680: (Solo) The Thing Nobody Tells You About Building a Business Alone

6 Jul 2026 · 12 min · 6 chapters

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In short

Solo founder loneliness—how building a business alone creates isolation, hidden anxiety, and delayed decisions, plus how to close the “gap” by finding real support communities.

Guest backgrounds

This is a solo episode (no guests). Nathan Chan is the host, founder of Founder (13 years; 700+ founder interviews).

Key claims

Loneliness is normal for founders (HBR: 50% of CEOs; 1 in 3 solo founders lack someone to talk to; entrepreneurs 5–5.5x more likely than general population). Founders become “good at being alone,” which turns into a wall that blocks help. Don’t “get better at being alone”—actively close the gap between what you feel and what you show.

Notable examples

Nathan’s ad spend ROAS drop causing ~$500k loss in a month; restructuring decision delayed due to inability to discuss; first hire arriving late for 18 months because he avoided conflict; early belief from partner that his idea couldn’t work. He also cites private answers from Steve Huffman (Reddit) and Joe Gebbia (Airbnb) that “it’s never enough.”

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 Loneliness of Foundership

1:44 to 2:59

Exploring the isolation felt by solo founders and the emotional weight of their journey.

“It's this feeling of like how lonely this journey is and how completely isolated you can be in a way that's hard to even put into words.”

Personal Experiences of Isolation

2:59 to 4:23

Nathan shares personal stories of struggling with loneliness and leadership pressures.

“Like when it comes to building a successful business or any business in general as a founder, the highs are high and the lows are low.”

Admitting Vulnerability

4:23 to 6:43

Discussing the difficulty of admitting struggles and the importance of seeking support.

“So a Harvard Business Review study found that 50 % of CEOs report feeling lonely in their role and one in three founders that have no one to talk to about the hardest parts of the job.”

Moments of Loss and Reflection

6:43 to 9:08

Reflecting on a friend's death and its impact on Nathan's perspective on life and business.

“And guys, when I built Founder from the ground up, I had no experience in how to run a business whatsoever.”

Building Connections to Combat Loneliness

9:08 to 10:59

The importance of finding a community and how it can help mitigate feelings of isolation.

“that felt like losing a kind of safety net I didn't know I had.”

Building Connections to Combat Loneliness

11:18 to 11:39

The importance of finding a community and how it can help mitigate feelings of isolation.

“And we have open and honest conversations around how to scale your brand.”
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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.

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1:03Welcome back to another episode of the Founder to Founder solo podcast episodes. This is where I go deep on a topic sharing everything I've learned from building founder for the past 13 years. So today I want to talk about something that doesn't come up much in business content. And I don't want to be a downer when I talk about this, guys, but this is part of the problem because when you're experiencing it the silence around it really makes you think that something's wrong with you because here's the thing right guys running a business is lonely and usually not in the way that people expect hear the stories learn the proven methods and

1:37Nathan Chan:accelerate your growth and future through entrepreneurship welcome to the founder podcast with nathan chan so i've interviewed over 700 founders on this show now over 100 of them are billionaires people running companies with hundreds or thousands or tens of employees back-to-back calls all day high energy surrounded by people that need you and when i asked them privately off the mic after recording stops so many described the same thing especially solo founders like if you're a solo founder, you don't have a co-founder. It's this feeling of like how lonely this journey is and how completely isolated you can be in a way that's hard to even put into words.

2:25And when it comes to loneliness, I'm talking about not being physically alone. It's about carrying that weight that you can't put down and you just can't hand it to anyone else. Like how scary is it for those of you listening where, you know, and every single founder has been through this, where you're just like, I don't even know if I'm going to make payroll. And it's just this massive like, oh my God, like what am I going to do? And I want to be honest with you guys today because I felt it more than once in my journey. And I wish someone told me earlier that this is completely normal. And unfortunately it's a rite of passage.

3:01Like when it comes to building a successful business or any business in general as a founder, the highs are high and the lows are low. And there was a period, I've never talked about this really publicly before, where found it almost broke me we're spending a million dollars a month on facebook ads and our returns were strong we're scaling up big time covid education it was really rocking and everything was working and then almost like overnight our you know return on ad spend just dropped and we lost end up losing like half a million dollars in a single month and i didn't even know what to do like I remember literally crying I was so lost and I was sitting there thinking like how the hell am I going to get out of this like I felt like I was at rock bottom and I was in the bottom of this well all darkness no light above you and it's hard to talk about these things publicly right and the loneliest moment wasn't the loss itself it was walking into the office the next morning getting on calls, showing up for the team.

4:02Because as a leader, they're looking to you to be the steady one. Like they need you to be grounded and clear. And unfortunately, I had no one to share this journey with. And I had to be that person that privately I was carrying something that felt like it might end. And I was able to get through it. And I want to talk to you how I've been able to get through these kinds of things. But let's dive into this gap. So a Harvard Business Review study found that 50 % of CEOs report feeling lonely in their role and one in three founders that have no one to talk to about the hardest parts of the job. And researchers have found that entrepreneurs are five and five and a half times likely to experience loneliness than the general population.

4:43And these numbers really stayed with me, right? Like, honestly, I think the real number is probably higher. Founders who are struggling the most are usually the ones that are the last to say anything because admitting it feels like a weakness. And if there's one thing that founders are trained to do it's not to show weakness it's everything has to look perfect on social media everything has to look amazing you're like worried about what other people think and you've got that fear of judgment i never forget when i interviewed scooter braun he once said he said to me like on the outside it can look like you're absolutely killing it and then you know on the inside and what really is going on people would just have no idea whatsoever how much you were struggling.

5:24And I've spoken to a lot of founders and it's not obvious, right? But when things get difficult, you can't walk into a team meeting and say, hey, I'm not sure our strategy is working or I'm worried about cash because you don't want to scare people, right? I'm not sure we can make payroll in three months. You can't do that. And people are counting on you to lead. So you carry it all alone. And I remember sitting like on a decision to do a restructure. You know, people whose livelihoods depended on their job that I gave them. And I couldn't talk it through with anyone on my team because the people most affected were the last people I could be honest with.

5:58So I'd sit with it for weeks. And that cost me, right? That cost me hundreds and hundreds of thousands of dollars. And I think when you let it sit with you, when you're going through challenging times and you don't act, oftentimes it ends up biting you, right? And then there's, you know, the one that really got me. Like I remember my first hire for founder, he showed up at like 2 p.m., 3 p.m. sometimes when we were supposed to start at 9 a.m. And for like 18 months, I let it happen because I hated conflict. And I couldn't bring myself to have this conversation. And the loneliest part of it wasn't the conflict or the avoidance.

6:37it was that I had nobody to call and say like, am I doing this right? Is this normal? What would you do? There was no playbook. And guys, when I built Founder from the ground up, I had no experience in how to run a business whatsoever. I was working in IT support. I never got exposed to any kind of playbook for running, growing and scaling a business. So I was just figuring it out completely on my own. And when family and friends are asking you like, how's it all going? You know, you say it's great because they're proud of you. They see the launch, they see the press, They see the milestones you posted about, but they don't see like the anxiety and you love them too much to bring them into it.

7:13They won't understand. So you keep that private. And I remember early on when I started founder, I was working my idea support job. And during the day I would, you know, work my nine to five and then build a magazine at night. And I remember even asking my partner at the time, like, do you think I could build this into actually something? And she said, no. And she wasn't being cruel. She was just being honest based on what she could see. But in that moment, I had nobody who believed in what I was building, nobody who could see what I could see. And that's a very specific kind of alone. So sometimes the wins just feel just as isolating as the hard moments.

7:47And you know, you hit a revenue number you've been chasing for two years and the person you most want to celebrate is someone who's been in that same fight, but your family's happy for you, but they don't really understand what it took. Your friends say congrats, but you don't feel it the way another founder would. So that's why, you know, if I was to start another business, I would probably have a co-founder, which is crazy, right? It's crazy. So let me talk about what changed for me. So about now, eight years ago, my best friend, Aaron, who I went to kindergarten, primary school, high school, university, we traveled all around Europe together.

8:26He passed away before he really got to live his thirties and forties. before he got to do the things that you're supposed to do. And losing him, like I'd never been around death before, I really understood how short life is. And, you know, I'm speaking to you guys right now and I've got a photo of him from his funeral on my shelf. And I try and think of him when sometimes I feel alone. I try and think of him when business is tough. I try and think of him when I think, oh my God, he would have absolutely done anything to be in the position I'm in right now. And before the interviews and the team and the brand, he knew a version of me that was just figuring things out.

9:07And when he was gone, that felt like losing a kind of safety net I didn't know I had. And after Aaron died, I started to pay more attention to the conversations I was having with founders in private, not on the podcast, but even during the recording or after the recording. And I started to ask different questions. Like I remember I asked Steve Huffman, the founder of Reddit, a guy who never has to work another day in his life. I said, is it ever enough? And he said, no. I asked Joe Jebbia, the co-founder of Airbnb. I asked him the same question, same answer. And I realized the same thing. This drive that we all have as founders, it never turns off, which can feel like a gift and a prison at the same time because the people around you don't always understand it and they don't understand why you can't be satisfied.

9:51But that obsession is what got you there in the first place. so here's what i've learned as we work towards wrapping up and this took me a long time to figure this out is the most dangerous thing about founder loneliness isn't loneliness itself is that you get good at it you get practiced at carrying these things alone you build a tolerance for it you develop this skill showing up calm saying the right things projecting confidence while privately sitting with something heavy and that skill keeps you functioning it's how you survive the hard lessons but here's the trap that same skill the one that keeps you standing it becomes a wall and over time that wall doesn't just keep out the hard stuff it keeps out the people who could actually help your partner your friends other founders who have been exactly where you are and this is the one thing i want you to take away from this episode stop getting better at being alone the gap between what you're actually feeling and what you let anyone else see that gap will keep growing unless you actively close it.

10:53And the only one to close it is to find people, be surrounded by communities of people that are in a similar situation as you. One of the fastest ways to grow your business is to meet people and hang out with people that have already done it a few steps ahead of you. One of the fastest ways to work through this loneliness is to hang out with like-minded people regularly. And that's exactly why we built Founder Operators. It's our community for e-com founders that are scaling. And we have open and honest conversations around how to scale your brand. We've got three in-person events a year. We're really passionate about what we're building.

11:29This is an incredible D2C community. So if you are looking to find your tribe, check out Founder Operators. We've got a link in the show notes. You go to founder.com forward slash operators. And either way, find a local community. make sure you're hanging out with other founders that are at a similar level to you a little bit always ahead of you but then also a couple behind you because it's great to be able to teach and give back and that's where you can get so much more from this journey anyways guys this is a totally different episode a little bit deeper than usual i hope you found it somewhat interesting i hope it resonated in some way shape or form send it to another founder who needs to hear it and And shoot me a DM.

12:10We'd love to hear from you on Insta, at Nathan Chan. And I'll see you in the next one.

From the publisher

After interviewing over 700 founders, including more than 100 billionaires, I kept noticing something that never made it onto the podcast. When the recording stopped and I asked privately how they were really doing, so many described the same thing. The weight of carrying something you cannot put down and cannot hand to anyone else.

Here is the truth I wish someone had told me earlier: entrepreneurs are five and a half times more likely to experience loneliness than the general population. And the founders who are struggling the most are almost always the last ones to say anything about it.

In this episode, I share things I have never talked about publicly before, including losing half a million dollars in a single month, showing up for my team the next morning like nothing happened, and what losing my best friend Aaron taught me about what actually matters on this journey.

Here's what you'll take away:

Why founder loneliness is not about being physically alone, and why that distinction makes it so much harder to recognise and address

The moment that almost broke me at Foundr, and what it actually felt like to carry it without anyone to call

Why the skill of showing up calm and projecting confidence eventually becomes a wall that keeps out the people who could actually help

What Scooter Braun, Steve Huffman, and the co-founder of Airbnb all said privately about whether it ever feels like enough

Why the wins can feel just as isolating as the hard moments, and what to do about that

The one thing that has made the biggest difference: surrounding yourself with founders who are a few steps ahead of where you are right now

If you have been carrying something heavy lately and telling everyone it is fine, this episode is for you. The gap between what you are actually feeling and what you let anyone see will keep growing unless you actively close it.

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.

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