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Coffee with Jon - Think Big. Get Unstuck. Grow Your Business

Sep 30, 2026

Cara Lash left a coveted consulting job at PWC.
No safety net. No guarantee.

Just a belief that she was meant to build something.

Here are three highlights from our Coffee with Jon conversation:

1. Do it scared.
Don't wait until you're ready. You won't be.

2. Passion isn't enough. Be good at it too.
When passion and...


Sep 24, 2026

Finding a therapist shouldn't feel like a second job.

But for millions of Americans, it does.

Sandeep Acharya saw the broken system and built Octave Health to fix it.

Here are three takeaway's from our Coffee with Jon conversation:

1. Solve the friction first.
Therapists couldn't take insurance easily. Patients...


Sep 22, 2026

What if one of the most important skills we can teach isn't academics—but curiosity, kindness, and how to get back to center?

I sat down with Hamsa Yaqo and Paul Spiegelman, co-founders of Kintsugi Village, a unique early childhood learning community in Detroit focused on curiosity, creativity, life skills,...


Sep 22, 2026

3 Takeaways from my conversation with Chris McShanag, CEO of Virtual Teammate:

1. Every org chart needs a VA today.
Stop paying $100/hour talent to do $10/hour work. Free them up to do higher value work.

2. Clarity drives results — not geography.
A VA in the Philippines or Latin America performs when...


Sep 15, 2026

3 Takeaways from my conversation with Garrett Gunderson, Wealth Liberation Expert:

1. Heal your relationship with money first.
Scarcity mindset is inherited. Abundance is a choice. You can't build wealth while fighting the tool that creates it.

2. You are your greatest asset.
Stop shrinking. Invest in yourself, your...