678: (Solo) The First Hire Mistake That Trips Up Almost Every Solo Founder

29 Jun 2026 · 10 min · 5 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Solo founder’s first hire mistake—hiring reactively or too broadly (e.g., “assistant doing 101 things”), leading to low quality, unclear outcomes, lost trust, and burnout; instead, hire for what only the founder can’t do, define measurable outcomes, and start with AI agents/automation or freelancers before a full-time hire.

Guest backgrounds

Solo episode; no guests.

Key claims

Don’t hire tasks—hire outcomes. If you can do it yourself, you’re not getting leverage unless the hire is better. Trust is earned over time, especially if you “give the keys.” Start with agents for support/email flows/ops, then freelancers (e.g., Upwork), then human hire.

Notable examples

Nathan describes a past hire where he gave too much too fast and the person didn’t earn trust; he contrasts broad “all-rounder” roles with focused roles tied to measurable results.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Overwhelm of Doing Everything

2:09 to 3:19

Explore the challenges solo founders face when trying to manage every aspect of their business.

“You're doing B2B sales, wholesaling your product.”

The Mistakes of Reactive Hiring

3:21 to 4:46

Understand the pitfalls of hiring too quickly or too broadly without clear expectations.

“And everything else is what you hire for.”

The Importance of Trust and Outcomes

4:48 to 6:15

Learn why hiring for skill and building trust over time is essential for success.

“A lot of founders also wait too long to hire, not because they can't afford it, but because letting go is genuinely hard.”

Strategies for Hiring and Freelancing

6:16 to 8:24

Explore effective strategies for hiring, including freelancers and test projects.

“So I'll give you an example of a hire where I never forget.”

Key Takeaways for Solo Founders

8:29 to 9:09

Reflect on the crucial decisions solo founders must make regarding their first hire.

“you'll make as a solo founder to get leverage and buy back your time.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:01Hey founder fam, before we jump in, I want to take a quick moment to talk about our sponsor OmniSend, the email marketing and SMS platform built specifically for e-commerce founders. We've been recommending OmniSend to founder students and members of our platform for a while now because it just works. So whether you're launching your first store or you're scaling it to seven figures, it really helps you automate your marketing and get results. And did you know, on average, OmniSend customers make$79 for every$1 they spend, which is an insanely good return on investment. And if you're already on another platform, here's the thing.

0:35In just five days, you could actually be paying 35 % less without doing an absolute thing. OmniSend will move every flow across, list, and template. You just show up when it's done. And finally, because you're part of the founder community, you get 50 % off your first three months with the code FOUNDER50. Just head to omnisend.com forward slash founder and that's founder without the E to get started. All right, now let's jump in the show. Hey guys, Nathan here. Welcome back to another solo episode, Founder to Founder podcast. And today I want to talk about one of the biggest decisions a solo founder faces.

1:15And it's one that I think a lot of people get wrong. And we work with a lot of members in our Founder Plus community, with our founder operators community. And it's something that comes up a lot. Like, hey, I'm overwhelmed. I want more help. I want to make my first hire. Who to hire? When to hire? And I think it's something that a lot of founders get wrong because they either move too fast and they hire reactively or they wait too long and burn themselves out and do everything alone. And then we've got this new kind of revolutionary thing that is rocking our world right now. I think it's safe to say that agentic AI agents, AI employees is really here now.

1:53Nathan Chan:Hear the stories, learn the proven methods, and accelerate your growth and future through entrepreneurship. Welcome to the Founder Podcast with Nathan Chan.

2:07Here's what I see most often. A founder's doing everything. You're doing B2B sales, wholesaling your product. You're doing marketing. You're doing operations. you're doing customer service, you're doing ad creative, you're doing social content, and you just stretch real thin. And you feel overwhelmed, frustrated, and exhausted. So you're like, I just want to hire somebody to take care of all the stuff that I don't want to do. And without the least amount of involvement that is required, they can just take care of it. And you hire reactively, you bring in somebody to take the pressure off right now without really thinking about what that business actually needs and the result is that you get really frustrated because after a month or so it's really you know the first few weeks it's exciting then after a month or so you kind of start to see some cracks and it's just like oh i'm really frustrated and the quality of the work's not there and then you feel like you're getting having to get involved and then you lose trust and then it's harder to delegate and then you find yourself kind of in this rock in a in a hard place a few months later and just like oh my god like this person is not working out and I've made this mistake countless times I've watched a lot of other founders make it too so before you hire anyone I want to go through some principles and concepts that have really helped me then this is you know whether it's your first hire your 10th hire your 50th hire that I think really helps so I think you first and foremost need to work out what is the thing that only you can do in the business and what is the thing that gives you the most energy And whatever those answers are, that's what you should be spending your time on.

3:46And everything else is what you hire for. So if you're the best person in your business doing the social media content and creating founder-led content and product development, then that's what you should be doing. Hire for operations, perhaps. So if you're a product person, stay close to the product. Hire for marketing or customer experience. the mistake that most founders make is they hire more of what they're already doing or they choose this kind of broad kind of role especially your first hire as an e-com founder they hire this broad kind of role of like i want an assistant and they're going to do 101 different things and these are the things that i don't want to do and it's overwhelming me but then it's really tough because the quality work is not there or the expectations aren't set correctly and then there's no clear measurable outcomes and it's not clear what success looks like.

4:37So when that person came on, it wasn't really clear or sold to them exactly what they're going to be doing. And then they're kind of an all-rounder and it just becomes a real mess. And this is the part that I don't think gets talked about enough. A lot of founders also wait too long to hire, not because they can't afford it, but because letting go is genuinely hard. When you've built something from scratch, it's your baby. Every part of the business is personal. You have things that you want done a certain way you have a standard in your head and you unconsciously expect that person to know that standard and the idea of handing something over to someone else is hard right it's uncomfortable even when you know it's the right thing but the truth is and this is something that i had to learn the hard way i found it if you are hiring someone to do a job that you could do yourself you are not getting the most out of that hire because the goal is to find someone who is genuinely better at that skill than you are.

5:33And if they are, that is awesome. Even if, you know what, even if they do it 75%, 80 % as good as you, that's a win, right? I think depends on the actual thing that you're getting them to do, but you know, you want to focus on outcomes, not tasks. I was speaking to one of our members the other week and I really kind of rocked the world kind of going, hey, like, let's not focus on tasks. These are all the things you need this person to do. What are the outcomes and how can we measure those outcomes? Because I know that these people, everyone wants to succeed. Anyone in your business, anyone you're hiring, they want to succeed.

6:10They want to do a good job. So how can you measure that? How can you show them? They want to win. They want to succeed. They want to grow. And that's what leaders do. So I'll give you an example of a hire where I never forget. It was a tough one where basically I hired for a role that I really thought I'm just going to let this person in and I gave too much too fast and they didn't earn the trust from me. And I think that's something that has to be earned over time. When you give people the keys to the kingdom, it's going to be done over time. And so that's just something I can't stress enough.

6:53It's a fine balance, but the trust is earned, not given. So there's also the timing question as well. And that's changed a lot because as I shared, you can use AI agents to do customer support, email flows, a lot of your operations. So for a solo founder who isn't generating enough revenue to justify a full-time salary, my recommendation is start with agents and automation, but then also freelancers. Freelancers are amazing. When I first started Founder, I used Upwork. I found some incredible freelancers. I started super lean. You can find some incredible talent on Upwork. It is such an incredible platform.

7:35And just so you guys know, they are not sponsoring this podcast. It's a good product and it's a great place to find incredible people. Now, when you are ready to make your first human hire, one thing that I will also share is you want to hire for attitude. Always, always, always, always, always hire for attitude. before skill the test project that you use with that person is critical create a test project before you hire them get a feel for their work and make the test project something that is actually naturally in line for what they'll actually be doing in the role so you get a real feel for it but i'm a big fan of part-time contractors freelancers first right step you never know a lot of the freelancers it's a way to try before you buy and a lot of um our freelancers that we've hired at founder and being, you know, eventually full-time team members and are some of the best.

8:28So, you know, the big takeaway for today is your first hire is one of the most important decisions you'll make as a solo founder to get leverage and buy back your time. And it's the decision that it's not about who or when, it's about whether you are losing money by doing these things. and it's about asking yourself the question, how can you buy back time and whether you're losing money or not with all the different things that you are doing and you wanna portion out the things that will help you keep optimizing for marketing, sales and products. You wanna be spending at least 80 % of your time on marketing, sales and product as a founder.

9:09All right, so that's where the real growth starts. All right, guys, I hope you enjoyed this episode. i hope this really helped you think through team structures where you're at with your business and as always would love to hear feedback if you could leave us a review spotify apple podcast wherever you're at wherever you're listening that would mean a lot and then share this with a friend share this podcast with a friend we work so hard to create just the most awesome informative podcast to help you start grow and scale your e-commerce brand so thank you for listening if you could share with a friend it would mean the world to us this podcast is 100 free we're here to help however we can i'll see you in the next one

From the publisher

Most founders make their first hire reactively. They're overwhelmed, stretched across every function, and they just want someone to take the pressure off right now. So they bring in a generalist, hand them a list of everything they hate doing, and a few months later they're more frustrated than before.

Here's the problem: hiring to relieve pressure is not the same as hiring strategically. And when you get it wrong early, it doesn't just cost you money. It costs you trust in the whole process of building a team.

In this episode, I walk through the framework I wish I had when I made my first hire at Foundr, including the question that reframes the whole decision, why attitude always beats skill, and how to use freelancers and AI agents to buy back time before you are ready to bring on a full time team member.

Here's what you'll take away:

• Why hiring reactively is the most common and most expensive mistake solo founders make
• How to identify what only you can do in the business, and why that answer should drive every hiring decision
• Why focusing on outcomes instead of tasks completely changes how you set a new hire up to succeed
• The case for starting with freelancers and AI agents before committing to a full time salary
• How to run a test project that actually tells you whether someone is the right fit before you sign them on
• Why trust is earned over time and what happens when you hand over too much too fast

If you are doing everything yourself right now and wondering whether it is time to bring someone on, this episode will give you a clear framework for making that call and help you avoid the mistakes that set most first hires up to fail.

If you're loving this solo series, I'd love to hear your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it.

WANT TO GROW YOUR BRAND WITH META ADS?
Join the Foundr Operators Waitlist → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://foundr.com/operators⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER

Learn directly from 7, 8 & 9-figure founders inside Foundr+

Start your $1 trial → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.foundr.com/startdollartrial⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING?

→ Starting from scratch? Apply here → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-start-application⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

→ Already have a store? Apply here → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-growth-application⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

CONNECT WITH NATHAN CHAN

Instagram → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/nathanchan⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

LinkedIn → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/nathanhchan/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES

YouTube → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/2uyvzdt⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Website → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.foundr.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Instagram → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/foundr/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Facebook → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/foundr⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Twitter → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.twitter.com/foundr⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

LinkedIn → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/foundr/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Podcast → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.foundr.com/podcast⁠

More from The Foundr Podcast with Nathan Chan

All 259 episodes
678: (Solo) The First Hire Mistake That Trips Up Almost Every Solo FounderThe Foundr Podcast with Nathan Chan · 10 min
Listen in VO