$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.
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
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