Philadelphia brownstone apartment building
Ashley Wilson

Ashley Wilson has done a little bit of everything in her real estate career. It started with a house hack: Wilson and her husband, Kyle, rented out spare rooms in their home in Hershey, Pennsylvania. A few years later, Wilson launched home flipping business HouseItLook with Kyle and her father. Then she made the jump to investing in and repositioning large multifamily properties in Texas, Missouri and Ohio when she founded Bar Down Investments with Kyle. 

Wilson, who now lives in the Philadelphia area, is also the author of “The Only Woman in the Room,” a collection of essays by successful women in real estate. 

She spoke with Story by J.P. Morgan about running successful businesses with family and the importance of networking and building a brand as a real estate investor. 

Q: You’ve evolved your investing strategy and launched new businesses several times in your career. How do you know when it’s time to make a change?

A: I am always thinking of ideas and I am constantly trying to identify whether or not those ideas will align with my overall goal in life, which is to continually build things that will eventually create more wealth without compromising my time. Historically, I pivot when I feel that I have mastered the business I am building, and that is when I start to branch out to a new one. 

Q: You’ve worked with family in your home flipping business. How do you manage to keep both the business and family strong?

A: Working with family is not for everyone. It really depends on the business and the people. The ability to turn work on and off is challenging at times. I follow three best practices: 

  1. Ensure that you would work with this person even if they weren’t family. 
  2. Respect each other’s genius and give each other the autonomy to own their respective genius or expertise. 
  3. Don’t let work consume your entire relationship. Have dedicated time to keep your relationship outside of work intact. 

Q: What’s your strategy for finding properties that are a good fit for your goals?

A: Real estate is a relationship-based business and it’s becoming a brand awareness business, and we keep both in mind when looking for properties. 

Brokers vet buyers because sellers’ No. 1 priority is having certainty the deal will close. So if a broker has confidence that you, the buyer, will close on the property, they will advocate for you to the seller. The more credibility you build, the greater your chances are, and today that credibility is heavily tied to your brand awareness — for instance, your track record, whether you’re a key opinion leader, books you’ve published, etc. 

And it’s not just relationships with brokers that matter. You never know where you might get a deal. It could be direct from the seller, through your electrician, your banker or even a random person you meet at a coffee shop. This is not an ABC (always-be-closing) business, but an always-be-networking one!   

Q: What’s a mistake you’ve learned from?

A: One mistake I made was not vetting a partnership thoroughly. I assumed one partner was the boss, as they had the experience, net worth and connections. In reality they weren’t: Someone else, who did not have those strengths, had a dominant personality that allowed them to control every situation. 

I have since put a lot of safeguards in place to ensure that everyone we work with aligns with who we are and what we are trying to accomplish. One of these safeguards is making sure people pass the three Cs (capacity, character and commitment) test. You also want to make sure you’re aligned financially, including personal finances. When someone’s facing financial constraints, it can alter decision making. 

Q: Part of your work at Bar Down Investments is repositioning real estate. When you’re making capital improvements to properties, what’s something that almost always pays off?

A: The exterior is a better renovation investment than an interior if funds are short, because society is more concerned about appearances than what’s behind the curtain. 

Q: What about renovations or improvements that just aren’t worth it?

A: Something that is almost always not worth it is offering an amenity that doesn’t fit your residents’ needs, especially if you plan to charge them for it. Take trash valet service, where the service collects trash from residents’ doorsteps. Typically, only higher-end apartment owners see the value. 

Q: What’s your best tip for cutting operational costs?

A: The lowest-hanging fruit is moving everything to digital receipt. You can deliver documents to renters, vendors and business partners electronically rather than on paper — for instance, emailing a copy of a maintenance request rather than printing out a receipt. This cuts down your paper, ink and copier and printer costs. 

Looking for more ways to go digital? Learn how Story can help you manage rent payments online. 

Q: If you could give a younger version of yourself one piece of advice, what would it be?

A: Start today and leverage other people’s money, skills and time the smart way to build your dream. In other words, you can leverage a bank’s money or a private money lender. When it comes to skills, you can partner with someone who has a skill you don’t have, and vice versa, to build a business faster. And you may be able to leverage someone’s time if they want to learn from you and are willing to give their time in exchange. 


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