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The best product doesn’t always win, and product is not a longterm competitive advantage.

I have trouble swallowing this one. He decided to compete on product, but instead spent more of their limited resources on other things.

We started burning money on ads and hiring sales people

In order to stay competitive, we had underinvested in our engineering team due to cash constraints and stretched them across mobile, desktop, and web.

We started to get an endless stream of bug reports from our customers.

Our clients were unreliable and had syncing issues

This smells to me like neglected product and over-stretched developers. Chasing new features instead of building solid foundations by selecting the most important ones and getting them right first.

As a customer, as soon as I see something like "sync issues" that's a dealbreaker. If I can't trust your product to keep my data safe, I'll stop using it.

It does look like they eventually figured that out:

We had to hit pause and spend years — literally years — rewriting all of our clients

But by then the competition had decisively out-producted them:

One day recently, I looked at Asana and it slapped me in the face:

It’s better.



Completely agree! The best product does always win. The founder did not focus on making the product better but jumped from marketing to design, to raising money, to expanding the team. The product did not keep getting better and they lost.

1. If you are in a competitive VC-funded space, it’s foolish to compete without raising money. Don't bring a knife to a gun fight.

Again, not true. You win if your product is better. Think outside the box, and make something that no one else has made and users will love it and you will win. I'm not saying that is easy to do. Just that's what wins.


I hate seeing this very thing play out in real time, but I find it particularly sad when investors and VCs then takeover the board and outmaneuver the founders and Csuite to the point they barely run the company anymore. They take advantage of technical founders without the board level chops to do this. Then short term focus or otherwise misaligned incentives mean the board slowly, but unknowingly, runs the company into the ground. (by doing stuff like hiring a bunch of marketing people while the technical debt starts piling sky high...)




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