A failed wantrepreneur's view on common startup advice

I’ve been reflecting on my failed wantrepreneur journey, and I realised I followed a ton of advice. Sources were aplenty - influencers, books, podcasts, blogs, coaches. And yet, here I am, with nothing to show for it.

So, I wanted to share my experience with following some I’ve often spotted in the wild. Maybe it’ll help someone who’s been struggling.

Never stop trying

You probably know indie hackers who built 10 projects, one right after the other, before being successful with their 11th. Or read stories of founders who persevered for years, with no income, before finally breaking through.

people gambling at a pachinko parlor

Keep trying and you’ll win big - sounds familiar?

This is a recipe for burnout. All those evenings and weekends add up, and you’ll end up wondering why you wasted your life away. You might’ve believed you were improving day-by-day; fact is, the marginal returns were diminishing.

You need to make a big pivot. And that doesn’t come from reading one more post *(am I attacking my own blog??)*. You need to stop what you’re doing, and take a long break; weeks, months, maybe even years.

You can still casually explore ideas. Just don’t pressure yourself into going at 100% if things aren’t working.

Pick the right industry

Go for a blue ocean, not a red one. B2B SaaS is the best. Find a market where customers are dissatisfied. Make sure the total addressable market is high enough.

dog doing research

What all that “market research” actually is

All of these are sophisticated ways of wasting your time. There are only 4 basic questions you need to answer:

  1. Do people in that market need something?
  2. What product do you want to make to profit from that?
  3. How are you going to build the first version of your product?
  4. How are you going to get your first customers?

You’ll face so much uncertainty addressing these, that there’s no point assessing what’s going to happen 1 year down the line, when you’re looking to scale up. That’s a good problem to have.

Speak to customers before doing anything

I can already feel the “heresy” chants for going against this. I’d probably join in, since I often give this advice. The reality is that no one wants to spend 1 hour going through your list of Mom Test questions.

ain't nobody got time for that

Be honest, don’t you feel like this when someone wants to talk to you about their startup?

You have to provide something of value to people to get that time commitment. Something that’s worked well for me is to build a basic prototype, and offer it for free.

It doesn’t have to be a software service though. It can be a blog / social media post *(am I selling something with this? I wish!)*, a meetup, a spreadsheet template, or who knows what else. Your creativity’s the limit.

Solve problems from your day job

I’m really conflicted about this one. On one hand, I can’t say it’s a bad idea. But then I look back and realise it never got me anywhere.

guy looking conflicted

How I looked like thinking about this

I can come up with two reasons. One, I never acquired deep expertise in one domain. I don’t think it’s a big issue though, as I could leverage knowledge from one area to create something different in another.

The second one is key - I’ve mainly worked in large enterprises. While I’ve encountered plenty of problems here, there are two major barriers to profiting from them:

  1. They’re reluctant to engage with a random little startup (let alone buy!).
  2. Implementing the software incurs a large human cost for them, no matter what.

Final words

I know there are plenty of success stories that will prove me wrong. But survivorship bias is embedded in startup culture - you rarely hear about the 99% who are struggling. This post was for them.


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