Molly’s Game: Lessons On Ethics For Entrepreneurs From Underground Poker

Posted: Mar 20, 2018 10:00 AM
Molly’s Game: Lessons On Ethics For Entrepreneurs From Underground Poker

I was left with three impressions after finishing “Molly’s Game,” Molly Bloom’s memoire of her time in the poker underworld. First, the Oscar nominated movie was surprisingly consistent with her story as told in the book. Second, Molly Bloom emerged from her sojourn battered but remarkably resilient. Third, her book should be required reading in introduction to entrepreneurship classes.

Molly Bloom was the “poker princess” of Hollywood, running a multimillion dollar underground game while rubbing elbows the entertainment industry’s elite and powerful. When she was squeezed out of Los Angeles, she started up another game in New York City. This time, her game attracted uber wealthy hedge-fund managers, financiers, foreign investors, and… the mob.

She accomplished all this by the time she reached her mid thirties. 

In the end, she crashed and burned, although not for lack of entrepreneurial wit or drive.

Bloom built a relatively unknown game into one of the biggest, a high-stakes poker game that attracted the wealthiest amateur players. She leveraged one game into several, eventually overseeing dozens of employees. She did it by diving deep into understanding her product, thinking critically about the business of poker, and studying her customer’s wants. She never played with or against her clients, and she focused on creating an experience that her multimillionaire players were willing to monetize. She made millions.

She also made mistakes. Big time. She became the bank for the players, a double-edged sword that allowed her to cater to the personal desires of her customers but exposed her to unsustainable financial risk. She built her game on the egos, misogyny, and bullying that accompanied men with large bank accounts. She also underestimated the degree to which the emotional insecurity of some clients would feed a drive to emasculate her. She discounted the viciousness of the mob in New York, and naively failed to consider the take-no-prisoners philosophy that federal prosecutors use to bully potential witnesses into testifying against their true targets.

How much revenue Bloom’s enterprise generated is hard to tell. While she kept her business legal, she operated in a grey area of the law. She was paid in tips. One year, she reported income as an “event planner” of $4 million to the IRS. She was living the high life in LA, the Big Apple, and the Hamptons.

She also found her world spinning out of control, in part because she was unable to manage the overwhelming demands and contradictions implicit in the enterprise she created. She descended into drug addiction in an unsustainable attempt to manage her high-powered, 24-7 business. She started to skirt the law, effectively taking a share of the pot in an attempt to manage her financial exposure, widening the doors federal prosecutors needed to arrest her.

Her business imploded, a result that she sees in hindsight but more seasoned entrepreneurs may well have seen coming early on.

Despite all this, Bloom has no regrets. “I learned to believe in myself,” she writes in her telling of her “grand adventure.” “I was brave, and I went big.”

She is also explicit and honest about her business’s dark side. “I was also reckless and selfish,” she observes. “I got lost along the way…. But I was forced to face myself, to lose everything, to fall on my face in front of the world, and the lessons I learned on the way up were as valuable as the ones on the way down.”

This introspection is why her story is so compelling, and so necessary for aspiring entrepreneurs to hear. 

Failure is part and parcel of being an entrepreneur. Solving problems, managing risk, and pivoting are essential to growing and leveraging a business. The potential for success motivates the entrepreneur’s drive. But it’s also coupled with risk, often significant risks. This duality is hard wired into the “growth mindset” that drives value creation and monetizing these efforts through the marketplace.

Just as important, however, is the need for entrepreneurs to stay grounded. Bloom learned this lesson the hard way. She “got lost” when she “abandoned the things that mattered and traded them for wealth and status. I lusted for power and I hurt people.” She astutely recognizes her willingness to abandon the “things that mattered” were an important part of the reason her enterprise faltered. She is now a convicted felon.

Staying grounded means more than being realistic about your enterprise, its potential, and being smart about how resources are used to achieve your objectives. Indeed, Bloom excelled in almost all of these metrics of business.

Her entrepreneurial and personal growth, however, came from grappling with another, too often ignored aspect of business and entrepreneurship: Ethics. Knowing right from wrong, accepting the consequences of personal and executive decisions, and owning up to the harm inflicted on others through those decisions, even if the outcomes were unintentional, are all part of sustainable entrepreneurship.

Honoring those closest to you in personal life and business is not just a noble endeavor; it’s a recognition that if we fail…when we fail…we will be rebuilding our lives and vocations with the people that continue to believe in us, support us without qualifications, and help us get back on our feet when we are at our lowest. This is the human dimension of entrepreneurship that can’t be captured in accounting ledgers, strategic planning, or market valuations. They are, however, essential to the resilience of an entrepreneur and the sustainability of an entrepreneurial economy.  These are relationships that exist only if they are recognized, honored, and embraced.

Drawing on my 30-plus year journey in nonprofit management, social entrepreneurship, and start-ups, I tell my students that they can’t fail before they are thirty in the United States. We have a culture that tolerates failure. Indeed, our freedom-oriented, market-based culture implicitly recognizing the value of failure in building more resilient, more reflective, and more experienced human beings capable of achieving great heights.

This tolerance for failure, however, comes with three critically important caveats. First, our efforts must be sincere and authentic. Two, we must pursue our enterprises with integrity, honesty, and transparency. Three, and perhaps most importantly, we must honor and respect the relationships we develop along the way. These human relationships are the ones that take us over the finish line in the long run.

“Molly’s Game” may not have taken home the award for Best Adapted Screenplay at the 2018 Academy Awards, but Molly Bloom has provided a real-world testimony to the truth behind the fundamental ethics of thriving in an entrepreneurial culture and society. For this, her story is worth hearing, and understanding, particularly for those beginning their entrepreneurial journey.