Story Context

Industry: B2B SaaS (vertical-specific CRM)
Funding: Bootstrapped
Team Size: 1 full-time employee (me), 2 part-time contractors
Founder Type: Solo founder
Work Setup: Remote

The Confessional

Where were you in the journey when this happened?
Year two. I was doing about $7K MRR, mostly through outbound. I had a small customer base, decent retention, and a never-ending to-do list. I wasn’t failing. But I wasn’t growing fast either. I was in that quiet, gray middle — not broke, not funded, just grinding.

What was the challenge or low point you faced?
I didn’t realize how lonely I was until I found myself talking out loud to nobody. I’d build a new feature, push it live, and sit back waiting for… nothing. No Slack channel. No “nice work!” Just me, refreshing Intercom to see if anyone noticed. I had no one to share wins with. No one to gut-check ideas. No one to ask, “Am I overthinking this?” Every decision — pricing, roadmap, copy, hiring — felt like shouting into a void.

What did it feel like on a day-to-day level?
Like I was slowly losing emotional range. I wasn’t happy or sad — just flat. The business became a mechanical process. I shipped. I supported. I sold. Repeat. And even though I technically talked to people every day — customers, a designer, a part-time VA — none of them were in it with me. Sometimes I’d rewrite a landing page headline five times, not because it mattered, but because I just wanted someone to say, “Yeah, that’s the one.”

Was there a moment that made you realize it had to change?
Yeah. I took a weekend trip to visit an old friend. On the last night, we were walking back from dinner and I started talking about the business — casually, nothing heavy — and she stopped me and said, “You seem really alone in this.” It caught me off guard. But she was right.

What did you do to address it? What helped?
I joined a tiny founder circle. Not one of the big Slack groups. Just a DM group of five solo founders introduced by a friend. We do a 45-minute call once a week — no agenda, just check-ins. I also started writing short voice notes to myself each night. Not productivity stuff — just thoughts, feelings, whatever was rattling around. That helped more than I expected. It gave me some emotional closure at the end of each day.

Where are things now?
Still solo. Still remote. Still bootstrapped. But now I feel held. If I’m debating a pricing change or doubting a roadmap move, I have people who get it. I’m not looking for advice most days — I just want someone to nod and say, “Yeah, I’ve been there too.”

What do you wish you had done differently?
I underestimated how much emotional support I’d need. Not for the big things — but for the boring, daily weight of building alone. Being a solo founder doesn’t mean you have to be isolated. But no one’s going to fix that for you. You have to build your own support system — just like you built your product.

Want to share your story?
Every week, we publish an anonymous story from a real founder — not about the headlines, but about the hard stuff: burnout, co-founder tension, financial stress, team struggles, and everything in between. If you’ve been through something other founders could learn from — or even just relate to — we’d love to hear it. We keep it 100% anonymous. You can write it yourself or use our interview script and we’ll shape it into a story with you.

Reply to this email to get started.
You’re not alone in this. And your story might help someone else feel a little less alone too.