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Jesse Roselin: Finding His Path in Education and Entrepreneurship

Updated: May 27, 2022

Jesse Roselin is an educator, entrepreneur, and business leader with 20 years of teaching and tutoring experience, 17 years of business management, and 15 years of nonprofit experience. He founded Tutor Corps and Pacific Preparatory and co-founded the Tutor Corps Foundation.

Jesse first became interested in education as a senior at Stanford when he ended up volunteering in a fifth grade classroom doing a lot of reading support. This experience caused him to apply for Teach for America where he was placed back at that school to teach eighth grade.

Jesse's experience with the urge for freedom:

After feeling a bit limited and wanting more freedom and control, Jesse left his teaching job and began tutoring so he could have more control over his time and focus on individual students.

Driving around the bay area in his 1986 Ford Escort calling everyone he knew, Jesse started Tutor Corps.

It started just with himself in 2002, and he slowly brought on more tutors and grew Tutor Corps and now Jesse has 186 teachers that work for him across America. He also started a fully accredited online and in-person K-12 school called Pacific Preparatory.

Prior to creating these organizations, Jesse did not really know what he wanted to do. But when he took the first step and decided to try Teach For America, he started to find his path.

"I am a new tutor who loves tutoring, where do go from here?"

Jesse believes transparency is super important and he talks about how he helps new tutors decide what is best for them whether that is working for his tutoring company or starting their own business depending on what their hopes and strengths are.

For new tutors, there are so many ways of getting your name out there, Jesse offers some of his best pieces of advice including getting on Nextdoor, making SquareSpace websites, joining facebook groups, reaching out to the chamber of commerce, and more.

Investing in people and crafting your vision:

For the first ten years of growing his business, Jesse was really focused on the teaching and took a slower approach to growing the business. “Investing in people” Jesse says is his biggest lesson and he discusses how important it is to treat employees well and build a positive company culture.

Having a clear vision of where you want your business to go is really important. As Jesse worked over time, he developed his vision but he talks about several things that especially helped him in doing this like listening to podcasts where other people tell their stories (just like this!)

Jesse created the Tutor Corps Foundation so that all types of students could be supported. He uses a corporate philanthropy model that allows him to take resources of Tutor Corps and donate to the Tutor Corps Foundation.


Jesse Roselin 0:01 So the crazy thing was in East Palo Alto I was working in a very under resourced school called Cesar Chavez school. And then tutoring kids in Woodside that were billionaires. And literally, it was 10 minutes. It was like a 10 minute drive between those two spots. And I thought that was so stark, like that difference between the billionaires on one side of one on one on the Palo Alto side, and then this this under resourced school on the other side, and starting the foundation, I started the foundation in 2004. The idea was basically to marry my desire to help all kids, and while also running a company that charges really high prices, frankly. Sean McCormick 0:47 Welcome to the Earn More Tutoring podcast. Here you will hear the real stories of teachers tutors and other educators who took ownership of their time and money. If you want to earn more with your tutoring skills. This is the podcast for you. Today's guest is Jesse Roselin. Jesse is an educator, entrepreneur and business leader with 20 years of teaching and tutoring experience, 17 years of business management and 15 years of nonprofit experience. Jessie founded tutor corps and Pacific preparatory and he co founded tutor corpse Foundation. Welcome, Jesse. Jesse Roselin 1:22 Thank you for having me, Sean. Sean McCormick 1:23 Yeah. So Jesse, I'd love to learn more about how you got to this point and how you created Pacific preparatory and tutor corps. So if you could tell us about what what the journey what you what your journey was like to establish those organizations. It'd be great to learn more about that. Jesse Roselin 1:41 Yeah, I'd be happy to share I actually first got interested in education. As a senior at Stanford, one of the one of the TFA folks who was teaching in East Palo Alto named Chrissy Rodriguez, she was teaching fifth grade and she was a Stanford alum herself. So she came back to campus and did a talk, looking for volunteers. And so my senior year, I ended up volunteering in her classroom, doing a lot of reading support for kids, because she had a lot of English language learners. And that really got me excited about teaching. And I applied to TFA. And I actually got placed right back at that school, teaching eighth grade English language arts and social studies. So I thought that was pretty cool. In fact, those same fifth graders that I had volunteered with ended up coming into my eighth grade class, my second year of teaching. So that was a nice sort of full circle, in terms of being able to connect and teach those kids. I just, I love teaching, I really, I really enjoyed it. But I found that there were certain parts of being in the public or private school system that were limiting. I wanted a little bit more freedom and control over my time. And also, I wanted the ability to really focus on individual students, I found that having 32 kids in each of my classes was just too much to really be able to make a difference. In each kid's, like learning challenges. So I started tutoring, and it was a great time to start tutoring. You know, tutoring has always been around for ever. If I look at the Socratic method, look back to Oxford and Cambridge for the tutorial method. But you know, in the Bay Area, people are just doing it fairly ad hoc, people just having their own little shops. So I just started tutoring, and I started volunteering and substitute teaching and private schools and getting to know people. And so that's how I started tutor Corps. I just was driving around in my 1986 Ford Escort with a lot of rust damage, because it was for my godfather, who got it from his mom in Chicago. And so it's all rusted out. And all my students called it like the beater car. And I just drove around the Bay Area hustling calling everyone I knew emailing. My first web page was called this is this is 2002. So this is still kind of early. And in the world of, you know, the internet. We have a lot of dot coms coming on just like Google is just starting to get big. So I had my own website called Jessie's private tutoring services. And yeah, that was it. And so then, over time, it's been now I'm going into my 20th year. So it's been a little while. And it basically started just with me and then I brought on trusted family members, my brother, my cousin, then a few trusted friends. And now I have like 186 teachers that work for me across America. We tutor kids all over the world. We have our school which started out as sort of a homeschooling model has To become a fully accredited K 12. School online and in person, so we have kids in Denmark and Australia and Fiji and Chicago, New York, California, wherever. And it's, it's lovely. I have yeah, I've really enjoyed building it slowly. And making sure like I never took out a loan or anything, I just just kind of kept on churning and kept on hiring people and built it. So it's a very strong, sustainable organization right now...

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