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Exploring Life & Business with Sarah Biggerstaff of Upside Realty

Today we’d like to introduce you to Sarah Biggerstaff.

Hi Sarah, thanks for joining us today. We’d love for you to start by introducing yourself.
Back at the age of twenty three I was working as the assistant to a local entrepreneur, the Rainey Street Queen, Bridget Dunlap. What a unique and profound experience it was working closely with Bridget; I believe it must have been a greater power in the universe that brought us together. Bridget instilled in me not only her entrepreneurial spirit but her never-give-up and don’t-take-no-for-an-answer attitude, which is how she came to achieve what she has today. She always used to say “It’s a long way to the top if you wanna rock n’ roll” (from the AC/DC song). I can still hear her voice in my head as she frequently said that during her presentations and public speaking engagements.

While working for Bridget, I purchased my first home in Austin – a little two-bedroom bungalow that was rough around the edges but had lots of charm and potential. The house was a foreclosure and the process was complicated and stressful (it was a multiple-offer situation even back in 2012). Coming out of that experience, I began to envision myself helping other people to buy and sell homes and creating an overall positive experience for them during what can oftentimes be a stressful time in people’s lives. So I went for it! In 2013, I got licensed and jumped into the industry, which for me felt like jumping off a cliff into The Great Unknown. It’s true, though, as the saying goes “Jump and the net will appear”. I made my great leap, and so the net appeared.

My first broker, Lucian Morehead of Asterra Properties, instructed me to write out a business plan for what I hoped to accomplish in real estate which also included describing my ‘why’. Why am I doing this? What is it that motivates me to put forth this great effort in this newfound career and to achieve the goals in my business plan? I included several pictures which helped illustrate my ‘why’. My motivations were to gain financial freedom, have free time, take vacations, and most importantly to help my family – specifically my Mom, my brother, and my sister. You see, I came from a very poor family and upbringing, financially speaking. So for me this was the opportunity of a lifetime to make something for myself. My mom, who didn’t have much money of her own, gave me a thousand dollars in cash so that I could go out and buy myself some nice clothes to show houses in. I’ll never forget that. And so began my career in real estate. I’m very grateful that through my work as a Realtor I’ve been able to help my Mom and other family members substantially since then in more ways than one.

My motivation to help and support my family grew stronger and ultimately became my sense of purpose. Aside from representing real estate clients over the years, I also invested in the market myself, purchasing multiple properties along the way. I’m thankful and proud to say that my Mom and my brother now live in two of these properties. I’ve also been able to employ my sister through another business of mine – an app for the real estate industry which I created and launched several years ago, Homease.

In 2019, my long-time coworker, dear friend, and now business partner, Joanna Jennings, and I started our own real estate brokerage in Austin. This was something I never anticipated doing but life called… and we answered. We named it Upside Realty, where Joanna and I truly believe “The Sky’s the Limit”. We have a small team of amazing like-minded, professional agents whom we’re lucky enough to work with. I also have my own entrepreneurial projects that I work on in addition to being a Realtor and broker. It’s hard to believe how many years have already passed working in the world of real estate and yet I know the journey has only begun!

I’m sure you wouldn’t say it’s been obstacle free, but so far would you say the journey have been a fairly smooth road?
My career trajectory has been steady in the sense that I’ve always had an extraordinarily strong sense of determination, tenacity, and have worked hard since I was a child. Growing up I was painfully shy and struggled socially but working hard was my saving grace as it always came very naturally to me. I graduated from college at the age of twenty. Only sheer determination and hard work has led me to where I am today. I’ve never given up but forged ahead and simply figured it out as needed.

That being said, although working hard has come easy for me, the most significant struggle I’ve faced throughout my life has been that of my own self-doubt, insecurities, and ultimately a lack of self-acceptance. Because of this, I had a tendency to attract romantic partners who were emotionally unavailable or who didn’t treat me well. It seemed wildly incongruent that my career life was sailing along while my dating life seemed to be nothing short of a non-stop struggle. It was one dating experience in particular at the age of twenty nine that hurt me down to the very core of my being and forced me to finally awaken to realize my own self-worth. So at the age of thirty, in what was a drastic act of self-love, I walked down the aisle to speak out loud solemn vows and to marry no one other than myself in what I called “My Self-Wedding – Becoming a Biggerstaff.” For me this symbolized making a commitment to myself, to honor and love myself the same way that most people vow to honor and love their significant others.

Even today, I still struggle with sometimes being too harsh on myself, but I’ve grown tremendously in self-acceptance and continue to practice granting myself the same grace, patience, and love that I would extend to anyone else in my life. I sometimes go back to re-read my own wedding vows to remind me of my inner truth. It’s interesting to look back and reflect on the notion that my greatest struggle throughout the course of my life was actually my own self-worth.

We’ve been impressed with Upside Realty, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
My approach to whatever I do in life and whomever I connect with along the way has and will always be one that is purely from the depths of my own heart and from a place of integrity, compassion, and kindness. From the real estate clients I have worked with over the years to the businesses I’ve started to the people I’ve interacted with in even the smallest of ways, I like to believe that this essence about me reflects itself in all areas of my life. I have a heart of servitude and truly enjoy making other people happy. As the saying goes by Maya Angelou, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” I always try my best to make people feel like they matter and like they are important and appreciated because they do and they are.
Being an entrepreneur, I have several businesses in the real estate world that all work together to complement one another. Upside Realty is my brokerage through which I work with my personal real estate clients to buy and sell homes. Several years ago I also created an app called Homease, that connects local agents to a trusted network of contractors, inspectors, and other companies that we work with during real estate transactions. Homease is a play on words, since as Realtors we typically get recommendations from our ‘homies’- other agents we know and trust.

Most recently, I also created and launched a partner program to Homease and Upside Realty called Homease Heroes that serves eleven categories of local community Heroes to help them buy and sell homes while receiving savings and discounts at every step along the way in their journeys. All are my businesses and my babies!

Of everything I’ve worked on over the years, I am most proud and find a lot of personal meaning and value in my Homease Heroes program. I grew up in Austin, back when it was a much smaller and slower-paced town. I remember as a kid my Dad taking me to the spring kite festival at Zilker Park and there being a small handful of people there flying kites. Anyone who has been to the kite festival in recent years in Austin knows it’s now a huge event with thousands of people, food trucks, and festivities. Austin has become a different place in multiple ways, including the issue of finding affordable housing and buying real estate. I personally have close friends who are teachers, nurses, and other community Heroes; my heart goes out to them knowing that although they work in Austin and serve our community many of them can no longer afford to live here.

Homease Heroes serves teachers, healthcare workers, military, social, government and non-profit workers, just to name a few. Through our program, we offer commission rebates to our Heroes on both the buy and sell side of real estate transactions and have also partnered with local lenders and other businesses who offer our Heroes discounts on their home inspections, remodeling jobs, and more. Our average Hero receives about $2,500 in cash savings at closing from our program. Although I can’t control the fast pace of growth Austin is experiencing, Homease Heroes allows me to do my small part to give back to our Heroes who work hard every day to serve us and our community. I also specialize in representing seller clients to sell their homes for top dollar, and in working with first-time homebuyers to help them navigate what can be a very competitive and at times unpredictable market.

What does success mean to you?
My personal definition of success has changed drastically these past few years as I’ve grown into my thirties. Today I define success for myself as having autonomy (working for myself) in a fulfilling career that I enjoy but also having free time to spend with the most important people in my life, and to pursue other interests and hobbies I enjoy. In the past I defined success strictly in terms of my career and money over all other things; I was a workaholic for years to say the least. However, in recent years that definition rings hollow for me. Having precious time to do other things that bring joy into my daily life, like being outdoors, taking my dog, Nova, on walks or hikes, exercising, meditating, spending time with my family, and simply stopping to ‘smell the roses’ are all high on my priority list nowadays. Being able to live my life fully as myself, imperfections and all, and balancing all of these things, never perfectly, but in some type of harmony that feels congruent with my true self… That is the ultimate success I could ask for. It’s never perfect but it’s real and it’s meaningful.

Contact Info:

Image Credits
Community Impact Newspaper (photo of me showing a house to my clients)

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