jonathan bailor employee to entrepreneur

Former Microsoft Program Manager Shares His Employee to Entrepreneur Journey

Why is there so much talk about “young” entrepreneurs when the most successful companies (the top 0.1% based on growth of the first five years) are founded by individuals at the average age of 45? Call me a cranky 38-year-old, but the data seems to prove what seems like common sense: It takes a lot of knowledge, experience and maturity to build a successful company. Of course, anything is possible, but let’s talk about why gaining experience in the workforce first can set you up to successfully transition later in life from full-time employee to entrepreneur and radically increase your chances of building a successful company. 

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Here’s how I formulated my employee to entrepreneur journey, and how you can follow a similar path to launch a successful startup:

Set yourself up for success by working in the most challenging “corporate” job you can get

As a future entrepreneur, it’s crucial that you spend most of your 20s and perhaps some of your 30s working in the most demanding and most successful company you can find. By choosing an employer in the industry in which you want to be an entrepreneur, this gives you invaluable on-the-job training in your field.

Although you may feel the temptation to go out and start your own business, to shake up the system like the young prodigies you’ve read about, it is exceedingly difficult to shake up a system that you don’t understand; therefore, you need to get into the system first. And, just because you are good at your profession, it doesn’t necessarily correlate to you becoming a successful entrepreneur and running a profitable business.

Having a job teaches the skills you need like collaboration, professionalism and communication to then go out on your own and run your own business.

Related: WJR Business Beat with Jeff Sloan: Entrepreneurial Success by Age Demographics

Get the value of real life work experience before building your entrepreneurial venture

Imagine trying to put a puzzle together without seeing the picture on the box. It’s really hard to build something if you have no idea what that something looks like, and it’s even harder to build a company that works if you’ve never seen one that works. Similarly, aspiring entrepreneurs need to surround themselves with excellence to become excellent.

Fresh out of college in my early 20s, I became an engineer at Microsoft. As an employee, I gained the most valuable experience of my life when it came to the planning, developing and launching of products, and I was able to learn what worked. Along the way of registering 25 patents, there were failed attempts and missteps — which you will have in your entrepreneurial journey, too — but, by working at a corporation like Microsoft, it allowed me to explore intrapreneurship without going bankrupt or ruining my credit.

Additionally, I was also able to work with some of the most competent business professionals in the industry and learn from them for free. An invaluable opportunity, this also allowed me to have built-in mentors and start building a network for when I went out on my own. 

Begin testing your idea while still employed full-time

Always passionate about health and wellness since my teenage years, it was while I was at Microsoft in my 20s that I spent all of my nights and weekends collaborating with top doctors and researchers to analyze more than 10,000 pages of academic research related to diet, exercise and weight loss. Eventually, after being at Microsoft for about seven years, this research became my first self-published book, “The Smarter Science of Slim,” and later, the single largest scientific analysis of health and fitness ever conducted.

While essentially having two jobs at one time, this also meant I had minimal financial risk while I was pursuing my “passion project.” Saving every penny you can while working for someone else is extremely important for planning to start your own entrepreneurial venture, as it allows you to be better prepared to bootstrap your startup. This way, when you do set out to be your own boss you can avoid having more bosses who go by a different name: investors.

While I worked at Microsoft, I drove a broken down 1998 Toyota Camry with no driver’s side door handle. Why? Because I knew I wanted to do something else with my money later.

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Prove your business concept

As you approach the end of your 20s, this is the time to begin to test your business model by figuring out a way to prove your concept while you’re still employed. Remember, you don’t need a product to prove a business concept. Instead, you can research the potential product, see if there’s a market for it and go from there.

For me, this was when my self-published book caught the eye of a literary agent who approached a publisher that turned it into The New York Times best-selling book, “The Calorie Myth.”

I didn’t leave Microsoft and lose my full-time income stream until I basically had to because my side hustle became too successful not to turn into a full-time gig helping others with their health struggles. I also never really left. My exit included hugs and an open door to come back. I even went back to Microsoft the year I launched my business as a guest speaker and spoke to company executives and employees about “The Calorie Myth.” Talk about having the safety net you need to really put your neck out there and not be afraid to fail. I appreciate you, Bill. 

Start your own business

Once you have proven your concept and essentially have a successful startup, then it’s time to officially start it. By then, you’ll have the money to self-fund it, the skills and experience to crush it, and the network to enable it. You’ll have everything you didn’t have in your early 20s.

Honestly, putting in tens of thousands of hours at Microsoft during my 20s is the only reason I’ve been successful as an entrepreneur. I am eternally grateful to have had the opportunity to witness and have been a part of the majesty that is one of the most excellent companies ever.

Like most things in life, the truth is the opposite of what most people think. That’s why Mark Twain said, “Whenever you find yourself on the side of the majority, it is time to pause and reflect.”

Get that money. Develop those skills. Earn that network. Eat a piece of humble pie. And enjoy a successful startup in your third or fourth decade rather than failing in your 20s and being forced into the rat race.

Anything is possible with the right foundation, and hopefully these tips help make your entrepreneurial venture more probable. I hope you do everything in your power to experience something similar. It’s worth it, I promise.

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