[marban]

I started my professional life ~25y ago with a side project that by 2022 led to roughly 50 more side projects — The vast majority failed, some turned into 200 employee businesses, some others got acquired. In essence, I make a living out of side projects. Side projects are life.

[danielvaughn]

Your career is what I aspired to when I started in this industry over a decade ago. But what ended up happening was that I (a) worked full-time while dabbling on nights and weekends, (b) spent several years trying to decide which project I wanted to really pursue in earnest, and then (c) after picking the project, obsessing over it so much that I never felt it was ready to release. So it's...not going well so far lol.

Can you recall any specific thing you did that brought you success?

[marban]

I think first and foremost is bringing yourself into a position that gets you enough runway (time and money) to be able to take things seriously — even if that sounds like the opposite of a side project. For me it was skipping university and having kids in favour of starting a web agency in the dotcom days. Also, I don't believe in working on something you love — you just need to hate it a little less than the other ideas and be positive that someone will find it useful. Like I mentioned below, luck and timing play an important role and these days I'd say you will also need one unfair advantage (contacts, cash, distribution, etc) to increase your chances.

[mediaman]

I just wanted to say that I love your phrasing of working on something that "you hate a little less".

In general I believe the idea of "work on what you love" to be awful advice; I have found that I get deep satisfaction out of working on something that someone is willing to pay for, even if that means that sometimes it is a headache and I hate doing some of the things that need to be done. Once you accept that those things will continue to exist and continue to need to be done, and it's not going to be bliss, those things seem to matter less.

[jjeaff]

I prefer to try to learn to love something that you believe can bring you success. It is very difficult to do something day in and day out that you don't love some part of. You just have to figure out your angle. I don't love my current business, but I love business in general and I love building things that people like to use.

[cies]

The "love requirement" makes it hard to continue once you wake up one day and find you no longer love it. The "hate it a little less" is much more useful is you dont want to give up on stuff because you have a bad day/week/month with it.

[bonestamp2]

Was there a general goal for each one or any sort of decision tree you used to decide on what to build next... for example, did you only work on things that could potentially be big, or huge, etc? Did you analyze the market size of each idea before starting, etc?

[marban]

I've outlined a few things in an answer below but another aspect I use more and more these days is a negative inbound filter for ideas. Ranging from macro problems like 'Will it require an app' down to even 'do I need user accounts'. Basically, try to put together a few things that you need or want to absolutely avoid due to certain constraints or knowledge and go from there.

[acuozzo]

This is my story as well, more or less. Want to compare notes? Perhaps figuring out what we have in common would help us understand what we're doing wrong.

[hiptobecubic]

As someone who is squarely outside the industry of "side project entrepreneurism," it sounds like the problem is obsessing over minor details about the project and never launching it.

The other person literally said they tried like 50 things and you two haven't launched any yet.

[danielvaughn]

I put that in there to make it more or less obvious that perfectionism was one of the reasons I haven't accomplished much yet. The point was to probe deeper and see if there's some other insight, because everyone already knows that perfectionism kills productivity.

[alfiedotwtf]

At the same time, if you're doing it for a hobby, taking your time until you're happy can be meditative. That's why I'm taking my side project slowly - because I enjoy coding and am using my side project as a form of relaxation.

[kirso]

The main issue is world randomness.

You have no idea and irregardless of evidence that you have gathered if something will work or not. Based on this, it would be very bad to work on something for a year without knowing or getting frequent feedback (cash sent to your bank account by customers).

So the only way is to treat this like poker. You place several bets over a period of time (max 1 month). This way you launch 12 projects in a year and have a better success chance of hitting something that actually works. You have to place bets until the card is right, then you can go all-in.

[imetatroll]

I launched my one and only three years ago and it still doesn't pay its own bills. I work on it when I can, but at this point I feel rather resigned to it never being something I can really be proud of.

[creakingstairs]

By actually launching, you’ve achieved what most engineers only think about. I’m not sure if it would mean anything to you, but I look up to what you’ve achieved so far and hope I can ship something in the next 3 years.

[vbezhenar]

Time is easy. Find a work with 20 hours/week schedule and a lifestyle to live for earned money. Should be possible for software developer. Now you have 20 hours a week without sacrificing free time (or more with sacrifices if you feel it worth it).

Choosing good idea worthy of implementation and finding enough inspiration to finish it is another matter.

[marban]

This describes the point I mentioned above I think first and foremost is bringing yourself into a position that gets you enough runway

Unfortunately, from what I've experienced, this doesn't align with the typical US lifestyle minimum?

[guerrilla]

I'm probably the last person you'd want to ask about this but it sounds like you failed to take risk, possibly due to mild (or not so mild?) perfectionism.

[herodoturtle]

> some turned into 200 employee businesses

Incredible comment overall but this line was particularly Woah!

What advice would have for solo founders of a side project (that later becomes a full time day job) in terms of evolving to a large team?

First hire(s), things to look out for, etc.

I’d find this insight incredible! Hope I’m not asking too much. But such an incredible story you have.

[marban]

To be honest, I would never do something that requires a single employee ever again. I sold my first company because soon enough, all you get to do is manage politics and not the thing you signed up for — Sounds infantile but at some point you have to stay true to yourself no matter the benefits. If you're more of a team-player, there are obviously better options today (remote, etc.) — The only thing I would recommend is not getting too romantic with a co-founder, having clear responsibilities from day one and don't try to make friends along the way — in the end it's all about building success.

[herodoturtle]

Doesn't sound infantile at all. I strongly resonate with everything you're saying.

A little over a year ago I submitted this Ask HN, which helps shed light on my situation: https://news.ycombinator.com/item?id=27039701

It is now a year later and I'm still wondering the same thing as I was back then (as in, I haven't changed up my work setup at all / haven't hired people). I do rely on contractors here and there, but it's rare.

I quite enjoy the peace and quiet that comes with no employees. These days I just do a bit of focused work each day, prioritise spending time with my family, and enjoy sticking to my daily training regiment (the latter has been a key aspect of my life ever since I started my entrepreneurial journey).

Every time I consider hiring people for the sake of more growth, I find myself asking if it'll be worth it, and whether I'll regret it.

I doubt I'd be able to enjoy the work/life balance I currently have if I were responsible for managing people at scale.

Perhaps I'm being narrow-minded here, but it's good to receive affirmation from someone whose done it all before.

Cheers mate.

[marban]

Sounds good to me — Feeding one or a thousand employees doesn't make a lot of difference because you can lose only so many hours of sleep over it each night.

[gen220]

FWIW I know a handful of people of all ranges of success in the tech startup world, managing tens to hundreds or thousands.

Some of them are very driven by the stress of management, and seek it out. Their mentality is that a work situation isn't worthwhile if it isn't pushing you to your limit.

But they're the minority. I feel like you either know that you're this kind of person or you're not.

The rest feel burdened by their situation, and would happily trade for yours 300 days out of the year. They not-irregularly make comments, in private to friends, along the lines of "sometimes I wonder if I'm living life wrong? maybe I should be in the park with my kids instead of on the nth investor call or one-on-one with a direct report".

Like most questions, I think you can answer this with a mixture of experiments and introspection. You say you've manage contractors, for example.

Do you ever feel like you wish you had more responsibility for their lives? The urge to give mentorship is real, do you wish you could do that in a professional setting?

You can probably find ways to scratch those itches that are outside your company, too, for what it's worth.

You're in a good position where you get to "choose your own adventure", so you should experiment with it! Document your feelings, find somebody to talk it through with, iterate towards a happier spot. There's always ways to test your curiosities without sacrificing everything, if you get clever with it. :)

[etewiah]

Shame your Ask HN did not get traction. Might be worth posting it again. It is a bit of a lottery on here.

[nsbr]

Thank you for posting this and previous year's Ask HN. Knowing that it's possible to run some successful && semi-passive && one-person && work/life-balancing SaaS businesses for such a long time is inspiring.

[oulu2006]

Likewise.

I've been through a number of startups and there are jobs that I really really dislike down to my core.

My 2nd startup I did the CEO role and i hated every day of it -- I really respect those who can spend day after day in investor meetings, sales calls, marketing catch-ups; that person isn't me.

My 3rd startup I decided to stick to technology - with a heavy dose of management - and partner with someone who could do the above.

Startups are already barely tolerable as it is, you can at least help yourself a little by being able to focus on the areas that bring a little joy into your life.

[UmbertoNoEco]

This advice aligns beautifully with my experience. It's obvious you have walked the walk.

[heywoodlh]

I deeply appreciate this perspective (and the similar perspective in this HN submission). Thanks for sharing -- it feels so permissive for me to hear these kinds of perspectives and just get to work on side stuff.

I feel like I often hang up on if something should be done or if it is something that will be "successful". So it's cool to hear stories where the goal isn't the financial success of X project -- the goal is the journey and it's a bonus if it's financially beneficial.

Thanks again, know that it helped me to read this comment!

[cgg1]

How do you decide whether a side project/idea is worth pursuing? You mentioned in another comment that you don’t “do the MVP stuff” and go full blown from the beginning. That seems like a big time sink without a rigorous way of validating whether users want what you’re building.

[marban]

Yes it is a time sink and I can't claim having a specific methodology but if you look at all the conflicting theories, literature and endless blog posts that have been written about validation, you might as well just trust your gut.

My amateurish approach is to jot down every idea in a single line of a text file, then walk away. If the same idea or topic strikes me again, I give it a separate text file and write some copy that might go on the product page, together with links to related stuff, screenshots, etc. Then, after another few weeks and only if I still believe in the idea I come up with more details, perhaps do some light coding, brand ideas, register domains, etc. Then (You guessed it), I wait another few weeks or even months and if it passes my still-relevant check I start working on it on the side of my existing, well, side project. The challenge these days is when to pull the plug or go all-in since the market, interests and attention shifts so quickly that it's tough to adapt without losing temper. Doesn't get easier as you get I older.

[cgg1]

Interesting. Thanks for taking the time to answer.

[acuozzo]

If you have some time, would you mind replying to my "Ask HN"? https://news.ycombinator.com/item?id=31217221

Thanks!

[pflanze]

It's too late to reply there (IIRC the commenting period closes after (about) 15d).

[acuozzo]

Got it. Thanks! Perhaps he can just reply here instead (if he's interested, of course).

[acegopher]

Perhaps a more important question is when do you know to pull the plug? At what point do you stop investing resources into the project?

[marban]

There's no exact rule but I'd say 12 to 16 months is a good time to expect some sort of positive trend. I don't do any of that MVP stuff and go full-blown right away because user expecations are high and I'm too old to get pleasure from starting something out of a notion-hosted website. Cash-wise I try to keep it under 20k - keeping in mind that I don't do physical projects and all by myself (no freelancers, contractors, etc).

[xwowsersx]

Could you share the projects here? Took a look at thomas.me but couldn't quite find the projects. Thanks!

[faizmokhtar]

Not OP but here: https://thomas.me/about/

[xwowsersx]

Ah there we go, thanks a lot!

[bitxbitxbitcoin]

What are some of your favorite stories from that life, if you don't mind me asking?

[marban]

I built the first Android Twitter client, sold that to Idealab* and given our huge market share (~40% IIRC ) pitched them the idea to build our own Twitter clone in order to move those users over. Twitter took notice and locked all our apps which eventually kicked off the anti-third-party tendency that we see today. Good times.

* https://bgr.com/general/tweetup-acquires-twidroid-renaming-a...

[marban]

Another time I turned my private news aggregator into a public service (Popurls) which kicked off thousands of clones and was at one time the number one traffic referrer to Digg and Reddit. A year later Guy Kawasaki cloned it, and I find myself invited to a Ramen lunch with Kevin Kelly who blogged about it as being his favorite website. 15 years later, I got funding from Mark Cuban for building a successor. All from a private solo side project that started as a 20-line Perl script.

[twox2]

How I loved the original popurls!!

[marban]

Butterfly FTW!

[codazoda]

I'm not the person you're responding too but I thought I'd mention some of mine. I wrote a blog post called "How to Lose Money With 25 Years of Failed Businesses" where I discuss some of the little side hustles I've managed to kill over the years.

https://joeldare.com/how-to-lose-money-with-25-years-of-fail...

I build a lot of tiny projects and Ben (original blog post) is inspiring me to get them better organized.

[marban]

Besides maximising luck, the only real strategy I follow is buy low, sell high in a sense of keeping the burn low and counting on a win every 3-4 years that will create enough cash to finance the next period of failures — because what got you here won't get you there ...

[techsin101]

how do you stay motivated? what's your stack? do you talk it out with someone?

[marban]

2h sports and a 1h walk every day but that's it. I get motivated from failures because they're the default I expect from having taking actions. Also helps to lower your expectations from life and stay away from comparing your track record with those of others. You know, those 18y olds who flipped their newsletter for 20 millions.

[pid-1]

> but that's it

That's waaay more than your avg office worker though.