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The 6-page e-mail sent to the difficult former board member is interesting: https://docs.google.com/document/d/17tEc9ETL4tjfTmNbpwJJ5OSx...

Given that he posted the e-mail contents online and wrote it in a way to narrate the board member's own bad actions, I'm assuming the real intent to was to warn others against working with this person. He stops short of naming the difficult board member, but it wouldn't exactly be difficult to figure out who it was from all the clues.



Some people are agreeing with you, but I actually don't agree. I looked into this and it's actually quite difficult to definitively identify who is being referenced. There are a few seemingly conflicting bits of info in the letter, like the person is a novice VC investor ("I recognize ---- is your first experience in venture, or as a professional investor") with the fact that they are also the lead investor in one of their rounds ("I still can't believe that is true for the lead of our Series ---"). As far as I can tell, these seem to be mutually exclusive: the leads of all the rounds seem to be veteran (or at the least very seasoned)VC investors.

Theoretically this would be easy to figure out if you had a yearly listing of board members which I imagine should be public, but that doesn't appear available publicly. The only listing of the board I can find is this news article [0] from 2015, but again, none of the people listed there can be definitively identified as the one being referenced.

As further evidence of how murky this is, several people in the comments below have named different people as the person being referenced. One commenter has edited their comment to change the person being accused.

If the author of this email wanted to point a finger at a specific person, they did a bad job.

[0]https://www.crowdfundinsider.com/2015/01/60650-lending-club-...


Hopefully this reply doesn't get me in trouble on HN...

But I strongly disagree with you.

Collaborative Fund led the Series C round. Jay Kim was a fairly fresh venture investor at the time; the model and operation of NXC/Nexon's investment arm was quite different to the traditional VC. Based off the timings, it's highly likely this is the VC who the e-mail refers to.


https://twitter.com/ricburton/status/1316945844315238401?s=2...

sounds like Craig Shapiro is the likely culprit here


Very doubtful. I think you misunderstood the tweet; the person who posted that tweet is asking the founder and leader of Collaborative Fund to be responsible for the actions of his partners. Craig isn't the one who was sitting on the board.


nope. He confirmed its him but denies the accusations https://twitter.com/cshapiro/status/1317212694529802242?s=20.


I agree. I also tried to figure this out and couldn't narrow it down to a single person.

However, while the lead investor companies are established, the "partners" of the lead investors listed on crunchbase do seem to fit the fresh investor note. Especially since Series B and C were 5-6 years ago.


Mmm, yeah. I wasn't considering the series C because the timelines didn't really add up, but I took a second look and it actually fits the points in the letter.



An extra bit of complication seems to be that CircleUp itself seems to be some sort of VC-like operation, so at times I wasn't quite sure if some of the funds they were raising were for CircleUp or their clients.

Time to rewatch Inception.


Three names have been named. Two of the names are from the same throwaway account (unless something was changed with edits).


Let’s not do that. I’m incredibly appreciative of OPs transparency here. As a person who is susceptible to the same degree of stress and mental health toil, let’s not make the story about the investor but rather around the stresses of being a CEO.


You can't control what people are interested in, what they want to know more about.


I bet Facebook executives beg to differ


Sure you can, to a degree substantial enough to afford the entire advertising industry.


I agree that the problematic investor shouldn't be outed here. The investor isn't here to defend himself, and outing him will cause him irreparable (and perhaps undue) reputational damage.

[edit] Is giving the accused a platform to defend himself that unpopular of an opinion? Online shaming often gets out of hand and goes too far. I recommend this TED talk: https://www.ted.com/talks/jon_ronson_when_online_shaming_goe...


What forum should he be outed in exactly?


There are a couple options that come to mind:

1) Contact the accused party and ask him for a written response. By giving him the opportunity to defend himself, you get a more balanced view and decrease the likelihood of cruel & unusual punishment.

2) Out the investor in private forums where data/information that arises after the publication of this article can be fully considered. YC and many other founder networks have investor databases for this purpose.


1 isn't a terrible idea in most circumstances but with investors you're more likely to get a C&D than a fair response given the line of work and the importance of reputation to the process.

2 - no, I disagree strongly for two reasons:

Keeping information in a quiet private forum makes it inaccessible to people at large. This means the next CEO who runs up against this investor is mostly completely unaware of their past actions.

And, honestly, hackernews is probably the single most relevant forum you could find to discuss this on - it has a general lean toward tech but it is run by ycombinator which is specifically interested in all things investment.


> Keeping information in a quiet private forum makes it inaccessible to people at large. This means the next CEO who runs up against this investor is mostly completely unaware of their past actions.

I agree this is the downside of my proposed approach. But, the alternative is a world where someone's reputation can be irreparably damaged by unsubstantiated claims made by one person.

Do you want to live in a world where someone's reputation and livelihood can be destroyed by unsubstantiated claims? You may think I'm overstating the potential damage, but I think people generally underestimate the damage the internet mob can inflict on a person.


There are some societal tools that exist to fight against baseless slander in a public forum but, tbh, the US has resisted adopting those.

I would rather live in a world where the powerful can be baselessly attacked compared to a world where the weak are unable to fairly attack them - if we need to err on one side or the other I prefer to put up with trolls and scammers.


Except the powerful will simply use those tools to baselessly attack the weak especially those that pose problems to them. They, after all, have the money and influence to pay for much more professional attacks than the weak can scrounge together.


I don't see this as a case where a weak party is unable to fairly attack the powerful.

Even without outing the investors, many founders are currently doing the necessary research to identify the investor and will blacklist him.

I think we should keep in mind that:

1) The accusations are currently unsubstantiated

2) The reputational damage to the investor is already significant and largely irreversable

3) Outing the investor here will significantly increase the reputational damage to the investor

Given the above, I really don't see how it's fair to out the investor before substantiating the accusations or giving the investor time to respond.


This is similar to how priests were quietly shuffled around parishes. Yes, the priest's activity were criminal so it's NOT 1:1 of a comparison. However, keeping shitty people protected by keeping the info private does nobody any good

EDIT: left out the keyword NOT in the 1:1 comparison


> Keeping the info private does nobody any good.

I'm saying that we should keep the identifying info private until the accusations are substantiated.

The internet mob is merciless, and will very likely ruin this guy's reputation once he's outed.

By outing the guy, you are presuming him guilty and inflicting steep punishment when he could be innocent.


> I'm saying that we should keep the identifying info private until the accusations are substantiated.

How do you substantiate an accusation like "you insisted on talking to me at 3AM local time after I just stepped off a plane after a 18 hour flight" (or whatever the deets are)?


> By outing the guy, you are presuming him guilty and inflicting steep punishment when he could be innocent.

In general, yes, but in this case the most convincing candidate is a billionaire. He'll be fine.


The author didn't out them, and they were the people that feel wronged by them. Why do you feel the need to do what the author chose specifically not to?


Why not both?


Well. It seems like you can't narrate the latter without the former. What would you propose?


It's clear that people in the industry will be able to figure out who the letter is addressed to - and I would be surprised if the CircleUp CEO didn't realise this. So the censorship is mostly for show.

The fact that the VC isn't named, makes it difficult for them to reply in a public way and respond to some of those points.


It seems like if many people don’t know, then it actually makes a difference that they don’t know. I don’t know the details but it seems possibly important, not just for show?

See: https://en.m.wikipedia.org/wiki/Missing_stair


> and I would be surprised if the CircleUp CEO didn't realise this.

That was the point I was trying to make:

The CEO went out of his way to make the board member as easy to identify as he could, short of spelling his name out.

I'm not suggesting that people try to reverse engineer it, but clearly the open letter was meant to be partially retaliatory and partially a warning to others in this space.


Given the timeline, that he was lead investor, the name length, the experience of the VC, the current and past board members, it’s easy to figure out the missing name. https://en.m.wikipedia.org/wiki/CircleUp Confirms the name which would also fit in the redacted parts of the email.


If you highlight the name, the highlighted text is {{14}}. I don't think the lead investor's name is necessarily 6 characters. FWIW, I was deeply curious about who the investor was and spent some time investigating who lead the fundraising rounds on Crunchbase, but I couldn't narrow it down sufficiently.


I got curious as well.

One of the funds mentioned in the wikipedia article and that also matches the description from the email removed CircleUp from their portfolio website in 2019. You can look it up on the Internet Archive.


thanks, I was able to figure it out.


Where are you seeing the current and past board members? That’s what I’m trying to diff against but I can’t find good sources.


Not just for show; doing it this way likely spares that person's SEO.


Aren’t Google Docs unindexed unless published to the web not shared as viewable links?


I suppose so. I was thinking more along the lines of his name not appearing in this discussion's title means people searching his name might not find this discussion.


I think just publishing the event without posting the email leaves enough of a trail for another CEO to reach out and ask "Hey, we're going to work with XYZ and know he used to be on your board. Any advice for us?"


Nobody likes to date people who are always trashing their exes. Board members end up choosing the CEO, do they not? There are degrees of dirty laundry airing that could end up burning bridges with people you've never even met before.

Meanwhile the next CEO knows there's a rat, and can work out for themselves who that might be before their first 100 days are up, by which point most managers have been typecast. After that it's very hard to fully take advantage of major new insights you've had. It's an uphill battle to make major changes to your style of management.


Nobody likes to date people who are trashing all their exes but one is fine.


Fair enough. But you also are careful when they trashed their last ex.


Name the board member. The former CEO can be dignified by keeping his name confidential , but this is a founder and entrepreneur discussion forum and this deserves discussion about this individual. It is also relevant to the story.

There is absolutely nothing wrong with knowing about, and discussing who it is and possibly who else has had the same experiences - as long as it isn’t mudslinging but a professional discussion. Similar to the letter.


>> There is absolutely nothing wrong with knowing about, and discussing who it is

You should keep in mind that the investor may actually be innocent here. Imagine if the CEO was a sociopath who is both adept at manipulating public opinion and out to destroy the investor's reputation.

I'm not saying this is fact. I'm saying it's possible.

Outing the investor here will cause significant, irreparable reputational damage to the investor.

Given that the accusations are based on unsubstantiated claims, outing the investor is wrong.

Please don't underestimate the consequences of your actions. You may see it as just 'discussing some random topic on a forum'. But, doing so could be ruining an innocent person's life.


Naming the investor is counterproductive.

Bad investors, bad board members, and even bad incubators are a dime a dozen.

Naming this 1 investor focuses the discussion on that single investor, rather than bringing awareness to the situation itself, and how commonly these things happen (yet how rarely anyone talks about it).


Indeed. It didn't take me long to figure out who the seeming douche bag of an ex-board member is, despite being half a world away from the US and Valley intrigue. Yet, if Ryan Caldbeck chose not to name and shame, it is not my business to out someone.

I liked someone's comment about preferring to let the focus be on Ryan's journey, and I suppose that many others here must be feeling a sense of kinship with a fellow entrepreneur as he described candidly and courageously his version of "The Struggle."

Sure, so that the lesson isn't lost, though, we may want to learn from Ryan's sobering experience and think harder about this too: Which investors we choose to collaborate with, come due-diligence time.


That's a very good letter. Very revealing at the board level. It's amazing how childish and unprofessional the board member had behaved.


Meh. I read this as a bunch of whining that reflects poorly on the CEO. He even admits to taking this investment and giving up a board seat without ever meeting in person. Embarrassing frankly.


Yeah, totally right! All those personal and health issues... How dare he whine about it now. Like as if he is some sort of... oh i don’t know... a human being with emotions and feeling. Gods this is CEOs have become now.

EDIT: #sarcasm if it wasn’t obvious.


I’m referring to the letter to the board member itself, which apparently wasn’t #obvious to readers on HN.




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