Episode 119: Running a Tutoring Business with Jesse Hartman of Hartman Tutoring

Jesse Hartman is the co-owner of Hartman Tutoring and has over 20 years of tutoring experience. Since he started tutoring back when he was a student at Emory University, he has prepared students for nearly every standardized test and tutored them in every subject available.

In this episode, we discuss how Jesse sees himself as an “academic guide,” how he teaches his students learning tools that go beyond the test, and how he incorporates what he learned as a rapper into his work.

 
 
 
 
 

Read the transcript for this episode:

Welcome to Educator Forever, where we empower teachers to innovate education. Join us each week to hear stories of teachers expanding their impacts beyond the classroom and explore ways to reimagine teaching and learning.


Jesse Hartman became the co-owner of Hartman Tutoring in 2006 and has over 20 years of tutoring experience. His goal is to reach learners not as a teacher, but as a mentor and academic guide. Jesse has prepared students for nearly every standardized test and in every subject available. He is currently the director of Hartman Tutoring and continues to tutor in New York City and beyond. Welcome, Jesse, so nice to have you here. 


Jesse Hartman  

Thanks for having me. Appreciate it. 


Lily Jones  

So any direction you want to take this, can you tell us about your professional journey? 


Jesse Hartman  

Sure, the journey began when I was really a child watching education happen in my household, both my parents were public school teachers, and then my mom went on to become a tutor after my dad passed away when I was around 10, just so my mom could be around the house a bit more, take care of myself, my little sister. So I watched education happen in many forms, and I didn't know it, but I was silently becoming a bit of an apprentice and learning not just about education as a whole, but also about one on one education in particular. Through the lens of my mother as a tutor, and after I graduated from college with a degree in philosophy and television production, also known as nothing, I teamed up with my mom and we became kind of a tutoring partnership, a mother son duo. We didn't intend to create a business. We really were just two people helping out kids in the neighborhood of lower Manhattan, and after a few years, before we knew it, we had too many students for the two of us to handle. So we started hiring a few independent contractors, and we made an LLC, and suddenly I owned a company. So that went on for a long time. My mother retired right around COVID, and I've been the managing director basically since we formed the LLC in 2006 and have been running the shop the last bunch of years on my own. 


Lily Jones  

Awesome. I love that story, and how cool to be, like, part of a family business that gets off the ground together, like, collaborate with your mom that way. 


Jesse Hartman  

That is the case. Yeah, it was really special. And I felt quite fortunate to be able to be a part of something so organic. We didn't have any intentions of launching some sort of monster, epic business venture. But it was, it was really what we needed for our individual selves and for the family, and it was something that was really quite a true passion project for both of us. We both love working with children, and we enjoyed working with each other. So it came together really well. 


Lily Jones  

I like that idea, too, about being an apprentice. My dad was a college lecturer. My mom taught for a couple years before I was born. But I feel like they're very much like teachers, and I've never really thought about that in that way of being an apprentice as a kid, you know, and thinking about absorbing all this way of being.


Jesse Hartman  

Yeah, I remember, when I was studying Socrates, I learned that his mother was a midwife, and that he claimed, or somebody claimed, that he claimed that he was able to see life taking place in his household all the time, and that by witnessing life happening in front of him, he became an observer to the truth of human nature, and that began his quest of questioning truth and having an understanding deeper than the surface. And I think that a lot of us might take for granted is what we see around the household when we're kids, what we absorb from our parents, either through their professions or just through their nature. There's a lot to be said for just the natural entity of picking things up from what's around us. 


Lily Jones  

That's beautiful. I love that Socrates story too. And just the idea of, like, seeing life, I mean, so much of teaching, I think, or being around kids too, is seeing life in all these different ways. 


Jesse Hartman  

That's for sure. 


Lily Jones  

So tell us a little bit more about Hartman Tutoring. Like, what do you offer? What's your approach? 


Jesse Hartman  

Yeah. Yeah. So we offer as much as we can. We're here to be as helpful as possible. So we really try to reach a wide range of students, in terms of subjects, in terms of ages, in terms of capabilities and interests. And now with the online platforms, we are extending beyond New York City. We started out really as a neighborhood, family working business. We operated in Tribeca, in lower Manhattan, and then spread out throughout New York City. And then in 2020 as many businesses did, we hit the online model and pivoted to be able to extend really just services and offerings of help during a time that was pretty tough for kids and for families on the educational front. So that was the beginning of our online work, and over the years, we've really extended more into a lot of zoom tutoring that actually we find to be occasionally more beneficial than the in person approach in terms of the services that we offer. It's a lot of enrichment, a lot of test prep, a lot of executive functioning coaching and a bit of critical thinking coaching whenever we have the opportunity to. That's something that I really hold near and dear to my heart. I love working with students specifically on critical thinking and being able to weave it into their academic pursuits, but largely just helping them be able to be more clear thinkers and have a more profound understanding of how to arrive at truth. So when it comes to test prep, we do a lot of the standardized tests the whole alphabet that everybody's heard of. With enrichment, we get a lot of calls for math and writing. So really, we go where the calls take us, but the bread and butter of what we really offer is being attuned to what students need in the moment. Everything we offer is personalized. The goal is to really be able to see what a kid really requires in their own way. So I've never been a classroom teacher. My parents were, my wife is. I have immense respect for what goes on the classroom, but I really value the ability to work one on one with the kid. It's really special experience. And so we take our entire model from that concept, the idea of being able to mold everything to what the kid needs and who the kid is. So the first step is, who is the kid? What does the kid need? Who is that kid? We have to be attuned to what we see in front of us, so we work really hard to be able to read the kid carefully, understand who they are, not just at once, not just with an initial assessment or diagnostic, but we offer continuous assessments throughout the process. It's an ongoing assessment experience, being able to read the kid from moment to moment, see what they need, and be flexible. So we juggle this trifecta approach of Content Strategy and emotional support, where we're tying in those three ideas, no matter what we're doing, no matter who the kid is, we're weaving all of that together as we go. I think that concept of personalization, or that approach, is so key, too, and something that as a classroom teacher, you know, I wanted to do having 30 kids and one me was a lot harder. But then, you know, times that I've had being one on one with kids, or even, like, with my own children, it's so much easier, you know, and so much better, because you can really get to know the individual kid and create these different pathways without thinking about, like, oh, okay, I'm doing something that like, hopefully I can bring in these 30 kids with all these different uniqueness, you know, to them. So I love that that's a focus. And I think that's something that like, really should be leveraged in tutoring. Yeah, it blows my mind. The teachers are able to do that, to be honest, the wide variety of kids, especially since COVID, I've seen the spectrum really grow. It's it's nearly impossible to reach everyone in terms of the learning styles, in terms of the difficulty level, in terms of just using interest topics to be able to capture everybody and make them engaged, the the one on one approach to me, it doesn't often even feel like I'm working or teaching. I'm kind of just hanging out with a kid, and the thing we happen to be doing is educationally related. It doesn't only make it easier, it makes it much more enjoyable. And the efficacy levels, I think, go up the entire experience that I understand to be teaching. It's all about that rapport, that one on one connection. So we craft everything around that. It'd be silly for me to pretend that teaching is teaching, and you just stamp something down. It's really about that, that connection. I often think of it the difference between being a stand up comic and you're in an auditorium or a coliseum of some sort, you know, hundreds, 1000s of people, or it's a podcast, and you have one person that you're talking to, you can really cater that message, cater that conversation, that interaction, to that individual who you're connecting with, as opposed to a quote, unquote audience or group. It's really a different communication style, and really we approach it that way, with that in mind. 


Lily Jones  

That's great. I love that, and I think that's important for everybody to think about, like, whether you're starting your own business or classroom teaching or whatever it is, like, who your audience is, and how to craft a message for them. And then going back just something else you said stood out to me about the critical thinking. And I think that to me often, as a curriculum developer, like thinking about the bigger why of why we teach things, and it often is about these skills, right? Like critical thinking. If you have that, you can do so many things, and you can take it to all sorts of content. So I think it's interesting, especially as you talked about, you know, helping kids with standardized tests, and, you know, all of these things that externally they want, but really thinking about the bigger why, of like, the skills that we can help kids develop that will, of course, help them do better on standardized tests, but, like, even better, they'll do better in life. 


Jesse Hartman  

Yeah, the word skills is a really good one. I'm glad that you're hitting on that the notion of content and grades, those are usually, like, kind of the two sides of the seesaw that keep people balanced when it comes to education, but grades are just the outcome and the content. Content is kind of just the medium that they're floating through. But what skills are they applying to make any of that happen? How do you ingest content and then how do you spit it out to get some sort of a greater result? It's these skills. And then once you take away school content, homework, lessons, tests, once you take away grades as some sort of a consequence or incentive. Well, then you're just a person in the world. You still need those skills. And so our hope is to be able to transcend the notion of grades and tests and all this stuff and be able to supply them with skills and abilities and incentive and ideas that can go beyond the classroom and really be sustainable, and provide them with something that's going to be more useful than just, Hey, I got this grader. I got into this high school or college. Obviously, that's often what we get phone calls for. So we want to achieve that as well, but we want to go a little bit beyond that and make sure that we're providing these kids with something that can be more than just, hey, this helped me on this one day. Cool. Thanks. It's kind of the Teach a man to fish, and the why idea is vital as well, because you can teach somebody to fish. If they don't know why it's important to fish, they're not going to be that good at it, and they might not even do it. So we have to not only show them how to fish, but provide them with a reason why it matters. What's the purpose? And kids deserve to understand. Why are they in this room doing this work? Eight hours a day, five days a week, the first 1822, 2730 years of their lives. What's the purpose beyond just so I can get a degree or so that somebody doesn't take my phone away if I don't get an 85 in this test, or whatever it is, there's so much more to education than just consequences or rewards, and very often that that's lost in the classroom setting. So it's, it's vital for us to impart that. 


Lily Jones  

Absolutely and going back to the fishing example, too, it's like, and it's even so much better if they love fishing too. 


Jesse Hartman  

Oh yeah, yeah, that's the secret sauce. If you can make it something that they enjoy. That's, that's an extra kicker, for sure. 


Lily Jones  

Yeah, that's great. Well, I love hearing about the approach, and I love the way that I mean, it's really, I think teaching is a creative job, right? Like, we see students, and we see their interests, and we see where they're at, and we like, put it in a magic pot and come up with solutions or try different things. And I know that you have a creative side of your own life. Um, can you talk a little bit about your creative side and how you mesh that with your professional side, sure. 


Jesse Hartman  

So I'm 43 I've been around a bit. I've done a few things. So when I was in high school, I was a writer and a comic. I tried out a lot of Stand Up Comedy in New York City when I was in high school, this was the road that I planned to pursue as a kid, people like Andy Kaufman, Adam Sandler, Chris Rock, these were heroes of mine, and in New York City, I'm surrounded by opportunities to grab a microphone. And so I did, and I ended up working as a comic for a while outside of school and basically in secret. But for the most part, this was, this is what I really wanted to do, was to communicate and engage and share. And what I found was that stand up was something that was really exciting and fun, but wasn't really all that satisfying for me. On an artistic level, I found myself, and I was very young, so I didn't see this through from a very mature perspective. I was seeing it as a kid, basically, but I found myself just trying to pull levers and push buttons that would make the audience laugh, because I found that to be what the job was. Instead of really trying to push the artistic experience of crafting and writing and honing and experimenting, I was like, let me just get on stage and do the job. So I put stand up aside around 2008 and pivoted towards a rap career. And I know that over the last few years with the internet, a lot of comedy and hip hop have started meshing people like Lil' Dickie or Donald Glover. And this is something that I think a lot of comics and musicians have done, is kind of shake hands and they go, Hey, let's try the other thing. But this was just really a natural pursuit of mine as well. I was rapping from the time I was a little kid. Like, literally at eight, nine years old, I was making tapes with my friends, and I had a rap group in college, and it wasn't like a joke. I wasn't like doing Lonely Island, Weird Al Yankovic, funny songs, I took rap much more seriously than I took stand up. And in 2009 I took it as seriously as I could while, mind you, building this business with my mother of this tutoring company. I hit the underground scene in New York City and started winning these freestyling contests, and I was in all these battles, and I came out with a bunch of songs that strangely hit and became popular in the independent music world. Won some awards, went on tour, went to festivals like did the thing of being an independent musician. And this was much more artistically satisfying for me. Through writing rap songs, I really got a chance to express myself in a way that didn't have much of an intention other than to share and to craft messages that I found to be sincere and meaningful, and I was really fortunate and grateful that they resonated with people, with listeners so performing and writing and recording and all that was a big part of my life. For a while, I was loving life as a rapper slash tutor. It was a lot of fun, but I stopped putting out music when I started taking the tutoring side a little bit more seriously, and just also, you know, I got a dog, and I was like trying to find a wife and all these things, and it just it wasn't something that really I was able to give the attention that it deserved. Being an independent musician, it's a full time gig, if not more. So yeah, I haven't put out any any songs or albums or anything in a while, but I still write the words just don't rhyme. And I still intend to live the life of a creative, expressive person. It just comes out in different ways. And as you said, teaching is a creative pursuit. It's all about communication. So to me, whether it's stand up or rapping or tutoring, I'm still very much so the same person. There's very little of a shift that occurs in terms of how I approach it, or who I am in those different arenas. So you're right, it is all creative.


Lily Jones  

 Yeah, that's so cool. Thanks for sharing. I think it's interesting just thinking about like, almost these, like creative levers that we can turn up in our life. I think for many of us, like, I'm a writer also, and an educator. And so there are different times or phases in my life where I'm like, Oh, I think I'm still a writer, but I'm not really writing. And then other times where I'm like, Oh, I'm writing a lot, and like, it's awesome, right? And so I think seeing that, it's like, no matter what you're doing, like having that experience or that approach, I think like you're saying you're still the same person, right? And it's like, a writer, expressive and creative in that way, I think I'm sure, you know, help students that you work with too. 


Jesse Hartman  

I hope so. Yeah, but I feel like, especially for a writer, once a writer, always a writer, whether you're writing or not, because writing is just an extension of speaking and thinking, and we are doing that all the time, and I think that the writers thought process and the writers communication style is still that of a writer whether they're actually writing or not. That might be a cop out for me, just so I can call myself a writer whether I'm writing or not, but I agree with you that I think that for an educator, it is a benefit. It's like an extra boost if you have a creative muscle. And the notion of being able to articulate your thoughts and your ideas and wanting to wanting to share, having that drive, that urge to put it down on paper, it is a skill that is applicable in the educational fields. When I go around trying to hire tutors and I'm looking at resumes and thinking about prospective staff members, I love looking for for performers, for people who have some sort of a background in being able to craft a concept and share it. And it doesn't matter to me whether it's theater or dance, stand up or rap or writing, whatever it might be, if somebody has a background in in connecting to me, that's kind of the backbone of tutoring.


Lily Jones  

I love that absolutely. And so shifting a little bit to the running a business side, I would love to hear any reflections you've had. You know, it seems like it kind of organically happened where it was like, Alright, I'm gonna do this thing with my mom, and now I'm running a business and thinking about, I mean, that kind of what happened to me. I was like, Oh, I'm doing these contracts. And then wait, I think I'm running a business. And so I would love to hear kind of what you've learned through that process. Sure, number one is to be true to yourself.


Jesse Hartman  

There's a lot of reasons to doubt yourself, to question yourself, especially as you're taking on new roles. You know, you don't go to business school, you don't know much about business as a whole, and suddenly you're running a business. And so it would make sense to be like, I don't know what I'm doing. This is wrong. Somebody else should do this instead of me. And yeah, you might not know what you're doing. You're gonna make mistakes. Somebody else could do a quote, unquote better job, but staying true to yourself is the anchor, and really believing your purpose and following that is always step number one. That doesn't mean refuse to stay open and don't listen. It's staying true to yourself while being open and while being flexible and supple and malleable, I take in as much as I give out when it comes to business understanding, but the goal is also for me to really follow the practice instead of the theory. I don't come up with ideas and then put them into play. I see what happens. I kind of let life happen, and then I'm like, Okay, let me you know, it's almost like the scientific method. I see what works and see what doesn't, and I have hundreds and hundreds and hundreds of hours of data. And from that, I'm like, Okay, this is what I think is true. Instead of starting with I bet this is true, and then I just try that out. No, I was really gifted an opportunity, because I started so young with tutoring to just kind of see what was out there. And I had a lot of experience of working with kids from the time that I was a kid, actually that the notion of connecting to a child came naturally to me, and then the educational component was something I got to just weave in as I went. So for anybody who's stepping into a business position and they might not feel automatically or naturally acclimated to it, trust yourself and let the hours and hours and hours of experience kind of guide you. I say practice before theory.


Lily Jones  

And I totally agree about the scientific method part in particular there, like I always think that when you can think about business or anything as an experiment, it just allows you to see like the data and the possibilities in a different way, and kind of takes the pressure off, because it doesn't have to be successful the very first time, which, like, rarely is anything. And then you get to see, you know, I'm doing this experiment, and I'm seeing how it goes, and you get to have this different mindset about it. 


Jesse Hartman  

Yeah, I think even attempting to gauge whether something's successful or not the first time, you don't really know what you're looking at, and so the barometer of where success is or isn't might be off. So just kind of letting life happen, I think, is the best way to go. And it's tricky in business, because who's going to pay you to do that? Who's going to sign up? But I always think about it this way. I always try to imagine a barber or a surgeon cutting hair for the first time, performing surgery for the first time. That happens. And obviously they go to school and they practice, and they do it in different simulations, different ways, but it happens for real for the first time at some point. And I have to keep that in mind every time I hire a new tutor and I pair them with a new student for the first time. And I have to tell myself, like, look, everybody has their first time. It's new for everyone. I have to trust what we put in place. Have to trust the training, trust the preparation, trust my ability to hire somebody properly. And so as a tutor or as a business owner, being able to say I have a reason that I'm doing this, there's a there's a purpose to my pursuit, and it's going to be purpose over profit. That's another little motto of mine, I got to keep that purpose in mind more so than the, you know, the it's a business, the potentiality for financial repercussions is there, but let me not let that be my North Star that I'm following. Let me let the purpose be what I follow. And that's that's usually going to end up with a positive result. 


Lily Jones  

And I think teachers can really get behind that too, right? Like, it's like being a teacher, like we're often driven by a purpose of helping students or love of learning, and so bringing that purpose to whether you're starting a business or anything you do, I think really is often the greatest motivator. And I appreciate how you're also sharing, like, this reflection on supporting tutors too, right? Like, often running business, even if it's not that you're hiring tutors, like you find yourself hiring people, and then it's a different skill of leading people and teaching them in a new way. And so I appreciate that message of like, having patience with the process too. People need to learn. 


Jesse Hartman  

Yeah, patience, it almost it's an unspoken virtue when it comes to educators. We don't even bother saying it, because what are you doing here if you're not a patient person? But yeah, that was another interesting pivot for me when I started hiring tutors and training them, because I thought of myself as this, and for a while, I was this young tutor who was able to relate to children, because I was still kind of like young and like with it, like I knew what was going on. And then all of a sudden, I was hiring like, 27, 28 year olds, and they were younger than me. I was like, oh, so I'm like, kind of not the young person they are. And now I'm the same age as my students parents, and I'm like, okay, so that whole thing about me being the young tutor is completely I'm not that anymore. I'm the other tutor. Yep, time, and that's cool, like that. Transition has been a fun one for me. It's another funny feature of zoom, because when I was tutoring kids in person, I didn't have a little square with my face looking back at me the whole time. So I was like, Yeah, this is me, but now I get a real reflection of who I am, quite literally in the moment. But training staff members is something that I've really grown to value quite a bit as well, because it's just another type of education, and I'm not tutoring them, but the ability to communicate and connect and build a rapport is still there. It's still paramount. And you're right, there's leadership involved, and there's different skill sets I have to learn and then apply. But it's something I've really enjoyed as well, and it was another natural, organic progression for me, because being able to teach people how to teach people, it's like tutoring exponentially. So that's been a lot of fun for sure. 


Lily Jones  

Wonderful. Well, thanks so much, Jesse, it was great to talking with you and getting to know a little bit more about you. Can you tell people how they can connect with you?


Jesse Hartman  

 Sure. So our company is Hartman tutoring, H, A, R, T, M, a n. You can find us at hartmanuttering.com. All the information about our services and our philosophies and our approach, it's all there, and my contact information is there as well, but you can email me at jesse@hartmanuttering.com.


Lily Jones  

Wonderful. Thanks so much. 


Jesse Hartman  

Appreciate you having me. Thank you. Bye.


Transcribed by https://otter.ai



Lily Jones