[scubakid]

Thanks. For a while there, it wasn't clear to me which side of the line I was walking.

Something that stuck with me from Poor Charlie’s Almanack is that low expectations are a cornerstone of a happy life. I built this for myself first, so when people actually signed up and paid, it was incredibly motivating. I was thrilled to spend my free time treating those early customers like royalty and building more of what they wanted.

If I had instead come into this with the expectation of quick success, I doubt I would have made it through those early years.

And cheers from one bootstrapper to another. It's not easy, but I can't imagine a more rewarding way to build.

[chatmasta]

Another lesson here: you built for a specific community who is passionate, money-motivated, and concentrates in specific social spaces (forums, reddit, etc.) where you can promote your business. This isn't always a recipe for success, but it's a damn good starting point. You need to adjust to the sensitivities of the community to avoid overly self-promotional content, but you always have a clear channel to promote your very specific product that meets their needs.

[cloverpari8]

More importantly, the site looks pristine, with soft, artsy, techie, nature images with calming, strong, and welcoming colors and vibes, and and follows what at least used to be good SEO practices with a blog that is kept up to date frequently enough, etc.

If you don’t know a good site, you’ll never be able to develop one or pay for one without using a ok template.

[8f2ab37a-ed6c]

It’s very much what Sahil Lavingia recommends doing in The Minimalist Entrepreneur

[katzgrau]

+1 from someone who also bootstrapped a side project into a 7 figure business, and just happens to be absorbing some lessons from Poor Charlie’s Almanac on Audible recently.

[scubakid]

ha I listened on Audible too. great audiobook for a walk after dinner. Charlie's advice really holds up. which part have you gotten the most out of so far?

also, congrats!

[speleding]

Congrats. A word of warning: I scaled my SaaS site to $1M in AAR in a few years, but then a lot of competition appeared and a decade later it's still at only $1.5M. I have a good time running it and I can live comfortably while feeding my team, but with my initial success I had hoped it would go up further faster. So keep those expectation low, the next million may not come as easily as the first.

[scubakid]

Knowing what you know now, is there anything strategic you would have done differently after reaching that 1M ARR milestone?

[speleding]

Good question. The main problem I had was being too slow scaling up from 1 person. Building a good team is tricky, it's very hard to convince great devs to join you when you are by yourself at a time when they had a pick of jobs from FAANG. Even if you can match the salary of well funded startups, other companies can offer working with a larger team.

So you have three options: 1. hire sub-par people, 2. get VC funding to hire an entire team, or 3. continue doing most stuff by yourself.

I tried hiring sub-par people. That was a mistake, they took way more effort and negative energy than I got in return from the salary I paid them. I did not want to take on VC funding to be able create a large team at once, and in hindsight I think that was a good idea because several of my competitors did, and then had to fold 5 years later when they ran out of funding and their revenue was not high enough. (Also, the freedom of being a 100% owner and not having anyone tell you what to do was a major quality of life improvement for me that I never want to give up again once I tasted it. I hope you savor it as I do!)

So being smarter about hiring is what I would do differently, but that's easier said than done. I think the job market today probably does have more high quality devs available that don't mind being employee number two.

Edit: to add, once competitors appeared it became much more of a marketing game than a web dev game, because customers just tend to click the first three google hits. Getting good at marketing, and hiring the right people for that, is a whole other ballgame if you're a dev.

[scubakid]

I think there's a certain type of engineer that actively prefers working in a small team where you can make an outsized impact and wear many hats. I'm one of them lol.

I wonder if you could bring on just one really good dev who matches that description vs scaling up to a larger team. In many cases, a very small team of A+ players can beat a large team of B players.

Although it sounds like you're saying marketing/distribution may have played a larger role in your trajectory? In hindsight, do you think focusing your team-building efforts on the marketing side would have been a better strategy?

[speleding]

Yes, I agree, one or two good engineers should easily be enough, and preferable to a large team. In between having programmers on staff I ended up doing most of it myself. It was not for want of trying, but even getting someone to apply is hard when good engineers were getting dozens of emails and calls from recruiters a week (back then). In the end, doing too much things by myself caused my company to be a bit slower with design updates, not enough attention to marketing, etc. And although there are way more people available who claim they can do marketing, finding a good one turned out to be just as hard. But some things, like well-funded competitors appearing that outspend you on Google Ads, are not under your control. I'm still happy with the end-result though, it's a great life style business.