How I am Able to Run 12 Businesses at the Same Time

It was the summer of 2015 and I found myself in between tech startups, five years after releasing my first feature film, getting ready for an interview at Google headquarters, jumping from contract to contract for my technology consulting company, while figuring out my next move. I knew one thing for sure: I wanted to make an impact on the world around me.

Unbeknownst to me, there was a story hidden all around me that was waiting to come out.

Serendipity helped me uncover that story to create the award-winning documentary, The King’s Highway. While engulfed in the history of Philadelphia and having to learn roughly 400 years of American history in just one year, I had to continue managing my main businesses. It was difficult, yet possible because of the fact that I had been doing it for over a decade.

In between tech contracts I found myself helping entrepreneurs with the same methods, tactics and strategies that I had been implementing in my own businesses. It was getting quite repetitive and I sometimes wondered how I could offer these methodologies to a larger audience. That’s when I was approached by Google to be interviewed for a Startup Program Management role at their headquarters in Mountain View, California. On the day of my birthday in 2015, I flew out to Google for a few days to be interviewed by several people. It was an amazing experience, and one thing became clear to me: I was in demand.

Although the job understandably went to a candidate local to Mountain View, I knew that I had something valuable to offer. I just had to figure out a way to make it available to a broader audience. So in between my first production shoots of the documentary and editing the first version of the film, I decided to write all of my methodologies into a book that I published, called Strap on your Boots. I was fortunate enough that I had to wait for the winter to end so that the warmer weather would come in order to begin the second phase of production shoots and final edits for the film. This gave me time to write the book.

The goal of the book was to help entrepreneurs build and scale their business without spending exorbitant amounts of money and months or years of time wasted. I wrote the book in roughly 30 days and then edited it, and had my editor polish it off for me. After sending the book to various university contacts I was asked to create a course called Startup Essentials for the University of Pennsylvania’s Wharton school for their Startup Entrepreneurship Program and then teach that course as an instructor. Again, I had to manage my technology consulting company, the production of The King’s Highway, and now create a course and teach it at Wharton.

I was able to juggle all of these intense projects by managing my time through a calendar, taking ample breaks, constantly doing research, engaging with others, staying organized, and remaining disciplined.

My schedule is extremely flexible, yet the guidelines I give myself are fairly routine. Sometimes I will work eight hours without stopping, other days maybe two hours here, two hours there, and three hours at night. Of course there are the days where I have to work 12 to 14 hours several days in a row. Those are the days that truly drain me. Fortunately, I have the advantage to stay away from the office some days, and work mobile. I can also take a day off pretty much whenever I want.

Everything is in my calendar, and I have an automated scheduler directly on my website so that I do not have to email clients back-and-forth to pick a date. I also try to limit how many meetings I actually accept unless there is an agenda prepared before the conversation so that we can tackle the topics much more efficiently.

I do have a reasonable amount of breaks throughout my day to keep me energized and to unplug from the multitude of projects that I am constantly engaged with. Having a dog helps, as he has a routine for his walks. I also go to the gym three days a week, occasionally do yoga, or just meditate sometimes. Without breaks I would not be as focused and productive. Plus, I find myself coming up with some of my better ideas while away from my desk and free to be one with nature, breathe fresh air, and stay active. That’s when Siri becomes more of a dictaphone rather than a personal assistant. When people say they always have ideas but they lose them, I don’t really understand how that’s possible. With the available technology we have, you shouldn’t be losing anything.

Whether I am managing a development team, film production crew, writing articles, books, or screenplays, working with technology clients, talking to journalists, working on a startup, teaching a course at universities, meeting with organizations and politicians, hosting events, being interviewed in the media, or working with the community around me, I have learned that engaging with others is the best way to learn how to impact the world around you.

For me personally, it has helped me understand how to do (and not do) things, best practices if you will. Of course I still learn on a daily basis, but I’ve gotten pretty good at following best practices for the most part. This has also helped me learn how to choose the right entities to engage with. Collaboration is key when you are trying to accomplish very large goals. By collaborating with amazing people and organizations you’ll find your goals get completed much faster.

Although technology has negative connotations in today’s society, it has made my life much more efficient. For example, I saved roughly 80% of my time writing this article by speaking it to Siri and then editing it later on a word processor. When I can tell a story wherever I am, without the restriction of being tied to a desk, it allows me to write anytime and anywhere. If you are a writer, you might have found yourself at your desk countless times, feeling forced to write a chapter in your book, a scene in your screenplay, or an article for your blog. Many times, you might be blocked, frustrated, tired, or simply unmotivated. This is why I choose Siri for most of my writing. Of course there are limitations, such as when I write a screenplay (Final Draft is King or Queen!). That being said, one of the most efficient ways of multitasking is to leverage the technology that you have at your disposal.

Organization is also very important when it comes to efficiency.

Everything I work on is labeled properly in folders and my several email addresses are categorized and labeled. Most of my businesses and work is available to see online in various digital formats so that I do not have to continually repeat myself and explain what it is I do or what I’m in the middle of working on. It has helped me get to know people quite fast as well, as they can learn about me without having to ask 21 questions when first meeting. That allows us to get to the nuts and bolts of the conversation, real personality, real questions about my true self and theirs. It also allows me to see how I relate to somebody because they’ll be able to tell me stories about themselves after reading some of mine.

Anyone who knows me, knows that I’m a huge proponent of task lists, and regularly adding things to them as well as crossing things off when completing them. This is my own way of keeping myself in check since I am an entrepreneur and my own boss. Somebody has to tell me what to do, and that task falls onto myself. Hence why you must be disciplined more than anything else when you are an entrepreneur. I do look forward to an AI robot assistant one day! Ironically, I actually talk about AI robots in this episode of Xploration Earth 2050, an Emmy nominated show I was featured on many episodes for. One of my many achievements which gives you the wide array of things I do.

Although I have certain deadlines for my technology contracts, launch dates for apps, and specific dates that work better than others for a movie premiere, I have made it my mission to not only do things as quickly as possible, but as simultaneously as possible. Case in point, while I was creating The King’s Highway, writing my startup book, creating the course, teaching it at universities, writing articles for news publications, taking video production jobs, and staying on top of my technology consulting company, I was also hired to write the life story of an 85-year-old woman’s exploits as a student of B.K.S. Iyengar the famous Yoga Guruji.

Also, while working on my film, I found a cool sub-plot in the interviews that piqued my interest. After doing ample research, I wrote a war spy drama screenplay called Whitemarsh, about the true story of America’s first unofficial spy, Lydia Darragh and how she helped General Washington and the Continental Army win the Revolutionary War.

Backtrack to 2009, when I entered the world of mobile app development. Then jumped into Bitcoin a few years later. I ended up selling my Bitcoin and other cryptocurrencies in late 2016 but jumped back in early 2017 when I saw it begin to take off. I began to get bombarded by people looking for help on how to get into cryptocurrency. So I created a website which includes articles and video tutorials to voice my opinions on the crypto space. Over the years, I also created tutorial videos on one of my YouTube channels for all types of industries that is currently being advertised through a third-party publisher. So I always try to schedule time in my calendar to create new content and help people with topics I often get asked for help on.

This while being the cofounder of three tech startups, Instamour I’ve been running for five years as CEO and recently pivoted to release a new version launching soon. RyteCare is an on demand healthcare app of which I am the COO. And InVidMe is a video interaction entertainment app where I’m COO once again. All 3 apps are launching any day.

In between development phases, iterating certain parts of the platforms, and working on everything else I listed above I often times had detailed conversations with a few LA based producers who gave me tips on my writing. After taking everything into account, reading scripts, and honing my craft, I wrote my first spec script. It’s a dramedy called Woodchuck Charlie, about an agoraphobic man who falls in love with his mail woman and has to overcome his fear of the outside world. I’ll soon be pitching this script to producers nationwide after editing it some more.

Most people look at me and say, how the heck did you write a screenplay while working on all of these projects and companies?

The secret is to find gaps in your day that allow you to focus on something else. For example, let’s say you are a single mother with two small children, and it’s their 3PM naptime. This gives you an hour of free time to catch up on a TV show, do your nails, read a book, or just talk to a friend or family member on the phone uninterrupted.

Being that I am single with no kids, when my babies (companies) take a nap, that gives me the opportunity to do something else. Instead of engaging in a personal pastime, I move onto the next business or idea and tackle a piece of it. I continue doing this all day every day, every week, every month. I slowly pick away at each business, while making sure that when one business needs more attention than the other, I focus my efforts on that business.

Also, there are times I’m waiting for developers to provide a new app build, or I’m waiting for responses from people about meetings, initiatives, and other work. So when I’m in a waiting phase, I take advantage of those hours, days, or even weeks and months. So instead of waiting for those gaps to close, I immediately engage in another project, or clean up and update a project or business. This approach allows me to constantly utilize the vast array of skills and talents that I have learned over the years. It not only keeps me on my toes, but it keeps me humble, motivated, busy, engaged, and makes me constantly have to learn new things, keep current skills fresh (or updated), and keep my brain sharp.

The best part of doing it this way is that I am able to help people much more effectively, with less mistakes, and with faster results within a shorter amount of time.

The most often asked question that I get from people that I meet is, “Do you ever sleep?” I always find that funny because I do sleep a minimum of eight hours every single night. My brain naturally tires and wakes up like clockwork, and without an alarm. The reason why I find it funny is that people believe that no human can do the things that I do without sleep (Tesla, Jobs, Einstein anyone?). But in fact the opposite is true.

The secret to how I am able to create as much as I do in such a short amount of time is a couple of things.

  • Speed of execution
  • Amount of knowledge
  • Mastery of several skill sets
  • Ability to multitask

By working with so many people in my career, I have realized that what it might take somebody eight hours to do, or even an entire week, might only take me 15 minutes or in some cases 30 seconds. What might take 10 people to accomplish in one year, I can most likely do in a couple of months. Being an entrepreneur comes second nature to me and is just my daily routine at this point in my life.

While I am not inventing the next spaceship, or solving climate change, I am helping improve the world by using my methodologies to teach as many people as possible, so that they too can take control of their life, make less mistakes, spend less money, and achieve results at a much faster rate than they were able to before. I also have gotten to the point where I’ve been able to dedicate and volunteer some of my free time to a cause greater than myself. Instead of watching my nonexistent children grow up to become adults, I am witnessing my businesses mature into fine-tuned machines of code, services, and tangible offerings to the public for various initiatives, including the history of the United States of America.

While meeting over the past decade with investors for my various companies, a trend was that they always wanted to make sure my teams and I were completely committed to the company I was pitching them for. Over the years, I have found that this is an ineffective use of time. One simple example would be the tech startup that I launched back in 2013, Instamour. At one point we were the leading video dating app in the world, boasting roughly half a million users, and growing at a breakneck speed.

While fundraising in late 2016, we ran out of money which caused us to step back for a bit. My point is not that the company isn’t doing well (because it is). My team and I are about to launch a brand new version after pivoting and developing it over the past year and a half. My point is that instead of putting all of my eggs in one basket, I spread my eggs into various baskets and have found successes in many different ways. So I am not a believer that you must focus all of your energy on just one idea. Especially if you have many good ideas, and you are able to multitask the way that I do. Why not see all of your ideas come to life together and succeed in more ways than one?

Another thing that really helps, is if you are able to learn many different skill sets to hire less consultants, and do more work yourself.

This is definitely one of the ways that I’ve been able accomplish as much as I have, and continue to do so. Not only do I get more work done efficiently, but I waste less time delegating to other people. Sure, I have plenty of people who I work with, teams of developers and employees whom I have to manage, interns who help with certain administrative duties, and teams of people helping me with various initiatives. In the end, most of the harder work falls on me, and it’s that hard work that keeps me productive and motivated. It’s hard to describe the feeling I get when I release a finished product into the world. I suppose it’s akin to a mother giving birth.

These skill sets also save me a ton of money, whereas normally I’d have to pay a consultant or company thousands of dollars (or more) to accomplish certain tasks. Being able to do them by myself means all I’m spending is sweat equity, and not actual cash. One of the advantages of having so many skills and accomplishing so many goals, is that people see you are not a one hit wonder. Take Facebook for example. Mark Zuckerberg notoriously stole the idea (allegedly) behind the platform from the Winklevoss twins. In doing so he set himself up (at least in my opinion), for the fact that he has made his name on only one product: Facebook.

Zuck after he realized he stole Facebook

Has Mark Zuckerberg invented another platform or product that has changed the world? Has Evan Spiegel of Snapchat fame created another product or service since his billion dollar valuation? No. Sure, they keep acquiring companies, but they aren’t building them, they are buying them. You’ll find that most investors, or celebrity entrepreneurs, made their millions from a one hit wonder, and haven’t been able to create anything else in years, if at all. I don’t want to fall into the same category as those entrepreneurs. This is why I have dedicated my life to learning about and creating as many things as possible, and sharing them with the world.

Being a journalist has certainly helped me stay connected to the various industries around me. I focus mainly on writing articles for Technically Philly about the startup culture in Philadelphia, or writing about entrepreneurship and the future on my news blog. I always try to make time to write articles here and there to not only stay connected, but to add my voice to the world of journalism.

My latest endeavor took me by surprise because it was sparked by The King’s Highway. The popularity of the film turned into a movement to spread awareness to and preserve the history of America in Northeast Philadelphia. I am not a historian, but as an entrepreneur I saw a gap in the market. The history of the area wasn’t reaching a mass audience and the plethora of neighborhoods in Philadelphia were suffering because of it. So I set out to change that. Along with a team of gifted individuals we formed The King’s Highway Trust Foundation nonprofit. You can see all of the news and stories about our initiatives here.

The fact that I have control over my schedule, means I’m able to volunteer my time to these historical initiatives and be a part of something greater than myself. Sure, with this lifestyle I’ve had to accept a pay cut. I could be making $250,000 or more in Silicon Valley, or something similar here in Philadelphia. People ask me why I don’t take one of those high paying jobs. Simple. Because I choose freedom over money. Sure, I may not be a millionaire (yet), but I own my time, and have complete freedom over what I do.

One of my favorite quotes by Confucius that I included in my book is, “Choose a job you love, and you will never have to work a day in your life.”

According to that quote, I haven’t worked since I held my last corporate job as the IT Director of Software Implementation of an auto parts company in 2005. Since then I’ve been working as a full time entrepreneur, and will continue to do so, while I help people along the way.​ I suggest you also keep learning, creating, and helping others. If you are one of those people who need help, I’m always a pitch away:

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Jason Sherman

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