Ask questions and listen more than you talk.
Stephanie is Founder and CEO of AdmitSee, a searchable database of crowdsourced student admissions data that matches applicants with accepted college students to drive better decision-making. In high school, Stephanie founded an educational charity that focused on funding education access for low-income female students. Her passion for access to education and information led her to pursue an early career in journalism. Having worked at CNN and NBC, she joined a financial news startup in New York City after graduating from Duke University. During that time, she served as an alumni interviewer for her alma mater, sowing the seeds for her interest in college admissions.
Stephanie went on to attend the University of Pennsylvania where AdmitSee was selected as one of 8 finalists in Wharton’s Business Plan Competition. She graduated from UPenn with a law degree and a Wharton certificate in 2014. Despite passing the NY bar, Stephanie turned down her law firm job offer to work full-time on AdmitSee and joined the accelerator ImagineK12 / YCombinator shortly after. In 2015, Stephanie was named one of Forbes’ 30 Under 30 in the Education industry and one of nine female founders to watch in 2017.
Where did the idea for AdmitSee come from?
Like many startup creations, AdmitSee was a product we wish had existed for us. When I applied to grad school years after I first applied to college, I was surprised at how little the admissions information landscape had changed. U.S. high school counselors are still massively under-resourced (the average caseload is nearly 500 students). As a result, the private consultant market – driven by just 5% of applicants who can afford the hefty price tag – is flourishing at $2 billion. For the other 95% of students, they’re still relying on many of the same resources I availed myself of two decades ago.
The core principle behind AdmitSee is information transparency and experiential insight. AdmitSee allows applicants to access real successful application examples and tap into the crowdsourced collective knowledge of peers. For today’s students, it’s more relevant info delivered in a familiar format.
What does your typical day look like and how do you make it productive?
My typical day changes month-to-month depending on what what hat I’m required to wear according to company priorities.
Right now, I’m primarily wearing my fundraising hat, which is very different from my typical operations hat. My fundraising responsibilities are split into the very exciting and the very banal. What’s exciting is talking about the company’s story and vision: what we’ve already accomplished, the challenges overcome, where we’re going, and how we’re going to get there. Talking about the dream on a daily basis reminds me of why I love what I do everyday. The less exciting part is the formulaic prep work that goes into each meeting: updating and tailoring our investor deck with stats or metrics relevant to different investors, constantly refining our financial projections, and aligning all the details with the bigger vision. I often joke that my job is just talking about my job. Very meta.
In terms of productivity, I don’t have a set routine, but I do start every day with a 10-minute meditation right after I wake up. It’s easy to fit into my schedule and puts me on the right track of mindfulness for the day.
How do you bring ideas to life?
I have an amazing team that lives and breathes what AdmitSee is about. Everyone has some ownership over the product, so we approach most ideas as a team. Ideas are born from company goals and priorities I set. We come into meetings with relevant metrics or user asks and, from there, we ideate on the best ways to achieve our company goals. We’ve become relentless about prioritizing, so we decide what to execute based on maximum impact – what will move the needle – and on project scope. We employ weekly sprints and retros. It allows us to track what worked and what didn’t, and then iterate. The details of defining a new feature plus designing, testing, launching, and marketing it are clearly divided amongst team members, so we’re a pretty efficient team of executors.
What’s one trend that really excites you?
Data science being applied to more traditional industries that lack information transparency. Personalized recommendation engines are ubiquitous across the consumer space, but there are countless decisions we make each day that have yet to be driven by data. I’m excited about empowering the individual to make more informed choices, especially in areas that impact our daily lives, such as healthcare, local politics, what to watch on Netflix or, even, education.
What is one habit of yours that makes you more productive as an entrepreneur?
I find that staying grounded makes me more productive. So, aside from my grounding daily meditation practice, I don’t get caught up in the ideological and lofty aspects of being an entrepreneur. My job is to get sh*t done, so I try to stay focused on practical tasks that need to be completed and set manageable goals.
I’m also really big on managing expectations. This applies to everyone I work with, whether it’s my team, investors, strategic partners or myself. One of the most damaging things to relationships is to overpromise and underdeliver. It erodes trust and respect, which I value a lot. Practically, managing expectations means setting realistic goals and updating stakeholders on progress. It’s essentially information transparency in practice.
What advice would you give your younger self?
Trust your gut (caveat: the good part of your gut that tells you “this is right”).
I didn’t discover this about myself until recently, but I’m a highly intuitive person when it comes to judgment calls. Whenever I’ve gone against my intuition and solely rationalized important decisions, I’ve made costly errors. I have yet to regret a decision I’ve made with my gut.
However, I do want to make a distinction between trusting your gut and operating out of a gut emotion like fear. A good gut decision will feel aligned with your true north, even if it’s accompanied by some fear and trepidation. You can tell the difference because decisions made out of fear will feel like avoidance whereas decisions made out of true intuition will feel like an opportunity.
Tell us something that’s true that almost nobody agrees with you on?
Silicon Valley / the tech industry is not the center of the universe. [Pause for audible gasps from readership.] People outside of tech are building things, too. Real businesses that solve real problems. Just because a company is high-growth and venture-backed doesn’t make it more legitimate or more important. Yes, tech companies often transform the landscape of an entire market and can be drivers of much-needed reform, but I’m personally more impressed by people who are motivated by the mandate to solve real problems rather than just building something cool.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
Ask questions and listen more than you talk. Entrepreneurs feel this need to be larger than life and to showboat. I can empathize. It’s definitely a skill you need to sell your product to users / your vision to investors. But it’s important to dial it back once in a while. I love the quote “Be more concerned with being interested than interesting.” Instead of going into conversations feeling the pressure to impress, it’s a lot less stressful to go into conversations with a curious mindset and with the assumption that the person across from you has something to teach you.
What is one strategy that has helped you grow your business? Please explain how.
This is less a strategy and more a hard lesson we learned. The appearance of growth is not the same as growth. YCombinator cautions that for all its companies. It was something we knew but didn’t really take to heart in the first couple years of business. So many startups get caught up with looking like a high-growth company and molding themselves to what they think investors want to see in order to move to their next stage of funding. This can distract you from actual growth and finding product-market fit. Our strategy now is to focus on the KPIs that matter to us internally because, ultimately, the KPIs that matter to the business will be the ones investors are interested in, too (I know, truly groundbreaking stuff).
What is one failure you had as an entrepreneur, and how did you overcome it?
Like a divorce, parting ways with a co-founder is objectively a failure. But, for me, it was also a huge opportunity for growth. The experience taught me how to navigate conflict, how to be “confrontational” without the negative connotations, how to communicate and negotiate more effectively, how to embrace discomfort, how to rally and inspire my team in the face of uncertainty, and how to ask for help when I need it (I hired an executive coach when things got really tough). It may seem counterintuitive, but the experience make me more confident and passionate about AdmitSee because it forced me to clarify and articulate my motivations for pursuing this idea. It proved to me that I’m working on AdmitSee not because it’s a startup or a means to some other end goal but because I care deeply about what we’re trying to do; AdmitSee IS the goal.
What is one business idea that you’re willing to give away to our readers?
Not sure this can actually be a viable business, but I’d love a service or app that can match me to on-demand volunteering opportunities nearby. I occasionally volunteer at a homeless shelter in SF, but the schedule is rigid and requires me to commit ahead of time. Many volunteer positions require orientation/training and minimum hours of commitment. I’d love a centralized database to find on-the-fly opportunities to give back day-of. For example, if I find myself in the South Bay after a meeting but want to avoid rush-hour traffic back to the city, it’d be great to help a local nonprofit out with a discrete task that fits my skill set. Or, I dunno… puppy-rentals for dates.
What is the best $100 you recently spent? What and why?
This might not be fair because the value was more than $100, but I organized a team retreat to Whistler booked solely on credit card points. Everything from housing (generously donated by an employee’s relative) to airfare to car rental was completely free. The only thing I gave in and spent money on was a nice meal out one night, which came out to an insanely reasonable $120. The trip came on the heels of a super busy, tumultuous application season and was a great way for us to reset as a team for the new year.
What is one piece of software or a web service that helps you be productive? How do you use it?
This is a bit of a throwaway since everyone uses Slack, but I love Slack. Aside from the obvious collaborative features, I use Slack as a personal organizational tool. I throw articles I want to reference later into my private channel and set reminders for myself. I’m still very old school and also have a physical planner, but I love that all my Slack messages are searchable.
What is the one book that you recommend our community should read and why?
There are tons of how-to’s on growing your business and being a better leader. I read for pleasure, so I personally don’t read a lot of books related to work, but I do watch a lot of short videos and TedTalks. I think being a better leader starts with self-awareness and self-improvement. Brene Brown’s 20-minute TedTalk is truly an ode to authenticity. It contains gems such as “Truth and courage aren’t always comfortable, but they’re never weakness.”
What is your favorite quote?
There are a lot of quotes I try to live by and ones that I apply to my personal life, but, in the professional realm, my favorite quote has got to be: “The function of leadership is to produce more leaders, not more followers.”
Stephanie Shyu on LinkedIn: https://www.linkedin.com/in/stephaniejshyu
Stephanie Shyu on Twitter: https://twitter.com/sjshyu
AdmitSee on Twitter: https://twitter.com/admitsee
AdmitSee on Facebook: https://www.facebook.com/admitsee/
Stephanie Shyu on Medium: https://medium.com/@sjshyu