Episode 645 | Anti-Bro, Nuanced Thinking, and Being Good vs. Being Great (A Rob Solo Adventure)

Rob Walling:
I showed up to dinner and I think my belt buckle … I’d gotten out of a cab or an Uber or something. My belt buckle was literally two inches off to the side. And one guy said, “You got to straighten your belt. You run a conference now.” And I remember thinking to myself, “What in the (beep) are you talking about, man?” I’ve run five of these events, six of these events. This was my house. I remember feeling that. Like, “This is my house. You don’t come in here.” And it’s little levels of disrespect that just don’t need to be there.
And no one else does that. The only people that have come to MicroConf and said things like that happen to be these overconfident folks who had hopped in. And I’m not ragging on San Francisco per se, but we do know that there’s that “startup bro” feel that maybe just doesn’t jive with who I am, doesn’t jive with what MicroConf is, and it doesn’t jive with the community we’ve built.
Welcome back to Startups For the Rest of Us. As always, I’m your host, Rob Walling. And this is the show where we talk about building and growing bootstrapped, and mostly bootstrapped startups, through relentless execution and thinking in terms of years, not months. We know that this is a marathon, not a sprint. And maybe I can throw in another cliché metaphor right here. But no, it’s about thinking about things over the long-term and about shipping something every day, but not expecting that to move the needle immediately. Usually realizing it takes months, or in most cases, years to build something great.
Thanks for joining me again today. Today’s episode is a solo adventure where I talk through a few topics that are on my mind. I’m going to talk about whether bootstrapping, or maybe it’s MicroConf, is the “not-bro,” the “anti-bro” startup movement. Why today I think, in social media especially, it’s cool to be angry and that there’s more nuance to a lot of different situations. I’m going to bring up some examples of conversations I’ve had with my kids recently about that. And then talk about this headline where someone declined a $9 million acquisition at age 18 and then went on to build this company we’ve all heard of. And speaking of nuance and getting a little angry, the headline is sensational and I just want to point out what they got wrong, as well as dive into the difference between working with someone who’s good versus someone who’s great.
So to start off, I want to talk about this “anti-bro” startup movement thing. This occurred to me about four or five months ago, and I put it in this Trello board where I keep my solo topics. And the sentence is, “Is bootstrapping or is MicroConf the “anti-bro” startup movement?” And it felt to me a little weird to even say it. I often don’t want to come out and bring this negativity, this anti anyone mentality, into the world.
But then I was at MicroConf Local in Austin last month, and I want to thank Sarah for encouraging me to talk about this. Because she and I were talking, Sarah’s been to a few MicroConf. She said, “You know Rob, I want to commend you that the community here is so welcoming and it doesn’t in any way have that ‘bro’ vibe.” And she went on to say that she has gone to some startup events where it doesn’t feel great, and the energy in the room is such that it’s not welcoming to everyone. And I actually told her, I said, “I have this idea, and I was going to talk about it but I haven’t and I’m not sure I’m going to.” And she said, “You absolutely could,” and I can give you a bunch of examples. I didn’t want to take it to that point, but realistically, I did want to call this out because it’s something I think we stumbled into accidentally. But then once we got it, we have been very deliberate about guarding.
And it’s that idea of, A, everyone is welcome, and B, anyone can do this. It’s not like you have to be a particular type of person in any way, shape or form to bootstrap. I’ve talked about it as being the great equalizer and I believe that. I believe that almost anyone, now especially with no-code, but with code, with learning to code, with all the resources online today, that people can change their lives through bootstrapping. And not just through software bootstrapping. You can bootstrap product-as-services, you can become a freelancer, you can sell info products. There’s so many ways that bootstrapping changes lives.
And when we started talking about that on this podcast 12 years ago it was two bootstrappers who kind of knew what they were doing, who are not very “bro.” And when I think of “bro” I think of the overconfidence, the swagger, the negging, if you’ve heard of this, N-E-G. It’s like attacking or trying to be alpha, trying to out macho the next person. And it’s this energy that can feel overbearing. So the typical version of that might be, you’re in high school and there’s a bunch of jocks and they’re big and buffed and might makes right. And it just kind of sucks to be around them if you’re not one of them. And it’s a very inclusionary, exclusionary thing. That’s, anyways, how I think of bros.
But what really got me thinking about this originally, is there was a year at MicroConf where four or five people came from San Francisco, and it was crazy. They were the prototypical startup bros. Like they were doing paleo, they were talking about Soylent. They were everything I just said, the swagger, the negative, the, “I’m going to out whatever you … Whatever you do, I have a one-up.” Here I am, running this event, MCing the event, built this great community, and somehow the things they did were all better. And it just came … Really sour, really bad taste in my mouth.
And I remember thinking at the time, “If this is what MicroConf is becoming,” which it wasn’t and it isn’t, “but if this is what MicroConf is becoming, I don’t want to be part of this. I don’t like communities like this.” I’d been to [inaudible 00:05:19] where it’s this big competition to measure who was further along, who was better, who knew more people. It was the name-dropping. It’s all stuff that I just don’t have a desire to be involved in.
And I remember one example was, I was wearing a shirt from … It was called Structure at the time. And it was a pretty nice, fitted shirt, but I am tall and skinny and so my shirts never fit me quite right. And one of the guys was like, “Oh, I see your shirt. This is a tailored shirt tailored for me.” And I was like, “Oh, that’s cool.” “Yeah, you should really get one.” And I’m like, “Yeah, I will. Right now I’m investing in my startup. I don’t have the 150 bucks to drop on a shirt.” But it was this implication that somehow I was less, or my outfit was less, because of that. And again, it was someone’s first time meeting me, it was their first time at a MicroConf. It just feels like there’s a level of respect or a level of appreciation even, rather than starting to criticize or hint that somehow I’m better than you because I have this shirt.
The other comment someone made, it was for these four or five guys in this group, is I showed up to dinner and I think my belt buckle … I’d gotten out of a cab or an Uber or something. My belt buckle was literally two inches off to the side. And one guy said, “You got to straighten your belt. You run a conference now.” And I remember thinking to myself, “What in the (beep) are you talking about, man?” I’ve run five of these events, six of these events. I mean, at the time it was still early, but this was my house. I remember feeling that. Like, “This is my house. You don’t come in here.” And it’s little levels of disrespect that just don’t need to be there.
And no one else does that. That’s the thing. The only people that have come to MicroConf and said things like that happen to be these overconfident folks who had hopped in. And I’m not ragging on San Francisco per se, but we do know that there’s that “startup bro” feel that maybe just doesn’t jive with who I am, doesn’t jive with what MicroConf is, and it doesn’t jive with the community we’ve built.
And so I just want to call this out, because I’ve talked to folks who come to a MicroConf for the first time and they’re surprised that it is so welcoming and that it doesn’t have a bunch of bros in it. And if you’re a listener and you feel like, “I’m not going to fit in.” Like Anna Maste said, what, a year ago when she came on the show, and she said, “I just figured I was a woman with kids, growing a startup on the side. I’m not going to fit into any startup community.” And then she came into MicroConf and found out, “Oh, I fit into a startup community.” That’s what I want to express here. That’s what I want you to take away from this piece.
The second thing I want to talk about is something I’ve been talking to my kids about, but also it’s just constantly circling us on social media, and it’s this idea of, “I’m going to be angry about everything. I want to be outraged.” And I’m not saying that for me, I’m saying it seems like people on social media just want to be angry about everything. And the thing I’ve been telling my kids is, there’s always more nuance to this story, in almost every case. Of course, always is too strong a word. There are some cases where there’s very little nuance. Almost all cases there is nuance.
Elon Musk buying Twitter, cryptocurrency, NFTs, these things are way more polarizing than they probably should be. Now I will admit, Elon Musk buying Twitter is becoming more polarizing in a way that I think it should be, at least as of today. I’m recording this probably a month in advance, and so it’s almost hard to make comments about what will happen if things will completely go off the rails in the next month. But the idea that, say, a company could announce that they were going to issue an NFT and have people just losing their minds about it six months ago, a year ago, was just so surprising to me, because NFTs are just technology. This is being angry at someone for using an SSL certificate.
We can argue about energy usage. My kids were saying, “Well, NFTs use a bunch of energy.” And it’s like, they don’t … No, not necessarily In some cases they do, but there’s nuance. That’s what I’m trying to get to. There’s more to it than the headline take, the hot take that got you to click. The hot take that you read and then didn’t read the full piece. And the full piece, if it wasn’t written by an expert, probably didn’t have great info in it anyways. How many articles have you read in your field of expertise, when it’s written by a layman journalist, and you read it and you say, “That doesn’t make sense. That’s incorrect. They misuse that there.” No one else notices because you’re the expert.
So when the headline says, “NFTs are going to ruin the world. They sucked on all the energy and they’re a scam.” And then no one reads that article, because they just want to see the headline and, again, be angry about it, here’s what I do. I dig deeper or I don’t comment. I educate myself on this. I try to get facts, and I realize these days are facts in quotes now. I still believe there are facts and I try to find them. I try to find the sources that I think are going to deliver balanced information. And if I can’t find it or if I can’t form an informed opinion, then I don’t comment.
And that’s what I’ve been talking to my kids about. I was saying, “It’s cool for us to have a conversation here.” I’m not saying we shouldn’t talk about crypto, NFTs, Elon Musk, or any other polarizing topic. There of course should be discussion and discourse around it. But discussion and discourse on social media is not the same. Almost instantly it turns into name-calling and arguing. It’s completely counterproductive. And it’s just, it’s cool to be mad. And the madder you are, the hotter your take, the more thumbs up and retweets and likes you get, but there’s more nuance to it.
And that is one reason why I spend so little time on social media or when I’m on social media, I absolutely create filters. I mute and block people that I feel like have these takes that are uninformed yet very certain of themselves. The moment I see someone who is so certain of something, using all caps always, all caps never, it makes me very wary of listening to them. Even if I agree with them, it makes me wary that they’re not someone who looks at the nuance of situations, and who has probably formed an opinion based on one or two limited experiences.
The plural of anecdote is not data. I think Sherry heard that when she was getting her PhD in psychology and they did a bunch of research. They said, “Yeah, a bunch of stories does not mean data.” It doesn’t mean qualitative and quantitative or not both important, but this is similar to the startup founder who has one success and then comes out telling everyone, “This is how we should do it.” Or, “I’m an expert. I’ve grown startups and I have all this experience and I have all this knowledge and all these things,” when in fact, an n-of-1 is just that, an n-of-1. So I hope from that you’ll take away, there’s always more nuance, and dig deeper or don’t comment.
Speaking of digging deeper, I got an email for … It looks like it’s from DealMakers. I don’t even think I signed up for this list, but the subject line was, “Declining a $9 million acquisition at age 18 and then going on to build Vimeo.” And I read this. And I texted a friend of mine, Ruben Gamez, you’ve heard him on the show before, founder of SignWell, and I said, “He should have taken the money.” This is an anti-pattern of entrepreneurship. If you’re 18 and you’ve built a business to the point where someone offers you $9 million, you take that (beep) money. That changes your life. You will put yourself through college if you want to go, your kids through college if they want to go. You are set for most of your life with that. Don’t be dumb and believe that this is somehow a virtue to turn down a nine (beep) million dollar acquisition offer at 18.
I was mad. I was angry that they were abusing this headline, and that it was somehow being shown to be virtuous or the right decision. And then guess what? I started reading the piece and it turns out it was a terrible offer. From what I can tell, it was an all-stock offer of $9 million in stock in a private company, some venture-backed company. And then I was even angrier, but I digged deeper. That’s what I did, I digged deeper before I went up and spouted about it on this podcast. Or I never posted it to social media, but if I had, I would’ve then at least had both sides of it of, A, take the money. If you get a life-changing exit, do it, and then take another swing at [inaudible 00:13:12] with your next startup, as this founder did. Because the $9 million acquisition offer wasn’t Vimeo, it was something prior. He had many acts in his play. He had so many more things coming up in his life.
But then secondarily, this headline is clickbait. It’s like, yeah, a $9 million acquisition offer, let’s put that in quotes. It’s a crap offer. Let’s be honest, it’s all private stock. From what I can tell again, it’s like no cash or almost no cash. In that case I probably wouldn’t have taken it. And so therefore the headline that makes me think I should be shocked by it, it’s inauthentic, it’s manipulative.
All right. I feel like I’ve been a little more negative than usual, so I want to do a little positive segment here. I have always been fascinated with outlier performers. Meaning, people who in their field are so good that they transcend that field, some of the greatest of all time. I’ve never played hockey, not particularly a fan of hockey. It’s fine, but we all know who Wayne Gretzky is, and I’m fascinated by how good he was and how he got that way, how he thought about it.
I never played baseball in high school or college or any type of organized fashion. And yet, Facing Nolan is a documentary about Nolan Ryan, just came out on Netflix, it’s very good. And I watched it on the airplane. Not because I care much about baseball, because I’m so fascinated by this man who pitched in the majors for, I believe it was 22 years. He stopped pitching in the major leagues when he was 46 or 47-years-old. He has records people say will never be broken. He has something like 5,000 strikeouts. The number two behind him has 3,900. He is so far, so far ahead of everyone else that it fascinates me.
And I just want to understand, what was his work ethic? How did he think about things? How did he get there? Was it hard work? Absolutely. That is one thing that you hear through all these stories. None of these folks sat on their natural talent. They all worked incredibly hard. And their teammates will all say they were there, shooting baskets, or shooting goals, or throwing baseballs, long after their teammates left. But other names who are outliers. Michael Jordan, Bruce Lee, I love learning about Bruce Lee and how he thought about everything. Paul McCartney. And what’s crazy is, if you watch documentaries about this or you read books about them, is there are commonalities in the stories. And I find that pretty inspiring.
And so I’m going to pull in some audio from a YouTube video called I Learned 227 Beatles Baselines and Discovered This. And the reason I’m pulling it in is I really like the way this basis described Paul McCartney’s baselines and how they developed over time. And how, for the first several years, the baselines were very simple. They’re just root notes. And in fact, so I play a little bass and I play a lot of root notes, and just not that good. I mean, I can play. I’ve played in bands and I can play on stage, but I’m fine. I’m just a solid rhythm bassist.
When you listen to McCartney’s baselines as they progress through the years, the seven years when the Beatles were recording, he really starts upping his game around fifth or sixth album, like Rubber Soul and a couple of others. And he moves from being a root note kind of rhythm instrument to almost being another melody, or to being a harmony behind everyone. And the cool part about this audio I’m about to play is that this bassist shows the basic … He puts in all caps. If you go to watch the video, we’ll link it up in the show notes, but he says, “Not what Paul McCartney played.” And he’ll play it and it sounds perfectly serviceable. And you’re like, “Yeah, that’s cool.” And then when he plays what McCartney played you’re like, “Whoa, that is transcendent. That is so much better.” And I believe that Paul McCartney is one of the best songwriters of modern times, and I believe he’s one of the best bassist of all time.
And this example right here shows you the difference, that even if you don’t play bass, even if you don’t think about music in this way, this is the difference between being good at something and being amazing or being world-class or one of the best of all time. And so the song, Dear Prudence, on the White Album, let’s listen to what Paul didn’t play, the basic version of what a good bassist might play.

Speaker 2:
(singing).

Rob Walling:
And then this is what Paul actually played on the song.

Speaker 2:
(singing).

Rob Walling:
And then one other baseline is from the song You Won’t See Me, and here is What Paul didn’t play.

Speaker 2:
(singing).

Rob Walling:
And then here is the amazing baseline that Paul actually plays on that song.

Speaker 2:
(singing).

Rob Walling:
And here’s what’s funny, even though I never played hockey, didn’t play baseball, and I can kind of play the bass. I can’t read music, I can’t play any of the bass lines you just heard Paul play. I can’t play those bass lines. So it’s not because I happen to music that I am enamored with Gretzky, Nolan, Jordan, McCartney, Bruce Lee, it’s the ability to be so focused on something that you become one of the best at it.
And to link it back to entrepreneurship and startups and bootstrapping, I mean, I think there’s a couple of lessons to take. If you’re truly lifestyle bootstrapping, you want to do what you want to do and you don’t want to be the best at anything, that’s okay. To each their own. But I think I’ve always been a relatively competitive person, as competitive with other people, but also with myself. Competing to get better at things, and I enjoy that idea of mastery. I enjoy when I go back and watch a video that I recorded, listen to a talk, listen to a podcast, read a book or read a essay, and to say, “That’s really good. I’m proud of that.” I think I take a certain amount of pride in shipping something that lives up to my taste.
And I haven’t done that in a lot of areas of my life. I was in bands. We would record music. My vocals were never as good as I wanted them to be, I was always frustrated with it. When I ran track I was never as fast as I wanted to be, no matter how hard I worked. But I have found mastery in other areas where I feel like I’m pretty good at this. Pretty good at recording podcasts now. Pretty good at talking about startups and about thinking about all the stuff we talk about here on the podcast.
And so I think there’s a couple of aspects to this, is if you want to improve, think about how you can put that hard work into play and how you can focus on things. Because I do see people doing too many things if they want to be good at any of them. And launching 10 products instead of focusing on one, or trying to be good at 10 things instead of trying to be good at one, each of these is going to be a decision that impacts how good you can be at something.
And also, this lends itself to thinking about the people that you work with. I’m not saying that the team members you work with, whether co-founders, people you hire, that they need to be world-class, some of the best ever, because it’s just unrealistic. But there is the difference between someone who’s good and someone who’s great. And oftentimes it’s how much they care about it, how much ownership they take of it, and it’s putting in the focused time and working on the right things. I think that’s a big part of this, is you have to imagine the Gretzky and Nolan and McCartney and Bruce Lee, that they worked on the right things. Because if they worked on the wrong things they wouldn’t have gotten better at these tasks.
And I think, again, for you and your teammates or co-founders, what are you focused on? Are you putting in the hard work? Are you putting in the focus, or are you getting distracted by social media every 20 minutes? Are you working on things that last? Are you building a startup that will be around for a while? Are you shipping code that will be around for a while? Are you writing blog posts or essays that will be around for a while? Or are you focused on things like, “I’m going to send out a tweet because I get a dopamine hit,” but that tweet is gone to the wind in an hour. It’s ephemeral.
Each of us probably has a few things we should focus on, and each of us probably has a few things that are the right things for us to be working on. And as I wrap up this week’s episode, I want to challenge you with finding those things for yourself. Wow, so that got kind of deep. I hope that was inspiring for you, rather than a heavy listen. I enjoy doing these solo adventures and hope you enjoy listening to them. This is Rob Walling, signing off from episode 645.