Day: October 24, 2025

• 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.”

• Ring founder Jamie Siminoff said the AWS outage was a “tough day” for the home security company.
• “I would like to think we did the best for our customers that we can through that,” Siminoff told Business Insider.
• During the AWS outage, Ring customers posted online that they couldn’t see out their security cameras or disarm alarms.

The Amazon Web Services outage on Monday took down dozens of websites and online services. Ring was among them.

In an interview with Business Insider, Ring founder Jamie Siminoff described the day’s difficulties.

“Certainly it was a tough day,” Siminoff said. “You never want to disappoint customers. We call our customers neighbors.”

Siminoff said that he tried hard to be there for Ring customers: “My email’s on every box that we send out. I’m very out there,” he said.

Ring isn’t just a doorbell; it’s a home security system, which may have heightened customers’ concerns and the online backlash. “It’s like the beginning of a modern scary movie,” one X user posted. “I hope no one gets robbed right now,” another posted.

Amazon acquired Ring in 2018 for over $1 billion. Siminoff briefly left the company in 2023, before returning in April 2025. His new title is VP of product for Amazon, where he oversees related home security products: Ring, Amazon’s Blink security cameras, Key in-home delivery service, and the Sidewalk wireless network.

AWS is another subsidiary of Amazon. Siminoff pointed out his connection to the company.

“If you look at the history of AWS, I’d say it’s pretty stellar, but I guess shit does happen, as the bumper sticker says,” Siminoff said.

The AWS outage affected a variety of Amazon businesses. Some shoppers were unable to order from Amazon’s digital storefront. Others were woken up by rogue Alexa alarms.

The outage also affected non-Amazon businesses that run on AWS cloud services. Some users couldn’t mobile order their Starbucks or access their Robinhood accounts. Others worried about losing their Wordle streaks.

The outage has since been resolved, and AWS services are operating normally. The issue appears to have originated from a Domain Name System error at AWS’s Northern Virginia data center

Since Siminoff has come back to the company, he’s brought Ring back to its crime-fighting roots. Ring’s security focus left some worried during the outage: customers posted online that they couldn’t disarm their alarms or receive detection notifications.

“We got through it,” said Siminoff, who is promoting his new book, “Ding Dong.” “I would like to think we did the best for our customers that we can through that, both Amazon as a whole, as well as Ring as a division.”

“I’ve just got to keep trucking along,” he said.

• Some US defense companies like Anduril are working on more affordable missiles made at scale.
• Company leaders believe the approach helps solve problems with US munitions stockpiles.
• Should the US and China go to war, the US would need deeper magazines to keep up with a drawn-out conflict.

Warning signs are flashing, cautioning that a high-intensity war with China could swiftly burn through US missile stockpiles, leaving it hamstrung in a drawn-out conflict.

War games have, for instance, shown that in a heated fight over Taiwan, American forces could run out of long-range, precision-guided munitions in less than a week. Replacing those in the middle of a fight could stress both US industries and budgets. Trying to expand the arsenal ahead of a war might do the same.

To fix this problem, some defense firms are shifting toward cheaper, easier-to-produce weapons, breaking away from the Pentagon’s preference for the costly, high-end systems.

In a new Cogs of War podcast, industry leaders from defense firms Anduril, Mach Industries, and Castilian talked with War on the Rocks founder Ryan Evans about how their companies are working on cheaper missiles that can be quickly made in larger quantities for far less money than some other munitions.

“Everybody’s been hearing, kind of across the services, about this affordable mass problem,” Steve Milano, senior director of advanced effects at Anduril, said, “and we’ve got the exquisite weapons systems, but we really need affordable, sufficient mass” in missiles and munitions.

Last year, Anduril unveiled the Barracuda family of cruise missiles with different increments depending on size, range, and payload. On the podcast, Milano said Anduril was opening its first production facility for Barracuda in January 2026. “We’ll be pumping out 2,000 units a shift at that facility alone,” he said.

Anduril has called Barracuda “software-defined” and capable of being upgraded based on enemy countermeasures. The company also has said the drone also addresses a key US vulnerability, the possibility that precision-guided munitions that “would be exhausted in a matter of days in a high-end fight.”

When Anduril announced Barracuda, it said that the US defense industrial base and arsenal struggle with limited production capacity and little flexibility for upgrades because of complicated missile designs with bespoke parts and specialized supply chains.

Castelion’s CEO Sean Pitt said on the podcast that his company noticed the same problems and thus pursued affordable hypersonic missiles. It’s been raising funding and testing its Blackbeard missile for years, with plans to field it in 2027.

US Army budget documents identified Blackbeard as a launched effect for High Mobility Artillery Rocket Systems and suggested the missile could be useful as a way to hit time-sensitive targets at a reduced cost-per-missile compared to other weapons in the service’s inventory.

And Mach Industries won an Army contract earlier this year with its Viper vertical takeoff strategic strike cruise missile that costs less than $100,000 to manufacture at scale. CEO Ethan Thornton said on the podcast that the two big optimizations the company pursued were asymmetry, having low-cost munitions with ranges that can be produced en masse, and survivability.

All three companies are effectively looking to disrupt the traditional costs and supply chains of American missiles with goals of not only making systems cheaper in larger quantities but also with less intricate designs that can slow down production or upgrade cycles. But that doesn’t mean these companies are necessarily always competing with defense primes, larger American defense companies that have decades of weapons production experience and deep, established relationships with DoD.

There is certainly some antagonism in this space, perhaps exacerbated as some military leaders push for shake-ups. “They view us as a threat in a lot of ways, and we view them as kind of a threat in a different way, in that they can pollute your culture, they can slow you down a little bit,” Milano said of the big players.

But “the primes are necessary,” he said, and other companies “are a compliment to” them, not a replacement.

On the podcast, the industry leaders said that the way the Pentagon has traditionally bought missiles has been a long process with many requirements that result in yearslong development cycles with significantly higher costs.

The Anduril, Mach Industries, and Castelion approaches are part of a larger shift among some American defense companies toward a disruptive Silicon Valley-like model of moving quickly on designs, breaking and fixing things, and upgrading as needed, something services like the Army have also been embracing more and more with emerging technology linked to new software, artificial intelligence, autonomy, and drone systems.

That’s now spreading to missile development as the DoD and others increasingly recognize that having massive stockpiles of varied munitions that can be made affordably at scale are potentially more important to readiness for a peer-level fight than a limited arsenal of exquisite systems.

Recent conflicts in the Middle East have shown just how quickly combat can stress American missile arsenals. Shooting down Houthi missiles and shielding Israel from Iranian weapons came at tremendous cost in THAAD, SM-2, SM-3, and SM-6 interceptor expenditures. The Ukraine war has drawn heavily on Patriot interceptor stocks, and there are concerns about Tomahawk cruise missile stockpiles.

Last fall, Adm. Samuel Paparo, the head of US Indo-Pacific Command, said conflicts around the world had eaten into stocks of some air-to-air missiles, which were crucial for the region he oversees. “It imposes costs on the readiness of America to respond in the Indo-Pacific region, which is the most stressing theater for the quantity and quality of munitions, because [China] is the most capable potential adversary in the world,” he said.