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Author John Roa: “Success comes with a lot of layers”

“Success” comes with a lot of layers and stipulations. It is not all positive.In business, we are generally only exposed to watered-down exposés on success, that tend to massage out the negatives and always have Cinderella endings. Because we generally have so many people depending on us, that we feel must see us as perfect […]

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“Success” comes with a lot of layers and stipulations. It is not all positive.

In business, we are generally only exposed to watered-down exposés on success, that tend to massage out the negatives and always have Cinderella endings. Because we generally have so many people depending on us, that we feel must see us as perfect and impervious, we struggle to ever come clean about our humanities.

That’s what happened to me. I wanted to be the superhuman young CEO that I thought everyone expected to me. Which led to a slew of issues and challenges, that ultimately almost killed me. But I got out, won the game, and now want to give the “other” perspective on success.


As part of my interview series on the five things you need to know to become a great author, I had the pleasure of interviewing John Roa.

John Roa is an entrepreneur, investor, writer and podcast host. In 2015, he sold his tech company ÄKTA to Salesforce, which is also the subject of his 2020 memoir “A Practical Way To Get Rich … And Die Trying”. He is also the host of The John Roa Show, where he interviews the world’s most successful people about their real lives.


Thank you so much for joining us! Can you share a story about what brought you to this particular career path?

I’ve been an entrepreneur since I was an early teenager. I’ve always loved technology and what it’s able to do. Being a well below average student, I hoped entrepreneurship would be my path to success.

After a few failed attempts, I founded a company in 2010 called ÄKTA. It quickly became one of the fastest-growing companies in America and was eventually acquired by Salesforce in 2015.

This experience was the best and worst of my life. I became successful in most measurable ways, but I also paid a big price, in the form of mental health issues, substance abuse, the party lifestyle, etc., which was very hard to manage while running this fast-growing company.

Thankfully, I survived and am now able to talk about the experience and lessons.

Can you share the most interesting story that occurred to you in the course of your career?

That’s hard to quantify. But here’s one that is fun and taught a lot of lessons.

Jimmy Chamberlin, one of the most famous musicians of all time as the drummer of the Smashing Pumpkins, was building a tech company and we were pitching him our services. As a former drummer, I was starstruck.

We had a good convo, and then upon seeing the ping-pong table in our office, he challenged me to a game, saying he is quite good. I knew I should let the client win, but I am too competitive. And I beat his ass. That confidence and conviction also won his respect, and we’ve been great friends ever since.

What was the biggest challenge you faced in your journey to becoming an author? How did you overcome it? Can you share a story about that that other aspiring writers can learn from?

I am not sure I think of myself as an “author”. I failed high school English and until I wrote this book, I had barely written more than emails and business plans.

The idea for the memoir came from friends encouraging me to tell my story. I had the time, so one day I just started writing. It felt good, and my buddy was enjoying reading it, but it never felt like I was writing a real book. I took breaks when it got tough, wrote it across 12 months and 3 countries, and even when it was finished, had no idea what to do with it.

My network stepped up and pretty soon an agent was getting it in front of major publishers. I was as overjoyed and surprised as anyone when there was interest, and it finally found the perfect home at Viking (Penguin Random House).

So, I guess the challenge and lesson therein is that I never had confidence in my ability to write or get a book published, but still had to give it a shot and look what happened. Even if you don’t believe you can do something, there’s rarely a downside in giving it a go.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This interview would never end if I tried to list them all. I have made every single mistake you can in business.

I am not sure if any of them were necessarily “funny” though. There were many that were ridiculous … like printing the wrong phone number of tens of thousands of business cards or having to pitch by whispering in a client’s ear once, due to not being “allowed” to talk in her office.

I think with every mistake comes a basic lesson: don’t repeat the mistake.

What are some of the most interesting or exciting projects you are working on now?

My memoir A Practical Way to Get Rich … and Die Trying launches on Sept. 8, so that is by far the most exciting. That is three years of work and energy into a very personal project that I couldn’t be more exciting for. My podcast The John Roa Show has also been really exciting and am looking forward to continuing that.

I have a couple of other entrepreneurial projects on the horizon that I can’t speak about quite yet, but it’s exciting to think about jumping back into starting companies.

Can you share the most interesting story that you shared in your book?

I talk a lot about Imposter Syndrome in the book. When I first started the company, I felt like a fraud, as I was a non-designer starting a design agency. I had absolutely no clue what I was doing but did it anyway. Then the company started to work and grow, and at times I would feel like an expert and a qualified entrepreneur who deserved the success, and then I would flip flop back to feeling like a fraud, and like I was going to get “caught” in the act.

I realized years later that this is an incredibly common affliction amongst not just entrepreneurs but anyone who is ambitious and excels at their craft. Athletes, musicians, lawyers, politicians … you name it. It can be difficult to get out of your own head and realize you actually are qualified, and you do deserve what you achieve.

It can be a very scary topic to talk about in the moment, however, which is why we only regularly hear about it in retrospect. This is something I think needs to change, so I try to talk about it with every guest I have on my podcast and speak as much as I can from a personal perspective when I experience it, even to this day.

What is the main empowering lesson you want your readers to take away after finishing your book?

“Success” comes with a lot of layers and stipulations. It is not all positive.

In business, we are generally only exposed to watered-down exposés on success, that tend to massage out the negatives and always have Cinderella endings. Because we generally have so many people depending on us, that we feel must see us as perfect and impervious, we struggle to ever come clean about our humanities.

That’s what happened to me. I wanted to be the superhuman young CEO that I thought everyone expected to me. Which led to a slew of issues and challenges, that ultimately almost killed me. But I got out, won the game, and now want to give the “other” perspective on success.

Based on your experience, what are the “5 Things You Need to Know to Become a Great Author”? Please share a story or example for each.

I am not yet a great author… so, I cannot answer that.

What is the one habit you believe contributed the most to you becoming a great writer? (i.e. perseverance, discipline, play, craft study) Can you share a story or example?

Similar to my answer above… I think it is TBD if I am a great writer or not.

When it comes to the craft… what worked for me was to write the same way I talk. I have been told I am a capable storyteller, so I wrote the words on paper in the exact way I would recite them out loud if I was really trying to get someone engaged in my story. I didn’t worry about fancy words or sentence structure. For me, it was really trying to craft an engaging narrative that would be fun and easy to digest.

Which literature do you draw inspiration from? Why?

My favorite author is Chuck Palahniuk, who famously wrote Fight Club. I think he is one of the most exciting and engaging storytellers of my generation, and a lot of my style and cadence is a result of studying his books.

You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

You know, I used to think I could change the world. I don’t anymore. Now, I think I can only change my world, which I hope in turn gets someone to change their world, and so-on.

My focus today is on being a great person, friend, brother, son and uncle. I try to help people whenever I can, in any ways that I can, and when asked, share whatever wisdom or advice that might be helpful.

How can our readers follow you on social media?

Instagram / Twitter @johnroa

Thank you so much for this. This was very inspiring!

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