Childhood companions Connor Swofford and Pieter Louw, whose friendship stretches back many years, decided in October 2024 to embark jointly on a new financial venture: investing in rental real estate. What began as a shared curiosity and a modest experiment in property ownership quickly transformed into a thriving enterprise. Within a single year, these longtime friends managed to expand their collective portfolio to an impressive 24 individual rental units spread across nine distinct properties situated in Buffalo, New York. Their rapid progress was made possible through the combination of imaginative financial structuring, disciplined planning, and the complementary nature of their individual talents.
Pieter Louw, who works as a real estate agent in Buffalo and possesses both engineering and construction expertise, described their partnership to Business Insider as a perfectly balanced union of strengths. He characterized himself as the practical, hands-on member of the duo—deeply familiar with construction, rehabilitation work, and the everyday operational realities of maintaining and improving multi-unit rental properties. In contrast, he portrayed his business partner, Connor Swofford, as the strategic mind and organizational powerhouse behind the operation. According to Louw, Swofford’s capacity to manage systems, streamline communications, and maintain long-term strategic focus has been crucial to their continued expansion.
Swofford, who lives in Charleston and works professionally as a startup consultant, approaches their real estate business with the precision and efficiency of someone used to managing multiple projects simultaneously. His focus has been on automating and refining their work processes so that the pair can continue developing their property portfolio without allowing it to overtake their primary careers or personal lives. Although real estate represents merely a side endeavor for both of them, they treat it with a high level of professionalism and structure. To keep both operational and strategic matters aligned, they meet virtually twice each week for approximately half an hour, using these check-ins to discuss updates, analyze financial performance, and evaluate potential acquisitions. In terms of personal time commitment, Swofford reports dedicating no more than two hours per week to tasks directly related to their holdings, while Louw, who handles on-site responsibilities such as supervising contractors and meeting with tenants, averages roughly ten hours weekly, though this varies depending on ongoing renovation projects.
Reflecting on their unexpected success, Louw noted that what started as a casual side project between friends—a small, enjoyable challenge meant to test their understanding of the property market—has evolved into something substantially larger. Despite that growth, the spirit of the original endeavor remains: it continues to be, at its core, a collaborative and enjoyable pursuit rather than a burdensome second career. Both partners, now 31 years old, intend to preserve that balance going forward. Their plan is to maintain real estate as a supplementary source of income, using its cash flow to fund personal goals such as family vacations, contribute to retirement savings, and build educational funds for their children’s futures.
A major factor in their ability to scale rapidly while keeping their workloads minimal has been their deliberate use of technology, particularly a carefully selected collection of software tools that leverage artificial intelligence. This streamlined system, costing only $20 per month, forms what they describe as their “software stack.” It enables the duo to handle all critical business functions—banking, bookkeeping, tenant management, coordination with contractors, and more—with remarkable efficiency.
The principal component of this stack is Baselane, an all-in-one platform combining digital banking, bookkeeping, and rent collection features specifically designed for landlords and property managers. Swofford encountered Baselane during his research into landlord software and business banking solutions, and it quickly became indispensable to their operations. It is the only platform in their toolkit that requires payment, and at just twenty dollars monthly, the investment has proven exceptionally worthwhile. Through Baselane, they collect monthly rent payments, receive automatic reminders if tenants miss deadlines, categorize and track all expenses, pay contractors directly, and even earn competitive interest on funds held within their business accounts. The platform’s integrated analytics allow them to monitor the financial health of each property, interpret key performance indicators, and identify emerging trends that could influence their strategic decisions. For instance, data provided by Baselane revealed that smaller two-unit properties in their local market were delivering lower returns than larger multifamily buildings. This insight guided a shift in their acquisition strategy: the partners now focus primarily on properties with three to ten units, where potential profitability and scale efficiency are greater.
Their second digital tool, Asana, plays a complementary role by supporting the organizational backbone of their workflow. Using the free version of the project management platform, they delegate specific tasks to contractors, track progress, and ensure that construction and maintenance work remains on schedule. Because their investment approach follows the BRRRR method—buy, rehab, rent, refinance, repeat—they frequently acquire undervalued properties that require renovation before they can become profitable rental assets. Asana enables them to manage these improvement projects seamlessly, from large-scale unit remodels to routine maintenance requests submitted by tenants. Each task is clearly documented, assigned, and monitored, ensuring that nothing falls through the cracks.
Rounding out their efficient technology suite is ChatGPT, an AI assistant they employ for a range of practical uses, from drafting professional correspondence and composing listing descriptions to clarifying real estate laws and advising on challenging landlord-tenant situations. The tool proved especially valuable when they faced their first eviction process—a scenario they hadn’t previously encountered. By leveraging conversational AI, they obtained quick, well-organized explanations regarding legal obligations, documentation protocols, and proper communication with tenants. Over time, ChatGPT has also become a reliable assistant for everyday inquiries, helping streamline small but necessary administrative tasks.
Together, these three resources—Baselane, Asana, and ChatGPT—constitute the foundation of their operations, all designed to reduce inefficiency and empower two busy professionals to manage a growing real estate venture in just a few hours each week. As Swofford summarized, their total expense currently stands at only twenty dollars per month, with two of the tools available entirely for free.
Ultimately, their goal is not merely to minimize manual effort but to use modern technology to become more responsive, communicative, and responsible landlords. Louw emphasizes that good property management extends beyond financial success; it relies heavily on cultivating positive relationships with tenants. He has observed that when landlords demonstrate consistent respect—responding quickly to issues, maintaining properties properly, and communicating transparently—tenants, in turn, exhibit greater care toward their living spaces. This philosophy, combined with a thoughtfully built digital infrastructure and a partnership rooted in trust and complementary ability, has allowed Swofford and Louw to transform a simple idea into a highly efficient, steadily expanding investment operation.
Sourse: https://www.businessinsider.com/real-estate-investing-portfolio-ai-software-tools-brrrr-method-property-2025-10
