Or to take up repeatedly at 5am and work 12+ hours a day on something that gains traction slowly.
I’ve been part of a fun project backed by good people and then had new tech eat our lunch. We still spent long hours trying to find value somewhere. That was less fun but OK, not a waste.
I have been part of a slow traction project when the first great dot-com crash happened and too many contracts got cancelled. That was the worst time of my professional life but not a waste.
I have spent time on very promising tech in a field ripe for either a good living providing something needed in service deserts, or an exit. The founder found every excuse not to launch, to keep versioning pre-launch. That neverlaunch project was a waste of a year that I’ll never get back.
Learning when to bail is a true skill. Not to quit just because it is messy or inconvenient, but when it is actually harmful.
> Almost no SMB views contract management as an urgent problem.
And I think it probably is, then IMO you made the right decision. I don’t know the space very well, but my gut feel would be SMBs don’t have real CLM needs like Enterprises do, they mostly just need something like DocuSign. Taking the money and pivoting might have worked, but I agree, it’s a massive risk in terms of your time and your team’s jobs.
Also, if the CLM product targets a Salesforce integration, sounds like it’s more of an Enterprise than SMB product? While their core e-signature product targets both SMBs and Enterprise.
Did you ever get around to writing that article? It sounds interesting
I have not, but you know, I got that request a lot back in 2016 too, so it sounds like i really should write that article.
I promise I will get it written this year.
Who knows, it might even end up here on HN.
I'm surprised (and delighted) to see this back on Hacker News. I'm happy that people find value in the article, and the process writing it forced me to put my thoughts together and helped get me through an emotionally difficult time.
To address a few questions from the comments.
1) A common opinion is that I gave up too quickly, that I was just burned out, or taking the money would have let me figure things out later. This was simply not the case. An experienced mountaineer knows if a mountain is climbable with the team, gear, and weather he has. This one was not.
2) I would have been 100% fine with the team and investors going ahead without me, but AFAIK, neither side ever discussed it.
3) We were absolutely not viewing contract information, and would not have been able to do so even if we wanted to. We anonymously logged when functions were called without storing user or input data of any kind.
4) Six years later, I'm doing well. The Disrupting Japan podcast is going strong. I took a senior role in corporate VC for a while, and ended up at Google.
I was overwhelmed by the attention and positive response I got from this article. The asymmetry of value of money and time was one of my main learnings, and I'm glad to see it resonates with so many other founders.