Author: josh
Chicago is known for a lot of things: deep-dish pizza, famous architecture, and loyal sports fans. But there’s more to the city than its biggest claims to fame. It’s a place where neighborhoods each have their own personality, summers revolve around the lakefront, and residents have no shortage of restaurants, festivals, museums, and local traditions to enjoy year-round. Whether you’re browsing homes for sale in Chicago, considering a move, or are simply curious about what life is like in the Windy City, there’s no better source than the people who call it home. We asked Chicago locals to share what…
Buying just one rental every two years can make you financially free—and by a lot.So many real estate investing influencers constantly talk about buying dozens, even hundreds of rental units to live your dream life and become a millionaire. But, as someone who’s been consistently investing, doesn’t own dozens of properties, and has made millions from real estate, I thought I’d do the math.Today, I’m going to show you how buying just one rental property every two (or even three/four) years can turn you into a millionaire with over $16,000/month in cash flow. You don’t need to buy sketchy properties…
Do you have home equity sitting in your primary residence? You could use it to buy your first or next rental property! There are several ways to do this, and in today’s episode, we’re sharing them so you can make your money work harder!Welcome back to another Rookie Reply! Whether it’s a home equity line of credit (HELOC) or a cash-out refinance, there are multiple ways to access the equity in your home. But which option is best? Stay tuned and we’ll help you determine the right move for your situation.Next, if you’re preparing to open an Airbnb, the days…
A group of Amazon engineers spoke out against unfettered data center construction, calling out their own employer for pouring money into AI infrastructure while slashing headcount. The employees pointed out the hypocrisy between the company spending billions to build these infrastructure projects, all the while laying off thousands in anticipation of the AI agents these data centers would power to replace them. “It’s been reported that this year, Amazon is spending $200 billion on capital, with most of it going to data centers and AI,” Patrick Schloesser, a software engineer at Amazon Web Services, said at a Seattle Land Use…
Dave:The engine that drives the US economy, the American consumer, is in trouble. New headlines are coming out daily showing the strain on the average American citizen, but it’s not just headlines. It’s not just fear-mongering. The strain Americans feel is real. It’s starting to show in the data and it’s even starting to change real estate investor behavior. All of this is unlikely to just be a blip. These are long coming trends that are going to impact the economy, they’ll impact our businesses and are investing for the foreseeable future. So today on On the Market, I’m sharing…
Just when you thought the dust had settled on the return-to-office wars, one startup founder has reignited the debate—accusing remote workers of sneaking off and doing life admin on company dime for a third of their working day. Serial founder Bridger Pennington panned his camera around an office full of people still at their desks on a Friday evening to prove his point that in-office working is more productive. “I get a lot of hate, but I’m a big believer for working in an office in person,” Pennington posted to his Threads account, where it’s racking up thousands of reactions.…
The housing market is shifting. Existing-home sales remain sluggish, competition is intense, and buyers’ expectations are evolving. Yet while some agents are struggling, others are finding new opportunities in emerging niches, changing consumer preferences, build-to-rent communities, luxury markets, mixed-use developments, and office-to-residential conversions. Join us for a discussion on where buyer demand is heading, what […]
Connecticut joined a growing list of states restricting pocket listings after Gov. Ned Lamont signed SB 340 on May 27. The law requires residential listings to be publicly accessible the moment any marketing begins, with penalties of up to $5,000 or license suspension for violations.
In This Article Name Ben Chester Location New York City Occupation Tech sales and real estate investor Assets Eight properties, three short-term rentals (including Billy Joel’s former Hudson River estate) Investment strategy Short-term rentals and house hacking Financing Conventional loans In 2012, Ben Chester was making $30,000 a year in New York City, spending every dollar on rent. Frustrated, he decided to secretly move into the sleep clinic where he worked, subletting his apartment on Craigslist to cover the lease. That hustle eventually turned into a furnished-rental business that attracted venture capital, grew quickly, and then collapsed, leaving Ben with…
In This Article Mortgage rates are now over 6.5%, the highest level since the Iran war began. For anyone who planned to make 2026 the year they started or accelerated their real estate investing career, that’s some sobering news. However, people are still investing and doing deals now, which will pay off in the future. Understanding the Rate Environment It might not be much consolation to state that today’s high rates were largely self-inflicted. Inflation tied to geopolitical concerns has pushed Treasury yields to multiyear highs. It’s a significant reversal from February 2026, when rates briefly dipped below 6% for…