Rob Walling

But it isn't always apparent just how much struggle each of us is going through. And frankly, I'm just going to mea culpa here, how many mistakes each of us makes, even once we kind of know what we're doing. Like the level of mistakes that I've made in the past 10 years is pretty incredible. So why have I achieved, you know, I would say each year I've been kind of more successful than the last.

But it isn't always apparent just how much struggle each of us is going through. And frankly, I'm just going to mea culpa here, how many mistakes each of us makes, even once we kind of know what we're doing. Like the level of mistakes that I've made in the past 10 years is pretty incredible. So why have I achieved, you know, I would say each year I've been kind of more successful than the last.

I've had more wins than the last. I'm happier now. I make more money. Whatever measure, I've built more successful companies. I struggle less. I am less stressed. So by all measures, I would say my life has gone up into the right, and yet I've done a lot of things that haven't worked.

I've had more wins than the last. I'm happier now. I make more money. Whatever measure, I've built more successful companies. I struggle less. I am less stressed. So by all measures, I would say my life has gone up into the right, and yet I've done a lot of things that haven't worked.

And I guess this is maybe more of a personal episode than I've done in a while, but I wanted to walk through a few of those failures. You know, are they failures? I don't even want to label them. They're just things that I did that basically... kind of didn't work long term. They were decisions that I made that were a lot harder than I thought or just didn't turn out the way that I thought.

And I guess this is maybe more of a personal episode than I've done in a while, but I wanted to walk through a few of those failures. You know, are they failures? I don't even want to label them. They're just things that I did that basically... kind of didn't work long term. They were decisions that I made that were a lot harder than I thought or just didn't turn out the way that I thought.

One of them, man, going back to 2013, so this is 11 years, when we launched Trip, I had some hubris about the fact that it was going to work, that I knew what I was doing, that I'm a successful entrepreneur. It was my fifth company. Yeah, because MicroConf was fourth, TinySeeds sixth. Anyways, it's my fifth company. And I was like, you know what? I know what I'm doing.

One of them, man, going back to 2013, so this is 11 years, when we launched Trip, I had some hubris about the fact that it was going to work, that I knew what I was doing, that I'm a successful entrepreneur. It was my fifth company. Yeah, because MicroConf was fourth, TinySeeds sixth. Anyways, it's my fifth company. And I was like, you know what? I know what I'm doing.

I have a bit of money in the bank. I have some experience. I have a good network. I have an audience. I'm a product person. I've done this before. It's just going to work. And then we launched and it didn't work. And it plateaued at eight, you know, you've heard the story, plateaued at eight grand a month for months on end. And I was just distraught.

I have a bit of money in the bank. I have some experience. I have a good network. I have an audience. I'm a product person. I've done this before. It's just going to work. And then we launched and it didn't work. And it plateaued at eight, you know, you've heard the story, plateaued at eight grand a month for months on end. And I was just distraught.

And I had a moment where I was like, I'm supposed to be good at this. People listen to me about being an entrepreneur. Like, don't I know how to do this? I thought I knew what I was doing. And it turns out I figured it out, right? It was grinding. It was working with Derek to figure out the next thing to launch and how to pivot the product. And we did.

And I had a moment where I was like, I'm supposed to be good at this. People listen to me about being an entrepreneur. Like, don't I know how to do this? I thought I knew what I was doing. And it turns out I figured it out, right? It was grinding. It was working with Derek to figure out the next thing to launch and how to pivot the product. And we did.

And it took us, I don't know, maybe nine months from launch, nine agonizing months from launch to get to the point where we had product market fit and things took off like a rocket. And then it was like, okay, I do know what I'm doing. I was just overconfident that it would work right away. If you want to hear all that agony, by the way, go to Startup Stories Podcast.

And it took us, I don't know, maybe nine months from launch, nine agonizing months from launch to get to the point where we had product market fit and things took off like a rocket. And then it was like, okay, I do know what I'm doing. I was just overconfident that it would work right away. If you want to hear all that agony, by the way, go to Startup Stories Podcast.

You can look in any podcast app or you can go to startupstoriespodcast.com. Derek and I recorded like 10 to 15 minutes a week for a year. And then I cut it all to actually not all of it together.

You can look in any podcast app or you can go to startupstoriespodcast.com. Derek and I recorded like 10 to 15 minutes a week for a year. And then I cut it all to actually not all of it together.

I think it was like nine hours of audio and I cut it down to 90 minutes and kind of just packed it all in so you can hear this longitudinal agonizing trip towards product market fit as we finally did get there. But

I think it was like nine hours of audio and I cut it down to 90 minutes and kind of just packed it all in so you can hear this longitudinal agonizing trip towards product market fit as we finally did get there. But

I have a little bit of PTSD when I listen to it because it was such a hard time of not even knowing what we were building and if we were building anything for anyone and if it was all just a waste of time. So that was one, you know, like I said, 10 or 11 years ago. How about MicroConf Locals? We launched local events.

I have a little bit of PTSD when I listen to it because it was such a hard time of not even knowing what we were building and if we were building anything for anyone and if it was all just a waste of time. So that was one, you know, like I said, 10 or 11 years ago. How about MicroConf Locals? We launched local events.