600 units and almost 20 flips: Here's how Ashley Wilson created a real-estate investment empire leveraging just 2 simple strategies

  • Ashley Wilson — the co-founder of Bar Down Investments and HouseItLook, and author of "The Only Woman in the Room" — found her way into the real-estate investment realm through an inherent distrust of the stock market.
  • Wilson tested a plethora of different strategies including short-term rentals, house hacking, and long-term rentals before starting a flipping business.
  • When Wilson and her father began to make piles of cash from flipping, she branched out into multifamily apartment investing. It remains her main focus today.
  • In total, Wilson has flipped close to 20 properties and oversees 600 units spread across Texas and Ohio.
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Ashley Wilson — the co-founder of Bar Down Investments and HouseItLook, and author of "The Only Woman in the Room" — was climbing her way up the corporate ladder before she found real-estate investing. Suitably enough, she served as the director of global project management for vaccine trials for GlaxoSmithKline.

"My husband and I, very early on in our careers, were doing quite well," she told Business Insider. "And we were fortunate to have retirement plans, so to each their own, but we're not huge believers in the stock market."

She continued: "So we were looking for alternative investments, and we looked at multiple different investment strategies, but what we really liked about real estate was that it was an asset-backed investment that had major tax advantages."

Although Wilson's interest was piqued, her transition from director to full-time real-estate investor didn't happen overnight. In fact, it took her about four years of investing before she was ready to kiss her traditional 9-5 goodbye.

When Wilson was just starting out, she examined a variety of different investment strategies. Short-term rentals, house hacks, and long-term rentals were all vetted before she began flipping properties with her father.

That proved to be a fruitful decision.

"The first year actually, we only flipped one house," she said in a previous interview on the "BiggerPockets" podcast. "Our gross profit was around $65,000. The second year, each of us, my father and myself, made over six-figures on the second year flipping only two houses."

From there, her investing snowballed. 

Although Wilson's main focus is now centered around multifamily apartment buildings — she oversees 600 units in Texas and Ohio — she hasn't given up the flipping business. As of today, she's completed almost 20 flips and has no plans of slowing down.

Here's how she did it.

2 simple strategies

Wilson was able to build a real-estate investment empire by leveraging house flipping — where she was making money hand over first — and multifamily apartment investing.

We'll look at each separately.

House flipping

When Wilson initially entered the real-estate investing arena, she started out by financing flips with her father, who was a general contractor. Remember, she didn't become a full-time investor until years into her venture, so her ability to sock some of her income into properties was unmitigated.

Still, her style of flipping differentiates from the norm. Wilson goes after high-price-point homes.

"So it's a different game," she said. "So we have less competition in this space because, obviously, most people who get into flipping — especially new people — they're not going to go after a price point on acquisition north of probably $100,000 to $200,000, where we're most of the time at minimum doubling that. We're coming in $400,000, $500,000 on acquisition. And then turning around and selling it close to a million, if not over a million."

When Wilson enters a potential acquisition, she tries to visualize the finished product. Where others see a long, drawn-out hassle, Wilson sees opportunity.

"All of the houses we do are six-figure renovations, so they are full gut rehabs and they can be three, four hundred thousand-dollar renovations, " she said. "They're not cosmetic in nature."

That means adding "modern conveniences," shifting layouts, and even rerouting plumbing are fair game. In fact, she'll do just about anything to a home as long as it doesn't infringe upon its original integrity.

With all of that to chew on, Wilson isn't willing to pull the trigger unless her return on investment, on both her time and her money, make sense. 

"So because we're doing larger homes, there's greater risks," she said. "There's greater risks to market shifts, and also money at risk because you have money out and you're paying interest on that money. Or maybe you're using your own money — that money is not being put to use on other ventures."

When it comes to selling, Wilson lets comparables do the talking. Generally speaking, her properties sell for a premium over recent sales due to her incessant focus on renovations. 

Multifamily apartment investing

Although many well-renowned investors often say that the MLS is a lousy place to look for multifamily apartment acquisitions, Wilson pulls about 80% of her deals from it.

"So multifamily is a completely different beast," she said. "And what's interesting about multifamily is there are market cycles."

She continued: "So we look at it at a granular level, we're looking at a specific asset type within a market."

In order to discern whether a specific market is worth her time, Wilson keeps a keen eye on available inventory, new inventory, unemployment, and diversity of job sectors. In doing so, she'll be able to garner a better understanding of the underlying market's investment viability. 

As far as a specific property is concerned, Wilson's focus centers around rent growth, operations, and cash flow per door. It allows her to pinpoint inefficiencies and get a better idea of where she can add value. At a minimum, she shoots for $150 per door of cashflow. 

What's more, instead of leveraging different properties to finance others — a common strategy that's utilized amongst real-estate investors — Wilson eschews excess leverage. Each of her properties is its own separate entity with its own financing, generally a bridge loan or more traditional government-backed financing. 

"So for multifamily, we're in it for the long haul. We have started to explore some ideas of potentially doing new development," she said. "So, looking into a crystal ball, I would foresee us staying with this within this asset class and building on the momentum we already have."

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