The Dillon England Show

This Investor Owns 250 Doors… Here's the ONE He'd Buy Again | Peter Skaggs

September 4, 2026·51 min
Episode Description from the Publisher

Peter Skaggs runs a mortgage company and a 250 door real estate portfolio, and he built both at the same time without quitting his day job.He bought his first investment property in 2007. Then 2008 happened. By 2011 the house had lost half its value. He held on anyway. For fourteen years. He also spent years chasing apartment complexes, land, and short term rentals before realizing he was collecting real estate, not building a portfolio.He sold that crashed property in 2021 for almost double what he paid. That experience is where his framework came from. Buying power, staying power, growing power. Now he teaches busy professionals how to build a 10 to 20 property portfolio that runs quietly in the background while they do everything else.What we covered: → Why he chose single family homes over apartments, storage units, and short term rentals → What actually happened when he held a crashed property for fourteen years → The real numbers behind reaching financial freedom with 10 to 20 rental properties → Why Airbnbs make sense as a lifestyle asset, not a starting point → The framework he built after making almost every mistake in the bookThe people who get rich slowly in real estate are the ones nobody writes books about. Peter has spent 20 years proving that boring wins.Thanks for making the trip and handing over 20 years of lessons in under an hour.*Connect with Peter Skaggs*https://www.linkedin.com/in/petertskaggs/https://www.instagram.com/petertskaggs/https://www.facebook.com/petertskaggs/*Chapters*00:00 Intro01:25 Peter's 250 door portfolio and 20 years in real estate02:32 Collecting real estate versus building a real portfolio05:23 Where beginners should start: single family, Airbnb, or apartments10:14 The real numbers behind financing your first rental14:21 The freedom flywheel: how 10 to 20 properties add up to financial freedom23:07 Buying right before the 2008 crash and holding for 14 years27:23 The expensive mistakes that led to his framework31:54 Real estate funds and syndications versus owning it yourself38:56 Airbnbs as a lifestyle asset and the free deal analyzer toolThank You for Watching The Dillon England Show!Become a supporter of this podcast: https://www.spreaker.com/podcast/the-dillon-england-show--6370921/support.*Connect with Dillon*https://www.instagram.com/thedillonenglandshow/https://twitter.com/imdillonenglandhttps://www.linkedin.com/in/dillonmengland/https://www.facebook.com/dillon.england.5*Sponsor — Broadcast Brew (Low-Acid Coffee)*Order our LOW ACID COFFEE “THE BROADCAST BREW”Thank you to Cool Beans Coffee Brewery for your partnership.https://www.coolbeanscoffeemi.com/product-page/broadcast-brew-low-acid-blend*ABOUT THE DILLON ENGLAND SHOW*Authentic conversations with interesting people across personal growth, entrepreneurship, and lifestyle — direct, faith-forward, Detroit grit.Subscribe for full conversations and weekly clips.Share this with someone on your leadership team.Comment your biggest takeaway.

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