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Ian Crosby here. If you don't believe me, believe the CEO of Shopify who was an investor and partner: https://x.com/tobi/status/1872753436116332994



Ian, I emailed you a couple years ago when I felt Bench had become worse and worse for customers. I was sad to discover that you’d left and I felt the difference was definitely attributable to your departure. I switched providers shortly thereafter.

So, speaking as a former customer, the tragedy and timeline you mention pass the sniff test for me. So glad your next venture has been going well for you!


Thanks Marc. Wishing you the best in your ventures too!


I’d like to clarify - and ought to have done above - that I’m not saying you’re lying in your Tweets. Just that the story of any business failure is often more nuanced than “investors are bad”. And that story may be revealed in court filings as I’m sure creditors will be going to court to get their money back in the coming months.


Hi Ian. Sorry to see this happen to the company you founded. Can you say what the board's strategy was that conflicted with your vision?


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Pray tell, how was he possibly supposed to help the customers of the company he was fired from 3 years ago?

I found his posts interesting. I was a Bench customer for several years until we sold our business, and I appreciate the background information about the bullet we dodged.


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> every good ship can get a new captain and sail on. If not, the problem isn't the sailors it's the captain (who set the ship before the fall).

You're seriously claiming a bad leader can't destroy a company/organization/project/country?


You're arguing a different point. The old CEO claims it's his absence that caused the failure, not the presence of the new CEO. You're arguing that it's the presence of the new CEO that caused the failure. GP is pointing out that if the absence of the old CEO is what caused the company to fail as the old CEO claims, and not the actions of the new CEO, then it wasn't in good shape to start with.


Ah. That's a bit more sane for sure. Although with some big caveats. A founder can be crucial for a long time, and there's nothing wrong with that. It's a tradeoff. You don't want to spend time operationalizing the business before it's stable for example. That's just a waste of time. The board very well could be mistaken on which stage the business is in.


Glad someone got it.


Doesn't make a ton of sense though. A bad captain can steer into the coastline and kill everyone.


Bad investors and a dysfunctional board can destroy a company. When late-stage investors push to fire the CEO, they often do so to install a puppet CEO who will give them greater control over the board. This allows them to prioritize financial decisions that serve their own interests, often at the expense of other shareholders, such as early employees, whom they disregard.


This in the response made me cringe a little:

> I wanted to continue with what was working and with what our partners had signed on to distribute.

How does he know it was working? He says it so matter of factly.

And that’s what this big-mad comes down to.


You make a fair point. I would have liked him to elaborate more on the potential acquisition that was declined.

However, he mentioned they just raised $60 million. If his approach wasn’t working, why would anyone invest that amount? And if the plan was to fire him, given that his vote was required, wouldn’t it have been more transparent to say upfront: “If you reject the acquisition and opt for this $60 million investment instead, we’re going to fire you”?


How does he know? He was the CEO. I'm guessing that he had access to the company's metrics.


Metrics alone don't tell you if a strategy is working in the long term. It was no doubt a highly informed opinion, but still an opinion.


> every good ship can get a new captain and sail on

If the new captain is good. But a bad captian can sink any ship, unless the crew is willing and able to mutinee to prevent it.


> "this is exactly what happened"

In a direct reply to the thread. Well, it is confirming the original thread.


Start-ups by nature are not good ships.




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