Ryan Levesque is an Inc. 500 company CEO and author of the number one bestselling book, Ask, featured by Inc. magazine as the number one marketing book of the year and by Entrepreneur Magazine as the number two must-read book for budding entrepreneurs. He’s used the Ask Method to build multimillion dollar businesses in 23 industries, generating over $100 million in sales in the process. He’s also the co-founder of bucket.io, the segmentation funnel software that entrepreneurs are using to implement the Ask Method in their businesses.


In This Episode

Bruce Lee once said, “I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.” Ryan Levesque took that quote to heart and built an entire business based on excelling at one thing: segmentation. In this non-stop episode of Modern Ontrapreneur, Ryan reveals a huge tactical business tip for beginners, his high-tempo testing method that can be used by those more advanced in their business, and what it means to be an entrepreneur in this modern era.

Topic Timeline:

1:48 Hire Faster

Big leaps forward in Ryan’s business have come from hiring talent.

5:22 My Secret Superpower

You’ve heard it here first, writing copy is now a superpower.

6:44 A Powerful Tactical Tip

Ryan gives an incredibly simple, yet effective tip to converting leads and building your list.

8:43 Fear the Man Who Has Practiced One Move a Thousand Times

You just need one thing to excel at and, in Ryan’s case, it’s segmentation.

10:11 Funnel Side vs. Launch Side of Business

Launches can be unpredictable so focusing the operational budget on the funnel side helps fuel predictable growth to then fund the launches.

11:53 High Tempo Testing

Focusing on testing as much as possible as quickly as possible.

15:01 Leave It All On The Field

Be the best example you can be.

16:25 Focus on Your Zone of Genius and Tell the Truth

Business tools today allow entrepreneurs to spend more time on their unique skill set, and modern entrepreneurs should have their moral compass leading people to the truth.

In business and life, I’m of the belief that you just need one move. You need one thing that you excel at. If you just do that one thing over and over again, it can tremendously help you.
– Ryan Levesque

Show Transcript:

LR: Welcome on Modern Ontrapreneur! I’m Landon Ray and today I have Ryan Levesque who’s an Inc. 500 company CEO and author of the number one best selling book, Ask, featured by Inc. magazine as the number one marketing book of the year and by Entrepreneur Magazine, as the number two must read book for budding entrepreneurs. He’s used the Ask Method to build multi-million-dollar businesses in 23 industries, generating over $100 million in sales in the process. He’s also the co-founder of bucket.io, the segmentation funnel software that entrepreneurs are using to implement the Ask Method in their business. Thank you so much for being here. Welcome on Modern Ontrapreneur!

RL: Landon, it’s awesome to be here.

LR: You’ve had a lot of success. I remember you just getting started in this industry. Feels like just yesterday, but I feel like it was maybe longer than that, like three, four, five years ago, even. How long ago was it that you really kicked off this thing?

RL: I came into this world of building online businesses back in 2008.

LR: So it’s been a little longer, nine years.

RL: That’s when I first started in obscure niche markets, basically just working for myself. I was unknown, hiding behind a computer screen. I built a little business in the orchid care market, and the Scrabble tile jewelry market, and then had some success in all these weird markets, and eventually translated that into teaching this methodology that’s come to be known as the Ask Method, which I’ve used to enter all those different markets.

LR: You have been working on this stuff for a while now. You’ve gone through building your own business in these niche industries, and then reinventing yourself as an educator. If you could go back and give your 2008 self a piece of advice, based on what your experience has been so far, that would make it easier, or more effective, or whatever, faster, what would it be?

RL: It’s a question I’m asked all the time. It’s usually phrased different. It’s what would you do different? The thing I would do different is I’d hire faster. I’ll tell you Landon, I hung on to so many things because my wife and I, we started our business together. It just felt like we didn’t have an extra $1,000 to spare, $500 to spare, what it was. We were packaging books, putting stamps on, driving it to the post office, far longer than I care to admit. That’s the biggest mistake that I made.

LR: Like since last week.

RL: Yeah. Exactly, is hire faster. Every time that I’ve hired, you can speak to this as well, but every time I’ve hired, it’s resulted in a big leap forward in our business, and taking something off of my plate and putting on someone else’s.

LR: How big is your team at this point?

RL: We have across both companies, two companies mainly now, so we have our Ask Method company, which is our training and education okay. That’s the book and we have education programs, we teach the marketing methodology. Then we have a software company, Bucket, which is the technology to implement that. Across both companies, we’re about 55 between the two.

LR: It’s really grown quickly.

RL: It’s grown. Four years ago, it was me, my wife, and an assistant.

LR: There you go.

RL: When it grows, you’ve experienced the same growth, it happens fast.

LR: Yeah. Exactly. If you’re thinking about hiring that first person, who is that? What do they do?

RL: It’s an assistant. It’s someone who is kind of like a virtual assistant. If you have an online business, there’s just a multitude of things you need to do. Uploading stuff to Facebook, uploading blog posts, queuing up emails, spell-checking things. If you do any travel or anything like that, just helping with all that sort of thing. You want a jack-of-all-trades person who’s really detail-oriented. Most entrepreneurs are visionary, high on Quick Start on Kolbe, so we’re really good at starting things and we need someone else to clean up our mess. Someone who’s really high on follow through, I found is really important, and someone who is able to be a jack-of-all-trades on all these small tasks.

LR: Because a lot of people will want to start by hiring … Outsourcing big parts of their business, like you need somebody to do my marketing, or somebody to do sales, or something like that. But by hiring an assistant, you’re keeping the high-level stuff for yourself.

RL: Totally. The exercise you want to go through is you look at your week. You basically look at the hours you’re spending on different tasks. You ascribe dollar values to that task. For example, if you’re taking out your own garbage, or you’re shoveling the driveway, ask yourself, “Okay. How much would it cost me to pay someone to do that task?” Okay. That was a $15 an hour task. You just look at all of your tasks and you say, “Okay. What are the ones that are the lowest dollar value, that I don’t enjoy doing?” If you love shoveling the snow because you just love that sort of thing, then do it. Whatever. Here we are in Santa Barbara, there’s like … Snow’s like, “What?” But if you love that sort of thing, do it. Then you pass that over to someone else, and you just work your way up. What that allows you to do is you’re constantly doing higher and higher dollar value tasks that warrant your time as a budding CEO.

LR: What do you feel like your particular unique skill sets are that have had you have the kind of success you’ve had?

RL: There’s a lot of things I’m not good at. We run our company now according to the Rocket Fuel model, which is a model where at the top of all the most successful companies in the world, companies like Apple, you’ll see that there’s not just one person at the top, there’s two. There’s a visionary and an integrator.  The visionary is really good at big picture ideas. They tend to be a creative type, tend to be really good at starting things, and kicking off new initiatives. Whereas integrates are really good at picking up the pieces, running the day-to-day operations, running meetings, managing projects, that sort of thing. I’m not good at that stuff at all. That’s where I spend my time now, is envisioning new marketing campaigns, visioning new products, writing copy is one of my secret super power. I spend a lot of time writing our highest leverage copy for our most important things. That’s where I spend a lot of my time.

LR: Interesting that you say that. You’re a visionary. You say, “I’m the idea guy. I like to kick stuff off.” There are a lot of entrepreneurs who see themselves as idea guys but are not fundamentally at a place where they’re gonna attract a real operator, because operators are not that easy to come by. Right? How do you get to that point, or when is that point do you think?  I mean, you’re maybe lucky enough to be married to one, but when do you get to that point where … You’ve got to actually start. You can’t let yourself have the excuse for too long that, “I’m an idea guy. Somebody pick up the pieces.” You need to get going. But then you need to eventually attract that person. How do you make that happen?

RL: It’s a huge question. I’ll answer it with a tactical tip that I think is really powerful. One of the things that I teach in the Ask Method, as a way to build your list, get more leads, and bring people into your world, is to use what we call the power of micro commitments, which is instead of when someone lands on your website, asking them to provide their name and email address, and all this information at once, you ask them to take little baby steps. You might ask a multiple-choice question.  Before we get started, are you a man or a woman? Or are you just getting started, or are you experienced? A very simple, low threshold question. The reason why that works is because it hacks your fear psychology. It hacks an area of the brain known as the amygdala, which is the fear center of your brain. It allows people to take action by shrinking the size of the step.  That’s a marketing tactic. How do you apply that to yourself from a personal productivity standpoint, or answer your initial question, which is how do you get started? What you do is, whenever you’re running into some sort of resistance in your business, the thing that you’re working on right now, you want to ask yourself this very simple question. What is the next small I can take that is so small it’s literally impossible for me to fail? Whenever you’re approaching an area of your business that you’re not good at, for me it’s running meetings, getting things done, managing projects, that’s not natural to me. I use this little trick. I just say, “Okay, how can I move this project forward in the smallest possible way, it’s literally impossible for me to fail?” That’s a question you can ask yourself whenever you’re running into sticking points, or areas that you’re maybe not good at. If you’re more of the visionary, and you’re not good at the operator side of things, it’s a way to get momentum. Once you have that action taking momentum, then you can make progress from there.

LR: You’ve grown from, like you said, two or three people, four years ago, to over 50 now. I mean, this is a little bit of a softball, given that your business is built around a particular tactic, but what’s working now in your business to generate business? Where are you getting all these customers? What’s the thing at the moment for you?

RL: For sure. There’s a quote that’s always resonated with me. It’s a quote attributed to Bruce Lee. It’s, “Fear not the man who has practiced a thousand moves once, fear the man who has practiced one move a thousand times.” In business and life, I think, I’m of the belief, that you just need one move. You need one thing that you excel at. If you just do that one thing over and over again, it can tremendously help you.  My one move comes down to segmentation. Rather than treating people in a one-size-fits-all way, what we do is we put people into buckets. We put people into buckets to tailor the buying experience, so that it’s better matching with their unique needs, wants, and desires are.  The way we do that is by using quizzes, assessments and segmentation funnels on the lead-generating side of our business. That’s what we teach people how to do. We have technology that does that. That’s all of my success in the 23 different niche markets that I went into. That was my one move, is when everyone … Pick the market. Orchid care, satellite television, it didn’t matter. Everyone would treat people in a one-size-fits-all way. We’d cut the market up into different segments, and approach people in a more tailored customized way.

LR: You’re driving traffic into these quizzes or assessments. You’re doing that at … I think people in your community seem to be doing that in a couple different ways, either with cold traffic via ads, also people are applying that now to Jeff Walker’s Product Launch Formula. I’ve seen you do both.  Just give us a sense of what percentage of your business in the last year has come from those two categories of leads?

RL: We have what we describe as the funnel side of our business, and the launch side of our business. Philosophically, we like to run our operating expenses on the funnel side of our business. That means, we want to have the leads that are coming in and the sales that we generate on an evergreen basis, coming in all day, every day. That’s the money that we budget around.

LR: You know you can count on it.

RL: We can count on it. Exactly. It’s predictable. If it starts to trail down or up, you can predict it. Launches are very unpredictable. If you have a launch for something, gosh, heaven forbid, you launch in the middle of a hurricane or a tragic event, it just could….

LR: Or a tech breakdown.

RL: Tech breakdown, anything like that. There’s just so many things that could go wrong, so you’re putting too many eggs in that one basket. We look at that as, we use that income to fuel our growth. If we have a new initiative that we want to take on, then we use that money. We park that money away, and then we use that to reinvest in whatever new product we’re creating, or new initiative that we want to try, or new experiment. It’s about 50/50, the business. We’re in heavy growth, investment mode right now.  We’re putting a lot of resources in both. Long-term, where I want to be is closer to 90/10. I’d love to be 90/10 on the funnel side, 10% on launches and just have that be the cherry on top.

LR: You’ve got a lot of experience under your belt. Now, we’re always learning and growing. What is your learning edge right now? What are you struggling with, trying to figure out? What’s the next thing?

RL: For me, it’s on the software side of our business. In bucket.io, we are in rapid testing mode. We just recently kicked off an initiative, where we built a high-tempo testing team. What we’re doing there….

LR: High-tempo testing team.

RL: High-tempo testing. We’re doing rapid tests where we have enough data to make changes to the product in a seven-day period. We’ll add something. We’ll put something in the onboarding sequence. We’ll add a new feature. We’ll see if it moves the needle on our core metric that we look at, which is activating users. If it does, we’ll keep it. If it doesn’t, we’ll try something else. That’s a totally new area for me. It’s my first software company that I’m building, so it’s a huge learning and growth opportunity. It’s uncomfortable. That’s when you know you’re doing the right thing, because when it’s hard and it doesn’t come natural, that’s the thing to focus on.

LR: I know that there are probably a lot of people who are gonna watch this who aren’t software folks but, since I am, I just have a question I’ve got to ask about that, which is: When I think about split testing, which is what you’re talking about, it occurs to me that it takes a certain number of tasks to have some valid result. To have confidence enough that it’s not just random what you experience. Are you really getting enough sign-ups in a week? Your thing just launched. I’m gonna guess that you’re not getting enough sign-ups in a week to have what … When we think about an email split test, you want hundreds or thousands of tests to even get to 80, 90% confidence. How are you dealing with that in a sign-up funnel?

RL: To be clear, this is after people have signed up to use the software and are in the software. What we’re looking at, just like in a marketing funnel, when you do any form of split test, you’re gonna have the most volume, the most traffic, at the front of the funnel. That’s where we are right now. You’re right, the limiting the bottleneck is how many users do we have? We have a few thousand users in the software right now.  But, those users are still in the early stages of their experience with the software. What we’re testing are things like their first experience, the first time they log in, the first quiz that they build, the first audience that they build when they connect with Facebook. Our conversation, how they’re connecting their Ontraport account with their bucket accounts. We have a split test on that right now, to see if we can improve that experience and get more people to make the connection.  We have to test the very beginning. What we can’t test now is someone that has … We don’t have enough users that have a million leads, so how to get to one million to two million. We just don’t have enough users for that. Just like a marketing funnel, I think the key is starting at the place in the funnel, like you said, where you have enough volume to get those statistically significant conclusions.

LR: Interesting. Tell me, you have some years yet to go, obviously in your career. You’re a young guy. You’ve got a ways to go, but if you can think through 20, 30 years down the road, and looking back, what is this all about? What would you like your legacy to be?

RL: For me, I went through an exercise once. One of my mentors took me through this. It’s a very powerful exercise. I won’t go through it now, but you imagine you’re at the end of your life, kind of like what you’re asking right now, and you imagine you’re saying your goodbyes to all the loved ones in your life. The last person you say goodbye to is a small person in your life. It can be a child, grandchild, it can be a nephew, niece, just someone that’s really important to you. You say goodbye. This is the last person you’re saying goodbye, before you’re about to take your last breath.  The question you ask yourself is, “What are the final words of advice you leave for that person?” Whatever that is for you, is your through line. It’s the thing that drives you more than anything else. For me, my through line, whenever I’ve gone through this exercise, it’s simple. It’s “leave it all on the field.” For me, that’s it. I’m going. I know that we’re impacting tens of thousands of entrepreneurs. I’ve got big numbers, big goals, people that I want to transform their lives. That’s the thing that’s exciting to me. I want to be the best example I can be to my kids, to my two boys. I want to know that at the end of my days, I’ve left it all on the field. There’s literally nothing more that I could have given, and just laid it all out.

LR: Great. We call this thing Modern Ontrapreneur. We’re trying to identify what it is that’s unique and interesting about this moment in entrepreneurial history. Things have changed so fast. You’ve been a part of it now for a decade, and that feels like an eon, especially online business. What do you think it is that’s unique about this moment? What are the unique opportunities that we have? What are the responsibilities that we have as entrepreneurs today?

RL: Take the opportunities first. So I look at the 10 years that I’ve been involved in this industry, when I came into this industry, you had to code your own website. You had to use HTML and CSS to code.

LR: Dreamweaver.

RL: I still have Dreamweaver on my computer. I was from Dreamweaver. That’s the extent of my HTML and CSS. The beautiful themes that you have, the landing-page builders, the funnel-building software, none of that existed. None of it existed at all. You had to code everything from scratch. Where we’ve come is that instead of having to learn all those fundamentals, I think entrepreneurs now can really focus on their zone of genius. They can really focus on what their unique skills are, and use the tools that are there, speaking specifically about building an online business.  Now, I think the responsibility is one of telling the truth. I think we live in a world now, I think we can all agree watching this right now, that we’re just inundated with messaging that is not true. With great power comes great responsibility. I think as an entrepreneur your moral compass needs to continually be pointed toward it, asking yourself, “Is this the truth? Am I telling the truth? Is the data the truth? Am I leading people to the truth?” I think if you use that as your compass, you continue to focus on service, then you’re doing everything you can do.

LR: Ryan, thank you so much for being here.

RL: Landon. Awesome. Appreciate it.

LR: It was really a pleasure.

RL: Likewise.

LR: Will you sign our wall?

RL: Totally.

LR: Thank you.

RL: Awesome.


Want more Modern Ontrapreneur Podcast?

Check out the previous episode featuring Andrew Wadsworth of IT Mooti.


About Ben Cogburn
As Ontraport’s Traffic Manager, Ben Cogburn spends most of his time in our parking lot. Just kidding, he’s our resident digital advertising guru. As a geology enthusiast, Ben graduated from the University of California, Santa Barbara with a degree in Environmental Studies. So to say that he likes rocks is an understatement. You can find Ben hanging out with his rock collection, playing video games or hunting down new figurines to add to the impressive display he has on his desk.