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Rob Walling

πŸ‘€ Speaker
4164 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

It was a one-time sale as well, $300 worth. one time with like 20% maintenance a year. And it had peaked between like 3,000 and 5,000 a month. And so in any given month, it was great. It was making my house payment plus a car payment, which I didn't have because I had big cash for the car. But you get the idea. It was just a nice side income as I worked full-time during the day.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And I really tried to grow that business. I was like, I want to get it to 10K, 12K a month so that I can quit my day job. And I spent about a year, nights and weekends, trying to do that before I realized this is a step one business. Now that term didn't exist then. I hadn't come up with the stair step method. That would be, what, seven years later maybe?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And I really tried to grow that business. I was like, I want to get it to 10K, 12K a month so that I can quit my day job. And I spent about a year, nights and weekends, trying to do that before I realized this is a step one business. Now that term didn't exist then. I hadn't come up with the stair step method. That would be, what, seven years later maybe?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

But in retrospect, it was something that I never regretted putting that time in and trying to grow it. I learned a lot during that time about what worked, what didn't work. And when I got to the point where I was out of ideas and out of motivation, then I put it on autopilot.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

But in retrospect, it was something that I never regretted putting that time in and trying to grow it. I learned a lot during that time about what worked, what didn't work. And when I got to the point where I was out of ideas and out of motivation, then I put it on autopilot.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And autopilot's not real, realize, like every 18 months, Google would slap it, a competitor would come up, something, I'd need to update the code. You know, there were all these things that would happen. But as autopilot as you can make it, and then I moved on to my next thing. And that is actually when I built out a portfolio of products.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And autopilot's not real, realize, like every 18 months, Google would slap it, a competitor would come up, something, I'd need to update the code. You know, there were all these things that would happen. But as autopilot as you can make it, and then I moved on to my next thing. And that is actually when I built out a portfolio of products.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Now with a portfolio of products, never try to grow more than one at a time. You focus on one, you get it to grow, and you get the, basically that recurring growth traffic that then builds hopefully recurring revenue and then get it to the point where it's stable and maybe you autopilot that one too.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Now with a portfolio of products, never try to grow more than one at a time. You focus on one, you get it to grow, and you get the, basically that recurring growth traffic that then builds hopefully recurring revenue and then get it to the point where it's stable and maybe you autopilot that one too.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And so I stacked a bunch of step one businesses to get myself to step two to buy out my own time, quit the day job, and then I moved on to true recurring revenue with step three. that tends to be my approach, is to try things that I think could work, that I have the motivation to do, and that I think I can learn from.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

And so I stacked a bunch of step one businesses to get myself to step two to buy out my own time, quit the day job, and then I moved on to true recurring revenue with step three. that tends to be my approach, is to try things that I think could work, that I have the motivation to do, and that I think I can learn from.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Whether they work or not, whether they fail or succeed, at least I've learned something from that. So that would tend to be the approach I would take. But you, of course, can look at your own personality and say, do I want to do that? Do I want to try to make a subscription?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Whether they work or not, whether they fail or succeed, at least I've learned something from that. So that would tend to be the approach I would take. But you, of course, can look at your own personality and say, do I want to do that? Do I want to try to make a subscription?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Or do I just want to take this amazing revenue that it's generating and use it to build that standalone SaaS or true recurring revenue? So thanks for that question, Casper. I hope it was helpful. My next question is from Benjamin Hoy on X Twitter. How do I decide whether a customer type is worth selling to or targeting?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Or do I just want to take this amazing revenue that it's generating and use it to build that standalone SaaS or true recurring revenue? So thanks for that question, Casper. I hope it was helpful. My next question is from Benjamin Hoy on X Twitter. How do I decide whether a customer type is worth selling to or targeting?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

I have consumers buying my SaaS, but also schools contacting me and occasionally small businesses. How do I decide whether targeting one or the other is worth it? In my experience, you just have to try. So first of all, there's a difference between selling to and targeting. Selling to, if they're approaching you inbound, what's the real risk there?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

I have consumers buying my SaaS, but also schools contacting me and occasionally small businesses. How do I decide whether targeting one or the other is worth it? In my experience, you just have to try. So first of all, there's a difference between selling to and targeting. Selling to, if they're approaching you inbound, what's the real risk there?

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

The risk is a school approaches you, says we want to buy it, and you say, great, it's $500 a month or $1,000 a month. Make sure that you charge enough, by the way. And if it's a school, actually charge per year. So $6,000, $12,000, $25,000 a year, whatever you're going to charge. Charge enough to make it worthwhile. And you send them this quote, and you can read Founding Sales by Pete Kazanji,

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

The risk is a school approaches you, says we want to buy it, and you say, great, it's $500 a month or $1,000 a month. Make sure that you charge enough, by the way. And if it's a school, actually charge per year. So $6,000, $12,000, $25,000 a year, whatever you're going to charge. Charge enough to make it worthwhile. And you send them this quote, and you can read Founding Sales by Pete Kazanji,

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Or you can follow Jen Abel, Matt Wolock, Steli Efti, you know, some of the sales folks in the SaaS space and learn, hey, how do I kind of navigate this? And if the school comes back and says, well, we need you to sign a big security checklist or fill out this 30-page doc to close the deal.