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Hi, author here. 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 for

Hi, author here. 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.

crabbygrabby 4y ago
Good for you, you did the right thing. Maybe you would have shoe horned some fix, but honestly, screw it. Imagine waking up at 5am and forcing yourself to work on a company that you knew wasn't going to make it.
- sshine 4y ago
  > Imagine waking up at 5am and forcing yourself to work on a company that you knew wasn't going to make it. Or to take up repeatedly at 5am and work 12+ hours a day on something that gains traction slowly.
  - uptime 4y ago
    Both are valid, one does not cancel the other out. 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.
hypfer 4y ago
> I might write another article on how to tell these tangential feature requests from useful feature requests. Did you ever get around to writing that article? It sounds interesting
- timoth3y 4y ago
  > 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.
  - kotcity 4y ago
    Yes, this is of high interest. The problem is more common than many people think and I anticipate this post with great enthusiasm.
    - mwigdahl 4y ago
      Same here, this would be very useful to me both directly and in conversations with my executive management.
  - JohnTHaller 4y ago
    If this original post (and thank you again for it) pops up on the HN homepage from time to time, it may be worth it if you have the time and bandwidth.
thejammahimself 4y ago
The comparison you made between money, and time is one which I think perfectly explains the situation you faced. I can imagine it must be incredibly difficult to spend so many hours working on something you're not sure is going to work out. Time is, I think, valuable to us all. Some of us often feel we don't get enough of it, and I think sometimes we overlook how important free time is when making decisions in life. Sounds like you're doing well now; you learnt an important lesson through this experience. Hope it all goes well in the future!
cynusx 4y ago
Did you consider moving up earlier in the contract lifecycle to the contract negotiation process?
- ramesh31 4y ago
  I think the reason these companies fail to begin with is that they are too high level and generalized. Even a specific subset of CLM like managing real estate transactions is an exceedingly complex business domain with hundreds of entrants. Trying to go after the entire market with a single product is just naive IMO.
deleted 4y ago
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brokenodometer 4y ago
Great article. I’m curious what ideas people sent you after publishing for solving the gratification problem. What was the strongest, even if you still don’t think it would have worked?
vlovich123 4y ago
Since you were done pursuing the idea and were just shutting things down, did you ever consider open sourcing whatever you had? Curious about the thought process you went through around that.
yashap 4y ago
It was a good read, thanks for writing it. Also, assuming this is correct: > 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.
- coverband 4y ago
  DocuSign actually offers an integrated CLM product, built on top of a smaller company they acquired a while back. With everything also integrated with Salesforce, etc., it makes automation pretty easy.
  - yashap 4y ago
    Ah interesting, didn’t know that. Certainly their main use case that drove their growth, though, has been a simple “get signatures on a document over the internet” product. 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.
einpoklum 4y ago
deleted 4y ago
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crabbygrabby 4y ago

Good for you, you did the right thing. Maybe you would have shoe horned some fix, but honestly, screw it. Imagine waking up at 5am and forcing yourself to work on a company that you knew wasn't going to make it.

sshine 4y ago
> Imagine waking up at 5am and forcing yourself to work on a company that you knew wasn't going to make it. Or to take up repeatedly at 5am and work 12+ hours a day on something that gains traction slowly.
- uptime 4y ago
  Both are valid, one does not cancel the other out. 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.

hypfer 4y ago

> I might write another article on how to tell these tangential feature requests from useful feature requests. Did you ever get around to writing that article? It sounds interesting

timoth3y 4y ago
> 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.
- kotcity 4y ago
  Yes, this is of high interest. The problem is more common than many people think and I anticipate this post with great enthusiasm.
  - mwigdahl 4y ago
    Same here, this would be very useful to me both directly and in conversations with my executive management.
- JohnTHaller 4y ago
  If this original post (and thank you again for it) pops up on the HN homepage from time to time, it may be worth it if you have the time and bandwidth.

thejammahimself 4y ago

The comparison you made between money, and time is one which I think perfectly explains the situation you faced. I can imagine it must be incredibly difficult to spend so many hours working on something you're not sure is going to work out. Time is, I think, valuable to us all. Some of us often feel we don't get enough of it, and I think sometimes we overlook how important free time is when making decisions in life. Sounds like you're doing well now; you learnt an important lesson through this experience. Hope it all goes well in the future!

cynusx 4y ago

Did you consider moving up earlier in the contract lifecycle to the contract negotiation process?

ramesh31 4y ago
I think the reason these companies fail to begin with is that they are too high level and generalized. Even a specific subset of CLM like managing real estate transactions is an exceedingly complex business domain with hundreds of entrants. Trying to go after the entire market with a single product is just naive IMO.

deleted 4y ago

[deleted]

brokenodometer 4y ago

Great article. I’m curious what ideas people sent you after publishing for solving the gratification problem. What was the strongest, even if you still don’t think it would have worked?

vlovich123 4y ago

Since you were done pursuing the idea and were just shutting things down, did you ever consider open sourcing whatever you had? Curious about the thought process you went through around that.

yashap 4y ago

It was a good read, thanks for writing it. Also, assuming this is correct: > 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.

coverband 4y ago
DocuSign actually offers an integrated CLM product, built on top of a smaller company they acquired a while back. With everything also integrated with Salesforce, etc., it makes automation pretty easy.
- yashap 4y ago
  Ah interesting, didn’t know that. Certainly their main use case that drove their growth, though, has been a simple “get signatures on a document over the internet” product. 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.

einpoklum 4y ago

deleted 4y ago

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