"Writing a plan makes you feel in control of things
you don't actually control" Jason Fried
We were trained in the industrial age to think in terms of fitting people to roles, not the other way round. This was based around factory jobs where a person had to interface with an inflexible machine.
Even in that age it was the wrong way to hire knowledge workers. The person who knew a lot about how to do X, but was hired to spend their life doing Y was likely to be unfulfilled and to produce a worse result for the company than someone who had a passion for Y. When you multiply that up to, say, 5 skills, you realise that 20% or more of most people's potential was wasted.
It most certainly has no place in a modern startup.
I liken it to internet dating.
There are people who create a complete checklist for the person they are looking for.
They've defined themselves and their ideal partner.
Those people fail - bigtime.
There is one thing which must unite the founding partners - passion.
There is a second thing which is vitally important - availability.
And a third - financial expectations.
Everything else must fit around these.
By deciding "I need a co-founder CTO or CMO with skills X, Y and Z" you set an impossible task.
By sharing your idea and attracting people who want to help, your chances for success are far higher. They will have passion and availability.
Then look at the skill sets and see who can run with what. How the skills overlap, where the gaps are (including yourself). Who could learn and grow into a role. Who has a passion for which area. And don't restrict yourself to four founders, or even to full-time partners. Take on mentors, advisors, people who'll help part or full time or even just pass your leads. And build a team with overlaps so when one drops out it doesn't kill the project. You're after a buzzing community of ideas and people who can make them happen, not an industrial corporation with fixed roles and a blame culture.
But don't forget the financial expectations. You are trying to trade off real time dollars today against a lottery ticket on the future. You are giving away a large portion of the money you can make because you want to attract the best people but can't afford to pay them.
So put funding higher up your agenda. Find a way to get enough money in to pay people, rather than give away equity. And certainly don't give it away on an arbitrary basis.
If you really need this person who is part CTO, part marketing and part whatever else, then offer what it takes to get them on board. Then fit the team around him/her.
If you really need an investor they are in charge. You don't dictate the equity - they do.
One last thing. John Cleese put his success down to rejecting the first funny thing he thought of and working toward finding the deeper one - the one others hadn't thought of. The same applies with startups.You are aiming to find the people who really make this fly. The difference between the best ones and the normal people you find everywhere is probably an order of magnitude on the bottom line - a billion v a million.
Are you really going to cut this super guy who will transform your startup off, just because you will only offer 16.3%? Are you really going to turn down several million in investment because they want 20% instead of your 16.3%? Of course not. So why create these rules for yourself in the first place - it will only make you dissatisfied and insecure (I gave away more than I should have so I'll have to make it back on the next hire).
My rule is simple. Leave 80% for investors (1st, 2nd and 3rd rounds). Share out 20% among co-founders. If they feel the company is going to be big, then that's still good enough to bring them in - 5% of a billion dollar company is still a lot. Only if the company is small, does 30% v 50% matter. And that's not what you're planning - right?