Letter to My Younger Self: Dear Jaime…

Case Foundation
#FacesofFounders
Published in
5 min readJun 4, 2019

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The Case Foundation commissioned research about five years ago to look at the core qualities of changemakers, entrepreneurs and innovators who found success, and it showed that innovators and leaders of all races, places and genders have brought forward transformational changes throughout history. It also reminded us that it wasn’t the right connections, some special genius, the perfect resume, or a degree from a prestigious institution that brings breakthroughs to life; it is the ability to Be Fearless. Being Fearless doesn’t mean that the entrepreneurial journey is straightforward or easy; it requires risk taking, learning from failure and reaching outside your comfort zone to continue moving forward. And these important traits can sometimes be easier to spot when you’re looking back on your journey than when you’re in the midst of building your company. So, to bring the unique and varied stories of founders to life, we have asked a few female founders and entrepreneurs of color to write a “Letter to My Younger Self” to share lessons they have learned along the often windy road of entrepreneurship with those who may follow in their footsteps.

In his “Letter to My Younger Self” Jaime Martinez, founder of Schola, an educational technology company, writes about the lessons he learned and unexpected experiences he had as he built it from the ground up. Schola provides families with the tools they need to find the school and educational programming that best aligns with the needs of their child — from public to private, pre-K through grade 12.

Hi, 2012 Jaime,

How’s the Teach for America program going so far? Right now, you’re probably grading math papers at Quinton Elementary School (go, Sharks!) in the Littleton School District in Avondale, Arizona. I’ll let you in on a secret: This experience will act as a catalyst for creating your own company.

Yes, you’ll become an entrepreneur!

You will forgo law school and create an innovative educational technology company. How will you get here? Well, it won’t be easy, but it’ll be worth it.

Your company will be named Schola (from the Latin word for school). Simply put, at Schola you’ll help families connect to the right pre-K–12 schools for their students. The way we do this is by providing an easy-to-use online tool that matches students to schools based on their needs and interests.

See, right now you’re witnessing the problems that exist in your classroom with students who aren’t on the optimal path for their learning journey. You know that they might be better off in another school, but suggesting that could land you in trouble because of the way schools are funded. Schola will empower families by asking simple questions that allow them to rethink how they connect to schools and even start the enrollment process online!

Like I said, the journey there won’t be easy. Choosing the right staff will be crucial to the future of the company. People will come and go, but keep in mind that you will need a team that really believes in the core mission: putting students in the right schools. Without this drive, the long hours will be hard to manage (and trust me, this will be anything but a 9–5 job). Your core team will help you get through the highs and lows that lie ahead.

Additionally, finding the right people to help you with the technical aspects of creating software will prove a time-consuming task. Every day will be a learning experience, from understanding the differences between coding languages while working with onshore/nearshore/offshore teams, to so many tech acronyms that your head will spin, and frequently scouting for new tools to incorporate into your work arsenal.

Be Prepared for Failure

You think that a tool this useful will easily get traction, right? Wrong. You’ll fall in love with your first version of the product and think you’ve reached the zenith of education technology.

Your first product will fail.

The good news is that you’ll learn valuable lessons that will lead you to improve the product. From there, you will stare into the abyss when debt piles up while working on a better product, but make sure to hold on and push forward, because the best is yet to come.

You’ll have to attend events and ask parents to go through the process with you and your team. You’ll need countless hours with parents, students and school leaders to make sure you’re building everything they need. With your team, you’ll travel to schools and meetings throughout the country, learning about the different educational landscapes of each state and the different challenges parents and schools face.

And throughout this crazy experience, you will need to balance your work with your family life. Let’s just say that your family is going to grow substantially in the next couple of years, and spending time with them will give you the energy to keep going every day.

I’ll give you three simple tips I wish someone had given me:

1. Make good use of the mentors you meet in the coming years, but don’t take every opinion to heart. In the end, your customers will show you what they want from your product.

2. DO NOT SPEND MONEY ON SWAG. Yes, it looks cool. Yes, everyone has it. In the end, you don’t need it. Make sure in these coming years that all your money is going to things that will make more money for the company. Cool T-shirts are not it.

3. Communication is key. This one will be the hardest, because we both know that sometimes it’s hard to communicate the vision we have in our heads. However, finding ways to communicate this to your team and your investors will get them motivated and invested in what you’re trying to achieve. Don’t assume they know because you know.

Embrace the struggle, because I promise you the juice is worth the squeeze. Once the platform gets going, you’ll have more than 500 school users in Phoenix alone, with 10 percent of them being premium users. You’ll enroll more than 150 students in your first couple of months. Several people will make significant investments. You’ll go through SEED SPOT and LearnLaunch incubators, and one of those will involve living in Boston.

Be sure to enjoy the ride, because in 2019 there’s still a long way to go.

Best,

2019 Jaime

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We invest in people and ideas that change the world. Founded by Steve and Jean Case in 1997. Take risks. Be Bold. Fail forward. Be Fearless.