The Long Game Wins: Business Lessons from a Soft Serve Stand with Gemma Geldmacher
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Release Date: 08/10/2026
Jon Ostenson on AI Proof Your Franchise The Smarter Path to Business Ownership
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Most people think franchising is the easy path to business ownership. It's not. But it might be a smart path. I sat down with John Ostenson — top 1% franchise broker and CEO of FranBridge Consulting — and here's what stood out: 3 Takeaways: 1. AI-proof your investment. The smart money is flowing into trades and home services — businesses AI can use but never replace. 2. Activity breeds activity. Stop waiting for the perfect time. It doesn't exist. Start moving toward option A or B — option C shows up when you're in motion. 3. Your first hire in that key seat can make or...
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The Long Game Wins: Business Lessons from a Soft Serve Stand with Gemma Geldmacher
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Playing the Long Game: Lessons from a HUD Specialist and a Soft Serve Stand I sat down with Gemma Geldmacher, Managing Director of Mortgage Banking at Berkadia, to talk about her successful career and her blog — Playing the Long Game: Hard Lessons Through Soft Serve. It's the story of watching her parents immigrate from Australia in 1984 with three kids, buy a local community ice cream shop, and the lessons that came with it. The business lessons inside that shop can help all of us in business and life. Here are a handful of the lessons Gemma and I talked about: * Efficiency is an act of...
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Can AI Predict Disease Before Doctors? Adam Wolfe of Chroneme
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Adam Wolfe tragically lost his son eight years ago. Adam channeled his pain it into building something that could prevent the same thing from happening to others. Co-Founder of Chroneme — The first clinical AI built to show its work. Chroneme reads how your health changes over time. Every signal, from every provider, across years. And when something is developing, it knows. Before the doctor. Before the diagnosis. Before the emergency. Connect with Jon Dwoskin: Twitter: Facebook: Instagram: Website: LinkedIn: Email: Get Jon's Book: Connect...
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Think Like Elon: Eric Jorgenson on First Principles, Focus & Innovation
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
I sat down with Eric Jorgensen, CEO of Scribe Media and author of The Book of Elon. Here are 3 things that stuck with me: What you think is your best is a fraction of what you're capable of. Elon isn't just working harder, he's cut through the noise to focus on what matters. First principles thinking breaks you free from conventional limits. Stop reasoning by analogy, asking what everyone else does. Start asking what's actually possible. The gap between those two questions is where innovation lives. Your uniqueness is your advantage. The world rewards people who are singular, -- Eric...
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Eric Miller on Why Your Household Is the Most Important Business You Own
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Most business owners run their company like a business — and their household like an afterthought. I sat down with Eric Miller, co-founder of Econologics Financial Advisors. Here are 3 things that stuck with me: 1. Your household is the parent company. Everything else is a subsidiary. 2. You're probably operating on the wrong number. 3. Do it now. Planning doesn't have to be a big event. -- Eric Miller is a seasoned financial planning professional with over 20 years of experience dedicated to empowering private practice owners and associates. As Co-Owner and Chief Financial Advisor of...
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Eric Miller on Why Your Household Is the Most Important Business You Own
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Most business owners run their company like a business — and their household like an afterthought. I sat down with Eric Miller, co-founder of Econologics Financial Advisors. Here are 3 things that stuck with me: 1. Your household is the parent company. Everything else is a subsidiary. 2. You're probably operating on the wrong number. 3. Do it now. Planning doesn't have to be a big event. -- Eric Miller is a seasoned financial planning professional with over 20 years of experience dedicated to empowering private practice owners and associates. As Co-Owner and Chief Financial Advisor of...
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Why Focus Beats Hustle in Building a Brand with Ben Feys and Kevin Niehoff
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
I sat down with Ben Feys and Kevin Niehoff, co-founders of Pretty Boy — a men's skincare brand built from scratch. Here are 3 things that stuck with me: 1. Master one channel before you touch anything else. 2. Call your customers. 3. Stability beats the dopamine hit of a big spike. The fundamentals haven't changed. Knowing your customer, delivering the right message, and staying close to the business — that's the playbook. --- PrettyBoy started because we were sick of guessing - years of acne, eczema, prescriptions, and overpriced nonsense taught us the skincare industry wasn’t...
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What Are You Good At: Jeff and Jason Hamama on Growth, AI & Success
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Great conversation with Jason Hamama of Encore Development 3 Takeaways • Follow your obsession. Curiosity often reveals what you’re great at. • Use AI to move faster. It’s the tool that will accelerate great operators. • Hard work still wins. Technology changes. Effort never goes out of style. Connect with Jon Dwoskin: Twitter: Facebook: Instagram: Website: LinkedIn: Email: Get Jon's Book: Connect with Jeff Gunsberg: Website: Connect with Jason Hamama:LinkedIn: https://www.linkedin.com/in/jason-hamama-92767172...
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Katie Fortunato on AI-Native Growth & Monetizable Content
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Katie Fortunato, President of Jobstream: Co-founder of a new ai-native technology disrupting the affiliate marketing industry with a new category of monetizable content. Connect with Jon Dwoskin: Twitter: Facebook: Instagram: Website: LinkedIn: Email: Get Jon's Book: Connect with Katie Fortunato: Website: Instagram: @jobstream_ LinkedIn: *E - explicit language may be used in this podcast.
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Jason Wong on Why Packaging Sells Before You Do
Coffee with Jon - Think Big. Get Unstuck. Grow Your Business
Three takeaways from my conversation with Jason Wong, CEO of Paking Duck: 1. Your packaging is already making decisions for your customers before they touch your product. 2. The best salespeople don't close. They let customers close themselves. 3. AI should be a co-pilot, not a replacement. What's one area in your business where AI could take something off your plate? Connect with Jon Dwoskin: Twitter: Facebook: Instagram: Website: LinkedIn: Email: Get Jon's Book: Connect with Jason Wong: Website: *E - explicit language...
info_outlinePlaying the Long Game: Lessons from a HUD Specialist and a Soft Serve Stand
I sat down with Gemma Geldmacher, Managing Director of Mortgage Banking at Berkadia, to talk about her successful career and her blog — Playing the Long Game: Hard Lessons Through Soft Serve. It's the story of watching her parents immigrate from Australia in 1984 with three kids, buy a local community ice cream shop, and the lessons that came with it. The business lessons inside that shop can help all of us in business and life.
Here are a handful of the lessons Gemma and I talked about:
* Efficiency is an act of love.
* The universe may have plans you didn't expect.
* Consistency isn't a tactic. It's a legacy.
* The partner you choose changes everything.
* Showing up isn't optional.
* The rigid path is a trap.
* Someone saw it before you did.
* Legacy is built in the ordinary moments.
* Reflection is a competitive advantage.
* AI won't replace you. Accepting the output will.
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Gemma is a managing director at Berkadia where she has been a loan originator for 10 years. Prior to that she had over eight years experience underwriting and screening commercial real estate loans.
Connect with Jon Dwoskin:
Twitter: @jdwoskin
Facebook: https://www.facebook.com/jonathan.dwoskin
Instagram: https://www.instagram.com/thejondwoskinexperience/
Website: https://jondwoskin.com/
LinkedIn: https://www.linkedin.com/in/jondwoskin/
Email: jon@jondwoskin.com
Get Jon's Book: The Think Big Movement: Grow your business big. Very Big!
Connect with Gemma Geldmacher:
Website: www.berkadia.com
LinkedIn: https://www.linkedin.com/in/gemmageldmacher
Article: https://www.linkedin.com/pulse/playing-long-game-hard-lessons-through-soft-serve-gemma-geldmacher-q05he/?
Bio: https://www.berkadia.com/people-and-locations/people/gemma-geldmacher
*E - explicit language may be used in this podcast.