Ep. 103 How Evan Cassidy Survived His First Airbnb Investment
Mon Dec 01 2025
In this episode of the RE Social Podcast, hosts Vince Rodriguez and Andrew McCormick talk with Evan Cassidy, our former producer, standup comedian, and emerging real estate investor, to unpack the roller coaster journey of buying, renovating, and managing his first investment property in Yucca Valley. He opens up about what inspired him to jump into real estate, how the pandemic turned his initial renovation plans upside down, and the financial and emotional challenges that come with navigating your first Airbnb. The hosts dig into Evan’s biggest lessons around building the right team, understanding market cycles, managing cash flow, and developing the patience and resilience needed to succeed as an investor. Evan also reveals how he balances family life with creative pursuits, and how both comedy and real estate continue to shape his long-term vision. Listen to this episode to learn more!
Key Takeaways
00:00:00Welcome to the RE Social Podcast
00:01:08Let’s get to know Evan Cassidy
00:05:09The Joshua Tree Investment
00:12:06Financials and Future Plans
00:25:43Stocking and Organizing Supplies
00:28:51Setting Up an Ideal Airbnb
00:33:25Challenges and Lessons Learned
00:44:41Hiring and Building a Reliable Team
00:53:44Exploring New Real Estate Opportunities
00:54:42Long-Term vs. Mid-Term Rentals
00:58:54Credit Card Hacks and Bank Reactions
01:01:24Lessons Learned from Investments
01:04:38The Importance of Risk Tolerance
01:21:53Blend of Comedy and Real Estate
01:23:36How to connect with Evan
Resources and Links
Find his schedule on Instagram: https://www.instagram.com/thenextwavecomedy/
Evan’s Yucca Valley Property http://www.casafreebird.com/
Connect with Evan
https://www.instagram.com/thecassmanshow/
https://www.facebook.com/thecassman
https://www.youtube.com/c/fockyanation
Need Help? BOOK A CALL:
https://anviinvest.com/consulting/
Learn more about AnVi Invest 🏠
RATE US! https://linktr.ee/resocialpodcast
SUBSCRIBE! https://www.youtube.com/@anviinvestment
WEBSITE: https://anviinvest.com/
LINKEDIN: https://www.linkedin.com/in/anvi-investments/
INSTAGRAM: https://www.instagram.com/anviinvest/
FACEBOOK: https://www.facebook.com/anviinvest/
More
In this episode of the RE Social Podcast, hosts Vince Rodriguez and Andrew McCormick talk with Evan Cassidy, our former producer, standup comedian, and emerging real estate investor, to unpack the roller coaster journey of buying, renovating, and managing his first investment property in Yucca Valley. He opens up about what inspired him to jump into real estate, how the pandemic turned his initial renovation plans upside down, and the financial and emotional challenges that come with navigating your first Airbnb. The hosts dig into Evan’s biggest lessons around building the right team, understanding market cycles, managing cash flow, and developing the patience and resilience needed to succeed as an investor. Evan also reveals how he balances family life with creative pursuits, and how both comedy and real estate continue to shape his long-term vision. Listen to this episode to learn more! Key Takeaways 00:00:00Welcome to the RE Social Podcast 00:01:08Let’s get to know Evan Cassidy 00:05:09The Joshua Tree Investment 00:12:06Financials and Future Plans 00:25:43Stocking and Organizing Supplies 00:28:51Setting Up an Ideal Airbnb 00:33:25Challenges and Lessons Learned 00:44:41Hiring and Building a Reliable Team 00:53:44Exploring New Real Estate Opportunities 00:54:42Long-Term vs. Mid-Term Rentals 00:58:54Credit Card Hacks and Bank Reactions 01:01:24Lessons Learned from Investments 01:04:38The Importance of Risk Tolerance 01:21:53Blend of Comedy and Real Estate 01:23:36How to connect with Evan Resources and Links Find his schedule on Instagram: https://www.instagram.com/thenextwavecomedy/ Evan’s Yucca Valley Property http://www.casafreebird.com/ Connect with Evan https://www.instagram.com/thecassmanshow/ https://www.facebook.com/thecassman https://www.youtube.com/c/fockyanation Need Help? BOOK A CALL: https://anviinvest.com/consulting/ Learn more about AnVi Invest 🏠 RATE US! https://linktr.ee/resocialpodcast SUBSCRIBE! https://www.youtube.com/@anviinvestment WEBSITE: https://anviinvest.com/ LINKEDIN: https://www.linkedin.com/in/anvi-investments/ INSTAGRAM: https://www.instagram.com/anviinvest/ FACEBOOK: https://www.facebook.com/anviinvest/