Those aren’t my words. They were spoken by John D. Rockefeller who, if memory serves, knew a  little bit about business. And, although I’m not a fan of billionaires past or present, I do find profound wisdom in JRock’s words. You see, I’ve started, and conducted, business with friends and it’s almost always gone south.

While Ed and I were friends when we started Peppercom, it was a business friendship that had been forged through the ‘Romper Room’ days of Earle Palmer Brown and the Kremlin-like autocracy of Brouillard. Just like some of the case studies mentioned in Malcolm Gladwell’s amazing book, ‘The Outliers.’  Ed and I had probably already logged some 10,000 hours of working together before we ever hung up the Peppercom shingle. We may have been nascent entrepreneurs, but we were tried and tested public relations executives.

Compare that example with the several times my friend, Tommy, and I have tried to help each other out in business. Thos, as he is also known, reached out to me first, hiring my firm to do some corporate ID/branding assignments for the credit union he was running at the time. It started out well enough, but soon I was receiving some rather unpleasant calls from Le Poer (another one of Tommy’s monikers) questioning an invoice. The situation quickly escalated and we agreed to disengage. Now, fast forward to a time when I was able to reciprocate. It occurred when Ed and I started our very own dotcom firm, called PartnershipCentral. This was at the height of dotcom mania and, like everyone else, we figured we’d be multimillionaires within a few months. So, Ed spun out of Peppercom to run P’Central and hired 26 souls to staff it (a ragtag bunch if ever there was one, BTW). TLP (yet another one of Tommy’s aliases) was one of the few, decent employees we hired. If memory serves, he headed up research. But, when the dotcom bubble burst, guess who had to be laid off along with 25 other luckless people? Tommy. And, while it didn’t damage our friendship, it certainly didn’t help either.

I’ve also crossed the line with Dave Mandell, a good friend from long ago who resurfaced to hire us. Having Dave as a client, no matter how well he treated us, nonetheless put a strain on a friendship that, happily, remains very strong.

Ed’s done work with more ‘friends’ than me. In fact, his extended network of friends and contacts has become affectionately known as The Moed Mafia within Peppercom. It’s been the source of some great new business (as well as some totally bizarre dead ends). But, I’ll leave it to him to comment on whether mixing business and friendship works. I don’t think it does.

That said, I sincerely appreciate new business and prospective employee leads that come from my friends. But, I’ve learned enough to know by now that I’ll never cross the line again. JRock’s words are spot on: a friendship founded on business is better than a business founded on friendship.