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Adam Bertram of Adam the Automator: “Focus on passive income opportunities above everything”

Focus on passive income opportunities above everything. Put in the time now to reap the rewards over time. It’ll add up. Imagine going to sleep and knowing your business is making money for you; that’s what passive income is. Passive income is building something and getting paid over time. Think ad revenue on a blog post […]

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Focus on passive income opportunities above everything. Put in the time now to reap the rewards over time. It’ll add up.

Imagine going to sleep and knowing your business is making money for you; that’s what passive income is. Passive income is building something and getting paid over time. Think ad revenue on a blog post you wrote last month, book royalties you wrote a few years ago, or interest in a savings account. That’s all passive income.

Early on, I was focused on making money and getting paid right away. I was too impatient. Looking back, I should have started to focus on building assets that pay over the years rather than all at once.

Just like investing, the earlier you start building streams of passive income, the better off you’ll be down the road.


Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Adam Bertram.

Adam Bertram is a 20+ year veteran of information technology and an experienced online business professional. He’s a successful blogger and owner of adamtheautomator.com, and actionblogger.com, consultant, online trainer, published author and freelance writer for dozens of publications. You can find Adam on Twitter at @adbertram.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I was born in 1980 and grew up in a tiny town of around 1,000 people in southern Indiana. My dad was an elementary school gym teacher, and my mom was a housewife, occasional substitute teacher, and owned a small crafting business in town. Looking back, we were probably considered middle class back then.

During the eighties, my family bought their first computer. I believe it was an IBM 8088 with dual disk drives and no hard drive. I was only five years old, but for whatever reason, I was fascinated with it. My mom told me I took to it like a moth to a flame.

I’d spend hours on it just learning. While most kids may have immediately tried to play games on it, I was more interested in learning how it worked. I would spend countless hours trying to make it faster, learn how to code on it, run numerous utilities and play some games. And this was before we even got Internet access!

Fast-forward to the early nineties when we got our first computer that would run Windows 3.11. At the time, I wasn’t a computer expert by any means, but I loved to soak up knowledge about computers.

Whenever the computer would break (or when I would break it), my parents would always call a local guy, Greg, to come and fix it for 20 dollars. Greg was our small-town computer guru that always knew how to fix things. Greg was a small-town guy you’d expect more in the local bar than at the helm of a personal computer.

Greg would come over and begin looking at the computer while this scrawny 12-year-old would be hovering over him, asking him 100 questions. Greg would always smile and answer every question I had. I learned a lot from that man.

During this time, I learned it’s OK to break things as long as you can fix them. If you try something and fail at it, you will always learn from the experience. Luckily, I never broke anything of significant importance, so my parents let me slide.

Over the years, between school, friends, and some sports, I’d still use my computer almost daily. In the mid-nineties, we finally got a dial-up Internet connection. Talk about excitement! I can still hear that familiar beeping and booping of the modem connecting in my head to this day.

Since then, computers and technology have been in my bloodstream. I graduated from a local university in 2004 with a degree in Computer Science and started my IT career.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I can’t pick just one quote, so I’ll give you two:

Rules are for the guidance of wise men and the obedience of fools. — Harry Day (Royal Flying Corps WW1 Fighter Ace)

It’s better to beg for forgiveness than to ask for permission — Admiral Grace Hopper (US Naval Officer and Computer Programmer)

You can probably tell where I’m going with these quotes and the kind of person I’ve grown up to be. I’m a “do first and ask questions later” kind of independent go-getter. These quotes represent my core belief that we as human beings should prioritize solving problems, giving back, and ultimately making the world a better place without delay. No questions, no bureaucracy, just starting.

We shouldn’t just wait around for a boss to tell us to do something or ask for permission before we embark on some audacious project. Just do it!

I also believe rules exist to guide us, not dictate our behavior. We should all think past the limitations and what their intentions are instead of blindly following them. We need to think first and question situations that prevent us from achieving what we set out to do.

This mentality has helped me succeed in my career many times but has also led to some less-than-expected downtimes. I don’t recommend quitting your job the same day your wife is having your second child to build your first startup, for example.

How would your best friend describe you?

If I were to guess, it’d probably be independent, laid back on issues that do not interest him but extremely strong-willed and passionate about the things that do.

A guy that follows his interests wherever they may lead and with love for his family but would never express it publicly.

Someone who is so laser-focused on specific issues and projects sometimes fails at ordinary, everyday things.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much?

1.) Follow your interests and passion.

You have to enjoy what you’re doing to be successful at anything. Sure, some people hate their jobs and make millions of dollars, but money doesn’t equate to success. ‘Success’ is happiness that sometimes comes with the added perk of money and fame.

Once I realized that my family and I could survive from self-employment income vs. a regular paycheck, my career took off.

2.) A laser focus on your goals.

Some, my wife included, have called me a workaholic before, but it’s a label I never accepted. To me, I was just living, doing what I enjoyed doing. I had a focus on achieving specific career goals and followed them for however long it took.

Although, over the years, the 70 hr/week schedules would soon get old for myself and my family. But, if I hadn’t put that much time in, we wouldn’t be in the position we are today.

I’m getting to the point where I can finally slow down.

3.) Doing first and thinking later.

If you genuinely believe something will work, try it. If you know in your heart the action you’re about to take is right, take it. Through your experience and intuition, you genuinely believe something will succeed; just start.

You will take a financial and time risk but if you think it’s worth it now, start right now. You can always iron out the details as you’re moving.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I started my career in 1998 as a college freshman working as a university student worker making 6 dollars/hr. I was thankful to get the job at such a young age, which would provide me with tons of experience.

As time went on, my experience grew, and my interests shifted. I would go from a computer technician to Internet customer service support for a local ISP, system administrator, network administrator, and systems consultant. If all of those titles sound familiar, they are. Every single one of them was in IT in some manner.

Throughout this first chapter in my career, I was your typical employee, working 9–5, quitting one job to move to another with better pay, enjoying my 2–4 weeks of vacation/year, and taking advantage of the excellent health insurance.

I learned a lot during this first chapter of my career and got a ton of experience. After all, we’re probably talking ten years or so.

Until 2008, I didn’t know what it was like to forge your own trail, to feel the thrill of making your first dollar all on your own, and not to be burdened by someone else’s rules. I didn’t know the first thing about being an entrepreneur.

And how did you “reinvent yourself” in your Second Chapter?

In 2008, I started my first business; selling used books online. It was a side hustle where I poured in hours in the evenings and weekends after work.

I loved it. I loved the freedom to run it however I pleased, to be directly responsible for its success and failures, and know that I was building something with my own hands that I owned. I wasn’t doing this for anyone else but me, and it was invigorating.

That endeavor would soon turn into a healthy six-figure business on the side. I could support myself and my family through a job pay cut and the birth of our first child.

But it was hard. Really hard. And it was barely generating a profit, so in 2014, I closed it. But this business sparked another interest of mine I never knew I had; creating online content and teaching people.

During that time, I had started another business; this time, it was strictly online, teaching people with a blog how to build a business just like I was; selling used books.

It was through my experience with that initial blog was why I created a second blog called adamtheautomator.com. This time, I started a blog about technology, something I had lots of experience in. That second blog is what got me introduced to online technical communities, creating online training courses, becoming a freelance tech writer and a published author, speaking at conferences, participating in vendor webinars, being interviewed on podcasts, and more.

My tech career set the foundation of was what to become my career in tech content.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

Although I had different side hustles moonlighting around my job, the most significant event that I went through was when I decided to quit my job for the first time.

As any full-timer gone self-employed person will tell you, it’s a refreshing and terrifying experience. I had flirted with creating content for a long time, but this was the first time I had pulled the safety net out.

I quit my job because I finally realized all of my side income had surpassed my full-time income. I had six months’ worth of savings in the bank, the blessing from my wife, and off I went. To fail at my first startup and get another job again.

I had strayed from creating content purely on my own to building my first startup with no real plan. I started it, had a blast building it up to ultimately find out that I’m terrible at making money at it.

It took two years of 70-hour weeks, arguments with my wife, and stress about paying bills to finally call it quits and get another job.

Until after only one month at this new job, I finally realized I’m an entrepreneur, and there was no way I could have another job. I wanted to create content for others for myself and would never go back to a regular IT day job.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that, and how did you ultimately overcome the barriers to help manifest those powers?

It was when I would write on my first blog teaching people how to sell used books online. I would always get comments from people about how clear my writing was and how easy my instructions were to understand.

For me, I was just writing. I had no formal training of any kind nor any experience writing for others. I just wrote how I talked, and somehow it came out legible.

I enjoyed writing and still do. It was a medium I was comfortable with. I was, and still am a major introvert. I’ve created video courses, spoke at conferences, participating in webinars and podcasts, but I’m always anxious.

Writing is soothing to me. It lets me collect my thoughts before I communicate.

There are no barriers to writing and online content-creation these days. You can start a blog, a YouTube channel, or build a course for free. You don’t need any capital to become an influencer, and millions of people can discover your content instantly.

Now, if you want to start generating any amount of sizeable income from creating content online, that’s a story for another day.

How are things going with this new initiative?

Extremely well. I may not be a millionaire (yet), but I can now wake up whenever I want, work on whatever I want, and know my family and I will be just fine.

I’m now making enough passive income to support myself and my family. As I continue to invest time, come up with new ideas and continue building content, that hill I’ve been pushing this boulder up is starting to become a little less steep.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve had a few mentors over the years but looking back, if it weren’t for my parents allowing me to experiment and break things as a kid, I wouldn’t be here. I don’t think I would have had the passion that I do for technology if I was forced to color in the lines my whole life.

My parents were not strict by any means and typically allowed me to follow whatever kind of creative idea I had next.

My mom had a small craft store in my town growing up with an old 386 computer she processed inventory with. This computer was newer than the one we had at home, so I’d take every chance I could get playing with it.

One day, I was playing on the computer and broke it somehow where it wouldn’t boot up. After hours of trying to fix it, I was out of ideas. There was no Google to help me! I eventually told my mom and expected the worst.

To my surprise, she was a bit aggravated but not angry. Instead, she just called up our local computer guru, Greg, and he came right over. He was able to fix her computer, and I learned how to fix it next time.

When it came to computers, my parents always let me be, even if it meant screwing up a vital business computer! Looking back, I think they realized it was an area I was interested in and wanted to encourage me to learn more.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

Yes. One moment I can see clearly was when I realized I couldn’t make enough money with my startup company to support my family.

I’ve been an engineer for years. I can build just about anything, but when it comes to sales, marketing, and people management, I will fall flat every time. I learned this the hard way with my first company.

This company employed other IT professionals, and me creating short, how-to training videos for other IT professionals. I had founded the company, and it was slowly catching traction, but it wasn’t making a dime. I had no other income at the time and was burning through my savings.

I knew I disliked sales, marketing, and managing people going into it, but I thought I could make it work. To make sales, I had to talk to companies and sell them on why they should pay for videos. I had to develop ideas on how to monetize the videos with ads, sponsors; I didn’t know.

Even if I did manage to find a sponsor, I then had to find someone to create the video (managing people), which was sometimes a chore. I soon realized that not everyone is as passionate about your company as you are.

The company never made money, and I ended up selling it at a major loss.

I don’t think I can overcome this limiting belief in myself; it’s a personality trait. It’s in my DNA. I now focus on outsourcing those tasks, though, as much as possible or not getting into that situation again.

I’m a big believer in working on strengths and outsourcing weakness. Nowadays, I would never start a company like that again unless I had a trusted co-founder that complemented my personality to handle those areas I’ll never be great at.

I’ve learned that when starting a company with the expectation of needing others’ help to make it work, I will fail every time.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I’m the complete opposite, probably to my detriment. But then again, I never will set out to build a multi-million dollar company either. My goal in life is to create a lifestyle business; I want to make a business that puts my small dent in the universe and will support myself and my family.

I’ve always set out to be a solopreneur, blazing my own trail. It’s my personality, and it’s what I enjoy. I’ve gotten some advice and support over the years that have helped me, but it hasn’t changed my initial trajectory.

I usually follow my own path and get opinions along the way.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Definitely. I was scared to death when I quit my job to work on my own for the first time. I recorded a YouTube video about it here.

At some point, you just know. Second chapters in your career don’t come out of nowhere; it is a slow, methodical process. At some point, you just know. When that times comes, your identity changes. You begin thinking of yourself as Second Chapter Adam vs. First Chapter Adam.

When someone asks what you do, if you instinctively mention your Second Chapter, you’ve moved on mentally.

I got out of my comfort zone by repeatedly started projects for others that I had no experience with. I used others to hold me accountable. I’d sign up to build online courses, begrudgingly agreed to write a book and agree to speak at conferences.

I knew I wanted to get to that Second Chapter but I wasn’t sure if I had the discipline to do it myself. I hedged my bets and agreed to take on tasks that I knew I needed to get better at. I had to accomplish these tasks otherwise I’d be letting a client down and risk losing money.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

1.) You don’t need to “lead an organization” like how it sounds to be a successful entrepreneur.

Many people think the definition of an entrepreneur is founding companies, talking to venture capitalists, going public, and employing people. I thought this years ago, and it’s not true.

Anyone with enough persistence, desire, and problem-solving skills can build a lifestyle business that will support you and your family.

My business generates around 250K dollars/year now. I have no employees and only a handful of contractors. It’s never going to exceed even 1M dollars/year, and I don’t expect it to. But I own 100% of my business and can work whenever and wherever I want. I have no meetings, no bosses, and little stress.

Side note: Technically, I trimmed my bosses down to one now; my wife, Miranda.

2.) You can’t hurry success. Be patient. It may be years before you’ll get any traction.

I have ADHD and am notoriously impatient. I want to climb Mt. Everest in 30 minutes and learn fluent German in five days. I’m impulsive and, for some reason, cannot come to the realization I can’t see results from my efforts immediately. Success takes time and may not even come at all.

A few years after starting my second blog, I started displaying Adsense ads. I thought it’d take a few months, but I’d soon be making thousands of dollars per month. I made a grand total of 100 dollars in those first three months. I nearly gave up.

I kept writing blog posts and trying to promote the blog wherever I could. After researching ad networks, I came across other ad networks that were supposed to pay a lot more, so I tried one. My traffic was higher then because I continued to write posts and the ads delivered something like 50x what I was getting. I was ecstatic!

Since then, I’ve moved ad networks again, recruited writers on my blog, and it’s generating about 450x what it was during my first few months.

3.) You can build a successful business with just the current knowledge in your head.

Information is valuable. You don’t need a physical or online store to build a successful business; you just need information people want to know.

I was in IT for 15 years. I learned a lot. It turns out there were many others out there that wanted to know what I knew. I’ve since turned that into a business, sharing my knowledge with a blog monetizing with ads and sponsors.

I’ve created over a dozen online training courses and written a few books. If you have a skill that others want to learn, start writing, recording, and building your own products.

4.) You don’t need a full-time job to lead a fulfilling and successful life.

Growing up, my friends and family were all employees; everyone had a job. It’s just what you did. I knew no different. It wasn’t until I sold my first used books on Amazon that I realized that I could generate money independently. I didn’t need a paycheck from an employer.

In 2019, after a failed startup, I took a job with a great company with great people. After only a month, I quit. Why? Because I realized I was an entrepreneur and couldn’t go back to a job.

It took nearly 25 years for me to fully-realize I just don’t fit with full-time jobs. I wish I would have come to that revelation a whole lot sooner.

I wish I would have known an online entrepreneur long ago that would have convinced me I don’t need a full-time job to have a successful career.

5.) Focus on passive income opportunities above everything. Put in the time now to reap the rewards over time. It’ll add up.

Imagine going to sleep and knowing your business is making money for you; that’s what passive income is. Passive income is building something and getting paid over time. Think ad revenue on a blog post you wrote last month, book royalties you wrote a few years ago, or interest in a savings account. That’s all passive income.

Early on, I was focused on making money and getting paid right away. I was too impatient. Looking back, I should have started to focus on building assets that pay over the years rather than all at once.

Just like investing, the earlier you start building streams of passive income, the better off you’ll be down the road.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I’m moving more away from the tech side of things and more towards pure online content-creation at this point in my career. There are millions of people out there that collectively have a lot of knowledge.

I wish more people would share their knowledge with the world through the Internet, conferences, groups, meetups, etc.

I’d love to inspire others to start a blog, a social media account, a user group, or a website full of interesting information.

The web is full of people looking for information, but there is too much content written by people that have just done the research. There are too many websites out there looking for clicks to make money. They have no experience. Their information is outdated, missing all of those tidbits of knowledge an experienced person would know, or wrong entirely.

We need more gardeners showing us how to plant flowers, investment bankers helping us make wise investment decisions, and mechanics teaching us how to fix a car.

What do you want to be remembered for the most?

I don’t need to be remembered; it is my work that needs to endure. Like a how-to article with no byline, I want my content to help others without regard for the author.

After all, it is not who helps, but how.

How can our readers further follow your work online?

You can find my work on my tech blog at adamtheautomator.com, my blog where I share content-building and lifestyle information at actionblogger.com, or follow or DM me on Twitter @adbertram.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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