Alright – so today we’ve got the honor of introducing you to Anna Papoutsakis. We think you’ll enjoy our conversation, we’ve shared it below.
Anna, thanks for joining us, excited to have you contributing your stories and insights. We’d love to hear how you think where to draw the line in terms of asking friends and family to support your business – what’s okay and what’s over the line?
Real estate is an amazing business with so much opportunity. Every personality under the sun, every background, every education level, etc, can succeed in real estate. The bar for entry is actually quite low compared to some other licensed services, so there is also a big misconception that the work is easy. More than selling properties, it is a relationship business, and the toughest part is lead generating at a high enough level that your pipeline is continually full.
There are so many ways to lead generate and convert new clients – cold calling, neighborhood farming, working open houses, etc. I personally have always been a real estate agent who relies on friends and family to support my business. I work my sphere of influence and the people I know. As I have grown, I have often been comically shameless in my pursuits.
Working with friends and family may be perceived as low-hanging fruit, but it is not for everyone. A high EQ is often necessary. For the most part, a residential real estate transaction can be an incredibly emotional experience with high financial stakes. Clients are dealing with ungodly sums of money to purchase or sell property – hundreds of thousands and even millions of dollars. The reasons and motivation behind the sale can be some of life’s happiest moments such as new beginnings, or they can be some of the darkest, such as death and financial despair. There are also many players and moving parts to juggle, such as lenders, attorneys, home inspectors, your counterparts on the other side of the transaction, etc. The process can get extremely contentious and in negotiations, no party is ever 100% satisfied. As an agent you’re steering the ship and keeping this transaction on course. With so many hazards to navigate, being able to check your own emotions and help close family members and friends can be difficult. It is high risk, high reward, but with the risk comes the potential to destroy a relationship.
I believe, from my experiences, to succeed with family and friends as clients, you must maintain a high level of professionalism and also be your authentic self. Ultimately, the person who hires you as their real estate professional must trust you, and the trust is a “little” easier when the relationship is pre-existing. Walking into a family member’s home with the goal of selling it cannot be taken for granted. You cannot walk in and assume you have the business. You have a foot in the door. Do the work. Your due diligence, preparation, and presentation must be consistent among all clients. Do not cut corners just because they know you and know you’re a good agent.
I was first licensed in 2016. My first few deals were actually with family and friends, including my parents, a childhood bestie, and some former work friends. As a Greek-American woman from northern New Jersey, I have a vastly large network of family friends with the same cultural background. Many of these contacts are highly successful and self-made individuals. This group was by far the hardest to break into, particularly my parents’ generations, consisting of Baby Boomers and The Silent Generation. My first opportunity came from a “cousin,” Leo Ioannidis, one of those close family friends who are more family than friend and it’s just easier to say cousin than explain the relationship. I heard from my mom, who is besties with his mom, that he was going to be relocating from New Jersey to Virginia. I called Leo and shamelessly shared where I received my intel. Hence, the Greek Mom Network, one of my greatest sources of business, was born.
Anna, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
Greek girl from Jersey is the simplest way I can describe my background. I am a first-generation Greek American born to immigrant parents. I was raised in Waldwick, New Jersey. No, we do not own a diner. My parents had a unique leather goods business, specializing in exotic leathers such as ostrich and elephant, but with a particular focus in alligator. They were wholesalers who produced extremely high quality pieces for luxury designers including Bijan, Lana Marks, and Trafalgar. My father was a third-generation craftsman – highly skilled and highly detailed, and often a tortured artist. My mother was the operator. My father was a feminist and my mother was always pro-education. They instilled in my sister and I an incredibly strong work ethic and discipline, and a ton of self-reliance. My father was quite charming and good with people, a natural salesman. My mother balanced him. She came off shy to new people, but had strong instincts and was excellent at discerning true intentions to make good business decisions. I was fortunate to have inherited my father’s charisma and ability to put people at ease while also maintaining discernment like my mother.
Growing up I loved cooking and hospitality. I had many interests, from school sports to my cultural heritage, art, writing,
and travel. I went to Johnson and Wales for undergrad and worked several years as both a banquet chef and waitstaff for a large off premise catering company, Fine Catering by Russell Morin. I left Rhode Island and moved back to New Jersey to pursue a Masters Degree in English and Writing. I had aspirations to be a food writer. I was able to intern at Saveur Magazine and even had a super brief stint at the Food Network. During this time I also worked part time at Starbucks for health benefits. When the market crashed in 2008 and publications like Gourmet Magazine went under, practicality took over and I sold my soul to middle management, moving up through Starbucks and later had stints at Whole Foods Market and Sur La Table.
During my time at Whole Foods and Sur La Table I was deeply miserable and unfulfilled. Working through some of my issues in therapy, I realized my skill set was more business and entrepreneurial. I did not belong in a particular box and I needed to be my own boss. During my time at Sur La Table was when I realized I could sell. Having bought my first home a few years earlier, a light bulb went off. Why sell pots and pans and high end espresso makers when I could be selling houses? I asked a few friends if they could see me in real estate and it was all a resounding, “YES!”
The first few years in real estate were difficult. I did not have the right mentor or brokerage brand behind me in the beginning, not for what I needed at that time. I also was dual career in the beginning in order to pay my mortgage. I was (and technically still am) a Brand Ambassador at Scanpan USA, performing product demonstrations on their cookware and partner company products, Global knives. It was a great gig that allowed me to get in front of people and really some free lead generation, which my amazing manager, Emily Wann, supported. During this time there were many moments of “I need to go back to a regular job,” or “Maybe this is not for me.” There were also haters who told me I would not succeed and to give up. In the early months a colleague advised I get a coach, citing everyone needs coaching. After researching programs, I ended up at Tim and Julie Harris for about a year and got many valuable lessons. I also discovered their background was at Keller Williams and many of their teachings were adopted from their models. Between being recruited by an old team leader and talking to a very good friend from college, Dick Buchanan, who was with Keller in Seattle, I made the switch to Keller Williams in 2017 and have not looked back.
I kept at it. One deal a year turned into 4 deals. In 2019 I met my husband, Kevin Hill, at a real estate conference. He saw potential in me that I did not see in myself. I kept pushing, and my production later turned into a sustainable 10-15 deals. As a business owner, some years are better than others, but I know I have developed the right skills and relationships to stay in this crazy industry.
With my management background, I also knew I wanted leadership opportunities. I toyed with things like becoming a team leader or a broker. My passion ultimately lies in helping people. In 2022, I started coaching new agents at the market center. This grew into a more formal role as Director of Productivity. I balance my personal sales with coaching and helping my office thrive.
I am a full service real estate agent and offer hands-on white glove service. Truly whatever it takes to get the deal done, from installing a hand rail to pass a building inspection to talking you through managing a tough breakup as you move on to your next property. Equally left and right brained, I love statistics and analytics and I love creativity and design. With my clients I find we can talk about anything, from recipes and sports to politics and family dynamics. I love learning and my clients always have so much to teach me. Recognizing they have so many choices in who to work with, I often ask, a lot of people can do what I do, but who would you rather spend the next 3 months with?
What sets me apart from my peers is my innate ability to foster relationships, especially maintaining those relationships long after closing. I answer random questions years after the deal is done, and I am a connector. When I need something done outside my expertise, it’s always, “Who do we know?,” not “What company does this?” The smoothest deals are always the ones where I know all the players involved. 90% of what goes wrong in a deal comes from miscommunication or a lack of communication. So many problems can be solved with a quick phone call or a 2 minute belly-to-belly meeting.
Finally, I am highly competitive and driven. I am not driven by money, though I do love commission checks with a lot of zeroes. I fully recognize to many peers in my industry, 10-15 deals may not be mega-agent status, but I have no interest in being a multi-millionaire or billionaire. A yacht would be nice, but making it home to dinner with my husband, for me, is more about how I want to spend my time on this earth. Therefore, I am driven by problem solving and challenges. I am notorious for taking on deals others will not touch. Deals that likely take up too much of my time and keep me from new business, but I love the sense of accomplishment being the one who can bring it all together and make it happen. Oh, you have 3 open permits and are being sued by 7 different entities over this property? No problem! Let’s talk!
Can you share a story from your journey that illustrates your resilience?
About 9 years ago, my sister Eva and I had essentially back-to-back near-death experiences when a flight we were supposed to take from Athens to Newark had not one, but two emergency landings. Upon the first landing the ground crew assessed a problem that would not be resolved that day. We were put up in a hotel, ironically, the Chandris where our father used to stay a lot on trips in the 80s and 90s. In 2016 it hadn’t changed much since its heyday, if you know what I mean. Not knowing what was going to happen we were kind of stuck at the sad hotel with a couple hundred strangers all trying to figure out how to get home. On the second flight the plane had the same issue and we had to go back to Athens. Upon a very hard landing, we broke the plane. They kept us on until they could insure the plane was not going to be engulfed in flames. They sent us once more to the Hotel Chandris for the night while they flew in a brand new plane from Newark.
I remember reaching out to my boss at the time to let him know of this unfortunate experience and that I would not be returning to work as scheduled. I was toying with leaving retail as I had just gotten my real estate license, but I wanted to power through another six months to secure a bigger nest egg. I was completely miserable in my job and the nonchalant way in which he didn’t ask how I was and instead went into the logistics of taking sick or PTO time to make up the extra days solidified that it was time to take a leap of faith – I gave notice within a few weeks of returning from that trip. I guess I was a trend setter years before “The Great Resignation.” Anyway, I digress…
During what we called our “adult summer camp” experience at the Chandris, we met Mark Linenberg and his husband on the rooftop bar. We had such a great time with them and we have kept in touch with Mark over the years via Facebook. A couple of years or so after that life changing experience, Mark messaged me about a friend of his who was living pretty close to me in Rutherford, New Jersey and how we should meet. She was a little older than me, but he could tell we would have a lot in common. Marianne Hensel and I became Facebook friends soon after. Life, travel, and the pandemic all got in the way, so we never really got the opportunity to hang and really get to know each other.
Unbeknownst to me, Marianne had been following a bit of my real estate career via social media. When the opportunity for a new job came, I was the first person she thought of and called about the possibility of selling her house. Not going to lie, she was a tough interview, but I accepted the challenge and wanted to do right by her. She reminded me of my sister, tough as nails businesswoman who knew exactly what she wanted. I joked that I was training my whole life for this. During the listing appointment, not only did I want the gig, I was feeling a bit bummed out because I kind of just wanted to hang out with her – I saw exactly what Mark was talking about.
After speaking to some other agents for due diligence, she offered me the job and did not look back.
Another fun fact from that trip, we had attended Leo Ioannidis’s wedding, the “cousin” I had mentioned earlier who gave me my first big opportunity within the Greek community. From relationships I fostered on that fateful trip, I have closed about 8 different deals.
How did you build your audience on social media?
My experience with Marianne Hensel is the ideal example of how I built my audience on social media. I do not separate my personal and professional Instagram. Like it or hate it, it is all me. Food I am cooking, trips I am taking, real estate tips, sales accomplishments, adventures with my family, life as a stepmom, sports memes, life as a young Gen Xer/older Millennial.
Real estate is really a long game, and you have to keep connecting and putting yourself out there. With social media, you don’t always know who is watching and who is rooting for you to succeed. Keep going, keep sharing. Your client is going to be hiring you for your expertise, but they are also hiring you because they trust you. That trust is not built just from the deals you’ve closed, it’s the common interests and values you may share.
Contact Info:
- Website: https://annapapoutsakis.kw.com
- Instagram: @therealannapaps
- Facebook: https://facebook.com/therealannapaps
- Linkedin: https://linkedin.com/in/annapapoutsakis
- Twitter: @therealannapaps
