Connor Swofford and Pieter Louw
- Connor Swofford and Pieter Louw scaled their rental portfolio to 24 units in Buffalo.
- Despite scaling quickly, rental real estate remains a low-lift side hustle for the friends.
- They use Baselane, Asana, and ChatGPT to manage tasks and streamline their operations.
Childhood friends Connor Swofford and Pieter Louw started investing in rental properties together in October 2024.
In the last 12 months, they’ve scaled their joint portfolio to 24 units across nine properties in Buffalo, thanks to creative financing and their combined skillsets.
“I’m very good at the boots on the ground, knowing the construction side of things,” Louw, who is a real estate agent in Buffalo with a construction and engineering background, told Business Insider. “And Connor is an absolute menace when it comes to organization and the bigger picture things.”
Swofford, a startup consultant, lives in Charleston and focuses on streamlining their workflow so that they can continue to grow their portfolio while still treating it as a side hustle.
The friends and business partners meet twice a week virtually for about 30 minutes to discuss their holdings and prospective deals. Swofford said he spends no more than two hours a week on portfolio-related tasks. Louw, who’s on the ground visiting job sites and showing apartments, said his time commitment fluctuates but that he spends, on average, 10 hours a week on their joint portfolio.
“The partnership has kind of flourished,” said Louw. “It was just supposed to be this little fun thing that we do, and that’s still what it is, but it’s grown into something bigger than I think we might have both expected it to.”
Swofford and Louw, both 31, plan to keep it as a side hustle, using the cash flow to pay for vacations, boost their retirement savings, and contribute to their kids’ future educations.
They shared their “software stack,” which has allowed them to scale quickly without sacrificing a lot of their time. It consists of three AI tools and costs $20 a month.
1. Baselane. While researching landlord software and business banking platforms, Swofford came across Baselane, which offers both. It’s an automated banking, bookkeeping, and rent collection tool that’s become an integral part of their workflow.
It’s the main AI tool they use — and the only one they pay for ($20 a month).
“All of our rent collecting happens there; they notify me if someone has not paid; I check all of our expenses through there; I do all of our categorization through there,” said Swofford, noting that they also pay their contractors through the platform and earn a good APY by keeping their business funds with Baselane.
They also use it to track property performance and analyze trends that may affect their strategy. For example, the financial reports generated by Baselane helped them realize that two-unit properties in their market weren’t as profitable as bigger multi-family properties. Now, they pass on duplexes and focus on acquiring properties that have three to 10 units.
2. Asana. Swofford and Louw use the free version of the work management platform Asana to assign tasks to their contractors. They regularly work with contractors, as they use the BRRRR method — short for buy, rehab, rent, refinance, repeat — and are purchasing properties that they can add value to through renovations.
They can also assign maintenance tasks through Asana anytime a tenant submits a request.
3. ChatGPT. They use ChatGPT regularly to help with everything from crafting emails to problem-solving. For example, the chatbot was helpful when they had to navigate an eviction for the first time, and they’ve used it to answer questions about what the landlord is responsible for versus the tenant.
“That’s literally all we have. We pay 20 bucks a month for Baselane and everything else is free, as of right now,” said Swofford.
Ultimately, they want to leverage AI tools to be better landlords — to improve their response time to tenants and communicate efficiently and effectively.
Louw has learned that if you treat your tenants well, they’re more likely to take better care of the space: “When they see that you’re respecting them, they tend to be respectful back as well.”
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