HeyJaredThe Grit Files
The Grit Files is a podcast about entrepreneurs who dig deep with heart and grit to transform their passions into businesses. It's not always easy.
- Indexed episodes, last 90 days
- 22
- Latest publication
- Sep 7, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 8, 2026
Latest episodes
Why AI Won't Fix a Broken Business with Tullio Siragusa (opens the original)
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S6:E78 AI doesn't arrive inside a business as a neutral cure for everything that isn't working. It encounters the decision structures, silos, leadership behaviors, customer experience and culture that are already there and then it can make them move considerably faster. That's the tension at the center of this episode of Small Business Stories with Tullio Siragusa, founder of Inventrica Advisory. Tullio works at the intersection of artificial intelligence, leadership and organizational transform
How to Get Startup Funding with Vijay Rajendran (opens the original)
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S6:E77 A funding round can transform a company. It can also change who controls it, how it's expected to grow and even whether the founder remains CEO. So perhaps the first fundraising question shouldn't be How do I get the money? It should be: Do I actually want what comes with it? Queue up this episode of Small Business Stories with Vijay Rajendran , founder of Startup System and author of The Funding Framework , for a grounded look inside startup fundraising in 2026. Vijay describes a market
Small Business Cybersecurity: What You Don't See Can Hurt You with Last Pass CEO Karim Toubba (opens the original)
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S6:E76 Security is ultimately a promise of trust. So what happens when that trust gets broken? Karim Toubba has had to answer that question in circumstances few CEOs would choose. He joined LastPass as their CEO only months before the company experienced a significant and highly publicized 2022 security breach. In this candid conversation, Karim acknowledges that LastPass initially communicated too slowly and explains the systemic changes, transparency, investment and cultural work required afte
The Founder Trap: Why Your Business Isn't Growing Even When You're Working Harder with Charles Gaudet (opens the original)
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S6:E75 What if getting more customers actually made your business worse? That's the paradox Charles Gaudet sees repeatedly. A founder builds a business through hard work, referrals and personal relationships. Success arrives. More customers come in. Employees are hired. Yet instead of gaining freedom, the founder becomes the hub through which nearly everything still has to pass. Queue up this episode of Small Business Stories as Charles Gaudet, CEO of Predictable Profits, explains what he calls
How to Plan Your Business Exit When Your Kids Don't Want to Take Over with John Abrams (opens the original)
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S6:E74 What happens to your business when you aren't there anymore? For millions of founders, where more than half of all small businesses in the USA today are owned and operated by people over 50, that question is moving from theoretical to urgent. John Abrams says many owners assume they'll eventually pass the company to their children, sell it to an outside buyer or perhaps accept an offer from private equity. But there's another possibility: The people who helped build the business can own i
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