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Ryan Deiss – Young Entrepreneur Interview

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Ryan Deiss is the Founder and CEO of DigitalMarketer.com

Ryan Deiss – Founder and CEO of DigitalMarketer.com

Ryan Deiss is a self-made Internet success who is one of the leading, if not THE leader in the world of membership websites. Ryan has a style of writing that is no-nonsense, and he is one of our favourite entrepreneurs. At the young age of 25 he owns over 20 websites earning him several million dollar’s a year.

Hello Everyone,

Today I got the chance to interview a great guy and a personal friend of mine, Ryan Deiss! Ryan makes 7 figures a year from the Internet and in this interview he gives us a brief insight into his business.

Ryan and his team at DigitalMarketer provide step-by-step marketing checklists designed by industry experts to work all the time. You can get them at Ryan Deiss DigitalMarketer Lab, check it out now!

Ryan, thanks for your time. I know you are a busy man right now, could you please tell us a bit about you and how you started making money on the net?

It’s kind of embarrassing to admit, but my first job in the “internet marketing” world was a college internship with a spammer. At the time spam wasn’t as big a deal as it is today (and it certainly wasn’t illegal), but basically all we did was harvest email addresses from forums and other places and then spam the crap out of those poor folks.

Obviously that business model was flawed down to its core and so I wasn’t surprised when it folded in early 2000. What it taught me, though, was the power of the internet and the shear volume of sales that can be generated with just a couple clicks of the mouse.

I was hooked! So I set about finding more legitimate methods of generating traffic and building email lists, and that’s what ultimately lead me to where I am today.

What were the main challenges you faced early on in your online ventures? And do you still encounter them to this day?

From a purely tactical standpoint my biggest challenge is always traffic. Generating targeted traffic, in my humble opinion, is the most difficult part of any new online business venture. Product is easy. Creating a compelling offer is fairly easy. Even writing good copy is fairly easy at this point.

But traffic always requires a good bit of effort. In some markets we can do affiliate marketing fairly easy, and in others we’re forced to rely on more costly methods such as pay-per-click and banner ads.

In the end we almost always find a way to make it work, but some markets and offers definitely require more trial and error than others.

The second big challenge that I faced in business early on (and still struggle with today) is focus. There are so many opportunities at any one time, and left to my own devices I’d probably start 40 new projects a week and never finish anything.

Fortunately I have a good team around me that keeps me head on straight, but in the early days it was a lot harder. Looking back, this is probably the single thing that held me back more than any other. That’s why I suggest to anyone who suffers from “Entrepreneurial ADD” (like me) to bring on an operations person or a partner who’s more organized and business savvy. In my case it was well worth it.

If you could go back in a time machine to the time when you were just getting started, other than not agreeing to this interview, what would you do differently? And what advice would you have given to yourself if you could only relay one piece of advice to your former self?

I would focus on continuity (i.e. recurring income) in my business MUCH sooner. This is what generated the biggest breakthrough in my business…

Back in 2005, I made a commitment that I wouldn’t start a new venture unless it had a recurring income component. And while this limited the number of markets I could go into, it allowed me to build sustainable businesses that spin off a predictable amount of cash each and every month. And trust me, it’s a very freeing feeling to know on the 1st of every month about how much money you’re going to make over the next 30 days…even if you didn’t do another ounce of marketing!

Do you think that entrepreneurialism is something that is in your blood? Or is it something that can be learned?

Like everything in the “nature vs. nurture” debate I think it’s both. As a kid when people asked me, “What do you want to be when you grow up?” I would respond:

“I want to be a millionaire!” (I watched a lot of Batman as a kid and Bruce Wayne seemed to have it pretty good.)

I still remember how this would confuse the adults. Obviously they expected to hear “astronaut” or “fireman” and some would probe more to find out HOW I was going to become a millionaire.

As a kid this seemed like a silly question, and as an adult I still think it’s silly. The “how” is frankly irrelevant. I knew what I wanted and I knew I’d figure out how to get it at some point. As it turns out, my parents weren’t rich so inheriting the money (like Bruce Wayne) wasn’t an option, so starting my own business is what I was left with.

I don’t know if my long-winded response really answers the question or not, so let me have one last stab at summing it up…

The only trait that really matters (in my experience) is an intense desire. I had an intense desire, even as a child, to be wealthy and achieve great things. The vehicle that got me there (entrepreneurialism) was almost irrelevant. It was the END I was concerned about…not the MEANS.

The membership model is something that has been around a long time, but it seems that it was overlooked by the vast majority of webmasters, why do you think this is? And now that they are more popular than ever, have the rest of us missed to gold rush?

Most of our business principles were pass down to us from the Industrial Revolution. And while a lot of these are great, one that isn’t so great is what I call “transactional” thinking…

Transaction thinking looks something like this:

Widget A costs me $2 to make. I sell widget A for $6 so my profit is $4. Repeat a lot of times to get rich!

In this kind of relationship the customer is looked upon as just a one-time sale, which is why most businesses spend all their time and money getting new customers.

By looking at your customers more “relationally” than “transactionally” you not only increase the overall value of each customer, you have a lot more fun doing it.

This is what membership marketing is all about! I don’t create “products,” I create “clubs” and “groups”. Sure, my members get access to “products” when they join my “clubs,” but the positioning is completely different.

Ryan, I read that you share my loathing for webmasters who “play work” by spending so much time on Internet forums. But what advice would you give to webmasters who are looking to find information and advice?

If you have a specific question then forums can be a great place to ask them. But perusing the forums on a daily basis just to see what people are talking about is a huge time-waster.

That said, you do want to be careful about the source of your information. Just because someone on a forum said it, that doesn’t necessarily make it’s true. Make sure your source is well-qualified or backs up their answer with concrete details.

More times than not I’ll seek out real experts and PAY THEM for their time to get answers I know I can trust. It can be a lot more expensive than forums on the front-end, but believe me when I say it can save you a fortune in mistakes NOT made.

Ryan, if all of your money, websites, contacts and products were wiped off the face of the earth tomorrow, what would you do if you had to start from scratch? What model would you use? What techniques etc?

For me everything starts with the market, so what I’d do is isolate a hungry and impulsive group of people and then find their biggest pains. (Forums are a good place to do this kind of research.)

Then I’d try to find an expert or two and do exactly what you’re doing here…interview them. Interviewing experts is far and away the fastest and easiest way to generate quality content, and if you position it correctly it doesn’t have to cost you a thing.

I’d turn this interview into a low-cost product, sell it via PPC and affiliates (starting with the interviewee if they have a list and are willing to mail to it). I’d be willing to give up all the front-end profit because I’d roll people into a monthly continuity/membership program where they receive a similar interview each and every month.

That’s it!

If I netted $20 off of every member every month, all I’d need to do is get 500 members and I’d have a 5-figure monthly income. Not too shabby if you ask me!

Ok, final question from me: What can we expect to see Ryan Deiss doing in the future?

I have a model that’s proven and repeatable, so now it’s all about taking that model into bigger and more profitable markets. The work on the front-end is always more and the risk is greater, but the upside potential is HUGE!

Other than that it’s all about funnelling profits from business into more passive income vehicles such as real estate and the financial markets.

I have had products that struck gold, and products that flopped. But more importantly, I have experienced what it takes to succeed, and watched in horror while others failed. And every one of these experiences…the good, the bad and the ugly, have all been cataloged in my personal marketing and success diary (a.k.a. my “profit diary”).


Want more from digital marketer leader Ryan Deiss? You can find more Ryan Deiss products and tips at his website ryandeiss.net or follow him on social media.


  1. Darren Boyle says:

    Excellent open honest interview. I have followed Ryan for over a year now since getting knocked off of my motorcycle and he hasn’t yet failed to impress me yet. I also use a lot of his skills for search engine optimisation and internet marketing for kent small business marketing services

  2. Eric Williams says:

    This is a great interview. I admire Ryan’s work. As a matter of fact, my first check in internet marketing came from Ryan.

  3. Yeah, a honest interview. Great to have such inspirational figures when you are new to the “Business on the Internet” world….

  4. Michael Searles says:

    Outstanding interview.

    Great questions and a series of ‘no-holding-back’ answers from Ryan Deiss.

    There’s even an answer giving readers a proven money-making formula for cost-free product creation. Insanely generous!

    I want Ryan Deiss as a guest in my own media of Interviews with Experts.

  5. Great Interview! Very good questions asked. Especially liked the last one. Giving up the front end money sounds scary but I agree that it will pay off in back end profits.

  6. Hey guys,
    Ryan i believe knows his onions

  7. Hi Michael,
    Excellent job on the interview ! I ‘m a Master’s Degree student from Paris and I am really interested in young successful entrepreneurs. I am currently taking an Entrepreneurship class, in which I have to conduct an interview with an entrepreneur. I would like to know you would be interested in answering few questions (online).
    Please let me know
    Thank you

  8. Good post, i’ve been stuck there

  9. Helpful post, i’ve not been blogging long and this has helped a lot.

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