Dennis Wells Talks Cold Calling Investment Properties and Building a Business From Scratch With Ashlee Brooks

The LA Massage Therapist Who Fell in Love, Moved to the Great Lakes, and Built a Real Estate Business

Dennis Wells welcomed Ashlee Brooks of @Properties Michigan and Indiana to the podcast for a conversation about what it actually looks like to enter real estate without a local network, without decades of market experience, and without the name recognition that established agents in smaller communities carry. One year into full-time real estate Ashlee is making cold calls that other agents have given up on, converting a for-sale-by-owner she first contacted in April, and building a referral network one trusted relationship at a time.

Ashlee’s path to real estate is not a straight line. She spent nearly sixteen years as a massage therapist in Los Angeles working for herself, managing her own schedule, building client relationships directly. She ran Airbnbs to supplement her income and fund travel. She moved to the Great Lakes area in 2021, fell in love with the region, and started thinking about buying investment properties. Getting her real estate license seemed like a practical way to learn the industry and potentially save money on her own acquisitions. What she did not anticipate was how much she would genuinely enjoy the agent side of the business.

Before jumping into sales full-time she spent two and a half years working for a short-term rental property management company covering properties from Michigan City up to Saugatuck along the lake coast. That experience gave her deep knowledge of the second home and vacation rental market in an area she was not originally from and introduced her to a network of general contractors, plumbers, septic inspectors, and other trade professionals that now serve her clients when those needs arise.

The Entrepreneur Who Never Really Fit a Nine to Five

Dennis observes a consistent pattern across everything Ashlee has done. She has always been her own boss in one form or another. She confirms it with a bit of surprise, as if the realization lands clearly for the first time as she says it back. Massage therapy in LA was self-directed. Airbnbs were self-managed. The property management role gave her significant autonomy. Real estate is the natural continuation of a career built around entrepreneurial independence.

She is direct about the trade-off. The freedom is real and it is meaningful. But freedom does not excuse not doing the work. If you use the freedom as a reason not to execute you will not be able to afford the freedom for long. She also acknowledges being an overthinker who can spend hours diving deep into one thing at the expense of other things that also need to get done. Knowing when to pull back from the deep dive and move on is a skill she is actively developing.

Where Business Is Coming From in an Area She Is Not Originally From

Not having a local network built over a lifetime is a genuine challenge and Ashlee addresses it without pretending otherwise. Some business has come from relationships made during her time with the property management company. She has helped former renters from those properties find homes. Her team at Keegley North has been a meaningful source of support and opportunity.

The thing she is doing differently from most newer agents is cold calling for-sale-by-owners and she is direct that this is where she has found unexpected success. Most agents either do not try it or try it briefly and stop. Ashlee is still doing it and she has the results to show why. The day before the podcast she signed a listing contract with an eighty-year-old property owner she first called in April.

That seller had been in the home for sixty years. He had sold and done deals across the country and wanted to try selling it on his own. Ashlee called, introduced herself, said if there is anything she could do to help just let her know, and followed up without aggression over the following months. When he finally decided to bring in help she was the person he thought of. And he has investment properties he is ready to start letting go of which means this relationship has the potential to extend well beyond the single listing that started it.

Why Cold Calling Still Works in 2026

Ashlee’s response to the suggestion that cold calling does not work in 2026 is simple. The people saying that probably have not tried it. She has a signed listing contract that proves otherwise.

What she has found is that the community of people who are willing to do it is small which means the people who do it consistently stand out dramatically. Dennis captures this with a line Ashlee immediately responds to. The negative conversations are just the cover charge to get into the room. She has learned not to take rejections personally because the person on the other end is not rejecting her as a human being. They are declining the offer today. When they are ready the agent who followed up consistently and respectfully without pressure is the one they call.

She joined an online cold calling community run by someone named Alexis who she found on Instagram. She attended a free session expecting to pick up a few useful points and instead found a genuine community where agents from across the country share situations, break down calls together on weekly group sessions, and support each other through the parts of the job that feel isolating when you are doing them alone. For a newer agent in a smaller market who cannot always lean on her team that community has been one of the most valuable things she has invested in.

The Value She Brings That Experience Cannot Replicate

Ashlee has personal experience with investment properties and short-term rentals. She has navigated the operational and financial realities of owning and managing income property. That background gives her something to offer investor clients and second home buyers that many agents who have spent their careers only in primary residence transactions cannot match.

But when Dennis asks what clients respond to most the answer is not the investment expertise. It is that she listens and she cares and she does the work to find the right answer rather than giving the convenient one. She does not want clients to feel alone in a process that can be genuinely overwhelming. Either she has been through something similar herself or they will figure it out together. That partnership orientation is what she hears back most consistently from people she has worked with.

She is also honest that her network of trusted trade professionals is a significant part of the value she provides. When a septic issue comes up or a plumbing question arises she has people she met during her property management years who can answer those questions accurately and reliably. A realtor who has that network and knows when to use it is more valuable than one who has the market knowledge but no trusted referrals for the situations that come up after the offer is signed.

What She Wants Her Business to Look Like in Two Years

Her two-year goal is grounded and honest. She does not want to feel like she has to wonder where the next deal is coming from. She wants to be a trusted name in the community that people think of when real estate comes up. She wants to feel comfortable and confident without the anxiety of a newer agent still proving herself. She is not chasing top producer status or a specific production number. She wants to be busy, happy, and respected.

She also wants to add to her personal investment property portfolio because that has been part of the vision since before she got her license. Real estate as a profession and real estate as a wealth building vehicle have always been connected in her mind and she intends to pursue both.

Cooper the Neighborhood Mascot

Ashlee’s golden retriever-Great Pyrenees mix Cooper deserves mention because he is genuinely part of her business. At two years old he has become the mascot of their lakeside community, appearing on golf cart rides while neighbors shout his name, starring in social media content that generated twenty-five thousand views on a single video, and attracting a local photographer who approached Ashlee about a beach dog photo shoot. She is completely honest that Cooper has driven meaningful social media growth and she has no intention of pulling back on that strategy.

Dennis relates immediately. His golden retriever on a small lake with golf carts and neighbors who know the dog by name but not the owner is the same phenomenon. Golden retrievers are apparently reliable mayors of their communities regardless of geography.

How to Reach Ashlee Brooks

Connect with Ashlee Brooks at @Properties Michigan and Indiana for buying, selling, or investment property conversations in the Great Lakes northern Indiana and southern Michigan area. She serves the coast from Michigan City up through the southwestern Michigan region.

Dennis Wells works with buyers throughout the Gulf Coast Florida area on mortgage financing and welcomes connections with buyers and sellers wherever he can be a resource. Reach out to Dennis Wells to connect on the lending side of any transaction in his market.

Sources

IndianaAssociationofRealtors.com
MichiganRealtors.com
NAR.realtor
MortgageNewsDaily.com
Investopedia.com