared that he carried camping gear on his bike and slept outdoors between strenuous cycling days. And he told me that one of his few splurges after growing his company was buying an expensive bike. He had a big smile on his face as he told me all this. And so did I.
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🎤 With Gregory Galant: “Shorty Awards Creator.”
🎤 With Steven Clausnitzer: “YC-backed stem cell banking.”
Many people sit behind a mic and think they’ve suddenly turned into the reporters they see on the evening news. They think the professional thing to do is get the facts for some imagined audience that expects formality.
That’s the old way. It doesn’t work online, where you don’t have a general audience. Your audience is made of enthusiasts who want to learn about their passion from someone who is just as passionate as they are. They want to know about you as much as they want to get to know the person you’re interviewing.
I miss this point myself sometimes. When it was time to hire someone to help me lead my company, my business coach told me to interview Cameron Herold, the former COO of 1-800-GOT-JUNK, the junk removal service. “I can’t,” I told her. “Mixergy is about interviews with proven founders who talk about how they built their businesses. He didn’t found 1-800-GOT-JUNK.”
Like a good coach, she kept pushing. “You’re dealing with a challenge every entrepreneur in your audience will face at some point. Ask him.”
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🎬 With Cameron Herold: “Cameron Herold coaches me on hiring (so I don’t collapse at my desk).”
It can be valuable to put your needs front and center during a conversation. But that doesn’t mean you ignore your audience. Audience intel is one of the best ways to steer your interviews toward the most painful and productive lessons.
My favorite form of audience intel is Scotch Night, which came up in the section about the dramatic lowball technique. I’ve hosted these events for years. The premise is simple: I’ll buy three different bottles of Scotch (along with snacks and other beverages) and invite people to my office to try them. As you might have guessed, this event really isn’t about the Scotch—it’s about having time to get to know people who listen to my interviews. In this casual and intimate atmosphere, folks share things they would never think to include in an audience research survey.
During one Scotch Night, an entrepreneur in attendance started the evening talking about the early success of his new business. He sold flashing car rims—a surprisingly lucrative industry. He hit over $100K in annual sales within months of launching. That was a big win for him.
But as the evening went on, and he became more comfortable, he shared how anxious he really was. “How do I know when I should quit my full-time job and focus on this business?” he asked.
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.
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🎤 With Ahti Heinla: “The co-founder of Skype joins me in Estonia.”
🎤 With Shoba Murali: “Finding a big audience for a unique solution.”
Everyone has a plan until you get punched in the mouth.
Mike Tyson’s famous insight applies to interviews as much as it does to boxing.
You should go into every interview with an outline. That’s why I gave you five different interview structures to work from. But if you aren’t willing to ditch your plan, you’ll miss opportunities and cause unnecessary friction with your guests.
I’ve learned this lesson the hard way—on multiple occasions. The first time was when I interviewed Fred Wilson, an investor and Twitter board member. The week of our interview, Fred found himself at the center of a controversy between Twitter and startups building apps for its platform. Business Insider reported: “Holy Cow Did Twitter’s Top Investor Drop a Bombshell on Twitter App-Makers Today.” Fred seemed to say that Twitter was going to put those small companies out of business by stealing their best features.
Movie producers use billboards to get people into theaters to watch their films. Few podcasts have the luxury of that kind of budget. Instead, listeners use the first few seconds of each episode to decide whether or not it’s worth their time.
Just how important is your opening? Reality set in for many podcasters when Anchor, the podcast creation app, gave its creators second-by-second analytics for each episode. When podcasters looked at their graphs, many saw big drop-offs in listenership just moments after their podcasts started. Some lost over half their listeners within a minute. As NPR producer Nick Fountain said, “If you don’t hook people in within the first minute, you’re screwed.”
This isn’t just true for podcasters. The principle applies to nearly every medium. In our attention-starved world, the first few seconds of any content are the most important.
Interviewers don’t have traditional billboards, but we still need creative ways to capture and keep our audience’s interest. Here are four billboard techniques you can use.
The easiest way to introduce an interview is by telling listeners why you chose the interviewee and why you think it’s important for them to listen. I used this opening with Tara Reed, founder of Apps Without Code, which teaches entrepreneurs to build software without programming.
I introduced her by saying that I spent years rejecting listener suggestions for me to interview her. Frankly, I didn’t believe good apps could be built without code. But then I tried no-code tools for myself and realized how big the possibilities were. Later I discovered that Tara had raised money from Silicon Valley investors for a software company built entirely without code. Finally, I decided I had to interview her. I had a responsibility to help non-developers in my audience understand this new way of building software companies.
Another way to hook listeners is to begin with a shocking question. One of my favorite opening questions is to ask founders how much revenue their businesses generate. That signals to my audience we’re going to get into topics that are usually considered too personal to discuss in public.
Oprah Winfrey used this technique in her interview with cyclist Lance Armstrong. Her first question to him was, “Did you ever take banned substances to enhance your cycling performance?” Does an interview get any more captivating than that?
But remember my advice from Part I: if you’re worried about a guest’s response to your shocking question, pre-ask it before recording. Make sure they’re prepared to answer and continue with the interview. You don’t want them so caught off guard that they shut down for the rest of the conversation.
Sometimes, one hook isn’t enough. NPR producers like using the rule of three, a principle that says focusing on a trio of events makes the material more enjoyable and memorable.
When podcaster and founder of AppSumo, Noah Kagan, interviewed NPR producer Nick Fountain, Noah illustrated this principle. At the start of the episode, he recorded a summary of the top three lessons from the interview. He said, “I learned three major things that I’m going to share with you today. Number one, how to hook your listeners. Number two, why editing is king. And number three, how to create a real narrative for your work and closing out what you make.”
A fourth option is to clip a highlight from the interview and play it for the audience before the interview starts. LinkedIn founder Reid Hoffman often uses this technique on his show, Masters of Scale.
In his interview with Richard Branson, founder of Virgin Group, Reid pulled a clip in which Branson talked about heading to a party at Las Vegas’s towering Palms Hotel. Upon arriving, Branson was surprised to learn he would be entering the party by jumping from the top of the building! The story is certainly interesting in itself, and it showed listeners that this wasn’t just another business interview.
Whether you choose one of these four suggestions or take another approach, the important thing to remember is this:
At the start of your interview, your listener is not asking, “What does this interviewer have in store for me?” but “Do I really want to listen to this interview?”
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Now that you know how to prepare and carry on meaningful conversations, it’s time to talk about your guests. This section will walk you through how to find the right people to interview.
Before writing this chapter, I looked at my download stats for the year. Who was my most popular guest?
I expected it to be the founder of Riot Games, creators of the worldwide sensation League of Legends. Around 115M people played the game in 2020. More people watched the League of Legends World Championship in 2019 than watched the Super Bowl. Clearly, he has a following. He was a sharp guest with a compelling story. But no, his interview didn’t get me the year’s biggest audience.
The title of most popular Mixergy interview for 2020 goes to a founder whose company is significantly less known. Andrew Burnett-Thompson is a quiet developer who built SciChart, software that allows other developers to add helpful charts to their apps. Why was his episode so popular?
Andrew had good jobs working for big companies like energy giant BP. But he was fascinated by the entrepreneurs he heard on my podcast and in the startup world. He decided to teach himself to code by reading programming books and doing one lesson per day. Then, when he realized how hard it was for developers like him to create charts, he decided to launch a company to solve the problem. He got up early every morning and worked while his wife and baby slept. On his train ride to and from work, while others fiddled with their phones, he pulled out his laptop and coded the foundation of his startup’s software.
🎤 With Marc Merrill: “How Riot Games founder Marc Merrill overcame massive hurdles to build League of Legends.”
🎤 With Andrew Burnett-Thompson: “Chart software coded on a morning commute.” See if you can figure out why he was so popular.
🎬 With Drew Houston and Brian Chesky.
I strongly believe that you don’t need superstar guests. Less than 10% of the interviews I’ve done have been with big-name people. It hasn’t stopped me from building a solid personal brand, a large audience, and a strong business from my interviews.
Still, landing the occasional big shot is worth the work because they’ll help grow your audience and increase your credibility with other interviewees you’re trying to land.
The challenge is that celebrity guests who are in demand usually don’t have enough incentive to sit for an interview with you, or even respond to your request. There are times, however, when they’re eager to be interviewed. I call those times motivated moments.
A motivated moment is when a popular author is releasing a new book and wants to try to hit the bestseller list. It’s when a reclusive movie star suddenly appears on multiple talk shows to promote a new TV series, or a billionaire founder is launching a new startup and appears on podcasts he’s never heard of before.
🎤 With Tim Ferriss: “How Blogs Helped The Four Hour Work Week Become a Best Seller.”
🎤 With David Rubenstein: “David Rubenstein of The Carlyle Group.”
🎬 With Justin Kan: “Exec: How Does A Lifecaster Create Multiple Hit Companies?”
The most-watched interviews in mainstream press have always been news-based. In 1993, when Michael Jackson was accused of child sexual abuse, he sat for an interview with Oprah Winfrey. It became the most-watched interview in American history, with 90M people tuning in. The Top 10 list of most-watched interviews is full of politicians, royalty, and accused criminals who made headlines around the world.
But you don’t need to land worldwide headliners to take advantage of breaking news. All you need are people making headlines in your audience’s world. My world is the tech startup community. One day, two well-known people in my world became newsmakers.
I read somewhere that Matt Mullenweg was upset. As the founder of WordPress, the world’s most popular web-publishing platform, startup founders paid attention to what he said. Matt was frustrated that Chris Pearson, a popular designer and software engineer, had the audacity to sell a WordPress template instead of making it free like the WordPress platform itself.
Bloggers in the WordPress community were writing about the fight. So were large tech news sites. Meanwhile, people on both sides of the argument were tweeting their opinions. It was big news in the startup world. So I asked both Chris and Matt if they’d let me interview them together via Skype to understand each of their points of view. They agreed.
🎤 With Gagan Biyani: “How Sprig lost over $50 million.”
🎤 With Bari Baumgardner: “How this live events company pivoted in a time of COVID.”
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.
A couple of years after launching my interview series, I started running out of guests to interview. My network of entrepreneurs was sizable, but it wasn’t infinite. How could I reach outside my network but still get quality guests?
Many of the entrepreneurs I interviewed had a similar problem, like Naomi Simson, founder of RedBalloon, which enables people to gift experiences, such as hot air balloon rides and car race days. When she ran out of contacts at companies that offered experiences, she asked her suppliers for referrals. That did the trick.
Since many businesses use referrals, I figured interviewers could too. And I found a way to make them even more powerful.
If you listen to my early interviews, you’ll hear me ask guests for referrals within the interviews … with my whole audience listening. I wanted to share my approach with my audience and show them how I was thinking about upcoming guests. It also had the benefit of committing my guests to follow through on their offers to introduce me.
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🎬 With Naomi Simson: “How A Persistent Entrepreneur Turned RedBalloon From Near Disaster To eCommerce Hit.”
Bob Hiler was tired of hearing me talk about my struggle to find strong interview guests. Every week we’d get on a coaching call to talk about what I was working on, and every week I’d talk in circles, grasping for ways to find my next guest.
“This isn’t working,” my coach said in frustration. “You can’t keep looking for ideas. You need idea fountains.”
I immediately Googled to see what it meant.
“It’s not in Google,” he said. “I just made it up. On each call with me, you look for one guest. What if instead of looking for one new guest each week, you search for one source of new guests? Try it now. What do your most recent best guests have in common?”
The startup community was enthralled by Fred Wilson. As a social media pioneer, he was an early user and investor in some of the world’s most popular apps: Twitter, Kickstarter, Etsy, and other companies that reshaped the internet and our communities.
My audience wanted to hear from him, and I wanted to interview him. But he wasn’t replying to my emails. I’m not sure he even saw them.
So I did something I had never done before—I asked my audience for help. I made a public plea for someone to connect me with Fred. I asked my fans during live streams. I blogged about what I wanted to learn from him. I told my email subscribers how badly I wanted this interview.
And then, something amazing happened: my audience came through.
🎬 With Mike Colella: “The $2.2 Million Affiliate Who Wouldn’t Let Me Interview Him.”
🎬 With Dennis Crowley: “Meet The Entrepreneur Whose Company Is Inventing The Future.”
When you’re just starting out as an interviewer, it’s hard to get guests. When you’re established, it’s hard to turn down guests. But if you say “yes” to every request because you’re too scared to say no, your quality will inevitably dip. And your audience will notice.
As tough as it is, you have to learn to turn down interview requests. I’ll show you the right way to say no and help you avoid the wrong ways.
For years I turned people down the wrong way. I once got on a call with a prospective guest because a mutual friend asked me to consider him. He was a nice guy, but I quickly knew I didn’t want to interview him. His company was too new. He hadn’t done much yet. And frankly, I just wasn’t curious enough about him. So I told him, “I’m sorry, but your company is too new. I can’t do this interview, but I’d love to have you on when your company grows a bit.”
I thought I was clear, and we’d just move on. He didn’t want to. “As a listener, I can tell you that you need to feature more new companies,” he said.
I intentionally focused this book on the timeless craft of interviewing and not the business of interviewing. I wanted the ideas to be as true in the future, when conversations might be held in virtual reality, as they were when I did a one-on-one interview in a cold tent in Antarctica.
But many readers are interested in how to turn interviewing into a marketing channel, a side hustle, or even a full-time career. If that’s you, certain business fundamentals are necessary to master if you want your interviews to be sustainable over the long term.
Promotional techniques change constantly and are best left to marketers to teach. But there’s one approach that’s unique to interviewing and vital to mention: get help from your guests to promote your interviews.
Guest promotion can be varied and unpredictable. When I interviewed Paul Graham about how he launched Y Combinator, one of Silicon Valley’s most prestigious startup incubators, his firm featured my episode on their homepage for months. Vishen Lakhiani, founder of Mindvalley, the online education company, used Facebook ads to promote his interview and drove traffic to my site. But most guests don’t do anything to promote their interviews with me.
What a guest does with an interview after it’s published is out of the interviewer’s hands. However, there are ways to nudge them toward helping you promote their episode.
I learned the most powerful technique from a friend who runs an interview podcast that’s often on Apple’s Top 10 list. Before the interview starts, he lists all the ways he’ll promote his interviewee. He’ll share it in his email newsletter, post it on his popular Instagram account, and so on. He’ll spread his guest’s message far and wide. Then he turns to his guest and asks, “How can you help me promote you?”
🎬 With Paul Graham: “How Y Combinator Helped 172 Startups Take Off.”
🎬 With Vishen Lakhiani: “How MindValley Founder Built A $40M Company With Only $700.“
🎬 With Quin Hoxie: “Swiftype: The Biggest Search Engine You’ve Never Heard Of.”
My interview booking process used to be a mess, and it took up too much of my time.
I never knew if my pipeline of upcoming guests was big enough or if I had to scramble to find new ones. I had to approve or reject every single guest myself. My producers didn’t know whom they needed to pre-interview. When they got on calls with upcoming guests, they didn’t know what the interview would be about. All this uncertainty meant I often got 6:00 a.m. text messages asking for solutions to problems that could derail an upcoming interview or damage my relationship with an upcoming guest.
At the time, my wife was just a few months away from giving birth to our first child. I realized I couldn’t be both a good dad and a good interviewer unless I solved the chaos.
So again, I tapped into what I learned from my successful interview guests and created a system for managing interviews. The system allows my team to do their jobs well without needing my help, and it gives me the freedom to focus on doing meaningful interviews.
It took me a year of publishing three episodes a week to finally feel “ready” to sell ads on Mixergy. The truth is, I had no idea what I was doing. But step-by-step, I built a sponsorship revenue stream that took my little podcast from a hobby to a full-time business with multiple employees.
Some podcasts will be ready to sell ads faster than I was. Some slower. No matter what, your podcast sponsorship journey will go through three stages: startup, growth, and maturity.
The startup phase began a year after I started interviewing and felt ready to look for my first sponsor. At the time, I didn’t know what to charge. I didn’t even know how many people listened to my podcast because the publishing software I used didn’t keep track of listenership.
The startup stage of sponsorship sales is full of unknowns for both creator and sponsor. That’s why you should start with learning, not selling. Then, when you start selling, prioritize getting data from sponsors over making money from them. And, to eliminate the uncertainty for them, guarantee results.
I first needed to answer a simple question: How much could I charge? There’s no ad platform for podcasts that will automatically tell you the value of your show. I had to find someone with some experience who would be friendly enough to help me. Scouring online message boards, I met Sunir Shah, an ads buyer from FreshBooks. At the time, FreshBooks bought a lot of advertising on podcasts similar to mine, so I asked Sunir if he’d help me understand ad sales. I sent him a link to all the interviews I had recorded to show I was serious. He and the FreshBooks team gave me invaluable advice. They taught me how they bought ads, which sites performed well for them, and what great ads looked like.
New content creators and publishers are intimidated by ad buyers. I’ve found it helps to remember that it’s an ad buyers’ job to find new, productive places to advertise. They want to work with us.
The startup stage was defined by selling single-episode ads to individual sponsors. My goal during that stage was to acquire data, not make money. With data in hand, I felt confident to move to the next stage of ad sales: revenue growth.
I hired Sachit Gupta, a business development consultant, who helped me realize that my reputation was strong enough for companies to invest in long-term relationships with my audience. Before I started working with Sachit, my sponsors were companies with relatively low-cost products. They needed to acquire a lot of new customers to make the ads worthwhile.
To increase my ad rates, Sachit suggested going after businesses with high customer lifetime values (LTV). That meant they only needed a few new customers to be profitable, and they’d be willing to spend more to acquire them.
A good example of a high LTV sponsor is Toptal, which helps businesses hire top developers and other professionals. Though prices start low, it’s not uncommon for a Toptal client to spend tens of thousands of dollars per year on developers. Customers don’t make that kind of decision after just one ad. It took time and repeated exposure to Toptal ads. Sachit realized that based on my reputation, Toptal would be willing to invest in a long relationship and multiple ads.
The maturity stage of the ads journey can be traced back to a little link that’s been on my site for over a decade. It simply says “Sponsor.” It links to a form where businesses that want to sponsor my interviews can tell my team about themselves and schedule a call to talk about buying ads.
Today, every single show sponsor uses that link to start their relationship with me. Ad buyers find it because of the reputation my site built over the years. Each interview I publish draws in new listeners. Some of those happen to be ad buyers who want to buy podcast ads. Each link to my site adds to my reputation with Google, which helps me show up higher in search results done by ad buyers. Each new article written about my work is another potential source of sponsors.
My job isn’t to hunt for new sponsors anymore. It’s to talk to each potential sponsor and make sure that what they have to offer would be a good fit for my audience.
I’m surprised by how many interviewers will pitch socks, mattresses, and other random goods for their sponsors but never sell their own products to their audiences.
You might be OK forgoing the revenue, but by not selling your own products, you’re missing an even bigger opportunity: to understand your customers and make their lives better in ways that only you are qualified to do.
Pat Flynn is a master at selling products to his audience that solve real problems. Pat has been interviewing about as long as I have. One of his favorite topics is the art of podcasting. By talking to podcasters in his audience, he realized that one of their biggest frustrations was posting their podcasts on their own websites. That’s because traditionally, podcasts were meant to be played in dedicated podcast apps. With this insight, Pat created Fusebox, an audio player you embed on your website. He nailed a problem that plagued my business for years. I’ve been a grateful customer of Fusebox for a long time.
There’s a satisfaction that comes from solving your audience’s problem in a way that no one has before. But you don’t have to build a software product. Jamie Masters sells coaching. Jason Calacanis sells access to his angel fund. Sam Parr sells research.
I’ve talked to dozens of people who started podcasts and quit after just a few episodes. Many were embarrassed—they had good conversation skills but could only produce a handful of interviews. What was wrong with them?
I feel for them. In fact, I was in their shoes. Episode #8 of Mixergy was almost my last.
Episode #8 was with Bill Reichert, founder of Garage Technology Ventures. I remember thinking how hesitant he seemed to talk with me. My interview style was completely unpolished. Our conversation was full of “ums” and “ahs” and slow responses. I worried he regretted interviewing with me because my audience was so small.
Afterward, I felt like such a failure that I wanted to give up interviewing. I was ready to quit. But I couldn’t. Not because I was determined—my motivation was all but gone. I couldn’t give up because I had already scheduled more interviews.
🎤 With Bill Reichert: “Startup Funding Interview with Bill Reichert of Garage.”
🎤 With Tyler Suchman: “Search Engine Optimization Strategies.”
🎤 With Tara Hunt: “Why & How to Build Social Capital Online.”
This isn’t a book of rules. It’s a book of tools.
My goal isn’t to bind you to what worked for me but to give you ways to enjoy interviews and learn from them.
I started writing this book at a challenging time. San Francisco, my hometown of nine years, went into lockdown to prevent the spread of the COVID-19 virus. I went from working at an office I loved to recording my interviews on a small card table in a corner of my bedroom. I was miserable about the change and didn’t fail to mention it in interviews.
I started writing this book to do something meaningful in my newfound solitary time at home. It was my chance to help interviewers.
This book is only possible because of the exceptional people I’ve had a chance to interview. Here is a bit more about some of the ones mentioned in the book, as well as the businesses they’ve created.
Alan “Ace” Greenberg was a chairman of the executive committee of The Bear Stearns Companies, Inc.
Included in this digital Holloway Edition are three in-depth video tutorials developed specifically for readers of this book. High Impact Podcasting With Andrew Warner covers all aspects of producing a podcast, broken into three one-hour conversations.
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