• How Fear Fueled a $100B Brand
    Jun 24 2025

    Most people run from failure—but what if it’s the very thing that drives you? In this episode, David and Chris unpack how fear fueled Howard Schultz’s relentless pitch for Starbucks, despite hearing "no" 217 times. Why do some founders push through while others freeze—and what’s really holding you back?


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    27 mins
  • The Worst Trailer of All Time
    Jun 23 2025

    Bros, Business, Banter. That's us.

    It's the trailer for the Startup Different pod.

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    2 mins
  • Is AI Ruining US? (And Maybe Your Kids?)
    Jun 17 2025

    If every meaningful win in your startup came from struggle...what happens when AI takes that away? Chris hits the wall building with AI tools, David wonders if his kids will ever build resilience, and together they unpack whether AI is eroding the effort that makes real growth possible. This one's for the founders who've earned their scars—and wonder if the next gen ever will.


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    29 mins
  • Will ChatGPT Crush Your AI Startup?
    Jun 10 2025

    Think your AI startup is safe? Think again. In this episode, we unpack how foundational models like ChatGPT are steamrolling niche platforms by absorbing their features overnight—and what you can do to survive. From building unique integrations to niche-first moats, David and Chris share five hard-won lessons for AI founders trying to stay in the game before OpenAI levels the field.


    The 5 lessons?

    1. Don't Compete on Core AI Capabilities
    2. Build Moats with Unique Integrations
    3. Focus on UX and Workflow, Not Accuracy
    4. Target a Niche and Go Deep
    5. Build to Exit, Not to Last Forever

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    29 mins
  • Who Can CONFRONT Elon?
    Jun 3 2025

    We're trying a new format with the pod. Let us know what you think. Today it's "who can confront Elon"? In this unfiltered and wickedly funny episode, David and Chris explore how one man’s ego—Elon Musk—has torched Tesla’s brand, stock, and reputation, all while loyal fans quietly peel logos off their cars. From a 71% profit nosedive to Cybertruck chaos, it’s a masterclass in founder risk, brand backlash, and why empathy still matters. #ElonMusk #TeslaFail #StartupPodcast #Cybertruck #TeslaStock #BrandReputation #BootstrappedFounders #StartupDifferent


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    29 mins
  • Is Ego Killing Your Startup?
    May 27 2025

    What if your biggest growth block isn’t funding or strategy—but you? In this episode, we explore how ego quietly sabotages leadership and limits your team’s potential. Learn how emotional intelligence, real feedback, and a shift in mindset helped Carrie Fabris build a business helping execs lead better—without the burnout.


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    32 mins
  • Skip the Payroll - Keep the Progress
    May 20 2025

    What happens after you exit your startup and don't want a boss again? Taylor Crane shares how that moment led to a new way of working—and a new way of thinking about early hires. We dig into product lessons, co-founder dynamics, and what fractional roles look like behind the scenes. Plus, we cover when bringing on part-time leadership is actually smarter than hiring full-time.


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    31 mins
  • Can You Grow Too Fast?
    May 13 2025

    She quit her job, had no funding, and started fermenting cider in a garage with her husband. What could go wrong?! Hint: it's not what you think. Within a year, Alicia Hardman and her hubby were running a 10,000 sq. ft. winery with lines out the door—thanks in part to a viral swing table. But what happens when your startup grows faster than you can manage? Was all that growth a good thing?

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    26 mins