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Experienced VCs would have fewer issues, e.g., over the years on lots of Boards have learned a lot about being a BoD member while avoiding really big Board fights.

Some of what worries me is what I've experienced with VCs so far -- we're not even on the same planet.

E.g., if the business goes well, then soon I will come to the Board with a project for some ad targeting that makes crucial use of the data only we have. The targeting has a shot at being better than what is in the industry now, primarily because the data is different (unique) and we can have better applied math for processing it (uh, my applied math might not apply well to the data, say, our ad networks have).

Why better data? Uh, as above, the data is from those on average 20 Web pages each user sees and the data they enter in response. For more, that data is from the moment and focused, actually usually uniquely well focused. E.g., I may not know what the heck the user had for lunch, but I've discovered that that he's just dreaming of breakfast with apple-cinnamon oatmeal tomorrow, just tomorrow. Presto, bingo, slam, bam, thank you Ma'am, the user gets an ad from General Mills. But it only works just then, and is useless in 24 hours.

So, I come before the BoD with this new project. For the quarterly budget, the BoD will have to approve the project. I'll direct the project but only loosely since I'm still busy being CEO. So, I'll have to hire, basically some good applied mathematicians. There will be some math, maybe some new math, but also a lot of data handling, e.g., digging into the many terabytes of the Web site log files. Might have to write some one-shot code.

The project will likely go for several quarters. The project in total can blow $1 million, more than once. Like most Ph.D. dissertations, it won't be clear just how well it will go or just when it will be done.

But, since the BoD has to approve the budget, they will have to approve the $1 million, some number of times, for some number of quarters. I have in mind roughly how to do it now, but I won't be able to stop my CEO work and will have to hire for 99% of the work.

So, I try to explain to the BoD how the project will go.

Tilt. Halt. Alarms go off. The BoD doesn't like it. They have a fiduciary responsibility to the stockholders, including themselves. No way do they want to spend $1 million at a time, at a pop.

I saw such BoD resistance at FedEx. It was about to kill FedEx. I was the guy who did some computing with a little math that turned the BoD around. Founder, COB, CEO F. Smith said at a senior staff meeting that my work "solved the most important problem facing" the company. Yup, I saved the company from going out of business, literally.

But to me, the FedEx BoD was just bonkers; there was no good reason for their resistance. They were foolish. They couldn't see rationally as far as their hand in front of their face. It was worse than trying to teach the family kitty cat to use the toilet in the garage workshop.

So, on my startup now, as CEO, trying to teach the BoD, I take out full time for half a week, put together a good tutorial dog and pony show, and try to explain what the opportunity is and how the math will go.

There's no way I can explain the math itself directly. Even among Ph.D. math profs, fewer than 10% have the math prerequisites. Among Ph.D. computer science profs, fewer than 1%.

So, since I can't actually use the math, I'll have to work just with analogies and draw some cute pictures to be seen just intuitively.

Maybe I'll get lucky, take a very simple, basically just a first-cut guess, at the math (remember the targeting math is not all done yet!), take some data from the log files, write a little prototype software, get lucky, and show that the targeting works better, say, goes from the Mary Meeker's $2 per 1000 to $4.25 per 1000. Uh, with everything else constant that more than doubles revenue. And, if that works for ads based on actual sales, the result, for those ads, could go to IIRC ballpark $50 per 1000.

That work could take me longer, maybe three weeks away from my CEO duties. I'd have my door closed, and when the COO, head of HR, Chief Counsel, and CFO pounded on the door, I'd have to tell them to work it out on their own.

So, the big day comes, and I pitch to the BoD. Soon they start looking at their smartphones. There is little so painful as listening to an advanced math lecture where don't have even a clue about even the basics, especially when are supposed to understand the stuff, even when I try to make it easy. The first BoD Member gets an urge, soils his chair and the carpet as he rushes to the men's room. Soon I'm the only one in the Board room; all the rest of the BoD has visited the men's room and retired to a bar down the block. There I get a new title, Senior PIA, pain in the ass. The ad targeting project is cancelled. All the BoD Members are pissed.

Later the rest of the BoD Members meet and can't decide what to do, and I've got a big BoD fight on my hands. All the rest of the work stops to settle the BoD fight. The company ship is starting to leak slowly.

So, BoD squabbles.

"Partners"? The famous co-founder disputes, e.g., with the usual, some chance of a nice short term gain but with a risk of a long term loss, say, a big anti-trust issue, a user privacy issue, some accusations of collusion in restraint of trade, pissing off some EU regulator. So, make some extra money for six months and then work off and on for years trying to clean up the mess.