If you can’t be your #1 fan, who can?

Elyse Estrada

I was recently invited to speak at my alma mater, Brown University, to a group of undergraduate women pursuing business careers. I had no idea what I would talk about but I was hoping that whatever it would be would make an impact. I thought about the type of advice I would have loved to have heard when I was in their position – carefree, exploratory, optimistic about what awesomeness was awaiting me after college.

I don’t care about being the best,
I care about being fulfilled.

Then it hit me, I’ll talk about the motto I’ve lived by my whole life: “If you can’t be your #1 fan, who can?” It’s become a mantra for me that I have told myself over and over as early as in middle school when I was a shy, awkward tween trying to find my authentic voice at the San Diego School of Creative and Performing Arts. I’ve been giving myself the same advice since the early 90s so it felt natural to share this advice with the future generation of female leaders at Brown in the hopes that it resonated with some of them to think differently about their own journeys and help them shape their future narratives. But this advice isn’t just for young people just starting out in their careers, it’s a reminder that we are all incredibly talented and capable of doing whatever it is we truly believe we can do.

I was good at most things my whole life; I wasn’t the best at anything but I was good enough. Getting into Brown was the most traditionally successful thing I had accomplished but with an 1190 SAT score, the odds of that even happening were against me. Since graduation I’ve realized that if I want something badly enough and believe I can do it, then I can and I have and I will because I am my own biggest cheerleader. I don’t care about being the best, I care about being fulfilled.

Personal Fulfillment

The reality is that you will encounter many lane changes along your path to personal fulfillment. The key is to understand how to navigate those lane changes while remaining true to your authentic self. Since it’s Women’s History Month, allow me to reflect my two biggest influences: my grandmother and my mother.

One day my grandmother was walking home from 8th grade. She had such a load of books that a boy helped her carry them home. Her mother was watching their interactions from the window and when my grandmother walked in the house, she was told that would be her last day at school forever. She would have nothing but the books she (and he) carried home that day. But that didn’t stop her from learning. She studied on her own, got a job at a large department store and worked her way up to become the secretary to the store manager as well as a top selling Avon lady in Tucson, Arizona. Like DNA, resourcefulness and resilience are maternal genes I’ve inherited.

It’s not about winning and losing, it’s about winning and learning.

My mother loved to read and study and got straight A’s her whole life. During senior year of high school, a guidance counselor asked her what her plans were for after graduation. My mom was planning on going to beauty school to get a job as a hairstylist and support her mother and siblings. That counselor sent her home with financial aid pamphlets for the University of Arizona. No one had ever talked to her about going to college but being her mother’s daughter, she would figure out a way to make it happen. My mother’s passion for learning took her down the path of becoming an elementary school principal. She went on to accept an award from President George Bush Sr. for excellence in education and fighting the war on drugs that was happening in her school community.

As these two women have taught me, paths aren’t predetermined or black and white. Life and career is not just about winning and losing, it’s about winning and learning. Sometimes you just have to go for it and see what happens.

Career Journey

My career has spanned across 17 years at only three companies. I’m what most consider a “lifer” staying at jobs for longer than four years at a time. But I’m comfortable in four-year increments. Elementary school, middle school, high school and college were all four incredibly different periods of my life and I was a different person in each of those periods. I treated my career the same way.

I got my first job because my older sister, Lydia Estrada, an advertising agency executive, sent my resume to a large media company and I was hired as an assistant digital media planner. I had no idea what digital media planning was nor did I understand a lot of the terms so I felt totally lost. But I’m an academic with a liberal arts background. I need to understand the bigger picture in everything I do. I took the time to play around and explore this new world of digital advertising. I was constantly asking my boss questions like, what is the overall media plan? Who is the consumer? Are we building the right strategy? Does the creative speak to them? I was the lead on the Hasbro toys account so I would literally play with the toys to get myself into the customer’s mindset. I had a million reps calling to pitch me day in and day out and I took all of those meetings. Many of those reps are still in my close network today because I was kind and respectful. One of those reps ended up hiring me eight years later. So be kind always, and never burn bridges. You never know who you might need to lean on later in life.

During that time at the media agency, I was also working on the H&M account where I taught my clients everything about digital. In my first meeting with the head of marketing, I learned how he got his job. He was at the agency when H&M opened their first US store, and when they needed someone at HQ, he was their first call. I was determined to prove myself and be their next call if ever they had an opening. Despite working on various other clients at the agency, my H&M clients believed I was 100% dedicated to their business because of the way I responded right away and was always on top of my work for them. When one of my clients relocated to Stockholm, Sweden to become the Global Head of Digital Media, his boss asked me who I knew that could replace him in New York. It was the first of many times I would say, “Why not me?” I spent the next 4+ years in my dream job. I created their first ever ecommerce site for a specialty collection in partnership with the NBC show “Fashion Star”, put David Beckham in boxer briefs into a Super Bowl commercial, orchestrated and dressed 50 tweens in an H&M kids fashion flash mob and learned that I thrived with creative ideation but also had the operational and organization skills to execute.

Despite it being my dream job, at some point I stopped learning and also wanted to make a bigger impact.

Despite it being my dream job, at some point I stopped learning and also wanted to make a bigger impact. That sales rep I mentioned meeting early in my agency days was now Foursquare’s new President, Steven Rosenblatt, and came in to pitch me on H&M being a beta tester for their first advertising product, which was like search for the real world. During that meeting, my eyes lit up and I started nerding out saying things like “you can tell me where my customers go before and after they visit H&M, you can tell me what other types of stores they shop at or places they like to go when they aren’t shopping”. He laughed and said “You totally get it, we’re hiring if you know anyone like you.” For the second time in my career, I gave him the “Why not me?” response.

Steven hired me as the first Account Manager on the sales team. He had not yet hired any sellers but he had sold a handful of pilots to huge brands and needed someone senior to manage the accounts. I was exhilarated and terrified at the same time but Steven believed I could do it and I knew I was ready for a new challenge so I jumped in headfirst. I had zero sales, tech or start-up experience and yet, in my position, I was responsible for growing Foursquare’s first-ever advertising revenue, building out the team, designing scalable processes, segmenting clients for acquisition and retention strategies, and a whole bunch of other firsts for me and the company. I spent six years hiring and developing incredible talent and helping our clients understand the power of location intelligence. Our business evolved tremendously across those six years, going from native advertising in our consumer apps to personalized, programmatic advertising that could be tied back to in-store visits. I learned a tremendous amount about the technology, the competition, and how to effectively scale a sales organization.

When Steven left to launch his own company, a new CRO was hired and change was imminent. She wanted to hire someone above me with more sales experience, someone I could learn from and expand my skills in client success. To be honest, I was done learning the client success world and wanted to tackle something else. She mentioned needing a sales enablement and training role at Foursquare, someone who could take all the product knowledge and client success perspective and train the team when new product features launched. I looked at her and once again said “Why not me?” I had no idea what sales enablement was, nor had I worked somewhere with that function, but I embraced the fear of the unknown. I used it as motivation and spent two months researching best practices and having meetings with other sales enablement professionals to learn how other companies were doing it. Then I could adapt it to Foursquare’s needs.

In the middle of my research phase was the Annual Foursquare Talent Show. I had participated in the Talent Show every year in the past, either with Fourschoir (our a cappella group) or performing with 2-3 others. I was so inspired by the courage that others had to perform a solo so naturally, I thought “Why not me?” and signed up for a solo. I had sung in the past, that wasn’t a surprise. I wanted to surprise my colleagues by doing something new. I wanted to play an instrument and sing at the same time. I thought that if I was going to be in a new role responsible for teaching other people, that I had to put myself back into the student mindset. “A Star Is Born” had just come out so I decided to learn the keyboard for Lady Gaga’s song “Always Remember Us This Way”. My teammate, PK, lent me his keyboard. I was now accountable to him to make good use of his generosity. Six weeks of YouTube tutorials later, I got on that Foursquare stage. Before the show I was telling PK that I was nervous. He said “just go up there and rock it, only you will know if you mess up”. That advice was everything and is also true of most situations. Be confident, have fun and do your best. That moment on stage was such a high point that I hadn’t felt in a very long time. It felt so good because I was truly my authentic self. I had set a time-based goal, had an accountability partner who would be proud that I did what I said I would, got up the courage to get on stage in front of hundreds of my peers and just rocked it out. I did start to mess up the keys towards the very end so instead of freezing, I pulled an Elton John and slid my hand across the whole keyboard, grabbed the mic and belted out the rest of the song. In that moment, I was my #1 fan and I didn’t care what anyone else would think or say because I felt that I had crushed that performance.

The Challenge

From now on, whenever I am tasked with a challenge, I think to myself, “Can I do this? Do I want to do this? Is there someone I can ask for help along the way?” You can be your biggest supporter and your biggest critic at the same time. The next time something pushes you out of your comfort zone and you’re about to retreat, ask yourself “why not me?” Discomfort is a sign that you’re changing and let that be a motivator. You don’t need others to validate the paths you choose on your journey to living your most fulfilled life. If you can’t be your #1 fan, who can?

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