From Side-Project to Full-Time: 5 Things I've Learned in 5 Years

Tuesday, September 28th 2021

1) Don't Quit Too Hastily

If I had followed the popular advice of the Twitter talking heads, I would have quit a long time ago. New founders quit good ideas way too often, way too early. If you're a first time founder, you don't know ~~everything~~ anything. For all you know, the reason that your business isn't growing is because you're doing something wrong, not because the idea is necessarily bad or unprofitable.

I went nearly 1 year without a paying customer. I should have quit, had I followed the advice of those ahead of me. But I didn't. Again — you don't know everything. Allow yourself to improve in the areas that may be holding your growth back. So before you give up, make sure that you're not giving up on a good idea simply because you suck at marketing it to the right audience.

There have been times where I wanted to quit. Many times. It happens. But I knew my idea didn't suck, and so I stuck with it. There are no shortcuts.

You are not going to be the next talking head on Twitter that launches an overnight success to $20k MRR. Stop expecting to be.

2) Don't Waste Your Time

As a startup founder, there are a lot of ways to waste your time. Like launching on Product Hunt. Or Indie Hackers. Or Hacker News. Or posting your business on the myriad of "startup list" websites. These are, largely, colossal wastes of your time unless your business is in the small minority of businesses whose target market jives with these audiences. Just because you sell an API like we do doesn't mean that all programmers are your target market. Us programmers don't like buying things, but our bosses do.

And even if you hit it big on these sites, they are unlikely to convert into paying customers, especially for B2B products. These individuals, "tire kickers" as I call them, want free, free, free and nothing else. They can do what you did, but in a weekend, after all. And their attention spans will go to the next thing before you can even get their feedback (aside: prioritize feedback from paying customers).

How do I know?

Because I got to the front page of HN ~~twice~~ three times, got product of the day on PH, and had multiple interviews on IH. All these channels ultimately do is serve as dopamine boosters. And dopamine doesn't pay the bills, sadly. These can be good marketing channels, don't get me wrong, but how they're used by new founders in particular, where they blast their new idea to the world hoping the entire world would flock to them otherwise they'll hastily give up, is wrong.

I wasted a lot of time and money ~~spamming~~ marketing my business onto the wrong audience in the beginning. Don't do that. Your time and money would be better spent on ads, content and other, real, marketing efforts. There are no shortcuts.

(Some "time-wasters" are good, though — like instead of working, watching DrDisrespect no-scope a player out of a helicopter in Warzone. But I like to call that "decompressing.")

3) Know What You Want

Do you want to build a lifestyle business? Do you want to grow into a company with employees? Do you want funding? An exit? You should figure these things out. I decided years ago that I wanted to do this solo for as long as I could because I had been burned by business partners in the past. I don't want the overhead of having employees right now. These types of decisions have a direct effect on other decisions you'll make later on, from new customers to growth strategies to product dev to your target market.

For example, there are features that I refuse to add because they'll attract a part of the market that I don't want to be a part of, because of the effect it would have on the business. Positive effect monetarily, perhaps, but a negative effect on how much I enjoy my work. I started my business to enjoy my work. I do have some customers in that market, but they overcame the intentional friction that I refuse to remove. Not all of them want to overcome it, and that's okay with me.

Ever since my daughter was born, my priorities shifted. I no longer work nights and weekends, given I can help it (i.e. outages or severe problems). One time, I sat down in my office chair on a weekend and my 2 year old said "no working, not today?", visibly hurt that I did so. I was only watching her play with my tools, I had no intention of working, but she thought I was working. For weeks, she said this anytime I was working. When I get off, she happily shouts "alllll done working!"

I say all of that to illustrate how little I work after-hours, or at least how I try my best not to, because I've spent years on building a business that let's me prioritize being able to do so. (And also to show that kids have a way of tugging at your heart strings.)

My family is my main focus, not my business.

They overlap — absolutely — I can't provide for my family without the business. But I'd never sacrifice my family for the business. And I have a son on the way, so I foresee my priorities continuing to shift. I'd like to continue on the journey to becoming more self-sustaining, in more ways than monetarily. Buy some land, ya know, the old programmer joke about leaving tech and buying a farm. (I don't think I'd ever leave tech, but I already have chickens and a garden, so there's that.)

Sometimes, do I wish I had a co-founder? Absolutely. That's one thing that has changed about my "wants" in the last year or so — I originally wanted to do it all alone, but when the business bogs me down, or I get tired of answering support emails, or I can't figure out what to do next for marketing, I really do wish that I had a co-founder to help. I've had my eyes peeled for a good marketing co-founder, but no luck yet. *hint hint*

These are the things I want. Will they change over time? Absolutely they will. Will I always be solo? Maybe, but I kind of doubt it. I've already hired contractors to help in places where I've felt overextended. I think I'll end up hiring full-time eventually, or bringing on a co-founder. Like I said, priorities shift, life shifts.

4) Don't Let Anyone Overpay You

I've had talks of potential deals upwards of $100k/yr. These are large enterprises — F100s, F500s, F1000s. Typically, they're replacing a legacy licensing system. Some of these big deals are even with [overly] ambitious startup founders with lots and lots of funding. But I came to the conclusion some time ago that these deals largely aren't in my best interest. And I'm not the only one who thinks this way.

These deals can be hefty sums of money, sure, and they can be hard to turn down. But the leverage it gives to these customers is too extreme for my tastes. They would become too big of a piece of my "revenue pie." And typically, as part of a deal's contingency, they would request new features that wouldn't directly benefit my other customers, isolated datastores, isolated instances, custom authentication rules, etc. These things would slow down my very fast iteration and development cycles, and would ultimately become a nightmare to manage and maintain. I run a SaaS, after all, not a consultancy.

I've seen what the demands of large businesses do to a smaller business, and I didn't want any part of that. Not at this point in my life, anyways.

These deals also rarely came to fruition. I would spend hours and hours on calls, filling out questionnaires, talking to security teams, talking to engineering teams, talking to legal, all for naught. The vast majority of deals wouldn't close. I admit, this one's probably on me — I hate everything about enterprise sales (and sales in general). But I didn't want to hire a sales person just to handle these big accounts. It's too much for me, and I decided it's not the type of business I want to build.

I don't want to spend my days on calls, filling out forms, or reading long multi-page emails discussing requirements, and then responding with my own long multi-page email. It's exhausting. If I never have to read another security questionnaire again, I'd be happy. All of that's not for me, and that's okay.

I don't want to build a business that I dislike building. Again, it comes back to 3) you need to figure out what you want.

So I sort of commandeered Basecamp's mantra:

"If you're a big company with special demands, I don't want your money."

So, I turn those companies away if they aren't interested in my standard tiers. Some have continued, some haven't. Not everybody will be a good fit.

Will I regret this? No.

5) Put Your Family First

"Working 24 hours a day isn't enough anymore. You have to be willing to sacrifice everything to be successful, including your personal life, your family life, maybe more. If people think it's any less, they're wrong, and they will fail"

– Kevin O'Leary

Don't listen to Mr. Wonderful. Enjoy your life. Prioritize what you want from your business. If you don't have a family, put what matters most to you first.

n+1) Side Hustles Are OK

If you're risk-averse like me — you don't have to go full-time right away, or grind your way to freedom at the expense of yourself. Simply, because you won't know right away that it's going to work out. It's okay to wait until it's the right time. I ran my business on the side for years before going full-time. There will come a point where you simply can't run it "on the side" any longer, and that's when you'll know.