My process for deeper conversations

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If you’ve been listening to my podcast for a while, has it ever felt a little uncomfortable to hear me get so open with people? I didn’t realize that even my friend Wil Schroter noticed it.

Recently, he invited me to go onto his podcast, Startup Therapy to talk about how I get so open.

He’s known me now for years and I guess he’s been curious if you’ve been curious about it too, you’ll hear him ask the kinds of questions you might’ve been wondering and hear my process.

Wil Schroter

Wil Schroter

Wil Schroter is the founder of, a startup launch platform.


Full Interview Transcript

Andrew: if you’ve been listening to my podcast for a while, has it ever felt a little uncomfortable to hear me get so open with people? I didn’t realize that my friend will Schroeder noticed it, let alone appreciated how open I get in conversations. He invited me to go onto his podcasts, startup therapy and talk about how I get so open.

He’s known me now for years, and I. I guess he’s been curious if you’ve been curious about it, you’re going to get to hear him ask the kinds of questions you might’ve been wondering and hear my, I was going to say, yeah, I will say process. Here are my process for going deeper in conversations and we can do a thanks to HostGator.

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My guess is you’re going to love them the way that I have for years. If you go to, you’ll get the lowest price they have available. That is host All right, here’s the interview.

Wil: Welcome back to another episode of startup therapy. I’m Wil Schroeder, the founder and CEO of And today my co-host is none other than my good friend, old friend, Andrew Warner, the founder of Mixergy, Andrew and I have been friends since Oh boy, 2000. Eight, you know, long enough, Andrew, that I remember sitting across from you in a bar in Santa Monica, listening to you.

Tell me about how you wanted to make mixer G like your career and interview founders. And so here we are full circle, you know, you coming on our show to talk founder stuff. And so Andrew, you and I together again. Welcome.

Andrew: Thanks for having me on.

Wil: Yeah, no worries. Excited. I could literally talk to you for hours here, but for those of you who haven’t visited or seen any of Andrew’s interviews, it’s an.

Absolute must-see. I mean, every time he does an interview, he’s so focused. He’s like the godfather of all of this stuff. He’s done over 2000 interviews, which I think this is episode 74 for us. I can’t even fathom how many interviews that is. And he’s literally interviewed everybody at this point and I’m like almost every other interviewer, he gets way, way, way into the details of how founders think and how these businesses work.

Which is exactly why I wanted to have him on to host the show with me today. So, Andrew, today, I want to talk about why founders have such a hard time being transparent, being vulnerable about their startups and really themselves. This is something that, uh, you and I have talked endlessly about over drinks for a long, long time.

Yeah. And so, you know, what was funny is one of the last times we were together on San Francisco, you actually told me. That you wouldn’t have me on your show again, because you didn’t feel like I was transparent enough for you. So I. It kind of makes sense to start there in your mind. I have to ask why don’t you think founders, you know, cause you interview thousands of them really like me are more transparent about their startups.

I mean, like, you know, what do I need to do or anybody to get back on your show? Uh, in a transparent way.

Andrew: First of all, I didn’t feel like you even wanted to be on now on the interview at the time, I felt like you were at a place where you thought you were too good to be on that you were all blowing up, that people were giving you major investors were giving you $20,000 a piece just to help you think through what your businesses were going to be.

That’s where I felt you were, but before we get to you out, but I’m about myself. I have to tell you that I have felt really bad about being as open as I am. I remember specifically hiring, um, an interview coach. I was watching this interview show on television. The interview was fantastic. I said, I’ve got to get the producer of the show to come and work with me.

And he and I worked together. Every Monday, we would go through the transcripts of my interviews from the previous week and go over all the things that I did badly. And he would try to tell me the things that I did well, and I wouldn’t listen. And one of the things that I remember saying to him was that’s stressful.

Why do I have to be the big loser of all of the internet? And he goes, what do you mean. I said, Jeremy, everyone else online talks about all they do is they talk about the things that do well for them. They’re promoting the great comment that they got. They’re promoting the fact that they got a win. If they have like, if they’re whatever popped on a chart, even just a little bit, they take a screenshot and it’s like blessed and celebrate and all that.

And me, I have to talk about. How challenged I am to, uh, grow my business, how challenged I am to have a relationship with my wife, whatever it is. Yeah. So is I’m bringing it up. And I feel like all I’m doing is doing the, the loser stuff. And then when I’m doing an interview and I talk about it, my guest gets to be the shining entrepreneur on the Hill that we’re all looking up to.

And this guy, Jeremy, we were on a call and I lost him. He stopped paying attention to me. Now he looked at the transcripts, Google doc. I could tell because you could see, you know, in a Google doc, you can see when people’s mouths. Smooth. So I was watching that, come on, Jeremy, just respond. I just laid it out for you to respond.

And he said, Andrew, after a minute and a half, he says, look, this is the part that you’re worried about. I said, yes. And he goes, Well, look, you’re scrolling down and she is telling you how her mom was really rough with her, how she feels a sense of inferiority because her mom always said, you’re not good enough.

You have to get an a plus because an a is not enough. Now, Andrew, he said, You’re expecting that because you are vulnerable that she’s going to be come back and immediately respond to your next question with vulnerability. It doesn’t work that way. This isn’t a falafel stand on Bleecker street where you pay $5 and you get a falafel instantly you share, and maybe they reciprocate and maybe it doesn’t happen right away.

It happens later. Or maybe it doesn’t happen at all. It’s not, it’s not a transactional experience. But by you sharing this stuff, other people feel free to do it. And if it takes them a little while, be okay with that. And if they never do it, understand it, but this is why you should continue to be vulnerable.

If you want your people, your guests to be open with you. That’s why. And the same thing happens in private. All right. This is not a business thing, but you, you told me before we got started, we should talk. We should be talking about the personal side. Can I talk a little bit like sex stuff? Yeah, absolutely.


Wil: You sure? Yeah. Oh God. Yeah.

Andrew: I’m not going to go too far with it, but I’ll tell you this. We have a friend. Who is every time we hang out, he is like the rockstar of the night. Right? Seriously. He walks into a fricking bar with us. People are high fi strangers are high fiving him. I swear, I swear, this is, I saw this happen and I’m like telling them about the problem Olivia and I had the last week.

And if I didn’t, I don’t think he’d feel as comfortable telling me about how. When he was having sex with the last, like the last few months, all he was thinking about was one other person as a way of going through it as a way of enjoying the experience. Because if he was too much in the moment, he couldn’t give himself into the moment enough, because he’d be afraid of.

You know, not, not performing or not being what he was supposed to be. And by maneuvering his mind to this other experience, he was able to bring his, his body to, to the experience he was in right now. Anyway, the reason I’m saying that is there’s a vulnerability in that, that, without me being able to tell him about what’s going on with me and my wife and I don’t think I ever was that even open with him.

But without me sharing what I felt comfortable with, he wouldn’t Pierce the veil. He wouldn’t let down his guard a little bit and say, here’s what I’m going through. And through these different understandings of how other people really are not what, how they project themselves. I feel I get a better understanding myself.

I get a better understanding of the world works. And if I really want to understand how things work. Yeah. That’s the way to do it. Otherwise we end up with this old NBC television view of what life is really like, right? The apprentice might’ve had huge ratings, but we all understand the apprentices, not business.

That television is not business. Instagram is not business, right? That’s the benefit of being vulnerable. I don’t say that everyone should do it, but I’m saying that if you could do it, even in your own one-on-one conversations with people, what you get back at you is an opening into what the person is really like.

And it’s, it’s incredibly helpful. It’s methodical. It’s not like here I am. I’m about to spill everything on the floor here. Just because someone told me that vulnerability is good, or because I expect something back and there’s a process, but it’s worth it because what you get back is a good payoff.

Wil: I feel like though it requires a ton of confidence to be vulnerable.

And that’s something that I’ve known you for a long time, and I always feel like a whimper on you rightly. And it’s a weird thing, man. It’s hard to explain because. You’ve always been so vulnerable. Like you just have this way, even when I listened to you, what was it like six months you interviewed with somebody who is like a psychologist or something.

And I reached out to you afterward and I think you said something like, Hey, I didn’t make enough money last year or something like that. And I’m thinking to myself, I never fucking say that right in, like, and you put it on a podcast. That’s just the most recent example I can think of. But every time we’ve got and together, like every time I’m move your house or we’re getting together for drinks or dinner or whatever.

Um, you just have this way of bearing your soul in a way. That’s so honest. And I think to myself, I don’t know if I’ll ever have the confidence to do it the way you do it, but do you see it as confidence?

Andrew: I do. I used to be really unconfident, really shy in conversations, and then I learned how to do it.

And that did give me confidence. It did give me the sense of. Ability to be in a room with other people. I couldn’t even talk to other people about anything other than whatever the task at hand was. And then when I learned it, I did feel like, all right, I can step outside my house and be okay. I can get into a party and be okay.

I can go to somebody’s house and be okay. It definitely gives me confidence. I’ll tell you where it came from. I, I had this period in my life where I’d sold that greeting card company that I ran. I had time to go and explore, and I said, I’m going to explore the non-work side of me and see what there is because I never was good at it.

And I started going to all these different events and I started to talk to people. Just as practice and I’d experiment. And I noticed something, something that now as an interviewer, I tell our team it’s called a shoved fact. I tell every producer works with me when you’re pre-interviewing a guests. Look for those shoved facts.

One of them came to me. The best example was I finished a Toastmasters club meeting where I was learning how to give a speech. And we ended up at somebody’s house. And we were sitting around talking and Anita talked about how her sister said my sister committed suicide. Then I get into my car and I came all the way to Los Angeles.

And then I didn’t know anyone here. And I realized everyone else around the circle was talking about how they didn’t know anyone when they came to LA, they totally missed that shoved fact where her sister committed suicide. And I realized, Oh, A lot of people do that. And a good conversational technique is to just say she committed suicide.

And if you give her room to talk about the thing that she’s desperate to talk about, that you shoved into the conversation that no one else asked her about, then you give her an opportunity to have a real conversation for the night. Instead of another LA is full of traffic. And a lot of us didn’t know people conversation.

Once I learned little things like that, it helped

Wil: it doesn’t take much either. Like, I think. It’s so rare that people are willing to actually listen, like you’ve developed this technique, but it’s also who you are in. True. You’re just such a good listener. I think like you do a good job of saying, Hey, I’ve been listening longer than everybody else has.

And I’m actually still paying attention to the words you actually used. And I have like an insightful question about it. And I think, you know, whenever we get together and talk, you’re such a good sounding board. Because I can tell you’re listening. I don’t think for a lot of folks that we interact with, it feels like they’re listening.

It feels like instead they just can’t wait to talk. And you know, we talked about this a little bit before we hit record. You were saying you were talking to some folks and like, it just doesn’t feel like you’re getting to know a real person. Yeah. It feels

Andrew: shallow. It’s useless. I was specifically thinking at the time about my wife has this friend who is so open with her and they’re such good friends.

When I get together with them. I have miserable time because the husband is giving me nothing. He’s telling me about the brand of shoes that he got. He’s telling me about the way that he’s setting up his home. There’s no. I failed this week, or I hate this job. There’s nothing that is at all showing a vulnerability or a real sense of who he is.

And it’s just deadening to me to have conversations with them.

Wil: I found that around the time that like you and I met, right. And it’s funny, cause you’re talking about when we were starting afford it. And we were getting the $20,000 checks, Elliot, my co-founder. And I just did an episode, the last episode talking about how that was the most hellacious.

Point of our life failed so miserably. And how, on the one hand we are showing the world how we were killing it, which is literally what you just referred to. And we’re going home and crying ourselves to sleep

Andrew: along because I do feel for a while there you were on top of the world. You came to Los Angeles.

Having made it in Ohio. Having had a few companies that worked out having profit, and you were saying, I made it, I know it. I’m going to now enter this other world of funding of going big. It wasn’t called a unicorn, but unicorn status is what you’re going for. And there was a period there. When you did feel like you re like you had it, you understood it and it wasn’t fake.

Was it? Yeah,

Wil: it was one of those things where the stock price starts going up and everybody just assumes it’s going to keep going up. It just didn’t. And it was the first time. And it’s this all ties together. It was the first time that I had ever very publicly failed at something. And so up until that point, you know, I was probably my earliest mid thirties up until that point, everything had always worked for me.

I don’t mean in life. I just mean in business. Right. I had a shitty life, but like a good business and I never had something to report that wasn’t numbers or up into the right. Like in, so I was the consummate chest pounder. In fact, I’m using those words specifically, and I think you could appreciate this because I’ll never forget, like sometime during this, this period, I ended up having this coffee with, uh, with Mark Schuster, right in Mark, who doesn’t mince words about anything literally sat across from me and was like, you’re just a fucking chest pounder.

Right. And I was like, Whoa, okay. Now, Mark, does it have a problem? He got us sponsored things. And I was like, what do you mean? He’s like, all you talk about is how great things are going and how much you’re killing it, et cetera. He’s like, it’s bullshit. Nobody wants to hear it. Right. And I was like, Whoa. But I remember around that time, I started to feel like there were two versions of me running around town.

There was the version that I needed to pretend existed because things were going up into the right. And then this other version of me that I never had to contend with before, which was starting to have a lot of failure. You know where our fundraise wasn’t going. Well, you know, things weren’t heading in the right direction.

And I had no ability. I had no tools to talk about it.

Andrew: And so what do you think you should have done? Do you think you should have been opened and said, this is not working afforded is failing. Yeah. In public to everyone. You think you should have done that?

Wil: Right? I should have said it to my close friends and I listen, man.

I didn’t think I

Andrew: was.

Wil: Lying. I didn’t have the tools of vulnerability if we’re really analyzing it a bit. There’s another piece there

Andrew: being

Wil: vulnerable. Wasn’t as popular back in 2007, 2008. It wasn’t that long ago, but the world has changed a lot, you know, since that time period, as far as, especially in the founder community, like you’ve got guys like Brad Feld that are talking about depression.

Right. That was still pretty quiet back then. And that wasn’t that long ago. That’s true. You know, I think emotionally there’s been a tectonic shift amongst us, right. Where we can do and say things that we wouldn’t have before founders can come forward and say,

Andrew: I hadn’t thought of it that way, but I think you’re right.

Wil: You know, you’ve been doing it all along the rest of us. We’ve been catching up along the way, and I’ve always wondered, curious your thoughts here. I’ve always wondered if. Your interview style, where your assumption that folks should be transparent. Was it harder back then than it is now? Like now I’m willing to be way more transparent than I used to be, but I’m wondering if that’s the case for everyone else.

Have you seen a change?

Andrew: I think people are always craving to be transparent about some things and hide others and it’s always different. So for example, you just happen to mention, I had a really shitty childhood, right? You brought that up. You might’ve been willing to talk about that before, right? Where other people would not at all want to go into what their childhood was like.

And what I wanted to do was say, okay, well, you don’t have to talk about everything. You don’t have to tell me what you’re thinking about when you’re in bed with your wife. You don’t have to tell me about, you. Don’t have to tell me about your illnesses, but you do seem comfortable talking about your childhood and that.

Is something that I’m interested in because I do notice that some of my anger from my childhood is what fires me up. And so I talked to you about that, and I think that we were all looking to have somebody talk to us about a few things. And very few of us were willing to have someone talk to us about everything.

And I said, that’s fine. Let’s just, I want to have as an hour with people anyway. Right. Or if we’re having drinks, we might have a couple of hours. Let’s just spend time talking about the things that you feel comfortable going into. I

Wil: get that. What’s been interesting though, is I found. That over time, the more vulnerable I get, the easier my career is in one of the things that you did really well from the get-go.

And I’m using you as kind of my gold standard here, because not everybody knows you and a lot of people have seen your interviews, but knowing you personally for a long time, and you’re really good at this, you have an ability to present a topic about how you feel about something or something that’s bothering you and go into what feels like infinite detail about it with no reservation.

About that vulnerability. Like, it’s just matter of fact, this is exactly what’s happening on that podcast that I was listening to his classic injury. You started talking about how you felt you didn’t make enough money last year, right? Actually, before I murdered this, do you remember what I’m talking

Andrew: about?

You’re talking about Sherry walling. She is the author, Zen founder, um, and wife of Rob walling. And there are a lot of little hooks. Why, where some people might’ve come into contact with her and the businesses that they’re a part of.

Wil: Do you remember what you said to her? About, Hey, I don’t feel like I performed enough last year.

I didn’t make enough money.

Andrew: I do remember saying that. Yeah,

Wil: not a lot of people. I would say that Andrew, you say you have no issue with it, but here’s,

Andrew: what’s awesome about that.

Wil: And what I think founders would really benefit from it gets it off your chest. The moment you’re vulnerable, you’re not defending anymore.

Right? Like I didn’t make enough money last year. That’s it? Right there. It is. Right. I don’t have to defend how much money I made. I’m already telling you it’s not enough.

Right. And I think about that. And I think about in the past few years, as I’ve personally learned to become more vulnerable, How much more effective it’s made me give you an example. Cause we were just talking about this a few months back. Uh, you know, there’s obviously a ton of civil unrest in the country.

You know, people were, were, were up in arms and I wanted to share with our staff, we’ve got about 200 people. I want to share with them how it was affecting me. Right. And some of the things that, some of the feelings that was springing up in me and I shared with my staff, something that I’ve really never shared publicly before.

Um, it’s already out there salt to explain it, but I had a really shitty childhood. You know, I grew up with a single mom. Uh, we were dead broke. We didn’t have enough money for food. I wasn’t very well cared for. We slept on the floor of a neighbor’s apartment for a year and a half. You know, I’d never knew where I was going to get food or when I’d see my mom again, that’s pretty personal.

I would have never. Brought that up publicly a year ago, two years ago. But once it’s out there, once I don’t have to defend or talk around it, it doesn’t bother me anymore. I think there’s a lot of power in that vulnerability.

Andrew: Yeah. That is true. This thing that’s been eating at you and is hiding and you’re working so hard to hide when it’s out there.

It is a relief.

Wil: Is there anything that’s taboo for you? I’m sure there are a bunch.

Andrew: Are there clear places where I feel that I’d want to have my own privacy with, it

Wil: would be a category I got I’ve said what’s the overstep, but I’m just saying like, you know, generally, like if I was saying child as a category, like, what are some areas you just don’t touch?

Andrew: You know, it’s fewer and fewer. I think that. Religious faith is one that I don’t feel comfortable, but I’ve been working on it in private conversations just to take away some of the. I don’t know some of the pressure I feel around it

Wil: and why that, and not something else,

Andrew: because it feels like it’s my own thing.

It’s something that I enjoy having privately and enjoy having this personal faith. And the only reason that I am now starting in private conversations to bring it up is because I realized my kids are six and four and they aren’t hearing me talk, talk about it. And if they don’t know that part of me and it’s important to me then.

It’s not something that they could have as an option for themselves. I might want them to follow my path, or I might want them to at least know it, but they don’t even know it because I’m not comfortable talking about it. So I’m getting more comfortable talking about it. What else? I tend not to go into specific numbers about how much I have in the bank, because I think that then it becomes, I still feel that my sense of self is tied up with my financial wellbeing.

I interviewed someone who, um, We’re not our bank accounts. And I told him maybe not, but before I go to sleep, after my kids are all wine exhausted me and I’ve worked really hard. And before I spent some time with Olivia. I always look at the portfolio to get a sense of where I am in the world. And you might say that nobody does that.

I look at it. I look at my photo, the photos of my kids for the day. And I look at that and sometimes I don’t look at the photos of the kids cause I just saw them go to bed.

Wil: Well, actually stick with that for a second. Cause I, you know, I, I think that’s a really powerful, personal thing because it’s, it’s something that we talk about our, our personal wealth, which is always lower than whatever anybody thinks it is.

Right. And we think about our professional wealth, which is like how well the company is doing. We’ve been running founder groups for a while now, and it’s a founders that get together and they talk very candidly about how things are going in. The temple with every new group looks exactly like this. And I think you’ll appreciate this first meeting.

Everyone is a little bit guarded. But then one person drops their guard a little bit in immediately. The guard of the whole group goes down a notch and then someone else takes a little bit further. For example, first pass every we’ll go around the room and they’ll say, Oh yeah, yo, here’s what I do. Here’s the market we’re after et cetera, you know, just typical startup stuff.

And then, uh, we’ll go around again. It’ll say like, what’s keeping you up at night and one person will say, I feel like a fraud. I don’t feel like I was meant to do this. And now I’ve taken on say investor money or I’ve made these commitments to people. And, um, I don’t understand what I’m doing. Just like a really hard right.

Turn around vulnerability and honesty. And here’s, what’s so awesome about it. And this is why I’m just so fascinated with this topic immediately. It gives everybody in the room permission to be at least as poorly off. Right. So in other words, at that very moment, as soon as that person says, you know, Hey, I feel like a fraud.

It’s okay. Now to feel like a fraud, everyone else in the room can feel like a fraud and just be okay with it.

Andrew: Yeah. And I’m so

Wil: fascinated by that dynamic because I feel like to what you’re saying, the more vulnerable and honest we become, the more it allows us to let other people in, because it lets their guard down, which allows us to learn more about them.

And. Some people like yourself, just do this naturally. Well, I’m learning it, you know, I’m 46 years old. I’m learning it way late in my career. Hopefully not too late. You know what I mean?

Andrew: I do, but I don’t think it’s nearly right. Natural with me. It’s very thought out. I’m not a natural conversationalist.

I’m not naturally good with people, but once I learned a few techniques, I loved it. I’m not the kind of person who was ever in flow naturally, but if I could use these techniques and then see them work, it feels great. And when they don’t work, I could go back and analyze it and then adjust it. And. It’s definitely thought through and my wife can see it having been with me for a long time.

So for example, the exam, the story that I told you earlier about Anita Toastmasters at the end of it, I could see, by the way, throughout the conversation, she loved that she finally got to talk about her sister at the end of it. She looked at me and she said, and was always sucking information from us.

And I felt like. Why are you doing this to me? Why are you saying that I’m now sucking information from you when you clearly brought it was a shell fact, and then you clearly enjoyed getting a chance to talk about your sister and why you came here. And then I realized later on it’s because I didn’t share anything.

And so then I went back and I tested sharing some of my stuff and I could see people’s eyes roll, because nobody cares about anyone else. They’re just looking for an opening to talk about themselves. So I said, you know what, from now on what I’ll do, is there a few things that I feel comfortable saying, I’ll stick it in a sentence or two, and then I’ll come back and ask them a question about themselves.

Boom, that opened people up because now they’re no longer feeling like I’m a vampire for their details. They’re feeling safe because I just revealed something and they feel grateful because I’m shutting up and giving them time to talk about it. And then I filed that away and I labeled it in my head. So that I can come back to conversations in the future and say, now I know how to bring this up at just the right amount, like an ingredient and have it work out.

And that’s, that’s where it feels really good for me.

Wil: Okay. So, I mean, you’ve had to do this with like thousands of guests, you know, particularly founders, what’s the technique. Are you sharing something about yourself in the interview and then, you know, using that as an open door, like, how does it work when you’re interacting, acting with other founders?

Andrew: It’s to be genuinely curious, genuinely curious, which means if I’m not interested in what they’re talking about, I get out of it. I went to work at Del Carnegie after I read, read the book, how to win friends and influence people. And I got really good at that technique. And one of the things that I love about Dale Carnegie is.

He says everyone has a passion, ask them about it. And I remember being on a train with my friend, Michael, and he was interested in comic books and I would just keep asking about the comic books he was collecting and the superheroes he cared about. This is frickin college and the guys like that deep into comic books, but he was off.

We almost missed our stop. I was dead. And by, because I don’t. Care about comics. I don’t care about superheroes. The only comics I have already, it was Archie comics because I love love, and I would love to see how does Archie get Veronica? You know, will he get Betty? Will they then all up? Right. So then I learned, you know what?

I can change the channel on people. I can find other things that they’re interested in that I’m curious about. And once you learn that you can dial into that. The thing that you’re really curious about that they’re passionate about. It’s great to be able to change the channel and then say, what else am I curious about?

And when they don’t go deep enough, you can push for a little bit more. Once you learn a couple of techniques and that’s the heart of it. Now, some people you just can’t do it with some people you just. There’s nothing you could do to get them to open up. And I have to learn to accept that, but when they are willing to, when they do want to, the conversation becomes more edifying than all of Google put together, because now you’re getting the exact thing that you’re curious about.

Right. They’re answered from the person who’s gone through it and can tell you, and there’s nothing else like that. No book will ever do that for me.

Wil: And so in the interviews, you know, do you find maybe pre-interview whatever that you do need to give some that you need to share a little bit in order to get some,

Andrew: maybe a tiny bit, I’ll give you an example of how a tiny bit can help Tim Sykes is one of the biggest show offs I ever met.

I love how good he is at it, but all he does is he loves to tell you how much he made in the stock market, how much his, his students who paid him money to learn from him and made in the stock market. And he’s good at telling it. So you sometimes don’t realize that all he’s doing is promoting, promoting, promoting.

I starting a conversation with him saying. I’ve got a podcast. I’m trying to get my podcast audience up a little higher than it is today. You’re really good at getting people to show up for your site on blogs, reading blogs, and reading a blog. You got Instagram, you suddenly went into Instagram. And how did it work for you?

What do you think I should do? And I like to hear what people did, because then you get more of the, the realistic stuff and less the theoretical stuff that should work. But by framing it before an interview by saying, this is what I’m trying to learn, I’m showing some vulnerability and by giving them some direction, Changing the dial to what I’d care about and away from what I don’t do you feel like

Wil: if you do show some vulnerability with him or anyone else not specific to him that it almost makes it feel like they have to give some back.

In other words, like that’s the way I always feel with you. Like when we sit down and you start talking about your personal life and things you’re dealing with, I’m like, shit, he’s sharing so much with me. Like, I feel like an asshole, but not nearly as transparent.

Andrew: It is kind of awkward not to. It’s true.

Yeah. But you can tell when people want to. And when they don’t, I think with me, that’s where experience comes in a sense of where people want to and where they don’t. But all right. So I have transcripts of my conversations. I think a lot of people don’t have the benefit that I have, which is not 2000 interviews, put 2000 interviews, largely transcribed.

So I can give you one of the techniques that I have, and you can see when it doesn’t work out. So one of my techniques is if I want to find out something that’s especially tough and I don’t want to put people on the spot, I’ll ask what a one of my interview coaches called a double barrel question. Is it awkward if I ask you, if you had sex with your wife?

Last night. Is it awkward if I ask you what your revenue was last year? Is it inappropriate for me to ask you right now? If it’s inappropriate, people will feel more comfortable ask answering the yes, it is inappropriate question. I can say this theoretically all freaking day long. You won’t believe it, but what’s the customer service, email, uh, software Zen.

Um, send us, send us. Thank you. The founder of Zendesk was on. You could go in the transcript. You can see, I asked him, is it inappropriate to ask you about something with his wife, with his marriage? His answer is yes. I’m not going to talk about it. And then we got to move on to the next and I’m not going to go cause it come on.

Why not? Why not? And then it becomes an awkward junkie, but if you phrase it that way, I don’t think he noticed that I was asking him two questions. I think he noticed the question that he felt more comfortable answering, which is, is it inappropriate? Actually Andrew, it’s not something I feel comfortable talking about.

Boom, Andrew moves onto the next thing. So if you have a couple of techniques like that, that gives some room for sensitivity. I think expected the people are open, but it doesn’t feel forced. I hope that’s true. And I’ve seen,

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Let’s return to the interview.

Wil: so here’s what I’ve found myself, which I think this is actually fairly interesting over the past few years, as I’ve gotten.

More vulnerable and I’ve been more confident in doing it. Like I said, I keep kind of referring back to the conversations you and I have had and how I felt on the other side. I’ve found that me being more vulnerable has made building relationships 10 X faster. And understanding better, faster.

Andrew: Yeah. Yeah.

Faster is the right word for it. Yeah.

Wil: I’ll give you an example with the folks that I work One of the things, if I were to go back 10, 20 years, I would have never shared anything personally. I mean, I was very cardboard at work. I just thought that wasn’t appropriate. And now the past few years, as I’ve shared more and more about myself, My team has come forward and they’re like, dude, like, thanks for sharing that.

Right? Like, it’s good to know that you have these feelings or you don’t, that you think like a parent does, or you think somebody that’s, you know, had a tough childhood. What have you, when I sent out that email about my childhood to our staff, I can’t tell you how many emails I got back and not just like a, Hey, thanks for sharing.

I’m talking like long, like life history, emails back from people talking about how they, they related. Yeah. I’ve never said anything in 28 years, that’s gotten anywhere nearly as an emotional response. And that wasn’t even my intent like that. I was talking about a totally different issue and it occurred to me what a miss it’s been by bottling all of this up.

And I talked to other founders, you know, the founder groups or, you know, just one-on-ones. And instead of going to my Marc Seuster chest pounding move, where I tell them how great everything is. I don’t wallow in my misery. Right. That’s not really what I’m about, but I started talking about stuff that that’s really bothering me and

Andrew: my conversations have gotten so much better.

Wil: You know, I think it’s powerful. I’m not using it as a technique either. I’m just realizing that, like, let me ask you this. Do you feel like when you’re vulnerable, it takes a weight off your shoulders. Cause I think I had a weight on my shoulders of defending it or keeping up an appearance.

Andrew: It does. Yeah.

Yeah. There’s a fear that someone’s going to know. Someone’s going to figure it out and then you’re always like, I’m not built to enjoy that. I think some people are built to enjoy the someone’s going to find out and I’m not going to let them. It’s just not me for me. It’s more like, Oh, someone’s going to find out now I’m now I’m scared that I’ve got this.

That’s that feels like a real vulnerability because then if they find out and they reveal it, then aha, where we’re really in trouble. I hate to admit it, but it is something that I’ve used as a technique. You said that you’re not, you didn’t do it as a technique. I’ll tell you what I have and give you a substantive benefit.

I hired a coach to help me with writing. She was really good. But she cost 500 bucks for, I think it was a half hour, 45 minute session. And I was getting a lot out of the conversation about my writing style, about how to improve and somewhere in there, I realized I’m never going to see you again. I’m never going to see you again.

We’re never going to talk again. And I realized she doesn’t care enough about me. To reach out if she has a shower thought that could be helpful for me. And I don’t feel like she cares enough about me for me to send a follow-up email saying, you know, I had this one question without saying, how much would you charge for the answer?

And I said, why? And I realized it’s because we had a very transactional relationship. As soon as we got on the call and it was $500. I knew that we were going to go right into this material because that’s what I was paying for it. And I didn’t want to waste time. And then I realized. If I would have wasted time, even if it’s two or three minutes by saying, by getting her to tell me what she was going through, she would have cared a lot more about me for asking her, for forgiving me the opportunity to talk about it.

And then she would have cared enough to follow up with me. And then how do I get people to do it? So here’s the technique that I’ve learned, especially now in COVID all my conversations are online. I can’t get into long conversations. As soon as someone picks up the call with me, instead of being me, which is I have to get to a point.

I will open up about something that happened. My four-year-old just strided it off to work it to school because he was it’s his four year old birthday started off to school. Like he was King of the mountain. Right. That is a little bit of personal stuff. I’m feeling really locked in because I can’t go out for a run outside because of all the smoke, my wife and I are now splitting up where we’re going to work, which is uncommitted.

I always look for one thing that just happens to be top of mind that I’m thinking about. And I allow myself to say it and to make sure that it doesn’t go much longer than that. I say, sure. I know we, I know we don’t have a lot of time together, but I had to get that off my chest. Where are you today?

How’s your family dealing with all this? It gives them room to talk about it. And then I write it down in my notes for like in my contacts. So that the next time we have a conversation I could follow up and say, Hey, you moved to Chicago. How’s the move with the in-laws going. And now we’ve got a little bit of a, of a follow-up, uh, opportunity.

That has changed conversations dramatically. Again, I don’t allow the conversation to go social more than three minutes and I am watching the clock, but I do insist on having that social part. And I think it’s incredibly helpful.

Wil: Do you care?

Andrew: I genuinely care or else I wouldn’t bring it up.

Wil: Okay. But you understand, right.

You know, you’re not just injured the sociopath that’s, you know, trying to, uh, Dr. Lecter about, out of an answer.

Andrew: Right, right. Yes. It’s not like I’m programming a computer. It’s what do I really care about them? I want to know where, where are they in the world? I want to know if I’m trying to figure it out.

Uh, should Olivia and I move out of San Francisco. Have you moved? How so? I do try to think about what’s the question that I would punch into a Google if I could. Sure. But I can’t let’s do that.

Wil: Who asks you good questions.

Andrew: Nobody it’s really painful. I even will go into therapy. And some of these freaking therapists pride themselves on I’m going to tell you like it is, I’m going to help you, like by giving you the straight, I don’t need your freaking straight answer.

Can somebody tap into the fact that I have some things that are on my mind and I don’t even know where they are and I, I need some help to tap into them. No, everyone feels like they have to just tell me. And every once in a while I’ll get angry at it at that. It’s really frustrating.

Wil: Can you build on that a little bit?

Andrew: Yes.

Wil: You’ve got a lot of people in your life though. I do. And I don’t want to pick on anybody. Is there anybody that’s particularly good at asking you good or hard questions or, you know, kind of opening up doors in a cathartic way? Um, at all,

Andrew: no puck, no evil. Olivia and I have known each other for a long time.

I get super open with her. I sound like I need her to ask me questions, but sometimes I will say something like. I had this dream last night that somebody was just revealed everything about me. And then they took away everything that I had and she say, that’s amazing. The dream last night too was awful.

Good. Wait, can we just pause for a second?

Wil: This

Andrew: is not an easy thing for me to tell you. I’m clearly admitting that there’s a problem here that I’m scared of something. What happened? Where do you think that comes from? Give me like a leading question that doesn’t say much

Wil: that’s painful.

Andrew: I would love to like, say Olivia, here’s my script of how I would operate.

Just take this. And like, what are the moments when I come in, just use that on me, use it. I wouldn’t feel bad. I wouldn’t feel like you’re a sociopath. I feel really relieved.

Wil: It kills me though. I mean, think of how many interactions you have now. Some of those are fundamentally transactional. If you’re doing interviews, you know, some people want to be on Mixergy and whatever, but it’s not like you’re sitting home alone. I can’t imagine how many people have sat across from you.

And I’d be remiss in saying when people sit across from you more and more, they’re valuing that time. You know, you’re a hard person to get time with. They know that you’ve got a body of work and you’ve, you’ve seen a lot. So they, they kind of value and want to use that time.

Andrew: I can’t quite

Wil: figure out why they wouldn’t want to dig deeper into what’s in your head.

It feels like it’s. Cause that’s all I can ever think of. Like whenever we get the chance to talk, you know, I was asking you a million questions because that

Andrew: way you really aren’t, it actually doesn’t come across just in the conversations we had in person. I’ll give you another specific one. We were talking about doing this interview.

I saw you going through my Twitter feed to just like prepare. I saw that you were doing the work you were. Putting yourself out there and asking. And I said, yes. And then I said, no, I can’t do it. You sent a message back about how much you understood. And I could tell that you understood what I was going through and saw it.

You’ve always been good that way. And there may be is one of my problems that I can say that I’ve got a lot of friends that I’m close with. But none that I’m super close with. None that it’s like an in-depth we’re getting together on a regular basis and allowing the depth of the conversation to build.

And that’s, that’s definitely on me for me to say, I wish that everyone had like the guidebook to talking that’s in my head and then they used it on me. That’s okay. Fine. Maybe that would be an ideal and that’s on them. Maybe if they’re not doing enough. Maybe, but it’s the thing that I have to take responsibility for is I’m not really good at following up and staying in depth with people.

I really like going deeper than most, but not as deep as some people have with certain con with certain people. And I just don’t have that,

Wil: you know, uh, less than when you were at my place in San Francisco, you left and I was talking to Sarah about it. Uh, we had those delicious burgers. I remember I was like, I wish Andrew and I were better friends.

Right. And this is kind of a common refrain for me. And I say that to say that just as a compliment to you, but like it’s Sarah and I were talking and I was like, why don’t we know each other better? Like, why aren’t we hanging out, you know, every Friday night, et cetera. And it’s one of those things where I don’t know.

That I can have a super in-depth conversation every time, maybe interest too intense for me. Right. You know, maybe every time we get together, like, you know, we just have this amazing conversation. What have you, but maybe I do need a fair amount of just dumb conversation about, you know, how Ohio state football is going.

And it can’t always be that intense, but I actually kind of don’t believe that that’s kind of what I said at the time. I think that certain folks that kind of take things. A step further with me asking me harder questions makes me uncomfortable. I don’t think I can stay that uncomfortable for that long.

And I think I pull back subconsciously. I think I’m, I’m not calling you because I’m kind of shit. Andrew’s going to grill me about something and he’s asking me good questions, but maybe that’s a little bit too much.

Andrew: It definitely is intense. I don’t think that I always do it. I’ll tell you that I do have another intensity that causes a problem.

I remember the last time before COVID hit that, I went out with a friend of mine. Johnny Chan, I think knew of a. Bar that had jazz, downstairs and good, good drinks. And I’m sure he just wanted us to get together and talk. And it was good for us to just get together and talk. And we didn’t go into deep stuff, even though we’ve, we’ve known each other for a long, long enough that we could.

But I couldn’t help, but make friends with the drummer and the guy who was sitting next to us who was causing trouble with the bar tender and this other person who came in with the, I don’t know, with the beautiful people. And then like, we were suddenly at this table with other people and he didn’t have any time with me.

And that’s another level of intensity that I think makes it hard. I can’t just sit still when we’re going out. I have to go and do something. I think about another friend of mine. Yeah. Who has one buddy that he’ll get together with on a weekly basis to do Skype, at least weekly Skype and editors have Bureau over Skype because they’ve been friends long enough.

And if they happen to be in a different city, my friend rich, we’ll just do it over Skype. I can’t just do that. It’s not enough. I always have to. When he and I last went out. I had to say, you know, has really fun time in San Francisco, people in the Castro, everyone else’s lame. We’re going to go to the Castro and we have to talk to everyone.

Who’s in like a gay couple, a lesbian couple, and we have, I have to get to know them all. And that is a problem that I have. I just need more.

Wil: Okay. So stick with that. I’ve been capable of smalltalk. It’s actually my fatal flaw. It doesn’t interest me whatsoever. Me too. Um, and by way of that, a lot of people say.

I feel like you’re interviewing me because I asked progressively harder questions of people. I’m not trying to do it. It’s not an interview technique. I’m actually just legitimately interested. Yeah. And I’m like, Oh my God. Well, if this is true, what about this? And if this is true, what about this? Do you feel like.

As you’ve gotten more and more good at what you do that you now interview people. You know what I’m saying? Like you’re subconsciously interviewed.

Andrew: I think you’re having the same problem that I had with Anita, where I was giving her so much room to talk about herself, that, and I’m following the train of thought that she wants to talk about.

So she’s happy to, most people are. I think at some point you’ve got to just go off on your own thing and take the mic away from them almost to the point where it’s like, Hey, wait, wait, what about me? I’m here. I think that, that helps. I had that same situation. Now, if you’re just grilling them, because all you’re trying to do is learn something and you need to get something out of them.

They’ll feel that if you’re doing it because you’re sensing that they have a path that they’re dying to go on and you want to go on it, then go down that path and then throw some of your own stuff in there. Olivia didn’t like we were at a dinner. She said, how did you have all these people talking? And so well, and everyone was just opening up.

And I said, she didn’t like the word that I used because I said, did you see how that one guy just kept going off? And. We didn’t, he wasn’t adding anything to the conversation. She said, yeah. I said, I was punishing him by not putting on the conversation and then giving him the mic. When I could see that he was going to go without being the douchebag promoter of himself, she doesn’t as like the hippie.

She doesn’t like that. I said punish and that kind of ruined the night conversation for me. That’s true. Take it, take the mic away and the person’s going to be starving for it. And then give them the opportunity again, to jump in. And they’ll be happy that you finally came back.

Wil: I hate to say this, but sometimes, you know, I’m at a dinner of other founders and there’s the chest pounder founder that, you know, essentially was me at some point.

How do you disarm that person? You know what I mean? Like how do you take your vulnerability? How do you basically show them that being the chest pounder isn’t going to work for them. Right. In other words with you, it’s not going to impress you. Right, because this happens with founders all the time.

Especially if you start to run in the founder circles and things like that, it happens when you talk to investors and investors kind of put on this air, like you have to impress me. Yeah. I’d love to be able to see a clever way to disarm people, which it kind of puts you in control. Not because it’s about control.

It’s about not being, you know, pushed over subjected to it.

Andrew: Yeah. I’ve seen some people do these cutting one liners that stop that. I don’t have that in me again, it’s like an acolyte of Dale Carnegie. I went to work for his company after I read the book, uh, how to win friends and influence people. It’s just not my nature.

My, yeah, it is. I’m going to read it to my kid. I started, it’s actually such good storytelling too, that I know it starts out with this guy who there’s a manhunt for a guy. So how could a, six-year-old not love a man on.

Wil: Or ever sleep again.

Andrew: Um, but I had that issue. We had several guests, uh, one of the things that my interview coach told me was he said, join the resistance.

I said, what do you mean? He goes, he says, my therapist. Would have men come into the office and they would sit there and the therapist would ask about what’s wrong, what’s going on? And the person would say, nothing’s wrong. Life is really good. And just sit. He said, for some reason, in couples, the man would put up the resistance and the wife would be open and.

He said, my therapist said that she decided to stop arguing and saying, you’re here. You obviously are paying money because there’s a problem. Your wife is telling you to come in here. You know, you need to be in here. There’s a problem. Be open with him. Instead of saying, you’re paying for this. Be open. She decided to join the resistance.

Join the resistance means ha. So you’re in a really good place in your life. Everything’s working out perfectly, right? So then the person would go, no, not perfectly. And jump in. I do the same thing with entrepreneurs. If somebody is so I’m on a roll about how great they are now, I don’t say, come on, something’s gotta be a problem.

Then I look like the jerk who’s prying for problems who can’t, who can’t accept that. They’re so strong. Instead I say. Everything must be great for you. It must be great to not have any, any problems in a world where we’re all struggling, right. It must be great that you are in a happy go lucky spot. And no, man, especially wants to be told that things are easy for them.

That’s when they come back and they’ll give you something, something which is all we’re looking for. The thing that they feel comfortable with.

Wil: And so as I’ve gotten to meet more founders, one of the things that I’ve just grown more and more attracted to is founders who can come out of the gate being vulnerable or in a very confident way.

Right. You know, how are things going? Yeah, not great, man. I mean, COVID hitting, we’re going to run out of money soon, you know, I’m, I really believe in the business, but we’re in a really tough spot. How do you argue with that? Right? How do you pick that apart? You know what I mean? Like, like basically

Andrew: you mean as a, as an approach,

Wil: right?

Exactly. You took down the wall. There’s there’s, there’s nothing to jump over. Right. And I think about how powerful of a technique that is now. I genuinely believe that the people that are telling me this one are telling him to, because they trust me. I spend a lot of time founder to founder and Anna, and I like to leave that open to them.

Hopefully they know I won’t judge, but the other is. I’ve historically done the opposite. I’ve been that interview candidate. Actually, I was, I was literally on your show. That’s what you told me at the top of this show you’re ending about. Right. Cause I thought that that’s what you wanted to hear. I thought you wanted to hear about how great things were going.

Not because I was hiding anything, but just, I thought. That’s what the show was about in the show being kind of a metaphor for, I thought that’s what conversations in intros were about. You know, you’re supposed to hear about how great things are going so that I leave you a positive impression. And so that the world knows that, that we’re okay.

And I think what I’ve learned, I’d be curious to hear your thoughts, but what I’ve learned is it leaves so much on the table. It’s like, yes, you’ve got my business card of how we’re doing. Right. You know, we’re, we’re killing it so to speak, but you know nothing about me and we formed no relationship. It feels like such a miss.

Now it feels the opposite of what I should be doing.

Andrew: I think that there’s a middle ground. I think that if I’ve seen some people who come across as just sad sacks, because they immediately come in with the thing that’s not going well. And they’re so needy that you can tell that now their whole future is resting on your shoulders.

And the conversation is way more important than I can have. And I think that a little bit of other stuff is helpful. And then. Being open without waiting too long so that it feels like you’re bottling it up and can’t wait to spill your guts out is better. I would suggest with few exceptions, start out with something else and then come in with this and do included, do include the vulnerability, do include the product.

That’s a problem because you’re almost tricked. All right. Here’s another one. One of the tricks that I not tricks. Here’s another one techniques that I had when I was dating. I would ask very personal questions. My wife will tell you, I asked her about her past sexual experiences. And now I feel weird about the way that I said that I asked her about it on the first date really quickly, because when you get old, I asked very personal questions because when you get open on per.

Stuff that’s personal. You almost feel like you’re further ahead in the relationship than you really have the right to be like Neil Strauss, the author of the book, the game. When I talked to him, I want to know about how to use stuff that he did for business reasons. One of the things that I learned from him was if he would go date.

And he would meet someone for the first time. He tried to move locations with them because if they move five locations, it almost tricks the brain to think we had five dates together. And when now we have a history together and our relationship is further advanced, right? If you start going into a personal spot with someone, it almost tricks the brain into thinking this person is at the same level as the guy that I’ve known for six months, because we are already where we are in the conversation as I’d be with someone who was six months along with me, I feel like those things are important and yeah.

I think that that’s what you’re getting at.

Wil: I do. I also think that there’s another aspect that I spend a lot of time with, which is tell me how you feel. See, there’s, there’s kind of two ways we can approach things. Here’s what I think. And here’s what I feel, right. How’s your business going? Here’s that’s what I think.

I think. Well, it’s going well, numbers are up into the right. How do you feel about your business? Right. That opens up a different conversation. And if you’re a founder listening to this, if you’ve ever talked to me, I’ve almost invariably asked you because I actually give a shit. How are you? Right. We can spend an entire actually, you know, I had a bunch of dinners last week with some different founders, all built massive businesses.

I don’t think we spent nine seconds talking about any of their businesses and we spent our four hours together. And it’s not that I don’t care about their businesses per se, but I actually care about them. And you know, I’m very passionate about the founder journey and kind of, you know, the things that deal with in every single time I asked these questions from founders, I get the same response.

You’re the first person that asked me that. I mean, think about that. Right? Think about your Mark Zuckerberg and every single time somebody sits across from you, they want to know something about Facebook, what you’re doing about Trump ads or whatever. How, how relieving would it be of just one, like, Hey Mark, how are you doing, man?

Right. Like, how are you holding up? You sleeping? Well, what’s stressing you out that has nothing to do with work right now. Right. You know, what a welcome break that would be. And I think for most founders, it’s almost like no one gives a shit about how they’re doing. It’s all about the company. And I think that gets amplified as we become more and more one with the, the, the persona that is our company.

Right? I mean, how many founders do you know, Andrew? Maybe their company is doing well, but they’re in shit health right now, or they’re depressed or, you know what I mean? Like that those two successful paths aren’t in unison, you know, and heaven forbid somebody asked them about that.

Andrew: The thing I think I realized that the other day I didn’t have the guts to ask.

And maybe it’s better that I didn’t, the person I was talking to was had clearly put on a ton of weight and you could see when it’s scared weight when it’s a stress weight. And I didn’t know how to bring that up. And I know that I did it at scotch night with a friend who was grateful to me years later for calling it out and letting him talk about it.

But I don’t know how to do it on a podcast where people are listening. And that’s where I feel like the personal side is so. It’s so important. It’s so interesting, but we don’t talk about that. And it’s, I don’t talk enough about it, even me,

Wil: different ways to get there too. I mean, you can basically talk about stress, you know, things that, that lead to that and, you know, see if that door is open, but, but it goes back to the fact that you would even care, right?

I mean, think about how many conversations you have in a day. Where people care about Mixergy, maybe getting on your show, you know, business transaction. Exactly. Like you just said a moment ago about the person that you paid $500 to, to get that writing advice. Right. And how little it takes to kind of break out of that, that consistent stream of people who don’t give a shit and just ask a very human question.

And how, how special that makes you.

Andrew: You just reminded me of something. I, there are a few people who, before an interview, before a meeting, they would ask me about running now who gives a rat’s ass about running? Most people, no. One’s looks out at the street. Seasoned runner goes, wow, that looks like fun. I want to do it.

You know, if you see someone play basketball, I’d like to, do you see them do like a, whatever on a skateboard. I want to do it. No. There are few people who would do that. And I felt like, wow, now I get like this glow of, I can’t wait to tell you about the run that I’m having or the frustration that I’m having.

And it’s like my own little hobby that I get. What you’re talking about, that tapping into the thing that’s about me. That’s not about work really does bring me to life because I’m not used to anyone caring about it or knowing it or taking the time. And that does actually, there are a few things like that.

That’s not the only,

Wil: you know, it also doesn’t have consequence. So intro, when you ask me about How’s it going? My answer has consequence. My answer has consequence. Like what if I say something’s bad? And Andrew repeats that. What if I say, um, Hey, we’re going to, we’re going to lose a deal, you know, Andrew.

And that somehow leads to us actually losing the, I mean, number of things.

Andrew: Yeah, yeah. Yeah. I like the phrase. It doesn’t have consequence. That’s really, if I say it’s nailed it.

Wil: Yeah. Andrew, how’s Mixergy going. That answer has consequence. Oh shit. It’s going terribly. You know, we might have to fire sale this thing, but if you say I had a shitty run who cares?


Andrew: Right, right.

Wil: And so, you know, maybe part of the discussion and kind of how we open up to each other is to open up the discussion with things that don’t have consequence. So we can talk about things we care about, especially when we’re talking to founders, because I think founders have this issue very acutely.

Andrew: Yeah. I think even in general, people have their topics that have consequence and topics that don’t, and it really is relieving to talk about the ones that don’t have consequence. And I could see that for some people talking about how their kids are, has too much consequence too much how their parents are, but work might feel a little bit different.

I get that. I’m gonna, I’m gonna think about that and find ways to incorporate that in my conversations.

Wil: Think about topics. I think about this a lot that you don’t have to defend. Yeah, right. Again, it goes hand in hand with consequence, but you know, I think as I’m talking to people, like when I interview people for the first time, you know, just, uh, employees, what have you, I try to look for things that they don’t have to defend, because I don’t know them well enough to know where I’m about to step on a landmine.

Andrew: So what’s a topic that people don’t have to defend

Wil: hobbies. Because the hobbies are generally like, Hey, what do you love doing? Like, I’ve become a wildly avid carpenter.

Andrew: Right? I know I saw your setup.

Wil: I it’s

Andrew: yourself right in the garage. Oh yeah. Yeah.

Wil: It’s I did the whole Tony stark Ironman thing. It’s bizarre, but I picked it up.

Thanks, man. I’ve picked it up out of nowhere, but. Here’s the thing you really can’t offend me with your questions in that one. Right? I kinda can’t get it wrong. You can say, Hey, that deck you built looks like shit, but short of that, right. You’re kind of in a safe space. And so I think when folks come to you and they’ve done a little bit of homework, find out that you’re an avid runner, they get to open up that discussion with you.

Take that to other things, man. Think of like how important it is to open up rapport with, uh, like a, a VC, right? Imagine if you’re the BC and you’re doing like eight meetings a day and somebody finally comes to you, it opens up about something personal. Right. All of a sudden you’re like, fuck, finally, you know, like we’re talking about something other than our portfolio.

Andrew: Yeah. I think you kind of have to break

Wil: that seal.

Andrew: I wonder also if there are things, especially if, if I’m talking about one of my. Wife’s friend’s husband, maybe a lot of the stuff that’s personal in their lives has consequence with his wife. And there’s why he’s not being open about it. Maybe he would ordinarily be open, but if he reveals a problem that his wife doesn’t want to share with my wife and then it gets to my wife, then there’s a consequence.

And so a hundred percent by going into vulnerable stuff about him, I’m going into vulnerable stuff that she may not want to talk about her. And so he might be putting up a front, not because he is. A douchebag, but because he is being respectful of his wife’s privacy and his wife’s relationship, and I should look for things that he had no consequence, what’s his carpentry that he can’t wait to talk about.

What’s his thing that he can go off about that he cares about deeply, but has nothing to do with anyone, but him. That’s what I should be looking for. So now I can never tell the story of how this turned out, because he would know that I said that. I said that he was the guy who was a

Wil: douchebag.

Hey, so let me ask you this. You know, we’ve been talking about vulnerability. Let’s, let’s kind of wrap up with a bit of a counter question. What is it not appropriate to be vulnerable? Where does it backfired on you?

Andrew: I think it backfires and from fires all the time. I think I have to go in knowing that it’s going to be, that it’s going to be a problem that we do all still like to believe in heroes who are invincible.

And if that is the way you’re going and you can pull that off. You’re great. Otherwise you have to know that once you admit that you have one, Superman says that kryptonite, or once we know the kryptonite is his vulnerability, it’s going to be used at some point. And I think we just have to be okay with that, that.

It will at some point come back and cause a problem and you have to go into it accepting it. It’s like someone who trades stocks, but is not willing to have a down day or a down stock. They can never stay in the stock market. You can’t stay in the market of ideas and conversations and not expect that at some point it will backfire and you’re still going to be okay.


Wil: That’s the way I feel when you interview me, I feel like if I tell you that my company is doing poorly. Back to consequence that it’s, um, it’s got an effect on my customers. It’s got to affect my investors by employees, the media prudish, everyone that can be connected to the company becomes a consequence or a victim to that question.

I feel like it’s not okay to share because I put everyone at risk, unless I just say all rosy things. And yet I’m really conflicted because I don’t want to misrepresent it. I don’t want to not lie to you, but you don’t. I want to tell you how things are going, but I don’t feel like it’s appropriate. Does that make sense?

Andrew: Yeah. And I think we all have to get comfortable saying where our line is. We all have to be comfortable saying that is not a topic I feel comfortable talking about. That is I’m just not ready to talk about that. And most people will accept that if they don’t, you can move out of the conversation or you could just put up more blocks, but I think we have to be comfortable with it, or else we’re going to go to bed, sleeping and waking up worried about the stuff that we said, and we’re not going to have personal conversations, unless we could also say here’s where our limit is.

Here’s where I just don’t feel comfortable. And, and. There are ways to transition a conversation away and we should be comfortable doing that.

Wil: Do you feel like there’s something in your life that you wish you could take back? You’ve overshared too much. Historically

Andrew: inevitable. When we do interviews, I will get calls from people, texts from people who I interview saying, can you edit this thing out?

And inevitably it is the best part of the interview that they want edited out. And. I have to spend a lot of my time telling guests, no, I don’t do any editing. You sign this agreement. You also recorded yourself saying that you’re okay with it and all that. And still, when I was interviewed for my own podcast, I woke up in the middle of the night.

I use Siri to dictate a message to Ari, our producer, to say, please don’t publish the interview. And then when we got on our Tuesday weekly call with the team and. I brought it up. She said, yeah, I, she laughed because she recognized that I was doing what other people do. And then she also recognized that it wouldn’t be a big deal.

I would love to add color to the story with details. I know details. Add color. I don’t even remember what it was that I said in that interview that I texted her, emailed her in the middle of the night to ask her to edit out. That’s how insignificant it is. But it’s still worried me at the time. So yes, I do worry about it.

And within a day I don’t and within a year, I can’t remember it and I wouldn’t have a list of things because they just are insignificant

Wil: I’ve thought every single day, since I sent that email out to our staff about my childhood in 10% of me wants to control Z at every day. And I’m not sure why, you know, it’s interesting.

I’m not really like, embarrassed about it. Um, you know, when my fault, that’s just kinda how I grew up. It wasn’t like, like I made a mistake somewhere, so I don’t have to defend it either. And yet I feel better for sharing. Sure. For sure. I’ve shared it, but I don’t feel, I don’t feel great about it. Do you know what I mean?

Like, I feel like this level of transparency is, is. Definite a tool that’s super powerful, but I still feel like I’m trying to understand where that line is. Right? Like, even with you ensure like, I want you to be transparent, but I’m not sure that I want to hear everything about you. Right. And so when you’re saying, Hey, you know, I don’t want to talk about how much money I have.

I don’t want to hear about how much money you have. I mean, actually don’t want to know. Because, you know, it’s funny thing about wealth. I never, I’ve never, ever shared how much money I have with anybody in my entire life. I’m not even sure. My wife knows here’s why a good friend of mine told me a long time ago, and I’ll never forget this.

And it’s best advice I ever took. He said, never tell people how much money you have. There’s only two outcomes that will come with it. Outcome number one is they’ll size you up and try to use that as either he didn’t make enough or he made, uh, made too much, et cetera. They’ll basically judge you for it.

No matter what the number is, there’s going to be a judgment coming with it. And number two, they’re going to try to find a way to extract it from you, right? In one way, shape or form, neither of which benefits you whatsoever. Right? And so unless you’re looking to have a judgment made on you, or you’re intense about parting with your money, it’s not worth sharing.

And ever since then, and that advice was given to me 24 years ago. Ever since then, there’ve been people who’ve tried to add up my bank account and certainly countless more than trying to extract from my bank account. It occurred to me every time I hear somebody else saying this is how much money I’ve made, or this is what I’ve done.

What a colossal mistake was. That’s one of the few things that I’ve never shared that I’ve never regretted, you know, not sure

Andrew: I’m with you. I think that you’re right in that analysis. I also find that there’s some people who I’m sure there’s some people who do benefit from it. I don’t think it’s common enough.

And I think your point of view is I know that’s the one that I subscribe to. And I, I think we should just feel comfortable saying that’s the line that I don’t feel comfortable going into and also comfortable transitioning the conversation away because otherwise you’re leaving the person with this thing that they’re with this puzzle that they have to figure out.

Wil: Yeah, I agree. It’s also, sometimes we’re saying there, I don’t really want to share it. And honestly, there’s, there’s not much to it to even be worth sharing. You know, that way you basically say the treasure chest is empty. So you kind of dismiss that last, last question for you. If you’re thinking like long and hard about.

Where transparency has benefited you the most. Uh, and where it’s cost you the most. How do you think about that? And I say this injury because of all the people I know you’re the best at it. It’s almost like asking Dale Carnegie, you know, like you’re the best sales person in the world, you know, where’s it benefited you, et cetera.

You’re so good at this technique of using transparency. If you look back and think of all the places where it’s gifted you some special opportunity, what does that look like? And where does it cost you? Because you’re, you’re also, you don’t just say it, you express it as well.

Andrew: The places where it’s gotten me, the best benefit is.

That other people were then equally benefit equally open with me and it created good longterm friendships. I mean, ours is an example of that. And with the audience, it’s given them an understanding of who I was. And so they could connect with me. I remember when Steve jobs pick somebody to write his autobiography or his biography, the authorized biography.

The writer got little things wrong, like the material, the type of metal that Steve jobs used in the iPhone, which as in technical point of view, you should get that right. But Steve jobs knew that he wasn’t going to get everything right. About the technical side of the business when he did get was. A little bit of the flaws of the person.

And we connect with technology. That’s flawless. If a website takes more than two seconds to load, we want to move on. It has to be so flawlessly fast that it’s instantaneous, but we connect with people through the flaws, through those little bits of friction that allow us to hold onto who they are and remember them.

And that’s. The book was full of it. Stories like the problems that he had with his daughter. Lee said that he addressed stories like how we ordered several cups of orange juice and parked in the, um, in the handicapped spot. It wasn’t a SU huge secret and nobody was shocked by it. Those little things make, can seem more human and make us connect with them.

So there’s an absolute upside in that. Anyone who knows in likes me it’s because they’ve seen. Some vulnerability that they could hold onto, that they could connect with

a wrap for this episode of

Wil: the startup therapy podcast.

Andrew: This is Ryan written on behalf of my partner will Schroeder and all the family thanking you for joining us. And we hope you’ll continue to join us.

Wil: Be sure to subscribe,

Andrew: rate, and comment on iTunes

Wil: or wherever you love to listen to up therapy,

Andrew: you can find all of our episodes at

If you like this interview, you should go check out startup therapy. That’s the podcast that this was a part of. So again, in whatever podcast app, you’re listening to me on look for startup therapy. It’s Willis Schroders podcast from

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