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

Jon Dwoskin
  • 5.0 (113)
  • Management
  • Updated Daily

Coffee with Jon -Formerly THINK Business Deep, soulful conversations with executives, managers, and sales professionals who are making a real difference — in their companies, their communities, and within themselves. Inspired by the legendary Larry King, Coffee with Jon brings you 1:1 interviews built around curiosity, authenticity, and the art of truly listening. Like King, host Jon Dwoskin puts the guest and their journey at the center of every conversation — asking the questions that uncover not just what people do, but why they do it, and what drives them to show up and lead the way they do. Every episode is a chance to see the bigger picture, shift your perspective, and find the spark that moves you to your own next level. Pull up a chair. Pour yourself a cup of coffee and let's - Get Unstuck & THINK BIG!

  1. 10h ago

    Jon Ostenson on AI Proof Your Franchise The Smarter Path to Business Ownership

    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 break everything. Good isn't good enough. One A-player running your franchise while you keep your day job changes the entire trajectory. --- Jon Ostenson is a top 1% national franchise broker, investor, author, and international speaker specializing in the area he has coined as 'Non-Food Franchising'. Having served as the President of an Inc. 500 franchise system and now as a multi-brand franchisee, himself, Jon is uniquely positioned to educate others on franchising and franchise selection. Jon serves as CEO of FranBridge Consulting and has helped thousands of entrepreneurs and investors explore business ownership and investment opportunities. Jon is the author of the book "Non-Food Franchising'' and is a frequent contributor and thought leader for publications on the topic of franchising and franchise investments. Prior to FranBridge, Jon was the President of ShelfGenie, a national franchise system with 200+ locations. 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 Jon Ostenson: Website: https://franbridgeconsulting.com LinkedIn: https://www.linkedin.com/in/jonostenson  *E - explicit language may be used in this podcast.

  2. 1d ago

    The Long Game Wins: Business Lessons from a Soft Serve Stand with Gemma Geldmacher

    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 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. --- 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.

  3. Aug 4

    Can AI Predict Disease Before Doctors? Adam Wolfe of Chroneme

    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: @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 Adam Wolfe: Website: https://chroneme.com *E - explicit language may be used in this podcast

  4. Jul 30

    Think Like Elon: Eric Jorgenson on First Principles, Focus & Innovation

    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 Jorgenson is the CEO of Scribe Media. He published two books with Scribe prior to becoming CEO. The Almanack of Naval Ravikant has sold over 1,000,000 copies, been translated into 30+ languages, and seen over 4,000,000 digital copies given away for free. He runs an early stage technology investment firm called Rolling Fun, and was previously in Growth & Product roles at Zaarly. Watch our previous interview 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 Eric Jorgensen: Eric Jorgensen Books: https://www.ejorgenson.com/books-1  Website: https://scribemedia.com  X: https://twitter.com/scribemediaco  LinkedIn: https://www.linkedin.com/company/scribe-media  Instagram: https://www.instagram.com/scribemediaco  Facebook: https://facebook.com/scribemediaco  YouTube: https://www.youtube.com/channel/UCen_O0dVTbVAK-XF9IjPitQ      *E - explicit language may be used in this podcast.

  5. Jul 28

    Eric Miller on Why Your Household Is the Most Important Business You Own

    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 Econologics Financial Advisors, LLC, a Registered Investment Advisor, Eric specializes in strategic financial planning, including investments, retirement, asset protection, tax strategies, debt elimination, and business transition planning. A Registered Financial Consultant® (RFC) and graduate of Capital University, Eric is also a prolific author and speaker and has published countless articles, videos, and podcasts and is the bestselling author of How to Become a Financial Beast. He has presented at hundreds of events nationwide, and weekly hosts the Financial Beast Podcast. 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 Eric Miller: Website: www.econologicsfinancialadvisors.com YouTube: https://www.youtube.com/c/FinancialBeast  LinkedIn: www.linkedin.com/in/ericisyourbfff   Facebook: www.facebook.com/econologicsfinancial       *E - explicit language may be used in this podcast.

  6. Jul 28

    Eric Miller on Why Your Household Is the Most Important Business You Own

    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 Econologics Financial Advisors, LLC, a Registered Investment Advisor, Eric specializes in strategic financial planning, including investments, retirement, asset protection, tax strategies, debt elimination, and business transition planning. A Registered Financial Consultant® (RFC) and graduate of Capital University, Eric is also a prolific author and speaker and has published countless articles, videos, and podcasts and is the bestselling author of How to Become a Financial Beast. He has presented at hundreds of events nationwide, and weekly hosts the Financial Beast Podcast. 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 Eric Miller: Website: www.econologicsfinancialadvisors.com YouTube: https://www.youtube.com/c/FinancialBeast  LinkedIn: www.linkedin.com/in/ericisyourbfff   Facebook: www.facebook.com/econologicsfinancial       *E - explicit language may be used in this podcast.

  7. Jul 23

    Why Focus Beats Hustle in Building a Brand with Ben Feys and Kevin Niehoff

    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 built for guys like us. We wanted products that were simple, effective, and actually felt good to use, without turning skincare into a second job. We partnered with top chemists and dermatologists to build a no-nonsense system focused on real results, not hype. I handle the business side - operations, product strategy, and ensuring everything works as intended. My co-founder leads the creative and brand vision, ensuring PrettyBoy stays cool, on-brand, and unmistakable. 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 Ben Feys and Kevin Niehoff: Website: www.yoprettyboy.com X: https://x.com/fenbeys Instagram: https://www.instagram.com/benfeys/ LinkedIn: https://www.linkedin.com/in/benjamin-feys-23112950    *E - explicit language may be used in this podcast.

  8. Jul 21

    What Are You Good At: Jeff and Jason Hamama on Growth, AI & Success

    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. https://www.linkedin.com/in/jason-hamama-92767172   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 Jeff Gunsberg: Website: https://title-connect.com Connect with Jason Hamama: LinkedIn: https://www.linkedin.com/in/jason-hamama-92767172   *E - explicit language may be used in this podcast.

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About

Coffee with Jon -Formerly THINK Business Deep, soulful conversations with executives, managers, and sales professionals who are making a real difference — in their companies, their communities, and within themselves. Inspired by the legendary Larry King, Coffee with Jon brings you 1:1 interviews built around curiosity, authenticity, and the art of truly listening. Like King, host Jon Dwoskin puts the guest and their journey at the center of every conversation — asking the questions that uncover not just what people do, but why they do it, and what drives them to show up and lead the way they do. Every episode is a chance to see the bigger picture, shift your perspective, and find the spark that moves you to your own next level. Pull up a chair. Pour yourself a cup of coffee and let's - Get Unstuck & THINK BIG!

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