[Editor’s Note: Below is the full text of our 233th Weekly Transmission, originally delivered direct to the inbox of more than 600 GEM members on November 16th, 2022.]

Image created by: Jasper Image description: burn the boats

In 1519, Hernán Cortés arrived on the beaches of present-day Veracruz in Eastern Mexico with 600 men set on plundering unimaginable treasure from the Aztec Empire. Before embarking on the inland journey, he said something remarkable.

Burn the boats.”

The takeaway was obvious: There is no turning back. His men would either secure the treasure and sail home in the Aztecs’ boats, or they would die trying.

Sun Tzu similarly advised burning “your boats and bridges” as you advance in war, and both Julius Caesar and Alexander the Great understood the psychology of this winning mentality.

Succeeding—as Cortés and his men did in conquering the Aztec Empire—requires commitment to win. It requires motivation and drive to move forward with zero uncertainty.

If the options are to either win or die, that reduces optionality. There is no going back when the going gets tough, as it inevitably will.

Yet, too often in our own lives we continually make excuses that keep us from achieving what we say we want.

So how can founders ensure this pivotal mindset is in place?

After exiting Yodle for $342 million, I could have raised VC capital or self-funded my next startup. Yet I chose neither of those paths. Instead, I convinced 30 of my friends and family to write $10,000 to $50,000 checks in order to fund Opcity’s initial $1 million. This was a far more complex, time consuming, and difficult undertaking—these checks were not pocket change for my social network at the time.

Why put myself through that? To build into my venture an extra incentive to succeed. To make turning back or quitting unfathomable.

After Yodle, I knew how painful, challenging, and time consuming the life of a startup founder is.  To go through that again, I needed to cut every lifeline so as to remove from the table the ability to retreat or surrender when times get tough.

In the early days of Opcity, I would question why I was putting myself through the 24-hour struggle of being an early-stage founder. After having built Yodle to close to 1,500 employees and managing a large exit, I found myself cold calling once again, starting at the bottom rung.

If it was just investor money, or even my own, I may have thrown in the towel. Yet seeing all of my friends and family—without much money to begin with—lose their sizable hard earned dollars was unquestionably the worst possible outcome. They had placed their trust in me. I felt an imperative for success, to win at all costs, to return their money and more.

When we exited Opcity in 2018, I received far more joy from calling my friends and family and telling them their initial ~$50,000 investments were now worth close to $1 million than I got from personally exiting. My big risk paid off in spades. Though cliche to say, the impact on the lives of those I valued most in the world, my friends and family, was priceless.

Everyone has their own way of burning the boats. In my case, it was taking friends’ money so I could not quit or surrender. For others, it could be publicly declaring your goal. A friend of mine broadcasted to her entire social network her intention to lose weight—putting it on social media every day and talking to her friends brought accountability.

All entrepreneurs are self driven, yet “burning the boats” can build into the process additional motivation. I was going to win or die — but under no circumstance was I going to lose my friends’ and family’s money. Conceding defeat was not an option.

It’s not the right approach for every founder, but for many, finding “boats” or “lifelines” to burn so as to remove the temptation to surrender makes it easier to push through tough days and low points. It makes success a foregone conclusion. At least it did for me.

We are in a perhaps unseen market and uncharted waters right now. Capital is harder to secure, and real estate transactions have slowed to a trickle. What are the boats you need to burn to ensure success through it all?



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