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#76: Andrew Warner [Persistence] – How to be a better conversationalist with the host of 2,000+ interviews

October 19, 2021

#76: Andrew Warner [Persistence] – How to be a better conversationalist with the host of 2,000+ interviews
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Andrew Warner is the founder of Mixergy and host of the Startup Stories Podcast by Mixergy, where he uncovers the secrets of the world’s best founders.

Andrew Warner is the founder of Mixergy and host of the Startup Stories Podcast by Mixergy, where he uncovers the secrets of the world’s best founders. Over the course of 2,000+ episodes, Andrew has interviewed everyone from Barbara Corcoran, to Gary Vee, to the founders of Airbnb.

He's also the author of Stop Asking Questions: How to Lead High-Impact Interviews And Learn Anything from Anyone.

After building two startups of his own—one successful and one failed—Andrew started Mixergy as a way to learn from other entrepreneurs. Today, Mixergy is a place where successful people teach ambitious upstarts through interviews, courses, masterclasses, and events. 

So in this episode, we talk about why Andrew became fascinated with learning from others, feeling starstruck as an interviewer, small ways YOU can become a better conversationalist, and how his persistence has helped him through the challenges of building a podcast and writing this book.

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Andrew Warner  00:00

If I ever stopped feeling starstruck, I should be talking to other people. I should stop what I'm doing. It's an indication that I'm talking to the wrong people. You have to feel starstruck, you have to talk to people who you're an absolute awe of. And if you're not, what's the point?


Jay Clouse  00:17

Welcome to Creative Elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show. Hello, my friend. Welcome back to another episode of Creative Elements. I missed you last week. Thanks for bearing with me through a bit of an off week that allowed Mallory and I to take a much needed weekend trip to North Carolina. And thank you to everyone who listened to last week's episode about our listener survey and have already completed it. If you haven't taken our Creative Elements listener survey yet, there's a link in the show notes. Please take a few minutes to do so, I want to learn more about you. And on November 1st, I'll be awarding two listeners who complete the survey with a $200 amazon gift card. And lastly, thank you to dream pop fan who left a five star review on Apple podcasts and wrote quote, Jays show is inspiring just what us creatives need as inspiration to keep going, thanks for everything. Thank you dream pop fan those reviews on Apple podcast go a long way so please keep them coming. Okay, today I'm doing something that I don't normally do on this show. And I'm bringing on a guest who has a new book. It was actually released yesterday, Monday, October 18th. Here's the thing, I'm a podcast listener as much as I am a podcast host. And as a listener, I get a little bit annoyed when I see an author doing a podcast tour across a ton of shows in my feed at the same time promoting a book. As a podcast host, I get it. A lot of times the author is someone who is typically hard to book as a guest. And this is a win-win to make that conversation happen. All this to say I've made an agreement with myself that when I have an author on the show, it's because I've read the book already, already loved that person's work, or both. And I'll probably focus the interview on a creator's career rather than having the same conversation about the book itself. Well, today's guest, Andrew Warner falls into both of those camps. Andrew Warner is the founder of Mixergy and the host of the podcast startup stories where he uncovers the secrets of the world's best founders. Over the course of more than 2000 interviews, Andrew has interviewed everyone from Shark Tank's Barbara Corcoran to Gary Vaynerchuk, to the founders of Airbnb. In his 20s, Andrew started a greeting card company called Bradford & Reed. At its peak, the company was processing 400,000 greeting cards per day, and $1 million in revenue per month. Then in 2003, after experiencing some burnout, Andrew and his brother sold the company and he took a break. And in that break is when he discovered the magic of interviewing.


Andrew Warner  03:10

I started out Mixergy with these in person events, thinking that in person events would be a way to get people together. And once you get them together, you say okay, we're all getting together. Now let's talk about how we can build ourselves up. And the way I always believe in building yourself up is through learning something. And so I thought I would end up doing these local education programs and I started doing that. Mixergy was events first in Santa Monica with the idea that it would go beyond the LA area. And so I would host these lunches in people's offices, it was great.


Jay Clouse  03:41

It didn't take long for Andrews in person events in startup offices to grow and become more and more popular. So Andrew started to look for a bigger space to host these conversations.


Andrew Warner  03:52

And then I started renting out theaters in in LA which you can imagine Los Angeles near Hollywood, it's fairly easy to find a theater. And instead of bringing actors on stage, I bring experienced entrepreneurs on stage and I'd say you don't have to do any work. I will interview you about what my audience needs to learn from you and then go and talk to them afterwards. And I led these interviews on stage and they did well, I was able to sell tickets we'd get 100 people into into a nice theater. And it felt it felt like that was the approach.


Jay Clouse  04:24

Of course at this time, Andrew was very familiar with internet businesses. So he realized that there was an opportunity to take Mixergy online and his in person interviews became remote interviews, of which he has now recorded more than again, 2000 and that brings us to Andrews book, which I said was released yesterday and it's called Stop Asking Questions, how to lead high impact interviews and learn anything from anyone. He's taken his decades of interviewing experience and written in extremely practical and accessible guide on how to become a better interviewer. Not only a better interviewer, but a better conversationalist. So in this episode we talk about why Andrew became fascinated with learning from others, feeling starstruck as an interviewer, small ways you can become a better conversationalist, and how his persistence has helped him through the challenges of building a podcast and writing his book. I'd love to hear your thoughts on this episode. As you listen, you can find me on Twitter or on Instagram @jayclouse, tag me, let me know what you're doing right now as you're listening to this, I'd be really curious to hear. And now let's talk to Andrew.


Andrew Warner  05:38

I used to watch biography as a kid on A&E all the time and they would go through the richest people in history and give their biographies. And I'd be riveted and love it and say one day, I'm going to be just like them. And I remember there's this guy who came on Ace Greenberg, who was on there talking about the finances of people who were on Wall Street. He was an incredible investor, incredible CEO. And I worked as an intern for somebody, who worked for somebody, worked for somebody, worked for him. And I said, I'm not making any money, I should at least get to go and see him. So I called up his assistant, his secretary and I said, can I come in and see Ace, I work as an intern, and she said, yes, Ace really likes to mentor new people. He wants you to stick with the company if you're good, and he wants to help you with your career, even if you're not here so I get to go up into see him. And this guy is so typical Wall Street, you go into this giant room, huge desk, all the traders are sitting around the desk, he's at the head of the desk, not sitting in an office by himself, with the traders, high action, literally people with two freakin phones in their hands, one of the 10 people whose elbows on their shirts were clearly rubbed off on these nice elbows, because they were just on the phone with their elbow on the desk so much of the day. I go in, I sit down with him, he tunes everyone out, he looks directly at me and you, you got his full attention. He's not messing with the phone. He's not talking to the person next to him. He's not, he's not trying to close a deal or anything. He's there and I get to ask him all these questions. And I look at my notes, which I still have to this day in my NYU notebook. And it's questions about how he got started. And he tells me that he started on Wall Street as just a person with a low paying job, but he kept on working his way up. And then he finally got to work with the boss as an assistant. And I did everything for the boss until he became the boss himself. And I read that in Fortune magazine in Forbes magazine and then I asked him about how he believes in hiring. And he talked about how he liked to have people with PSD degrees. And I knew what that meant before he even gave me the punchline to that joke. It's like poor, smart and determined to be rich degrees better than MBA, I knew all that stuff. And at the end of that session, I had learned nothing. The conversation was stilted, he finally stands up, he puts his hand out in front of him, says, well, Andrew, it's been great knowing you and I know what that means. It's like, this is going nowhere and it's too painful for me, he wants me out of there. And he said, I see what you're looking for. I got advice that maybe could help you. Someone once told me if you do what you love, you never have to work a day in your life, okay, goodbye. And I'm walking out of there gone, I got a fortune cookie, I got nothing new that wasn't in Forbes magazine. Nothing that I couldn't have seen a fortune cookie, nothing that changed my life. And I beat myself up so much for that missed opportunity and said, I'm never going to miss that opportunity again. This is a person who wanted to mentor me, wanted to be there for me, and I missed it. And what I realized I should have done from the beginning was not asked him all these questions that show that I'd done research or asked him generic questions, I should have come out here is my mission for the conversation first to myself, and then to him and say, Alan, can I call you Ace great Ace, I'm working here for free because I believe in the energy of Wall Street. I'm working here because I believe in you and what you've built here. I would like a career that makes sense. I don't even know where to start. Where should where would if you were in my position, where would you go? Or when you were getting started how did you know that the person you ended up working for and devoting a big part of your career to was the person to attach yourself to? Crank, now here's another question. After I finished this unpaid internship, I need to make some kind of money. I like I have to tell you, I'm a little driven by money. And I know that it's okay because you believe in people who have the PSD degree I have that I have this determination to be rich, as much as I have this determination to do the work that involves numbers. What should I do next, so that I can make money and feel energized, but also set myself up for success. So bottom line, be clear about my mission and then bring it out to him. Now, would he have preferred that I said, here's where I am guide me with specifics versus I did the research tell me about your life, of course, he would have preferred that. My problem was and I think a lot of interviewers and a lot of conversationalist do not believe that they should bring themselves in their needs into a conversation and that's the wasted opportunity. Or the other part is they bring too much of their needs and they come across as too needy and the figuring out of how I can bring my own needs, and then make sure that it also satisfies the other person's needs. That's the magic of a conversation that will make people want to talk to you over and over again and where the conversation is fruitful. And you'll want to do it over and over again.


Jay Clouse  10:06

I love that because I think a lot of people do get caught up in, oh my gosh, I've got Ace's attention, I need to make this valuable for him. And then you forget that he knows he's doing you a favor to some degree and he wants it to be useful to you. That's how he's going to know that he paid off his end of the bargain, that's the value for him. I think a lot of people get wrapped up in that, and they don't end up sharing their agenda. And I think like you said, if you if you bring out and explicitly say, this is what I'm trying to get out of this and record and show, like, I know this is about me but that's kind of the premise that we met on this floor in the first place. I think that avoids the fear of like being too selfish.


Andrew Warner  10:43

Right. Now, does that mean that it's all me, me, me, me, me, me, me. And he's got to solve your problems and help you do your taxes? Obviously not but he's there with the reason. And if you've taken some interest in his background, and you understand a little bit about where he's coming from, you don't have to ask the same stupid questions, you can now go a little deeper.


Jay Clouse  11:00

What does it feel like to have 2100+ recorded published podcast episodes?


Andrew Warner  11:06

It feels great, I'll tell you why. Whenever there's something that I'm curious about, how, how did I get someone to say something? How do I, how did that one person respond to that? What if I said this? What would people say? I've had all my interviews transcribed, I get to go back and see. So I don't wonder I have this, this laboratory of conversations that I can go back and look at. I also fantasize and believe that at some point in the future, all of this stuff will be analyzed by software and made even more useful than it is today. And if I could project even further in the future, I do these interviews with the understanding that at some point in the future, all of these interviews will be put on a chip in people's brains. And if they want to learn from entrepreneurs, there's no better resource of listening directly to the entrepreneurs talk all about their lives and how they did it, than these sets of interviews that I've done over the last 14 years. I love that, I love that concept and that like shared global knowledge base of all of this. I feel like even still, podcasting isn't this magical time where people don't think about it as like, a record of note as much as they think of other mediums like this is going to be found and scrutinized potentially. And there's just so much rich content that comes from that. There's also about a lot of bad content that comes from that. But there's got to be so much good stuff out there basically buried. We've really benefited over the years with podcasting with not having our numbers be public. So you know what, you see a YouTube video and you decide whether to watch it or not partially based on how many people have watched it before you you don't give it a chance on its own. And that hurts a lot of content creators, it hurts a lot of viewers with podcasting that doesn't exist, there isn't a number on your head. There isn't a number of likes, number of listens, a number of anything, people get to judge it on its own and so that's a benefit. The other benefit we've had is the contents been so buried deep in the conversation, that people feel very comfortable in podcasts. I look at my interviews and people have asked me Andrew, why don't you go 15 minutes, it's largely because it takes a good 15 to 20 minutes before people feel comfortable. And often at minute 40 or 50 is when they reveal the thing that they didn't realize that they that they are revealing. And that's where the magic happens. And the only way we could have that is if there's a sense of mystery around it. We all know everything's online and everything but when was the last time you heard someone say something in a podcast that became scandalous? Hardly ever, but they say it on YouTube? Absolutely. They say it in a press conference? Absolutely. They do it on Twitter? Absolutely. But in a podcast, we're not there yet. And so it gives us this this time to just have a conversation and not feel so judged and so stilted and so performative. It's a magical time.


Jay Clouse  13:56

Somebody said to me, they said, you know, two generations ago, to be in a conversation with somebody, you had to be in the room, like they knew that you were listening that conversation and now that's not true. And I think about that all the time because what a magical time that our mentors can be people we never even meet. But we can learn so much from them and so much about them based on the work that other people do.


Andrew Warner  14:19

I went to college with the idea that this would be a place for me to learn from the greats to bad ideas back and forth that impacted my life. It wasn't, it was all about what kind of BS could you do to get the grade that you need and I hated the people had that attitude because I was paying the money out of my own pocket. I got no no financial assistance. So I want to if I'm paying that much money to get as much value and I'm not here for the BS to get the grade. What I found in podcasting is what I was looking for there where I could read Seth Godin's book and then get on his video call with him and say Seth, but this doesn't seem logical to me, it feels so good when I read your book. Why would I do that?


Seth Godin  14:58

Tribe is nothing but a tactic, a method and approach to getting change to occur. And that change could be growing your business or getting elected or making the world a safer place. But all of those things now require a tribe.


Andrew Warner  15:15

So I've got, I'm a big follower of business people. I've got books by, by Ted Turner's you could see here, Sam Walton, I've studied forever, here's mouth of Malcolm Forbes, who I love. And I don't see that these guys created tribes, which isn't to say that they have it, I just don't see it, am I missing something? And then to have him argue back to have them say, you know, everyone is a content creator, we all need to have communities and for me to say communities, entrepreneurs have businesses to run and communities on top of that, and they have to manage their own internal culture, and to argue it until we come to an understanding that makes sense to me, that is a gift. Now most people read a book and they'll go, this is amazing. My life was deeply impacted. They think their lives were changing, maybe it was. But it's not until you get to actually have a conversation with the person whose ideas you've picked up that you really get to grasp them that you really get to challenge them. And that's I think, the magic of podcasting. Anyone can be a podcaster today, anyone can interview people that they admire, and then go beyond accepting other people's information and say, instead, I see where you are, I see what we've done, I want to go deeper, and I need to make it a little bit more useful to me more meaningful to me.


Jay Clouse  16:28

After a quick break, Andrew and I talk about how to have better conversations without asking more questions. And a little bit later, we get into some of the techniques he's learned as an interviewer. So stick around and we'll be right back.  Welcome back to my conversation with Andrew Warner. To this point, when Andrew is talking about his podcast, he's been using the word conversation a lot, much more than he uses the word interview. This is an intentional choice and it ties back to the premise of his new book, Stop Asking Questions. And I have to say the idea of not asking questions is a little confronting as an interview and a host of a podcast. So I asked him to explain how he can tap into someone's wisdom and knowledge in conversation without asking questions.


Andrew Warner  17:13

The problem with asking questions is we all come across as too whiny. We think that if we're trying to learn from someone, we should be asking questions like, what did you do? How did you do it? What did you do next? What should I do? What did I what's not working here? We think that's the right approach. The problem is, we come across as very needy people asking too many questions. Just really at some point, you feel like it hurts your brain to be asked questions all the time. What most people want is not to be pounded with questions, but to have a real conversation. And what a real conversation involves is a little bit of the interviewer or the person who's trying to learn, asking questions, a little bit of them sharing their own experience, and a little bit of them guiding. And so it's not enough to just keep saying, what did you do? How did you start your first company, you have to sometimes say, I started a company, here's what happened and it failed, you have to sometimes instead of asking the question rephrase it as a statement and say, tell me how you got started. And through a combination of different approaches, we end up with a conversation that feels more real. And the reason that I named the book Stop Asking Questions is because I was just so bothered by how much of conversation skills seemed so natural, but it's not, it goes against what your intuition tells you. It goes against what your teachers have told you. It goes against what what you've learned is the right way to do it. You're not supposed to say to someone come sit down with me and I will tell you what to tell me. But it works to say now tell me where you got started. People need that kind of guidance.


Jay Clouse  18:44

It strikes me that part of the reason it's hard to get into that flow for people who haven't had years of practice at it, is because you can be nervous, you can be starstruck, feel like who am I to talk to this person as if we are on the same plane? How and when did you get over the feeling of starstruck or nervousness when talking to people who have large success or accomplishments or public profiles?


Andrew Warner  19:13

I literally don't if I ever, if I ever stopped feeling starstruck, I should be talking to other people. I should stop what I'm doing. It's an indication that I'm talking to the wrong people. You have to feel starstruck, you have to talk to people who you're an absolute awe of, and if you're not, what's the point? And so then the next thing is, if you are an off someone, how do you have a conversation that's meaningful and not one where you just say, I'm in awe of you, I can't believe it I'm in this, right? What do you do? And for me, having done this now for years, whenever I feel nerves or starstruck or anything that would get in the way of that conversation. I have a few tools that I go to one of them is to say, what am I here for? What is that higher mission that is so urgent that I have to talk to this person and I bring that up in my own head so that I'm aware of it. And I bring that up to my guests. I have to tell you, when I was in Estonia, I was talking to entrepreneurs in their office, these people at the Estonian entrepreneurs are just amazing. Guy built a billion dollar company off of ride sharing called Bolt, I'm talking to him, he's a kid, he's just so amazingly smart so accomplished, one of the creators of Skype, I get to interview him. I'm in awe and I also feel out of place because I'm in Estonia, interviewing people. And I had to come back and say, why why did I come here? And I realized I came here because I want to see how entrepreneurship, online entrepreneurship specifically works outside of the tech ecosystem that I know. So that I know that I've got more options in the world, so that I have more inputs in the world, so that I actually get to know people beyond the same people that I see over and over again, and I have a diverse way of thinking and more options for myself, who knows, maybe my wife and I want to go to Estonia at some point and live and have other options. And so coming back to all that makes me pick a moment, and then have a real conversation that gets back to that bigger, higher need.


Jay Clouse  21:02

It's actually very comforting because I get nervous before every interview of the show. I have people ask me, pretty consistently, they'll listen to episode one of the show, which was with Seth Godin. And they'll say it sounded like you guys had such a relationship, like, how did you talk to stuff like that? And I think over the years, I've realized, people don't want to feel othered when you're talking to them, and talking up to them, but it feels uncomfortable in a way. It feels like performance, I sometimes feel like I am in performance mode, which is exhausting at times. Do you feel that when you're interviewing people and it feels a little uncomfortable?


Andrew Warner  21:37

No, not really, not anymore. I did when I was doing the interviews live. And I wanted everyone to like me and stick around because I could see my numbers in real time. And if people disappear, then I felt like I wasn't doing well so I do something shocking to keep them there. I did have this experience last night where I was having a conversation with a new friend here and I realized I wasn't on, I didn't have my high energy. Truthfully, we were getting get a little later than I expected so I sat down, had a beer with my wife and that kind of put me in a mellower mode. And I know that the reason that you want to hang out with me was because every other interaction we had was so like energetic and on. And I could see that people gravitate to that. And I wanted to be that for him but I've realized over the years that if I fake that energy I come across as a real idiot, I come across as somebody that I feel embarrassed to be led to even be near. And so I've just learned, it's okay just be here. If David's not happy with this, if this is not a good dinner, it's fine. I'm not, I'm not a terrible person for it. Same thing with interviews, if this person that I'm interviewing does not like me, it's okay. They're going to be other people. That's not the only interview that I'm going to do. That's not the only dinner I'm going to do. It's not the only conversation I'm gonna have. And having that attitude helps reminding myself of how when I try too hard I come across as as a jerk, helps.


Jay Clouse  22:55

Talk to me about when you began to identify as an interviewer if you do identify as an interviewer.


Andrew Warner  23:04

Reluctantly I do. I think some words make more sense to use because everyone accepts it. And so yes, I would say I'm an interviewer. I just don't feel that way, I feel like more of a conversationalist. I hate when it feels like something you'd see on television where it's an interviewer, but okay, fine. I'll go with it. I'll tell you what word I don't accept, ever. This is such a small thing. I don't think anyone's ever noticed it because I've been just, I just shy away from it. I never say the word show, I just am not a show person.


Jay Clouse  23:33



Andrew Warner  23:33

Yes. I don't think of it as show I think of it. Like if I am not a showy person, I'm not in the show business. I want to have real conversations. I don't know if that's a show.


Jay Clouse  23:43

You're interesting.


Andrew Warner  23:44

And so I intentionally when people say, Andrew, I really liked your show, I just will let it hang. I won't even address it. I won't correct them or anything because it's too involved, but I'm sidestepping it and moving on.


Jay Clouse  23:54

Well, I asked the question, not because I'm hung up on the word interviewer so much as you could identify as an entrepreneur, you probably do to some degree, I'm trying to get at when you started the show, you likely didn't realize that was going to be the business that it is today. And I'm curious, when you did start to have that realization in the show, sorry. And


Andrew Warner  24:15

It's okay.


Jay Clouse  24:16

Mixergy started to be that thing for you.


Andrew Warner  24:18

I always thought it would be a stepping stone towards something else. I wanted it to be about interviews that then led to courses taught by real entrepreneurs. And truthfully, that was a big part of the business. I think what I should have done differently was just separate that courses part out of out of mixergy the interviews. I remember talking with this guy, Gonzo, the founder of what used to be startups.com but I have lost touch with him now. Every time he had a product brand extension, he would put it on its own domain and I asked him why. And he gave me some books to read about branding and essentially left me with this message that you need to create a different brand for different products because people can't put two things in their heads associated with the same name. And so I probably should have taken the courses part of the of Mixergy and turned it into its own site. And, you know, on Mixergy left it as an interview thing that then would direct people to the courses instead of saying, it's interviews. And then by the way, we've got courses with the idea that eventually it'll be courses first but also we have interviews. I don't know if that makes sense but I think that that was that was the vision. That was why I started doing the interviews, then I took the whole thing online with the idea that I would eventually also bring this educational component online, and I did and it's still there, and it's still going strong, but I wouldn't want it to go stronger.


Jay Clouse  25:38

Talk to me about that. What did that look like in your mind at the time, and how did that change?


Andrew Warner  25:44

I thought what it would be is Skillshare. What Skillshare did is is magical. They brought practitioners on to teach what they do best in my mind that should start, I would have wanted to start that with entrepreneurs on my platform, and then expand it to others. Skillshare started with a broader collection of people, they'll have artists on, teach how to draw, teach how to paint in addition to I took a course on how to give massage, I can give my wife a massage, you know, great course, it's great product, you can see the practitioners, you can see sometimes their video quality stinks, but they are the experts in their field. And I liked that I liked that approach. I think the way they did it was was great. I like how there's flooding revenue with the people who are on their platform teaching that was the approach that I was aiming for,


Jay Clouse  26:32

Does anything stand out as an inflection point where if you would have made a different move or a different decision, maybe that future would have played out?


Andrew Warner  26:41

Not exactly, I do see some inflections that are meaningful and were tough at the time, I'll give you an example. One of them was just recording my first interview, using the junky mic that I had around the house that in retrospect is hard on the ears. But I had it and I recorded it and I had the confidence to publish it because I was earnest in what I was trying to understand, that was one. The next one was charging, I wanted to have a direct relationship with my audience, a lot of people want to know how I get sponsors. I'm much more excited about the effort that I had to put in to charge my own audience, because I wanted to have a direct relationship with them a direct financial relationship with them and that took me so long to implement partially because I had mental blocks about it. I had this loving relationship with my audience of real entrepreneurs building things that I was proud of, I would be able to walk into a tech event and see people there who knew what I was doing and we're listening. I remember I moved to Argentina, Brian Armstrong, who's now the founder of Coinbase was one of the first people reached out said I know you, I know your work, I know you're I want to I want to get together and we got together it was this great set of people who are listening and it was it was magical. I was worried about charging them and ruining that magic. But I also knew that the best way to understand an audience was to have a direct relationship where I'm selling them things and that that was a real pain point. When I launched it, people were angry with me and the people who I loved were angry with me, my audience but that was worth it. That was good inflection point. The last one was where I was trying to figure out, I started out by just selling my interviews because I had them and I wanted to sell something and I knew I could improve but I needed to figure out what the better thing was. And I remember talking with my friend, Noah Kagan, who now runs app Sumo and saying, Noah, how do I know what to create? What to charge? And Noah is so good about frameworks. His answer to that was not advice but let's pull up a spreadsheet. And his spreadsheet was list all the things that you could create. Now let's in columns next to each one of them and say, on a scale of I think it was like 1 to 10, how hard is it for you to create? On a scale of 1 to 10, how promising is it to succeed, and on a scale of 1 to 10, we had all these different things. And then we finally had a set of options that I could create that mathematically made the most sense. And I tried them all and I tried and tried and tried until we ended up with courses and then courses did take off. I think they did well. My only frustration is they didn't do even better. But I think that's true for everything in my life.


Jay Clouse  29:09

I think that's true for most people with most things that they do because even even the things that go really well, we have like a never ending, always moving goalpost, right? And we think well,


Andrew Warner  29:20

I think so.


Jay Clouse  29:20

now I've changed my aspirational set of who I'm looking up to and their success. And so now, even though I might have matched what I was previously trying to do, my expectations have escalated.


Andrew Warner  29:32

You know what I had this experience the year before COVID I decided I would run a marathon on every continent and I'm persistent. So when I was told I couldn't run on Antarctica without giving more notice and waiting longer, I started making phone calls. Is there someone who could get me on? Can I get on a boat? Can I get on a cruise ship and then find a small boat off the cruise ship that will let me on Antarctica just so I can run my marathon on my own. That was the hardest one all of them were which were tough, but that was the hardest one. I finally get down to Antarctica. There is no marathon by the way on Antarctica that I could apply for it was just all packed for years in advance. So I get to run a marathon by myself, I have this team of people who are making sure that I'm safe and don't fall into crevasse. Is that what it's called the cracks in the ice? They're so supportive, they put up a sign us out of snow that said Marathon for Andrew, they when I finished, they gave me a, there's no gold medal for a guy who's running a marathon by himself. They said, well, you also won, they took the lid off a pickle jar, and they attached a shoestring to it. And they made a gold medal for me as the person who won the one man marathon and I videotaped the whole thing. And you could see me looking at my action camera as I crossed the finish line going, I can't believe I did it like a year of hard work. I can't believe I did it. And if you look at that, you can see it's on YouTube. I finish and I say, what's next? Like finish the whole hard thing there's no, now I've earned this amazing meal that I know there's going to be there. Now I've done it, I could relax for a little bit and actually take in all the snow. It's, what's next?


Jay Clouse  31:08

That's the thing, that is it. So many people feel that all the time. I feel that all the time. It's always what is next. It's never, let's reflect and celebrate these wins and if I do, it's ever so momentary. I've actually thought at times that I might be eliminating my ability to have memories because I am so not present in the now and thinking about the what is next.  When we come back, Andrew and I talk about his experiences with burnout in his experience writing this book, Stop Asking Questions, right after this. Hey, welcome back. Right before the break, I was actually complaining to Andrew that sometimes I feel like I'm so focused on what's happening next, that I failed to be present, and appreciate what's happening right in front of me.


Andrew Warner  31:54

I've lately been much more so in the now than in, I can't believe I did that in the past or I want to do that in the future. Partially because I am a little burned out on trying. And I do find myself being super engaged, super like that persistence of mine works really well for me, it's what allowed me to power through the early days of interviewing when people didn't know what a podcast was, and get them to say yes to my podcast and ask them to promote and get them to promote, right? It's that persistence thatlet me go for 14 years. It's that persistence that before that when I was doing an online greeting card company allowed me to force my way through business, and make that thing work out really well. And then at the end of the greeting card company, I just said, I got nothing else I'm done. I think that I'm going to I've been at a place since frankly maybe COVID or so where I just said, I'm tired of pushing myself to do more, I just want to be for a little bit. And it's been pretty good. The only thing that I pushed myself to do was write the book, which was real murder. I like murdering everything on my to do list because it was so tough to write.


Jay Clouse  33:00



Andrew Warner  33:01

I knew what I wanted to say because I've been doing these interviews and I've been recording the techniques I've used to do interviews, but a few things would happen. One is I would struggle to say it well on paper. And so having a weekly call with an editor where she would say well, what are you even trying to say here that you actually you're telling me you spent a whole day and you wrote nothing? What are you trying to say? And I say to her and she says okay, once you just go write that. So that eventually helped me get past it. Another thing that would happen to me is I get spun out of control when when I'm doing research. And so I say something like, I know that if you have a challenging question, you should put the question in somebody else's mouth.


Jay Clouse  33:42

Say more. What does that mean?


Andrew Warner  33:43

Okay, so the best example of that was I heard that Mike Wallace of 60 minutes was such an incredible interviewer. He even had the guts to say to Ayatollah Khomeini, you are a lunatic and I go, how did he say you're a lunatic to this guy who had taken would take an American hostages and suddenly became like a real danger, dangerous person for for the US when he took over Iran. And I went back and I had to go into the archives, and I found the old interview where he was sitting on the floor with Ayatollah Khomeini. And I wanted to see how did he ask the question, I didn't just listen to it. I had it transcribed so that I can follow every word and what he ended up saying was not you are a maniac, how are you a maniac? None of that. He said, Ayatollah, and then he said President Sadat called you forgive me his words, not mine, a lunatic.


Mike Wallace  34:33

Imam, President Sadat of Egypt, a devoutly religious man, a Muslim, says that what you are doing now is, quote, a disgrace to Islam. And he calls you, Imam, forgive me, his words, not mine, a lunatic. I know that you have heard that comment.


Andrew Warner  34:58

And then he asked the question and you could see I told Khomeini gone, that you see him fizzing. He's not even holding it back for PR purposes. You see him being angry. And then Sadat was killed not too long after that, right? But Mike Wallace was able to leave the country, why? Because Mike Wallace didn't say you're a lunatic. Now, would I tell the community have killed them right there? No, I don't think so. But it changes the dynamic and relationship when you say that, but he wanted to ask, are you crazy, instead of saying it yourself, you bring in someone else's word. So I knew that I needed to go and hunt that that clip down and really see is my memory right? I also wanted to prove that I'd used it and it helped and so I had to find an example. So now I'm going into the transcripts, I've got 1000s of transcripts, I go back in. And the one that I found was the one that I did with Ryan Hoover of Product Hunt, where I wanted to ask him the question that I knew that the audience would ask without offending him so much that he gets closed off and goes, Andrew just doesn't understand, he's a journalist, a mean, whatever, right? Or he's just a means friend so I went back. And the question that I wanted to ask was, it seems like you have more men than women? Why aren't there more more women on your platform who are creating apps or creating anything, you're supposed to be the creator space. And the way that I asked them was by going back through the archives of his site and finding somebody who in the early days had asked that question and looking at his response.  On that very first post on Quip that you announced the launch of the Linky Dink list. Chris Oscarson, Product Manager at Autodesk responded and said, you're a good guy, Ryan. And not to flag, not to flog a dead horse, but for the love of God, please invite some diversity into your contributor list. I'm happy to help with names and introductions. And you said right from the start, I hear you I know it's an issue and I'm working on it. I'm looking then at this list of people and I assume that the reason it was all guys is because that just happens to be who posted today. But then are you still struggling with the with finding females, with finding a diverse audience of submitters?


Ryan Hoover  37:01

It is a problem. Not with the site, no criticism of you. But frankly, if we can't get more diverse collection of people submitting links to new products, then how are we going to solve the harder issues of getting more diversity in the in the startup founder base, in the developer base, and so on.


Andrew Warner  37:21

Now, as a as an author, as somebody who has all these transcripts, I wanted to not say this is the way you can ask without offending people, I want to show examples of it. And that's where I would spend out of control going in and finding examples. And another example that I thought, it's not enough to have these two examples, I need $5, I know that this is done. And then Maryson, the editor who I was working with would say, Andrew, you have enough examples, people will actually trust it because you're saying it, because you're doing it based on your experience, you don't need every bit of proof that your experiences there. One example is fine. Another from another place is good. Now let's move on to the next thing.


Jay Clouse  37:56

Those examples did stick out to me in the book because I really appreciate that. It gives more depth to the person presenting the idea whether it's a book, a talk, and anything when you give specific examples, because you know that they're not just blowing smoke. It's like I have done


Andrew Warner  38:10



Jay Clouse  38:10

Here's what happened. It's it's


Andrew Warner  38:12



Jay Clouse  38:12

really where the credibility is, in my opinion, the book does a great job of that.


Andrew Warner  38:16

Thank you and it does a great job of that because I did go into that world where there's so many Jay, there's so many interviews that I had transcribed from history, they didn't even end up using because it became overwhelming to include it. But I would go back in and see how did Barbara Walters interview Richard Nixon after he was out of office and get him to admit that he wished that he had destroyed the tapes. How is it that that Lance Armstrong admitted to doping and how is it that Oprah Winfrey brought it up? At what point do you bring it up? Look, the whole thing would send me getting transcriptions, transcriptions, transcriptions, go into the archives and find this stuff. And a lot of this stuff might be on the internet one day and then off tomorrow when they got a cease and desist but I had to hunt it down.


Jay Clouse  39:05

I like these stories because you you went through Joe Rogan's transcripts to see how he does things and listening to those types of shows will think like, this is just a meandering three hour conversation. But you pulled out some real like themes, and why behind how these things work. And I won't spend a lot of time there because people should read the book and see what that's all about. There are no good books that I found before this on interviewing, and I mean that sincerely. People ask me, hey, how do I get better interviewing and I've said hire a coach. Because I just haven't seen it and I'm probably looking in the wrong places but this does a really good job of that.


Andrew Warner  39:40

Here's why there aren't. I bought the ones that exist. Larry King did years of interviews on CNN amazing people. He wrote a book called How to Talk to Anyone. I said, this is it. I go and I buy the book. I read every page of it. It is actually full of mostly his own stories of having conversations with people and little bit of technique. Barbara Walters did interviews with the heads of states for decades. She wrote a book, I think it's also called How to Talk to Anyone. I went and I, do you know how hard it was to get that book, it's not even available on Amazon, I had to go and locate it at a small bookstore, they accidentally mislabeled the book and they gave me the wrong one, I had to call them up and see if they could get the right one. Through the whole thing, I ended up with two copies of the book, maybe even three, and then I gave it to other people who thought it was important. I told them, though, before I gave it to them, it's not that important. She talks a little bit about her stories, talking to people in interviews, but mostly, she'll give things like, I'm not kidding you makeup advice, makeup advice from a woman who talked to heads of state, instead of giving you advice on how to have conversations, so why is that? Because up until that point, up until recently, you could not do interviews yourself. It's not like you could read Barbara Walters book on how she interviewed Richard Nixon and go great, now I'm going to call up Richard Nixon and interview him to using these techniques, or I'm going to go call up anyone and interview them, you didn't have that power. Today, we finally have that power. It's such a waste that all these great interviewers died with their techniques. It's such a waste, but you know what, now there's a time to do it. I've been doing these interviews for over a decade, I've studied these other people, this is the opportunity to finally write the book and to know that there's an audience for it. That's why there's never been a book like that before. And I wish there was. I will also say this, though, it's not just interviews with anyone. The other opportunity beyond podcasting is you get to talk to anyone, they are so much more accessible than they were before. And when you have that opportunity, it might randomly be that it's on a clubhouse session in the middle of the night, because they happen to be sitting in the hot tub and ready to talk, it might just be that they've invested in some new thing, or that they're doing a Twitter spaces, and now you get to talk to them out of nowhere, at that moment, that's an opportunity. If you don't want to call it an interview, to call it a conversation, maybe it's actually getting pulled side at a party, when you get to see somebody who's your hero. And instead of just chatting it up, you could do something meaningful. That's the power that we never had before and I want to seize it.


Jay Clouse  42:12

I love that makes so much sense. There was no incentive to write that book. Because there were not in numbers, people who


Andrew Warner  42:17



Jay Clouse  42:17

would or could do interviews, that makes a ton of sense. I'm listening through, Make Some Noise, the podcasting book right now, which is mostly really enjoyable. But the advice on interviewing so far has seemed to be like, follow your curiosity, prepare, but don't be stuck to your your questions. And like, that's good but that was like kind of it.


Andrew Warner  42:38

You know what, I don't know that book, I'm actually looking it up right now. I did read some of the NPR books on how they do things, hoping I would learn from them. And they have these great ones is even one that's in comic book form, which is amazing. The problem is, they are all about production values. And I think that's great. And your production values are great. I feel like that's a book you can benefit from and you say, okay, I can add this in, I want a great conversation, I will kill the whole frickin podcast, if it doesn't lead to a good conversation. And I will study to death, every part of conversations in interviewing, if it means that I could have a great conversation with somebody who I'd go out to scotch with or to wine with or to coffee with tomorrow. To me, it's not about the podcast, it's about the meaningful conversation that doesn't make you feel trapped, but makes you at the end of April, I had no idea. Nobody would ever talk about this stuff in public, they now list they'd now told me all this, and because they told me all this, they feel unburdened, they feel better, and we've got this bond, that's the magic that I want to have.


Jay Clouse  43:39

Tell me about that approach then when you're meeting with somebody that's not going to be an interview. It's just somebody that you may spend more time with in the future, you may not ever even see this person again. But for whatever the reason you're here for 30 minutes, and you can talk to him or not. How do you approach that conversation?


Andrew Warner  43:55

I think about what am I going through right now that I seriously wonder about and then I asked about that. And so it might be Olivia and I got into an argument because the two of us are in the house all day long and working together and how do I deal with that. And if they're in a long term relationship, that lasted for 30 years and that's what I care about, I'm diving into that. And it means a little bit of me admitting about what's going on with me and Olivia in our argument and a little bit of that. But it also means being curious about them. And then how do I drive that to a place where it's not just helped me with my relationship and now ah, we're hanging out and now I have to be Andrew's relationship coach and I never met Andrew, how do I make it cathartic for them that at the end, they go, I didn't realize that's how my wife and I had been together for so long. I didn't appreciate this part. This is tapping into something and I'm enjoying this and how does Andrew do it? And when you get into that, it's great. But it's it could be that, it could be the fact that suddenly have gray hair on my chest and go, what am I going to do and I look at somebody and I could see that maybe they're dyeing their hair, and I want to ask about that because I need a real human being not some dude on YouTube who's experimenting with hair with hair dye to talk to me about how they're dyeing their hair. It needs to be that the thing that's important. And so when I talk about some of these techniques, some of it has to do with the sensitive topics. If you just launch into I see you're dyeing your hair, it ruins the conversation, they clearly dyeing their hair because they feel sensitive back on gray for me to just jump in and do that it's awkward. And it's ruining the whole conversation and everything they're trying to communicate with their look, I want to know how I can do it in a sensitive way that lets it be an open conversation that's meaningful, that now taps into the thing I really care about today and lets them care and be as emotionally invested in it as I am.


Jay Clouse  45:37

You talked about your persistence and how that's been super helpful over your 14 year career. In preparing for this, I listened to another interview where you talked about there were times when you had to make like, uncomfortable asks, or like even asking the guests to share the show that in itself is like a small, uncomfortable ask you have to make, right? And I feel like in this world as a creator, there are just a ton of uncomfortable asks, you have to make pretty consistently. And I want to know if your persistence is innate and so those things came easily. Or if your persistence is something you're very aware of all the time, and you just are good at using your willpower to do those uncomfortable things.


Andrew Warner  46:13

My persistence is an iteration on the same thing over and over again. And so if you listen to my old interviews, I've always wanted the behind the scenes stuff to leak into the conversation. And if you listen to my old interviews, you will hear me specifically say to a guest, I need more guests on this podcast, who should I interview? Right? And what you will hear is people give me suggestions like, Elon Musk is a great guy. I don't know this guy who's now running Apple, we should go and get Steve Jobs. That would be amazing, I definitely listened to that. Well, no kidding you listen to that. But that's not what I'm getting at. What I need is more guests that I have access to. And so you can see me iterating that question until I get to the place where I say, I'm trying and so that they also don't tell me my uncle's a great person I start with, I'm trying to interview entrepreneurs in the tech space, who are building companies that we could all aspire to build. Who do you know, who's done that? Who should do this interview with me and could introduce me to? And now the wheels in their heads are turning and they will tell me about a few of their friends who've done it. And now I've got something not to get to that. It's not persistence in the sense of who should I interview come on, who should I interview and then tell me over and over again, it's the iteration the iteration until I say it in this magical open sesame way. And then I get my answer. And boom, now I've got more interviews than I can handle. And I now need to iterate on how I can improve the the guests that I get. That's the type of person that I've got. And man, if you're even an idiot, and you've got that kind of persistence, where you say, I know what I want and I need to do it. And then you're going to say, how do I change it tomorrow because that didn't work out? How do I change it tomorrow and you show up every day, you're going to out Fox and out perform the smartest people on the planet.


Jay Clouse  47:56

Beyond technique actually before technique, what hangs me up a lot of times is sometimes I know the move I need to make. And it is you know what I've talked to 70 people on the show, there were 10 of them that we had such a great experience, I bet they would do a collaboration with me if I asked, it still feels uncomfortable. And so I don't even make the action so technique doesn't come into play. Do you have those uncomfortable moments where you know what the answer is but you have a hard time taking that action? Or is, is that something that hasn't been a challenge for you?


Andrew Warner  48:29

It has one of the things that I do. And Mary, my editor who I would meet with every week just said this is a weird thing, just don't include in the book. One of the things that I do is when I ask, I will pinch my thigh so much it almost will go bruise just so I can take attention in my brain off of how uncomfortable I am asking the question and no one's noticing it. Like I could sit here and I will pinch it so hard that I can't pay attention anything in my head and let the words come out so I do that. I also if I try a few times and I get no's, the other thing that I do is I will find someone who said yes to someone else and say, I'm trying to improve. I'm clearly not trying to sell you on this thing. I'm trying to learn from you, you can see that what I am is someone who's trying to keep improving. You've done this collaboration with this other person. How did you decide to do it? What do you think I could do to get other people like you to collaborate with me? How do I and then you just go into it and it's it's an amazing process. When you finally say to somebody, I don't know you've done it. I'm trying, helped me out. They will they will talk you through it.


Jay Clouse  49:32

I love that so much of what you've shared here today it's about vulnerability and owning where you are and being honest about your intentions. But being clear about your intentions, even if they are you know, strictly your intentions and people being willing to meet you there and help.


Andrew Warner  49:49

They are and I think we need to accept it. We've gotten to a place where we can say I need to learn something, I will Google it. I need to learn something, I will YouTube it. I need to learn something, I will buy the book. I will buy the course, the one thing we still don't do is say, I need to learn the thing. That's the person who's done it, I'm going to go and talk to them. And once they are ready to do it, you need a set of skills. And that does take some time to understand. And that's that's what I've tried to do with the book. And sometimes it feels like, ah, why do we need skills in order to have a real conversation? Is it even worth it? I've got as much as I'm dealing with, how do I have better conversations by interviews? I've got kids who are five and seven. I need them to be better people and better conversationalist. And what I've learned is, if they ask somebody at a party that we bring them to, like, we just went to someone's party this past Saturday, if they go over and say, I want a doughnut, it's like, most like disgusting, rude thing. How do you raise your kids that way? People might do it, but there'll be disgusted by them. If they just say, can I have a doughnut, please? After seeing the donut there, that little change will make the other person melt. Now if you think logically, who cares? They came to your party, I want a donut is not that hurtful in the grand scheme of things. Just give him a frickin doughnut. If they say can I have a donut, please? It is amazing. My kid walked out of the room. He's five years old on the way out he goes, thank you for hosting us. That made the woman melt, it's just a phrase. And but if he learns that phrase, she's going to be happier to have him come back. And more importantly, next time she comes back, if she goes do I set up the slip and slide or not? She's gonna go that kid is so darn cute, I'm gonna set up this slip and slide, if you learn how to have a conversation with people as adults, and you can learn the magical phrases that make them feel like you care and also not drained them, but give them life. They're gonna say yes, I want to help them and want to come back and come back and come back. And that's that's what I've been studying over the last 14 years.


Jay Clouse  51:51

I cannot imagine conducting more than 2000 interviews. Andrew is one of the most experienced and skilled interviewers in the game today. And I really enjoyed learning from him. I picked up some great tips from Andrew's book, Stop Asking Questions, including a question that I now start every single interview with, how can I make sure that this is a great interview for you? And as I shared with Andrew, I've tried to find books on interviewing before and they just don't seem to exist. So if you're a podcaster, or even if you're just trying to become a better conversationalist, I recommend you check out the book, I've read it, it's well worth the price. It is available now on Amazon or at stopaskingquestions.co links to both are in the show notes. If you want to learn more about Mixergy then you can visit the website mixergy.com or subscribe to startup stories by Mixergy here in your podcast player. And hey, before you go. Do you want to be featured on a future episode of creative elements? I love hearing listener questions and we'll be sprinkling them into this show. Just visit creativeelements.fm to leave me a voicemail, or check out the link in the show notes. Thanks to Andrew for being on the show. Thank you to Emily Clouse for making the artwork for this episode. Thanks to Nathan Todhunter for mixing the show and Brian Skeel for creating our music. If you liked this episode, you can tweet @jayclouse and let me know. If you really want to say thank you, please leave a review on Apple podcasts. Thanks for listening and I'll talk to you next week.