Episode 850 | How Not to Screw Up When Hiring Your first Developer and More Listener Questions (with Derrick Reimer)

Rob Walling (0:00)

Welcome back to another episode of Startups For the Rest of Us. I'm Rob Walling, and in this episode, I welcome Derrick Reimer back on the show, and we answer four listener questions. We spend a good chunk of time at the top of the show covering three or four questions around hiring your first developer as a Bootstrapped founder. Then we dig in to the pitfall of building features requested by customers, just because they're easy to build, because AI makes it easy, and the dangers of doing that. Talk about getting over social anxiety as a founder, because you have to learn to market, sell, and all that. And then, at the end, touch on trademarks.

Hope you enjoy this episode. Before we dive in, if you're a founder doing more than a million of ARR, odds are pretty good that you have at least one decision, probably more, in front of you that really matter.

Things like, do you hire a sales rep or do you hire another engineer? Maybe churn is creeping up, like, do you rework your pricing? Do you rebuild onboarding? Do you take the enterprise deal with the custom SLA or do you walk away? And then you realize there's almost no one you can talk it through with. Your team is too close to it, your friends don't get it, and so much of the advice online is for people ten steps beyond you or people just getting started. So that's exactly why we host TinySummit. It's a small group of founders, all past a million in ARR, getting together for two and a half days in lovely Cancun, Mexico. And it's built around round tables and the kinds of conversations you can't get anywhere else. It's December 5th through the 7th of 2026 at one of the top resorts in Cancun. Some of the folks in the room are part of our SAS Institute coaching program. That's our year-round community for founders past a million. Ricardo Lassa of Clickin will be there. So will JD of Senior Place, Colin of Status Gator, Adam McCrea of Judo Scale, Kieran Delaney from Flat Plan. If you want to get in a room with some incredible founders to solve your toughest problems, I hope you'll join us because I'm going to be there too. I think it's going to be small, like 15 to 20 founders, so it really is a premium retreat. You can get all the details and apply to attend at tinyc.com/tinysummit.

I do think it will sell out and we are taking applications and being pretty critical about who we accept. So there is an application process I did want to let you know about. And separately, if you have a product that you want to get in front of serious SaaS founders, we're opening up sponsorships from Microconf US in Austin, April 18th through the 20th. Our last seven events have sold out and this one will too. So you're looking at a room full of, say, 250, 275 bootstrap founders with real businesses, like 32, 35% of our attendees are doing at least $100,000 in MRR.

Producer Ron is running partnerships this year and there's a great range of options, including cross promotion here on the podcast. You can email him at sponsors at microconf.com. And with that, let's welcome Derrick Reimer to the show.

Back by popular demand, it's Derrick Reimer. How you doing, man?

Derrick Reimer (3:17)

I'm doing well. How are you?

Rob Walling (3:18)

I'm good. How does it feel to be the guest that I chose to be on episode 850 of this very show?

Derrick Reimer (3:27)

That is a nice round number.

Rob Walling (3:28)

That an accolade for you? Yeah. Good.

Derrick Reimer (3:30)

Yeah.

Rob Walling (3:31)

Handpicked it, because there's a handful of guest people really, really dig and they keep asking me to bring back on. You, of course, are one of those. And today, we're going to answer listener questions. We have some really good questions today. I think we're going to dig pretty deep into them.

First one is from Michael, and he's asking about hiring his first developer.

Michael (3:59)

Hi, Rob, long time listener here. Thank you so much for your podcast. I founded an accounting sauce for Swiss freelancers four years ago, and I'm currently at around 10, 4K MRR. And I'm thinking about hiring my first developer. And I have so many questions around that. So I thought I'd ask you first of all, what qualities would you look out for the first developer you hire so that that person can actually take things off my plate and free up my time, and hopefully take ownership of the code base in the long run? Also, how do you effectively onboard someone onto a code base you've been the sole contributor to? Would you try to create some sort of documentations, or just dive into it and try to teach them on the code? And also, do you have any other tips on how I can derisk choosing the wrong person and wasting time and money, and making the onboarding process as smooth as possible, so that the person can get effective as soon as possible? Thank you so much for any inputs, and again, thank you so much for your show. I've been really enjoying it for the past four years. Every Tuesday, it's been a big part of my life. Thanks.