The Nathan Barry Show
The Nathan Barry Show
055: Andrew Warner - Turning Your Podcast Into a Successful Business

Andrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business.

Andrew and I talk about his new book, Stop Asking Questions. It’s a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more.

In this episode, you’ll learn:

  • Why you need to understand and communicate your mission
  • How to get your guest excited about being interviewed
  • What to do instead of asking questions
  • How to hook your audience and keep them engaged

Links & Resources

Andrew Warner’s Links

Episode Transcript

[00:00:00] Andrew:
The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there’s enough interviews to last for a month, so I can be consistent, and the audience loves me.”

That’s great, but I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who’s suddenly done something, we should go ask to do an interview with them.

[00:00:32] Nathan:
In this episode, I talk to my friend, Andrew Warner, who I’ve known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots.

We actually don’t get into that in this episode, but it takes an interesting turn because we just dive right in.

Andrew’s got a book on interviewing. He runs Mixergy. He’s been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It’s more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you’ll like it. It’s a lot of what I’m going for on the show.

So anyway, enjoy the episode.

Andrew, welcome to the show.

[00:01:25] Andrew:
Thanks for having me on.

[00:01:26] Nathan:
There’s all kinds of things we can talk about today, but I want to start with the new book that you got coming out.

This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts?

[00:01:47] Andrew:
I have feedback for you. I have a thoughts on your program.

[00:01:51] Nathan:
I’m now even more nervous.

[00:01:52] Andrew:
I’ve been listening, and I’ve been following, and I’ve been looking for questioning styles. Is there feedback I could give him? I mean, I’ve wrote a whole book on it. I should have tons of ideas on that.

I don’t. Here’s the thing that stood out for me watching you. There’s an ease and a comfort with these guests, but I’m trying to figure out what you’re trying to do with the Podcast. What is connecting them? Are you trying to bring me, the listener, in and teach me how to become a better creator who’s going to grow an audience and make a career out of it? Or are you trying to learn for yourself what to do?

How to become closer to what Ali Abdaal doing, for example, or Sahil Bloom? Are you trying to do what they did, and grow your audience? Or is it a combination of the two?

I think the lack of that focus makes me feel a little untethered, and I know that being untethered and going raw, and letting it go anywhere is fine, but I think it would be helpful if you gave me a mission.

What’s the mission that Nathan Barry’s on with the Podcast. Why is he doing these interviews?

[00:02:56] Nathan:
Oh, that’s interesting. Because it’s probably different: my mission, versus the audience members’ mission.

[00:03:05] Andrew:
I think you should have a boat together and, but go ahead.

[00:03:08] Nathan:
I was going to say mine is to meet interesting people. Like that’s the thing I found that, podcasts are the pressure from two sides, one as a creator, as an individual online, like I’m not going to set aside the time to be like, you know what, I’m going to meet one interesting person a week and we’re just going to have a conversation riff on something like that.

Doesn’t happen the times that, you know, the years that I didn’t do this show, I didn’t set aside like deliberate time to do that. And then the other thing is if I were to set aside that time and send out that email, I think a lot of people would be like, I kind of had to have a busy week. I don’t know that I’ve, you know, like yeah, sure.

Nathan, whoever you are. I did a Google search. You seem moderately interesting. I’m not sure that I want to get on that.

Like a, get to know

[00:03:58] Andrew:
They wouldn’t and it would be awkward. And you’re right. The Podcast gives you an excuse. I think you should go higher level with it though. I think you should go deep to the point where you feel vulnerable. I think what you should do is say something like this, isn’t it. You have to go into your own into your own mission and say, this is what it is.

And just, so let me set the context for why this matters. I think it helps the audience know, but it also helps you get better guests to give better of themselves. I talk in the book about how I was interviewing Greg spirit, Dallas, the guy who created jib, jab, you know, those old viral video, it was a fire video factory that also created apps that allowed you to turn your yourself into like a viral meme that you could then send to your friends.

Anyway, he didn’t know me. He was incredibly successful. He was, I think, person of the year, a company of the year named by time. He was on the tonight show because he created these videos that had gone viral. And yes. He said yes, because a friend of a friend invited him, but I could see that he was just kind of slouching.

He was wearing a baseball cap. It wasn’t a good position. And then he said, why are we doing this? And I said, I want to do a story. That’s so important. That tells the story of how you built your business. Yes. For my audience. So they see how new businesses are being built online, but let’s make it so clear about what you did, that your great grandkids can listen to this.

And then they will know how to great grandfather do this and put us in this situation. And that’s what I wanted. I wanted for him to create that. And he told me that afterwards, if he had known that that was a mission, he wouldn’t have put his hat on. He said that after that, he started thinking about the business in a more in depth way, visualizing his great grandchild.

And then later on, he asked me for that recording so that he could have it in his family collection. So the reason I say that is I want us to have a mission. That’s that important that yes. You could get somebody to sit in front of the camera because you’re telling me you’re doing a podcast, frankly.

Right. You’re with ConvertKit they’re going to say yes, but how do you bring the best out of them? And that’s it. And so that’s why I’m doing this. And so one suggestion for you is to say something like.

I’m Nathan, I’ve been a creator my whole life, but I’m starting from scratch right now with YouTube.

I’ve got 435 people watching YouTube. It’s not terrible, but it’s clearly not where I want to end up. And so what I’ve decided to do is instead of saying, I’ve created the book authority, I wrote it. I’m the one who created software that all these creators are using a ConvertKit. Instead of, instead of allowing myself to have the comfort of all my past successes, I’m going to have the discomfort of saying, I don’t know what it’s like.

And so I’m going to bring on all these people who, because maybe I’ve got credibility from ConvertKit are going to do interviews with me. And they’re going to teach me like Alia doll and others are going to teach me how they became better creators, better business people. I’m going to use it to inform my, my, growth on YouTube.

And by the way, You’ll all get to follow along. And if you want to follow along and build along with me, this is going to come from an earnest place. Now I’ve obviously gone. Long-winded cause I’m kind of riffing here, but that’s a mission. And now we’re watching as you go from four to 500, now we care about your growth.

Now there’s someone giving you feedback and more importantly, there’s someone who then can go back years later and see the breadcrumbs. Even if the whole thing fails and say, you know what?

Nathan made it in virtual reality videos. And he’s amazing. But look at what he did when YouTube was there. He clearly didn’t do it, but he aspired right. I could aspire to, if I don’t do it, I’ll do it in the next level. That’s that’s what I’m going for with it. I talk too much sometimes and give people too much, too much feedback. How does that sit with you?

[00:07:14] Nathan:
I like the idea. I particularly love anytime a creator’s going on a journey and inviting people along for it, right. When you’re sitting there and giving advice or whatever else, it’s just not that compelling to follow it unless there’s a destination in mind. So I did that with ConvertKit in the early days of, I said, like I called it the web app challenge said, I’m trying to grow it from zero to 5,000 a month in recurring revenue.

Within six months, I’m going to like live blog, the whole thing. people love that another example would be also in the SAS space, but, the company grew, they did a customer support software and they, I think. They were going from 25,000 a month to 500,000 a month was their goal. and they even have like, in their opt-in form, as they blogged and shared all the lessons, it had like a progress bar.

You’d see, like MRR was at 40,000,

[00:08:08] Andrew:
Every time you read a blog post, you see the MRR and the reason that you don’t remember what the number was is I believe that they changed it, you know, as they achieve the goal, they, they changed it to show the next goal on their list. And yeah, and you’ve got to follow along now. Why do I care? The groove, HQ or groove is, is growing a competitor to Zendesk and help scout.

But now that I’m following along, I’m kind of invested now that I see how they’re writing about their progress. I really do care. And by the way, what is this groove and why is it better than help scout and the others? Yeah. I agree with you. I think that makes a lot of sense. I think in conversations also, it makes a lot of sense.

I think a lot of people will come to me and say, Andrew, can I just ask you for some feedback? I’m a student. Can I ask you for support? It’s helpful for them to ask, but if they could ground me in the purpose, if you could say to somebody I’m coming to you with these questions, because this is where I’m trying to go, it changes the way that they react.

It makes them also feel more on onboard with the mission. I have a sense that there is one, I’m just saying nail it, you know, who does it really good? who does a great job with it is a Jordan harbinger. He starts out his each episode is almost if you’re a fan of his, it’s almost like enough already. I get that.

You’re going to do an opt-in in the beginning of the Podcast. I get that. What you’re trying to do is show us how to whatever network now and become better people. But it’s fine. I’d much rather people say, I know too much about what this mission is. Then I don’t.

[00:09:26] Nathan:
Do you who’s afraid anyone else tuning in? What, what is Jordan’s mission? What would he say is the mission that

[00:09:32] Andrew:
It’s about, see, that’s the other thing I can’t actually, even though I’ve heard it a billion times, he’s adjusted it. It’s about, self-improvement making me a better person better, man. And so the earnestness of that makes me accept when he brings somebody on who’s a little bit too academic who’s, Jordan’s interested in it or a little bit too practical to the point where it feels like I’m just getting too many tips on how to network and I don’t need it, but I’ve got his sensibility.

He’s trying to make me a better person. And so I think with interviews, if you, if you give people the, the mission, they’ll forgive more, they’ll accommodate the largest and it does allow you to have a broader, a broader set of topics.

[00:10:14] Nathan:
Yeah. I’m thinking about the mission side of it. Like all of that resonates. and I love when an interview is questions are Like are the questions that they specifically want to know? It’s not like I went through my list and this seems like a good question to ask instead. It’s like, no, no, no, Andrew specifically, I want to know what should I do about, this?

And I’ll even call that out in a show and be like, look, I don’t even care if there’s an audience right now. Like this is my list, you know?

[00:10:41] Andrew:

[00:10:41] Nathan:
But the, like if we dive into the mission, the one that you outlined doesn’t quite resonate. And I think the reason. I think about, creators who have already made it in some way.

And it starts to lose that earnestness. Like, honestly, I’m not that interested in, in growing a YouTube

[00:11:00] Andrew:
I don’t think that that’s I don’t think that that’s it for you. It’s true. That’s a little bit too. I don’t know. It’s it’s a little, it’s a little too early in the career. There is something there. I don’t know what it is and it can’t be enough. It can’t be enough to say I need to meet interesting people because that’s very youth centric and I’m not on a mission to watch you, unless you’re really going to go for like the super right.

And we’re constantly aspiring, inspiring. the other thing it could be as you’re running a company, you’re trying to understand what’s going on. No Kagan did that really well. I actually have the reason that I know this stuff is in order to write the book. I said, I have all my transcripts. I can study all the ways that I’ve questioned, but I also want to see what other people have done.

And so Noah Kagan did this interview with an NPR producer. I had that transcribed to understand what he did and what he learned. One of the things that he did in that, that made that such a compelling interview is. He was a podcaster who wanted to improve his podcasting. And he, I think he even paid the producer to do an interview with him on his podcast so that he could learn from him.

Right. And in the process, he’s asking serious questions that he’s really wondering. He’s trying to figure out how to make a show more interesting for himself. Now. Clearly someone like me, who wants to make my Podcast more interesting. I’m like mentally scribbling notes as I’m running, listening to the podcasting.

Oh yeah. The rule of three, like what are the three things you’re going to show me?

Well, yeah, at the end he did summarize it and he did edit. I don’t like the edits at all because the edits take away some of the rawness of it and the discomfort which I personally enjoy, but I see now how he’s editing it out.

And it’s, it’s interesting to watch that progress.

[00:12:32] Nathan:
Yeah, I’m thinking through. The different angles that I could take with this. cause I like it and I feel like there’s a, a thread that’s not quite there. And I felt that on the show. Right. Cause people ask, oh, why are you having this guest on versus that guest? and it is that like, I, I find them interesting.

There’s also another angle of like probably half the guests maybe are on ConvertKit already. And so I want to highlight that. And then the other half of the guests aren’t and I want them on ConvertKit and so that’s an, you know, an incredibly easy, I can send you a cold email and be like, Andrew switched to ConvertKit.

Right. Or I could be like, Hey, you know, have you on the show, we could talk. and we’ve gotten great people like in the music space and other areas from just having them on the show and then

[00:13:18] Andrew:
Can I give you, by the way, I know it’s a sidetrack and I give you a great story of someone who did that. Okay. it’s not someone that, you know, it’s a guy who for years had helped me out. His name is Bob Highler every week he would get on a call with me and give me advice on how to improve the business.

And then at one point he said, you know what? I need new clients. I want to start going after people who are, I want to start going after lawyers, helping them with their online ads, because lawyers aren’t, aren’t doing well enough.

He started doing all these marketing campaigns because he’s a marketer. And so one of the things he did was he got these cards printed up.

He said, they look just like wedding invitations, beautiful. He, he mailed them out to lawyers. He got one, two responses. Like nobody would pay attention to a stranger, even if they were earnest and sending those out. And he goes, you know, and then he gets on a call. He doesn’t even know what to say to people.

If he just cold calling goes, I’m going to try to do that. And Andrew, I’m going to do an interview show for lawyers. He picked bankruptcy lawyers. He started asking them for interviews. They were all flattered because they also want another good Google hit. Right. And so they said yes to him and he asked them questions.

Then I started learning the language. I forget all the different terms that he learned about how, about how they operate. But he said, inevitably at the end, they’ll go after it was done. And say, by the way, what are you. And then he’d have a chance to tell them. And because he’s built up this rapport and they trust him, they were much more likely to sign them.

He signed up his customers, just like that, just like that. It’s a, I think it’s an, it’s an unexplored way of doing it, of, of growing a business, taking an interest in someone, shining a light on them, helping them get that Google hit and helping them tell their story. And then by the way, will you pay attention to the fact that I’ve got a thing that if you like me, you might like also,

[00:14:50] Nathan:
So a few years ago, I was in New York and Seth Goden had come out to speak at our conference and he’d ever said, Hey, if you’re in New York and want to make the pilgrimage up to Hastings on Hudson, you know, of outside the city, like come up and visit. And so I did that and it’s so funny, cause it is like this pilgrimage to you, you like take the train up along the river. You know, I don’t know what it is an hour and a half outside of the city. and I was asking Seth advice at his office, about like how to reach more authors. I think that was the question I asked him specifically and he just, he was like, well, what do authors want? And I was like, ah, I, some more books I guess.

And he’s like, yeah know. And so like we went through a series of questions, but he’s basically what he came to was, find a way to get them attention so that they can grow their audience to sell more books. And he was suggesting a podcast is the way to do that. What’s interesting is that’s the side, like that’s the other half of it, right.

I want to meet interesting people. I want to, Like get more of those people that I find really interesting on ConvertKit pushed the limits of like, our customer base in, in those areas. And then the third thing is I want to do it in a way that’s high leverage in my time. Write of, I want to do it.

That creates something, for people watching and listening along so they can follow the journey. But I still don’t see,

I would say two thirds of that is about me, right?

[00:16:18] Andrew:
It’s not only that, but all these things are byproducts more than they are the clear goal. You’re going to get that. No matter what, if you just talk all day about what? No, not talk all day. If you do, what was it? I’m the founder of morning brew does nothing, but like a 15 minute, if that sometimes five minutes.

[00:16:37] Nathan:
Alex Lieberman.

[00:16:38] Andrew:
Yeah, just what, what goes on in his life now it’s changed over the years or so that he’s done it, but it’s just, here’s what we were thinking about today. Here’s how I’m deciding to hire somebody BA done. He’s just doing that. That’s enough to get attention enough to also broaden his audience enough to bring us in and then so on.

So I think if you just did nothing, but get on camera and talk for a bit, you’ll get that. But I think a higher leverage thing is to tap into that personal mission and let all the others come through along the way and all the other benefits, meaning that you will get to meet people and change the way you think you will get to get people to switch to convert kit.

And so on, by the way, that’s such a, like an impressive thing for you to admit, to say, I want to have these guests on because I want to assign them up. I think a lot of people would have those ulterior motives and

[00:17:23] Nathan:
Oh, no, you got to just talk about, I mean, that’s something you and I, for as long as we’ve known each other have been very, very transparent in both of our separate businesses and our conversations and it’s just, everyone wants that. Right? Cause they’re like, I think I know why Nathan is doing this, but he wants.

And that would be weird, but if we go to the mission side of it, there’s mission of like this, I’m going to improve the world side of mission, which definitely exists that can protect you. And I got my little plaque behind me. It says we exist to help creators are living. And so we can take that angle of it, thinking of like the, the goal journey side of things, since we’re just riffing on ideas.

One way that might be interesting is to make like a top 100 list of the top 100 creators we want on ConvertKit. And the whole podcast is about interviewing those people and reaching them. And, and so it could be like, this is what I’m trying to accomplish. And you’re going to learn a whole bunch along the way as a listener, but you, you know, we check in on that.

And then another angle that we could take that would be different is the, like we’re going together. We’re going to help the creator make the best version of their business. And so you make it more of a.

We’re both peers diving in on your business, riffing on it, you know, how would we improve it? that kind of thing.

[00:18:43] Andrew:
I think helping creators create a business, seems like something others have done, but not quite your approach, your style, the way that you will go and carve something is this is the thing that’s over your head that says create. Is that something you carved in your wood shop? Then I saw on Instagram.

Yeah, right. The sensibility of I’ve got to create it my way. Instead of that’s a pain in the ass, I got a business to run who like, right. You’re not going to see, for example, infusion soft, go, we need a plaque. Let’s go to the wood shop. No, you’re not. It’s just not their sensibility. Right. Coming from a sensibility of someone who cares about the details, who every button matters in the software, everything behind your shoulder matters to you for yourself, even the stuff I imagine.

If you look forward would have a meaning there, it wouldn’t be random chaos. Is it random chaos in front of, on the

[00:19:32] Nathan:
The desk is random chaos, but there’s a sign that says the future belongs to creators up there. And

[00:19:38] Andrew:
Okay. I think I might’ve even seen that online somewhere. So I think that coming, coming from the business point of view, With a sense of creator’s taste, I think is something that would appeal to a lot of people. For whom seeing, for example, my take on business would be completely abhorring. All I care about is where the numbers are and what it’s like.

Right. Well, even allium doll’s take on, it would not be, would not be right, because he’s much more about every movement needs to matter. He can’t just have a checkbox in notion it Ellis has to fire off five different other things that notion because otherwise you’re wasting time. Why type five things when you could type one, right.

It’s a different sensibility. And I think you’ve always done really well drawing in that audience. I remember talking to a competitor of yours who started around the same time, also done really well about why you were, you were really growing tremendously faster. and they said he nailed it. He nailed who his audience is.

It’s the bloggers. It’s these early creators who, who didn’t have. Who didn’t have anyone speaking for them. And you did that. And I think maybe that’s an approach to saying, look, we are creators. And the business of creation is, or the business of being a creator is evolving and we want to learn about every part of it.

And then it’s interesting to hear how somebody growing their audience in an interesting way. How is somebody thinking about writing? I love that you asked Sahil bloom about how long it took him to write. I know he talks about it a bunch, but it’s, it’s interesting to hear him go with you about how it is like a five hour, seven hour writing job for him, right.

To write fricking tweets. He’s writing tweets, right? You’ve got people just firing off the tweet. He’s spending five, seven hours on it. And, and he’s also not a guy who’s just like, right. It would be something if he was still in school playing baseball, and this is his intellectual, whatever. No, he’s now running in investments.

He’s making decisions. He’s helping promote his, his portfolio companies and he’s spending five hours writing and he’s doing it like one a week instead of one an hour. Right. It’s all very interesting. And that approach, I think, ties completely well with ConvertKit.

[00:21:41] Nathan:
Okay. So where does that take us on like the mission or the hook for the show? Cause we’re.

[00:21:48] Andrew:
Okay. Here’s what I would do. I would, I would just keep riffing go. My name is Nathan Barry. You probably know me from convert kit. I’m doing this podcast because I like to meet interesting people. And here’s the thing I’m trying to do or I’m I I’m doing it because I’m compelled to talk to these people who I admire.

And I also want to learn from them about how they create and just riff on it. Like every week, even have every interview have a different one, until you feel like, oh, that’s the one that feels just right. But if we just here, I want to have this person on, because I’m trying to learn this thing. I want to have this on because secretly I’m trying to see if I can get him to be at, see if I can get Ryan holiday to actually be on convert kit.

Right. Boom. Now, now we’re kind of following along as you’re figuring it out. And that’s also

[00:22:29] Nathan:

[00:22:29] Andrew:
The way, is Ryan holiday going to be on here or what?

[00:22:31] Nathan:
On the show,

[00:22:33] Andrew:

[00:22:34] Nathan:
Probably we were just talking the other day. We have a shared investment in a ghost town, So we, we often talk about that,

[00:22:40] Andrew:
Oh yeah. I’ve

[00:22:42] Nathan:
Other thing

[00:22:43] Andrew:
That ghost town. Oh, that’s a whole other thing I’ve been watching that

[00:22:45] Nathan:
I need to have speaking of the ghost town, I didn’t have Brent Underwood on because that Is an insane story of everything going on with town, but it’s just been building this massive audience.

[00:22:58] Andrew:
Who’s doing YouTube videos from there? He

[00:23:00] Nathan:
Yeah. And he’s now got 1.2

[00:23:01] Andrew:

[00:23:02] Nathan:
Subscribers on YouTube, like 2 million on

[00:23:04] Andrew:
I had no idea. I watched him in the early days of the pandemic go into this place by himself. Almost get trapped, driving his car to get there. Right. I go, this is fun content. And usually when you watch someone like that and good morning, America go, and I’m going to jump out of this thing.

And I’ve never jumped before, maybe whatever. I don’t know.

Yo, the producer’s not going to let you die. It’s fine. Here you go, dude. Who’s just trying to get attention for this thing. Cause he has some investors who he wants to make sure get what they want. Yeah, you could die. What the hell is you doing?

What? Like I’m going to, I’m going to go down this hole and see if there’s anything over you yet. Dude, you could

[00:23:41] Nathan:
Yeah. It’s, it’s pretty wild. I actually, some of the weeks that he don’t, he, that he didn’t post the videos. I’d like, texted him, be like, Brett, you’re still alive because you know, the video was the way that we knew every Friday, like, okay, Good Brent. Still alive, everything. Everything’s good. Anyway, I got to have him

[00:23:58] Andrew:
All right. If you do talk to, if you talk to Ryan holiday, I feel like you totally nailed his writing style, where you, you said in one of your past episodes that he can take a whole historical story, sum it up in two sentences to help clarify the moment that he’s writing about. And it’s like a toss away thing, right? Just toss it away and then move on and go, dude. That’s a whole freaking book. In fact, just turning the whole thing into just two sentences to fit in there would take silo, bloom five hours. You put it in a book with other, like there a bunch of other sentences. So that’s good. But here’s what I think you should talk to him about.

Or here’s my, my one suggestion. He has not talked about Marketing since he created, trust me. I’m a lot. Trust me. I’m lying, which was a phenomenal book that then I feel like he distanced himself from when he became more stoic and more intellectual. Fine. He is still a great, great marketer along your style, your tasty.

And in fact, he’s becoming the people who I can think of that are very, ConvertKit like philosophy in their creation plus promotion. He nails it, right? Art that takes so much pain that you’ve mentioned, and we’ve all seen it. He has boxes of index cards to create these sentences that most people would just throw away, not pay attention to, but are super meaningful.

And at the same time, he knows how to promote. He knows how to get his ideas out there. He knows how to sell a coin that says you’re going to die in Latin, that people put in their pockets that are more than just selling a coin. It’s selling this transferable viral, real life thing. Right. So anyway. And is he should be on a ConvertKit too.

[00:25:29] Nathan:
He is, he is

[00:25:30] Andrew:
Okay. Good.

[00:25:31] Nathan:
Half of his list started in Berkeley. The other half are in the process of switching over. So, you know,

[00:25:36] Andrew:
Okay. Yeah, that’s the hard part, dude. I I’m with infusion soft. I can’t stand them. If you understand how much I do not like them. I do I ever talk negatively about anyone. No. Bring up politics, Joe Biden, Donald Trump. I got no strong opinion about anything you talked to me about, about infusions. Ah, but the problem is it’s so hard to wean yourself off of these things because once you’re in a system, that’s it

[00:25:56] Nathan:
Well we’ll make it happen. W w we’ll figure out a way, but the new book landing page for it, I went on there and inspected element. It’s definitely a ConvertKit for them. I was pretty happy about it.

[00:26:06] Andrew:
Oh yeah, yeah, yeah, yeah. So truthfully it was, I said, I’m not going to school around here. It would have probably been easier for me to go with, with infusion soft because then we all we’d have to do with tag people who were interested. And then I could, I don’t want that. I don’t want that nonsense because it comes with overhead.

That becomes an obstacle to me, communicating with my audience by, by overhead. I mean, they’ve got historic legacy. Requirement’s that mean I can’t do anything right. You I’m on my iPad. I could just go in and send a message out. Or actually I haven’t sent a message out. Someone else has sent a message out.

Our publisher sent a message then from damn, ah, damn gravity. But I, but if someone says there’s a problem, I can go in and see it.

[00:26:44] Nathan:

[00:26:44] Andrew:
And make adjustments. The whole thing just fricking works. Right?

[00:26:47] Nathan:
So I want to talk about the book more. Let’s talk

[00:26:49] Andrew:

[00:26:50] Nathan:
And now I have you here.

[00:26:52] Andrew:
Ben needs, us to talk about the book. He’s the publisher.

[00:26:54] Nathan:
We’ll get to that, then don’t worry. Ben, we’ve got it covered. so you were giving unsolicited feedback, which by the way is my favorite kind of feedback. Okay.

So as you’ve been listening to the show, what are some other things that maybe you recommended the book, maybe like as you set people up for interview questions, any of that advice that you would give beyond?

We started with the men.

[00:27:15] Andrew:
I’m going to suggest that people who listen to you do pay attention to this. One thing that they should, I I’m interrupting you in a roadway now there’s some good interruption that I write about in the book and I can tell you how to do it. Right. And I also have to say that there’s some new Yorker that’s built in, even though I’ve left New York a long time ago, that I, I always interrupt when we need to get into the bottom line.

Okay. Here’s one thing that I think people should pay attention with you. You don’t just ask questions. You will, at times interject your own story, your own, take your own experience. And I find that a lot of times people either do it in a heavy handed way. It’s like, look at me, I’m equal to you. I deserve to be in this conversation too.

And that doesn’t just happen on Mike. It happens at dinner parties or it’s more like I have to be reverential. So I’m asking questions and it’s me asking about them. And one of the things that I learned over the years, Getting to know someone interviewing someone, whether it’s like you and I are doing in our podcasts and shows or doing it, in a, in a dinner conversation, it’s not asking questions.

It’s not about saying here’s my next thing. Here’s my next question. It’s overwhelming and draining to do that. You do need to say, well, here’s me. You do need to sometimes just guide the person to say, now tell me how you wrote the book. Now tell me how long it takes to, to write a tweet, right? Whatever it is, you need to sometimes direct the person.

And so I call the book, stop asking questions because that counter intuitive piece of knowledge is something that took me a fricking interview coach to help me accept that. It’s true, but it helps. And you do it really well. And here’s why you do it. Well, you interject something personal. Somehow you do it succinctly.

You don’t get rambling off. Maybe you edit that.

No, no, because the videos are there. Yeah. It’s, it’s not edited. It’s just you saying here’s, here’s my experience with this. And then when you come back and you ask something. It informs the guest about where you are and what they could contribute to that. It lets them also feel like this is a dialogue instead of them being pounded with demands of, in the forms of question.

[00:29:15] Nathan:
Yeah. Yeah. I think that for anyone listening and thinking about starting a podcast, it’s really like, what’s the kind of thing that you want to listen to. And I like it where the host is like a character in the, in the Podcast, in the episode where they’re contributing content and it’s not just like, oh, if I listened to Andrew on these 10 shows, I’m just going to get Andrew.

Like, I want it where it’s like, no, I’m getting the blend between these two people. And the unique things that come from that intersection rather than, you know, I’ve heard this

[00:29:46] Andrew:

[00:29:47] Nathan:
I’ve heard about it.

[00:29:48] Andrew:
I think also it took me a long time years of, so I started doing this in 2007, give or take a year and I think. No one needs to talk about, I don’t need to talk about myself. They don’t care about me. They care about, you know, Paul Graham, who I’m interviewing about how he found a Y Combinator, someone.

And I would get tons of emails from people saying, tell us who you are. Tell us a little bit about yourself. And I would argue with them and say, no, but I understand now on the outside, when I listen, I don’t know who you are. And it feels very awkward to hear it. It feels very much like, I don’t know why, where you’re coming from.

And so I don’t know why I should listen. It’s kinda, it’s it’s counterintuitive.

[00:30:29] Nathan:
Yeah. I think it just comes with comfort over time. Like, I, I don’t know this for sure. If I bet if I listen back to my first podcast episodes, the ones that I did in like 2015. I have a different style because I bet I’m less comfortable or more worried about like, make sure that I shut up quickly so that the guests can talk more because people came here for the guest and then over time you just get more comfortable.

[00:30:53] Andrew:
So you wrote authority and I remember you, I remember buying it and I remember you bundled it with a bunch of stuff, right. And oh, by the way, it’s so cool. I was listening to it on a run and I heard you mention my name in the, in the book I go, this is great and I’m running. but I remember you did interviews there.

I don’t remember whether the style matches up to today or what, but you did interviews in it. Right.

[00:31:15] Nathan:
I did.

[00:31:16] Andrew:
And what you had there that I think is always important to have with all, all interviews is you had a sense of like, well, the sense of mission, I knew what you were going for, because you were trying to say, here is this book that I’ve written on this topic.

I’m want to bring these people in to bring their, their take on it. We were all kind of working together. And I feel like, when I look at my earlier interviews, I listened to them. The Mike sucks so badly. I was too ponderous. Cause I wanted to be like, IRA glass from, from NPR, from this American life.

And you could hear the same rhythm, the same cadence, like I’m copying him. Like I’m his little brother trying to learn how to be like a real boy. but I had this real need. I was trying to figure out how these people were building companies that work to understand what holes I had in my understanding to see what was working for them that I didn’t know before.

And you could see that and it, it helps. It helped me continue. Even when I was nervous with the guest, it helped the guests know where to go. Even when I wasn’t doing good job, guiding them and help the audience keep listening in, even when the audio stopped, because there’s this thing that Andrew is trying to understand.

And you almost feel like you’re the sense of vulnerability. If it doesn’t scare you away, then it makes you want to root.

[00:32:40] Nathan:
Yeah. And I personally love that style because I want to follow someone going on a journey and, and trying to accomplish something specific. But let’s talk about the not just the book, but asking questions or in this case, stopping it, stop asking questions. What are the things that not even just specific to this job, what are the things that you listened to interview shows?

And you’re like, okay, here are the three things that I want to change or that I want to coach you on in the same way that I was coached on.

[00:33:10] Andrew:
Okay. So what I started to do is I go through my own transcripts. I mean, I had years of transcripts to see what worked and what didn’t I already done that. So I said, I need to now add to it. And so I went back and looked at historical interviews, like when Barbara Walters interviewed Richard Nixon and got him so frustrated that he didn’t want to ever talk to her again.

Or when Oprah finally got to sit with Lance Armstrong, how did she do that? I think. You know, you know, let me pause on, on Oprah and Lance Armstrong. She got to interview him after he, he was basically caught cheating and he was about to come out and do it. Great. Get, I think the fact that she interviewed him, there’s a lesson there for, for all of us who are interviewing, interviewing the top 10 interviews, I think of all time.

And you go back to Wikipedia and look it up. You see art or interview podcast or interview, sorry, our news-based interviews. We as podcasters, keep thinking, how do I get enough in the can so that if I die tomorrow, there’s enough interviews to last for a month or whatever, so that I can be consistent in the audience loved me.

That’s great. But I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who suddenly done something, we should go and ask to do an interview with them. If there’s a creator, if there’s someone. So for me, one of the top interviews that people still it’s been years, people still come back and talk to me about is when Matt Mullenweg decided that he was gonna pull out Chris

[00:34:35] Nathan:

[00:34:35] Andrew:
Per Pearson.

Pearson’s, themes from WordPress. And I got to talk to both of them at the same time and I published it and it went all over the internet with all over the WordPress internet. So hundreds of different blog posts about it, eventually all the people in the WordPress world write a lot of blogs, but also it became news.

And so we don’t do enough of that.

[00:34:57] Nathan:
I remember that interview because I was in the WordPress community at that time. And I remember you saying like, wait, I’m in Skype and I have both of you in two different things and you pull it together and not to pull Ryan holiday into this too much, but that’s where he ended up writing the book.

Was it, he realized he was one of the only people who was talking to like both Peter teal and, who’s the Gawker guy.

Yeah. Anyway, people know, but, but being in the intersection of that, so you’re saying find something that’s relevant on the news

[00:35:33] Andrew:
Yeah. Nick Denton was the founder of Gawker. Yes. Find the things that are relevant right now. And when people are hot right now, and they know you and you have credibility in this space, they trust you more than they trust. Say the wall street journal, even right, where they don’t know where’s this going.

I think that’s, that’s one thing. The other thing is I think we don’t have enough of a story within interviews. If we’re doing S if we’re doing at Mixergy, my podcast and interview where we’re telling someone’s story, we want them to be somewhere where the audience is at the beginning and then to have done something or had something happen to them that sets them on their own little journey.

And then we make this whole interview into this. Into this a hero’s journey approach. So I think better when I have an actual company in mind, so, or a person in mind. So last week I was interviewing this guy, Rohit Rowan was a person who was working at SanDisk, had everything going right for him. His boss comes to him and says it, you’re now a director, continue your work.

But now more responsibilities he’s elated. He goes back, home, comes back into the office. Things are good, does work. And then a couple of days later he’s told, you know, we mean temporarily, right? And he goes, what do you mean? I thought I got, I got a promotion. No, this is temporary. While our director’s out you’re director of this department.

And then you go back, he says, the very next day, he couldn’t go back into the office. He sat in his car, just, he couldn’t do it anymore. And so he decided at that point, he’d heard enough about entrepreneurship heard enough ideas. He had to go off on and do it himself. And so we did. And then through the successes and failures, we now have a story about someone who’s doing something that we can relate to, that we aspire to be more.

[00:37:13] Nathan:
So, how do you, you, your researchers, how do you find that moment before you have someone on? Because so many people will be like, yes, let me tell you about my business today. And oh, you want to know about that? How’d, you know, you know, like, as you,

[00:37:27] Andrew:

[00:37:28] Nathan:
That hook in that moment? That actually is a catalyst in their own dream.

[00:37:33] Andrew:

It’s tough. It’s it takes hours of talking to the guest of, of looking online of hunting for that moment. And it takes a lot of acceptance when it doesn’t happen. One of my interview coaches said, Andrew, be careful of not looking for the Batman moment. And I said, what do you mean? He goes, you’re always looking for the one moment that changed everything in people’s lives.

Like when Batman’s parents got shot. And from there, he went from being a regular boy to being a superhero. Who’s going to cry, fight crime everywhere. His life doesn’t really work that way. There aren’t these one moments, usually the change, everything. So I try not to. Put too much pressure on any one moment, but there are these little moments that indicate a bigger thing that happened to us.

And I look for those and I allow people to tell that without having it be the one and only thing that happened. So if Pharaoh, it, it wasn’t that moment. It could’ve just been, you know what, every day I go into the office and things are boring. And I think I have to stop. What I look for is give me an example of a boring.

Now he can tell me about a day, a day, where he’s sitting at his desk and all he’s doing is looking at his watch, looking at his watch and he has to take his watch, put it in his drawer so that he doesn’t get too distracted by looking at his watch all day. Cause he hates it. Now was that the one moment that changed everything?

It was one of many moments. It might’ve happened a year before he quit, but it’s an indication. So when we’re telling stories, we don’t have to shove too much pressure into one moment, but I do think it helps to find that one moment that encapsulates their, why, why did they go on this journey? Why does someone who’s in SanDisk decide he’s going to be an entrepreneur?

Why did someone who was a baseball player decide that he had to go and write a blog post? Why is it? What’s the thing that then sends them off on this journey? It helps. And I would even say, if you can get that moment, it just helps to get the thing that they were doing before that we can relate to. So what’s the thing that they did before.

So anyway, we have two different types of interviews. One is the story-based interview where we tell a story of how someone achieved something great. And so that hero’s journey is and approach. The other one is someone just wants to teach them. All you want to do is just pound into them for an hour. Give me another tip another tip another tip of how to do this.

Like pound, pound, pound, pound pound. If you want the audience to listen. I think for there, it helps to have what I call the cult hook because I said, how do I, how do cults get people to listen to, to these people who are clearly whack jobs sometimes. And so studying one called I saw that what they did was they’d have a person up on stage who talked about how, you know, I used to really be a Boozer.

If you came into my house, you would see that there’d be these empty six packs. I was so proud of leaving the empty six packs everywhere to show myself how much alcohol I can drink. My wife left me. And when she left me, she just told me that I hadn’t amounted to anything in my life. And I was going nowhere.

And I just said, get I here. Instead of appreciating that this was just like terrible. And I ran out of toilet paper and don’t even get me started with what, what I did for that. And so you see someone who’s worry worse off than you are on this path of life. And then something has. They discover whoever it is.

That’s the cult leader. And they say, now I’ve got this real estate firm I encouraged by, oh, by the way, all of you to come over and take a look at that at this, I couldn’t believe it. My whole life. I wanted to buy a Tesla. I now have the Tesla S it’s amazing. It’s just so great. And I did it all because I changed the way I thought once I came in and I found this one book and the book told me, I mean, anyways, so what we try to do is we say, if you’re going to have somebody come on to teach how they became a better blogger, let’s not have them start over elevated where everything they do is so great that we can’t relate, have them start off either relatable or worse.

I couldn’t write here’s my grammar, mistakes. My teacher told. Right. And now what’s the thing that they did. They pick them from where they were to where they are today. it’s this real set of realizations. Now I want to go into that.

Let’s pound into them and see how many of those tips we can get. Let’s learn that I want to go from where he was to where he is.

[00:41:28] Nathan:
Yeah, I liked that a lot. Cause my inclination would be like, okay, we’re we’re doing the, educational, tactical conversation. I’m going to facilitate it. Let’s dive right in and let’s get to the actionable stuff right away. So I like what you’re saying of like, no, no, no. We need to, even though this is going to be 90% packed, full of actionable material, we need to dive in and set the stage first with the story and making it relatable.

And I like it.

[00:41:55] Andrew:

[00:41:55] Nathan:
Oh, yeah. I was just, just in my own head for a second. Cause I say, ah, that makes sense a lot, so much so that I’ve had three different guests or listeners email me and say like, just don’t say that makes sense as much would, now that I’m saying it on the show, I’ll probably get more emails every time that I say it.

Cause that’s like my processing, like, oh, oh, that makes sense. As I’m thinking of the next question and all that, so

[00:42:22] Andrew:
I do something like that too. For me. It’s IC,

[00:42:25] Nathan:
Everyone has to have something.

[00:42:26] Andrew:
I can’t get rid of that and yeah.

[00:42:28] Nathan:
So what systems have you put in place on the research side so that you’re getting this, are you doing pre-interviews forever? Yes. Are you having your

[00:42:38] Andrew:
Almost every single one, some of the best people in some of the best entrepreneurs on the planet, I’m surprised that they will spend an hour or do a pre-interview. And sometimes I’m too sheepish to say, I need an hour of your time and I need you to do a pre-interview. So instead of saying, I need you to do a pre-interview.

I say, here’s why people have done it. And I’ve paid for somebody to help make my guests better storytellers of their own stories. And truthfully people will go through that. Pre-interview even if they don’t want to do an interview, they just need to get better at telling their story for their teams, their employees, their everyone.

Right. and so I say that, and then they will take me up on the pre-interview and say, yes, I do want to do the pre-interview. and so what I try to do is I try to outline the story. Ahead of time in a set of questions. And then what we do is we scramble them up a little bit based on what we think people will tell us first and what will make them feel a little more comfortable.

And then throughout the interview, I’ll adjust it. So for example, no, one’s going to care about the guest unless they have a challenge. No guest wants to come on and say, I’m going to tell you about what’s what I really suck at or where I’ve really been challenged. If they do, they’re going to give you a fake made up thing that they’ve told a million times to make themselves seem humble.

So we don’t ask that in the beginning. We don’t even ask it in the middle. We save it till the very end. Now they’ve gotten some time with us. They’ve gotten some rapport, they trust us. Then we go into tell me about the challenges, what hasn’t worked out for you. And we really let them know why tell people the higher purpose you want the audience to relate.

You want them to believe you. You want them to see themselves in you, and to learn from you. We need. They tell us, and then I have it in my notes as the last section, but I use it throughout the interview. I sprinkle it. So the goal is to get the pieces that we want and in whatever order makes the most sense and then reshape it for the interview Day.

[00:44:33] Nathan:
So on the interview itself, you would, you would flip that and you know, okay, this is what I want to start with and, and dive in right

[00:44:41] Andrew:
Yup. Yup.

[00:44:43] Nathan:
Lose. They already told you about that. And so now, you

[00:44:46] Andrew:

[00:44:46] Nathan:
In and start with.

[00:44:47] Andrew:
Right. That helps. Now, if there’s something I want to ask someone about that they’re not comfortable with. One thing that I do is I, I tip them off. So Jason Calacanis invited me to go do, interviews with, with investors at one of his conferences. It was just a bunch of, investors. And I looked at this one guy, Jonathan tryst, and he looked really great.

But he, what am I supposed to do? Ask him about what startups should do to run their businesses. He’s never run a startup. His, he hadn’t at that time had a successful exit. As far as I knew, like mega successful exit. He’s just a really nice guy. You can tell he was going places, but that’s it. And the money that he was investing came from his parents.

So what is this rich parents giving their kids some money. Now he’s going to tell everyone in the VC, in the startup and VC audience, how to live their lives. So I said, I’m either not going to address it, which I think most people are, or I have to find a way to address it where I’m not going to piss them off and have them just clam up on me and then go to Jason and go.

This guy just is a terrible interviewer, which is not true. So what I decided to do was tip him off. I said, look, Jonathan, before we do this, before we start talking to the audience, I have to tell you, I saw it, that you don’t have much of a track record as an investor. Your money came from your parents and you’re not like a tech startup, like people here.

If we don’t talk about it, people who know it are going to think, oh, this guy, Jonathan, look, who’s trying to pass him soft self off. I don’t have to force it in here, but if you allow me to, I’d like to bring it up and let’s talk about, and it goes, yeah, absolutely. If it’s out there, I want to make sure that we address it and sure enough, we talked about it and he had a great answer.

He said, no, this came from my parents. It’s not my own money. I don’t have as much experience as other people, but I took my parents’ money. I invested it, fat parents and family and so on. We’ve had a good track record with it. And now have raised the second Fallon fund from outsiders who saw what I was able to do with the first one.

And by the way, I may not have this mega exit as a startup investor, as a startup entrepreneur. But I did have this company that did okay. Not great. Here’s what it did Here’s what I learned And that’s all informing me. And that’s where I come from now. You’ve got someone talking about the, the, the thing that matters without pissing them off so much that they don’t say anything else.

And you feel like you feel superior as an interviewer. I got them. But in reality, you got nothing

[00:46:57] Nathan:

[00:46:57] Andrew:

[00:46:58] Nathan:
I think that’s a really hard line of talking about the things that are difficult and like the actual, maybe things that someone did wrong or lessons that they learned without just like barely dipping into it for a second. And I liked the format of tipping them off in like full transparency.

So on this show, I had someone on who I really, really respect his name’s Dickie Bush. He’s one of the earlier episodes in this series and in it, he, okay. Yeah. So in that interview, one thing that I knew is that his, the first version of his course plagiarized text from another friend, Sean McCabe, actually Shaun’s company edits is Podcast and all that.

And I’ve known both of them for, for quite a while. I’ve known Sean for like, I dunno, six, seven years or something. And I was like, struggling with how to bring that up. And I wanted from the like founder, transparent journey, that sort of thing I wanted it brought up because I, I actually like, I’m happy to talk about like some pretty major things that I’ve screwed up and what I’ve learned from it.

And I just think it makes a better conversation. And then from the interview side, I don’t feel good, like doing an interview and not touching on that, but I didn’t tip Dickey off to it. And I, that was one of the things that I’ve regretted that he gave a great answer. He talked about the lessons that he learned from it.

It was really, really good, but I felt bad that I didn’t set him up for the most success in like in setting up. And part of that, part of it is because even at the start of the interview, I was still wrestling with now, I’m not going to bring that up that, ah, maybe I should, it wouldn’t be an authentic interview if I didn’t like wrestling with that, I hadn’t figured out my own, like made my own decision until we were in the middle of it.

And so I didn’t, I didn’t set anybody up for success. And so it’s an interesting line.

[00:48:52] Andrew:
It happens. And it seems like I’m now in the point of your transcript, where you, where you ask him, it’s a 31 minutes into the interview. I think his response is great. He came in and he took responsibility for it. He says, yeah, that, that, that was a dramatic mistake, or a drastic mistake on my side and caught up in it.

He wasn’t the most articulate here and he’d repeated words. Like I, I, a couple of times, so I could see that he probably was uncomfortable with it. but I think his answer was great. I think, I believe that we all are broadcasting out, whether we know it or not, our intentions and where we’re coming from, as some people are really good at faking it.

And so I’m not going to talk about the outliers and some people are so uncomfortable that they’re messing up the transmission, but for the most part almost. broadcasting our intentions. If you walk into that, Nathan, with the, I got to get him because he, he got one of my friends and I need him to finally get his comeuppance.

He’s going to pick up on that. And truthfully, it’s such a small thing for a person like you who’s, who’s already a likable person. You have a lot to offer people, right? As far as like promotion and everything else, it will be forgiven, but it’ll be picked up on, it’s also something that people could pick up on, which is Nathan really want to know this thing.

It’s been bothering him for a while. And if you could, just, before you asked the question, say, where am I coming from with this? And know that the audience will mostly pick up on it. And obviously people are gonna like read in whatever they feel like, but trust that the vast majority of us understand, I think it’ll work

[00:50:21] Nathan:

[00:50:22] Andrew:
You don’t have to even tip. You don’t have to tip off, but it does help. It, it definitely helps.

[00:50:26] Nathan:
It’s interesting. I was watching an interview with, Jordan Peterson who wrote 12 rules for life. He’s like a very controversial figure. And I was just often these controversies pass by, on Twitter and other places. And I realized like, oh, I don’t understand them. And rather than jumping on one side or the other, at least try to like dive in a little bit and understand it.

So watching this interview, and I can’t remember, I think it was some major Canadian TV show or something, and that you would tell the interview was just trying to nail him it every possible chance, like whatever he said, just like dive in. And, so I think you’re right, that you see the intention, like in that case, you would see the, the interview, his intention was specifically to try to trip him up in his words.

And then in other cases where it’s like, This is something that, you know, if you take the other approach, this is something that’s been bothering me, or I want to talk about it. Like I genuinely want, you know, to ask or learn from this. It’s a very different thing.

[00:51:20] Andrew:
I think people pick up on it. I remember you, you mentioned Seth Godin. I remember interviewing him when he wrote the book tribes back before people had online communities. And I didn’t just say, okay. All our heroes, all the best entrepreneurs just run their businesses. Then don’t run a tribe. I brought out books.

I said, here’s a book about Warren buffet. Here’s the book by Sam Walton. The Walmart here’s a book by Ted Turner became a multi-billionaire to creating all these, these media empires didn’t have communities. They don’t have tribes. And now you’re telling me that in addition to my job, I also have to go and build out a tribe.

It feels like, you know, an extra job. That just seems right for the social first. This just sounds right on social media and you could actually see. He’s watching me as I’m saying it, and he’s smiling, he’s watching it because he’s trying to read me, is this like what I get wrapped up? Is this going to be some kind of thing where some guy’s going to try to be in the next Gawker media?

Or is, is this a safe place? We’re all doing that constantly. And then he also saw, okay, this is someone who really wants to understand this. And he’s challenging me. I like a challenge. And you could see him smile with like, this is what I’m here for. And so I think when you come at it from a good point of view, people can see it and then you can go there and you can go there and you can go there and it will be shocking to you and them and the audience, how far you go. But when you’re coming from that genuine place, they get, they get it.

They want it.

[00:52:44] Nathan:
Yeah, that’s good.

I want to talk about longevity in like the online world. I think that so many people that I started following in say 2007, 2008, nine, and then I didn’t start creating myself until 2011. most of them aren’t around anymore. Like a lot of the big blogs, Yeah, just so many that I can think of.

They’re not around anymore. They’re not doing this. You’re at a point where like you started messaging in some form in what? 20, sorry, 2004 to somewhere in there and then interviews.

[00:53:17] Andrew:
Yeah, I keep saying 16. It’s like, yeah. 2004 is when I started the interview started 2007 ish somewhere there. Give or take a year. yeah, long. I, I will say that there are parts of my work that I am burned out on right now. This year has been that, but I’m not on the interview. And the reason I’m not is because I do enjoy conversations.

I hated them for a long time in my life because I just didn’t know how to have them, how to have it make sense. I also didn’t give myself permission to take the conversation where I wanted it to go. And it helps now to say, I can talk to anyone about anything. That’s an opportunity that, that feels fun because I know how to do it.

It’s an opportunity to, it feels like, like, you know how everyone’s so happy. You can go to YouTube and you could get the answer to anything. Well, I could go to anybody and I could get the answer to anything and talk about how they didn’t have a customized to me, YouTube, not customized thing to me, I’m watching Gotham chess on YouTube.

He’s teaching me how to play chess, but he will not customize to the fact that every time I get into a car con defense, all the pieces like bunched over to my side. But if he and I did an interview, or if I do an interview with an tomorrow’s entrepreneur, it’s going to be about, here’s the thing I’m trying to deal with.

How did you get past that? Talk to me about what you’re up to there.

[00:54:31] Nathan:
Yeah, that’s definitely energizing. Okay. But what are the things that you’re burnt out on? Because I think a lot of people are seeing that burnout. And so I guess first, what are you burned out on? And then second, we can go from there into like, what are you changing and how are you managing.

[00:54:46] Andrew:
I’m burned out on parts of the business behind, behind Mixergy I’m burned out on. I was aspiring to like unbelievable greatness with the, with the course part of it, with the courses, it didn’t get there and I’m tired of trying to make it into this thing. That’s going to be super big. I’m tired of that.

[00:55:10] Nathan:
His greatness there, like Like what, what was that?

[00:55:15] Andrew:
Yeah, yeah, yeah. Yes. Yeah. She was one of my first interviewees and, and so yeah, I saw the model there and I am frustrated that I didn’t get to that and I, I don’t have a beat myself up type a personality, despite some of the questions that I ask. Maybe it seems that way. I’m pretty good with it, but, but I’m tired of being, trying to get it there and not getting it they’re trying and not, and trying another way.

And so to answer your question of what am I doing, I’m going to give myself space to not, to not try to do that, to not try to, to go for greatness for a little bit, and instead give myself room to do the interviews that I care about and play more chess and then experiment with random things that I don’t know what will come up, you know?

I don’t know. At one point I, I think I, so I get together with some friends for monthly calls and, and one of the calls I said, I’m looking at land and what if I get some land near San Francisco, right? It’s super cheap in San Francisco. You can buy a tiny house for two, 200, excuse me, for $2 million. But if I just go 45 minutes down south a little bit further down than Silicon valley. For $400,000, I get acres. And then I could put some tents on there. Maybe get an Airstream, let people stay on it and see what that goes. Anyway. That’s such a random thing that I think that they were a little worried about me, but I’m even open to random ideas like that. And then who knows, maybe come back after a year of taking that space.

[00:56:53] Nathan:
Yeah, that makes sense to me, of, of taking space and time, you know, like first you know, years ago it was the great recession. Now everyone’s talking about the great resignation where like the, I don’t know the exact statistics, but a crazy number of people across the industry, but especially like knowledge workers and people in tech are either switching jobs or just like putting their notice and like saying, I don’t know what I’m going to do next.

But like, I, I, I’m fully confident that when I’m ready to come back, there will be a job, you know, some kind of Write of like, I’ll find another programming job. That’ll be fine. And so I think it’s a good thing to talk about because so many people are feeling. And most people just leave it at, like I’m burned out, so whatever.

Right. You know, so I pushed through or I’m burned out. So I left, you know, and so actually talking about those things that that either drove the burnout or, you know, specific things that you’re doing about it.

[00:57:52] Andrew:
So are you asking me what drove my book? Me to my burnout.

[00:57:56] Nathan:
Yeah. I’m, I’m curious for more of that.

[00:57:58] Andrew:
Sure. I think I have this all or nothing. Personality I’m all in or nothing. So, it, it’s not like I’m going to do a nice two mile run. I have to do a marathon and then I have to do another and another and another,

[00:58:17] Nathan:
In a year.

[00:58:18] Andrew:
Right. Yeah, exactly. And that fits me. I want to be the person who I love scotch. I’ve been in Austin for a little bit and they don’t sell them everywhere.

You have to go to special liquor stores. I haven’t had any here. Right. So I’m down to zero. That’s also, excuse me, fine. But if I’m drinking scotch with people, I’ll finish a third of the bottle, half the bottle, no problem. And then I’ll wake up the next morning and be the person who is so proud that he’s like Up before everyone else and running into work.

I think that that type of thing suits me, but I think that the downside of that is that then I do just burn out and I can say that that’s happened now twice before. So I think that that’s what’s happening now. The first was in college. I took college really seriously because I thought this is going to show you.

I thought it was gonna shape my future. it really didn’t, but I wanted to really do well in all those classes. Especially since I finally got business classes after years of wishing I could study business or something practical, but instead being given things that like the Pythagorean theorem, that didn’t matter, I had it.

So I took it seriously. But I remember at the end I graduated, burned out where I remember my boss offered me a job and I said, I really just can’t think, I think what the offer you’re making me make sense. I just don’t know. And I took time off. I drove my parents crazy is I finished school and didn’t want to work anywhere.

And then again, after my greeting card company, I worked on that endlessly. I would take a keyboard with my phone into bed so that I can type out long emails in response to people. and then I burned out and decided I would just go ride my bike on the Pacific coast highway for a year, whatever for years.

[00:59:56] Nathan:
Is there anything that you’re taking into this period of, of like space. That you’ve learned from the, from the past months or your added level of intentionality,

[01:00:07] Andrew:
No, I don’t, I’m not there yet. I’m really excited about this book. And so I’m talking about it. I’m really excited about the process of interviewing. I feel like I underestimated the importance of it until I wrote this book. So COVID just had me locked up inside for a bit. And I said, all right, I’m how do I use this?

And I ended up writing the book and then as I examined it, I realized I really do love the craft of conversations, the, the, the structure of them, of how we end up with, how, how do I end up in a great conversation with people? My kids this morning, one of them is seven. The other’s five to seven year old, said we are not shy on like other kids.

We go in with adults and we have conversations with them all the time, because you always get us in, you talk to everybody. And I thought, what a gift that they could we’re in Austin, that they could go to somebody’s house and feel as comfortable in their houses as any one of their friends does, even though.

You know, the first time that they’re, that they’re in the house and they don’t even know if there’s anything for kids to do. I love that. And that doesn’t just come from happenstance or gift from God. It just is spend time. I spend time thinking about it And working on it And I’m proud of it. So I’m continuing to do that.

And then who knows what will come after burnout, maybe after burnout will just be sitting on the couch with all day. Just try to master that CARICOM defense.

[01:01:21] Nathan:
Yeah, that’s a good, good use of time. I think I say that genuinely. I, I am not on,

[01:01:30] Andrew:

[01:01:31] Nathan:
Of, of chess, but I thoroughly enjoy it. And I, you know, I play chess against a ten-year-old and a seven year old for the most part. And getting to the point where they can.

[01:01:38] Andrew:
The good actually seriously, if you take a look younger kids for some reason, if they’re good, they’re amazing. They’ve got to, I don’t even know how they can

[01:01:46] Nathan:
Yeah. And, but it’s, it’s also amazing to see. I mean, my kids aren’t, aren’t phenomenal by any means. I can still beat them, but they’re like, you see the, the rate of improvement over time, especially if you explain, like, don’t do this, where do I see why this is a bad idea? Like they will not make that mistake again, you know? at least in chess, I haven’t figured out the parenting side of that.

If you have, let me know.

I’m curious on the, on the other side, like going to the interviews, is there anyone that you have on your list that you’re like, oh, I really want to interview this person, or maybe this person tied to this a point in time as well,

[01:02:24] Andrew:
You know what it is? It’s sometimes something will make it into, into the news. Someone will have done something amazing. We’ll all start talking about them and I’ll want that person. And one of the gifts of this, of this experience of having been out there for so long as I could, I could say, there’s, there’s this person, who’s this, this guy, Andrew, I can’t remember his name.

White. He just talked about. This is so small. You’re probably thinking about who’s it like a major mark Cuban. I’m not interested in mark Cuban. I’ve heard everything has to say here’s my excite, my excitement, this dude, Andrew he’s finally revealed how much money he made from. I think it was, he must have hit a million dollars.

My memory is not great on this, but here’s what I do. He wanted to have his own software company. He had a wife and kid, he couldn’t find a way to squeeze it in. He knew he needed to learn to program. He decided that on the way into work on the train, he would sit there with a laptop. You ever see people on the train with the laptop?

I feel so sad for them, right? This is no way to work. It’s not comfortable. And plus I feel like I, cause that maybe it’s because I had lived in New York and San Francisco, I feel like someone’s going to snatch it out of their hands, poor souls. And they’re going to lose the laptop too. But he’s one of those poor souls sitting there working.

And he ends up creating this company that does charts because he realizes for developers hard to make nice looking charts. And so he says, I’ll create a way. Developers can just plug into my stuff and they’ll have nice looking charts. And suddenly people who are racing cars who need charts to see how the cars are doing and different parts of the cars are performing midway through the race.

They’re using his charts to show that like it’s making great money and his life has changed. And I did that guy a lot and I love that. I have the freedom to say, people are talking about him right now. I am curious about him right now. I’m going to go and ask him right now. Can we do this interview? That’s helpful. And then one more thing I think for doing interviews and you’re, you’ve seen this in your own life in different ways. There’s also like a follow-up effect where the people who you’ve done interviews with you may never see them again. But some you have access to for the rest of both of your lives.

I mean, literally for the rest of both of your lives. So one, one example is I started writing the book. I couldn’t keep on writing it. I’m sitting down here at my iPad, typing away. I couldn’t do it. I can’t, I can’t believe how many words a day I keep in my head. Someone asked you on Twitter while I was writing this.

Do you still do a whatever number of words a day? And you gave the number of word I want to punch my screen. I go, how the hell is this guy doing it? I can’t do it. Hey, I said, I’m going to hire a ghost writer. And I started emailing Ryan holiday to go. This is terrible. I’m literally giving up other, every other part of my work in life, except for like, after, with my kids, after they’re done with school, I’m done except for writing this book.

How do I continue this? How do I hire a ghost writer? And his response was the most in sympathetic response ever, but it was great because that’s what got me to like stop looking to hire a ghost writer. And I’m the type of person who I would just hire someone, give them a direction and be done. And so don’t think if I were just a random dude, messaging people all day, that they would respond like that.

I don’t think I was a random dude, not knowing how to master the Cara con that James Altucher was a phenomenal chess, chess player, right. And a great writer I’m reaching out. He goes, let’s get on a Skype call or zoom call. We get on a zoom call. We only met during the interview. The dude is so good. He’s analyzing my game.

He’s giving me homework assignments. I did one of his homework assignments this morning, and suddenly my game has improved because of it. There’s this extra benefit, and it reminds me of something that Ali Abdaal said in your interview. He said, if you stick with this (and for him, it was YouTube), if you stick with this for month after month after month, I guarantee you it’ll change your life.

I’m not going to make promises on what you’ll have financially, but I guarantee you it’ll change your life. I wish he would have said change your life for the better, because I’m a little worried about the people sitting there creating YouTube videos, and their lives getting destroyed from all the hours.

But, I think if you sit there and you do interviews, guaranteed it changes your life for the better.

[01:06:17] Nathan:
Yeah. I mean that consistent way of showing up makes a huge difference, and access to people is incredible, and the relationships, and everything else.

[01:06:25] Andrew:

[01:06:26] Nathan:
Where should people go to check out the book?

[01:06:28] Andrew:
I got this great landing page from a company called ConvertKit. Alright, here’s all they have to do:

[01:06:33] Nathan:
I love it.

[01:06:34] Andrew:
All they have to do is go to:, and here’s all I have to do. If I have to send out a message, I don’t have to figure out crazy charts, and all these systems and rules.

I just log in—I could do it on an iPad—and then I send out my message. What I’ve been doing, Nathan, is when I hear that people have a problem with conversation, I find a chapter from the book and I email it out. Then I say, what do you think? Is this working?

I send that out to the whole list, and it’s so helpful to have people email me back, asking for direction or saying how they’ve used it. One person had this terrible story about some bad thing that I did with the founder of Zero, the accounting software.

I was hoping that people wouldn’t ridicule me for that, or judge me negatively for it. Nobody did. So, that made me feel good, and I left it in the book. But someone did say you actually misspelled his name. So, I went back and changed it in the book. Not just that, but the publisher made sure every single one of these names was double-checked.

So, it helps. Thank you.

[01:07:31] Nathan:
An audience is so helpful for that.

Well, everyone should go sign up for the book. When does it come out?

[01:07:36] Andrew:, mid-October.

[01:07:40] Nathan:

Okay, cool. Right about the same time that this episode will drop. So, it’ll be perfect. Alright, Andrew. Thanks so much for coming on.

[01:07:47] Andrew:
Thanks Nathan.

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