What's one startup lesson you had to learn the hard way?

by•

I'm a marketing tech builder. I've sold a startup, angel invested in a few, and am now building another.

Some things I believed 10 years ago turned out to be completely wrong. Others took me years (and quite a bit of money) to understand.

A few lessons that stuck with me:

  • Angel investing is probably the fastest way I've found to lose money.

  • Your first business partner matters more than your first customer.

  • The bottleneck is almost always product-market fit, not marketing.

  • Hiring someone to "run the business for you" is much harder than it sounds.

  • Build where you have an unfair advantage. Passion alone won't save you.

  • Knowing when to back down is just as important as knowing when to push harder.

  • I've never seen anyone succeed long term without working incredibly hard, regardless of talent.

I'm curious about two things:

What's a lesson you learned the hard way that nobody warned you about? And which of mine do you disagree with?

Especially interested in hearing from people building their second or third company.

16 views

Add a comment

Replies

Best

Your first business partner one, 100%. Over 20 years ago I started a company with a childhood friend. I put in about 90% of the money but we made decisions as equals. The product was done, we were about to start selling, and then we couldn't agree on how to spend the money. Ended in a fight. Back then I had no clue how ownership and decision rules work, and honestly I was mixing up being friends with being business partners. Been solo for 22 years since.

I've never sold a company or a business either. I'm attached to them and want to grow them myself, and I guess I just like growing things. The crowdsourcing service I've run for 22 years has given me trust more than money, and that feels like the bigger asset.

 Appreciate you sharing it!