This Couple Quit Their Jobs With One Land Deal
Katie and Brian Damaris, a husband-and-wife team from Pennsylvania, share how they built a land investing business that allowed Katie to leave her W2 job within 8 months and eventually enabled the family to live nomadically in places like Uruguay and Costa Rica. Over roughly 2.5 years, they grew from doing deals solo to running an 11-person remote team across multiple countries, generating over $200,000 net profit in Q1 of their third year.
Summary
The episode features Katie and Brian Damaris, a married couple currently living in Costa Rica while running a US-based land investing business. Brian was furloughed during COVID and initially turned to house flipping before discovering land investing through a podcast. He hired mentor Mike Balcom and began marketing via SMS texting, which was considered an unconventional channel at the time due to restrictions on land portals. Katie was initially resistant, working a W2 corporate job in sales leadership while pregnant with their second child, but eventually joined after recognizing her transferable skills in sales, team leadership, and recruiting would complement Brian's background in banking, construction management, and house flipping.
Their explicit goal was to get Katie out of her W2 job by a specific date — not a tentative timeline, but a committed deadline. Eight months into land investing, they achieved that goal. Their early deals included a $6,000 profit on their first flip and a $60,000 profit on their third deal that closed in just 7 days after putting a sign in the ground. This rapid ROI compared favorably to house flipping timelines and convinced them land was the right vehicle.
In terms of marketing, they chose SMS texting from the start because it offered faster response rates than mailers, which Brian had used for flips. They spent the first couple of months managing everything themselves before hiring, a deliberate decision rooted in Katie's corporate philosophy of never managing what you haven't personally done. An early mistake — hiring someone who claimed to handle all texting campaigns independently — reinforced this principle. Both of their initial part-time hires, one for SMS and one for comping/due diligence, are still with the company today.
The team has since grown to 11 members total, including employees in the Philippines, Egypt, Pakistan, and the US. Katie leads hiring and emphasizes culture-building through effective communication, shared commission structures, meaningful meetings, Discord-based casual interaction, paid holidays, PTO, and genuine investment in employees' personal wellbeing. The company has a zero percent voluntary turnover rate.
Deal-wise, the business focuses on traditional land flips and subdivides, with double closes being a newer and limited experiment. In Q1 of the current year, they achieved over $200,000 in net profit, still acquiring land at approximately 51% of market value. Brian is also building AI tools — including CRM API integrations, scraping tools for on-market properties, and a Chrome extension for comping — to increase operational efficiency without replacing human seller or agent relationships.
Personally, the family's nomadic lifestyle evolved from pre-kids world travel, through a month-long Florida stay, to a three-month school enrollment program in Uruguay, and finally to five months in Costa Rica with plans to move to Panama. Their two children, 16 months apart and now ages 4 and 5, attend local schools and are being immersed in Spanish and new cultures. The couple views the land business not as an end goal but as the financial vehicle enabling the life they've designed around family time, travel, and freedom.
Key Insights
- Brian argues that land investing offered far more exit strategies than house flipping, particularly the ability to hold seller notes as a passive income stream, which was a primary driver for switching vehicles.
- Katie claims that their success in getting her out of her W2 within 8 months was driven not by a 'give it a chance' mentality but by committing to a specific departure date and treating it as non-negotiable.
- Brian contends that their third land deal — a $60,000 profit closed in 7 days — was more impactful as proof of concept than any house flip because it matched flip-level profits with a fraction of the time commitment.
- Katie argues that hiring before you've personally done the job is a critical mistake, stating that her corporate leadership success was built on having done the frontline work herself, which earned team respect and enabled effective coaching.
- Brian states that in Q1 of their current year, every deal that went full cycle was acquired at 51% of market value, directly countering the belief that steep discounts are no longer achievable in land.
- Katie claims that the company has a zero percent voluntary employee exit rate, attributing it to transparent communication, shared commission structures that align team incentives, and genuine investment in employees' personal lives and goals.
- Brian argues that subdivide sellers often have enough market awareness to list at asking price, meaning that successfully closing those deals requires months of relationship-building, trust, and multiple difficult conversations rather than quick negotiation.
- Brian contends that AI will create a near-term fork in the road for land investors, where those who adapt tools like CRM API integrations, scraping utilities, and automated underwriting models will develop a compounding competitive advantage over those who don't.
- Both Brian and Katie explicitly state that AI tools in their business are designed to make human employees faster and more focused — not to replace them — and that seller and real estate agent relationships must remain fully human-to-human.
- Katie argues that they intentionally avoided shiny object syndrome by mastering land flips first for over a year before adding subdivides, and only revisiting double closes much later, ensuring each new deal type was supported by proven team structure and systems.
- Brian states they have maintained the same lenders for 2.5 years by treating those relationships carefully, and that funding networks like mastermind communities significantly lower the cost and friction of raising capital compared to cold outreach.
- Katie claims that their nomadic lifestyle was not a pre-planned destination but evolved incrementally — from a month in Florida, to three months in a school program in Uruguay, to five months in Costa Rica — with each step informed by meeting others living similar lifestyles.
Topics
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