What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a lot of money in the process.
And on this show, I sit down with these IndieHackers to discuss the ideas, the opportunities, and
the strategies they're taking advantage of, so the rest of us can do the same.
I was immediately captivated because you started the book with this story.
And the story kind of sells you on the entire purpose of the book.
It's like a really smart way to start the book.
And you talk about how you had this opportunity to meet kind of like a big shot investor,
financial professional, like this was your chance to essentially learn how to be successful
from this guy.
And you asked him all these questions, and you ended up getting all of these like very
generic responses back, like good things come to those who wait, that kind of like a dribble.
And then your time was up, and he left the room, and you're like, I wasted my shot.
How could I have talked to this person better?
And it makes me think of this quote that luck is where preparation meets opportunity.
That was an opportunity, but you weren't prepared to know how to talk to somebody such that
you learn the uniquely valuable stuff that they have to offer.
And that's a really cool topic.
That's what your entire book is about.
It's called Stop Asking Questions.
I should introduce you to Andrew Warner, the host of the Mixergy podcast, one of the only
started podcasts that I have listened to extensively.
And I think the first one, I think I was listening to you back in college in like 2009.
Is that right?
Is that old?
Yeah.
It's been around for a long time.
Yeah.
It's been around for a ton of time.
It's inspired, I think, probably millions of people.
Welcome to the Indie Actors podcast, Andrew.
Thanks for having me on.
It's been a long time in the making.
Like you and I have like hung out in person more than a few times.
You know what?
I liked you so much when we hung out in person.
I like everybody, but I liked you even more.
And then I walked away and I told my wife and she said, so who'd you meet?
And I showed her a photo and she goes, oh yeah, looks like such a good guy.
I like him.
And then actually she said something like about how good you look.
But I could also say that it was, there's something about you that makes you just a
likable person and someone who people feel liked by.
And I realized, oh, it wasn't just me.
It's just who Cortland is.
And I think you naturally are like that.
And I wonder actually, here's what I wondered walking away from it.
Is it because you did so well with Stripe and life is like organized and you got a good
mission here or is it that you're naturally like that?
Were you like that in those years when you were suffering, when the business wasn't working
well?
Yeah, I don't know if I would say I'm a naturally likable person.
I think, I think that I am very, I'm a very agreeable person.
I am very agreeable to people who I don't know very well and I think I'm overly disagreeable
to people who I do know very well.
So I think I created a really good first impression.
Oh, you'd be a horrible boyfriend is what you mean, but a great, let's get together
for drinks.
Great.
All right.
But I had the same impression of you because I listened to your podcast so much and like,
I don't know, you're just like an extremely high energy person and I love people who have
a lot of energy and you're very interesting.
Like, you don't want to talk about boring shit and I love that too.
Like life is too short to talk about the weather every conversation.
Oh, we had such great, now think about, I won't reveal all this stuff that we talked
about because it was so personal, but it was like, if I just say that it was each other's
sex lives, it feels like it's nothing but salacious gossip.
Like I can't believe we talked about it, but I mean, in a super deep level about the challenges,
about thinking differently, about understanding who we are, about having different options.
And I'm not saying I'm like in an open relationship and I finally came out to you.
I'm just saying that within a marriage that I've got with Olivia, within your relationships
in the past, there are things that we learn about ourselves that I don't think we can
talk about publicly here because we don't know who's listening, because it's inappropriate
for all these reasons.
But when we got together, first time we meet each other, we get deep like that.
It's not an exaggeration to say it helped me with my relationship with Olivia.
It made me feel closer to you that you remember in COVID when I was struggling, I'll say this,
I was looking for E because therapy was not working for us.
We loved each other.
We loved spending time together, but something was off.
And I was able to talk to you about wanting to get E for me and my wife.
And you know, we have a professional relationship.
And for me to feel that connected to you that I could talk through and for you to intuit
what was going on in our relationship through that, I think that's a gift.
And so when we talk about how do you have meaningful relationships, it's to have that
to just talk about your work.
And boy, we got really interesting things about what happened to you previously, but
also to get personal about my life, about your life, it helps.
We got super personal.
And I think a lot of that is just having an environment that promotes fearlessness, right?
The fact that like we weren't on the air, it was just you and I at a bar, no one else
is there.
You're comfortable.
I'm comfortable.
There's nothing to be afraid of.
So like, why don't we dive deep and talk about those things?
Because how do you bring it up?
I've had, I have had relationships with people in the past before I learned how to have conversations
where I didn't know how to bring it up, where it would be superficial, not because no one
was willing to do it, but because to go from how you do and tell me about who you're sleeping
with and what's the problem at work is an awkward thing to do.
Even how you're doing, here's my problem.
Can you help me is a needy thing to do.
The transition from regular conversation to super deep, let's actually touch on the things
that matter is really challenging.
Yeah.
And I think you're the expert at this.
Like I've been interviewing people for what, four or five years.
I don't consider myself to be a master of the craft.
I don't study it that much.
I just get on here and click record and hope to have good conversations.
And I think that my agreeable nature means I try to, I try to sort of naturally meet
people on their wavelength, which means that if I meet somebody who's closed off, like
we have a closed off conversation and I meet somebody who's willing to talk about things,
like I'll go as far as they want to go.
Whereas you're sort of the opposite.
I feel like you can get almost anybody to open up.
You can learn anything valuable from almost anybody that you talk to you because you're
very deliberate in practice and how you do these things.
And you're so practiced at it that you don't even seem practiced at it.
You just seem like a natural at it.
And I love it.
Yes.
I was like, how is your, how is Andrew the exact same person on the air that he is in
real life?
I was shocked by it because I thought you're like a radio personality, but in reality,
like that's who you are.
You've become this person who has great conversations.
And it took me a long time.
Like we were talking before I had had an opportunity to meet Ace Greenberg.
The guy was an advisor to billionaires.
He was, I remember watching A&E biography about some billionaire and he was on being
interviewed as the advisor to that person.
I finally had an opportunity to talk to him.
I didn't know how to even ask him about anything related to business.
And he wanted me to ask him that he craved that, but how do you do it and how do you
get into something meaningful?
It's a challenge.
It took me a long time to learn it.
I like that you said that it wasn't natural.
I hate when people say I'm a natural at it because they really don't understand the painful
years of having, you know, jobs where I couldn't talk to my bosses properly.
I could talk enough about the job, but not beyond it.
You couldn't get that tightness that other people had.
I remember having deep trouble having just personal conversation with people.
Yeah.
Well, the point is you eventually learn how to do this stuff, right?
Like you go through these years of struggle and to anybody listening, like anybody who
joins your podcast as a listener today, they're going to think you're a natural because they
don't see, you know, the 90% of the iceberg that's under the surface.
They don't see the gears of hard work that went into it.
But if they read your book, it's called stop asking questions.
I don't think it's out yet.
I got a draft of it in PDF form.
Have you published this yet?
No, it's coming out in October.
We're just weeks away, but people can go and get the early copies of it and read some of
these techniques at stop asking questions.co.
If somebody reads your book, it becomes clear that there are tactics behind this.
There are thoughts like this is not a natural thing.
This is something that you've actually puzzled through.
And there are people, of course, out there who like do do some of this stuff naturally.
But I wonder, you know, like where even the best places to start here, you know, maybe
if we rethink this, this conversation that you had with this financial advisor, forget
his name, but this guy's advising billionaires.
He's a badass.
Young Andrew went in there, didn't know what to do, didn't know how to get useful information
out of him.
Knowing what you know now, how might you approach that situation and learn all you can from
like somebody like that who's got a lot to offer, you know, one of the best things to
do is to get clear on what you want to know and why.
And if you can't find a way to ask it, at least say that's what I'm trying to understand
to have at least gone in there.
And instead of coming up with the perfect question, starting with the reason to be there
and saying, you know, Ace, can I call you Ace?
Everyone else seems to goes, yes, say, I watched the movie Wall Street.
I admire people who built this city and people like you who are doing well.
I'm trying to find my way into this space and not just be a bit player in this big giant
machine of Wall Street.
I read everything about you identify with your climb from nothing.
I work for you.
What do you think the next step I should take and what do you think I should be thinking
of working here for you and working on Wall Street in general?
I came here to try to tap into that.
Instead of I came here to learn from you in general, you know, a little bit more specific
goal is really helpful.
Yeah, I love that.
I love that because number one, you're sort of aligning your goals, like he's not going
to want to disappoint you.
If you're looking up to a person like that and telling them like, hey, I have these very
specific lofty goals and I think you're the person who can help me, he's going to want
to do really well and you've made that super clear upfront.
And the other thing I like about it is basically the fact that like not everybody has something
unique they can teach you, you know, like when you come in this show, like I have a
list of very specific things that I think I can uniquely learn from you and if I don't
have that list, which is what you're advocating, then how on earth do I know what to ask you
about?
Like how on earth can I possibly learn from you if I don't know what it is I want to learn
from you?
Like how do you sort of fish around and you know, hope that you say something interesting
and I follow that thread and sometimes that's fine, but not if you have a very limited amount
of time with a very rare opportunity that you really want to maximize.
The more specific, the better.
And so like you could take a look at my interview with Cameron Harold.
He's the guy who used to be the COO of 1-800-GOT-JUNK.
I threw away all my structure, all of the stuff that I had learned over the years.
But with Cameron, I just said, I'm burning myself out, I need to figure out how to hire
somebody else to come in here and help me.
I'm trying to understand that.
And then we kind of puzzled through it and understood where I was and got advice from
him and it was incredibly useful interview for me, but also for the audience.
And in there you can see just being clear about what you're trying to understand as
specifically as possible.
Not how does one, not how does someone hire a COO, not how a COO is created, but here's
the thing.
It requires a level of vulnerability that's really hard.
And frankly, even for me, it's hard to bring that up and say, I need this help.
And that's another thing I think that's useful in conversation.
To have that level of vulnerability to say what you're looking for.
And then on the other side, we should also talk about with Ace Greenberg or someone else,
at some point you want to go beyond the utility of the conversation to the depth of the person.
And so you need ways to go from the business utility to the personal get to know you.
And once you do that, you again have to go vulnerable because you would not, Cortland,
have told me about the problem you had with the girlfriend that you had back when you
were in San Francisco.
If it was just me grilling you about the girlfriend and not feeling a sense of openness and telling
you about my wife and me and my past relationships.
And so again, it's a clarity, it's a vulnerability, and it's also business and then going into
personal with everybody, even Ace Greenberg, who I worked for, who was like a buttoned
up guy who I don't think ever went to sleep without a certain or shooting tie on.
Yeah, there's this concept of logos and pathos and ethos, essentially logos is logic, right?
That's let me get to the bottom of your issue.
Let me ask you for the tactics.
Let me ask you for the advice.
Let me ask you what's going on in your life.
But then there's like the emotions that's pathos, right?
If you don't connect with people on an emotional level, you're really not going to get everything
you can get out of them.
And then there's ethos, which is kind of like this character and credibility situation.
This is like trust.
And that's what you're talking about, which is like, hey, I'm not just going to ask you
for your stuff.
I'm going to share with you what I'm going through.
I'm going to build a layer of trust so that you don't have to come into this conversation
with fear and resistance.
I'm somebody that you actually want to talk to.
And I think it's really easy, especially for certain types of people like your nerd like
me to just go straight into the logos.
Like, let's just get the facts out of the way.
And I could take that with me into, you know, a fight with a partner or an interview or
a conversation with a stranger on the street.
But like, that's no way to build connection with somebody and actually have a good conversation.
So then I go deeper in the book about how to do it.
But the question always that I wanted to understand was how do people who are as uptight as I
am, and I clearly would see people who are uptight, get close friendships with people
on a non uptight, non business way.
And there are a few things to do.
One of them is to look for those moments when people happen to reveal a little bit about
their personal lives.
Like if you happen to say, my girlfriend and I had some trouble and, you know, the website
helped or whatever.
Look for those moments.
I call them shoved facts where you don't have to tell me about your girlfriend, but you
shove that fact in that you have a girlfriend.
You don't have to tell me about your mom, but you shove the fact in about your mom while
you're telling me the thing you have to tell me.
If we pay attention to it, we will see that people are yearning to talk about personal
things.
They're eager to tell you about things that are not business because that's what's on
their mind.
And if we pick up on it and without fear, and there is a fear of awkwardness, a fear
of intruding in their personal lives, it's like somebody invites you into their home
office and you happen to go to their bathroom and you happen to, you know, see the cream
that they have on the medicine cabinet.
There's a sense of invasive, but not we have to feel comfortable not seeing it as an invasion
of privacy, but seeing it as a connection with the other person.
So when they say something about the girlfriend to say, are you still with her to say something
about it, to pick up and go with it.
I love it.
I love the idea that it's called a shoved fact because it's like they're shoving this
into the conversation and you don't have to feel bad about taking that threat and running
with it because it's kind of an invitation for you to do so.
Like they didn't have to bring this up, right?
You didn't have to bring up your relationship with your wife and therapy, et cetera.
I didn't have to bring up, you know, my approach to open relationships, et cetera.
But the fact that I bring it up as you're saying means that probably I do want to talk
about it.
And that's far more interesting than talking about, you know, whatever else you talk to
a podcaster about, you know, how do you record your interviews, how do you edit it, et cetera.
And so why not tug on that thread if you see it in front of you.
At the same time, there's something that's a little bit, it's sort of like leaving things
to chance, right?
Like not everybody is going to shove interesting facts into the conversation.
Not everybody is going to sort of have something that they want to talk about.
And if you come into one of these like rare opportunities to talk to somebody very cool
and somebody very interesting and potentially someone you can learn from, you might have
your own list of things that you want to learn.
Like I mentioned earlier, like I have a bunch of, I have a bunch of different things that
I want to learn from you in particular, Andrew.
And it's not guaranteed that you're going to shove a fact in there that happens to coincide
with what I want to learn.
How do you, in an interview and in a conversation, I guess gracefully guide people to tell you
and teach you the things that you want to learn from them.
One of them is to just ask the thing that's on your mind.
I have personally brought up issues with people and I was thinking about just to get answers
from someone else.
And then the whole dinner conversation ends up being about this one issue, you know, stuff
comes up.
And so you want to, you want to say, this is what I'm thinking about.
What do you do about that?
Or how would you think about it?
Another way to do it is to ask, is it inappropriate?
I hate that I call this out because once you see it, you're going to see it in conversation
with me.
But if you and I were just talking and I was trying to get a sense of like, what's your
dating life like?
And you gave me nothing, you showed me that apartment, I might go, that's a beautiful
apartment.
Is it inappropriate to ask if you've like brought dates home yet to this place?
And now we're transitioning to that.
And the thing that I like about the isn't inappropriate to formula is I'm asking, is
it inappropriate to ask this other question, which is another question.
So I've asked you two questions.
You could take the easy way out and answer the one that you want to.
And if the one you want to answer is it's inappropriate to ask me about girls in my
house, you're going to do it.
And you can see it.
One of the beauties about having done these conversations, I call them these interviews
have been conversations for over 10 years, over 2000 of them is I've had them transcribed.
You can see it.
You can see the founder of Zendesk.
I asked him, isn't it appropriate?
And then I asked him about his wife and he says, yes, it's inappropriate.
So I back away.
And then I share a little something about myself and then we move on with the conversation.
So people will feel natural and you can see it in the evidence that they will feel saying,
yeah, it isn't appropriate.
But if it's not, now you've gotten an entry point into their lives.
I love that for, I'm just going to like analyze every tactic you give and your book is full
of these tactics.
There's literally like a list of like dozens of conversational tactics that I think you
can practice and then become a natural at like you are.
But I love this particular tactic because for all the reasons you listed, but also because
it makes it easier for you to ask scary questions as a conversationalist.
If you know that you can ask this question, as long as you preface it with isn't inappropriate,
you're going to be more likely to ask that question.
And also it's back to this concept of ethos of building trust.
If you ask somebody, if this is inappropriate before you ask the question, they know that
you care.
They know that you're not just some raging bull who doesn't give a shit.
He's just going to try to get the answer and who doesn't worry about whether this person
feels comfortable sharing.
You're clearly telling them, hey, I do care about whether you feel comfortable and I'm
on your side.
I'm not trying to push you to get answers without caring how you feel.
And that might make somebody open up to you who previously didn't trust you.
I think it's also important to say that people can tell whether you're, whether you're coming
from a genuine place or if you're hunting for information to use against them or to
entertain yourself.
They could see all that I mentioned in the book that there's a question that I asked
Jason Fried and I could see in the video recording of my conversation with him, this is the founder
of Basecamp.
He looks up at me, it's a micro gesture to see, can I trust him before he continues?
And we do that a lot and we've gotten really good at doing it.
We're not so great that we can beat the best BS artists on the planet, right?
If you get somebody who's an absolute swindler, a Bernie Madoff, I'm probably not, I'm definitely
not going to know that they're Bernie Madoff.
But day to day life, we're not Bernie Madoff's super experienced at hiding billions of dollars
in losses and Ponzi schemes and all that.
We're regular people and we don't have the skills and the desire to hide all of our gestures
and people can pick up on those micro gestures and see this is a person who really cares.
This is a person who is trying to understand me, trying to figure something out.
And that's important that if you come from a genuine place, understand people will see
that.
Another one of the tactics you talk about in the book that's really interesting to me
is you call it stop asking questions.
That's literally the idea of the tactic, which is super interesting for advice to give people
conversations where they're trying to learn or advice to give people on interviews where
they're trying to basically extract information from someone.
Like I'm talking to you, I'm interviewing right now.
The most natural thing I can do is ask questions.
So why is this an important tactic for essentially interviewing people and learning from people
you talk to?
I realized that it was important to stop asking questions when Olivia invited me to this friend
of hers house in Southern California and we're talking about one of these most beautiful
LA houses that you've ever seen.
I'm supposed to talk to the woman's husband while my wife talks to the woman and so we
have this conversation.
I look at his pool, we overlook the pool and we see the freaking ocean.
It's gorgeous.
And I'm basically finding out how did you get so rich?
And as I'm asking him that, we're talking about how he got into apps back when Blackberry
had apps and then he transitioned into iPhone apps and I'm asking him, so how'd you know
that apps were going to work?
How much money was there to be made in Blackberry days?
There's a lot, apparently.
Enterprise would buy these apps and he was amazing.
I had no idea.
But we started out as friends just talking over a beer and I could see in his eyes that
it was changing.
The relationship was not going to be a friendly one where I could hang out with him again.
And I knew it for sure when he said, go get me a beer before I answer the next one.
And I could tell the relationship had changed from two friends who happen to know each other
because their wives were friends to me being like this needy student who was trying to
learn from the master and he was going to see me when he had time to give back, quote
unquote.
And I took that back to my interviews and I realized the same thing happens in interviews.
You ask question after question after question.
People don't see you as a peer.
They don't see you as a guide.
They don't see you as a needy student, someone who's going to pester them with questions.
I used to hear Howard Stern guide people with statements, say, tell me about, go ahead,
do this, tell me that.
You hear Kara Swisher from the New York Times, she says, tell me a little bit about, that's
one of her formulations.
I don't know if she realizes that she always says, tell me a little bit about or talk a
little bit about, but she tells them what she wants.
And I realized they're not being jerks.
They're actually being smart about conversations.
They're rephrasing some of their questions as statements to guide the person and not
come across as needy.
And so I say in conversation, if you're going to talk to people, talk to people and sprinkle
in some statements and often even questions that are rephrased as questions.
So for example, instead of saying, how did you get started in business?
You can say, tell me how you got started in business.
Tell me where you got your idea.
Tell me about the time you burned out.
Now if you do only that, it's tiring for the other person to be push, push, push.
But if you add it in from time to time, you're telling them that you're guiding them and
especially if you're somebody who's in a professional conversation, they want to trust
that you know where the conversation is going and not feel like they've got somebody who
is wishy washy.
And the reason I gave the book that title is number one, I thought it would be shocking
enough that people would say, what the hell?
This is a book on interviewing.
Why are you saying don't ask questions?
But number two, because that's the freaking thing that gets me about conversations.
It's so counterintuitive.
Dude, you program.
Has programming ever seen this counterintuitive as human relations where you're supposed to
ask by not asking?
But that's the way it is, right?
Yeah.
And I think that the format of an interview is not my favorite format to listen to, to
learn from.
Like I like learning from conversations.
I like learning from discussions.
And if you look at how people discuss, you're doing exactly what you're saying.
Like two people talking to each other or rarely asking questions.
And it's almost never the case with one person is peppering the other person with questions.
It kind of looks like two people just making assertions at each other.
You know, you will just say like, what's going on with your life?
And it's almost like, you know, I listened to you, but then I just say my own thing back
and you say your own thing back.
And like, that's how most conversations are sharing opinions, sharing stories, sharing
experiences, and then reacting to what the other person says.
And that just seems far more authentic.
And when you have an interview or it's question after question after question, which sometimes
I'll do on this show.
Sometimes I won't.
It just ends up seeming more like an interview unless like two people who are actually friendly
with and know each other, and it's just not as fun to listen to, in my opinion.
I agree.
And you actually brought up something else.
You ever noticed that when you say something like a statement about how you're feeling
about something, the other person will say the same thing.
If you say, I've got a headache, the other person might say, I've got a headache too.
If you say, I didn't get to sleep well last night, they tell you, which as someone who's
learned how to have conversations, I could see if someone's telling me they didn't sleep
well last night, they're as a shove fact, they're screaming for me to say, what happened?
What were you going through?
How long?
Right?
And once I realized that, it bugs me that they don't, but it's interesting to see that
what they do is they tell you about themselves.
And if you look again at my interviews, if you look at your own conversations, if our
listener looks at their conversation, they'll see that in conversations, when you say something
personal about yourself, the other person instinctively will almost run with it and
talk about themselves.
It's frustrating, but it's also useful to know.
I'm kind of studying this.
This is why I can't appreciate, Courtland, that you're just a natural likable person
who likes other people and they like you.
I always think that nothing came naturally like that to me.
That means that everyone must be using some kind of system, but you swear you're not
using a system?
I don't think everyone uses a system, but I do think almost everybody learns.
And I think they're not the same thing, but they're similar.
A system is a way to kind of formalize your learning.
It's a way to say, I learned this thing.
I want to hone it and find out the essence of it and perfect it and remember it.
Whereas you can also just gain through experience, like as a child, I was horribly awkward and
introverted.
I was not one of the cool kids.
I went to my brother.
He was one of the cool kids.
All of his friends are popular in high school and middle school and he went to all the football
games and sat with the cheerleaders and whatever.
I did not.
But at the same time, I'm a pretty social guy.
I like hanging out with my friends.
And whether I have some system or not, I still just spent year after year after year talking
to people.
And that's practice.
I think without a formal system, you can still get better and I assume some of that's true
for you.
You have studied all this stuff.
You have a system, but you also have a wife, you have kids, you have friends, you have
a ton of people that you've talked to.
And even if you hadn't formalized any of your learnings, I would assume that you'd be a
much better conversationalist today than you were 15 years ago.
I don't think so.
I think I needed a system here.
I think if you, when I fail in my relationship with Olivia, it's because I don't have a process.
It's when she is complaining that we're in Austin because it's natural to feel like something
is different and why we hear where the strip malls are and what happened to all the cool
bars that you were telling me about.
And instead of relying on some process, some understanding, something that's organized
and intentional, I'll go, stop complaining.
I don't like when people complain.
Now, can you imagine that when you're feeling frustrated and you're sharing with someone
you love, they say, stop complaining.
And then the person does it over and over again.
That's the problem.
I do need a system for this stuff.
I do need a process.
I think that maybe I'm just so broken relationship wise or conversationally or maybe just, you
know what?
It just doesn't, it doesn't feel natural to me and to some degree when I use process
and forget about the process and just talk, it feels natural, it feels great, but it doesn't
feel like it's a logical, it doesn't come from a place of logic for me conversations.
People don't come from a place of logic.
I think there's a lot of truth to what you're saying and I'm super curious about it because
I just saw a couples therapist with my girlfriend on Tuesday and it's great.
I think everyone should have an individual therapist.
I think all couples should have a couples therapist.
I think co-founders should have a therapist.
It's just good to have a third party.
I think a podcaster should have a partner to look over your questions.
I think everyone should do things together instead of by yourselves.
And one of the things this couples therapist was telling us was that there's always tension.
There's always conflict.
There's always going to be limits that you run up to with your partner where you're going
to want to fight or you're going to want to disagree or you're going to have trouble overcoming
like your natural reactions to things and then he was just giving us some tools for
basically interrupting those natural unhealthy processes, for interrupting that process where
you say, you know, stop complaining, I don't like complaining.
Our process has a lot to do with, personally, I like listening.
I like active listening.
I find it very easy if somebody says something really offensive to me or that I really disagree
with to instead of taking it personally and wanting to immediately snap back to say, oh,
it sounds like you're feeling really frustrated because, you know, like I didn't put the laundry
up and you asked me to do that yesterday and I might have a million reasons in my head
for like why I can defend myself having done that.
But I also know how good it feels to be acknowledged and how much better they'll feel if they feel
heard and seen if I can just repeat back to them in their own words what they just told
me.
And so I think you're I think you're right.
Like I do think that there are these situations where like if my therapist hadn't given me
this tool, like I wouldn't use it.
So are you saying that with your girlfriend, you don't actively listen and acknowledge
what you just said and repeat it or are you doing it so much that she's saying, stop acknowledging,
do something about it.
Do the frickin laundry already instead of understanding how I feel about it.
It's the opposite.
My ex-girlfriend, who's a relationship coach and therapist, taught me all these tools.
And now when I date, I get frustrated when people aren't naturally using these tools.
Yes, that's a problem, too.
When you're a good listener, people don't I see you.
So what do you do when when she's not a good listener like that?
Try to teach and then realize I'm a miserable teacher and I've forgotten how to do it and
then go see a therapist who's actually a great teacher and a third party.
You can sort of disarm things.
What do you love about your girlfriend enough that you're going to go work through therapy
together?
Everything.
I mean, why are you going to be with somebody who is no, they're specifics.
I've got a list of specific things with Olivia.
I'm like, they're there.
For me, it was things like the way that we traveled together without being bothered.
I took her to the Balkans early on in our relationship to see how she deals with lack
of hotels and lack of air conditioning and all that.
It was all the way up to this is I like the way that our parents after they got divorced
talk to each other and how the whole thing like the whole thing worked out.
And I said, all right, even if things don't work out with us, I could totally see Olivia
being like her parents and being sane in a divorce.
Yeah.
What was it for you?
Specific stare.
I know Sarah, she's an extremely effusive and positive, I guess, complemented.
She has a way of making people feel special and sort of cutting to the heart of what's
good about a person.
I think I lack.
I'm a perfectionist.
Like I'm hypercritical.
Like I can see the flaws and a diamond.
She's the exact opposite.
And she also has this interesting combination of being extremely confident, borderline egotistical,
but also being curious and willing to learn.
And I think that the way the specialness that you can feel somebody who's confident and
proud of themselves and yet still looks up to you, it's just a new level of specialness
and greatness.
I also like how independent she is.
I mean, you and I were entrepreneurs, we're probably always going to have some sort of
interesting project or idea that we're chasing down and we're fascinated by.
And that can be threatening to people.
Like I've had relationships in the past where my partner was really threatened by the fact
that like, I like to work so much.
And with Sarah, that's not an issue.
She has a million and one thing she needs to do.
She's pulled in a million different directions at once.
And both of us trust that we still love each other regardless, that this is not a sign
that like our partner is less important, but that actually we're free to pursue our lives
in ways that are fulfilling.
And so I think that's a super rare quality and it's, it's important to be with somebody
that you're compatible with.
No, my Olivia's mom said one of the things she liked about Olivia's dad, one thing she
loved about him was that he told her early on in the relationship, my work comes first.
And she admired that that was so important and he's, he's an artist, he's a fine, he's
a sculptor, fine art sculptor, I guess is what it's called.
And so for some reason, if you say that about your work, that's in an office or a tech company,
you feel like a jerk, but if you say that about art, you feel inspired and meaningful.
But I like where she was coming from with that and I, it seems like the two of you feel
that way too, that if work has priority in your life, maybe not above each other, that
it's important.
It doesn't necessarily need to be a threat, you know, and, and I think that for a lot
of people, like seeing your partner succeed, seeing your friends succeed can be something
where you, you start to think about how they reflect on you, you know, like, Oh, my friend
just raised a bunch of money for his company and blah, blah, blah.
What does that make me a failure?
I think it takes a lot of confidence and positivity to look at that in somebody else and not get
defensive and not feel like this is somehow a reflection on you.
What drives you right now, like you got your equity in Stripe, you got a job there.
Why are you not just either calling the quits or starting something else?
I got a lot of questions for you that are in the exact same space.
Okay, you're laughing.
But I'm curious about that.
Yeah, yeah, yeah.
I am in the process of basically trying to figure out, I don't want to say the right
way to live, but the right way for me to live.
Like, what am I living for?
I think our culture kind of has an obsession with like, what's the meaning of life?
Which is on its face, kind of a silly question, because like, meaning is something that it
takes a conscious mind.
You have to have a conscious mind that imbues something with meaning.
Things don't just have meaning on their own, which means the meaning of life is going to
be different for everybody.
It's what you decide to make of it.
And I would really like, you know, the arc of my life to have some sort of meaningful
story that at any moment, I could tell somebody else, I could tell myself.
And then when I'm on my deathbed, I can look back and say, this is what I did.
And I think up until I built Indie Hackers and sold it to Stripe, I didn't have a very
meaningful life.
I think I was like, I want to vaguely build a startup and get rich and be successful and,
you know, pursue this stuff because it'll be kind of fun.
But okay, once you do that, like, goal achieved.
And it's this kind of sinking feeling after a few years of like, I don't have a reason
to live.
Previously, I had a really strong reason to live.
And so for me, like, I'm, if I'm doing anything right now, it's kind of searching for that
meaning.
I like doing what I do.
I like helping founders.
I like talking to entrepreneurs and learning and I like the people that I surrounded myself
with.
It's great.
But that's not necessarily meaning.
That's more like short term enjoyment.
And so I'm trying.
I mean, I'm kind of in search for a meaning for a reason to live.
And that involves things like do I want to get married?
Do I want to have kids?
Do I, if I do have kids, you know, what kind of father do I want to be?
Do I want to start another company?
Do I want to switch careers?
I don't want to do any of these things arbitrarily just because they feel good in the moment.
And then try to like, in hindsight, stitch them together into some sort of meaningful
story.
I want to be more deliberate about what I want to accomplish and what I want to do and
how I want to feel.
And I think that's a tough question.
It's a tough process to go through.
I feel very fulfilled by the fact that like I'm doing it deliberately and I'm thinking
about it.
And I wanted to know the same for you because you've been working on Mixergy for well over
10 years.
Before that, you had a very successful business that was doing tens of millions of dollars
in revenue.
You're married.
You have kids.
You made a lot of these like very big decisions in life that I want to know what the meaning
is for you.
What's the meaning of your life?
And where do you want to go?
Deliberate, very deliberate my whole life to the point where I wouldn't go and hang
out unless there was a clear end goal, unless there was a benefit to doing it.
And over the last couple, I think it was after I finished my run on Antarctica, I said, what
do I don't, I think I need some time without being so deliberate.
Deliberate is, is helpful, but maybe it didn't get me where I wanted it to go enough.
I don't know where I want it.
I do know I wanted to be one of the richest people in the world.
I wanted to do all this other stuff.
And I realized I really have things that I enjoy reluctantly, that I really enjoy doing.
I enjoy running.
I enjoy traveling.
I enjoy being with my kids.
I enjoy being with Olivia.
Um, lately I've been enjoying chess.
And so I've been letting myself enjoy it.
There was the, this past Sunday, I just had hours and hours to myself.
All I did was play chess for the love of the game of chess.
And strangely, I'm at a point in my life where I'm giving into that.
I don't think it's a great long-term way to live.
You know, I'm, I've hit that thing that the Zen Buddhist masters would want you to do,
which is live in the moment.
I'm not thinking about the future.
I'm not thinking about the past.
I'm just right here.
I just don't agree with them that that's the best way to live.
I don't think you end up with a meaningful life.
I don't think you impact the people around you positively enough.
I think you just feel it's very self-indulgent, but I'm letting myself be self-indulgent.
That's a cool place to be.
What would you say that you were deliberate about when you said you're living deliberately
and you wouldn't go hang out unless there was a purpose?
Were you just deliberate about making money?
Were you just deliberate about financial and sort of externally validated success?
I think so.
I think to say it's about money was, was not exact.
It's definitely about money, but it wasn't about any more than just using it for points
and then giving it away.
I, I don't love things and it seems like there are a lot of us now that just don't love things
of any kind.
So it wasn't about that.
It was just, I think in order to have a meaningful life, you build a company where you give
people work that matters and products to buy that matters, where you have bigger and bigger
things that you build, where you don't have to be a drain on society financially, where
you get to then help out other people.
It's all that stuff is, that's, that's what it was.
And so for example, my friends would say in high school, let's go out and they'd want
to drink somewhere.
And to me, that wasn't meaningful.
There was no upside in, in doing that.
And I would be the person who would say, I want an upside in this and I don't see that.
Right.
I identify with that so hard.
And I bet you a majority of people who listen to this podcast, a majority of the people
in Silicon Valley have a kind of a similar personality type.
My actually did a lot of relationship and coaching and just individual therapy in San
Francisco.
You used to always tell me, uh, you're a human being, not a human doing people don't love
you for what you do.
They love you for who you are.
And she said, she had to tell that to a lot of people who are up and coming in the startup
world who feel to some degree, like we're defined by our achievements were defined by
what we can do in the world.
Uh, and that makes us sometimes uncomfortable with just being because it feels like wasting
time.
You're not, you're not achieving this.
I'm still going to say that I feel that human doing is more important than human doing than
human being and human achieving is more important than either of those other two.
And I'm just not at a place right now where I want to do and achieve and I'm okay with
being.
I think having that stressful, painful period of writing down what I learned over the last
few years was so much tougher than I thought that helped too, to be able to say, okay,
I did all this.
I'm leaving this behind, you know, this set of techniques that came from what I've learned
that that was really helpful.
I think going to Antarctica and before that it was all six other continents and just on
my own running marathons and getting space in my head gave me space to say, I think I
want to now just be a little disconnected.
I think, I think that I want to indulge a little bit in those personal desires.
Did you just need a break from, from the stress at the time of work?
It might be, it might be.
I don't think that I've been under stress in years, but I do think that I've been under
work.
And it's not so much a stress as maybe burnout, burnout stuff.
I literally just went through a pretty big burnout period myself with indie hackers,
I would say from probably March of this year through maybe a month or two ago.
So like the end of July and it is tough to operate a podcast when you're burned out.
It's tough to get up every single day and have to prepare for an interview that you're
not really sure you want to have and then record it when you feel like you'd rather
be doing almost anything else.
So why'd you do it?
Social accountability, obligation, peer pressure, not wanting to let others down, which is an
incredible force because I think overall it was good for me to have those things and it
was good for me to push through and do the work that I needed to do and prove to myself
that I am reliable and prove to other people that they can rely on me, even if it didn't
always feel good in the moment.
But damn am I lucky to have a situation where I essentially am going to get paid no matter
what and I don't necessarily need to be, you know, killing it every single month of every
single year.
I can have some, some time off and I think that it's hard to get if you're not an entrepreneur.
I think that's another important thing to say that there have been times in my life
where if I failed, there would be no money and it was adding so much more stress.
There have been times in my parents if, if they couldn't pay for our medical bills for
whatever reason, we didn't have health insurance, we would be in trouble.
I do think that we talk about where I am in a place of I'm just here in the moment and
all that.
That's nice to indulge in right now the way some people would indulge in a nice long vacation.
But when I see indie hackers on your site building and I know that at times some of
them are getting shingles and other issues, right?
I think it's worth it because it's pain in the moment for a lifetime of upside where
one day they're going to be able to do what you did, which is go through burnout without
having to risk their family and have the stress of that on top of burnout.
And so I think, I think that's important.
What do you think about the concept of balance though, because you're talking a lot about
like living in the moment versus, you know, living for achievement and aspiration.
And I'm at a place now where I think balance is the most boring advice in the world.
Eat a balanced diet, live a balanced life, like make time for friends and relationships
and your health and your sleep and your work.
And it's so cliche and so boring that it almost like I almost told myself wanting to revolt
against it.
And to start a startup is to almost, it's almost a glorification of living an imbalance
like to just go super hard as you were saying, pedal to the metal.
And maybe these first few years will be tough, but then you're going to strike it rich.
And the rest of your life, you can have balance.
How do you think about balancing the fact that you want to take time to live in the
present, but you also want to do these big aspirational things?
You have to choose one or the other.
I've learned that I just can't balance stuff very well.
I'm also not someone who when Olivia and I are on a date, I'm pulling out my phone and
texting you.
You can, if I ever do, I should say occasionally might happen.
It's going to be the biggest weirdo text with all these typos.
I just am so in the moment when we're there.
And also when I'm working, it's annoying that we're working out of the same Airbnb together
because I'm such a pain in the ass to talk to because I'm focused on what I'm doing.
I go all in like that.
I think there's some people who are better balanced.
I have noticed this about myself that it was a period when I was really depressed when
work wasn't doing well and I took up running and then running did well, you know, and it
was just like 45 minutes of running.
And if I had a good run, it made the rest of my day feel like I could do anything that
I'm accomplished and it helped.
And for a long time, I felt a little bit weird about that.
And I thought maybe there was something wrong with me.
And then I remember talking to Tim Ferriss about it and he was a really big, he's just
someone who's all in on stuff and he cares, but he was really big on saying that that's
important to have that, to have those other things so that they help you stay focused
on the things that matter.
And so for me, having, having running, having a relationship, having kids, having other
things that matter is, is helpful.
If I'm, if I'm having a really bad week, but I beat somebody better than me at chess on
chess.com.
That's great.
Feels pretty good.
Chess is such a good game.
It's such a good game.
There's a really funny quote from a chess master.
Uh, I forget the exact quote, but it's something to the tune of, uh, a life spent mastering
chess is a life wasted.
And this is like from like, uh, one of the world's like best.
I think it's like Morphe who like retired at chess at age 30 and then went into like
business or something, even though he was like a world champion.
And it's so addictive.
I can see exactly what he meant where it's so addictive and you're like, yeah, in your
mind to see all these patterns and to get so disciplined and so good, but at the end
of the day, then what do you have?
Like you're good at this game.
It doesn't matter that much, but I think the level that you're playing at and that I'm
playing at is like, it's just fun.
We're not that all in on chess.
Right.
And there are times when it gets too super addictive, but, uh, I went into chess thinking
learning about chess is going to help me think several moves ahead in life.
You know, that we, we've come to understand that someone who sees the chess moves of life
can say, if I say this to this person, they're going to do that.
And if I do this and bid, it turns out that there's a little bit of that, but mostly it's,
if you're good at chess, you're good at chess.
And I'll even watch these streamers who play chess and people ask them, does this mean that
you're great at all this other stuff?
And they'll say, no, all I am as good at is chess.
It's true.
And I do think the one thing that you get out of chess is that sometimes very deliberate,
slow methodical thinking is like physically uncomfortable, like to calculate moves and
then look ahead and chess.
Right.
It's like you're burning calories and it is not that fun to be in that mindset.
And I know that notice the older people in my life, when they go to learn a new thing
or try something different, I can see them like the resistance in their mind.
They don't want to learn these things.
It's going to be burning calories.
And they want to do things the way it's always been done.
So at the very least, I think chess is sort of like a repeated deliberate practice and
pushing yourself into a mentally uncomfortable place where you're having to do this mental
work and you can't sort of lapse into this mental laziness.
But beyond that, I don't think that single skill from chess is terrible.
There's one other thing that I've gotten out of it.
If you use chess.com, they do this post game analysis, especially if you have the premium
membership, they show you what your key moves were.
And it shows whether you are a header behind throughout the game.
And I do this after every single match.
And it's shocking to me how in the beginning, there were times when I thought I had failed.
I lost.
But when I do the post game analysis using the computer, I can see the computer put me
ahead of the competition.
I assumed I lost.
I couldn't wait for the game to be over so that I could study and learn from it.
But in reality, I should have played the game to the end and understood that I was ahead
and that there was a checkmate available or that there was a way for me to push the pieces
in.
And I think that there are times in all of our lives and I know for sure in mind where
I thought I was behind, but in reality, I was further ahead.
I thought I was, I was, I'll give you a great example.
I launched Mixergy Premium.
I thought because we did 50,000 a month in sales within a couple of three months, I don't
know how long, within a year we did 50,000 sales.
I thought it was a failure because 50,000 a month in sales is so little compared to
what I thought everyone else was doing.
It's not even a million a year and it's just selling these videos.
And so you don't get that in the rest of life, but it's really helpful to be shocked into
accepting the times when you think you were ahead, you weren't.
When you think you were behind, you weren't and to just play it out.
And frankly, there are times even in chess, I'm fully behind, but it's just a couple of
moves at the end that allow me to win.
There are times when people have given up, they resigned to me and I say, I'm going to
play this out and see, could I have beat them?
It looks like I could have, but no, it's much trickier of the situation.
So in that way, I've gotten a really important lesson.
Now it's me driving a lesson out of it.
It's not so much that you do chess and you get it, but that was an important one for
me to remember.
That's poetic and super important.
And I think that applies to so many different things like even, even just like if you are
an ambitious founder type person, you're probably surrounded by a bunch of other people who
are similar, who are early adopters, who know all sorts of stuff, who are doing very impressive
things.
And it's easy for that to shift your perspective to think you're behind everyone else is bigger
and faster and further ahead than you in 2014.
I thought I was too late to Bitcoin.
I'm like, Oh, I'm so far behind.
And it turns out like, I'm just living in this weird little bubble where everyone around
me is so far ahead that I think I'm behind and it's just a matter of perspective.
So I think it's, it's beautiful that you, I'll tell you, I, there was a time I thought
I was way ahead of you.
You were, you sold your company to Stripe.
I said, this guy couldn't cut it on his own.
You told later on that you, you were just looking for a sponsorship from Stripe and
then they ended up buying you.
Right?
So that's where you were.
We were giving you from sponsorship and you sold.
It turns out you were way ahead than further ahead than we realized because of that one
decision.
You just can't tell.
And I think as we look at other people, you've always been very good about saying we should
not be comparing ourselves.
You did this great interview with Jason Calacanis where he was basically looking for that juice
from you and you weren't going there because I think naturally you've gotten to a place
maybe I shouldn't say naturally where you, where you don't do.
And I think it's really important.
You're in a place with this community at Indie Hackers where it could be super competitive.
You've got people's numbers up on the screen for everything, for how many upvotes somebody's
article got, for how much money they've made and you've tied into their Stripe account.
Right?
It's really important that you're coming from a place of not using those metrics as a way
of analyzing who people are.
And I've seen you, you just don't, you just don't do that.
I on the other hand do.
It's hard not to, it's woven into us to compare like we are a status based creatures.
We evolved in these tribes of status hierarchies and our reputations matter and we're kind
of sort of naturally wired to look at like, where are we in the pecking order?
But at the end of the day, like that's a game you can't win.
You know, if you're in middle-class American, you might be looking at people wishing that
you saying, look at these assholes and you're ignoring everybody who's poorer than you,
you know, and if you're an upper-class American, you're looking at the billionaires, like look
at these assholes and you could play that game all the way to the top and never be satisfied
with where you are.
And I know people who do it and it's really, really hard to break out of it.
But listen, Andrew, I know you've got to run.
Did you notice like how much this interview changed when we literally started using your
advice of not asking questions and we just had a conversation and it went from me asking
for all these tactics in your book to just us talking and riffing on life wisdom and
our experiences.
And it was much more conversational, much less of a sort of staccato interview, I think,
as a result of that.
I do.
I wonder as listeners, which approach people like and I actually have learned that they
like both, but I wonder when they're coming to indie hackers, which are they looking for?
Are they thinking I came in for tactics and damn it, Cortland, why'd you have to have
a conversation with Andrew?
Or I came in to just learn naturally who Cortland is, who Andrew is, to get a real conversation
that I might have if we're, if we were all in the same, I don't know, neighborhood, they'll
tell us, I'm going to give them my email address.
I hate getting email, but I want to, I want to know this answer, andrew at mixergie.com.
That's my personal email address.
It goes directly to me.
Is there, is there another way for me to just get some, some more input from people?
I'll put your email in the show notes too, Andrew, so people can find you.
My guess is that people fall in both camps.
Some people will be like, I wanted more tactics.
Some people will be like, that was super entertaining.
Do more down to earth episodes like this.
Maybe it falls to us as podcasters and interviewers to decide which kind of audience we want to
cater to.
By the way, don't close this out without me acknowledging you have the best freaking t-shirt
in the whole startup space.
Everybody else plasters their stupid name all over the t-shirt.
Like I have to be a walking billboard for your stupid.
Let this be a lesson.
Forget teaching anything else.
Teach people how to create a great t-shirt.
A t-shirt like this, nobody even knows that it's indie hackers unless they're in the
in the hackers community.
People just happen to like it because it's got an astronaut on it, but if you know what
to look for, you pick up on the clues of it.
I know that it's an indie hackers thing.
When I put this on, I feel like I'm an indie hacker.
I feel like I'm part of this community, right?
If that's what you want, stop, listen to me entrepreneurs.
Stop putting your stupid logo on people's t-shirt.
Nobody wants to wear your logo.
You're not freaking Nike.
Take it about the ethos, the vibe of it, subtly downplay your logo.
I would even suggest this to somebody who's listening.
Create a t-shirt where your logo is on the inside.
Only the person who wears it should know that it's your logo.
They're not going to be this great promotional vehicle for you.
Go buy a freaking billboard ad or an ad on Facebook if you want a promotional vehicle.
If you want to touch somebody by being on their chest, in their house, in their lives,
make the t-shirt look so damn regular and good that they want to wear it or freaking
A, just copy Cortland.
This t-shirt is the best.
I bought t-shirts from you.
They're so good.
Regular t-shirts.
Look at this.
Forget teaching entrepreneurship.
Teach them to just have a little bit of understanding of the world and not think that everyone wants
to wear their stupid logo.
I love that rant.
I love it.
And that's exactly why I designed the t-shirt that way because of Mailchimp's t-shirt, which
has a super cool picture for Chimp on it.
And I was like, why would anyone ever make a sort of feature with their own logo on it?
This is way smarter.
Anyway, thanks, Andrew, for your time.
I hope to have you back on the show more regularly.
Thanks.
And I'll see you guys next time.