A Ceo in Crisis with Simon Leslie: An EOFire Classic from 2022

What if starting over became your strongest habit?

Simon Leslie makes a persuasive case for being comfortable with the messy, early days. He calls it "white belt thinking" — the intentional choice to show up as a beginner each day, curious and unfixed. That simple mental shift becomes a practical survival tool when fortunes reverse and familiar playbooks fail.

White-belt thinking: a tactical beginner's mind

White-belt thinking is not humility for humility's sake. It's a tactical posture: treat every problem like a twelve-hour mission and refuse to be paralyzed by long-term fear. Simon describes waking up during the pandemic and asking himself, "How do I get through the next 12 hours?" That granular focus turned anxiety into a sequence of manageable decisions.

What really caught my attention was how he pairs that mindset with disciplined thinking time. He tells a story about a colleague who left the office, came back with a clear answer, and saved a day of wasted stress. It reminded me that quiet thinking is a productivity hack disguised as patience.

Equanimity as leadership muscle

Equanimity, for Simon, was not a buzzword but a lifeline. He sat on a bench staring at the sea and wrestled with whether his company would survive an unprecedented shutdown of global travel. Rather than chase quick fixes, he invested in people — calling friends, arranging unpaid talks, and keeping morale afloat.

That choice to preserve culture instead of cornering every dollar felt radical. It's a model for leaders who must juggle immediate survival with long-term team health. The emotional undercurrent is powerful: calm under pressure gives teams the oxygen to keep doing their best work.

From crisis to courage

Simon refuses to romanticize resilience. He admits to moments of utter doubt and imposter syndrome, even at the height of success. Yet those doubts became a throttle, not a handbrake; he upgraded his stakes and decided to play a bigger game.

His poker metaphor is deliciously clear. Whether you're sitting at a small table or the Bellagio’s high-stakes table, the rules are the same — but your results change with the bet size. For Simon, the pandemic peeled back the illusion of safety and pushed him toward bolder bets.

Sales mastery as an act of continuous learning

He calls himself a sales nerd and wears the badge with pride. Three hundred thousand hours of learning (yes, that number) have given him a humble certainty: mastery requires daily curiosity. He blends old-school techniques with behavioral science, NLP, and fresh ideas from junior team members.

That combination — reverence for classics plus openness to new inputs — is one of the clearest playbooks for anyone who sells, leads, or persuades. The most surprising part? Simon still sees himself as a white-belt in sales. That admission is oddly liberating.

Miracles, mentorship, and the moral economy of giving

One story gives the conversation an almost mythic quality. A timely payment from a German bank arrived as the company teetered, and Simon frames that moment as a miracle that kept the business alive. Whether you read it as luck, timing, or faith, it shifted his belief about endings: "If it's not okay, it's not the end."

He turned gratitude into action. He made the company a place for learning — inviting speakers to spend unpaid hours with employees, mentoring his son through real responsibility, and testing his playbook by letting others use it. That replication of method into other people's success felt like legacy design, not ego preservation.

Poetry as a leadership practice

Then there’s a strange, delightful detour: poetry. Simon began writing four-line poems as a way to process anxiety. The poems multiplied into a 400-page collection that he gifts to strangers, Uber drivers, and collaborators around the world. It’s an odd leadership instrument — softening edges, creating human connection, and reminding people that seriousness and tenderness can coexist.

Giving away those poems also reframes value. Rather than monetizing every output, he used creativity to rebuild trust and emotional capital. I found that move unexpectedly generous and strategically sharp.

Practical takeaways worth stealing

• Practice micro-horizons: break big fears into twelve-hour missions to reduce overwhelm and improve decision-making.
• Protect culture first: keep people inspired when revenue falls; momentum is as much emotional as financial.
• Stay a learner: mix classic sales techniques with behavioral science and fresh front-line ideas.
• Teach your playbook: test your systems by giving them to juniors; replication proves the formula.

Final thought

Simon Leslie's story is a reminder that leadership is as much about inner practice as outer tactics. Patience, curiosity, faith, and a willingness to be a beginner are not fluffy virtues — they're the scaffolding that lets people and businesses rebuild when the ground shifts. Imagine treating setbacks as invitations to return to white belt posture; what might that decision do to your next twelve hours?