In this episode of Thoughts on Selling, I sit down with someone I truly consider a “brother from another mother” — Lester Sidney.

If there’s a theme for this conversation, it’s this:

👉 Sales is human work. And humans run on purpose, energy, trust, and honesty.

Lester discusses his 17-year tech sales career, a couple ofunexpected detours, and the journey that ultimately led him to rediscover his why: helping people see the potential insidethemselves that they can’t yet see.

What unfolds from there is one of the most honest, raw, and deeply human sales conversations we've recorded.

We talk about:

·      Finding purpose when life knocks you flat, including Lester’s battle with depression after leaving a company he helped build.

·   The Ikigai framework and how it helped him identify a deeper purpose rooted in mentoring and coaching.

·      Energy as a magnet — how the energy we project determines the people and opportunities we attract.

·       Why giving beats taking, and how “pay it forward” moments shape who we become.

·       The sacred role of trust in sales, and why walking away from a deal can be the single biggest credibility builder you’ll ever have.

·       Extreme Ownership — and why real leaders take responsibility for everything their team does. (Yes, this comes with stories.)

·       Why vulnerability isn’t weakness — it’s a sales superpower. Lester is candid about how being open unlocks deeper relationships with customers.

·       The compound effect, and why small improvements add up to big transformation — in fitness, in selling, and in life.

·       Raising kids with mindset, from eliminating the word can’tto teaching his son that mistakes are how we grow.

·       What Lester looks for when hiring sellers — and why coachable is the non-negotiable #1 trait.

This is an episode about selling, yes — but more importantly, it’sabout being human. It’s about showing up with authenticity, owning your story, doing the hard things, and leading with heart.

It’s one of my favorite episodes we’ve done. Give it a listen —and please tell me what resonates most with you!