Failing Startup Confessions

Hi fellow Yalie! DC’08 here. I’ve been bouncing around the startup and tech world for a few, so hopefully the feedback I have is helpful.

One thing I’m noticing about your journey is that you’re focusing on the software, not the customer. It is infinitely easier to start with a real customer’s problem and solve it, rather than starting with a product and trying to find someone to buy it.

If it’s a valuable problem, they should be willing to pay you for the solution. Don’t give it away for free — you’ll trick yourself into thinking it’s worth more than it is.

Once you sell your solution a bunch of one-off times, you have a “service”, plus hopefully a few bucks in your pocket. You probably haven’t written a line of (reusable) code yet. This will drive you insane, but it’s worth the wait.

At this point, as a software guy, you’ll start noticing commonalities in the services you’re providing (nothing annoys software people more than doing something more than once). This is the first hint you may have some kind of “product” to sell.

You’re now ready to go to your customers & prospects and offer a choice: get the service you’re used to now, or wait a bit (pay now though!) for the alpha version software with features x, y, and z. The software is probably going to be a worse, cheaper option than your personal service touch. That’s fine — this is a textbook example of “disruption”, where you are trying to replace your valuable service with an inferior product that has a greater potential growth curve.

Now you have a software business! Congratulations, your real problems are just beginning :)

Email in my profile if you want to chat. Good luck!

You should get a job unless you're ready for a radical mindset shift.

All your products are extremely technical and target the worst market for first time founders - developers.

Developers, one of the most highly paid people in the world but also people who rather waste 4 weekends tinkering with something than pay you $5.

You need to solve business problems and I suggest build solutions for _non-technical_ people.

Find a business problem that's worth at least $99 p/m and niche down on it. E.g. do some research, speak with people, find manual/spreadsheet/data entry process in the business and automate it where possible.

It's better to have 100 customers paying you $99 p/m to make $10k MRR, rather than 2,000 customers paying you $5 p/m.

And it's not hard to sell $99 p/m product when you speak with business people and solve their problems.

You're also very technical, so I assume you have no sales skills or experience. You either need to find a business co-founder who'll do that, or be ready to reinvent yourself.

Also youtube around for Dan Martell, he's got a lot of great content from a few years ago around MVPs and early stage startups.

These are more like technical experiments, that have a remote possibility of making some revenue. You could continue to develop your idea "muscle", but for some techies it's a long road that never gets there.

The best advice I can give you is to find someone who is more on the business side of things. They can often see problems that have definite pain points, that many people would pay money to have fixed.

Startup Schools co-founder matching platform is a good place to start: https://www.startupschool.org/cofounder-matching

Good job. At least all you lost was your time! I have lost a lot more than that.

Ask an AI how to turn each of those into a business, or how to monetize each of those.

Get a job. How are you surviving without one? Off 100 dollars made between January and Now?

Failed attempts at entrepreneurship as a technical founder

Honestly you should for sure get a job. You seem to be choosing startup ideas that people with jobs choose, use offshore labor from the start, rapid pivots into tools to pivot faster, udemy courses, these are all side projects. Nothing wrong with that, but do them at night and save up your cash for when you have a big idea that can’t be done that way.