AdDuplex Post-Mortem. Part 7: In the End

This is the final part of the AdDuplex (2011–2023) story. AdDuplex was the widest ad network for Windows apps. You can read this part in isolation or start at the beginning.

I tried so hard and got so far
But in the end, it doesn’t even matter.
— American folklore.

By the end of 2018 it was absolutely clear that we are riding into the sunset, and everyone agreed to just sit back and “enjoy” the ride.

Fail slow

There’s a widely accepted “fail fast” mantra in the startup space. The idea is that you test your ideas as soon as possible and if you don’t see some good (at least directionally good) results right away, you just abandon it and move on to the next thing. This way you free up your resources and eradicate useless distractions burning in the back or even in the front of your head.

The problem with AdDuplex was that it worked right away and by the time it kind of stopped working it didn’t just become unsustainable. For the last five years it has required very little work to keep it running. When we worked on expanding the product, we made a lot of technical choices that made it impossible to scale it back dramatically to keep it running on a virtually insignificant budget. Other than cloud expenses though, it demanded extraordinarily little work while still providing some value to the community and bringing in revenue to cover the ongoing costs and compliment my other income (I had to do something else to survive by that point).

On the one hand, I had a business that wasn’t anything spectacular but was nearly zero-maintenance. It didn’t make much logical sense to just shut it down and throw away the modest but personally significant money it was bringing. On the other hand, while not requiring any substantial involvement on most of the days, AdDuplex was clearly a constant presence in my consciousness. It also became part of my identity. When I met acquaintances even just a couple of months ago and they asked me what I am up to these days, I’d usually start by “well, AdDuplex is kind of still a thing…”

I don’t know what hurts the most, holding on or letting go
Reliving my memories and they’re killing me one by one.
— British folklore

In retrospect, I can’t pretend that even today I know the answer whether letting it linger for the last 4–5 years was impeding on my ability to focus on something new and ambitious, or helping me weather the period of lost identity and lack of motivation.

What was clear though, was that it would end one day, as hosting costs of the minimum viable product were well beyond what I was able and willing to cover from other activities just for the sake of the indie community. And, frankly, after the death of Windows Phone/Mobile, I don’t think there was even a real active community.

My biggest mistake in this phase was not preparing for the last few months. Due to the nature of business and the decision to ride it into the sunset, it was highly likely that I will only be able to make the decision to shutdown when it dipped below the horizon. And when the decision is made, and announced revenue will drop to zero immediately. Yet, it wouldn’t be possible to shut it down immediately (unless I wanted to be a total jerk). This meant that I ended up covering the last couple of months of operations out of my own pocket.

Lesson learned: Have an “untouchable shutdown fund.”

This is obviously not something you want to think about in the early days of your business or when everything is going up. But if you decide to let some low maintenance side-project dwindle to the point when it becomes unsustainable, you need to prepare for that trigger event by having enough money set aside for the cleanup.

Final thoughts

I thought about doing a separate post with just “lessons learned” from all the previous parts, but some of them are more important than the other and often hard to extract from the context. So, if you want the whole picture, just start reading from the beginning.

I decided to reflect on my thoughts and feelings towards several key points of the whole adventure instead.

Entrepreneur vs. Entrepreneurial

I was born with the wrong sign
In the wrong house
With the wrong ascendancy
— British-American folklore

Over the years around startups, I’ve observed two types of founders. There are those who are eager to start a business and spend their time synthesizing that startup idea. These are pure entrepreneurs. Some may call them hustlers. They are usually remarkably high energy and can move mountains. On the other side of the spectrum there are people who just like building things with no special regard as to whether that thing is potentially a good business. Once they stumble onto something that feels like it could be a good business, they semi-accidentally turn into startup founders. I’m obviously in that second camp.

We are entrepreneurial programmers, engineers, chefs, you name it. We may create hundreds of things over our lifetime and never even enter the “true startup world.” When we do, we are often too married to our product and are less likely to fail fast. This could be a bad thing or a good thing. There are lots of stories of companies persevering until they find some magic sauce. And we will never know how many of those who failed fast could’ve succeeded eventually.

We are also less likely to launch the next startup right after exiting the previous one. For me personally, I know that I will try to build things for as long as I can, and I’m doing it right now, but I’m not sure if I will ever return to the proverbial startup path. Time will tell.

Venture Capital is a great hammer, but we are not all nails

You’re no good for me, I don’t need nobody
Don’t need no one, that’s no good for me
— British folklore (with an American sample)

Venture capital is a great tool for building massive successes. It is based around the premise of betting on wild(er) ideas and doing it early, so that outsize returns on successes pay for all the losers. In this model “sane” and predictable businesses are a) not great bets to begin with, and b) distract from focusing on the winners.

If you are a VC-backed startup you have three satisfactory outcomes from the VC perspective: IPO, get acquired or die. Yes “dying” is a satisfactory outcome as it is built into the model. Even the “failure porn” I’m engaging in on these pages is probably a VC invention. Celebrating failures seems to be a good thing for founders’ mental health but it also plays into the model of dying and not wasting VC time quite well.

Venture capital is responsible for cultivating most of the Big Tech companies you know about. The model is great for (most) founders of those companies, it’s great for VC funds, and even great for countries (at least in terms of notoriety). But it is also heavily skewed towards the massive wins.

It discards the “losers” quickly and (in civilized cases) painlessly. But it also treats moderate successes as losses. You either go big or go home. As long as you come into the VC world with the understanding of how it’s structured, there’s nothing to complain about.

Having said that, the VC model is so successful and so good at branding that it feels like the only accessible way to fund a startup these days. Which means that in this world there’s no place for “middle class entrepreneurs.” You either invent a tale of how your idea is addressing a multi-trillion-dollar market or you bootstrap. Hopefully, you have a rich uncle to get you started. And if you did invent that tale (and you believe in it yourself), get ready to chase it, even to the detriment of a very nice “lifestyle business” you managed to build.

I know this sounds ranty and I’m not smart enough to see what the solution to this dilemma is. If VC model works for all startup investors starting with angels and accelerators, and up to the massive funds, you can’t force people to invest in “nice and predictable businesses” to the detriment of their bottom lines. Yet everyone seems to claim that the middle-class is the backbone of all healthy economies. Shouldn’t this be applicable to middle-class entrepreneurs as well? As it is today you either become FAANG or go work for FAANG. There should be something in the middle, in my humble opinion.

Enjoy the journey

If you’re throwin’ me to the lions
You should know I’m not scared of dyin’
I wouldn’t take back
One thing I did, one word I said
But I’m gonna make you wish you did
— American folklore

With all said and done, and despite all the whining on these pages, those first five-six years of AdDuplex were the most professionally fulfilling years of my life. We’ve built a product that affected the lives of thousands of developers. I’ve met so many interesting people and travelled to so many places. I’ve taken more flights and visited more places while running AdDuplex than in the previous 36 years of my life.

At one of the startup events back in the mid-2010s I was chatting with a few other founders, and someone said, “Worst case scenario: we’ve learned so much in so many areas that even if our startups fail, we should be in high demand on the job market.” While the first part is certainly true, I’m not so sure about the second one. I’ve learned so much on this journey, but I also learned so many things I don’t want to do. All these learnings and experiences are useful to me personally and will be useful in my future projects, but I wouldn’t really want to do most of those things for a salary.

This means that the most logical path forward for me is to continue on the entrepreneurial path. I may never become a “true entrepreneur”, but I’ll keep building things and hopefully one or few of them will add some financial success to the painful joy of the journey.

So you can throw me to the wolves
Tomorrow I will come back, leader of the whole pack
Beat me black and blue
Every wound will shape me, every scar will build my throne
— British folklore

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And that’s it for the series. Hopefully, it was interesting, entertaining, and maybe even useful. If you happened to end up here directly, you can relive my whole AdDuplex journey from the start.

If you want to get or stay in touch, follow me on Twitter, or if you are reading this way after the whole thing finally exploded, just look me up somewhere :)

And don’t forget to check marker.js for my image annotation and diagramming libraries.