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Tuesday was my last day as CEO of CircleUp

405 points| rmason | 5 years ago |twitter.com

148 comments

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[+] rmason|5 years ago|reply
Here's the blog post that goes along with that tweet stream:

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

[+] xivzgrev|5 years ago|reply
Holy cow that feedback. It’s both great and awful at the same time. Great in that it was written as objectively as possible and concrete. Awful as in it was too long and he clearly put too much time in to it relative to how much the other guy valued him. I think the real purpose was to process his feelings and list out all the wrongs - I just think he should’ve separated them. Spend hours processing, spend no more than 15 min giving this jack off feedback.

Also hindsight is 20/20 but if you work with an asshole it’s not your responsibility to shield him. Escalate to the other board members and have them deal with him. He clearly values their respect so one of them (or better all of them) needed to sit him down for a talk.

[+] ilamont|5 years ago|reply
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.

The former CEO should take down the feedback email, as he is exposing himself and others to legal liability.

He is not the only one who has had to deal with toxic investors who sit on startup boards. It's driven many good people away from companies they've founded. Sometimes the toxic board members are not newbies, either - they're supposed pros. Not sure what sort of due diligence can sniff these jerks out before they join the board, and maybe it's not even possible to turn them away if it's a condition of getting investment.

[+] madrox|5 years ago|reply
Reading this is like reading about my own experience. I went through a similar period several years ago as an executive. I was leading engineering for three separate products and dealing with some very difficult stakeholders. I was also in a new relationship that I was trying very hard to maintain. The stress of all these things happening to me at once was colossal. I experienced a constellation of bad health symptoms. What I can't believe, in hindsight, was when I asked my doctor if this could be stress related. He asked, "do you feel stressed?" I thought for a second and said, "no."

I've never written anything about that time, despite wanting to, but this is the thread I wish I could write. Details aside the emotions are all the same. It felt cathartic to read this.

[+] noir_lord|5 years ago|reply
I had a business fail, an 8 year relationship break down (got cheated on) and in the middle of all of that they found a syrinx in my spine and a few months later I got diagnosed with Chrohns.

On my desk is a rock, just a hand sized piece of chalk off the foreshore near me but it has special meaning, I picked it up at 2am on the night I decided I wasn’t going to kill myself after flipping it from hand to hand for several hours while sat watching the moon on the water.

Now it sits under one of my monitors and when work starts to stress me out or life generally I pick it up and think back to 6 years ago.

These days my health is under control, the chrohns is stable, the medication works for quality of life, I have a good well paid job and I met the love of my life so between now and that beach is 6 years and a universe apart but man, you don’t see the signs until afterwards eh.

No one knows what the rock means to me, to everyone else it’s just a paperweight.

[+] jpxw|5 years ago|reply
What symptoms, out of interest?
[+] PragmaticPulp|5 years ago|reply
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.

[+] tschwimmer|5 years ago|reply
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-...

[+] khaledtaha|5 years ago|reply
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.
[+] maest|5 years ago|reply
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.

[+] sokoloff|5 years ago|reply
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?"
[+] blantonl|5 years ago|reply
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.

[+] aktxt|5 years ago|reply
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.

[+] ww520|5 years ago|reply
That's a very good letter. Very revealing at the board level. It's amazing how childish and unprofessional the board member had behaved.
[+] rajacombinator|5 years ago|reply
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.
[+] regularemployee|5 years ago|reply
I'm not a CEO, nor do the livelihoods of people depend on me.

But I feel the pain everyday of having to answer to my managers who are constantly asking for status on my projects. I care about my managers but I don't care about the projects. I hate my work.

There are so many things in life that I am curious about like singing, drawing, gardening, bird watching, etc. I'm not good at any of them (nor do I wish to be) so they won't bring me any income. Every day I put my curiousness aside to code some stuff to make my managers look good.

I can't quit my job to take a break because my wife and kids depend on my salary for money. My neighbors are suffering more because they are not in tech. They are trying so hard to have my life and I try my best to help them get into an industry I don't even like.

Money brings so much suffering and our entire society is built on it. Society is greedy and wants to expand infinitely too! Everything in nature must eventually be owned my someone.

It seems like the only way to escape is to become a CEO, make millions, and buy a bubble of eternal happiness as Ryan has done.

I hope I don't end up behaving like his former board member.

[+] howlgarnish|5 years ago|reply
Interesting read, but one thing that always strikes me reading this kind of story is how invested founders are in things that -- I'm sorry to say -- are not exactly earth shattering. I'd never heard of CircleUp before this, and their slogan "Creating a transparent and efficient market to drive innovation for consumer brands" still doesn't tell me what exactly it is that they do. Obviously they have investors and customers who found it worthwhile, but is it really worth sacrificing your health & family on this altar?

That said, I do wonder how Elon Musk, who's simultaneously trying to send humanity to Mars, convert the world to electric cars and solar panels, and create direct neural uplinks doesn't crack from the pressure though.

[+] daniel-thompson|5 years ago|reply
> That said, I do wonder how Elon Musk, who's simultaneously trying to send humanity to Mars, convert the world to electric cars and solar panels, and create direct neural uplinks doesn't crack from the pressure though.

Not to mention what I would consider the most important commitment for any parent: how does he find enough time to be a good father to his 6 kids?

[+] cwhiz|5 years ago|reply
I’d say Elon Musk has been acting more and more erratically as time has gone on. Just this week he changed the price of the Model S to a meme, $69,420. Seriously.
[+] fairity|5 years ago|reply
There's more to life than trying to improve the human condition. People value different things, and it's very possible he will proudly look back on his time spent on CircleUp.

Put another way, not everyone wants to do the same things you do.

[+] rexreed|5 years ago|reply
The world of silicon valley-style startups and tech entrepreneurship is so full of drama and intrigue. The entrepreneurship ecosystem is full of narcissists, blowhards, and self-important people who believe that since they are managing other people's money they therefore have more wisdom and insight than anyone else. Board members who feel that their role as board member grants them instant authority and credibility on all topics. CEOs who believe that their title means they deserve respect. And a range of hangers-on and wantrepreneurs who want to be part of the scene but have no real idea or knowledge on how to build a business.

Some startups are built to grow. Some are built to flip. Some will never go anywhere but fill people's pockets and egos. But many many more just fail.

There is little relationship between the alternate reality that is the startup world and the more mundane, sedate, and less interesting traditional business world.

Tweet storms and email chains like these read like the startup version of Jersey Shore or Housewives of OC.

[+] pembrook|5 years ago|reply
While I feel for the guy's struggle with cancer and the fertility issues he and his wife went through, I'm seeing the same tone in some of his other tweet threads (and threads from other people) and it's starting to feel like an intentional pattern done for audience building.

Which, I don't doubt he went through all this, but just can't help the bad taste in my mouth given the "I'm just selflessly saying things to help others" tone.

But hey, maybe I've just grown to be overly cynical after spending too much time around growth marketers.

[+] undecisive|5 years ago|reply
I'm equally cynical. But is it a chicken / egg question? Does attempting to be genuine, vulnerable and reflective lead to a bigger audience, or does seeing that the audience gets bigger as a result lead a person to be more genuine, vulnerable and reflective - to a point of artificial oversharing?

I guess the other question is... if there is good to be done, and being this kind of person causes a certain amount of help to hurting communities, does this form of vulnerability capitalism have a downside? (assuming its done with respect to the person's family and friends, who never asked to be thrust in this weird limelight)

And a question I often have to ask myself, what if it is nothing but genuine? How does one call out BS without trampling on the spirit of the genuinely hurting?

[+] nxmnxm99|5 years ago|reply
"Vulnerability porn" is an intensely annoying trend among Twitter tech personalities.
[+] mauritzio|5 years ago|reply
Eyeopening. When "follow your Dreams" leads to this....well did you really dreamed about it that way? Where is the fun? Looks like one becomes a "business" brainwashed robot spending way to much lifetime at doing ???????? just playing 'respect' to ego psychos for an in fact empty basket filled with $$$ paper.

Listen to signals your body sends, if there is no fun soon, it means STOP. Oh yeah you can watch datapoints, brainscans and talk to experts for years, but listen to what you feel is enough. It is hard to beat that "intelligence" sensor encorporated in the human shaped by thousends of years of evolution.

I wish this guy al the best, this maybe is the best thing he ever did.

I hope he can find back to a more satisfying life with lots of lifetime, enjoying doing fun things with his family!

No need to track down that destructive board member. He is sitting at work right in front of you on a basket with $$$, you listen to him as you think you need it for food and if you are priviledged for "dreams".. maybe just look in a mirror ?

[+] cthulhua|5 years ago|reply
Wow, this really struck home with me. I left a FAANG about a year ago to be employee #1 at a startup. 6 months ago, after some headaches and vision issues, I was diagnosed with a brain tumor. My work has been great through all this, but I can't imagine the additional stress of being a CEO whilst dealing with all that.
[+] remote_phone|5 years ago|reply
That’s terrible news and I’m very sorry for you. I hope your prognosis is excellent.
[+] tidenly|5 years ago|reply
The more I work in this industry the more I resent upper management and boards. Not just the guy he's writing about, but even just venture and this guy himself. Is this guy really contributing so much to society that it's just he has enough money to "call in the best doctors in the country" while the workers are left with squat? It seems like the people who work the least reap all the benefits.. Maybe covid's just got me being cynical though. I hope his prognosis is good.
[+] tpxl|5 years ago|reply
>It seems like the people who work the least reap all the benefits..

How exactly did the reading of this post make you conclude he did the least work?

[+] achillesheels|5 years ago|reply
You do not comprehend the concept of risk. As in, his life-continuum determined for him the affordance to seek the best treatment after compounding time in a direction you or I could never perceive. In fact, this is what makes entrepreneurialism so virtuous.

I am really starting to get agitated by this pettiness on HN. It didn’t used to exist in tech.

[+] ghiculescu|5 years ago|reply
I was wondering where I knew that name from... there's a module about Ryan & CircleUp in the HBS Disruptive Innovation Course - https://online.hbs.edu/courses/disruptive-strategy/

It was one of the more interesting companies profiled and I found the module very cool. If you read this Ryan - thanks for being part of it, and all the best for the future.

[+] luminati|5 years ago|reply
First thanks so much for writing this. The gilded world of unicorn CEOs seems all roses and wine from the Techcrunch armchair VC/outside world, so it was eye-opening to read an intimate account of the cold, brutal reality of being one.

That said, I have one question. What on earth was the co-founder doing? Isn't it the whole point of having co-founders so that you can share the trauma? Why did the CEO have to suffer through so much pain all alone?

[+] czbond|5 years ago|reply
From much experience with startups, founding and co-founding is a mental mind-f*ck at all times. Even founders of good companies are under constant stress to keep the thing proposed up. The stress and drama of running a company completely f's your world up long into "success"
[+] tzm|5 years ago|reply
> When at a board meeting at USV you stopped the meeting and said “guys we just aren’t focused on the right issues, this company has less than 6 months left.” One of the other board members said “ What are you looking at?” (You later realized you weren’t doing the math correctly).

This would be an immediate red flag. How do you handle this type of issue?

[+] Aeolun|5 years ago|reply
I always wonder why people use Twitter for these braindumps? Do these threads just lend themselves well to starting and typing until it’s all off your chest?
[+] kypro|5 years ago|reply
I quite like it. It promotes a concise writing style which wouldn't be as acceptable if it were on a blog without character limits.

Whenever I write something like this I've found I end up constructing each tweet a bit like a lengthy bullet point. I cut everything unnecessary and try to make my point as clearly as possible in as few words & tweets as possible.

When I write a blog post I naturally end up optimising for writing quality, and what could have been 5 tweets ends up as 1,500 words.

[+] cercatrova|5 years ago|reply
The audience is on Twitter. More likely to get engagement from tweets than via a blog post; because it's off platform, most people won't click it. There's also virality on Twitter from sharing specific parts of a thread in the form of retweeting and liking.
[+] he11ow|5 years ago|reply
I'm happy everything worked out for you Ryan. But I was left so queasy by this whole read.

This is presented as a victorious journey. By the end of it he's got his health back, his kids, an easy job, lots of money. The company's in good shape - everyone's a winner.

And you're telling readers - it's GRIT! I'm a super Gritter! I never give up!

Mate, you got so lucky, to be alive, to have kids.

Yet you lost years of your life, plus all your kids' early childhood fretting over terrible bosses. And by the end of it you're still wondering whether in future VCs will find you worthy of investment.

And in our day and age you're considered a winner!

You're the person YC points to and says - See him, you could be like him one day!

"Life, if you know how to use it, is long.

But one man is possessed by an avarice that is insatiable, another by a toilsome devotion to tasks that are useless;

one man is besotted with wine, another is paralyzed by sloth;

one man is exhausted by an ambition that always hangs upon the decision of others, another, driven on by the greed of the trader, is led over all lands and all seas by the hope of gain;

some are tormented by a passion for war and are always either bent upon inflicting danger upon others or concerned about their own;

some there are who are worn out by voluntary servitude in a thankless attendance upon the great;

many are kept busy either in the pursuit of other men's fortune or in complaining of their own;

many, following no fixed aim, shifting and inconstant and dissatisfied, are plunged by their fickleness into plans that are ever new...

Ask about the men whose names are known by heart, and you will see that these are the marks that distinguish them:

A cultivates B and B cultivates C; no one is his own master."

-Seneca, On the Shortness of Life

[+] duxup|5 years ago|reply
I don't want to digress too much here but I thought this was interesting:

> Believing that to attract a great CEO we would need more than two years of runway

What is involved in this process that takes 2 years?

[+] codingdave|5 years ago|reply
It isn't that the process takes two years - I'm guessing they were talking more about being a good career move for a CEO candidate:

A great CEO has many options in front of them of what to do with their career. Asking them to take on a company that doesn't have much runway limits the time they have to get in, become the new leader, and mold the organization. Therefore, it is not likely to be their best option, which means the candidates who are interested are more likely to be not-so-great CEO candidates.

[+] bishnu|5 years ago|reply
I think what he's saying is that no-one would be willing to take over as CEO unless they had two years of runway ahead of them.
[+] skrtskrt|5 years ago|reply
In addition to the other answers, it sounds like they knew they needed more time to execute & validate the pivot.

Let the original founder/visionary execute the pivot and then hand off the reins, rather than pull someone new in and try to brain-dump how you want them to pull off the pivot that mostly exists in your head.

[+] PragmaticPulp|5 years ago|reply
> What is involved in this process that takes 2 years?

He's not saying the process will take 2 years.

He's saying that no reasonable CEO will sign on to a company that is months away from going bankrupt. Two years of runway is long enough for a new CEO to find their feet, set direction, and work on profitability and/or fundraising.

If the CEO arrives with only a few months of runway, their first tasks will be to cut burn rate by laying off many of the employees. That doesn't create a good first impression.

[+] ProAm|5 years ago|reply
Twitter is the worst for long form messaging.
[+] danbmil99|5 years ago|reply
Is it just me, or do people in the tech startup world know this personality type all too well?

I see them as slightly less crazy, but just as annoying as our dear president. Hopeless narcissists who read Ian Rand and The Prince in their teens, and think of themselves as Tony Stark when they're really just Russ Fucking Hanneman.

[+] zcoelius|5 years ago|reply
The VC firm in question is trivial to figure out. Just look for a firm that had a board seat that is no longer listed on the site and that does not list Circlecup on their site.