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Listen First. Then Teach.
Drew M.

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Hourly Rate: $100
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About Drew

Bio

I spent twenty years sitting with people - asking questions, listening carefully, and figuring out what they actually mean versus what they think they're saying. That work has happened in one-on-one conversations almost exclusively, across people of all ages and backgrounds, in contexts ranging from early-stage business founders to professionals trying to solve problems they couldn't quite articulate yet.

What I learned from thousands of those conversations is that most people (adults and...

I spent twenty years sitting with people - asking questions, listening carefully, and figuring out what they actually mean versus what they think they're saying. That work has happened in one-on-one conversations almost exclusively, across people of all ages and backgrounds, in contexts ranging from early-stage business founders to professionals trying to solve problems they couldn't quite articulate yet.

What I learned from thousands of those conversations is that most people (adults and students alike) don't struggle because they lack intelligence. They struggle because nobody has asked them the right question yet, or listened carefully enough to understand where the real confusion lives.

That's what I bring to tutoring.

My teaching experience is primarily one-on-one, but I do teach in front of classrooms and even 200+ person audiences. In every case, I am someone who spends time in deep individual conversations, finding exactly where understanding breaks down and building a bridge from confusion to clarity - one person at a time.

The students I work best with are middle school through adult learners who feel stuck, who've been told they don't get it, or who learn differently than the classroom allows. I work at their pace. I ask more than I tell. And I don't move forward until the thing that was murky is genuinely clear - not just repeated back correctly.

I'm particularly drawn to working with students on critical thinking, communication, and any subject that requires figuring out what question to actually ask - because that skill, more than any content knowledge, is what determines whether a student struggles or thrives.

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Education

LaSalle University
Finance
University of Pennsylvania
Masters
MIT Sloan
MBA

Policies

  • Tutor’s lessons: In-person
  • Hourly Rate: $100
  • Travel policy: Within 25 miles of Orinda, CA 94563
  • Lesson cancellation: 24 hours notice required

  • No background check

  • Your first lesson is backed by our Good Fit Guarantee

Schedule

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Approved Subjects

Business

Business

Zero-to-one is the hardest phase of building anything - and almost nobody teaches it as a complete practice because almost nobody has done it repeatedly enough to know what it actually looks like from the inside. I have. For twenty years my sole professional focus was the zero-to-one arc. Find a problem worth solving. Get in front of the people who have it. Listen until you understand it more clearly than they can articulate it themselves. Then shape what the product or business wants to become based on what you actually heard, not what you hoped to hear. I did that loop across multiple ventures over two decades. I know what it feels like when you're finding a real problem versus a assumed one. I know what a great customer discovery interview sounds like versus one that's leading the witness. I know the moment when messy human insight starts to cohere into a clear product direction, and I know how to help someone get there faster than I did. Peter Thiel wrote about why zero-to-one matters. I teach people how to actually do it. I work best with MBA students in entrepreneurship programs, undergraduate product and design students, early stage founders running their first real discovery process, and product managers who want to get better at the front end of product development. Sessions are one-on-one and entirely practical. We work through your specific situation - your problem space, your hypotheses, your interviews, your synthesis - until you can run this process yourself with confidence. This is not a framework. It is a practice. And twenty years of doing it is what qualifies me to teach it.
Elementary Math

Elementary Math

Most kids struggle with math because they think there's one right way to solve a problem - and if they don't see it immediately, they assume they're bad at math. What I teach, grounded in how MIT approaches problem solving, is that there are always multiple ways in. Once a kid discovers that, something shifts: they stop doing math and start playing with it. My background is twenty years of creative problem solving in genuinely messy situations - launching new products, building new ventures, and navigating high-stakes decisions where the answer was never obvious. That's the same muscle I help kids build. What parents tell me again and again is that their kids didn't just get better at math - they started thinking more creatively, enjoying the process, and carrying that confidence into everything else they do.
English

English

English comprehension isn't about knowing the rules. It's about developing an ear for how the language actually works, which takes time, exposure, and someone who can explain not just what's correct but why it sounds right. I developed that ear at the University of Pennsylvania, where rigorous writing instruction is mandatory, and through creative writing at MIT Sloan - two institutions that treat language as a precision instrument, not a set of rules to memorize. My background is in storytelling, communication, and twenty years of high-stakes writing in business contexts where clarity wasn't optional. What I bring to students is the ability to find exactly where comprehension breaks down - the specific place where the language stops making sense - and rebuild from there, one genuine understanding at a time.
Prealgebra

Prealgebra

Pre-algebra is the moment math stops being arithmetic and starts being a language, and how a student crosses that threshold determines how they'll relate to quantitative thinking for the rest of their life. What I teach, grounded in how MIT approaches problem solving, is that there are always multiple ways into a problem, and finding them is more valuable than finding the answer. My background is twenty years of creative problem solving in genuinely messy situations - launching new products, building new ventures, navigating high-stakes decisions where the answer was never obvious - and that's the same muscle pre-algebra is trying to build. What parents tell me again and again is that their kids didn't just get better at math - they started thinking more creatively, enjoying the process, and carrying that confidence into everything else they do.
Public Speaking

Public Speaking

I help people communicate clearly and confidently in high-stakes situations - job interviews, pitches, presentations to senior audiences, and any moment where the pressure to perform makes it hard to think straight. My background is unusual for a communication coach: I spent fifteen years leading teams through high-pressure pitches at Fortune 100 companies including P&G, Levi's, and Stanley Black & Decker, and before that in investment banking at UBS. I know what those rooms feel like from the inside, and I know what separates the people who hold up from the people who fall apart. The approach is grounded in applied improv not as a gimmick, but because the listening and real-time thinking skills improvisers develop are exactly what work when a presentation goes sideways. Sessions are practical, specific to your situation, and focused on what you can actually use before your next high-stakes moment.
Reading

Reading

Reading comprehension isn't about understanding the words. It's about knowing what to do with them once you have them, which is a thinking skill as much as a language skill. A child who loves reading but struggles to show what he understood isn't a poor reader. He's a reader who didn't yet find the bridge between what he feels about a text and what he can say about it. I developed that bridge myself at the University of Pennsylvania, where writing and reading are treated as inseparable disciplines, and deepened it through creative writing at MIT Sloan, and what both institutions taught me is that organized thinking on the page begins with organized thinking in the mind. What I bring to students is the ability to find exactly where that thinking breaks down (where the sentences stop connecting and the paragraphs lose their thread) and rebuild from there, one genuine understanding at a time.
Writing

Writing

Writing isn't a skill you develop in isolation - it's what happens when your thinking gets clear enough to put into sentences. That's what I help students find. My own writing leveled up at the University of Pennsylvania, where writing isn't optional, and deepened further through creative writing at MIT Sloan, and what both institutions taught me is that the process matters more than the product. I'm a natural storyteller - people come to me for essays, stories, scripts, and comedy - and what I bring to students is the ability to find the emotional truth they're actually trying to express - the thing underneath the assignment, and help them build a piece of writing sturdy enough to hold it. That instinct came naturally. The discipline to shape it came from Penn and MIT. I teach both.
GMAT
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Hourly Rate: $100
Contact Drew