Michael Eichler & jonathan Dempsey
Live Free Podcast
Welcome to Live Free Podcast where Host Jonathan Dempsey (JD) & co-host Mike Eichler cover their experience in the spectrum of real estate. Topics covered include how to get started with real estate, short-term rentals, arbitrages, turnkey investment, ground-up construction, the BRRR method, and seller financing. If you are looking to get started with real estate to build passive income, you are in the right place!
Author
Michael Eichler & jonathan Dempsey
Category
Podcast website
Latest episode
Dec 8, 2025
Where to listen?
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Episodes
Update on the Best and Worst HOA's in the Poconos Market 08.12.2025 1:01:18
We're back! Hopefully you didn't miss us too much :). Joining me today is Alec Santiago, an agent and property manager who has been focused on this market for a few years. We will dive in and give an update with a new list of HOAs that we find more or less favorable to STR in this market. Listen in and gain a deeper understanding of where to place your chips in this current state of the short-term...
Elements a Modern Poconos STR Resort Update! 10.07.2023 41:29
Listen in to this episode where Mike and JD talk everything Elements Resort. How the renovations are going what we have been able to accomplish in Seven short months here. We go through all of the great milestones we were able to reach and out plans to finish off strong.
Chasing Your Passion & Living Free with Hawaiian Actor, Model and Personality Pat Mullen 14.02.2023 57:48
In this episode, we walk through Pat’s journey from zero to making a career LA bound and star on famous TV series "Too Hot to Handle". Fueled by a desire to be something more, Pat details how as an entrepreneur he stays focused, uses visualization, and networks to continue leveling up.
"How this Food Truck Entrepreneur turned Real Estate Investor with Nick Loukas" 18.01.2023 53:45
Listen to this episode, where we invite our friend Nick Loukas to explain how he went from pharmacist to Food Truck Operator and Real Estate investor. Nick explains how he started his "Slide On By" business out of a tent offering free food to his neighbors. Nick talks about how he bought back his time and plans to grow and scale his business and investments.
Presenting "Element an All Seasons Pocono Resort" 43 unit Poconos Resort 17.12.2022 45:46
The Live Free Team is pleased to present our newest project. "Element an All Seasons Pocono Resort" The team has been hard at work renovating the cabins and hotel units to bring them back to not just their former glory, but even better than before. Listen in to hear their endeavors so far and their big plans to make this resort unforgettable and the next big thing in the Poconos.
The Best and Worst Poconos HOA's for Short Term Rental 04.12.2022 42:46
In this week's episode of the Live Free Podcast, Mike and JD talk about what an HOA is, as they are very prevalent in the Poconos market. Next, hosts Mike and JD discuss the negatives and positives of being in an HOA. Finally, they discuss their tier list of our favorite and least favorite HOA in the Pocono market.
Obtaining 10 Houses in your first year in real estate with prodigy Josh Hooper 16.11.2022 49:58
In this week's episode, we interview young star Josh Hooper an entrepreneur who went from 0 to 10 Homes in his first year while using a well know strategy called the BRRR method. Listen in to how Josh was able to make it happen all while only being 22 years old.
"How Investor and Luxury Construction Expert Agent Marco DiGabriele went from Zero to Top Producer & Avid Investor" 09.11.2022 1:01:17
In this episode, we walk through Marco’s journey of investing in & managing luxury new development projects. We dive to into entering the Philadelphia market, building the Life on Broad Philly based real estate brand, navigating Philadelphia zoning, & how Marco is able to deliver value to his investors, friends & family through his immersion in real estate.
"How newly-weds Skyler and Michelle Lash built a successful real estate portfolio from out of State" 19.10.2022 58:20
In this episode, we invite our good friends Skyler and Michelle Lash, recently married investors who do their investing from afar. Listen to learn the challenges they faced and how much they learned from investing from states away. Also, learn how much they were able to accomplish being so far away and what they were able to realize about investing from so far away.
"How to build a successful clothing brand in today's market with young entrepreneur, Harrison Wells owner of Imperfect " 05.10.2022 50:53
Listen in to this crazy episode with young entrepreneur Harrison Wells, owner of Imperfect- a clothing brand company that donates a portion of its earnings to mental health-related charities. Harrison goes over everything it took to get started and how you can too.
"How to win in Real Estate with Rob Chiang, experienced investor with over 25 years in the investing game." 28.09.2022 57:10
In this week's episode, we invite guest Rob Chiang, investor and author of " 7 Step Blueprint to Passive Wealth" an amazon best seller, as well as, an apartment manager, Real estate Broker. Rob is also experienced in buying selling, renting managing, maintenance, remodeling, and portfolio owner of over 10 Million.
Poconos, Poconos and more Poconos, Lake Front houses, Acela train and Margaritaville!? 25.09.2022 51:22
Tune in to this fire episode where we talk over all of the crazy cool things going sown in the Poconos, the current real estate climate for buying and selling, and the awesome things coming in the Poconos market, you do not want to miss this one!
"How you can always make a real estate deal work" 15.09.2022 30:19
In this week’s episode Mike and JD talk about different ways to get a deal to close regardless if you have or don’t have cash, income, experience or the time to invest. We dive deep into the philosophy of what makes a effective partnership, how to find the right partner, and how to pivot to ensure your real estate journey gains momentum.
Ways to Finance Your next Deal with Seasoned Loan Expert Justin Rosenhaus 09.09.2022 39:01
Listen to this episode, with guest star long-time loan expert Justin Rosenhaus. Justin breaks down everything you need to get a deal closed and all the different ways you can finance a deal.
Questions from a first time investor- How you can get started 01.09.2022 46:49
Listen in to this week's podcast where newbie investor Carrie Hyrowski asks us a ton of questions from how much money should I have in the bank, to what should I look for when I buy, and what should I do to get started in the real estate game. Tune in for tons of insightful questions on the real estate investing game as a whole.
"Is this the end for STR in Philly? and where we think STR will move to" 25.08.2022 43:59
Tune into this week's Live Free podcast to hear hosts Mike and JD talk about the current climate of Airbnb/Short Term Rental in Philadelphia, How it used to be like, how it is now, and how it is going to change with regulations looming. Stay til the end to hear what they think the future of STR will look like and how ut might change dramatically.
What motivates us to do the things we do 17.08.2022 41:01
Tune in to episode 10! to hear about why we got started in real estate and investing, and why we continue to fight on in this career to build the dream lifestyle that we crafted for ourselves.
Different Real Estate investment options, and why they may work for you 10.08.2022
Listen in to this episode where we talk about all the differents strategies in real estate and the benefits and disadvantages of each. We give our experience and thoughts on each one and why we would or would not do each strategy.
Tennessee Market Deep Dive- Nashville, Chattanooga, Gatlinburg 03.08.2022 36:00
In this episode, Mike and JD take a prospective look at 3 new markets that they are analyzing to start investing in potentially. The markets of Nashville, Chattanooga, and Gatlinburg, listen all the way through to see what they have found out about these markets.
Ep.7 Achieving Financial Freedom with Will Fulton 27.07.2022 1:03:15
Tune in this week to the Live Free Podcast, where we take financial literacy teacher Will Fulton, and dive deep into how he invests to gain financial independence himself and how he continues to teach many more each and every day.
"Vacation Hacking" With your Short Term Rental 20.07.2022 39:47
In this episode, Mike and JD explain their new term "Vacation Hacking", a slight twist on "House Hacking" an excellent strategy for getting your second rental property without putting down 20%. Stick around for a Deep dive into one of their best-performing properties in the Poconos market.
Live Free Podcast Ep. 5 "Operations for a 200+ property management company" 13.07.2022 57:43
Listen in to this podcast where we cover all things operations for taking a property management company from 10 to over 200 units in as little as 2 years
Live Free Podcast Ep. 4 " Crazy 16 Unit deal in North Carolina" 06.07.2022 30:32
Today in the Live Free Podcast Mike and JD talk about a new crazy deal that they have put together in wonderful Healing Springs North Carolina, listen in to hear how they got financing, how they plan to improve the property and all in all provide a ton of value to the investors who jumped in to make the deal happen.
Live Free podcast Ep. 3 "Onboarding a New Short Term Rental Unit" 29.06.2022 26:06
In this episode listen to Mike and JD talk about all things needed to get from scrolling Zillow to getting booking after booking on Airbnb. Starting with closing and then furnishing and designing your home, to compete with all other hosts. Stick around till the end to hear some tips and tricks to add extra value to your guests and extra cash to your pocket.
Live Free Podcast Ep. 2 "43" Unit Poconos Deal 22.06.2022 28:33
Today in the Live Free podcast we take a deep dive into the numbers and everything that went into what might turn out to be one of our best deals that we have done, a 43-unit deal in the heart of the Poconos, Pennsylvania. Tune in to figure out how the mastermind behind it pulled it off with financing less than 20% of the total cost and rehab costs
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