The Story of Tamara Simon (Koss Property Management)

Aug 31, 2023

American Dream Achieved

IBA, as an approximately fifty-year old business brokerage firm serving the entrepreneurial community of the Pacific Northwest, has been uniquely positioned since before the American Bicentennial celebration of 1976 to witness and hear the stories of thousands of people who have lived the American dream through entrepreneurship creating beloved businesses by employees, customers, and communities while finding personal fulfillment and financial prosperity through execution of their ideas, hard work, perseverance, and ability.  In an effort to share these stories heard throughout the years by our team of business brokers, who are commonly regarded as the “best listeners” in the M&A industry, IBA has retained highly regarded writer, Nesha Ruther, to tell their stories.  It is our goal to share one story a month. It is our hope that you will find the stories as inspirational and motivational as they are to us and the buyers who bought the businesses in IBA facilitated transactions in Washington, Oregon, and Alaska.

The Story of Tamara Simon (Koss Property Management)

By Nesha Ruther

Tamara Simon grew up in Chicago with her mother and two younger sisters. Her father left when she was young, leaving her mother a single mom with three kids under the age of five, and no means of support. The Simons ended up on welfare, and her mother took a part-time job as a crossing guard. “This was very unusual in our neighborhood. My sisters and I were the only kids who came from a divorced home,” she says. “It wasn’t as common as it is now.”

Tamara’s childhood deeply shaped her outlook on the world and her role in it as a young woman. “I watched my mother struggle financially, physically, and emotionally to raise kids on her own. I always got the message that you had to be able to take care of yourself, even if you got married, things might not work out. That was not the predominant message to young girls in the early 60s,” she explains. “I was bound and determined to go to college and get a job where I could support myself.”

Tamara’s family was Jewish, she wanted to be a Rabbi before learning it was not possible for girls at the time. With religious education out of the question, Tamara decided to become an attorney or the director of a social services agency. “I went to school and got my degree in political science. I did that through a combination of scholarships, a few loans, and working at McDonald’s.”

While going to college as a full-time student, Tamara also worked 20 hours a week as waitress. Despite significant hardship, she succeeded in her goal to graduate from college. “Looking back, it seems comical, but I was $5,000 in debt when I graduated, and to me, that was like a million dollars,” she says.

Tamara wanted to go to law school, but her financial situation was not ideal. Considering how much she valued being self-sufficient, she decided to work for a little while first and save up. She got a job with United Way and began working as their Assistant Program Director, for a new program being offered. It didn’t take long for the staff to realize what a talented employee she was. At 22 years old, she became the Program Director. “I would go and speak to a lot of for-profit businesses to raise support for our program. This included jobs for our clients and monetary support for United Way. I really enjoyed fundraising for the organization.”

Tamara continued to work for a few more years with United Way but realized that the pay was simply too low. If she wanted to be entirely self-sufficient, she couldn’t continue to work for social services agencies. “I was making $12,000 a year. The woman at the head of the division had a Ph.D. and 15 years of experience in the industry, and she was only making $18,000. I realized that 90% of the women who worked in social services had husbands with better-paying jobs.”

Tamara loved working for United Way but knew it would not allow her the degree of comfort and freedom she wanted. “Chicago is an amazing city,” she says. “But I hated the harsh winters.” After a visit to Seattle, she moved there in 1982.

“I still wasn’t ready to go to law school because I was trying to pay off the debt I had from my undergraduate. I read this book called What Color is Your Parachute? that talked about careers. It asked how dressed up you want to be for work, do you want to work inside or outside, and how much contact you want to have with people. I realized I love history, home tours, and helping people, I’m also good at sales, so I decided to go into real estate. But I was so impacted by my childhood and wanting a steady income that I decided to do property management because real estate sales go up and down.”

Tamara began pursuing her real estate license and cold-calling different companies asking for a position. To an outside observer, this may seem a departure from her original goal of working in social services, but Tamara doesn’t see it as such. “I like talking with people, I like helping people, and when you’re a salesperson, regardless of what field you’re in, your job is to have knowledge and share information, help people make the best possible decision to meet a need they have. That is what social services is too,” she says.

“What makes a great salesperson is knowing that the client always comes first. You find out what their needs truly are and you help them achieve that goal. Sometimes, quite frankly, that means you don’t get paid because their needs are not what you have at that moment. But my philosophy was always about helping the person, that is different view from a lot of people.”

Tamara had originally planned to go into commercial real estate, but in the 1980s, found it to be unwelcoming toward women. Instead, she got a job working in residential real estate at a property management company.

Tamara worked there for six years, learning the trade and managing single-family houses and small apartment buildings, which included anything under 20 units. She continued her education and got her designated broker’s license. “90% of women in real estate have a real estate license,” she says, “but they don’t go on to get the designated broker’s license, that’s why men own most of the businesses because you need to have that license to own your own company.”

Tamara also stood out in her skill at her job, and her ability to teach others. “The reason most people fail is that they have no training. I have a minor in education, so it’s easy for me to teach others.”

During this time, Tamara was able to pay off her student loans. “I decide, ‘Well if I’m going to go to law school it’s now or never,’” she says. She began preparing for the LSAT and taking courses in a paralegal program at Edmonds Community College, all while working full-time no less!

At the time Seattle was flush with lawyers, making it a highly competitive field. The cost of law school was also so high, that she would either have to accumulate massive debt or continue working through school. “I knew I was smart, but not smart enough to work and go to law school,” she says with a laugh.

Tamara met with her boss to consider increasing the amount she made on commission. He said something that would change the course of her career forever. “I wanted to go to a higher commission split, we were 50/50 and I wanted 60/40. He said these famous words, ‘No. I think you’ll find you’re well paid for a woman.’ That was all I needed to hear,” she says.

Tamara realized that if she continued to work for him, she would never get the acknowledgment or compensation she deserved. “I was single, and I had no kids. I was in my early 30s and my expenses were low. I thought, ‘Well I work on straight commission anyway. I know how good I am at this business; I’ll just open my own brokerage.’” That is exactly what she did.

Tamara had signed a non-compete clause, however. She had spent time and energy building strong relationships that she was unable to take with her. “I left with nothing and had to start all over again,” she says. “But again, I knew how good I was.” While this was undoubtedly anxiety-inducing for someone with such a strong need to be able to provide for herself, she had also learned the strength of her own abilities.

Tamara got to work forming her brokerage, which she called Koss Property Management. For the first two years, she would spend the entire morning making cold calls and going to real estate offices to make her case. “I would say, ‘I’m not here to compete with you. Yes, I have my broker’s license, but I promise I won’t be selling. What I’ll be doing is taking great care of your clients and their rental property so they’ll be able to buy more property from you. I guarantee that if your clients decide to sell, I will not solicit that. I cannot promise that they will go back to you, but I will recommend you.’”

Tamara’s pitch worked. Many real estate offices did not want to work with the owner to manage the property. Tamara filled that gap. “I built up a tremendous referral basis that way,” she says of her strategy.

When she wasn’t cold calling, Tamara got a job as a real estate paralegal in the afternoons. “I would rush downtown and work from 1:00 until 5:00 as a paralegal,” she says.

From 5:00-7:00, Tamara would show properties to prospective tenants or meet with prospective clients. When she got home in the evenings, she would do all the bookkeeping and marketing for her company. Every waking moment was spent working. “For the first two years from 8 in the morning to 10 at night I worked on the company, seven days a week,” she says.

On the weekends, Tamara worked as a nanny at popular hotels. “At these big fancy hotels downtown, people would ask the concierge, ‘We’re going out, I need a babysitter.’ Saturday and Sunday nights I worked at the hotel babysitting,” she says.

Tamara was wholeheartedly committed to running her business, often at the expense of other parts of her life. While entrepreneurship is universally challenging, it becomes uniquely difficult for women who are often also tasked with the responsibilities of child-rearing.

It was not lost on Tamara that many men run their own businesses while being supported through the early years by their wives, but this option is rarely given to women. “I wasn’t dating. I wasn’t married and had no children. For men, their wives can raise the kids or support them [financially]. The guy who started Starbucks, early on his wife was supporting him. It’s such a great story because it all worked out, but it generally doesn’t work that way for women,” she says.

After two years of total commitment, Tamara had brought in enough accounts to hire her first employee, who was responsible for bookkeeping and office management. She continued from there until she had a staff of four people working under her.

In addition to running her business, Tamara was able to develop a strong network in the community through her passion for education. “I loved teaching adults and I was really good at it,” she says. “I belonged to the Rental Housing Association in the Washington area, they didn’t have a good education program for private landlords, so I put together a course on my own called Landlords 101 and offered it to RHA.”

Developing these courses not only fostered her relationships in the community but required Tamara to stay up to date on the latest information and industry trends. “When you’re teaching something, you have to keep learning and stay at the top of your game,” she says.

Her courses were so popular, that at one point 50% of all her new clients came from classes that she’d taught. “People would ask me, ‘Why do you teach for free?’ Well for one, I wanted to give back to the industry, but it was also a great source of new clients.”

Tamara’s success was undoubtedly a product of tremendous skill and hard work, but also an unmatchable passion. “I loved it. I really was doing the work of an attorney, a social worker, and of course a teacher,” she says. For her, property management was all about problem solving and education.

“I was helping people who were trying to find ways of saving for their retirement. 90% of small landlords in this country are middle-class working people just trying to save for their retirement. They just don’t have the time or the wherewithal to manage it on their own.”

Tamara was deeply committed to helping all parties and made herself constantly available to tenants as well as landlords. She extended her vast knowledge and connections to tenants, connecting them with landlords she knew and helping ensure the properties were always maintained and cared for. She summed up the relationship perfectly in her company slogan; “At Koss Property Management we make it a pleasure to be a tenant and profitable to be a landlord,” she recites with a smile.

While real estate agents develop strong but relatively short relationships with clients, property management demands being in the lives of clients for the long haul. “When you are somebody’s real estate agent, it’s like dating. You go out, you see a lot of new things, you have lunch, and its tons of fun, and then the relationship ends. Property management is like a marriage; good, bad, and indifferent.” Talk about being married to the job!

Like any marriage, sometimes Tamara and her clients would disagree. “This is perhaps where I would differ from my colleagues,” she says. “There were times when my clients were totally in the wrong. I would have what I call “come to Jesus meetings” with them—which is funny because I’m Jewish—but for example, there is Landlord-Tenant Law, if the refrigerator isn’t working, you have 72 hours to fix it as the landlord.”

Sometimes clients would try to postpone bringing in maintenance, or they were unwilling to spend the money. Tamara ensured they did right by their tenants, not only for the tenants themselves but for the legal well-being of the landlord.

“I would have tons of discussions with my clients over security deposits. They would want me to charge the tenant, and I’d be like ‘No buddy’. If the tenant did some crazy things that would be one thing, but they can’t charge the tenant for normal wear and tear. I did a lot of education because my goal was always to see the landlord succeed.”

Tamara’s background in social work meant that more than anything else, she prioritized being an advocate for landlords, tenants, and others in the industry. She not only served on the board of the Rental Housing Association of WA state but the National Association of Residential Property Managers, Seattle chapter. She was constantly writing articles for local business publications to help provide resources and share education, as well as teaching classes to tenants and first-time residential investors.

“A lot of people think the landlord and the tenant have an adversarial relationship,” she says. “But I really believed in our mission statement. That we make it a pleasure to be a tenant and profitable to be a landlord. Those are not adversarial things, they can work quite well together,” she says.

Tamara’s business philosophy is an unfortunately uncommon one, unlikely to be found among other property managers. When asked if her gender has informed this philosophy, she answers with her usual panache. “Abso-friggin-lutely,” she says.

Tamara’s need to go above and beyond came from having her professional skills written off. “Men see me, and they discount me, women do it too,” she says. “Here comes this short zaftig girl (a Yiddish term meaning round & full-figured), and I can see it in their faces. But when I start talking, usually within a few minutes, you can watch their mouths drop,” she says with a smile.

While it is frustrating being underestimated, it’s even more satisfying to see others realize that they underestimated you. These experiences gave Tamara the confidence to be unapologetically herself, in both business and life.

“I was never going to make what I was worth working for somebody else,” she says. “I could see guys that were not as good as me getting hired by property management companies and making salaries plus commission. I applied for those jobs and I never got those offers. In one case, a company offered me a job but with $25,000 less than a guy with the same experience as me. That was a big incentive for me to have my own company. I wanted to get paid what I was worth.”

Like any small business owner is likely to tell you, the biggest challenge an entrepreneur encounters are not clients, but employees. “I think because I am a woman, employees felt they could talk to me about all their personal problems. It took me years to learn how to put a stop to that. It’s not that I don’t care, but I cannot solve problems with your boyfriend or ex-husband, it’s not my job. I don’t think [employees] would expect that with a male business owner.”

Tamara learned to enforce strict professional boundaries, but that did not mean that she didn’t look out for her staff. “I was committed to the idea that all my employees should have healthcare. That was almost unheard of in the industry at that time. It came out of my bottom line, but I felt it was important,” she says.

After decades of running a successful business, it was time for Tamara to work on her own retirement goals. She began quietly looking for a buyer for Koss Property Management. However, she found that many other business owners were not willing to pay what the business was worth, or otherwise were insisting on a claw back clause, which stipulates some of the money spent in the sale is returned to the buyer if clients leave during the transition. “I knew that most people who try to sell a house on their own get 20% less and a lot more aggravation. I realized that I needed a professional,” she says.

Tamara began meeting with brokers but was generally unimpressed. As a salesperson herself, she knew when someone was trying to get one over on her. “It was so discouraging. They would just come up with a random figure, it’s like telling somebody who’s got a house that’s worth $100,000 ‘I’ll get you $500,000.’”

That changed, however, when she found Gregory Kovsky and IBA. “The first thing Gregory did was tell me he needed P&L Statements, he needed this and that. It was like wow, really impressive after all the other brokers who made promises based off nothing,” she says. “He said to me, ‘If I’m going to represent somebody, I need to know these figures can be substantiated.’ None of the smarmy people ever said that.”

In Gregory, Tamara found a fellow professional, one who took her business as seriously as she did. “He put me through a lot of work to get a sense of my business, but everybody told me it would take a year [to sell the business] and he had meetings set up immediately. Gregory was unbelievably helpful, and I was impressed with the quality of [potential buyers] he brought to me. He really cares about his clients, and you can tell.”

Tamara sold Koss Property Management in 2018, she stayed on for a year working part-time to ease the transition and has since fully retired. While she continues to remain cautious due to COVID, she has begun leading zoom classes to further education among landlords, as well as doing the occasional bit of referral work. She is looking forward to beginning to travel again soon.

At the time of our interview, Tamara was a few weeks shy of her 68th birthday. “I love this industry,” she says. “I still cannot believe that as a young girl growing up in Chicago on welfare, I owned a business. To this day, I have friends who tell me how lucky I am. They made a lot more money than me, but they hated going to work. I couldn’t wait to get up in the morning.  I loved going to work and doing what I was doing, it was a Mitzvah,” Tamara says, referring to the Hebrew term for a good deed.

“To me, the American dream means that if you work hard, there are opportunities for you. The circumstances you are born into don’t have to be the circumstances that dictate the rest of your life. I lived the American dream because [my career] exceeded my wildest expectations, not just through money, but fulfillment too.”

A Mitzvah indeed.

Nesha Ruther is a writer and editor from Takoma Park, Maryland. She received her BA in English Creative Writing from the University of Wisconsin Madison, where she received a full tuition scholarship through the First Wave program based on academic and creative merits. She was a 2016 Young Arts winner in spoken word, a 2016 winner of the DC Commission of the Arts Larry Neal Writing Award, a 2017 winner of the Mochila Review Writing Award, which was judged by Nikki Giovanni, a 2020 winner of the University of Wisconsin’s Eudora Welty Fiction Thesis Award, and a 2022 Tin House Winter Workshop Participant. She has been commissioned to write and perform for the National Education Association, and has had work published in NarrativeNortheast, Angles Literary Magazine, Beltway Quarterly and more. She currently lives in Cincinnati Ohio and is the Lead Manuscript Developer at Holon Publishing and Collective Press.