When is it riskier to not take risks?

In my free time, I like to play Texas Hold'em poker online, generally for the smallest amounts of money possible: $0.02 big blinds, and about $4 a game. I don’t do it to get rich. I do it to train my mind to get better and better at assessing risk.

Every poker player knows it’s a long game. You don’t win at poker by banking on a royal flush. I think I’ve had a royal flush exactly once in my entire poker playing career, and it was on a hand that I folded relatively early. The odds were not in my favour.

When you’re at the table, every round is a game of risk calculation. The winner is generally whoever calculates risk the best over the course of the entire game, or over several games in a tournament

But sometimes, the cards are just not your friends. Hand after hand, you get total crap. As you watch your stack of chips dwindle, and watch the other players stacks grow, you eventually get to the point of no return: You’re going to lose unless you do something drastic.

Maybe you get lucky and have pocket aces pre-flop. This is about as strong of a starting hand that you can have, but it still loses a shocking amount of the time. After all, it’s nothing more than the best possible pair. Any three-of-a-kind can and will trounce you.

But the writing is on the wall. If you don’t do something dramatic, you’re going to lose.

So you push your remaining chips into the middle. You go all-in. If you’re lucky, a few other players call you on it, and now you have a chance of getting back in the game: If you’ve got the strongest hand by the time the river lands, if no one managed to get anything better than your mere pair of aces, you might double, triple, or quadruple your stack (depending on how many players called you on it).

It’s a bet-the-house kind of move, but often it’s enough to turn the tides and allow you to go back to taking more calculated risks.

Great, thanks for talking about poker. What the actual fuck does this have to do with marketing?

When you’re an entrepreneur, you’re also in the business of assessing and taking calculated risks. When things are going well, you don’t want to go all-in.

But if you’re the underdog, if you’re an insurgent, you may find yourself in more bet-the-house moments than you’d like to admit.

Your opponent has a million dollars in advertising to spend, and you’re down to your last twenty bucks. You haven’t paid your utility bill in months. Your creditors are calling. Your employees are threatening to walk out. And you need to do something drastic.

It’s in times like these that you have to do something big. You can’t outspend the competition. But you can do one thing they can’t: You can tell a better story.

A great story spreads faster than a big ad spend.

Great stories always involve risk. If you tell the wrong story, you’ll not only fail to gain new customers, but you’ll lose existing ones who think you’ve lost your goddamn mind.

When Old Spice was being relegated to the discount isle at the local Piggly Wiggly, they told us a story about the man your man could smell like. It spread like wild fire. Talk shows, news programs, and social media exploded as everyone competed to be the first to share the story or give a hot take about it.

When Dos Equis was a completely unknown brand, they told us a story about the most interesting man in the world. The memes haven’t stopped to this day.

When Molson Canadian was looked down upon as little more than horse piss, they told us a story about Joe from Canada, who doesn’t know Suzie in Vancouver, but is sure she’s really nice, and along the way gave Canadians a renewed sense of collective identity.

When Mini wanted the world to take notice of their diminutive car, they strapped it onto the roof of an oversized SUV and drove it around major cities.

Great stories are hard to find.

It’s not easy. Telling a great story generally requires finding some grain of truth hidden in the rubble; something no one’s thought about before, or at least hasn’t been widely done before. But if your brand stands for something, there’s usually a great story hidden within it, somewhere. You just need to find it.

All of the brands above took massive risks. Old Spice could have been a laughing stock, but instead we laughed with them. Dos Equis could have been viewed as pretentious, but instead we embraced the schtick. Molson could have been viewed as callously exploiting Canadian patriotism, but instead renewed a nation’s sense of identity. Mini could have been laughed out of the market for selling a car that was so small it could fit on the roof of a real car, but instead found a market of people who wanted to buck the trend for bigger.

When you’re on top, taking huge risks is stupid. Just like it’s stupid to go all-in when you’ve got the biggest stack at the table. But when the choice is between playing it safe and being irrelevant, or taking a big risk and maybe, just maybe, lighting the market on fire… hold my Molson and pass me a match.

Psst… I wrote a book.

For those of you who are new around here, in 2023 I wrote and published a book, Insurgent Marketing. (Why yes, it’s the same name as this very newsletter.) In it, I share all my secrets from a career spent making every mistake imaginable, and learning from them. Save yourself the hassle and just read the book instead. You’ll thank me later.

You can buy it on Amazon or get your free PDF copy here.