Episode 850 | How Not to Screw Up When Hiring Your first Developer and More Listener Questions (with Derrick Reimer)
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What is the episode’s overall focus and who are the hosts?
Welcome back to another episode of Startup for the Rest of Us. I'm Rob Walling, and in this episode, I welcome Derek 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 into 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 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's too close to it, your friends don't get it. And so much of the advice online is for people 10 steps beyond you or people just getting started. So that's exactly Exactly why we host Tiny Summit. 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 roundtables 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 Lasa of Clickin will be there. So will JD of Senior Place, Colin of Statusgator, Adam McCrea of Judoscale, Kieran Delaney from Flat Plan. If you wanna get in a room with some incredible founders to solve your toughest problems, I hope you'll join us because I'm gonna be there too. And I think it's gonna be small, like 15 to 20 founders.
What qualities should a bootstrapped founder look for when hiring their first developer?
So it's really is a premium retreat. You can get all the details and apply to attend at tinyseed.com/slash tiny summit. 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 Sirius SaaS founders, we're opening up sponsorships from Microconf US in Austin, April 18th through the 20th. 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 microcom.com. And with that, let's welcome Derek Reimer to the show.
Backed by popular demand, it's Derek Grimer. How you doing man?
I'm doing well. How are you?
I'm good. How does it feel to be the guest that I chose to be on episode eight hundred and fifty of this very
show? That is a nice round number. Is that an accolade
for you? Yeah, good. Yeah. Hand picked it. Cause you know, there's a handful of guests people really, really dig, and they keep asking me to bring back on. You, of course, are one of those. And today we're gonna answer listener questions. We have some really good questions today. I think we're gonna dig pretty deep into them. First one is from Michael, and he's asking about hiring his first developer.
Hi Rob, long time listener here. Thank you so much for your podcast. I found an accounting sauce for Swiss freelancers four years ago and I'm currently at around twenty four KMR 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 in 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?
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Chapters
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2 identifiedMore from Startups For the Rest of Us
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