Short Term Rental Secrets Podcast

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply Check out our free 6 step course: https://level.strsecrets.com/pc-book If you want to join these live trainings: https://www.facebook.com/groups/STRentalsecrets If your listings aren't getting booked right now — don't panic and drop your prices. In this week's T...

Connect with Sean: Instagram: https://www.instagram.com/sean_bakhtiari/ Check out Seacoast 2 Summit: https://www.seacoast2summit.com Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets What happens when a corporate finance guy from Boston decides he's done working for someone else — a...

Connect with Jeremiah: Instagram: @jeremiahkwatson Business: www.affluentvacays.com Check out our free 6 step course: https://level.strsecrets.com/pc-book STR Secrets FB group https://www.facebook.com/groups/STRentalsecrets He did everything people told him to do. Got clean. Went to college. Got a good job. Made good money. And he was still unhappy. In this episode, we talk with Jeremiah Watson. J...

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 shar...

Want the resources mentioned in the training? Instagram ➡️ https://www.instagram.com/mikereillync/ Follow this link for the Free training: https://level.strsecrets.com/pc-book You want to grow a property management business, you will eventually hit the same wall: You become the person slowing things down. In this video, I share the exact playbook we built before hiring our first salesperson. Insid...

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 turn...

2026 is going to separate serious operators from everyone else. Supply is rising. Middle-class travel is tightening. Occupancy is projected to decline. Rates are compressing. If your Airbnb still looks like 2024… you're in trouble. In this training, I break down my full 4-step photography system: – What to upgrade BEFORE hiring a photographer – How to properly interview lifestyle photographers – W...

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 mistak...

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 bigge...

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 ca...

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 y...

The STR market isn’t crashing — it’s recalibrating. In this episode, we break down AirDNA’s 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win. This is a data-backed walkthrough of what’s changing, why it matters, and exactly what to d...

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, o...

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 oper...

Your goals aren’t failing — your calendar is. In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time. This conversation dives deep into identity, courage, time audits, consistency, and th...

The STR game has changed—and most operators haven’t caught up. In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets. This isn’t theory. It’s what’s working right n...

Most people don’t fail because they lack discipline — they fail because they’re trying to grow without changing who they are. In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habi...

Most entrepreneurs focus on tactics — but the real breakthroughs happen internally first . In this episode, Stacey St. John breaks down how self-awareness, intuition, mindset, and values-driven leadership shape long-term success in business and life. From recognizing limiting beliefs to building aligned teams and managing energy, this conversation goes far beyond surface-level motivation. If you’v...

AI isn’t a tool anymore — it’s infrastructure. In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale. From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who...

Your STR isn’t underperforming by accident — it’s underperforming because of decisions. In this episode, Chris and E sit down with Mark Lumpkin from STR Cribs, the company behind 500+ STR setups, to break down the real reasons properties fail and what the best operators do differently. If you’re buying, designing, furnishing, or managing STRs — this is a masterclass in thinking like a pro instead...

Your business can’t outgrow the identity you’re stuck in. In this episode, Bernie Cesareo reveals the mindset and identity shifts that transformed his life, his confidence, and his STR businesses — from shrinking portfolios to scaling multiple companies with clarity and purpose. This episode breaks down the real reason most hosts stay stuck, how to think and act like a CEO, and the inner work requ...

The arbitrage era is cracking — fast.   With Sonder filing bankruptcy and operators across the country getting crushed by fixed leases, the truth is clear: the STR model you choose determines whether you scale… or sink. In this episode, we break down  why arbitrage is failing , what Sonder’s collapse teaches every host, and why  co-hosting remains the most profitable, low-risk, scal...

In this episode, Chris and E sit down with the founder of Vintory to uncover the real reason PMs fail, what the top managers are doing differently, and how to build a predictable machine for owner acquisition. Whether you're starting with 5 doors or aiming for 500, Brooke breaks down the playbook that actually works. Inside this episode: • Why most PMs never break past 50–100 properties • The REAL...

Your STR business is worth more than you think—if you build it the right way. In this episode, we break down the difference between operators who burn out… and operators who build real companies that survive, scale, and eventually sell for life-changing money. We also cover the hard lessons from companies that grew too fast, collapsed, or went bankrupt—and how to avoid their mistakes. In this epis...

The STR industry is shifting — and this episode marks the beginning of a new era.  Recorded LIVE inside the brand-new Freedom Factory, Mike, E., Chris, and Reilly break down the mindset, seasons, strategy, and direction that will define the next 5 years of short-term rentals… and your future in it. • The story behind building the Freedom Factory • Mike’s “origin moment” and how it shaped everythi...