"why would have he not only given advice but invested in the company"

First, let's get your facts straight: I have not invested a penny in Groupon. I haven't put any personal money into any private company other than my own. I was awarded options as compensation for participating on the board, just as other board members were.

Why did I give them advice? Because they asked me for it and I thought I could help. A lot of people ask me for advice, and i'm happy to help where I can. I don't have to agree with someone on everything to give them advice. I like Andrew, he asked me to help him, I wanted to help him, I'd never served on a board before, so it sounded like a great learning experience. It was - I don't regret the experience at all.

Andrew knew where I stood - and where I stand - on VC, investments, growing quickly, hiring a bunch of people, etc. He was interested in my perspective on product, design, and user experience, not on financing, growth, etc.

I was asked to leave the board in 2010.

^ is what I love about HN.

Is it better to stand by and let them get on with it, or to join them and provide a different opinion? A counterbalance?

I'm in the second camp; work with people, spread your ideas. Give it a try.

Of course I'm also of the opinion that, at board level, it's healthy to have a range of opinions. Only then can you make informed and reasonable decisions.

For the observant (or the fellow Hollanders), we call it the Polder Model (http://en.wikipedia.org/wiki/Polder_Model).

> at board level, it's healthy to have a range of opinions

This is very true... perhaps its one reason why Groupon is struggling so much. Without knowing the board dynamics, its impossible to say, but if I was in their position, I'd want people on the board criticizing every move. So long as it wasn't a majority of the board that is...

I thought your prior response (linked to by the comment that started this digression; "453 days ago") was sensible and sufficient. But thanks for chiming in again and definitively.

I am having a hard time following this comment. Are you suggesting that Jason Fried doesn't run 37signals in the manner he's talking about here? If so, then on information & belief, you're wrong.

If you're just saying that you think owning equity in a company not run the way he runs his own company undercuts everything he writes... ok, but what a boring objection to raise.

A board seat is a lot different from just holding equity. I own HPQ, RIMM, and YHOO, and if I had a board seat in any, my push would be for sale and getting rid of everyone above the first layer of management and engineers. (Boardmembers can't do this directly, but can work with shareholders and management, and ultimately hire competent CEOs)

And? It's not like we have to read tea leaves out of his board memberships to see how Jason Fried runs a business. He runs a famous business himself.

It gives an unwarranted endorsement to GRPN; their business practices are fairly reprehensible, so if a marginal investor or marginal small business customer gets screwed because a well respected guy lent credibility to their board, it's a poor choice for him.

Do you really believe any of this comment? You're a pretty smart guy. I don't believe you think anyone reads this article and thinks Fried is saying Groupon runs that way, or that Fried is in any way endorsing how Groupon is run.

I know this is a message board and we're all committing message board thinking, but snap out of it for just a second.

We're talking about a real person --- a person who by the way is posting on this very thread --- who runs a real business. From what I've seen of that business, it runs, successfully, the way he describes it. I wish we'd stop talking as if Fried was Chairman Mao and we're really debating global communism.

Not based on the article at all -- just the general argument of "someone holding a board seat at a company is more of an endorsement than merely owning stock". There are people I respect who have board seats at really dysfunctional big tech companies, too, so maybe the argument doesn't work.

He's a great CEO (at least in the context of 37 Signals), and has a set of values which are internally consistent, and sits on a board of a company which is inconsistent with those values. I'm not sure how to reconcile this with my belief that boardmembers have a responsibility to exert governance and oversight over their companies.

Based on reading his responses elsewhere in the thread (left the board in 2010, was his first board seat, novelty, etc.), it makes more sense. I guess I am overly sensitized to passive board members from watching HP, Yahoo!, eBay, RIMM, etc.

He does not sit on the board of Groupon and hasn't for a long time.

Right -- so this whole thread is essentially people trying to troll him, which I didn't understand until reading the rest of the context and postings on other 37S articles. (and Groupon early days was fine). I assumed it was brought up because it was relevant to now.

You're just a little obsessed with parsing his every word. Maybe he did find Groupon's growth absolutely disgusting. Maybe he didn't. Either way, he was asked to participate and give advice, which is what he did. One can do that and not be thrilled with everything going on. We're not talking about criminal activity here, just one of many ways to run a business.

A bit confused why downmodded for responding to a request for clarification with a clarification. If you don't like the original post, isn't downmodding that enough for you?

He didn't invest in the company. He was granted shares. He sold them at his first chance.

Thing is Jason is all about living the good life not being rich. Good life != rich. He was doing well for himself before Basecamp and Basecamp was just part of his strategy to manage his own work more effectively so he would have time for stuff that is actually better than coding or designing - like spending time with family or driving race cars a la DHH.

"why would have he not only given advice but invested in the company?"

On the link you posted he mentioned that he hasn't invested on the company, and that the options he sold were ones he received as compensation for his work on the board.