How to Invest in Real Estate WHILE in College (It’s Possible!)

What if college were the best time to build a rental portfolio?

Daniel Kaplan began his real estate path with something that sounds more like a garage startup than a textbook strategy: $20,000, a laptop, a stubborn curiosity, and a friend who sent a single video about Section 8 housing. The result was not an overnight miracle. It was methodical, messy, and stubborn—exactly the kind of story that changes how you think about starting young.

From sneaker flips to rental cash flow

I love the bluntness of Daniel's origin story. He made money flipping sneakers in high school, then pivoted to a bigger ambition when a buddy suggested Section 8 investments. Rather than chasing glamour markets, he and his partner did what most people skip: they looked for a market that matched their capital. They picked Birmingham, Alabama, because it met a cold, practical test—cheap acquisition costs, strong voucher demand, and tolerable property taxes.

The first move felt audacious. Two college kids, living in a frat house, buying property sight unseen across the country. Yet there was method beneath the bravado: a buy box (three bedrooms, rehab under $10k, under 1,500 square feet), a weekly spreadsheet from a trusted local agent, and a disciplined process of underwriting until the odds shifted in their favor.

Reps beat luck: the power of volume

Here's what stood out the most: they reviewed roughly 80–100 deals before pulling the trigger. That volume turned an hour-long underwriting exercise into a two-minute gut check. I honestly didn’t expect that kind of grind from college investors. It's tempting to romanticize one great find; the truth is they treated deal sourcing like any other skill—you get better by doing it relentlessly.

Section 8 helped simplify part of the math. The Housing Authority published voucher amounts, which reduced some uncertainty around rent. But that certainty was only partial. Daniel cautioned that the Housing Authority’s listed maximum often isn’t what gets approved, and approval timelines can stretch to months. This was a wake-up call: guaranteed rent isn’t the same as guaranteed cash flow on your timeline.

Build a team you can trust—then stress-test the numbers

Trust was the grease that made a remote acquisition possible. Amanda, a local agent, turned a cold relationship into the firm foundation the students needed. They FaceTimed walkthroughs, leaned on her referrals for contractors and property managers, and accepted that early mistakes were inevitable so long as the deal had margin for error.

That margin is central. Daniel’s approach: underwrite conservatively. In these class C markets, he assumes 40–45% of gross rent goes to operating expenses. His shorthand? Rent times 0.6, minus mortgage equals bottom-line cash flow. It’s a blunt tool, but it forces realism—especially important when you factor long vacancy windows for voucher tenants.

Section 8: both blessing and bottleneck

Don’t buy the headline that Section 8 guarantees effortless income. Daniel’s first property took a month to close and two months to lease—fast by today’s standards. Now, he advises planning for four to six months of vacancy and knocking 10% off the Housing Authority figure. Those adjustments separate a promising case study from a house that becomes a liability.

When the numbers still work after these conservative tweaks, the deal is resilient. When they don’t, the lesson is simple: walk away. That kind of discipline is rarer—and far more valuable—than luck.

Fuel growth with active income

One of the most pragmatic moves in the story: after the first deal, Daniel needed capital and started wholesaling. It took six months of brutal grind to earn his first check, but the skills he built—finding, vetting, and moving deals—became the engine that funded future purchases. If you want a portfolio, you’ll need some active income to bridge the gap between ambition and acquisition.

He scaled to nearly 100 units across Alabama, Wisconsin, and Texas by repeating the playbook: pick markets that fit current capital, build a local team, underwrite conservatively, and accumulate experience through sheer volume.

Three practical rules that stuck with me

• Underwrite for reality: use rent * 0.6 minus mortgage to model conservative cash flow.
• Assume delays: budget four to six months for Section 8 lease-ups and cut listed rents by about 10%.
• Repeat the reps: treat deal analysis like a craft; speed and judgement come from volume.

What really caught my attention was how Daniel turned constraints into leverage. Being young meant less capital, but also fewer obligations and more runway to make mistakes. He chose activities that taught transferable skills—underwriting, cold calling, team-building—while creating the revenue to keep investing.

There’s a tension throughout his story: audacious risk balanced by conservative math. That balance made the whole thing believable. It’s a reminder that early advantage isn't a sprint; it’s a sequence of deliberate choices that compound into something real.

At a time when many self-help narratives promise passive riches, this story feels refreshing because it is honest: success required cold calls, late nights, and an appetite for rejection. That kind of work is less glamorous, but it's the only kind that reliably compounds.

The reflective thought I’m left with: starting early buys you time, but time only turns into advantage if you pair it with disciplined assumptions and a willingness to do the hard, repetitive work others avoid.