Andrew: Hey there, freedom fighters. I’ve got a different kind of interview here today. Um, I don’t think that I’ve told you yet, but I’ve got a book that’s coming out. It’s called stop asking questions. It’s full of techniques that I have learned for having better conversations. And, um, well, I haven’t told you enough.
But my new friend, Tom Boyd here from the podcast creators, our brands invited me on his podcast to talk about the book, talk about the ideas, talk about my interviewing style. And if you want to get a sense of why the interviews that you’ve been listening to in this podcast feed are the way that they are, why the conversations.
Are the way that they are and how I get people to go open. Well, you’re going to get a taste of it here with my, uh, interview with Tom Boyd. Again, he’s interviewing me for his podcast. I really liked it a lot. And I asked him if I could put it in my feed, he said, yes. And so here it is. And if you want more of Tom, go look for creators.
Are brands in your podcast app or creators? Our brands.com on the web. All right. Here’s the interview that he did with me.
Tom: So I want to, I want to start with a quick story and it, we, we were discussing your, your, your book that is coming out, uh, inside old stop asking questions. And didn’t, I wasn’t gonna bring this up and a light bulb popped off So I’m going to reveal to you. The reason I enjoy asking questions so much is because of my mother.
And when you were talking about the title of your book before we started recording, I own, I honestly almost teared up because I was, I was like, I really get this from my mom. And there’s this quote. That says about my mom. And he says we could be at the movie theater and mom goes into the bathroom. And by the time she comes out, she meets someone in the bathroom.
And by the time she comes out, she knows the woman’s mortgage. And she just has this ability to connect with people, genuinely curiously, almost selfishly, you know, kind of like, I’m just, Hey, what’s going on in your world? And you mentioned this in an. In another interview at some point.
And I, and I love it so much cause it made me feel better for how I conduct my interviews. You said the best interview seemed to be the most selfish interviews
Tom: that made me feel good. Cause I was like, I, you know, that’s why I started this. This gives me an excuse to talk to people I’m truly interested in
Andrew: You know what you’re absolutely right, Tom, I’m sorry to interrupt you. I’m being
Tom: no, no, go ahead. I was, I was a long
Andrew: no, no. You’re absolutely right. Here’s the thing I get interviewed because I’ve been doing these interviews now, on my podcast for the last 14 years, over 2000 interviews, people often ask me to be interviewed to interview me.
So I sit down. And they go through all the things they think they have to ask about my business, which they read like 50 billion times, but they don’t care about the reason they know me. And they want to interview me is because they read it 50 billion times. They asked me about this, the, the, um, the company that I started about where I went to school, all that.
And then at the end they say, By the way, how do you get anyone to listen to a podcast? And that’s really what they wanted. What they came to this with was this selfish need to say, I’ve got this podcast, nobody’s listening, I’m suffering through creating it. What do I do? I should ask Andrew. Andrew has been doing this.
He’s got an audience. I’ll ask him. But I can’t just ask him. So I’ll ask him to do an interview. I can’t just ask them in the interview because then it looked like I tricked them into giving me advice. And so we sit and we go through the stuff that they think they should. And you know what? This happens a lot.
It happens at dinner parties. It happens. Um, when you’re talking to a new person, it happens at work conversations, all this stuff we’re supposed to ask. It bores us both to death. When there’s stuff we really want to know. And go to the selfish and be okay with it. And I’m not saying ignore the other person.
I’m just saying, what is it that you care about? It’s fine to ask. That’s what we’re here for.
Tom: I think this is the strongest intro to any of any one of my podcasts. And I have to admit sitting here talking to you, it feels like, like this is the lens I’m looking at. It. I’m a newbie. I I’m
Andrew: You’ve been doing like 150 podcast episodes. And beyond that even more. All right. I’m now shouting you down. What do you mean by a newbie? Let me take a step
Tom: uh, newbie. You’ve you’ve interviewed over 2000 people. You have a lot of experience asking questions. So I would like the, the true you asked me what would make it a win for me at the end of this conversation? 35 minutes in whenever I want you to give me blunt feedback on.
Tom: how I’m asking questions and how I can improve, because I feel like that will selfishly help me.
And then a listener who knows the podcast knows my style and they might hear it at the end and be like, oh, he’s right. He’s right. Tom needs to stop doing that. Tom needs to start doing more of that. Does that sound
Andrew: Yeah, absolutely.
Tom: Okay. Well, and so let’s get right into it. Cause that’s, that’s the lens that I want to talk through.
I think people can get the insight to your company. Everything you’ve done on your website. Everything’s out there. I want to, I want to get better at asking questions, but the title of your book is called stop asking questions. Can, can we understand that a little more?
Andrew: Yes. If we just keep asking questions, we’re going to sound like four year olds who want to know everything and want to be told everything. And if it comes across as obnoxious, what we need to do when we’re curious about people is. Pay attention to how we’re asking and make sure that we’re not coming across as overly needy people.
And where did you come up with your idea? What do you think I should be doing differently? How do you think I could do it in better? How did you get started? What are you doing that works? Right? Notice how you, uh, you told me, you said when this is over, I want you to tell me what I could do better. You didn’t ask it as afraid you didn’t ask it as a question.
You phrased it as a statement. And the thing that I realized after doing interviews is. A lot of conversation, stuff is intuitive and wrong and it’s enough to get by and you’re not going to feel the errors, but if you’re doing it a lot, you’re going to start to really have problems. And you’re not going to know why, because everything you’re doing seems right.
You’re asking questions. That’s why people came to do an interview with you. Why do they feel so bothered after an hour? Well, it’s little things like you hit them with question after question after question, they feel tired and sometimes what you need to do is. Stop asking questions and rephrase things.
Even as a sentence, even if you, instead of saying, where’d you come up with, uh, your business idea, say, tell me how you came up with your business. Tell me why you sold the company. You’re guiding people now that’s one layer, just simple rephrasing. It makes it sound less like your needy person asking for help.
And more like you’re going to guide this because you’re the producer of this conversation and you’re going to help them do a good job here in front of an audience that they don’t know. And they have every reason to feel insecure about. So that’s one way, another way. You can pause from time to time and acknowledge what they’ve said and say, you know what, here’s an experience that I had in my life.
So that there’s a little bit of reciprocation enough that it feels like it’s a real conversation that you’re sharing with them. And that you’re not just squeezing them for info and you’re not needy like a four year old or an intern in their lives. And that’s what I mean. And the reason I titled the book stop asking questions is because a lot of good conversation advice is good at the surface.
When you want to go do. It hurts you and you need to go counterintuitive and to really analyze it.
Tom: Yeah. And I, I find too, at least when I was just starting out, that when I was too regimented on the questions that I was trying to hit, I would leave a lot of the good stuff on the table where the conversation was naturally going. So I listened to the podcast back and I’m like, oh, I just totally skipped the natural progression of that conversation because I had this list of questions I needed to hit.
Andrew: know what, let me say this. One of my friends is a guy named Johnny Chan. He works at. Uh, people.ai, helping train their salespeople, they’re professional salespeople, selling software to professional salespeople. Right? One of the things that I saw him get excited about when he looked at new technology was tech tech that takes zoom calls and analyzes it.
And help salespeople. See, what did they say that helped close the sale? What did they say that kept people from closing the sales? What I noticed from watching really good salespeople, I came in trainers I came is they don’t count on charisma to tell them whether someone’s doing well. They do what you did.
You go back and you listen, they will leave. Get transcripts of what they said so that there’s no emotional connection to the words. And you could see it in black and white there. The customer said that they’re excited and me, I shut the conversation down and switch there. I asked the question and boom, they open up or more like, it’s opened up.
Why is this going on for paragraph paragraph? Oh yeah. I asked this one thing. I said, this one thing and it triggered it. And so what I’d suggest to you. Uh, frankly, anyone who’s in conversations at all, whether you’re working with clients, whether you’re working as an interviewer, the way you and I are right now, whether it’s just sales, anything, record those conversations and they never been better tools.
Zoom has one button you press, and you record. If you’re in a conversation with the client, say I’m going to record this so that we both have a record of what we have, what we said, and we can go back and look at our notes. Don’t just go back and look at your notes for the task and the to-do and all that go back and say, where did the COVID.
Get exciting or to get productive. What do they feel like the clothes where they feel like they didn’t and then what did I say before to led to it? That little bit of analysis is what led me to see what my best techniques were in conversation and then save them so I could reuse them and not hope that I have a great conversation, but actually create a better, uh, a great conversation.
So I love that you’re doing it. I’m just suggesting transcripts to.
Tom: Yeah. And how much of your conversations are kind of planned out in advance versus after you recorded an interview? Let’s say you had 35 points to.
touch and then after the interview, how many of those points would you say a percentage wise? Would you actually hit on?
Andrew: It’s hard to say, I got to
Tom: that’s like a very granular
Andrew: No. I know, I know what you’re getting at Tom. I got this place where everything was finally running right in a company. Right. If I’m going to record thousands of interviews, I need to have a team that does research, that books that follows through that spends time.
Pre-interviewing a guest. And I remember I was in, was one interview and I wish I could remember the name of the person, because I remember looking at my notes and saying to him, because I always am open to the. What we’re saying is so good, but I feel bad. You spent an hour with my producer and the pre-interview.
I want to keep going on this train of thought that we have, instead of going on what we said in the pre-interview notes. And he gave me permission. He said, I am the audience, not just the audience in you, but I also want the best possible conversation. If we’re seeing that we’re riffing here in a way that’s going better than anything we planned, I would much rather sacrifice the hour of work that I did before in the pre-interview and the notes and what we discussed that we’re going to talk about.
I’d much rather sacrifice all that and go for the great, and so that gave me permission in general, to say, I might have this list of 47 points that I want to get into a conversation, but if this is a good vein, if we’re going down a good path, I have to be willing to burn all that work that my team and I did and feel good about it.
And that’s, that’s the heart of good conversations being willing to burn the good for the great.
Tom: Yup. And it it’s really neat that you’re at a point in your career that you’re able to, you have a team, you have a S a system around you to. To look at these interviews from all angles. My question is for the person that might have a full-time job, it doesn’t have much to do research on people, uh, as much as they would like, but they’re, they’re really curious, like they want to do this.
They just want to get started. Let’s say this person is a couple of interviews in, and he gets this opportunity last minute to interview one of his favorite authors, but he only has. To prepare for this interview, where should he spend his time in that hour to prepare for that interview?
Andrew: Alright. First of all, the reason that I have a team it’s actually AIG Vaynerchuck’s fault, or I credit him and I fought my fault. I credit him. I was doing an interview with AJ Vaynerchuk, Gary Vaynerchuks brother. And I’d known him a little bit over the years. Yeah. And so I was as open as I always am in my interviews.
And I said, I’m, I’m burning out here. I’m doing too much. What do I do? And he said, Andrew, you could hire someone to help. I said, I can’t, there’s not enough of an operation here. And he said, you know, people who are listening would volunteer to do this, to help you out because they want to get to know the people that you’re interviewing.
They want to get to know you. They want to see the operation from the inside. Do you know how helpful that is? Just ask for a volunteer. I don’t think I had the guts to ask for a volunteer. He then asked for a volunteer on my behalf and started me off with a team of people. The first ones were volunteers who just wanted to see how is this done because they want to do it themselves.
Who wanted to actually get to know the guests, want to learn from me what I was doing so that they could do it too. So anyone who doesn’t have a team I’d really, I should be as much of a pressure guy, uh, push you the way that AJ Vaynerchuk pushed me. Because without that kind of pressure, it’s hard to ask.
But I’d say maybe there’s someone who’s listening to us now, Tom, who wants to work with you wants to help out looking for those volunteers and then sifting through and making sure you get the right one is important because just because someone listens doesn’t mean it’s enough. It’s helpful. So I know that’s not your question, but
I want to make sure
Tom: you touched that.
though. I was having a conversation with my buddy today and I said that same as I think I said, I need a marketing intern assistant on the podcast project with me and I’m putting together an outline. Bullet point list of, uh, people that I’m looking forward to collaborate on this.
And it would, it would be light stuff. It’d be a couple of hours a week, but I know they would free me up to be more present and more effective in the conversations. And the thing I was, I was hung up on is something you touched upon. I was like, I feel, I, I feel like is it’s it’s frowned upon to put out a job listing that is unpaid in 2021.
For some reason I don’t is that
Andrew: that’s true. It is know your right to say, I have a free job. A job that doesn’t pay is to say, I need help. Who wants to collaborate with me on this? Who wants to I’ll show? Who wants to do this with me? It’s, it’s accepted to say I’m looking for, um, an apprentice, I guess an apprentice seems a little bit too snooty, but to say, I need help here.
If you help me with do with this, I will show you how I run this operation. I’ll show you how I work with my client. I’ll show you what I do on my own site. You’ll get to do this with me and then we’ll get to, uh, and then you can go and take this off on your own. I think that makes a ton of sense. I’m thinking about.
One of the things that I admire about you. I told you this from the beginning and the reason that you just heard a sound as a, as you were talking was I wanted to come back to you. I love how you do these fricking snippets on your Instagram page. I’m going to say it out loud, just so I remember it and have it in the transcript.
It’s bonus footage as the name on Instagram. I love how you do it. It just it’s clear short videos with this basic, not a base of what the, a clear message. And then they’re interesting to watch how many pitches do I get from people who want to clip my show and then turn it into something meaningful. And it’s all boring as hell.
And you do this thing. That’s so interesting. It doesn’t feel like you’re trying too hard, but you’re trying, and it, and you care and, and you understand that we’re trying to be, um, entertained while we’re going through Instagram. Anyway, I love it. If you were to say to somebody, if you were to say to me, I’m trying to think, is there something I could do to help you out so that I could see how.
I maybe not now because of the book and my work, I can’t do it, but damn, I would love to work with you for free to see how you do that. How do you transform an idea, a simple video, looking at the camera into something that people wanted to watch and care about and that you could feel proud to put out there.
So what I’m saying. You can ask for help and people will do it. Say who wants to collaborate with me on this and learn from, from watching from me. That’s that’s a gift now we’re over complicating it by saying, come work for me and we’re going to have this whole, no, it’s
Tom: This many hours. This is the Yeah. the scription Yelp.
Andrew: I have this idea for how to market, if you come and work with, and if you help me do this, you’ll learn how to do it, and I can help you by showing you how I get my operation up and running.
Now you also have to then stand up. And help them and show them how you do your thing. And that’s, uh, that’s first of all, it’s an obligation it’s commitment, but also it’s a huge benefit to you. I asked people, I asked James Altucher people know how much I love chess lately. I said, James Altucher you guys are famous writer.
Right? Incredible career investor, uh, all kinds of stuff go, dude. Why are you giving me? I’ll spend three hours doing a chess lesson with me. I said, why are you doing this with me for free? And he said, one of the things that he learned was you need somebody who’s ahead of you. You need someone who is at your level and you, someone who’s below, right?
Someone who’s ahead of you to teach you someone at your level that you can just kind of spar against. And then someone who is below that you teach, because when you teach them, you are forced to live. What you, what you’re teaching. You’re forced to say, do I really understand this enough to explain it?
You are forced to actually relearn and to, and to hold onto what you’ve learned. And that’s a huge help. So for you. Come help me with this marketing. I have specific help that I need, but I’m not a freeloader here. I’m going to show you how I do my operation. There’s something gold here. And I want to show you how it is anytime that it does make sense.
You can move on, just obviously don’t leave each other hanging, but I’ll make sure that you learn and you’re gonna get a lot out of it. So I still want to go, I wrote down what your question was, and I don’t want, wanna ignore it, but I want to make that point because AAJ was so incredibly helpful to me when he did that with me, that he was really pushing with.
Tom: How long ago was that interject?
Andrew: It was years ago. It was years ago. This was back when ADA was still actually talking to people at and Vaynerchuk now is like the, the behind the scenes. He must’ve gotten quiet and shy or something. I said to Gary, and in my interview with him, I go, what the hell happened to your brother?
Your whole spiel is everyone should be creating in public. What are you doing? The guy runs your company with you. And he sheepishly said, well, not everybody’s really appropriate to be in public. I think Aja his.
Tom: That’s funny.
Andrew: All right. Um, so you’re saying, what do you do to prepare if I had to here’s what I
Tom: you had a short window of time where like the, the, the core principle, the core things, you would focus on
Andrew: I would go internally and say, what do I really care about? I can, I think everyone else. Anything that this author has to say online has already been said about the book in general, but what is it that I really care about? What do I need to know? So when I was interviewing Neil Strauss, the author of the game, the question wasn’t, how did you get all these women into bed with you?
Or how, how dare you get all these women? It wasn’t all that it was. When you’re persuading at work, how do you, what did you learn there that you can actually use? Show me these ideas that I see amazingly, uh, um, persuade women, show me how I could use them in general. And it was incredibly helpful to have that conversation.
It was incredibly helpful to have that conversation.
Andrew: So go inward is what I’m saying. Do the one thing that you’re uniquely suited to do, and then here’s a trick for reading books. Most. Most nonfiction books, they basically have the premise in the intro. The premise is almost always laid out like this.
It’s. I was living a life. I had this problem. I didn’t know how to solve it because nobody else could solve it. And then I solved it doing this. Here’s the amazing thing that happened to me after I solved it. And then I had to write this book to share that with the world. Right. Boom, boom, boom, boom, boom.
They always do it now. You know what? The upside is, you have their personal story and then they almost always will break down each chapter into explaining a technique that they use to do the thing that transformed their lives have forced them to write this book that nobody else had written before. And if you get the chat, if you get the chapters, if you get that intro, you mostly get the idea.
Tom: So I’m going to take a little lesson from you here. Uh, let’s go into it. Why were you so compelled to. To write this specific book with this specific direction. You’ve asked a lot of questions. You’ve, you’ve had a lot of conversations. There’s other people with books on how to interview, how to podcasts
Andrew: I don’t think there are there. I don’t know how to podcast. I don’t think there are books on how to interview. I, you told me are
Tom: aren’t there No, no, you’re right. You’re right. There’s that specific thing. When I saw the title, I, I signed up for the intro chapter, like, I’ll say, oh, I want this now. Like I saw it. And I was like, this is what I’ve been looking for.
Andrew: That was by the way, one of the best things I did, I said, I will, I need some beta readers. Let me send out the chapters and tell me, give me some feedback. Tell me what you think. It was big feedback that helped adjust the book, but even little ones, like one guy said, dude, you misspelled this one guy’s name.
I said, how do we misspell the person’s name? And then we went back and we fixed our process to make sure that we got it. Actually, the publisher had it, but I want to make sure that I don’t misspell someone’s name because the whole thing is stories about how I did it. So the thing that made me feel compelled was there all these books about how to learn from books.
There are all these tips for how to learn from blog posts from this, from that the one source of information that can give you unique answers that adjust to your needs is other human beings. And there is no book on how to do it. What there has been over the years is first of all, interviewing as a, as a.
As an output, not as some way of a reporter learning something and writing an article I thought was around for thousands of years, it’s about a hundred years old. Um, if you take a look back and I, I challenged people, you can hardly find any, uh, interviews that are published. Before about a hundred before, uh, before the Dawn of television, they just, it’s not an output.
It’s a source, a way of getting information. And that’s the type of thing that blew my mind. And then I started racking my brain. Then I did a challenge online. I offered to pay people if they could find me early interviews and just get a sense they’re not out there. It’s a new, medium. Um, the thing, uh, I want to go like into the history of, of interview, I’ll go into it a little bit.
Apparently what happened was
Tom: Yeah. I would love to.
Andrew: here’s what happened. There were these, um, Famous, uh, movie stars and TV stars who needed to appear on television shows, but they couldn’t keep being in sketches. It became a lot of work for the star to be in a sketch. And it became a lot of work to create a sketch for each person that would make them shine.
And so if you have a host, who’s doing sketches and the early version of television with celebrities, they need something else. They decided. All right. What if we sit down and do an interview and the sit down interview as an end product that people watch. News programs then wanted to feed off of this entertainment style approach and they started to do it.
And so you started to see what we now know is like the 60 minutes type interview or Oprah did great ones. Diane Sawyer did great ones. Barbara Walters became known as it. Larry King became known as the interviewer, but here’s the. Larry King Barbara Walters and others had all written books on how to do interviews.
Supposedly they called how to talk to anyone. I think Barbara Walters did it. Larry King did it. I won’t even tell you Tom, how much work I went to go and find the Barbara Walters book on how to talk to people. The interview book she did though, what everybody else who’d written, who, who done interviews and written a book on how to do it?
She turned it into how to talk to anyone with just a few anecdotes from her interviews and a lot of how do you talk at cocktail parties? And the reason was that before, about 10 years ago, 15 years ago, when podcasting and interviews with available, the average person couldn’t do it. So if you’re a Barbara Walters fan, you’re not watching her.
Shit. I got to go out there and do my own interviews. Like Barbara Walters, ABC, come on. No, there was no way for them to do it, but they cared about her. They want to know a little bit about her process and how they could do this in their lives. So she started off with a couple of interview tips, and then I swear to you, she gave makeup advice in her book.
The woman who gave, made, who made leaders of countries just wins and get angry and reveal themselves as revealing to you, what type of makeup you should wear. Right. And so that never existed before. All right. So that’s why I decided I had to do it. I had. This is a thing that I learned. We now have all these people, we could interview.
It’s a gift that we can do it in new software’s being made available all the time. You and I are now talking on Riverside FM, which makes it easy for people to record interview style podcasts, but you know what, they’re more and more tools coming out there. There’s Twitter spaces, which we know there’s racket, which is specifically built for quick interviews.
So we now have access to people we admire on. Off-camera on internet, et cetera. But I would even say beyond that some people have the same kind of experience that I’m. Am I renting for too long here? I might
Tom: I love it. I’m here for it. I’m not as let’s run it.
Andrew: Right. Like, I’ll go with one less step. Some people have the same kind of experience that I talked about in the intro chapter of my book, which is I got to talk to one of the legends on wall street.
His name is Alan Greenberg. Nobody called him Alan Greenberg. They called him ACE Greenberg because he was just such a Maven of wall street. Right. I get to talk to him because I’m an intern making no money for somebody who he doesn’t even know works him because this is a big investment organization.
Right. I sit down with. I don’t know, he’s given me an opportunity. He wants to teach me, I don’t know what to ask him. And I’m asking questions and he’s telling me answers that I saw. I literally saw them in fortune magazine. I literally saw them in Forbes. Cause I knew my shot was there to meet the great man that I could then eventually work with or learn from and use.
And I didn’t know what to do. Um, and so. I kicked myself. I said, I finally had this opportunity. I remember I then had a full-time job or not a full-time, but a paying job beyond that. And I remember I went to my boss, Paul, so Berra and he goes, what did you learn? What did you learn? You got to sit next to this guy.
We all knew him. He told me legendary stories about him. What’d you learn? And I said,
Tom: it’s in Forbes.
Andrew: Let me get me for his magazine. I said something even dopey, or it was something because the biggest thing that I learned from him was he gave me something that was a cliche. And I knew it out. As I walked out the door, he stood up before, like to end the awkwardness. And he said, Andrew, one of the things I learned from my boss was if you love what you do, you never have to work a day in your life.
All right. Thank you for coming by. And I go. Okay. Maybe there’s like some deep wisdom in there. Maybe. I know it sounds like a cliche, but this is the thing I got. So I’m going to hang on to it and see if I could find meaning in it. And there’s obviously meaning, but that could have found out a fucking cork chew fortune cookie.
I shouldn’t curse here.
Tom: That’s all right.
Andrew: free to bleep it.
Tom: that’s all right. We’re we’re we’re
Andrew: angry and worked up.
Tom: We’re rolling here. I, I love, I mean, that’s the way I am when people interview me and I, and. I, uh, you know, that this is the time, this is the time to share that this is what I’m asking. This is, uh, this is why you’re on the show to, to go deep into these subjects and to get like these, these nuanced interactions that made this book possible.
And, um, you brought up, uh, I in the process of, of, of you going deep in there, it, it clicked to me that you started. Career creating this podcast, your interview show before the word content was even a thing, you know, you were just like, why did you even want to go that direction? And then how cool was it when you, did you have that sense in your mind?
Like, oh, there, there could be a business around this or was it like, oh, this is just a natural progression of me following my passion and content. We can, we can contents attention, attention sells. Let’s let’s
Andrew: didn’t even have that. What I had was when I graduated from school, I wanted to create an and I wanted to create a mag. And sell subscriptions of it. I said, I know people still pay for subscriptions for paper. I can make cold calls. I want to create a magazine with, uh, biographies of people I admire because there was a period there when Forbes magazine created something called audacity magazine.
And I loved it so much. I hunted down. Mint copies of the magazine. And I wish I hadn’t thrown it out. Maybe ask her, you don’t want to hold on to stuff in life. I don’t. Anyway, I, I want to pack light, but it was so beautifully written. These stories that, that had a clear message of people you didn’t know that you could learn from more than you would in school.
And I wanted to create something like that. And I said, I could sell it. And if I get a subscription, then I can keep rolling it over. And then I end up with a real big business. Meanwhile, my brother created an online dating site and I said, oh, maybe I should go to online. There’s more money in that. But I still love the idea of storytelling and learning from entrepreneurs who, who built, who built the world for us.
And so, anyway, that’s the background. Then I started hosting these events and. Uh, Microsoft sponsored them and Lynn Lang who worked for Microsoft at the time said to me, Andrew, we’re happy to sponsor, but you need to do a better job of telling people about the events. I said, I’m sending out invitations all the time.
She said, no invitations. That’s great. I see you’re packing these places up. What you need to do is show people who didn’t come, what was going on here and broaden your reach, which I then understood later on also helped her with her reach. And it wasn’t just that she was getting more eyeballs. She wanted to be able to go back to the people at Microsoft who were funding her to fund me and say, we back this thing.
Now, if it’s this thing, that’s a femoral and happens, um, in, in, uh, in someone’s office is like this big party that I through. It’s not a thing. You can show anyone, but if I could do something, it would be. It would be an event. It would be content that you could then take to her bosses. And so she pushed me, she pushed me.
And then finally I said, you know what? I’ll interview the people who came to the events. And I started interviewing them. And then I interviewed this woman who, over the years, we’d done millions of dollars in business with I’d been to her house. She’d been to my, I didn’t really have a house at the time, but she’d been to my office.
We’d had dinner for, for years as we just kept working together. And then I said, let me interview you, let me go outside of my, my, uh, people who come to my party and interview you. And I got to hear her story. Like I’d never heard anything. Because, like, I never heard her story before because when I had dinner with her, it would be awkward to spend an hour going deep on how she started her company, where she came up with our idea.
It, it feels too one sided. If I, if you know, you just, you don’t have places in life where you could press, but here I had an hour to ask to see who this guy was, what you did there, what she, why she ended up with this company, what happened when she took the company public and so on. And so is her name was Roslyn.
I published that interview. I remember them looking over my wife. I said, I found the thing I want to do for the rest of my life because now I get to, I get to see these exciting stories. I used to love reading in real life, customized to my needs and have conversations with people that I thought I knew in a whole new way.
Nobody had ever done that before.
Tom: Yeah. And w early on, did you sense that you had a strength, a knack for having these conversations or, uh, you know, and, and, and what has changed? Um, let’s say from. Not, not what has changed because probably a lot has changed. Uh, but I’m like, what are like key things that made you get from like that first interview to your 200th interview?
Like what are key things that like made your inner interviewing process that much better for your guests? I kind of asked
Andrew: Eh, what I would have had in the beginning was imitation. I really liked this American life and how thoughtful they were. And so it was. What you’re about to hear in this interview is a conversation about something I’ve really been wondering about. I had a style copied almost exactly. But I did also have sincerity.
I knew that I was on some online webinar where someone interviewed, um, it wasn’t an interview, but she was kind of introducing a presentation by Seth Goden and then these two other authors. And I thought it was a great idea, right. Seth gets to bring his audience in and then he gets these two other famous authors in.
So now I get to hear Seth and I get to hear his two other famous author people. And it was great. And then they all get to like expand their audiences and this whole thing. But when she introduced. She said something that just rubbed me the wrong way. She said, and now we’re going to hear from Seth Godin, we’re going to hear his secrets, his marketing secrets.
I said, they’re not his marketing secrets. The guy fricking wrote a book. He’s trying to publish eyes size that you can’t, when you’re, publicising a book, you can’t call it marketing secrets. And I, and obviously that’s a little thing I’m being pedantic there. But the thing that bothered me was I could see she wasn’t being sincere.
She. Being a performer. She was doing the things she thought she needed to do, which is introduce him and give the thing that he was doing some specialists. And what I wanted her to do was just be open and say, I followed this guy for years. I can’t believe I’m allowed to be here. The thing that I liked about him was he said, purple cow.
And then I decided to create this little thing. And that’s what happened to me. And because of. I got to grow my business a little bit, and I want to hear a little bit more and frankly, be a little more connected to Seth, just do it. The thing that’s open. And I said, since I hate the way she’s doing it, I have to then do it the way that I want and not hate myself.
And so I would be open and I would say things like, um, I’m not comfortable in this interview. I feel like I screwed this up. I feel like I’m going to two week here. And that helped, that helped a lot to be that sincere.
Tom: Yup. Yup. And then, and then, uh, man, there’s, there’s been a couple of tangents from like, oh, I want to, I want to pull from that idea. I want to pull from this idea. Uh, we, we touched upon, uh, the things that you. As far as when, um, you’re putting the content into the book and you’re trying to put all of your ideas into 200 pages around 200.
How many pages are we talking here?
Andrew: I don’t know. Um,
Tom: don’t know yet.
Andrew: we don’t know yet. All I have is the Google doc, which was like 160 pages. I
Tom: It’s a beautiful Google doc. How do you decide, um, like who, who are you talking to directly in this conversation? Is this someone that is sitting on the sidelines and is like, I’m curious about getting into a podcast or is this someone that is 300 episodes in and they want to get better?
Or is this going to apply to both of those people?
Andrew: That’s gonna apply to both of those people, but only people who want to learn through this, like structured inner or through an interview. Um, Actually learn from other people through conversation. Um, if you’re trying to grill someone and pull that information and get that aha gotcha moment so that you can make it on CNN or Fox or whatever, I’m going to be horrible for you because all I want to know is the depth of the person.
If that’s what you’re trying to do, whether it’s in one-on-one conversation, that’s never taped and nobody hears it except the two of you or you and the guest at a fireside at a big conference where you’re sitting down and getting to interview the person on stage with a big audience. And it’s going to be recorded for everyone else.
It’s that? It doesn’t matter to me how big your audience is. It doesn’t matter to me how experienced you are. I want to show you how you can tap into the experience, the knowledge of the other person and make it applicable to you and people like you. And so what I did there was I started to think about who these people would be.
And I was very slow and writing on my own. And then I hired this, uh, editor from penguin. I said, her name is Marisa. And I looked her up. She’s involved in amazing books. I said, can I hire you to once a week, just hold me accountable, make sure I’m actually writing the work. And then tell me if what I’m writing makes sense.
And I learned a lot from doing that with her, but one of the things that she did was outside of the writing process. Ask other interviewers, what problems they have. And that would be one of my assignments for the week. He said, let’s just take a break from writing. And so I would reach out to other interviewers and say, is there anyone who needs any help?
Let’s do a one-on-one call. Let’s just see if I can help you out with anything. I have all this experience. I went to some Facebook groups and I offered it and people thought that I was. Uh, I don’t know what sucks email address is out of the network or solicit. No. All I was trying to do is be helpful so that I can see what problems they had.
And so I did that with new people. I did that with people who started in closed their podcasts to understand why they shut it down. I did it with people who had never podcasted before I did it with people like it, depending on the weekend, what we were working on, it was don’t just think about. What you imagine they need, if you’re stuck and you can’t write, let’s just get away from the page and go and do an assignment like that.
And that helped me. And so it’s written for anyone who wants to learn from a conversation with someone else. And it’s based on the problems that people who I’ve talked to have had, and the experience that I’ve had doing it myself.
Tom: Yup. And, uh, there’s, there’s, uh, an idea that keeps popping up that I’m having in the back of the head that I Ys want to, like, I want to share where it’s this idea that I believe so much in this medium, and I believe in it from the aspect that it’s. So much as you know, obviously it’s a good way to get into, you know, if you want to build a business around it, that’s a great way to go.
But the way I see it as this is like shooting hoops for me, this is like a week. This is like picking up kayaking. You know, some people go hiking, like I love doing this. This is my hobby. And I’m starting to realize, you know, I’ll have these conversations and after the conversation, I’ll go up and I’ll tell my wife about the, you know, I can’t believe like P this is actually a thing that exists.
You can have a conference, you can reach out to someone that you want to talk to. That is established, that has done things that you really admire have a engaging conversation with them. They want to do it, and then you get the call it content and put it out and more people want to listen to it. And I’m curious, like there’s a lot of things that I can.
The other thing about podcasts too, as a consumer. Um, as a consumer, the idea that I just get the eavesdrop on my idols conversations, I get to hear an hour long conversation with Jay Shetty and will Smith. Like what, in what era? Like my parents didn’t have access to. 50 years ago, and I’m getting all of these perspectives of people’s everyday experiences that I’m able to, uh, apply to my everyday experiences.
So this is more just like a rant about my, like, love for this, this meat, this medium. And I’m curious if it, uh, w what are some of your favorite things about this, this format besides the, the, you know, building a business around it?
Andrew: I think that, like you said, that passion for this is like a hobby. It’s amazing. I asked, um, I sat down with David Rubinstein. He’s the founder of the Carlisle group. This is a multi-billion dollar investment firm. I said, you’re not in a company. You’re spending time interviewing on stage at events. Why are you doing this?
You could do anything. You want, why interview? And he said, why are you interviewing? And I thought, well, that’s it. That’s not the answer I’m looking for. But then he
Tom: might have been in there though.
Andrew: like he said the same thing. It’s the same reason that you, Tom are interviewing an I Andrew and everyone. It’s he, he’s curious about people.
It’s the same reason. Some people read books. There’s a sense of curiosity that can only be satisfied in with certain mediums. Even though he’s a billionaire and accomplished, even though he could do anything with his life, he is choosing to do interviews. So the question is, why am I doing it? What am I getting out of it?
It’s the same stuff you are. It’s intellectual satisfaction. It’s the connection with the person. I’ll say sometimes in my podcast, I’ll interview someone and then I’ll say, I’m in San Francisco. Can I come out and meet you right now? And we’ll go. And sometimes it feels weird, but we’ll go and we’ll hang out together.
Or they’ll randomly bump into me someplace. And we did the interview and we have a bond because we stared at each other and they, and we asked each other about, or in my case, I asked them about the most personal things in their lives about the biggest successes. And when you share that, when you talk about that, you can’t help, but feel a bond with whoever you’re doing that with.
There’s a reason why therapists are no longer allowed to have sex with their clients, because there’s a connection that you have with them. So.
Tom: So true.
Andrew: So thing that I would say though, is not, I don’t wonder anymore why David does interviews. I wonder why other people don’t and I think the answer is there, they set up too many barriers.
They want to edit the interview, right? So it sounds polished. They want to do too much research because that’s what I say that I do. They want to put it on a podcast app, which then takes a long time. The win is to start with as simple as possible and be consistent to say, I’m going to do a Twitter spaces.
I’m going to do an Instagram live every week on Monday. We’re going to do it and forget about who is in the audience. Forget about how many people in the audience. Just talk to the one person and be done. That’s it.
And, uh, I’m glad that you brought that point up because I actually, I started a podcast a couple of years ago and I had these kind of like these grand goals for, uh, you know, amount of listens amount of metrics like these, these vanity numbers to go to. And when I revisited it, this. I decided my goal was, is going to be reps.
I just want to get better at having these conversations. And so much of the marketing of these comes from one, the guests, uh, you know, telling their friends or, and sharing it. Like it, it, the marketing is built in. So I don’t have to worry about that. If I can just get better at asking the questions better at vetting the guests and, and really aligning.
The direction of the podcast, uh, to a certain number, like right now, it’s to 30. And I was just like, let’s just do 30, put my head down, blinders on record 30 episodes, and then look at it next and then be like, all right, what’s the version 2.0 of this. And, and I’m starting to get to the point where. People are reaching out for sponsorships because I, you know, they’re seeing my, my, um, voice in the creator economy.
They’re seeing the connection on both the tech doc and the Instagram. The podcast doesn’t have as much, um, listeners as compared to those. But like the, the listener time is extended. You know, people are hanging out with us. They’re like on the toilet, listening, listening to our. Know, I mean every, yeah know whatever going for walks with the dogs, maybe not on their toilet.
Um, don’t listen to the show on the
Andrew: maybe on the toilet, listen to it on the toilet.
Tom: Yeah. So, uh, whereas I getting, oh yeah. So do you have suggestions around, uh, handling those conversations? Cause there’s a couple of brands where I’m like, these are actually really cool brands. I don’t want to undervalue myself. Uh, but I also, they would be cool to do an integration and I’m kind of like, it would almost make the podcast feel a little more.
If I did, if I had a sponsor. So do you have suggestions about how to integrate and like when might be the right time to start integrating with ads?
Andrew: I think a anytime is fine. And I know that Gary Vaynerchuk used to say, don’t. Don’t put in advertising revenue for as long as you can, but I, I agree with you. I think people is take it more seriously when it feels like there’s a real business and you’re not just hanging out and posting stuff the way their friends might post their kids photos on Facebook.
And I think it adds credibility to it. I think you also learn a lot by, by starting to sell ads early, maybe even before you’re fully ready. What I did with. I found a sponsor. It happened to be fresh books that was interested. And I said, I don’t care so much about the revenue I care about. How effective is this?
Why do you want to advertise? Why do you advertise with me? Why do we advertise with others? What are you looking for? How do you measure success? If I charge you a dollar, what would you expect? If I charge you a thousand, what would you expect? Give me the thing. And then I gave them a price that was guaranteeing the result.
And under priced it based on what they said, but I said, look, all I want is give me feedback, tell me afterwards, did this hit the metrics? And then they said, no, and I have the fricking email. And I went back. And when I wrote the book, because I wanted to find the email where they said yes, and I couldn’t believe that even that offer, they said no, because I was underpricing it.
I was guaranteeing it. They didn’t have to pay me. And it’s just 650 bucks. So anyway, um, they said, no, but then I pushed and I said, I guarantee this will work. This there’s no risk here. And so they said, okay, fine. Let’s do it. And they did it. And I sent it by the way to Mike McDermott, the founder of FreshBooks and the team that said yes, over fresh books.
And, um, uh, we had a laugh at that and we reconnected because of that. But the. When they said, yes, what I kept wanting to know is how effective is this? They want, they actually were looking for something that your sponsors are not, which is specific conversions. How many people were going to try their invoicing software.
And if they could get a certain number of people at, I forget what it is. Let me just throw out a number for now $10 per person who tries, tries using their invoice software. They knew that they would make a profit on it. And if I was charging them $750 or 650, let’s say, yeah, I think it was six 50. And I could get them seven people to sign up.
Then that is not good. If I can get them 700, that would be great. Right? Like we knew what we were aiming for. Um, and so that’s, that’s what I, I did with them. And then I kept looking for data and because I was so data hungry, I even went a step further since I knew they were looking for conversions. I said to everyone in the audience.
If you use their software, invoice me, I’ll be your first invoice. Send me an invoice. And I did that. So I can count to see are they are their numbers, right? Obviously the numbers were right. The important thing though, is once you get that and you say, okay, now I know what it’s worth. You can go to other sponsors and say, look, this one customer said that they told me what their needs were.
I gathered for them and there’ll be a reference. So with the first customer, it’s not so much about, about money. I love your soft. I love your software. I love your product. I love what you’re doing. It’s not about the money for me. I’ll be honest with you. It’ll be about the money in the future. So I’m not like a woodsier, it’s not about the money.
It’s about the data. Tell me what your goal is. And throughout tell me how close you’re hitting it. And that way I can use you to learn from you and improve, and frankly, to point to other people and say, look, they got the results. So I don’t need money. I will charge you something because it’s a business relationship.
But what I have to have is, uh, I’ll give you a great deal. I have to have data. Tell me whether it’s working with.
Tom: Yeah, and I love that approach because you’re looking at it as a long-term relation. Instead of just this one-off transaction where, oh, this is going to find my content. And I, you know, a lot of these brands, they have a lot of people they could send their sponsors to in, in, in this day and age. And they, it has to be really nice on their end that they know that you care about the actual return.
It’s not just, Hey,
Tom: send me what you got.
Tom: Um, so I w I would love to, uh, there’s one, there’s a couple more, a couple more, little quick kind of questions here. Uh, the one is. You alluded to it in that conversation, you said what’s your goal at the beginning of those conversations? Do you, do you bring in your question, what would make this a win for you?
Or is that more just the podcast format? Because, and can we go into that? Is that something that you discuss in the book? The, that, that question to kind of
Andrew: I do. Yeah. I asked it of you and I didn’t even realize it. It’s just a habit. Um, what I used to do was, um, I would have these guests who would just go rambling on stuff, promoting. that I’m, I’ve got a book of my own. I understand why they would promote their books when they had a book or why they promote their software.
And they have one, like for me, I signed up with a new publishing company because I love startups. And so Ben, who, who founded it is investing so much of his time in this book that he’s publishing for me from a damn gravity is his name of the publishing company. He he’s spending his time making sure that I booked myself to do a few interviews that I tweet out that all that.
I now feel the pressure, not just for me to sell books, but for him to know that if he’s investing this time, that people will know about the book. And it’s so much pressure that I would, if, if not for you, before we got started asking me, what is it that you want? I would say that I don’t get lost in conversation.
I would have written down on the iPad that I have look right here in front of me. I would’ve written down on this iPad, make sure to mention the book and then I would have promoted it out of anxiety, how to making sure the Ben was satisfied right now. The people that I interview, they have beyond the bend in their lives that they want to make happy.
They have their parents or their, their kids that they want to earn money for and so on. And it creates such anxiety that people promote and promote promote. So what I decided to do was to, before an interview, I started asking them, what’s your. What’s the win for you? What are you, what do you, what’s your ideal out of this interview?
And once they, they heard that I literally could see in their faces, you could go to my Instagram account. I’m not big on using Instagram, but you could see this one clip that I showed of what a reaction looks like. When I say it, the person goes from tense to ha Andrew cares. And he literally says what many people say, which is the fact that you asked is a win.
And then they tell me what their goal is. And I can say, oh yeah, I can hit that. You’re trying to hire. Oh yeah. We can absolutely make sure to mention the hiring page. So you don’t have to keep talking about your culture and making sure that someone knows that you’ve got a slash jobs. And so that’s what I do before the interviews.
It’s a big thing. Try to do that. Even within a calls, if somebody is calling you, because maybe they heard you on this podcast and they’re asking you for help before the call say, before you start saying, look, actually, there’s something else I would do before this. But if it’s a personal non-recorded call, one of the first things I say is what’s a win for you here in the next 15 minutes.
What’s the ideal goal. The one thing I do beyond that in a personal call is I share something personal before we get into business. Sorry, not a personal and a business call. I share something personal so that we get some connection to each other, and then I go into business, but what’s a win for you.
Very big, very important. Do it in business calls, do it, do it wherever there’s like. We got to get down to action.
Tom: work calls, collaborative, any creative calls with teams instead of, you know, going off on a tangent. You know, obviously when you’re collaborating with other creative minds, you could, there’s a lot of things that you could try to solve in that conversation, but what’s the most effective thing here.
Where, where do we want to sail this ship?
Tom: So at the beginning of the call, I talked about my wind, uh, selfishly I said, uh, my win for this would be if you could school me on how to improve my, my ability to lead a conversation in a podcast. What’s w w what’s wonder three tips. I don’t want you to give me 10 tips.
I don’t want to feel so bad. So maybe one of the three tips that I could do to improve my delivery of my questions.
Andrew: I thought you were good. You can see how lit and on fire I was in this interview, I thought it just felt great. Um, and I think part of it is, and just the conversation we had before we got started, you shared a secret with me before we got started, not like this big secret, but it was a little bit of a work secret.
And so it created a bond and a trust, right? If you’re trusting me not to spill the beans on your thing, I could trust you not to take me in a bad direction. That was really nice. Um, And so it gave this, this conversation a real, a real friendly and comfortable vibe. Um, The one suggestion that I have is, I didn’t know where you were going with this interview.
I wasn’t sure where the actually I’ll give you two. I wasn’t sure where we were going. Are we going to talk a little bit about the book? Because I said it’s a win. And then later on talk about, um, online businesses or. Someone just recently asked me about Austin, because we’re now in Austin and they want to know about the city.
You just never know what’s the direction the person’s coming in from. And sometimes an intro could help with that sometimes just saying upfront, before we get started, Andrew, my goal for this is to understand this one things. And if we go in different directions, it’s fine, but that’s the
Andrew: So that’s a, that’s the most important one.
The second one was we had this little interaction before we got started, where I opened up my calendar and I was looking for the link and I couldn’t find it. I think I using Calendly to book these or my using Calendly.
Tom: I’m using Calendly.
Andrew: I think we’re on your Calendly. I think you should go into the settings of Calendly and make sure to include a link to Riverside where you’re doing this and make it now.
I know why you didn’t include it. You didn’t include it because you have to add different Riverside link for every guest.
Andrew: So one thing you could do is create one generic link within Calendly. I mean, one generic link within Riverside that you just call your studio the in Tom’s interview studio and have every guest show up at that URL, get the guest URL and just put that into Calendly and have it into every one of them.
Test it out. You’ll see it. I prefer that because now everyone is in a single thing and it’s all easy to get. If you don’t. The other thing you could do is I’m, I’m wrapping here, but I’m going to close it off in a. At least in the calendar include your phone number and say a few minutes before the interview starts, I will email you the thing.
Here’s my number in cases, an issue so that if we’re looking at the calendar for the day, there’s no doubt. We see exactly where Tom’s going to go.
Tom: Yes. So you’re not sort of up in the air, like, all right, well, where, what am I clicking? What am I clicking for this interview? Yeah. That th that sort of stuff is the, um, Th I can definitely improve in those areas, that kind of button up the system behind recording the episodes and publishing the episodes.
And, uh, I appreciate that. I think that that helps so much on my end end on your end. So we can just focus on having the conversation.
Andrew: And truthfully, that’s not as important. It’s as you co as you go on, if you see Andrew just emailed me, I think he’s the third person who emailed me saying, where do I go? How do I solve it? You know what, the easiest way to solve it is to go to the Calendly link and put something in. So people know it. I see another person doesn’t really know who I am.
Doesn’t have a sense of who I am because they didn’t hear the full interview or they keep apologizing for not listening to the whole interview. What can I do? I know what I’ll create this 4.4 bullet points about what they want to, uh, what they might want to know before the interview, or I’ll just create a clip of the interview.
If I have the patience to go in and clip out, um, one of my past interviews, so they could see that, or I don’t I’ll link to my LinkedIn or my bio or whatever, but as you find a problem, if you see that it comes two or three times, say how do I add that to my system to fix it? So it never happens again.
Tom: Yup. Totally. I appreciate that. And I think too, a lot of my, all of my guests, there are movers and shakers of some sort. They have a lot going on. From my end, um, the favor that you’re doing and coming on the show, I have to make it as easy as possible for you to just show up, do your thing, uh, and, and make sure that, you know, you’re in like a safe, uh, you know, space to have a fun, engaged conversation.
Andrew: Yeah. Yeah. And that comes as you build it up, you just going to keep doing it and doing it and doing it. Then when somebody comes in and says, can I help you do this podcast so that I can learn from you? They’re not going to see something that is obvious. They’re going to see a few things that make total sense, but they wouldn’t have thought of before.
And you could even say something like, just copy my Calendly link or go through the right. And now you’ve got some real value there for someone who’s coming in and working with you.
Tom: Andrew. This podcast. I gotta be honest. If I can share something with you. I was nervous for this podcast. I feel like it’s like, um, I’m looking at the LeBron James of asking questions right now. And I, it, that gives me, you know, I’m like, okay, he knows this space. So well, I, you know, most of the people I interviewed, like they’re not professional interviewers, so I’m like, he’s going to look at me.
You know, if I’m playing basketball with LeBron, he’s going to be like looking at my forum, looking at my elbow. Is it in, you know, how am I carrying myself? So. It was an absolute pleasure to have you.
on the show. And I learned a lot. Can’t wait to go back and listen to this one again. Cause there were so many little nuggets that I just want to imprint in my memory and take down where let’s talk about the book, where can people get it?
Where can people expand, um, on this conversation? Uh, and you know, what’s the best place to find it.
Andrew: It’s going to be in just about every bookstore. Actually. I only care about the digital bookstores, so it’s probably going to be an online bookstores only. I don’t care. I don’t even know about the others. I don’t care about them actually. You know what? That’s a rude thing for me to say, because a lot of people do care about physical bookstores.
My wife and kids do, for example, all right, it’s going to be in bookstores. Um, and it will also be available on. And it’s coming out in the middle of October. And if anyone just wants to get the what’s there now, um, and just see some of the chapters, give me some feedback, use it. Uh, right now I’ve taken the best little tips that work instantly.
And, uh, we’re emailing it out to a few beta readers. And if you’re interested in that, go to stop asking questions.co and be a beta reader. And I really appreciate all the people who are catching things like my misspelling of someone’s name. That’s.
Tom: So the actual title is stop asking questions.
Andrew: Stop asking questions is the name of the book. Exactly. Now we know why
Tom: So search that into anywhere and go find that book and let’s help Andrew with his spelling on that book and also get some amazing insights while we’re at it. Andrew, thank you so much for being on. the show.
Andrew: Thanks Tom.