Jeff Allen has had exactly two jobs in his life. He started picking strawberries on a farm in fifth grade, worked through college, and next month will mark 30 years at the same engineering company. Somewhere along the way, he also became a real estate investor — starting with one house behind his own property and working up to a 52-unit apartment complex, commercial mixed-use buildings, and a portfolio of syndications spread across the country.
He did all of it while keeping his full-time W-2 job. Here’s what he told us about how he got started, and what he’d tell someone standing where he was in 2020.
Take Action, Even Without All the Answers
Jeff’s entry point was a familiar one: a friend doing real estate, a copy of Rich Dad Poor Dad, and a lot of podcasts and books. As an engineer, he admits he’s wired to over-analyze.
“I was wondering, am I doing any analysis paralysis as an engineer? I’m very analytical, and the steps are details,” he said.
The pandemic forced the decision. In 2020, with the market quiet and competition thin, he bought his first rental: no contingencies, an escalation clause, and, in his words, a “bunt single” of a deal that turned into “a stolen second base, and now a stolen third base.”
His advice to anyone hesitating: “The first thing I would say is take action. Now, that is easy to say — it’s hard to do. Where do I start? Do I need an LLC? There’s always going to be questions. Don’t allow that to hinder you. Seek out a mentor, read some books, listen to podcasts — but take action.”
Start Small So Your Mistakes Are Small
That first property gave Jeff the confidence to go bigger, a lot bigger. His next deal, with two partners he met through church, was a 52-unit apartment complex in Hummelstown. The deal nearly died twice: the original owner backed out days before closing, and then the pandemic shut everything down. Six to eight months later, the sellers came back around, and Jeff and his remaining partner raised capital from friends and family to close it.
Even so, he doesn’t recommend skipping straight to something that size. As a structural engineer, he thinks of it in terms he knows well.
“You’ve got to make sure the foundation’s good, because all the loads come through,” he said. “Start with something smaller, because if something happens, it’s a smaller mistake. You’ll learn from them, and they’re smaller at the beginning.”
Get Good Counsel Before the Big Decisions
The 52-unit sold roughly 15 months after purchase. It was bought for $3.4 million, sold for $5.5 million, with investors earning a 2.14x equity multiple. Along the way, Jeff negotiated a lender’s origination fee down by about $9,000 and avoided any prepayment penalty on the debt.
When it came time to sell, he leaned on mentors rather than guessing his way through the tax side. Instead of a 1031 exchange, which would have required a “drop and swap” given the multiple LLC members, he and his partner each made limited partner investments in other syndications and ran a cost segregation study to bring depreciation forward and offset the gains.
“It was the first time I realized — people will tell you taxes are a number one deterrent of wealth, and you can understand that from an outside perspective. But from living it, I’m like, wow, this is real.”
Know Your Market — and Stick With It
Jeff invests almost entirely in central Pennsylvania, and he’s not apologetic about it. He hears the pitch for Sunbelt markets often: bigger appreciation, more cash flow, faster growth. But he’s watched those same markets swing hard in both directions.
“Some of the Sunbelt areas went way up in price, and now they’ve come way down,” he said. “You contrast that with a lot of the Northeast. There’s much more consistency.”
He credits some of that stability to Harrisburg’s role as the state capital, which keeps the regional economy steady even when other markets spike and crash. “We’re basically at two to three percent every year, it seems like steady growth,” he said. It’s the tortoise-and-the-hare argument: slower, but consistent, and it comes with a practical advantage — he can drive to every property he owns.
Match the Investment to the Goal
Since selling the 52-unit, Jeff has spread capital across markets and asset types rather than concentrating it: a golf course and wedding venue, a mixed-use building in Hanover, another in Gettysburg, a car wash fund, a mobile home park fund, self storage, and industrial. Some are structured for preferred cash distributions now; others are longer-term holds built around an eventual cash-out refinance.
“I wanted the diversification between all those, so I wasn’t just, you know, all the capital in central PA or something like that,” he said.
Asked which of those investments has been the standout, he’s careful not to overclaim. Multifamily returns across the industry have lagged proforma projections in this cycle, he noted, while self storage and industrial have performed well and required less debt. His takeaway isn’t that one asset class beats another, but that investors need to know their own goals first. “Somebody could have a great W-2 job bringing in a lot, and it’s like, I don’t need it now, I want it for the future,” he said. “I need to hone in on what’s good for me, and then look in that direction.”
That same thinking shapes his growing preference for commercial tenants over residential ones. Businesses are easier to underwrite and less emotionally charged to manage than a family in an apartment they call home — what he jokingly calls avoiding the “toilets, tenants, and termites” of residential ownership.
Pass the Mindset On
Maybe the most memorable part of Jeff’s story isn’t a deal at all — it’s his daughter. During her senior year of homeschooling, she got curious about what her dad was doing and decided she wanted to buy her first property before turning 19. Jeff tailored her coursework that year toward the practical side of the business: insurance, square footage, flooring and repaint estimates.
Jeff co-signed the loan, but one detail made the biggest difference: he’d added her to a credit card years earlier, which meant she walked into her mortgage application with an 830 credit score.
“The broker’s like, I’ve never seen an 18-year-old have this great a credit,” Jeff said.
She bought a triplex, put in the sweat equity to fix up two vacant units, and has since taken over the day-to-day herself; Jeff mostly just helps with tenant conversations now. The entrepreneurial habit stuck beyond real estate, too: she later started her own cleaning business servicing short-term rentals. For Jeff, that’s the real payoff. “It flipped the switch in her for the entrepreneurial spirit,” he said — a lesson he thinks applies far beyond real estate, whatever field the next generation ends up in.
Why He Hasn’t Gone Full-Time… Yet
With 30 years at the same company, a portfolio spanning single-family homes to commercial mixed-use, and a business-owner daughter, it’s a fair question: why hasn’t Jeff walked away from his W-2?
“That creeps into your mind,” he admitted. Health insurance is the biggest open question, along with making sure he has enough built up before making the leap. For now, he says he genuinely likes his engineering work, and three weeks ago, he became a grandfather for the first time, which has him thinking more about time than about title. Going full-time, he says, is “definitely in the future,” just not a decision to rush.
The Bottom Line
Jeff sums up real estate investing simply: “It’s a get-rich-quick scheme. It only takes 10 years.”
What would take 40 years of W-2 work, he says, can happen in a fraction of the time if you’re willing to start small, get good counsel on the big decisions, and keep going.
If you’re looking to grow your real estate investments in Pennsylvania or Maryland, reach out to us at Clear Multifamily. We’re always happy to help.
