I made a $50k entrepreneurial mistake

Losing tens of thousands of dollars

I could say I made $100 off my first SaaS product. But that would be a lie. It cost me tens of thousands of dollars.

I had built the app on the side while working remotely for Adobe, where I had worked for 11 years. I kept waiting for the time to be right - when the app was ready to go. I knew it wouldn’t take all that long til I was crushing it.

After all, Peldi had left Adobe not long before, and he was already crushing it with Balsamiq.

How hard could it be?

I finally put in my notice, telling myself I was two weeks out from being ready to launch.

I had a plan - I could see it all, the dream was becoming real.

From the first day of being “self-employed”, I would get up every day before dawn, with tons of energy, fill up my coffee mug, hop on my bike and head to the office, and be hard at work before most people were even awake.

I was having a great time, and told myself I just needed one more week of development before focusing on sales and marketing.

The next week I told myself the same thing. And the week after that. And on it went.

Eventually I did send out some emails. I got a single sale. That was exciting, but I was almost two years in.

By this time, my wife and I were about to have our first kid. There was more pressure, and I was about to have people depending on me. With no real signs of progress on my business, it was time to close doors.

I had been doing what is so common for developers trying to be entrepreneurs. I was procrastinating, avoiding the hard parts. Sure, the app had room for improvement, but all apps do. The fact was that I was starting to learn that hard-earned lesson about getting in front of customers early.

I had entered a market I knew nothing about, and had no connections in. But I saw a massive market - appointment scheduling software for anyone business who wants to let their customers schedule online - and I knew I just needed a minuscule sliver of it. This was true, but that’s of no use if I can’t penetrate it.

I can at least say I made $100 off my first SaaS. But I also spent tens of thousands of dollars spending savings to live during that time.

Moving on without regret

I could call this one big expensive two-year mistake. And in a way it was, but that an unproductive way to look at it. No need for shame or guilt here. It was also a huge learning experience.

Do I wish I could have learned these same things in less time with less cost? Sure. But that’s just the way things go sometimes.

Nowadays everyone’s talking about quick validation, fast iterations, trying lots of small bets. I agree that this is the best way, but in 2012, this wasn’t a common approach. It didn’t occur to me to do it any other way than how I was doing it.

So do I regret it? Hell no.

Lessons learned

I learned so many crucial lessons about business, and myself:

That talking to customers as early as possible is crucial to reduce the risk of wasting time building something that will never see the light of day

That sales is hard

That marketing is hard

That apps are never ‘finished’

That I enjoyed the building part, and not the marketing/sales (this has since changed)

But also… that I could build a sizable app on my own

That I have the drive and determination to keep going even when it’s hard

I have internal motivation that is crucial for this type of work

That there are a ton of hats to wear as a founder (development, sales, marketing, accounting, taxes, design, communication, writing, contractor management, etc). And that while I didn’t love them all, I wasn’t afraid of diving in and figuring them out

There’s a lot more too.


The main takeaways here can be boiled down to a couple things:

Regardless of how you feel about Taylor Swift’s music, there’s no denying she’s incredible at business. She recently said:

As my mother used to tell me: Failure is not the opposite of success, it’s a stepping stone to success.

It’s important to remember this. It’s hard as hell at times. You’ll want to quit at times. You’ll ask yourself what the hell you’re doing, and why. And that’s all okay, and normal.

But if you have it in you, you’ll take a quick break, and you’ll get back at it. If it were easy, everyone would do it. And there’s a reason why most people would never consider putting this kind of pressure on themselves.

As someone who’s spent many years on this journey - and even reached the “destination”, in a sense - it is true, that the journey is often better than the destination. We do this because we love the challenges.

You either have it or you don’t. If you have it, I don’t need to tell you to keep going, you just will.

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