From Entrepreneur to CEO Entrepreneurship / Finances / Productivity

When I started my online business, I did everything myself. The planning, programming, graphics design, database management, server maintenance, marketing, customer support, billing, accounting, taxes — everything! Most of it I learned as I went along. It was a lot of work and took every spare moment of my time for several years.

As the business grew, I realized that I didn’t have to do it all myself, and in fact, I couldn’t do it all myself, because there was simply too much for one person to do. I started by hiring a programmer to speed up development, then some customer support help. I still did a lot of programming and support myself, even after I had trained my new staff, but less and less as time went on.

However, giving up control of an aspect of my business to someone I didn’t know (and hadn’t spoken with on the phone, even less met in person) was a difficult thing for me. I felt like I knew my business inside and out, and I believed the mantra, “If you want something done right, you have to do it yourself.” So I kind of micromanaged. I monitored every piece of code my programmer wrote, and every email my support reps sent to my customers. This was my business — my “baby” — and I wasn’t going to let anyone mess it up.

As I hired more programmers and had more customer support emails coming in, it became too much work for me to check up on what each of them was doing every day, especially with my other responsibilities. But by that time, I had come to trust those I hired, and knew they would deliver quality work. In fact, they were doing their jobs better than I ever did. I still had daily communication with each programmer about what they were working on, and still regularly checked up on support issues, but my teams were free to do their tasks however they thought was best, within a few procedural guidelines.

Last month I hired four new programmers (there are now eight total, across all my sites, plus an iPhone dev team) and two new customer support staff (9 total, across all my sites). Trying to stay in touch with this many people, and being the “go-to” guy for everything quickly became more than I was ready to handle. So a couple weeks ago, I decided to step back even further, and hire a Project Manager (promoted from the Support Team) to help manage the programming team and the new features and fixes we’re working on. I also hired a Customer Relations manager (who is also our Marketing Director) to facilitate the Support Team keeping the customers happy.

I already know this was a good decision. These people are doing an incredible job running the business. So many of the tasks I had hesitated with for so long, they’re taking head on, and are setting up systems and processes to improve the quality and efficiency of the teams and the communication between them. They’re keeping their teams happy and productive, making decisions that will improve many aspects of our product and service, advising when to hire and train additional people as needed, and letting me know what things I need to be aware of. I feel like a huge weight has been lifted from my shoulders.

Music Teacher’s Helper has continued to grow well this year. The past three months we’ve had a record number of new signups, and with these management changes, I only see that increasing. It’s exciting to see the growth, and also the enthusiasm of our customers for a product they feel helps them so much in their teaching business.

But where does this put me? Now that I have so much help managing my teams, I no longer feel like the lone entrepreneur running his one man show. I also no longer feel like the micromanaging boss with his fingers into everybody’s business. Instead, I feel like the CEO of a growing company that I’m directing but not necessarily running.

It’s a huge shift for me, making it easier to focus on the big picture; setting the vision, direction, and culture of the company rather than fine tuning the inner details. I’m still interested in the details, but I trust those I’ve hired to take care of them in the way they think is best, and I know they’ll do great. As a CEO, I now have some new skills to learn, and will probably continue making mistakes, as I often have along the way. But I’ll learn, and the business will continue moving forward, not because of me, but because of everyone who works hard to make it happen. Thank you to all who do or have worked at Music Teacher’s Helper!

Brandon is a location independent entrepreneur, musician, worldschooling father, and the principal author of this blog. He's all about reaching his potential and enjoying life to the fullest in each moment.


  1. Jennifer Pearce Says: October 21, 2012 at 12:08 am

    Well, I certainly remember those early days when you practically lived in your office, and I’ve appreciated seeing so much more of you in recent years, especially lately. :) I’m enjoying a more relaxed you who has figured out new ways to relieve your stress, which has been building little by little for quite a while. You had a lot on your shoulders. The timing was definitely right for these changes, and I’m so pleased you’ve been able to find such great helpers along the way. :)

    • Yeah, depending on the task, I can spend hours on the computer stress-free. But some tasks or events, even if I only spend a few minutes on them, can have a big effect on my stress levels. It’s nice to have help with these things and also be more aware of my own limits and attitudes.

  2. It IS amazing how much time you can spend on a business, but you never realize it until you’re able to pull away. Being able to step back away from the “grind” also allows you to see things from a different perspective. We were able to double the profits of one of our businesses within just a couple months after my husband stepped back from taking phone calls and doing all the shipping.

    Congrats on your success!

  3. Great Post! You need to do more post like these. I find them very helpful to see how you approach problems similar to what I see in my business. I probably need to go back through your blog and find posts like this I missed before I was following your blog.

    Thanks again!

    • Thanks Kurt. Some of those older posts need to updated, too, with other things I’ve learned. Maybe I should be posting more of what I’m learning as I go. :) Thanks for the encouragement and good luck with your business.

  4. This has been an amazing transformation – from hardworking do-it-all-yourself entrepreneur to CEO. You never cease to impress and amaze your mother.

    I have handed off a few tasks in my business world to others – but it’s so hard to let go of the control! Especially when a lot of it is creative stuff that is a reflection of me… working to let go of more and trust I can find someone to represent me in a positive way… (chest tightens just thinking about this!)

    • Yes, that’s been a hard thing for me, too. It was first a matter of accepting that things didn’t need to be perfect, and that maybe my idea of perfect wasn’t really perfect, and that others ways could work, too, even if it’s not how I would do it. But when you work with someone for a long time and train them how you like things done, it can be a lot easier to make this shift.

  5. Great post, Brandon, and congratulations on making this transition!

    I think the tendency to micromanage is a common one, one that I fight all the time in various ventures. Imagine being a perfectionist and the leader of a rock band at the same time!

    It’s great that you had the trust and humility to give management control of more specialised tasks to others…and clearly you have reaped the rewards in a major way. That must be an amazing feeling. Congrats!

  6. I too am starting a online venture and found you through tim ferris blog. I found the concept of ‘4hour work week’ absolute non sense. Any one who has ever made it never worked that little unless they put years of work in prior. Good to hear that you’ve made it and even better to hear that my initial assumptions were correct.

  7. Hi Brandon. To get where you are seems like climbing a mountain for me but one that I’m willing to tackle. I think your simple, no bs approach is a great one and one that I’m getting lots of ideas and motivation from. It feels like it’s a very authentic way to succeed. I get the feeling that you still shake your head at how far you’ve come. I’m looking forward to reading the book you write about how your journey. All the best mate and I look forward to reading more.

  8. Hi Brandon.
    What exactly is your internet business?
    Is it based in Bali, or USA for tax purposes?
    I’m wanting to relocated to Bali with a fashion business where I return every now and again to do small scale manufacturing, but don’t know if I would have my tax/banking base in Australia, or to have it based in Bali?

    • My business is It’s an online based in the USA for tax and banking purposes, but our team and customers are all over the world (and we have no physical office). I’m no tax expert, and you’ll probably want to find one to ask these questions to, as there are a lot of factors to consider when deciding where to base your business. Good luck!

  9. We’re considering this same kind of adventure for our family & already have an online based business that could fascilitate our travels IF we can have reliable internet service. Can you please tell me how do you stay technologically connected via wifi & would you have any tips, suggestions or satellite or wifi references you could recommend?

    • Hi Tj, we stay connected online by only booking places that have good wifi. And these days, frankly, most of the world does, unless you’re in some remote area. Sure, sometimes it goes down, or it’s slow. I actually had horrible wifi in San Francisco a couple weeks ago when I was attending a conference (almost non-functional for 3 days at the hotel I was in). I was glad to get back to the small town in Mexico where I had a decent connection. lol. Do your research before booking a place or signing a lease, and you’ll be fine.

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