See How Theo Started His Own Successful Tutoring Company

Are you looking to quit your job to start your own business?

I’m going to show you how Theo quit his job and moved across the country to become a tutor for his own company.

Many of us are looking for some extreme story about how someone started the next Facebook or about how the buddy who knew about a stock that was going to take off. The reality is that true hustlers are making moves behind the scenes. Right now’s the best time in history to make a living as a freelancer. It’s also the best time in history to do whatever you want to do. Continue reading to see how Theo was able to start his own profitable tutoring business.

tutoring for money

We looked at why you need to stop listening to weirdos on social media about passive income. I want you to get into the habit of increasing your income and investing in yourself. I don’t want to see you looking for some shortcut that doesn’t exist.

Theo has been a reader for a while. We had messaged each other many times before he launched his tutoring business.

Let’s take a look at how his journey started…


I have an early version of a business plan I’m developing out in Seattle. I tutor (thanks to your articles) and I kick ass at it. I love teaching kids and the parents pay me well.

I’m in the process of building out. What that build out will look like, I’m not sure — but I trust you to give me sound advice. Would you mind taking a look?

I’m running a summer course through my company, StudentCircle. We’re going to be offering kids (Grades 6-8) an early opportunity to learn about money. I’ve established that there’s a need. I’ve calculated out rates, rentals, time, place, etc. I’m beginning to advertise and I’m building the curriculum at the same time. I’m currently working on a timeline. What needs to go up where and when. Systems and deadlines. I love this kind of work. Where I have an enormous task in front of me is building the curriculum.

I wonder if there is any way I can buy your time in a way that would be useful for me, in building a curriculum for teaching kids about money. Your thoughts?

My current plan is to spend a few days in the library, teaming up with the teacher I’m training to run the course, reading, compiling notes, comparing, and cobbling together ideas — which will later be transformed into activities.”

Theo was in the beginning stages of his business. Then I heard from Theo a little later…

“I always love getting updates from you, because I know you’re helping someone new to the success I’ve been inspired to attain from your blogs, books, and stories.

When I started my own small business — the first thing I did was your Craigslist test. Now, I have friends and family from my home, back east, visiting me each month. They wonder if they can also make a move and change their lives. You know what I tell them. My company continues to grow and I’ve finally hit the point where I’m making more than my friends with jobs in Starbucks… and I have other goals but it’s just so nice to know that I can finally sustain myself.”

I love to hear from my readers. Then over a year later I heard from Theo again…


Thanks for all you do. I hope I can meet you one day and thank you in person for the role you played in my launch. I just found your words at the right place and time…

Every time I hear from you, I’m grateful.

I just came back from 30 days on the road. In my second year of running my tutoring company, I thought about how can I build this company in a way that will inspire my creativity and work ethic. I hired 10 tutors in 5 cities across America and I’ve now been mentoring a young high schooler in business for a year. So much is happening for me…”

As you can tell, it has been a huge year for Theo. This is what happens when you focus in on one thing and ruthlessly chase it until you get to where you want to be instead of making excuses or complaining.

Let’s see exactly how Theo was able to quit his job and start his own tutoring company…

I sent Theo a bunch of questions and he responded to them. There’s definitely something in here that will help you get started with your own freelancing career.

How you can tutor for money

1. What do you do for a living now and how did you get there?

I employ myself as a tutor through my own business, StudentCircle. I put most of my profit back into the company, but the company does take care of me, and I plan to receive increased dividends as time goes on. I also continue to work freelance in video, where my management capacity has made me an attractive hire, and in writing, where my constant instruction (via tutoring) has strengthened my abilities considerably. I believe that anything I start on the side better push my overall progress toward my major goals.

I recently started Seattle’s largest Pokemon events community, but that was just to meet girls.

[Martin’s note: Further proof that you don’t need to spend money on clubs to meet someone.]

2. What stopped you from reaching your goals?

Fear is what stops everyone from reaching their goals. I moved across the United States, knowing that my demons might take the long route — but they’d certainly catch up. That battle is always ongoing. I don’t know if I’ll ever completely win. I focus on consciously taking my fears apart, bit by bit.

I like to think of that scene from the most recent Batman where Bruce Wayne gets beaten to hell and thrown to the bottom of a pit/prison. The human experience is very, very diverse and it’s rare we step back and conceptualize this. Everyday, there are projects you haven’t even begun to fathom yourself doing. This is like sitting at the bottom of Batman’s prison. I think we fear the prospect of an extremely long and hard path and so fear blocks out possibility for us.

I think this battle gets harder and harder as you age, unless you gain the ability to navigate. Eventually, the current becomes too strong for those who haven’t become swimmers.

[Martin’s note: Simply brilliant. I love the brutal honesty here.]

3. What was the first step that you took?

The first step was my greatest step. The first step was giving up on the advice I had been given my whole life to listen to my inner voice and manifest those dreams into a plan. The plan came to me at a simple time in my life, when I was working, exercising, and writing. I miss that life sometimes. Once I had that plan, I knew there was no other path for me. I decided I’d leave the life I knew and embark on a journey of self-learning and training. For me, that was Seattle.

Step two: buying the ticket — that was easy.

4. How did you make your first dollar?

When I landed in Seattle, I was looking for a new career path. I wanted to go into business for myself. I was juggling some ideas but making no progress and eating into my savings, living downtown and enjoying myself.

I found a challenge on the internet. It told me to take an idea I was sure would work and put it on Craigslist to see if anyone was actually interested. Martin was the originator of that challenge.

Well, I took him up. I put my tutoring service for classic literature up on Craigslist and braced myself for my first reply. It never happened. That pissed me off. I wasn’t going to go out that easy — so I doubled down. I diversified my tutoring options and got my name out there. Eventually I landed a first client. That client refused to pay me after my first session. He said I didn’t know the material. My quest for my first dollar was not complete. That client ended up sticking with me, and then the company I founded, for over two years.

Here’s my original Craigslist posting.


[Martin’s note: A few readers took part in this challenge many years ago. The goal was to increase your income through freelancing by offering a service online. Justin offered guitar lessons. Adrian started cutting hair. A few other readers worked on different services at that time.]

5. How did you promote your business?

I’ve promoted my business through my customers. I offer a really top-notch service and consistency.

Over time, my name has organically spread around the Seattle area. Market research and relentlessness put me in a situation where I always have a good tutor ready to go when I get a first contact from an interested client. The next obstacle for me is learning and applying basics in online advertising.

[Martin’s note: Finding your first client is often the toughest part. Once you land your first client, you need to put in a 100% effort into satisfying this client. You want your client to give you a referral.]

6. What’s next?

Next for my business is business #2. I don’t see an end to refining and growing my first business but I already can’t wait to break ground in a new industry. I believe in monetizing my hobbies and I see business #1 as paving the way for #2.

I’m spending the time now to optimize my advertising and offer a more attractive product, so that when 2017 comes I am ready to be a player in the seasonal business uptick.

What’s the update one year later?

I sent Theo an email in September (2017) to see how business was going for him. Here’s the official update:

“It’s been crazy over here! I’m still working on my tutoring company. Hiring right now. Last weekend I took a long planned vacation out to Atlanta for Dragoncon (SO FUN) and this weekend I will be hiring down in Portland (I live in Seattle).

I’m also launching a second venture — Go AR/VR. Since day one, I’ve done Pokemon Go Meetup events — some for money, some for free. I see so much potential in building that brand into other virtual organization/event type stuff and so I’ve purchased domains and am working through the business plan.

Finally, my freelance writing is starting to come through. I got a raise at Dope Magazine, and they’ve started giving me some much bigger articles. My last one comes out in October: I smoked 10 strains through 10 pickup games in 10 days to get to the bottom of Basketball and Mary Jane.

All the while I’m doing proactive work to get mentors in my life and push some of the secretarial work and rote tasks off to others, so I can keep my head above water for the foreseeable future.”

Here’s the update on December 5th, 2017:

“I recently faced down a lot of questions about my future. I started my company in 2015 to learn how to run a business, and it worked. Now, we do a lot of good for families that need our help and we inspire children, but I don’t think I will be CEO of StudentCircle forever. I need to push myself and that sometimes means doing something new.

I now employ over 45 people and Winter/Spring is going to be our biggest season yet.

Looking forward: I’ve spent each of the past two summers trying to add massive innovations to the company. Both operations were massive failures (which I learned a lot from and continue to benefit me over and over. I’m so glad I made them.) For once, I’m going to lie low this summer and then, come fall, I am going to make a huge change. I’ll spare you those details, but I will share my plans to step away from the company for some much needed me time, exploring the world on an extended solo trip.

Life has been crazy. I moved out of the city, exited my longtime office space; I’ve been in the gym a ton, my tutoring sessions have been really inspired lately. My students are coming home with A’s, too, and parents are happy. There’s also some deeper things I’m noticing around me. Everywhere I go, people are sharing stories with me about what they’re struggling with in life. I dont know all of these people, and most of them I will never see again, but just a few weeks ago, I found myself moping over how difficult my life feels. Hearing from other people who are struggling with life situations substantially more severe than mine (divorce, death, depression, debt, erectile dysfunction) has been driving me. I do definitely have a lot of pressure and demands on me, but I’m not letting that get me down. My website got hacked last week. If you need a new Rice Cooker, my website is currently a great place to get it. I’ve been drinking a lot more coffee than I am really comfortable with. I forgot to eat the other day. Sometimes I feel like work needs to keep me up till 2am and I also need to get up at 5am so I can get a head start on communication. I’m happy, though. I can’t wait for what’s next.”

How can Theo’s story help you?

We’ve discussed freelancing on here for the last five years. Many readers have turned into successful freelancers.

How many success stories do you need to read before you create your own?

The whole point of this story was to show you that regular people can quit their jobs, move across the country, and change their lives by taking action. I’m so proud of Theo.

What can you take away from this article? There are three key highlights…

1. Decide what it is that you want to do.

What exactly do you want to do?

The following are NOT goals:

  • Have a better life.
  • Make passive income immediately.
  • “Foster relationships.”
  • Be epic.
  • Do epic stuff.

The following are realistic goals:

  • Find your first paying client.
  • Quit your job in 7 months to work on the business.
  • Save up $5k over the next year so that you can work less hours at your job.

What do you want to do?

2. Accept that you don’t need to start some extravagant empire.

“I want to build a popular app. I like to dream to big.”

I get it. We all want to start the next Facebook. However, it’s more important to be realistic with your goals.

You notice a theme with the case studies here?

Farhan started selling shirts. Matt started making tables. You can start your own online business.

None of these case studies are instant rags to riches types of examples. Regular people do cool things all of the time. You don’t need to try to start the next Facebook. Focus on solving problems in your niche in the world.

3. Grow your savings account.

Right now’s the best time to start saving up. Work on your savings account so that you can build a cushion to take on some risks.

You won’t be able to do anything if you always feel like you’re stuck. With some money in the bank, you’ll have the flexibility to make some moves.

Thanks to Theo for sharing his story. I don’t want you to just get inspired. I want you to take action right now. You don’t need permission from anyone. We’re living in the best time period ever. Start now and fix things as you go. This will be more fun than any video game.

“I have far more respect for the person with a single idea who gets there than for the person with a thousand ideas who does nothing.” — Thomas Edison

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