Olly Headey

August 22, 2023

Building something new

It's been over three months since I left 37signals on a bit of a whim. When I left I had an emerging plan with someone to build something new, but as it turned out I had nagging doubts and couldn't get excited enough about the opportunity so it quickly fizzled. A bit of a shame, but them's the breaks. I decided to take the summer off instead and do not very much other than go on an adventure across Italy. Would recommend.

I've daydreamed about creating something new since before I left FreeAgent. Not just hacking together an app like the fun side project I did during Covidtimes (RIP Blogline ⚰️), but building an app into a business. Around June time I had a vague idea for something I could build that was small and fun, so I just started building it. No plan, little thought about where it would or could go, just build and see where it lands. Maybe this is bad advice, but I think this is a viable approach. It's the equivalent of starting a novel without a plot, but as Stephen King says in On Writing, plot doesn't matter:

I don’t take notes; I don’t outline, I don’t do anything like that. I just flail away at the goddamn thing.
So with my "What If" question in mind, I started flailing away on my goddamn thing and actually, after about 3 work weeks of effort (spread over 3 months!) things have started to take shape. With a few more weeks of cranking I should be able to have a viable (if bare bones) product in the hands of a few lucky/unfortunate SMEs for a bit of testing. This has inevitably led to thinking about where I should take it after that. What path should I choose, and do I even want any of this at all?

In the startup tech world right now there seem to be two distinct camps: the classic VC-backed rocket ship camp, and the "build in public" bootstrapper camp. Both camps ultimately want the same thing – a popular product that brings in cash money – but the founder journeys are very different. The LinkedIn and X (😳) algorithms are relentless in serving me views and hot takes from both sides, and the more takes I read (which is too many, I know, but I can't help myself) the more averse to the venture-backed approach I've become. Bootstrapping on the other hand, keeping things simple and more nimble, seems far more appealing.

It's a whopping cliché to say that life is a journey and not a destination, but it's true in startupland. Starting FreeAgent my early 30s was a brilliant journey. I was out of the dismal rat run, and working remotely building something I believed in. It was a wonderful, liberating feeling. Making decisions, chatting to customers, raising money from investors, hiring employees... every day was different and there was so much to learn! Quite the change from building substandard web apps with third-choice frameworks for stiff financial institutions. Of course there were plenty of shitty times, and while the destination (which was, because of the VC train, pretty much always "flog it" and hopefully make a few quid) was something to look forward to, but it was a proper lived experience, and one that doesn't come along that often. You have to seize these when you get the chance IMO.

Since that particular journey has ended, taking another one along the same lines is pretty unappealing. The thought of creating pitch decks with over-optimistic growth projections and taking dozens of calls to hear my ideas resoundingly shitpanned sounds like a miserable experience. I'm well aware that there's a very large chance that any idea I have won't be remotely successful, but I'd prefer to let the public decide, thanks. Even if VCs loved my ideas and coughed up the dough, the burden of expectation with half a million venture dollars in the bank would be weighing me down and stressing me out big time. Plus I have no desire to relive the past, that's been and gone. I want to see new places and have new experiences. That said, I'd definitely recommend VC to new entrepreneurs so don't let me put you off. It will be a wild ride and you'll love it, win or lose! 😅

I prefer a calmer journey right now. Cruise ship age (nope!) is fast approaching so I want a more comfortable ride rather than be strapped to a surfboard on 40ft waves. The goal is to bootstrap a profitable microbiz with few overheads, not convince people I can build a rocket ship. To build a fairly boring B2B SaaS that's something that I want to use (or have needed in the past) and can dogfood every day. Building in public doesn't come naturally for me though, mainly because I'm a reserved Englishman and the thought of having to big myself up in public is horrifying. However, I'm happy to write about it now and again to the few subscribers of this underwhelming periodical, if that counts.

Of course it's only the honeymoon stage of the journey, but there are a few things that have stood out to me already. Firstly, coding for the joy of it. Well, the occasional joy of coding that comes after emerging victorious from periods of immense frustration. I have far fewer programming skills than the many talented people I've worked with over the years, but I still love the building, the endless learning, and seeing the creation of a tangible thing that people want to use. It's very satisfying.

Working without deadlines is a delight. I spent years building FreeAgent but it always felt like a massive rush. Corners were cut, I had to be slapdash often. This was fine because we got the product out there and shipped new features regularly, but this time I'm enjoying taking a bit longer to make sure the code remains as good as I can make it. No deadlines can also be a curse – some people need a deadline, a bit of external pressure, in order to instil momentum. There's a danger without one you end up noodling, but I'm not worried about this myself because I'm far too impatient. I have an inner ghoul that insists I try and get stuff out there ASAP, and I can already hear it moaning.

Exploring how much leverage one can exploit from the advances in tech fascinates me. Is being a 'SaaS solopreneur' realistic? Is it feasible for a single person (with a bit of contractor help should profits allow) to design, build, operate and support a SaaS product at reasonable scale? When does it all break down? There are plenty of examples of this happening in the wild, so I'm intrigued to see how it pans out despite knowing first-hand about the perils. The "build a SaaS" meme is all too real.

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At the end of the day I love the excitement of how the startup story unfolds. The characters you meet, the endless plot twists, all the possible outcomes. This is the same whether you're bootstrapping or raising a rocket-shaped wedge. It may come to something, it might flop, or you could just get cold or itchy feet, but if you believe in the thing and can enjoy the ride, it's worth taking the plunge.

As for the product, it's not quite ready for a public reveal yet. Not even so much as a teaser, soz. I want to feel more confident about what's cooking before I serve it up. That said, if you happen to be interested in a low-touch, low-cost, high value (potentially) product that brings your team together and helps people be more productive, all without being yet another distraction, then email me at olly@hey.com as I'd quite like a chat in the coming weeks.



About Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.