new startup Ark was presenting in the TechCrunch Disrupt finals today. I asked them why they leaked acquisition discussions with Facebook to the press. It obviously makes them look more formidable, but it probably also pisses off Facebook.

They had a reasonable answer. But it does raise an interesting question - when if ever should founders leak stuff to the press? When is it helpful? When hurtful? A lot of founders are new to the "game." I think veteran advice would be useful.

I don't think I've ever leaked anything to the press (on purpose). Maybe I'm just not conniving enough.

What was their "reasonable answer"?

I think founders should leak things to the press as often as possible :-)

Ev - The answer was that it was already out there, although he acknowledged that it was probably someone on his team. Mostly I didn't want to focus too much specific attention on Ark. This kind of thing happens all the time.

I'm not a fan of leaking to the press strategy. I think you know my approach which is to be open in advance of your announcement with the person/ publication that you want to cover your news (if it materializes) - I did that with you twice on my two businesses (Sphere & about.me) and I think it made for a more thorough announcement.

Seems that most of what people "leak" has to do with funding and / or acquisitions. Generally my advice to founders would be that neither one is an event that you should be focusing on publicizing. Build a great product, give valuable members of the press an early look, treat your users well. The rest takes care of itself. Raising money, or being considered for acquisition, is just stuff that happens along the way.

Good advice, Tom.

Its highly risky in general. But press relationships are really important between a founder and a writer/reporter. I have brought a writer inside the tent on occasion and there is usually a quid-pro-quo (you can have the story so long as you "fill in the blank"). Not so much a leak as a briefing. Sometimes off the record, sometimes on.

A briefing has to support the company's goals. In this case I think the leak was fake. There was no real acquisition talk and they really didn't "walk away". So a lot of BS IMHO. This is bad for the company, the leaker and the writer.

ok a lot of "nice" answers here (keith, i don't think you're describing a leak), but it happens with some regularity, no? Personally I'm not a fan and have never leaked something. I've been leaked against - people who take what was supposed to be confidential and make it public. I don't talk to those people anymore.

for founders I'm guessing leaks fall into one of two justifications:

1) High impact enough situation to support compromising their morals. "oh, if this helps the funding close the leak is the lesser of two evils"

2) Balance of Power argument - someone has more power than i do/better relationships with press, i'm not going to get my POV across or a fair shake unless i leak this bec journalist will find that sexier and more likely to cover my perspective.

Mike - what has your experience been?

generally I think founders leaking stuff directly to press is high-risk, high-stakes poker. don't do it unless a) u know what you're doing & b) ur ok with potential negative fallout / ethical compromises. for most folks, I'd suggest only "off the record" commentary, or communication via trusted 3rd parties (but even those are high risk as well). otoh, agree with hunter prob only useful if you're in a reduced balance of power situation. or, perhaps after the info is already in the press anyway.

Hunter - my experience has been that a lot of people leak a lot of stuff for a lot of reasons. Most of the time I don't even think they quite understand what happens next. Once people understand the game they're much more strategic about it. One thing people must understand is they need a long term trust relationship with specific press individuals, otherwise they get crushed. Dave's last comment is saying much the same thing.

@mike - so a crunchfund company comes to you and says they want to leak something. What are the questions you tell them to ask themselves so they can decide if it's a worthwhile risk?

agree with Nike: building long-term relationship with press is important. you shouldn't risk investor or acquirer relationships but you should value the press relationship equally with other industry contacts. they will likely last far beyond just one company.

(oops agree with *mike*, not Nike ;)

Hunter - I handle it for them :-) I know if its a good story, or if it can become a good story with tweaking. And I can use my own trust network to help them, easing the transition. I can also give them guidance on the fallout (like talking about failed acquisition attempts) so they don't just end up closing a lot of doors by pissing people off.

@mike - at TechCrunch, did you ever advise a leaker that they should reconsider - that they really didn't want to make the information public - either out of concern for them or, perhaps less paternally, because you knew it would end badly for them and they'd be more valuable to you in the future if they didn't blow themselves up now?

Hunter - many, many times. :-)

Hunter - agree I am describing a different thing.... a controlled disclosure. A real leak (lets say a disgruntled employee trying to get revenge on an internal enemy or a ceo trying to persuade the world his company is hot by leaking a failed acquisition offer) is never good and I agree with the strength of your reaction. I recall one leak I did. I leaked internal realnames docs on my public blog to explain why the Microsoft-RealNames deal was ending. Mike will recall. I was angry. Not my best..

Wow what a wonderful conversation. I like the advice being offered so I will keep my comments short and sweet. I think things that are meant to be private need to stay private, for that is the construct of a relationship that spans years not a few days. So making their details public is not something that inspired that confidence.

Adding more...

The desire to share information can be presented in a constructive way by companies/startups through their own blog is a better way of doing so, because it is a constructive process.

I will shut up now.

I like your frame on this Om. I do agree that investing in relationships with reporters is really important (hi mike! hi om! hi matt! hi nick! hi alexia! hi eric! hi mg!) but my sense is that those relationships should be built on giving them legitimate insights into the development of your business and not on betraying the trust of some other party (acquirers, investors, partners, colleagues, etc) with a leak.

great point, Tom.

I wish I knew...NOW?

I am with my board member and pal Tony Conrad on the process. The problem for the era of massive startup growth is 'I need my attention' which leads to poor judgment as support from investors can't keep up with the pace of investing itself.