015 - the indie enterprise software developer fairytale
I tell people all the time that I am developing eno like an indie video game. For people familiar with indie games, this brings to mind the solo game developer who toils for years on their game, obsessing over every detail until it is absolutely perfect. In the fairytale version of this story, the developer then releases their game to massive critical acclaim and becomes fabulously rich and famous overnight.
This is overwhelmingly NOT how most indie game stories go and everyone is well aware of that. Most indie games get released with basically zero people noticing and sell a handful of copies before they disappear under the daily releases of hundreds of new games.
The indie game fairytale is not a myth though. It does happen and it happens quite frequently: I would guess at least once a month.
The first true indie game fairytale I encountered was that of Jonathan Blow. In late 2004, Blow began working on a game which he would ultimately release under the name Braid in 2008. Braid received immense critical acclaim and did millions of dollars in sales. Blow used this financial success to hire a small team to work on his next game, The Witness. It would take another six years to complete. It would also be a massive success, critically and financially, doing $5 million in sales in its first week.
The reason I love indie game fairytales is not the money. In fact, if I gave you some anecdotes from the most successful creators of enterprise software, these sums would seem paltry. What I love is how directly and immediately financial success is tied to the quality of the product. The games that achieve this level of success are innovative, visually striking, and they run flawlessly. The pains of the creator in striving for perfection are essential to the creation's ultimate success.
A few months ago a friend who I chat with a few times a year, messaged to tell me about this new game called Balatro. He said "The new crack is Balatro". I bought it that night. This is called word-of-mouth and it's the reason this low-profile indie game sold a million copies in its first month. The game is so interesting and engaging you can't help but talk about it.
The same friend later sent me an interview with Balatro's creator, a sole developer who toiled in obscurity for two and half years to make this game. For the first one and a half years of that he was also working a day job to make ends meet. Throughout the interview you could tell just how meticulously he had planned out every single mechanic of the game to make them work together in this incredible harmony.
This is not how enterprise software works. When we started my previous startup, Closing Folders, my business partner and I didn't understand this. We thought we would make the software, show it to the people who it was for and then, if it was good, those people would buy it and use it.
The first problem was that people who the software was for, were junior lawyers. Junior lawyers are not very important at law firms so they don't really get to decide to buy software. So we came up with some features that made the software useful for more senior lawyers. These lawyers were much more important.
Some of these important lawyers thought our software was good and decided they wanted to buy it. Unfortunately, that led to a new problem: these important lawyers didn't usually buy software. Other people at the law firm were in charge of buying software. A lot of these other people worked in IT. Our software wasn't useful for people in IT. In fact, it just created a bunch of problems for the IT people to deal with. So we had to make our software create less problems for IT.
Eventually we made the right combination of people happy and actually got the law firm to buy the software. Now was the time for the people to use the software. Except…they didn't use the software. It had taken so long to get the law firm to buy the software that the initial people who wanted it had forgotten about or become busy with other things. It turned out that we actually needed to hire someone whose sole job was to go to all the people who had wanted our software, tell them that they now owned it, remind them that they wanted it and show them how to use it.
Even as we got better at this process, it often still took over a year, start-to-finish. While our happiest customers would tell their friends about our product like my friend told me about Balatro, these friends didn't go out and buy it that night. The best they could do is set in motion the months long sales process with a sense of urgency.
The time out of our days required to navigate this process was significant. Frankly, it would be impossible for one person to do all of this, even if they could support themselves indefinitely. It was essential to have a team. Financially, the software was paid for as an annual recurring subscription. This was amazing for the long term, but in the short term a large portion of that money had to go towards supporting the sales process - both directly by paying customer facing staff members, and indirectly by investing development cycles on features that would help move the sales process along more smoothly.
I kind of hate everything about enterprise software sales. What I hate the most though is that you don't live and die by the quality of the product you are making. Certainly, there are successful enterprise software companies with good products, but there are also many successful enterprise software companies with bad products. You can go either way! If you can go either way, that means every time you have a decision to make that impacts software quality, it's up for debate. At the worst, it leads to poor incentives for companies to make deliberately bad software to exploit dynamics in the sales process (e.g. charging for single sign on). At best, you can get away with a lot of bad quality work, even if you are well intentioned.
The way software is sold has an immense effect on the way software is made. I want to make exceptional software. Financially, I am prepared to live and die by the quality of my creation. I want to reenact the indie game developer fairytale in the world of enterprise software. I am not sure this is possible and, if it is possible, I am not sure exactly what it looks like. What I do know is is that it certainly looks different than the way things are done today.
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