Podcasts

Ep 286 – Why You Keep Self-Sabotaging Even When You Know Exactly What to Do

2026-03-23T07:02:40-04:00

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 walks through the 5 core wounds that quietly drive self-sabotage: rejection, abandonment, humiliation, betrayal, and injustice. And he explains why your beliefs work like a thermostat — no matter how big [...]

Ep 286 – Why You Keep Self-Sabotaging Even When You Know Exactly What to Do2026-03-23T07:02:40-04:00

Ep – 285 The ‘Help First’ Sales Mindset That Grew Them From 12 to 120 Properties with Sean Bakhtiari

2026-03-16T07:46:01-04:00

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 STR. Then a second. Then started building a management company. At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? [...]

Ep – 285 The ‘Help First’ Sales Mindset That Grew Them From 12 to 120 Properties with Sean Bakhtiari2026-03-16T07:46:01-04:00

Ep – 284 Why Most STR Operators Fail at Hiring (Leadership Masterclass) with Alex Hall

2026-03-09T06:28:45-04:00

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 scale from a handful of listings to a real company. If you're trying to grow beyond the stage where you do everything yourself, this episode is a masterclass in leadership and [...]

Ep – 284 Why Most STR Operators Fail at Hiring (Leadership Masterclass) with Alex Hall2026-03-09T06:28:45-04:00

Ep – 283 From Bankruptcy to a $100M Real Estate Vision with Jonathan St.Leger

2026-03-02T05:31:35-05:00

He built a “sexy” real estate portfolio in the early 2000s… Then 2008 hit. Reserves drained. Assets liquidated. Eventually — bankruptcy. Most investors never come back from that. In this episode, Jon St. Leger breaks down: • What the 2008 crash really felt like • Why he keeps his portfolio at 33% LTV • How to prepare for the next recession • What “Equity Manifestation” actually means • How he turned a 20-room motel into a 47-key boutique hotel • Why delayed gratification builds real wealth • The blue-collar advantage most people ignore If you’re serious about building generational wealth in [...]

Ep – 283 From Bankruptcy to a $100M Real Estate Vision with Jonathan St.Leger2026-03-02T05:31:35-05:00

Ep – 282 What’s Actually Holding Your STR Business Back

2026-02-23T06:39:54-05:00

Most entrepreneurs think they need better strategy. They don’t. In this Boardroom recap from the Freedom Factory, we unpack the real reasons businesses stall — and it’s not systems. It’s people, identity, and the state you operate from. Inside this episode: • Why most business bottlenecks are solved by the right “who” • The difference between hiring people and developing talent • W2 vs 1099 mistakes operators make • Why State → Story → Strategy is the real order of success • The 4 archetypes running your decisions (Warrior, Magician, Lover, Sovereign) • Why high performers get stuck in Warrior mode [...]

Ep – 282 What’s Actually Holding Your STR Business Back2026-02-23T06:39:54-05:00

Ep – 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip

2026-02-16T05:22:38-05:00

Vivian Yip went from corporate burnout at Apple to building a thriving midterm rental portfolio and property management company. In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income. We dive into: • Why community changes everything in real estate • The biggest mistake STR hosts make when pivoting to midterm rentals • Calendar discipline and how to control guest behavior • How to use data tools like PriceLabs the right way • Building multiple income streams without burning out • [...]

Ep – 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip2026-02-16T05:22:38-05:00

Ep – 280 – How Influencer Marketing Really Works for STRs (And Why Most Hosts Get It Wrong) with Madison Rifkin

2026-02-09T05:37:11-05:00

Most STR hosts misunderstand influencer marketing — and it’s costing them bookings. In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play. We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves. If you want more direct bookings, stronger brand trust, and a business that isn’t dependent on Airbnb alone, this episode is required listening. [...]

Ep – 280 – How Influencer Marketing Really Works for STRs (And Why Most Hosts Get It Wrong) with Madison Rifkin2026-02-09T05:37:11-05:00

Ep 279 – Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson

2026-02-02T12:02:27-05:00

Success in STR isn’t about age, capital, or the model you choose — it’s about conviction. In this episode, we sit down with Hayley Anderson, a 22-year-old operator already on her second business, to unpack the mindset, discipline, and leadership traits that actually drive growth. From failing early to building confidence through reps, this conversation goes far beyond arbitrage or co-hosting. If you want to scale your business — or your life — this episode will challenge how you think about comfort, confidence, and commitment. Inside the episode: • Why conviction matters more than experience • How confidence is built through [...]

Ep 279 – Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson2026-02-02T12:02:27-05:00

Ep 278 – How Great Leaders Scale Teams Without Losing Control with Ryan Leake

2026-01-26T08:49:58-05:00

Scaling isn’t a systems problem — it’s a leadership problem. In this episode, we break down what actually changes when you go from being a solo operator to leading a real team. From earning respect instead of demanding it, to building systems that support people (not suffocate them), this conversation unpacks the leadership shifts required to scale without chaos. If you’re growing doors, people, or partnerships — this episode will change how you think about leadership. Inside the episode: • The two ways leaders earn respect (and why only one works) • Why supporting team members’ goals makes you more valuable [...]

Ep 278 – How Great Leaders Scale Teams Without Losing Control with Ryan Leake2026-01-26T08:49:58-05:00

Ep 277 – Tech, Teams, and the Emotional Cost of Scaling STR Businesses with Frank Bosi

2026-01-19T05:52:30-05:00

Most operators think better tech will fix their problems. It won’t. In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality. Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt. Inside this episode: Why tech stack decisions are emotional, not logical How disconnected tools quietly create leadership stress The difference between [...]

Ep 277 – Tech, Teams, and the Emotional Cost of Scaling STR Businesses with Frank Bosi2026-01-19T05:52:30-05:00

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