For some strange reason, it's easier to see what you did wrong last time round than what you did right. I'm sure me and my team must have done a few things right as we ended up being acquired (to use Dharmesh's term, in a modest liquidity event), but I'm painfully aware of the things we did wrong:
The fact that Microsoft produced such a thing a few years later meant that maybe we had great vision and insight, but trying to do in a team of three devs was just plain stupid. So the lesson there is avoid over-engineering.
In the seven years between incorporation and acquisition we took on tons of consulting work just to pay the bills, much of it unrelated to our product. In the early stages if you're self-funded, this is almost inevitable, but once you have a product, then you should make sure that any other work you do supports your product strategy.
By this I mean that, for example, when they come with a feature request for a specific client in order to clinch a deal, then it's good if the business has the capacity to digest and deliver that - we were always flat out working on the the next big thing that our sales guy always had to make do with what he had. (I'm not saying throw your product management process to the wind, but just try and be a bit flexible in support of the sales process).
Interesting your comment about founder health - there is something recent on this subject on Jason's blog I believe - I wonder if we are coming into a new generation of entrepreneurs where maintaining one's health is seen as a fundamental pillar of successful leadership. I certainly didn't do myself any favours first time round and have got quite some catching up to do before I turn fifty :-).
Several things come to mind:
This thread is in a similar vein:
http://www.brightjourney.com/q/entrepreneurs-3-best-pearls-wisdom-received-startup-ventures To me what I learned is to focus on the product and demand. Anything else should be minimized. Ultimately how are you going to drive the revenue. And how are you going to get the product to be what it needs to be to make it marketable and sellable. Questioning everything I do and figuring out how it ties back into one of those two things.
As a marketer at one startup long ago I got caught up in the brand and logo and and this and that, losing sight of the need to get money in the door. Now I am a huge brand advocate and believe it's a part of the equation. But as a foundation, how are you going to make the money.
My answer is based upon my current company, which is a very low-tech, locally-focused healthcare services company. In that context, at least, I would do these things differently if I were starting it over again:
1) Hire a great salesperson ("great" depends on a lot of factors, which would be different from one case to the next) from the beginning.
2) Focus on profitability. "Happiness is positive cash flow, all else will come later".
3) Build a well-grounded strategic plan, and track your performance against it often, adjusting course as needed and paying CLOSE attention to the details. Be very honest with yourself about where you are succeeding and where you are not.
4) Hire slowly and carefully. Fire quickly when realize that you've made a mistake in hiring. Get it over with and move on.