Why Rand should take some money off the table

SEOmoz founder and figurehead Rand Fishkin wrote a typically transparent, thoughtful blog post about his struggle of whether to raise a Series B. He’s in the best possible position — the company is profitable and growing and doesn’t “need” the money, so with little dilution he could take $10m for safety, comfort, and scale.

By putting his emotions and financials out there — both business and personal, not that there’s a difference — he’s also opened himself up to armchair advisors such as myself and the great (and powerful) Dharmesh Shah, who heaped on wisdom and guidance in an open letter to Rand.

In that spirit, and because I’ve gotten requests for more articles about issues that arise after your startup is going strong, I wanted to follow Dharmesh’s lead and talk about of the questions from Rand’s post:

Should Rand take out a few million dollars for himself as part of this financing?

The typical arguments for: (a) reduce risk of ever getting rich, (b) you deserve it, (c) time-value of money, (d) now for the exit you want to “swing for the fences” along with the investors, aligning interests

The typical arguments against: (a) unfair to employees/co-founders, (b) now you’re not hungry so you care less, work less, (c) swinging for fences without attention to detail is imprudent.

All rational. But in the end, in a spirit of directness and with the greatest respect, I say:

Dear Rand,

Take some money off the table.

I will join Dharmesh and Brian Halligan in admonishing you that having $25,000 in the bank is foolhardy and perhaps even irresponsible. I’ll bet you $100 that no one at SEOMoz — not any employee nor any investor — thinks it’s a good thing or a good signal that you have no personal savings.

Devote all your waking hours to the company, yes. Siphon off money the company needs, no. But I’ll bet everyone at SEOmoz would actually be more comfortable if you had $1m in the bank right now.

It sounds like you won’t accept the “you deserve it” argument, so (although you do) let’s consider this from a cold, rational, economic business perspective.

You can’t have personal finance affecting your behavior or time-management at SEOmoz. If you paid a personal assistant to cause a sushi lunch to appear in your office, though it’s 15 times more expensive than hoofing it to the local sandwich shop, if it saves you half an hour of on-task time, you should make that choice. If you can spend $500 on a night out with the wife (babysitter + great meal + show) so you can be happier and more refreshed come Monday without any loss in time-in-office, that’s better for the business. If you can have a maid instead of scrubbing toilets on the weekend, if you can blow $20,000 on an amazing much-needed vacation (don’t you dare make the same mistake as me, Andrew Warner, and thousands of other type-A personalities that burn out only because they think stress and breaks are for losers), if you get yourself the fastest laptop and personal trainer and anything else that makes you a happier, stronger, better, and more productive human being, that’s all better for the business.

You also say that money is not the goal of all this hard work; in fact you tweeted recently that as you get older you want less stuff. (Me too.) That’s even more reason to take money off the table. Why?

Because even if (like me) you don’t care about “stuff,” there’s a base level of financial security that matters to anyone living in the 1st world. No house payments, never allowing price to matter for eating out or calling a plumber or helping someone less fortunate or putting kids through college or dealing with a surprise medical catastrophe — this peace of mind, this liberation is not to be underestimated, even if you don’t want “stuff.”

Since you don’t want to buy lots of things, that means that in an eventual exit from SEOmoz you don’t care whether your share ends up being $10m or $15m or $30m. All the same to you. All the same change (or lack of change) in lifestyle.

If you don’t care about even a 3x difference in the size of an exit, you really should take some money now: Get to that point of financial freedom ASAP since the penalty of doing so — reducing a possible eventual payout — is not an important penalty for you.

You worry that it will reduce your drive. But your drive never was about money. That’s why you only have $25k in your checking account — if it were about money you would have rewarded yourself accordingly.

You are like Michael Dell and Bill Gates and Steve Jobs and Warren Buffet and Sergey Brin and countless others who have achieved financial success so massive it’s almost impossible to wrap your brain around the implications of their net worth, and yet their work ethic, drive, and ability to innovate hasn’t flagged for a decade or more.

In fact, you’re already there! You already make enough money to do “whatever you want,” and that’s already not affecting anything negatively. Adding zeros to your net worth won’t change that day-to-day mindset, it’s just the prudent decision for your personal financial security.

So take it. Even if you don’t raise money now, still take out at least a few million over the next 18-36 months.

And congratulations in any case. You really do deserve it.

What do you think? Let’s continue the discussion in the comments.