"There is a difference between doubt and an issue that can be resolved."

I agree that a doubt and an issue are two different things, however having a doubt is an issue in this context, and it should be acknowledged that some issues have the potential to be resolved (solved or disappear over time).

Because of this, I don't think dealing in absolutes is always warranted re: such dilemmas, though I do agree with your conclusion.

Agreed

I think conventional wisdom on this one suggests the answer to your question is "No".

Ultimately you do want that doubt to go away I'd imagine, so think to yourself, what are the steps that need to be taken for the doubt to disappear? Then ask, how likely are those steps to happen?

I can only speak from the experience of not having doubted initially but then beginning to doubt... I'm still with the same co-founder in that company as we were able to work through the specific points of difference, however I can say the result is a compromised experience compared to the original vision (at least on my behalf).

Nevertheless, it is one that has had positive benefits away from the specific company in question, inasmuch as encouraging me to adopt a broader perspective on where I'm looking to find fulfillment (of various kinds), which has in turn ultimately led me to start a second company which I'm more passionate about, has a more favourable business model, and is the one I want to spend most of my time towards.

i.e. depending on your nature, there are positive externalities that can come from sticking it out, and it may actually work out holistically for the better.

That being said, it's a matter of probability; in all reality, the arrangement won't be ideal and the only value you'll extract from the process is that generic/ubiquitous 'wisdom of failure'.

Whilst I was writing the above, I recalled a more pointed answer to your secondary question -

It's probably not quite the kind of "doubt" you reference, however Max Levchin at Startup School recently referred to having a scintilla of such towards Peter Thiel when they were first kicking off PayPal. This doubt was engendered after Max was abandoned in a carpark with an empty car battery by Peter who seemingly didn't really care too much for his welfare (I personally wouldn't consider Max referencing a deep-seated sense of doubt, but maybe that's all that you're referring to)... I think by all measures, things worked out fairly well thereafter... ;-)

If you haven't watched/listened to it already, worth the time for the above and other amusing anecdotes/morsels of wisdom: http://www.justin.tv/startupschool/b/298808490

that's the video that prompted me to ask this question! Max also said, 'Where there is doubt, there is no doubt.' which I generally agree with...but maybe entrepreneurs have a tendency to believe that they could be the exception to any rule.

Well, without wanting to regurgitate that which has become trite, it has been acknowledged that a little delusion-masked-by-confidence in an entrepreneur isn't an entirely bad thing!

Completely agree, and for that reason I started a meetup here in London recently called London Tech Founders Anonymous (http://www.meetup.com/LTechFA); we've had two great sessions thus far, and indeed as you've noted, one of the points raised in support of the initiative by attendees present at the inaugural session was the liberation of the format due to the group's aims; viz., steering participants away from the ubiquitous "We're killing it!" in favour of actual truth and deeper bonding/learning that, in my opinion, seems underserved in the community generally.

That being said, great initiatives like FailCon (http://thefailcon.com/) do exist, however I personally don't believe a consumption-centric format (i.e. standard lecture/conference/meetup format) will cut it; deep interaction and open sharing on a regular basis is the only way.

We in LTFA adhere to Chatham House rules (http://en.wikipedia.org/wiki/Chatham_House_Rule), so there is confidence when unburdening ourselves... and that's a big part of it, tbh!

Re: your comment around destroying agencies, I disagree inasmuch as believing the forward thinking agencies are/will actually spawn their own IP divisions, and thus feed into the startup scene in the future.