EP 249 From Trailer Rentals to Content Creation: The Kyle Biggs Story
Tue Feb 03 2026
Send us a text
In this episode of The Days Grimm, Brian Michael Day and Thomas Grimm sit down with long-time friend, entrepreneur, and DIY content creator Kyle Biggs to discuss the realities of building a business and a real estate portfolio from the ground up. Kyle shares his journey from running a trailer rental business to successfully "house hacking" three different properties by living in them and driving "soft value" through smart, budget-friendly renovations.
If you’ve ever felt overwhelmed by home repairs or wondered how to transition from a 9-to-5 into real estate, this episode provides a grounded, no-nonsense perspective. Kyle breaks down his "lazy-proof" philosophy for home maintenance famously featured in his TikTok series and explains why most people are just one YouTube tutorial away from saving thousands of dollars on home projects.
Beyond the hammer and nails, the conversation dives deep into the mindset of an entrepreneur. Kyle candidly discusses his "first failure" with KB Trailer Rentals and the invaluable lessons he learned about scalability, accounting, and trusting your gut when dealing with difficult clients. We also explore the future of content creation, including how Kyle uses AI tools like Gemini to plan his videos and the technical hurdles of moving from phone editing to professional software like DaVinci Resolve.
Whether you're looking for actionable real estate advice or just need a kick in the pants to clean out your air vents, this episode is packed with authentic stories and practical takeaways for the modern blue-collar entrepreneur.
KEY TOPICS COVERED:
The "House Hacking" Strategy: How to buy, renovate, and rent properties while living in them.Driving "Soft Value": Why kitchen and bathroom updates offer the best return on investment.Lessons from Business Failure: What shutting down a trailer rental business taught Kyle about scalability.The Power of YouTube University: Learning complex trades like plumbing and drywall for free.Property Management: When to stop doing the work yourself and hire a pro for passive income.Content Creation Workflow: How to film and edit high-performing TikToks in under 30 minutes.AI for Entrepreneurs: Using deep research models to plan a 50-video content strategy.NOTABLE QUOTES:
"YouTube is where I learned my shit. For real. 100%." (Kyle Biggs) "Trust your gut and know when to refuse service to anybody you want." (Kyle Biggs) "Passive income... that’s really what it’s about. You can go to sleep and still have that money coming in." (Thomas Grimm) "Be original, be yourself, don't f*****g fake it till you make it. Just do the shit you like doing." (Brian Michael Day) If you enjoyed Kyle’s no-nonsense approach to DIY and business, hit the subscribe button and let us know in the comments: What is the one home repair project you’ve been putting off because you’re "too lazy" to start? Don't forget to like and share this episode with someone looking to start their real estate journey!
TIMELINE:
00:00 - Introduction and the "clown shoes"
06:38 - Transitioning from trailer rentals to real estate
10:59 - The "Ho
[The Days Grimm Podcast Links]
- YouTube: https://www.youtube.com/c/TheDaysGrimm
- Our link tree: linktr.ee/Thedaysgrimm
- GoFundMe account for The Days Grimm: https://gofund.me/02527e7c
[The Days Grimm is brought to you by]
Sadness & ADHD (non-medicated)
More
Send us a text In this episode of The Days Grimm, Brian Michael Day and Thomas Grimm sit down with long-time friend, entrepreneur, and DIY content creator Kyle Biggs to discuss the realities of building a business and a real estate portfolio from the ground up. Kyle shares his journey from running a trailer rental business to successfully "house hacking" three different properties by living in them and driving "soft value" through smart, budget-friendly renovations. If you’ve ever felt overwhelmed by home repairs or wondered how to transition from a 9-to-5 into real estate, this episode provides a grounded, no-nonsense perspective. Kyle breaks down his "lazy-proof" philosophy for home maintenance famously featured in his TikTok series and explains why most people are just one YouTube tutorial away from saving thousands of dollars on home projects. Beyond the hammer and nails, the conversation dives deep into the mindset of an entrepreneur. Kyle candidly discusses his "first failure" with KB Trailer Rentals and the invaluable lessons he learned about scalability, accounting, and trusting your gut when dealing with difficult clients. We also explore the future of content creation, including how Kyle uses AI tools like Gemini to plan his videos and the technical hurdles of moving from phone editing to professional software like DaVinci Resolve. Whether you're looking for actionable real estate advice or just need a kick in the pants to clean out your air vents, this episode is packed with authentic stories and practical takeaways for the modern blue-collar entrepreneur. KEY TOPICS COVERED: The "House Hacking" Strategy: How to buy, renovate, and rent properties while living in them.Driving "Soft Value": Why kitchen and bathroom updates offer the best return on investment.Lessons from Business Failure: What shutting down a trailer rental business taught Kyle about scalability.The Power of YouTube University: Learning complex trades like plumbing and drywall for free.Property Management: When to stop doing the work yourself and hire a pro for passive income.Content Creation Workflow: How to film and edit high-performing TikToks in under 30 minutes.AI for Entrepreneurs: Using deep research models to plan a 50-video content strategy.NOTABLE QUOTES: "YouTube is where I learned my shit. For real. 100%." (Kyle Biggs) "Trust your gut and know when to refuse service to anybody you want." (Kyle Biggs) "Passive income... that’s really what it’s about. You can go to sleep and still have that money coming in." (Thomas Grimm) "Be original, be yourself, don't f*****g fake it till you make it. Just do the shit you like doing." (Brian Michael Day) If you enjoyed Kyle’s no-nonsense approach to DIY and business, hit the subscribe button and let us know in the comments: What is the one home repair project you’ve been putting off because you’re "too lazy" to start? Don't forget to like and share this episode with someone looking to start their real estate journey! TIMELINE: 00:00 - Introduction and the "clown shoes" 06:38 - Transitioning from trailer rentals to real estate 10:59 - The "Ho [The Days Grimm Podcast Links] - YouTube: https://www.youtube.com/c/TheDaysGrimm - Our link tree: linktr.ee/Thedaysgrimm - GoFundMe account for The Days Grimm: https://gofund.me/02527e7c [The Days Grimm is brought to you by] Sadness & ADHD (non-medicated)