Interview with a Barefoot Writer: Ryan Levesque

Photo of author, CEO, and marketing expert Ryan Levesque
Ryan Levesque

“You don’t have to get it perfect; you just have to get it going.
The best time to get it going is right now, right here, today.”

—Ryan Levesque, author, CEO, and marketing expert

The thing most captivating about a conversation with Ryan Levesque is his unabashed enthusiasm. And I’ll add that it’s not just enthusiasm for his own story and successful marketing system. It’s enthusiasm for the way life fits together when you work hard enough to create a business you’re proud of — where you get to spend more time with your children and spouse … where you honor your parents and the teachers who helped you realize big goals … where you’re able to travel to new places and have eye-opening adventures.

If I weren’t already enjoying life as a Barefoot Writer, chatting with Ryan definitely would have prompted me to tackle my writing goals with unwavering energy.

Indeed, Ryan has helped countless individuals articulate and achieve their business goals. He is the CEO of The ASK Method® Company and author of the #1 National Best-Selling book, Ask. Ryan’s book was featured by Inc. Magazine as their #1 Marketing Book of the Year as well as by Entrepreneur Magazine as their #2 Must-Read Book.

And thanks to his inquisitive mind and forays into other businesses, he speaks Mandarin, knows a hefty amount about orchids, and can teach anyone how to make jewelry out of Scrabble tile.

I spoke with Ryan from his home in Austin, Texas, where he lives with his wife and two sons. I hope you enjoy getting to know his story better. Pay close attention to the one thing he’d do differently if he could start again, which mantra he wears daily on a bracelet, why he decided to upend his “mystery existence,” and the reason he got a little emotional during our chat.

You’ve had some major wake-up calls in the last few years — including a life-threatening diagnosis that had you days away from slipping into a coma. And we’ll get to that, but first, take me back … Where were you in your business before those turning points?

The reason I started my own business — and maybe people will be able to relate to this — is that I realized I was living my life in a box. I was taking public transportation in a box to my office. I’d get to my cubicle, and I’d spend my day in a box. I was like, “I can’t spend the rest of my life living in a box like this.”

I was working in the most boring of industries: insurance. I saw my boss, who was very successful in our industry, and I saw my future, and I said, “I don’t want that to be my future. I don’t want that to be my life.”

My initial goal when I first started my business was simply to make $10,000 a month. That was my thing. I thought, If I can make $10,000 a month working from home earning passive income, selling products online, why would I work another day of my life? I figured my wife and I would live a simple little lifestyle. We’d pay our bills and just live a chill life, living the four-hour workweek. The dream, right?


That was my initial goal. I struggled at first like so many of us do and tried a whole bunch of different things, and nothing seemed to work. Then I had my first little success in a random, obscure market teaching people how to make Scrabble-tile jewelry on Etsy. It was the most obscure market, but it was the first thing that we got some success with, bringing in $8,000 a month. But then I realized the problem of going into a fad business. That business went from $8,000 a month to zero.

Then I launched another business, this time in the orchid-care space. I took that business from nothing to $25,000 a month in 18 months. I just started going down this path of launching these little niche businesses in market after market.

A few marketers and CEOs got wind of what I was doing, and they asked me if I could do what I was doing for myself for them. I started doing that, and before I knew it, I was in 23 different markets.

I had this nice little lifestyle business that was making good money. I was in charge of my life and doing what I wanted to do and all that good stuff. Then something happened: My son was born. My life completely changed like it does for everyone who becomes a parent for the first time.

And shortly after he was born, I started losing a lot of weight. I was tired all the time, and my wife said, “Man up. You’re a dad now. You’ve got to do double duty.”

But there was something much more serious going on …

It turns out my organs were shutting down, and I’d fallen into a state known as DKA, diabetic ketoacidosis. Right now, I weigh about 185 pounds. But during that time, I dropped down to 132 pounds. I lost over 50 pounds. I looked like I could be in The Walking Dead. I was super-skinny, tired all the time. The reason why we discovered I was an undiagnosed Type I diabetic is that I applied for life insurance, and my life insurance application was denied because my blood tests were off the charts.


I got rushed to the emergency room. The doctor said I was days from slipping away into a coma.

Oh my gosh.

When that happens, you really come to terms with your own mortality. I was a dad. My son was about 6 months old. I’d just turned 30, and I had this moment where my priorities really shifted. I said, “I’ve built this nice little lifestyle business. I’ve figured it out. I don’t think I’m ever going to have to work at another job ever. But is this what I was put on the planet to do?”

Maybe we all have in the back of our minds, Someday I’m going to do this. “Well,” I said, “someday is now. This is a warning. Ryan, you need to change something.” At the time, nobody knew who I was. I’d been hiding behind a computer screen like many of us introverted writer-type people do.

Yep. Guilty.

Exactly. I had all these pendings and all these businesses. There were no photographs, no videos, nothing. I just had this nice little mystery existence. Nobody knew who I was, and I said, “I think I can make a much bigger impact in the world. What I’m going to do is what I think I was put in this world to do, which is to teach. I’m going to teach people how I did it. I’m going to show exactly how I did it, how I generated $130 million in sales, how I generated 4.2 million email subscribers, how I built businesses in 23 different markets over what was almost a decade. I’m going to teach it. The first step to that is writing a book.”

And that’s when you decided to write Ask.

Yes. The rest is history.

How did you make time to write the book? That’s a pretty big undertaking, and you were a new parent along with running multiple businesses and learning to live with your new diagnosis.

A couple of things … Definitely had to make some difficult decisions where my wife and I decided together to close some things down. I had to cut back. I was in 23 different markets. If it sounds exhausting hearing me say that, it was exhausting. I was pushing myself too far. That’s really what it came down to. I was pushing my body too far, and I said, “I need to scale this back a little bit, but at the same time, I still have something inside of me. I want to make an impact in a really big way.” So we scaled back. I shut down half a dozen of the smallest businesses.

And when it came to writing the book, I’ll tell you — as a first-time author, I made every mistake in the book. I tell people, “It’s a good thing you’re only a first-time author once.” I did it so wrong. I didn’t give enough time. I worked with a ghostwriter, so the first version of the book sounded like a Sex and the City novel. I had to just tear it up and throw it away and start over. It was so bad. I laugh now, but I think it’s amazing the book has sold as many copies as it has with all the mistakes I made along the way.

What was the biggest lesson you took from that experience?

I think for a lot of the entrepreneurs and aspiring entrepreneurs I work with, the thing that holds them back more than anything else is this fear of failure, this paralysis around doing it wrong, like we’re back in school and someone’s going to say, “Oh, you did it the wrong way.”


My mantra — I have it on a bracelet if you could see my wrist right now, and it’s something I teach all my students. It’s like I’m trying to inject an idea virus into their brain, and the idea virus is this: You don’t have to get it perfect; you just have to get it going.

Anytime you find yourself facing resistance — maybe making that leap from the full-time job that you have now to becoming a writer, to taking on a new project, or investing in yourself and moving forward in your business — just remember this: You don’t have to get it perfect; you just have to get it going. The best time to get it going is right now, right here, today.

Amen to that. Now, you said you used a ghostwriter to write your book. One thing that holds a lot of our writers back is the misconception that they should do everything themselves. How did you come to use a ghostwriter for your book? Do you think it took more confidence on your end? More planning?

Great question. Something I’m often asked when I do interviews is “Ryan, what’s the one thing that you would do differently in your career or your business if you had to do it all over again, knowing what you now know?”

I say I really don’t have any regrets about anything I’ve done. Every mistake, every failure, is a part of the learning process, and it makes you who you are.


But there is one thing I would do very differently, and that’s this: I waited way too long in my business to hire. I tried doing everything on my own for way too long.

It’s embarrassing for me to tell you how long my wife and I were packaging up orchid books in our orchid business, sitting on the floor of our living room with Netflix on in the background, with takeout on the floor, stuffing envelopes with books ourselves, driving to the post office with crates of 500 to 1,000 books that we were selling at a time, and bringing them to the post office instead of arranging pickup because we wanted to hang on to every penny of profit we could. We didn’t want anyone else to do it.

When it came time to write my book, I’d learned this lesson. I learned that for me personally — and some people reading this interview might relate to this — I’m actually a much better “copy talker” than copywriter.

You’re more of a verbal person.

Exactly. My best thinking is articulated by speaking it out as opposed to spending time writing. I make that mistake that so many people do where I’m trying to write and edit at the same time. You’re writing your ideas down, and you’re like, “No, I can word that better.” I get caught in that trap, whereas when I speak, I’m able to get my thoughts out much more clearly and quickly.

That gives great insight into playing to your strengths and not feeling like you have to hold on to every penny — because you can grow your business and income so much bigger and so much faster if you focus on your core abilities. Now, from an outside perspective, you’ve made several massive career jumps. Was it knowing about all these distinctions that gave you the confidence to do that, or was it something else?

It’s interesting. I’m working on our next book right now. I went through this process with the writer I’m working with on this book. We went through this distillation process and really uncovered in my life journey certain threads that were present. What’s interesting is that I am actually incredibly risk averse.

For example?

When I was in high school, I applied to college early because I was afraid I wasn’t going to get into a great school. I was the first person in my high school to get into any college. I found out in October, and most people find out in the spring. But I was in. I was good, and I didn’t have to stress out senior year.

Junior year of college I wanted to make sure I had an internship for that summer to make money. I was one of the first people in college who got an internship working on Wall Street. I got in — done, good. I was safe and didn’t have to worry about it anymore.

My job offer out of college came in August before my senior year, so before my senior year even started, I had my job offer secured. I didn’t have to stress out about it.

What made you so averse to risk?

In part it’s because of my upbringing. My dad worked nights as a shipping clerk for the federal government. He was a union worker. I’m the first in my family to go to college. Growing up, I was taught about job security: Don’t take risks, go with the federal government or the state you’re in, unions are reliable. I had that drilled into me.

When I finally left the shackles of corporate America, the amount of inertia I had to overcome to break free was extreme. I’m glad you brought it up, because people see these big career jumps from the outside, but the reality is it took a tremendous amount of overcoming fear to actually do it.

I imagine even if they were supportive, you probably have people in your family who were shocked at some of the choices you made.

Everyone thought I was crazy. Everyone in my life, except for my wife, thought I was crazy. You have to understand. Here’s my life’s trajectory up until this point: First in the family to go to college. Pretty big deal. I get into an Ivy League school, and I’m going to study neuroscience and become a neurosurgeon. That’s why I chose Brown. Neuroscience was my other major besides East Asian studies.

My roommate, my best friend from college, is now a neurologist at the Mayo Clinic. He is at the pinnacle of neuroscience in the world today. My parents and family, that’s what they expected me to become.

How did you deviate from that path?

I’m in college. I’m going to study neuroscience, and then I tell my parents, “Yeah, I don’t want to be a doctor. I don’t think I want to do this, but I’m interested in China for some reason. I’m interested in Chinese culture and Chinese language and philosophy, so I think I’m going to study abroad in China.” My parents’ first reaction was “Can you make money doing that?”

Then I get back from China, and I say, “China’s really cool, but I’m also interested in finance and investing. I don’t want to be a poor backpacker or a teacher teaching English in China. I want to make a good living, so I’m going to try to get a job working on Wall Street.”

I get a job working on Wall Street for the investment bank Goldman Sachs. My parents say, “Okay. Good. Whew. He’s not going to be a neurosurgeon, but he is going to be an investment banker, so at least he’s going to be able to take care of himself.”

I get out that summer, and I get a job opportunity that’s going to send me to China in the insurance industry. I say, “Okay. Well, I’m not going to do neuroscience, I’m not going to work on Wall Street, but I’m going to do insurance.” They’re thinking selling car insurance or something like that.


So I tell them, “I’m going to do insurance, but it’s going to be in China. It’s all going to be okay. Don’t worry about it.” They’re incredibly dubious at this point.

I go to China, and I do that thing. They see my career is going up, and they see the promise. I get promoted. I move from this job to that job. I’m getting more and more responsibility. I’m making more money. There’s a path there.

And that’s when you realized you didn’t want to live or work in a box.

Exactly. So I turn around and I say, “Okay, Mom and Dad, I don’t want to do this for the rest of my life. I’m done. I want to do my own thing. I quit.” And I quit everything. They said, “So what are you going to do instead?” I said, “Here’s what I’m going to do. I’m going to teach people how to make jewelry with Scrabble tiles and origami paper.”

Ha! How did they take the news?

I explained I was going to sell e-books online. They were so disappointed — to the point that my mom flew out to check if I was mentally okay.

Oh, no.

I said, “No, Mom. It’s all good. It’s totally cool.” But the next thing they knew, I was teaching people how to care for orchids.

What do they think of where you are now?

Just this past year, my parents came to one of my live events where I was on stage for three days. I had a thousand people in the audience, and I brought my parents to the event to surprise them. I brought them on stage and just honored them and said, “There are so many people without whom we wouldn’t be here. But none of us would be in this room if it weren’t for two particular people, because I wouldn’t be here, and those two people are my parents.” I brought them on stage, and I think then they finally got that this was a real thing. It wasn’t like, “Well, when are you going to get a job?” It took almost 10 years for that to happen. It was a cool moment.

How beautiful that you showed them what your reality is and brought it back around to gratitude.

I’m a big believer in that. Listen, I hate it when people say, “I’m self-made this, self-made that.” I may be the first person in my family to go to college, but my parents worked their butts off to help me get there. My dad worked nights. My mom worked multiple jobs. I got a tremendous work ethic from them. I wouldn’t be here if it weren’t for them.

I think we all have people in our life, whether it’s our parents, teachers we had growing up, mentors, coaches … We all have those people who made sacrifices, who did something extra for us to help us get to where we are today.

How do you stay driven now that you’re successful?

I use what one of my mentors describes as your “through line,” which is the thread that ties everything together in your life. My through line is to leave it all on the field. My belief is that we were put here on this planet for a very short amount of time. Whatever your belief system is, it doesn’t really matter, but we have a very short amount of time. I believe we all have a duty to give it all we’ve got and make this world a little bit of a better place. There are people in our lives who have made all sorts of sacrifices to make that happen. If nothing more than to just honor those people, you’ve got to do what you feel you were put here to do. You’ve got to give it everything you’ve got.

No one’s an island. There’s a reason that gratitude gets you further than selfishness. Now, you’ve been quoted as saying that Tim Ferriss’s book The 4-Hour Workweek changed your life. What other books have been life changing?

There have been so many along the way. In the early days, there was this whole world that I didn’t even know existed. I first encountered it through Dale Carnegie’s How to Win Friends and Influence People. I still have my paperback version that’s beat to hell. It has tears in it. The binding is duct taped.

Then there was my first version of Think and Grow Rich by Napoleon Hill. That book, again, is beat to heck and is a total mess of dog-eared pages and coffee stains, but I’ve kept it, and I’ll keep it forever.

Those were a couple in the early days when I was first making that leap from this paradigm of go to college, get a good job, get promoted, maybe get headhunted to work for another company, and then someday retire. That whole paradigm shift that happened — those were at least three of the books that had a big impact on my thinking about there being other paths out there and that I could take control of my own destiny.

When you left China and moved back to Texas, you lived in a cheap apartment in Brownsville, dependent on your wife’s salary, with two collapsible lawn chairs for living room furniture. But today, if someone types your name into a search engine, one of the suggested key phrases that comes up is Ryan Levesque net worth. How does that make you feel?

Gosh. I get a little emotional thinking about it. Here’s the reality if I just tell it to you straight. If you want to further yourself, if you want to better yourself financially, it takes a degree of sacrifice. Everyone I know in my life who’s been wildly successful financially has had some form of the bologna sandwich and ramen noodle days.

I’m laughing because I relate.

We all go through it. There’s nothing wrong with it. You might be reading this in your 30s or 40s or 50s, and maybe you’ve never had those moments, or maybe you’re having one of those moments right now, but there’s nothing wrong with it.

So how does it make me feel? Gosh. It doesn’t feel that long ago. That’s the thing. In some ways it feels a lifetime ago because I’m doing this interview now, I’m driving my $150,000 car, my wife and I own multiple properties. Life is good, and we’ve worked really hard for it, but I can’t complain. I love my life. I’m not afraid to say that it’s required hard work.

I’ll tell you, when we were living in Brownsville, date nights for us meant going to Stars Drive-In on Thursdays because Thursday was $1 hamburger day. We had a $5 budget, so we’d bring waters, we’d get four hamburgers and fries, and that would be my meal for two meals. It would be our date night and my lunch the next day. That was our date night. Five bucks.

Our apartment had bars on the windows. We still have those stupid lawn chairs — they were a free perk from a bank account we opened up. I can’t let go of them. They’re too sentimental. We had a mattress on the floor. We had an old desk that was terrible. We had an old TV. We had to jam the rabbit ears of the TV into the windowsill to extend the metallic antenna system just to get the channels.

This was the best: We didn’t pay for cable, but we paid for internet. We had cable internet, and that was the one thing I did not compromise on was the fastest internet that I could get in that apartment. We had the internet to run the business. For whatever reason, the cable of the internet ran on the same wavelengths as three random cable channels. But as a man, they were the absolute worst channels I could’ve asked for. Why couldn’t it have been ESPN, ESPN2, or something like that? No, no. It was Lifetime Movie Network, the Hallmark Channel, and the WE channel, as in, the women’s channel. It was one of those moments where it’s like, “Oh my gosh, we have cable!” Uh, no we don’t.

And your wife loved it.

She did. It was terrible. Anyway, I remember those days. It feels like it was yesterday. We had one car. I drove my wife back and forth to work. I’d drive her to work in the morning, I’d come back home, I’d work, I’d pick her up in the afternoon, come back home, eat dinner, and we’d work until we passed out at night.

But here’s the deal: The reason we moved to Brownsville was the Scrabble-tile business. We started that when we lived in Hong Kong. But then it went to nothing, and we ran out of money.

At the time, my wife and I looked at each other and said, “What are we going to do?” I’d quit my job at this point. She was in grad school in Hong Kong at HKU, Hong Kong University. She said, “You know what? I’ll get a job.” Her major in college was art history, and her master’s degree is in decorative arts. She was getting a PhD in history. It wasn’t like she was studying economics or finance, or any field where you make a ton of money.

She got an amazing job as a museum curator, but her salary was less than $40,000 a year. We not only had to live on that, but that’s what was funding the new business that we started, which was the orchid business. We were starting again from scratch. We made ourselves live on $20,000 a year, so we had a little bit of money to put into the business to get it going. We took it from nothing when we first moved, to $25,000 a month in a year and a half. My wife quit her job at that point.

Then we moved to Austin, which is where we’ve lived for the last 10 years. We launched another business. It took us to half a million dollars a year. Launched a third business and grew it into $10 million a year plus and growing. That’s how it all started.

So you had a great work ethic thanks to your parents, and your wife is a really supportive partner. But while you were trying to build a sustainable online business, you said you were held back by the fear of failure. How did you overcome that? Because you have clearly overcome that.

There’s stuff now that I’m going through that I’m afraid to fail at, where I’m afraid to move to that next level. I don’t know that it ever goes away, right? I’ll tell you two stories, and I’ll tell you something I told one of my kids one day.

I was driving my son to school, and he was about 4 years old. It was a Montessori school. I mentioned we have a Montessori teacher from Taiwan who lives with us, so we do a bit of a hybrid. We try to get one-on-one time with the kids. We do this combination with a local Montessori school where they spend a little time at the school to be with the kids and then time at home with our tutor, so they have the Chinese time.

Anyway, I’m driving my son to school, and he’s about 4 years old at the time. He just started crying and said, “Daddy, I don’t want to go to school. I don’t want to go to school today.” I said, “Henry, what’s wrong? What’s going on?” He said, “Dad, I don’t want to go to school because I can’t hang up my jacket.” He was at that age where they try to foster independence and push them to grow, and he couldn’t hang his jacket up on a hanger. He couldn’t do it. He had to throw his jacket on the ground, and it was hard for him. As a 4-year-old, it was something that was really tough.

I said, “Daddy does stuff all the time that he’s afraid of doing, that scares him. It’s not about not being afraid; it’s about this …” And I didn’t use these exact words for him; I explained it to him in a way that a 4-year-old would understand.

But I basically said, “There are only two things you need.” This is something I think my parents taught me. There are only two things in this life that you need to be successful. The first is courage, which is doing the thing that scares the life out of you, in spite of that fear. The second is grit, which is picking yourself up when you fall or when you fail, doing the thing that scares you — because you are going to fail at it. That’s just life.


It is what it is. For me, I think it’s just the more times you push yourself to do stuff that you’re scared of doing, and do it in spite of that fear, and the more times you skin your knees on the pavement … You know, when that happens, the skin on your knees starts to build up calluses. When you fall again, you’re saying, “You know what? The last time I fell, I got back up, and I’m okay. It didn’t kill me.” I remind myself of that all the time.

As we gain more experience in life, one of the benefits is that we have more of a mental library of things we’ve done where we’ve succeeded in spite of that.

One of the things I teach our students is where I say, “Listen. You need to have three life events that you can come back to in your mind whenever you’re feeling afraid. You want to find things that you’ve done in your life where you succeeded in spite of the fear you had about doing that thing. These things can go back into childhood, they can be things when you were a young adult, they can be things that happened last week, but you need to have three things that you can go back to that you remind yourself of. The next time you run into that situation and you’re afraid to take that action, just play back in your mind the mental movie where you were the hero and you succeeded in spite of that fear. Play back that movie as many times as it takes to remind yourself that you are a badass and you can do this. You totally can do this.”

I think having that is powerful just from a tactical level as a strategy you can use to overcome that fear.

Great tip, because it’s easy for all of us to get caught up in current problems and forget anything that we’ve ever achieved in life. For anybody who is on the fence right now — and to be frank, I can’t see how they would be on the fence after hearing what you just said — but for those who are still just a little bit worried about going after their dreams to write and get paid for it, what is the number-one getting-started tip that you can share?

It goes like this. It’s something I learned studying neuroscience at the Ivy League level. It has to do with the psychology of fear. Whenever you try to make any change in your life, even if that change is incredibly positive, like bettering yourself by pursuing a career in writing, your brain’s response to that change is that the change is a threat. You actually fire off the threat warning bells in an area of the brain known as the amygdala, which is where your fight-or-flight response is.

But here’s the cool part. You can hack that response, so your body doesn’t release those neurochemicals and freak you the heck out and say, “Whoa, wait. Maybe that’s not a good idea.” The secret is this, and this is from the work of Dr. Robert Bauer out of UCLA. He’s an incredible brain scientist.

Here’s the hack; it’s so simple and so profound. The secret is to ask yourself what next possible step you can take that is so small, it will be literally impossible to fail.

For example, if you want to go for a run and get a little bit of exercise, and you’re feeling like, “Oh my gosh, I don’t feel like going for a run,” you ask yourself what next step you can take that is so small, it’ll be impossible to fail. And that might be simply walking two steps in the direction of where your shoes are.

The impossible-to-fail step usually is so small that you laugh at how ridiculous it is. If you’re struggling figuring out what to write to someone, maybe in a writing assignment, open up your laptop and just start typing nonsense characters in a blank Word doc or Google Doc or whatever you feel like typing in.

What it does is create action-taking momentum, and it’s what’s called a micro-commitment. If you’re feeling stuck right now after reading this interview, my challenge — my advice — to you is simple. Whatever it is you want to do, whatever that next step you want to take is, think about what is the absolute smallest thing you can do in that direction? The step that is literally so small, it’ll be impossible for you to fail? Do that right now. Once you’ve done that next impossible-to-fail step, do the one after that. That’s it. That’s the secret.

So you shut down your fight-or-flight system, and then you take those steps from there, and that’s how you make the big things happen.

That’s the secret.

That’s beautiful. That is fantastic. Ryan, thank you so much for sharing your wisdom and so many lessons learned.

This interview was previously published in the June 2018 issue of Barefoot Writer. To read more interviews from fellow Barefoot Writers be sure to check out The Barefoot Writer's Club.

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Published: July 13, 2018

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