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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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 required to grow a business that matches the life you want.
Inside this episode:
• The identity upgrade that changed Bernie’s life
• How self-image controls your STR results
• Why talking about your vision attracts the right people
• The shift from operator → leader → CEO
• How Bernie built multiple businesses by delegating
• Why gratitude, belief, and clarity fuel massive growth
00:01:12 – Bernie’s Big Mindset Shift: Stop Doing Everything Yourself
00:04:07 – “Assume the Wish Fulfilled”: Rewriting Your Identity
00:08:10 – Manifesting the Dream Jeep: Breaking 30 Years of Beliefs
00:11:20 – Running Multiple STR Businesses Through Identity Upgrades
00:14:36 – Lifestyle Freedom: Why Bernie Never Misses His Son’s Games
00:17:00 – The Elder-Care Village Vision: Thinking Bigger Than STR
00:20:12 – From Player to Coach to CEO: Letting Go of Control
00:24:18 – Correcting Systems, Not People: Real Leadership
00:28:55 – How Speaking Your Vision Attracts the Right Opportunities
00:33:42 – Gratitude, Belief, and the Identity That Builds Your Future
Guest Bio:
Bernie Cesareo and his wife Courtney started the company by turning a long-term rental in their hometown into a short-term rental and doing everything themselves from guest support to cleaning and maintenance. Happily surprised with the success and popularity of this property, they decided to turn this side hustle into a primary business. They loved providing quality accommodations and creating great value for their guests and felt they could do this on a larger scale. They started growing the business by becoming co-hosts for other property owners and have added team members to help make everything run smoothly. After several years, they have a team of 8 that manages anywhere from 20-40 properties.
Guest Link:
https://eaglestays.com/
Get FREE Access to our Community and Weekly Trainings:
https://group.strsecrets.com/
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