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Email to Former Board Member (docs.google.com)
59 points by devlife 11 days ago | hide | past | web | 22 comments | favorite





For those wanting/needing context: https://news.ycombinator.com/item?id=24793170

> If you have gotten this far and think this is a self-indulgent pity party, please just stop reading.

I don't judge (actually I feel for this guy), but let's be honest: isn't it? And this email just reinforces the idea. In fact, as all this stuff I've just read settles in my mind, empathy starts to give place to the feeling all of this is kind of... petty?


Here's the context, from the author:

"Simultaneously, we were forced to deal with a board member who was beyond counterproductive. After we bought him out fully in 2019, I sent this feedback email detailing the ways in which he had disrupted our board and company. Dealing with this issue was one of the loneliest times I faced as a CEO. To be clear, this email is unlike anything I’ve sent in my life, and I’ve thought long and hard about the decision to share it. I’m not doing so to disparage the individual in question; the only objective is to help others who might find themselves in a similar situation. (Nothing has been removed, including typos, from the email except for names.)"

https://ryancaldbeck.medium.com/transitions-fa7ce4af435


Related Twitter thread: https://archive.vn/o4JP0

> As far back as college, I’ve made hard decisions with the goal of building a great family. That emphasis has impacted everything from which jobs I’ve pursued to what foods I’ve eaten — even before I was married.

That doesn't sound healthy to me.


Why?

The sender of this email seems to be upset because they let the receiver of this email walk all over them for so long. Publicly releasing this email makes both sides seem so unprofessional. The real lesson here is that this CEO’s lack of healthy boundaries prevented them from saying no—over and over again—to making obviously bad choices. I feel for this person’s employees.

Agreed. I don’t know anything about the players here, but I’m kind of surprised that a CEO would air a letter like this publicly, not only from the “dirty laundry” perspective, but because it comes off as really petty and ridiculous.

I’d expect this from some middle manager at a university.


Unpopular, but I agree. The writer comes off as terribly weak. I read about his personal and health challenges, but I think that would be an even bigger motivation not to let this deranged (according to the doc) board member going on with that circus.

I regret that we went thruogh the "diligence" process in just a few weeks

Does anyone work in M&A? What in your experience is a sufficient timetable for diligence and discovery? I ask working for a company that "grows by acquisition", and being in a middle management role I find myself often playing clean-up crew to some alarming things that should have been caught during diligence, but am growing increasingly weary being told "we didn't have time".

This is no attempt at malingering my duties, but I've lost one staff member already to the burnout from this, and am quite fearful I'm about to lose another. Both have told me "it's not you, you've been a great manager" yet both have lamented feeling like their jobs have turned into playing the 'janitor' role for messy acquisitions saying "you did what you could"

My own complaints up the food-chain have been returned with shrugs by a director who seems equally powerless in a process that is burning people out--and I'm considering looking for the door at the end of the year from it.


Being in the middle of an acquisition is a form of limbo. Nobody wants to start anything new, partly because of management uncertainty and partly because it could change the valuation. It consumes all the time of top management, and nobody is minding the store. So you don't want to spend too many months stuck in that state.

(I know a company that's in that position right now, and there's no visible planning for 2021.)


there's no visible planning for 2021

I have this impression as well, detaching a bit and looking at 'everything' (or as much as my perch will allow).

To say it's frustrating would be an understatement; I considered applying to a role and effectively taking a demotion and being an IC again. Which, if it says anything--is something my last two predecessors did as well.

Otherwise you've hit every nail on the head and quite well summed up my feeling of 'limbo'.


Releasing this as-is seems like a bad idea. He's likely addressing a former board member by name, as well as their firm. Couldn't you just look at all of the names of board members and their firms, compute the metrics of those names with the typeface being used, and then figure out exactly who he's talking about?

I know a few people on Twitter have tried, but AFAIK no names have been leaked. But let's say he had said the name... is that a problem? People write blog posts about bad experiences quite frequently.

[EDIT: I was wrong, yesterday the person publicly acknowledged it's him.]


the name has leaked. It's Craig Shapiro from Collaborative Fund and Craig has replied on Twitter:

https://twitter.com/cshapiro/status/1317212694529802242


> I urge everyone to think three times before you pile on to a Twitter mob or urge suicide on the target of a mob attack (thanks @ilyasu and @matrixpartners).

JFC, the guy who told him to commit suicide tries to act like he's the victim and defends himself by claiming he was just part of the mob, and didn't know who he was telling to kill themself. Nice to know he thinks it's fine to urge strangers to commit suicide.


Holly crap, he doesn’t even meaningfully deny it.

The email is funny but this company raises some red flags for me. Firstly I couldn’t figure out what CircleUp actually does as a “tech startup” from reading their website.

On further reading they used to do something (a marketplace to connect investors and consumer companies needing funding) but they pivoted into being a plain old investment company (ie what the founders used to do themselves).

They make some very dubious claims about using machine learning, what huge dataset are they pulling from when the pool of companies is tiny and their marketplace doesn’t exist anymore?

How is a VC meant to get VC returns from a company that is itself simply raising money and investing it in early stage companies.

This feels like clever self marketing (tech founder vs financiers!) when really it’s a pissing match between VCs


Be very, very cautious before ever taking VC funds. Unless you are a power plant, bootstrap.

Yeah. Diligence is 100% a two-way street.

Why would someone publicly post this letter, even with the redactions?

try and help others if you see yourself in the email



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