$130K In Debt... Then He Found Land Investing
Thomas Cullen, a 28-year-old serial entrepreneur, shares his journey of starting a land flipping business while $130K in credit card debt, documenting his progress publicly on social media. Over five months, he evolved from flipping infill lots to builders into double-closing deals on rural land, generating $57K in profit. He emphasizes consistency, patience, and treating land investing as a sales and marketing business rather than a real estate business.
Summary
Thomas Cullen, a 28-year-old entrepreneur from New Jersey, joins the Real Estate Investing Podcast to discuss his first five months in land investing. His entrepreneurial background spans a decade and includes running a Google Ads agency for NYC construction companies, investing in crypto during the 2020 bull run, co-founding a small tech startup with a minor exit, consulting in the startup ecosystem, and eventually losing everything through a capital-intensive live event ticket brokering business combined with an expensive lifestyle.
Thomas began his land investing journey at rock bottom with over $130,000 in high-interest credit card debt and no cash, choosing to further max out his credit cards to fund the business. He deliberately chose not to purchase coaching or mentorship, instead self-educating through YouTube and social media content, though he acknowledges in hindsight that a mentor would have saved significant time. He simultaneously began documenting his journey daily on TikTok, Instagram, and YouTube under the brand 'Thomas Buys Land,' motivated by accountability, having nothing to lose, and recognizing the value of social media attention.
His first strategy was flipping infill lots to builders — a method he believed was the only approach based on what the algorithm was showing him. His first deal came when a Nashville builder found him on TikTok and DM'd him, resulting in a $5,000 profit. Three more similar deals followed. However, he quickly identified scalability problems with this model: builders have very specific and overlapping buy boxes, markets get exhausted via SMS quickly, and the business felt like chasing individual checks rather than building a pipeline.
Around day 50, Thomas discovered the double-closing model through social media, where investors secure rural land under contract and sell to a broader buyer pool — not just builders — often using real estate agents on platforms like Zillow. This was a transformative realization. His first double-close deal generated just over $32,000 in profit and was described as the easiest deal he had done. A subsequent double-close deal, while nearly falling apart multiple times, still yielded $5,000 and served as a major learning experience.
Thomas describes his current workflow as pulling lists of landowners, sending SMS outreach at scale (approximately 15,000 fresh leads and 30,000 texts per month in May), quickly filtering interested parties, giving price ranges rather than specific offers within 60 seconds of evaluating a property, and moving qualified sellers to phone calls as fast as possible. He emphasizes that land investing is fundamentally a sales and marketing business, not a boots-on-the-ground real estate business — he has never physically visited any land he has sold.
On sales technique, Thomas notes that he had to dial back the aggressive approach learned from cold-calling NYC construction workers and finance professionals. He now focuses on building rapid rapport by referencing area codes and shared geography, adjusting communication style based on the seller's demographic, and listening more than talking. He warns that competitors who offer inflated prices and then back out damage seller trust, creating additional hurdles for operators who follow through.
Thomas is approaching the point where hiring becomes necessary and is currently focused on understanding every part of the business before outsourcing, identifying system flaws that only become visible at higher volumes, and building a more predictable pipeline. He acknowledges the longer cash cycle of double-closing (potentially 90+ days) versus the infill-to-builder model but considers the trade-off worthwhile given the scalability. He is open to using private capital for deals that require actual purchases but remains cautious given his history with investor-dependent businesses.
His closing advice centers on the attention economy: the single greatest competitive advantage in 2026 is the ability to focus on one thing consistently for an extended period. He argues that most people abandon business models within three days, meaning that sustained effort over even 100 days or six months creates enormous separation from the competition.
About this episode
<p><strong>Want to quit your job and build a real land investing business?</strong><br /><a href="https://landportal.com/subscriptions?a_aid=LandInvestingOnline&a_bid=9e9b000b" rel="ugc noopener noreferrer" target="_blank"><strong>Land Portal</strong></a> gives you access to the fastest-growing land software <em>plus</em> <a href="https://landportal.com/subscriptions?a_aid=LandInvestingOnline&a_bid=9e9b000b" rel="ugc noopener noreferrer" target="_blank"><strong>Land Portal University</strong></a>, where we walk you step-by-step through getting your first land deal.<br /> Looking for <strong>1-on-1 Land Flipping or Subdividing coaching</strong>? Schedule a <a href="https://landinvestingonline.com/pages/consultation" rel="ugc noopener noreferrer" target="_blank"><strong>FREE strategy call</strong></a> here.</p><p><br />================================</p><p><br />In this episode, Ron sits down with Thomas Cullen to discuss how he built a profitable land investing business, while overcoming massive debt and documenting his journey online. Thomas shares his transition from infill lot assignments to larger double-close land deals, the marketing and sales strategies driving his growth, and the key factors that driven his success in his first few months of land investing</p><p><br />If you're looking to break into land investing and scale your deal flow, this episode is full of practical insights and motivation!</p><p><br />Connect with Thomas Cullen:<br /></p><ul><li><a href="https://www.youtube.com/@thomasbuysland" rel="ugc noopener noreferrer" target="_blank">YouTube</a></li><li><a href="https://www.instagram.com/thomasbuysland" rel="ugc noopener noreferrer" target="_blank">Instagram</a></li><li><a href="https://www.tiktok.com/@thomasbuysland?is_from_webapp=1&sender_device=pc" rel="ugc noopener noreferrer" target="_blank">TikTok</a></li></ul><p><br />================================</p><p><br />SOCIAL<br /><strong>Ron's Instagram </strong>: <a href="https://www.instagram.com/danielapke/" rel="ugc noopener noreferrer" target="_blank">https://www.instagram.com/ronapke/</a><a href="https://www.instagram.com/ronapke/" rel="ugc noopener noreferrer" target="_blank"></a><br /><strong>Dan's Instagram </strong>:<a href="https://www.instagram.com/danielapke/?hl=en" rel="ugc noopener noreferrer" target="_blank"> </a><a href="https://www.instagram.com/danielapke/" rel="ugc noopener noreferrer" target="_blank">https://www.instagram.com/danielapke/</a><a href="https://www.instagram.com/danielapke/?hl=en" rel="ugc noopener noreferrer" target="_blank"></a><br /><a href="https://www.instagram.com/danielapke/?hl=en" rel="ugc noopener noreferrer" target="_blank"></a><br />================================</p><p><br /><strong>TIMESTAMPS:</strong><br />00:00 – Intro<br />00:36 – Freedom of Entrepreneurship<br />08:39 – Recording the land journey<br />12:53 – Infill vs double closes<br />18:23 – SMS & Range offers<br />21:33 – First deals breakdown<br />23:33 – Sales strategy to buy land<br />28:06 – Adjusting & Consistency<br />31:26 – Scaling & Goals in 2026<br />39:49 – Closing a difficult deal<br />46:58 – Take control of your attention<br />48:10 – Outro</p>
Key Insights
- Thomas argues that the infill-lot-to-builder model is not scalable because builders share nearly identical buy boxes and SMS outreach can exhaust entire metropolitan markets within days, leaving no pipeline.
- Thomas claims his $32,000 double-close deal was simultaneously the easiest and most profitable deal he had done, suggesting that higher-complexity models do not necessarily require more effort than simpler ones.
- Thomas contends that land investing is fundamentally a sales and marketing business — he has never physically visited any property he has sold, and success depends on lead management, rapport-building, and follow-up rather than real estate knowledge.
- Thomas describes how competitors who offer inflated prices and then fail to close create a dual problem for legitimate operators: sellers develop false price expectations and distrust toward all buyers simultaneously.
- Thomas argues that outsourcing business functions too early is risky because operators may not fully understand how and why their own systems work, and hiring at 80% effectiveness in critical roles like sales can directly cause business failure.
- Thomas claims that giving sellers a price range rather than a specific offer — and anchoring to the low end on a phone call — allows deals to work at either end of the range, making the offer process faster and more flexible.
- Thomas asserts that documenting his journey publicly on social media served as a self-accountability mechanism and directly generated his first deal, when a Nashville builder found him on TikTok and DM'd him within the first 30 days.
- Thomas argues that in the attention economy, the ability to focus consistently on a single business for six months or more is the primary competitive advantage, because the vast majority of people abandon new business models within three days.
Topics
Transcript
All right, everybody, welcome back to the Real Estate Investing Podcast. Super excited to have Thomas Cullen on with me today. Thomas, we probably touched base. It was on Instagram when I first saw you, and I love the content you're putting out. You're very transparent with the way you're putting out land content. And I think you'll admit you're not the most experienced in this business right now, but you've been grinding. You have a really good story with just being, you start in the new year, so five months in, and you have really good experience. You kind of bootstrapped everything from what I remember, but welcome to the show, Thomas. Yeah, thanks for having me. I really…
Full transcript available for MurmurCast members
Sign Up to AccessMore from The Real Estate Investing Podcast
He Found the Land Deal Everyone Else Missed
Andrew Frezza, a one-year-old land investor and former CrossFit gym owner, shares his journey pivoting to real estate after COVID disrupted his fitness business. He discusses his early success with a $140K profit subdivide deal, his evolution from direct mail marketing to focusing on realtor relationships and on-market deals, and his upcoming major project—a 156-acre North Carolina property he expects to generate $300-400K profit from.
His First Land Deal Changed Everything
Brad Maulman, a six-month-old land investor, discusses his first deal—an 18-acre subdivision in Tennessee that he purchased for $220,000 and sold for $335,000, netting $61,000 with no money out of pocket. He shares how persistence through multiple funding rejections, strategic comping, logging opportunities, and breaking down complex problems into manageable steps led to his success despite numerous obstacles.
He Turned $10K Land Flips Into $60K Deals
Jack Watson shares how he scaled from simple $10K land flips to $60K+ land-home package deals by combining manufactured homes with raw land, qualifying buyers for traditional financing. He emphasizes niche focus, strategic marketing through direct mail and cold calling, and the importance of understanding construction management while maintaining quality contractor relationships.
Land Marketing Strategies & Environmental Due Diligence
A real estate investing podcast Q&A session covering land marketing strategies, motivated seller outreach, property subdivision procedures, and environmental due diligence. Key discussions include targeting specific buyer avatars with tailored messaging, identifying easements and utilities, and assessing infrastructure costs on small parcels.
How to Comp Defected Land
A live Q&A session from a real estate investing podcast focused on land flipping, covering topics like comping defected or wetland properties, handling unresponsive sellers, direct mail marketing results, and the growing role of AI tools in land investing operations.