Ep 289 – From Tragedy to 65 Units: How Cara and Mark Truckey Built a Life and Business on Their Own Terms
In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare. Most couples don't survive a loss like that. Instead, it became the moment that changed everything. In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and [...]
Ep 288 – Your STR Could Be Banned Tomorrow and here’s What You’re Not Doing About It | ft. Julie Marks
Most STR operators don't think about regulation until it's already too late. Julie pulls back the curtain on what’s really happening in short-term rental regulation and why hosts can’t afford to stay invisible. From local politics to nationwide advocacy, this episode is a wake-up call for operators who think regulation is someone else’s problem. • How Julie went from accidental host to industry advocate • Why anti-STR arguments often hide [...]
Ep 287- 5 Years. 180 Properties. 36 People. Aidan Groll on Building a Real STR Management Company
Most STR companies obsess over guest reviews. Blue Gems obsesses over owner profitability. And they grew to 180 properties under management doing it. In this episode, recorded live at the Freedom Factory in Beverly, MA, E sits down with Aidan Groll — co-founder of Blue Gems Management, one of Florida's fastest-growing STR companies. Aidan and his partner JB manage 180+ properties across Orlando and Clearwater Beach with a 36-person team [...]
Ep 286 – Why You Keep Self-Sabotaging Even When You Know Exactly What to Do
Q1 is almost over. E has something to say about it. In this solo episode, co-host Emanuele shares everything he's been working on in 2026 — and gets raw about why most people are still stuck. The problem isn't the tools. It's not the market. It's not the strategy. It's your beliefs. E breaks down Tony Robbins' 3 S's — why State and Story have to come before Systems. He [...]
Ep – 285 The ‘Help First’ Sales Mindset That Grew Them From 12 to 120 Properties with Sean Bakhtiari
What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals? Sean Bakhtiari grew up in New Hampshire, studied finance at Providence College, and spent 9 years in Boston's financial district working in sales, marketing, and client experience. He loved the work — but always knew he wanted to build something of his own. So he bought his first [...]
Ep – 284 Why Most STR Operators Fail at Hiring (Leadership Masterclass) with Alex Hall
Scaling a short-term rental company isn’t just about getting more properties. It’s about building the team that can support the growth. In this episode, Chris and E sit down with Alex Hall — talent advisor and leadership strategist — to break down the real challenges STR operators face when building teams. From job clarity and org structure to burnout, hiring, and leadership development, Alex shares the frameworks that help operators [...]
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