The Human Side of Sales: Ikigai, Trust & Extreme Ownership w/ Lester Sidney
Episode SummarySales is human work. And humans run on purpose, energy, and trust. Lee Levitt sits down with Lester Sidney, a 17-year tech sales veteran and "brother from another mother," for a raw and authentic conversation.
Lester opens up about his battle with depression after leaving a company he helped build and his journey to rediscovering his "Why" through the Ikigai Framework. We discuss why Vulnerability is a sales superpower, why walking away from a bad deal is the ultimate credibility builder, and how to apply Jocko Willink’s concept of Extreme Ownership to sales leadership.
Memorable Quotes:
"Sales is human work. And humans run on purpose, energy, trust, and honesty."
"Walking away from a deal can be the single biggest credibility builder you’ll ever have."
"I help people see the potential inside themselves that they can’t yet see." — Lester Sidney on his core purpose.
3 Actionable Takeaways for Leaders:
Hire for Coachability: When Lester hires, he looks for one non-negotiable trait: Coachability. You can teach product knowledge and territory management, but you cannot teach an ego to listen.
The "Walk Away" Power Move: Trust isn't built when you sell; it's built when you don't sell because the fit isn't right. Teach your team that "No" is a complete sentence that earns you the right to ask for the next "Yes."
Apply the Ikigai Framework: If your top reps are burning out, it’s likely a misalignment of purpose. Use the Ikigai model (What you love, What you're good at, What the world needs, What you can be paid for) to help them reconnect their daily grind to a larger mission.
Key Topics & Timestamps:
(00:00) – Introduction: A "Brother from Another Mother."
(05:30) – The Crash: Lester’s candid story of depression and finding purpose after a career exit.
(12:15) – The Ikigai Framework: How to find the intersection of passion, mission, vocation, and profession.
(19:40) – Energy as a Magnet: Why the energy you project determines the opportunities you attract.
(26:00) – Trust & Credibility: Why walking away from a deal is the ultimate sign of integrity.
(33:20) – Extreme Ownership: Taking full responsibility for your team's failures (and giving away credit for their wins).
(40:15) – Vulnerability in Sales: Why "armored" leadership fails and authentic leadership scales.
(48:00) – Hiring the "Coachable": The #1 trait Lester looks for in top performers.
About Our Guest:Lester Sidney is a dynamic sales leader with a 17-year career in the technology sector. Known for his "human-first" approach to revenue, Lester specializes in mentoring and coaching sales professionals to unlock their hidden potential. He is a passionate advocate for Mental Health in Sales, Servant Leadership, and the power of a growth mindset.
About the Host:
Lee Levitt is a seasoned sales performance consultant, sales coach and the Principal of The Acelera Group.
With deep experience in Sales, Sales Leadership, Sales Enablement, Revenue Operations, and Sales Performance Management, Lee helps enterprise organizations build disciplined, replicable sales operating systems.
He is the voice behind the Thoughts on Selling™ brand, covering the intersection of deal mechanics and the "Inner Game" of selling.
Related Episodes:
Ep 43: The Inner Game of Selling w/ Jeff Lipsius: Exploring the mindset required to win.
Ep 76: Who Are You? w/ Gerhard Gschwandtner: Why self-awareness is the precursor to sales success.
Resources & Links:
Framework Mentioned: Explore the Ikigai Concept for purpose-finding.
Book Mentioned: Extreme Ownership by Jocko Willink.
Connect with Lester: Find Lester Sidney on LinkedIn.
Subscribe: Get the Thoughts on Selling newsletter at thoughtsonselling.com.
Keywords:Sales Leadership, Mental Health in Sales, Ikigai, Extreme Ownership, Trust Based Selling, Servant Leadership, Sales Mindset, Vulnerability, Coachability, Hiring Sales, Personal Development, Emotional Intelligence
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Thoughts on Selling™ is a trademark of The Acelera Group, LLC. All rights reserved. Federal trademark registration pending.
Sales & Go-To-Market Advisor
Lester Sydney is a Sales and Go-To-Market Advisor with over a decade of experience helping founders and sales teams grow revenue without pressure or performative tactics. His approach centers on trust-based discovery, buyer-led decision making, and building sales motions that actually last.
Lester has led enterprise sales teams, closed complex B2B deals, and works closely with founders to align sales execution with real business outcomes. He believes the best sales conversations create clarity, not urgency and relationships, not transactions.
