Chris Ducker of Youpreneur on Hustling and the Rise of the Youpreneur

BBR 244 | Rise Of The Youpreneur

When businesses succeed, they are most likely to burnout at some point, maybe due to poor management or the time just wasn’t right. When Chris Ducker’s first business eclipsed its first million dollar year and everything seemed to be going great, the business burned out. Being a sales and marketing guy at the core, Chris knew that what he needed to do was to keep the hustle going that led him to genuinely enjoy helping people find solutions to their problems. As the author of Rise Of The Youpreneur, Chris shares his 17-year entrepreneurial journey.

This is Megan Hall from The Inspired Women Podcast. What I love about the Business Building Rockstars Show is the wealth of information that Nicole and her guest share on the podcast. I walk away inspired after every single episode I listen to. Thank you, Nicole.

If you would like to introduce an episode and share your love for the Business Building Rockstars show, go to


Listen to the podcast here:

Chris Ducker of Youpreneur on Hustling and the Rise of the Youpreneur

I am super excited to be here with the one and only Chris Ducker. Welcome, Chris. How you doing?

I'm doing very fine. Thanks for having me here.

I'm really excited about some of these things you've got going on right now. The Rise of the Youpreneur is about to come out. You've been at this a really long time. Do you mind taking us back to the beginning? How did you first decide to get in the online space, and when did things really took off for you?

I setup my first business in 2003.It's been fifteen years as an entrepreneur now. Like a lot of people that were building businesses back in the early 2000, I would use the internet mostly for just searching stuff on Google, email, looking at funny cat videos on YouTube, and all that stuff. We had a website up and running and all that fun stuff, but it was really around 2009 when I started to consume a lot of online content. I was watching a lot of videos on YouTube. I was reading a lot of blogs. One of the first blogs I ever read was Duct Tape Marketing by John Jantsch, and it's an honor to call him a good friend now. It's amazing how things can go almost full circle.

That was the year for me when I discovered the online world in terms of what it can really do from a business perspective, other than just having like a brochure type of business website up there for people to contact you in and hopefully do business with you. Fast forward a little bit, late 2009, I burned out. I was at that point a very typical business owner, Type-A entrepreneur. I had about a 130 people working for me at a call center business that I still own and operate but I don’t manage myself anymore. We just eclipsed our first million-dollar year in terms of revenue. Everything was great and then I burned out. I had to make some pretty big decisions post burnout in terms of how I was going to continue to build the business, what I wanted to do, what I didn't want to do anymore. January 2010was when I started blogging and podcasting. Now, I celebrate eight years online. I had no idea what it was going to do for me and my career and for my businesses. We fast forward now, three businesses, multi seven-figure annual revenue, almost 500 employees, sold out conferences, bestselling book, keynote engagements. I never thought I would be a keynote speaker in my life. A quarter of a million people downloaded my podcast every month. It's mad how things have just blown up since I got started in 2010. It just goes to show you that with a vision and a little bit of consistency and just by focusing on providing value, great things can happen.

BBR 244 | Rise Of The Youpreneur
Rise Of The Youpreneur: With a vision and a little bit of consistency and just by focusing on providing value, great things can happen.

You talk about vision ten years ago, back before the burnout, maybe a little bit longer than that, maybe when things were just getting started. What really was that vision like? What did you foresee yourself doing in ten, fifteen, twenty years?

I'm just a sales and marketing guy. At the very core, that's who I am as a professional. That's who I've always been. I dropped out of college when I was eighteen, much to my father's dismay. He didn’t talk to me for a few months. It was like, “If you're going to drop out, you drop out. You go sell that classified ad space. Welcome to the real world.”By the time I was 21, I was managing people twice my age. Clearly, I did the right thing. Even back in those days when I would listen to Zig Ziglar audiotapes, in fact, I was listening to Zig in my teens, it was quite obvious to me early on that I was going to be an entrepreneur. Looking back on it now retrospectively, it was quite clear that that was what I was going to do. It wasn't really until we built the company up to a certain level, had experienced a certain level of success from a growth and from a monetary perspective, and then that burnout came around. I was like, “There's got to be a better way to do this.”

Burning the candle at both ends, you're hustling. It was not something that I gave a whole lot of thought to in terms of where am I going to be a decade from now. One thing for me that did become quite clear early on, particularly when I started getting focused on the online side of things, was that I really enjoyed genuinely helping people, providing solutions to their problems in some way, shape or form. That’s what I was doing back in my sales career. You want to negotiate a front cover ad space, I'll solve that problem. I'll negotiate with you all the way. You want to build a profitable personal brand business, I'll help you do that, too. It's honestly being something that's been going on ever since day one, but I didn't really see it properly until 2010, 2011, and 2012 when I started to build the business of me through branding and podcasting and blogging and whatnot. People started coming to me saying, “How do you do it?”I just started answering questions and the rest is a little bit of history.

One of the things that I really respect about how you do you and how you stand out and stand up for who you are is you don't follow what's in fashion. When you're doing your live events, you're not going with the status quo, you're not doing what most people do, and you're actually speaking against it despite what some may want you to do. Is that something that always came naturally and effortlessly to you, or did you have some points of resistance where through your journey, were you waffling on, “How much do I give people what they want, and how much do I really focus in on what I want, and let the ones who want what I want really self-select and come to me and not worry about the others?”

I come from a corporate sales background. Status quo is key in that environment. When I was working in London, I used to go to the office everyday dressed like a golden gecko. I wore cufflinks every single day, tie, waistcoat. In the summer months, you take your jacket off and you just walk around your waistcoat. As I got older and I realized actually that the status quo is a lot BS and that it's actually quite boring as well, I wanted to do things my own way. Blogging and podcasting was really the incubus, the catalyst, for me to be able to really come out into my own. The funny thing was even when I first started podcasting and blogging, I still had that corporate type mindset where I wouldn't mess around on video camera, I wouldn't crack silly jokes or do silly intros on podcasts and all that stuff. You listen to my show now, some of the goofy stuff I do at the beginning of the show is what people are attracted to a lot of the time. I remember one time I grabbed my harmonica and I started playing like a blues riff in the middle of a podcast episode. Everyone comes up to me, “Have you got your harp with you? Can you play something now?”They never would've done that when I first started.

The status quo is fine up to a certain point, but then eventually you will hit critical mess with that and you have two options. You either continue with it and at that point you are bland and boring, or you fight it, you beat it up a little bit. You become your own person and you build what I call The Business of YOU, which is 100% unique because there's only one you, and then you take things up to the next level. That's what I decided to do and that's what I do through the pages of this book and with the Youpreneur community and the live events and all the rest of it. A perfect example of live events is for the longest time, Nicole, I have dreamt of holding a big business event in my hometown of London. Through the years I've held events in London, but probably the biggest head count I had was maybe 70 or 80 people, workshop style, mastermind style. We did a Tropical Think Tank here in the Philippines, massively successful, sold out every single year, high ticket item, $4,000 a ticket, etc., not for everyone. Now that I'm moving back to the UK with my family in the middle of this year, when I hit the ground running, we're going to do it. Screw it. Let's just Richard Branson it, “Screw It, Let's Do It.” Let's just find the venue. Let's book it. I remember my wife saying to me, “Why don't we just do it when we're living there already?” I said, “No. We hit the ground running, darling. We do it in 2017,we move in 2018. In 2018, we double the seat count. We double the attendance. It is what it is.:”Fine.”She went along with it.

The problem with the UK is it’s quite conservative, it's quite boring, it's quite stuffy. People that go to conferences, they just turn up with their note pads and take lots of notes and shake hands. “Tell me about yourself. Let's have a cup of tea and some biscuits,” and all that kind of stuff. It's very real. That's what it's like in England, but that's not me. I said, “I need to set the tone for this thing from second number one, the moment that we kick things off.”The event was in November. In September, I flew to the UK and we shopped. We spent the whole day filming footage of me literally running all over London, dressed in a Union Jack bow tie and Union Jack wais coat. The premise of what would become the introductory video to the entire conference was Chris is late for his own conference in his own hometown. The morning of the event, I was hiding up in AV booth and nobody saw me. We had Matthew Kimberly who is one of our keynote speakers, go up on stage and set the tone and said, “Nobody's seen Chris since last night. We're actually a little bit concerned. We’re not quite sure what's going on.”There was this whole thing and then he puts his finger to his ear and he says, “Hold on. I'm just getting confirmation. We've now got a live feed to Chris.”The video starts playing and it's basically me running all over London with Justin Timberlake's song, I Can't Stop This Feeling. It was great fun. I stormed in at the end of the video at the back of the room through the big doors. I'm still wearing the same waistcoat and bow tie and I'm out of breath and all the rest.

The people loved it and it set the tone for the entire event. They knew at that point that they were in for something very different in terms of a conference in London. I'm so proud that we put that event on because not only did I get the opportunity to genuinely live that dream of holding a big event in my hometown, but also when we first set the numbers, we only wanted 200 people. We said, “If we can get 200 people, that would be incredible.” We had over 350 people from 37 countries around the world. That just blew me to bits when we realized that there was that many people coming from that many countries. It just goes to show that fighting the status quo, being true to who you are no matter what you're doing and for whatever reason you're doing it for, if you're doing it for the right people, if you're doing it for your people, then you can't really go wrong. That part of your tribe are going to like what you're all about and what you do. We were very proud. It's something that we have big plans for the future in terms of growth and even expanding upon it with other smaller events as well.

For this episode, I’m actually sponsoring it myself. With that, I want to share with you about my one-day business breakthrough intensive. Let’s face it, no matter what stage of business that we’re at, there are always areas that could use a little bit of outside perspective. Without which, they hold us back from our goals. That’s why the most successful people in the world have people that they turn to in order to optimize their resources and get unstuck fast. I’m Nicole Holland, host of the Business Building Rockstars Show. This is one of the things I love doing for clients is helping them get really clear on the underlying issue that is manifesting all kinds of funky stuff in their life so that they can get more productive, more profitable and more joyful as quickly as possible so they don’t have to spend time trying to figure it all out. I have a unique way of honing in really fast on what’s going on, and spitting out a complete road map, step by step to get out of that sticky stuff. That gum that’s just holding them back. Whether it’s processes or lead generation or conversion or any number of things, that is one of my innate gifts and how I serve my clients at my highest and best.

If you would like more information about the one-day breakthrough, visit If you decide to join us, you can use coupon code BBRShow to take a whole $100 off of the tuition. Again, that URL to get all the details about my one-day business breakthrough intensive can be found at

I've been so enjoying the videos that have been posted. I just was watching one from Amy Landino, great footage and great talk. You had such rockstar speakers. You've already announced the keynotes for next year.

When I set the stage for the event, what actually happened initially was it was all about the event. It was all about the speakers and what we are promising from an event-attendee perspective. Then it became quite apparent quite early on in the ticket sale periods that we were getting a lot of international guests. I started reaching out to people via Facebook Messenger. I'm a big believer of P2P or People to People. I wrote about it in Virtual Freedom. I've been talking about it since 2012. P2P is real for me. It's how I build my business, people to people. I build my business with handshakes, hugs and high fives. I started reaching out to people verbally, not even messages, like verbally recording. ” Mike, I just noticed that you bought a ticket to the Youpreneur Summit and you're traveling all the way from Toronto. That's incredible. I'm just curious to know why. There are some great events in Toronto and in United States, you don’t have to travel that far. Why are you coming to London? What is it? Why are you coming to the Youpreneur Summit?”I’ll ask that question probably to 20 or 30 people from Europe, US, we had guys coming in from Singapore for this thing, and almost all of them came back and said, “It's in London. I've been looking for an excuse to come to London. Are you serious? This is great. You've got all these great speakers. It's in London. We trust you. We’re coming.”Then I went to work on really revamping the website for the event. If you go to now, you'll see clearly we sell London as a destination just as much as we do the event and everything that that has to offer as well. I think honestly, that's one of the reasons why we went well over our initial target of 200 is because we promoted the amazing city of London as well.

Are you're going to be in San Diego for T&C?

I will be there.

I'm going out there and that trip is taking longer than it would be to fly to London. When is it this year?

It’s November 3, 4, and 5. We're actually adding a third day option for those who want to spend one extra day of just sheer masterminding and business planning. The first two days are more conference style, a lot of speakers. We're going to have some panels this year which we didn’t do last year.

You don't do pitching of your things?

No pitching. I don't like that.

I'd love for you to talk about that because I do an online event. One of those things that I was firm in my decision that in my online event there was going to be no pitching. It was one of the things I really loved on your website, how it essentially says like, “This is something I don't believe in and this is what happens in most places. You will not experience it here. It is all pure high-value content.”

It's amazing what you can achieve in terms of your sales when you don't actually sell anything. Particularly online, people are tired of the free video launch and then there's the sales video and then you know, 100 emails in one week and all this stuff. People’s BS indicator is a way too sensitive nowadays. They can see it from a mile away. If you just consistently provide value and solutions to people's problems over a long period of time, they will eventually end up putting their hand in their PayPal account for you. It's really that simple. This year's events, and this is a great tip for anybody who does events, whether it’s in person or online, what we did on the beginning of the second day, the kickoff was [8:30]. At [7:30] AM, everybody got an email. It just said, “I hope you guys had a great first day here at the Youpreneur Summit. I hope you didn't drink too much last night, but if you did, don't worry, my staff got Advil. We will look after you.”

I just had a little bit of fun with it really. I said, “If you're interested in coming back next year, here's a link where you can get a discounted ticket up to midnight tonight. After that, tickets won't be on sale again until the end of March. See guys in about an hour from the stage. Bye for now.” That was it. We did nothing else. Out of the 350 people that were there, 147 people bought their ticket for next year's event right there and then on that day. In fact, actually we were getting people shouting out at me from the audience when I was on stage. “What's the URL again for the discount ticket?” I wasn't even mentioning it. They were all asking for it Other than that and a very quick little mention right at the end of the event as I was wrapping up, that was all we did. People were already in because of the value that we had provided them over and over again over the course of those two days. When you announce people like Jay Baer, Hal Elrod, Jadah Sellner, and Carrie Wilkerson as your four keynotes, they know you are not messing around.

When we curate and create an event that is of value, it's our responsibility frankly as the leaders and as the host and as the organizers to invite people to continue that experience with us beyond that. What I don't love in going to live events or going to online events is when each speaker has a special offering, “Run to the back of the room and buy my this in the next fifteen minutes.”

It’s the worst. I should also know as well that we had over 80 people out the 350 actually become a member of the Youpreneur Community within the weeks following the event as well, just organically. It just comes down to showing up, providing value, being authentic, and just showing people that you're the real deal. When you're up on stage telling a story about how you almost got arrested while filming a conference introduction video outside Big Ben, they realize that you're the real deal and they're going to listen to you.

BBR 244 | Rise Of The Youpreneur
Rise Of The Youpreneur: It just comes down to showing up, providing value, being authentic, and just showing people that you're the real deal.

Hopefully you'll come back and we can talk another time in depth about creating that virtual freedom by having a great team and how you have been able to help thousands and thousands of business owners and entrepreneurs do that over the years. I really want to make sure that we talk about your book, the new book that's just coming out now, the Rise of the Youpreneur. I'd love for you to talk a little bit about how that came to be, how you made that decision to write this book, and also maybe share some behind-the-scenes wisdom about some of the things you talked about that may be unexpected for a lot of people.

Before I do that though, let me talk very quickly about the virtual staffing side of things. The main message here of Virtual Freedom, which was my first book in 2014, is that as the business owner that you are, regardless of what level of business you're at, you should not be doing everything yourself. That's the main overriding message of everything there. Virtual Freedom is actually being described as the more practical version of the 4-Hour Work Week, which I love obviously. Tim's book was incredible, but to be called the practical version of it, it’s huge. It will genuinely take you step-by-step through how to build your business and run your business day-to-day and grow your business by working with a virtual staff. There's one little exercise right at the beginning of the book that we can throw out right now that people can actually do. It only takes ten minutes but it's a game changer. We call this exercise the 3 Lists to Freedom exercise. I did this myself when I was recovering from burnout. It was the catalyst for me to be able to start blogging and podcasting becoming the Virtual CEO that I am now.

Basically what you do is you get a piece of paper, you draw two lines in it, creating three columns. Column number one, you write down all the tasks that you hate doing on a daily basis. This is the stuff that you procrastinate on over and over again. When you drag and drop on your calendar digitally, “I'll do that tomorrow. I'll do that next week,” that’s the stuff you put in this column. It’s the stuff you hate. Column number two is a list of all the things that you struggle doing. It’s stuff that you can't do. As entrepreneurs, it's tough for us to actually write anything in that column because we think we're great at everything, but the reality is we struggle with a lot of different things. That’s column number two. Then the last column is by far the most important and the hardest column to fill up because you could actually really like doing these things, you could actually be very good at doing these things, but the big overwhelming 800-pounds Silverback Gorilla of a question is, “As the business owner, should I actually be doing these things?” It’s a big one. When you complete those three lists, what happens is you create ultimately your roadmap or your blueprint to actually go ahead and start delegating to virtual assistants and building a virtual team. I wanted to give that real quick because it's important.

I legitimately and sincerely wish I knew about, not just of you, but really how you are serving and supporting. When I got started, I had been inundated with so much messaging. I was just trying to figure out where to focus and everything. It's so hard when you just don't know. I wish somebody had really tapped me on the shoulder sooner and said, “Nicole, just go read this blog from Chris Ducker. Just go take this particular piece about handling your email. Just this one thing can change your situation so many times over.” I've been a great recipient of what you do and I have felt like I wasn't getting the messaging well enough from people who are saying strongly enough like, “You don't even have to buy anything. Just go there. This is what you need to solve your problem right now.”It was a no-brainer for me once my brain was opened. Once I got it, I was like, “Sold,” and it's been amazing. If you go to, you can learn more about the Virtual Staff Finder and what these guys are doing. You can reach out to me personally for my experience with it. Let's jump into Youpreneur a little bit.

When I said I was going to write this book, a lot of people were actually quite surprised because I said that Virtual Freedom is going to be the first and the last book I'll ever write. If you talk to any author by the time they're done writing and marketing their book, they're never going to write another book again. Just like with Virtual Freedom, I felt like at the time when I did write it and get it out there that I needed to because it was a proven entity. Everything in the book worked. I've got to share it with my peers, with my fans, followers, customers, and the whole lot. With Rise of the Youpreneur, I feel absolutely even stronger about it because this has been the big part of my life for the last four years. Since Virtual Freedom came out and wrapped up, I was actually in the US on a speaking tour promoting the book when I coined the term “youpreneur,” and wrestled and negotiated the domain name from a squatter who had been sitting on it for like ten years or so. I got the domain and then obviously, I did nothing for an entire year other than just figure out what it was actually going to be. It ended up being a membership community, which is where I met of our mutual friend, Mike Morrison. I’ve grown it since then. Now we've got hundreds and hundreds of people in the community.

The book has come about because of the community, because of the work that we did inside the community to fill up the gaps in our training content that was initially there when we launched in late 2015.We then re-launched in mid-2016 with what we called our Youpreneur Roadmap. That was set up into three main sections, the building, marketing and monetizing. It was probably about the end of 2016, we were updating the roadmap with all the new content that has been published that year. I started to look at it. It was the weirdest thing. Did you ever see those films where you get like, “I can't remember who used to do this,” or it might have been Beautiful Mind with Russell Crowe where the equations come out off of the board and they start spinning towards him and everything in the movie like that special effect, it was like that. I was looking at the roadmap and all these things were coming out and forming into different sections. We rejigged the entire roadmap based on what I saw and we got incredible feedback from it.

People genuinely are actually consuming the content front to back, top to bottom for the first time ever, even though some of them had been in there for a year already. They never really looked at any of the content. They were just there for the forums. Once everything had been very clearly set out, I looked at it and I thought, “This is actually a book ready and waiting to go right here. I don't even have to write it. It's written already. I just need to basically just fashion it into book form.”That's what I did. I worked with an editor. We did twelve hours of interviews with me. We pulled tons of value from all the different workshops and videos and all the rest of the people. Guys like Gary Vaynerchuk, Amy Porterfield, all these real, serious personal brand entrepreneurs, and we put it all into the Rise of the Youpreneur. We called it, The Definitive Guide to Becoming the Go-To Person in Your Industry and Building a Future-Proof Business. I really do feel like it is the definitive guide. Regardless of how many other books might be out there on personal branding, nothing will walk you through building a genuinely profitable business from your personal brand like this does

I'm so excited to see that and to get my hands on it. For everyone who would also like to do that, they can go to

It's up on Amazon as well.

Go check this book out. Get it on Amazon, give it a read, go leave that review and let Chris know what you love most about it. Let other potential readers understand the difference between just another book and this roadmap and how impactful it is. It really does make such a difference for us. Everyone here are entrepreneurs. They are building their brand and you always want to think about or at least I recommend always thinking about whether you're doing podcast guesting, whatever you're doing, always think about, “How would I want to be treated if I were in this person's shoes?” Definitely go check it out. Write a review, love it up, and share it with your friends. Chris, thank you so much for being here with us.

It was all my pleasure. It was great to come on.

Resources mentioned:

About Chris Ducker

BBR 244 | Rise Of The YoupreneurChris is a serial entrepreneur and author of the bestseller, “Virtual Freedom”, and author of his latest book, “Rise of the Youpreneur”.

Originally from the UK, Chris has lived in the Philippines for 17-years, where he has founded multiple businesses, which combined house over 450 full-time employees.

He’s a trusted international business mentor, keynote speaker, podcaster, blogger, as well as the founder of

Chris hosts the annual Youpreneur Summit, which is held in London, England each November and is the self-proclaimed ‘Proudest Brit’ doing business online!

Thanks to Megan Hall for supporting the Business Building Rockstars Show.