How I Built a Six-Figure Recurring Revenue Business

UPDATE: This is now a seven-figure a year business.

I’m going to show you how I went from unemployable university dropout to building a successful online business with recurring revenue. And I promise, no horse shit. It's been a heck of a ride, and the aim of sharing this story with you is to give you the confidence and starting points to build some recurring revenue into your business, so you have more choices in life. 

How I Stopped Trading Time for Money and Regained my Freedom

By the way, the photo above is of Boracay in the Philippines. It regularly gets voted in the top ten best beaches and best islands in the world. I’ve been to Boracay and can vouch for it. It is spectacular.

Yes, I am a university dropout.

Yes, I have created well over $1 million $2.5MM in recurring revenue through selling courses on the Internet. I don’t have a boss, and I can work whenever and wherever I choose. I consider myself very fortunate to have the lifestyle I have.

I would like to help you build some recurring revenue in your business, so you have more choices in life. 

We’ll get to that, I promise.

However, first I am going to give you a brief history, so you have some context. Stay with me, because the details in this story reveal how I came to be an online entrepreneur.

I grew up in the working class northern suburbs of South Australia and went to a very average public school where most of the teachers wanted to be there even less than us students. A handful of my teachers was fabulous. Some were depressed alcoholics. I hated school. I barely passed my final year with a score of 65/100 and went on to university to get a Bachelor of Educational Theatre.

What I wanted was to be an actor. However, nobody thought that was possible, so I was convinced to become a drama teacher. I lasted eight months and dropped out. The following year, I moved to Melbourne to pursue my dreams of becoming a rock star. I supported myself by working as a travelling sales rep selling hair care products to hair salons. This is all a true story.

Quarter-Life Crisis

When I was 26, I had a meltdown. I was miserable and couldn’t work out why. A friend told me to change one thing in my life at a time until I figured out what it was that was making me unhappy.

Within a week I had quit my job, left my girlfriend, quit the band I was playing in and moved into a one-bedroom flat in St Kilda, a very colourful inner city suburb of Melbourne. I was surrounded by sex workers, homeless people and drug addicts. And it turned out one of my heroes at the time, the lead singer in a local glam pop band, lived above me.

I had about $6,000 in my bank account, which I burned through pretty quickly. I borrowed money from my folks to pay the rent and had no idea how I was going to survive or get happy. The bathroom and my walk-in wardrobe were damp and mouldy. Today, I can reflect on this time of my life and honestly say it was the moment I hit rock bottom.

I Need to Drive the Bus

Amid this chaos, I learned one very important lesson that would serve me very well: I was highly unemployable.

I hated authority, and in all my previous jobs (mainly travelling sales work), I was convinced that I could find a better way of doing things and that everyone around me was an idiot – and trapped. Of course, I was young and naive, and I had a lot to learn.

To pay the bills, I managed to talk myself into a gig as a contractor teaching corporates how to use Microsoft Office products. It was horrible – partially because Microsoft Office products rarely behave the way they are supposed to according to the training manuals, and partially because the dodgy bloke I was contracting for was terrible at paying his bills on time.

However, it forced me to register my first business name, learn how create an invoice, and get my head around the basics of running my own business (it also taught me how to hire a debt collector and threaten somebody with bankruptcy in the small claims tribunal, a skill I have thankfully never had to use again).

I photocopied and framed the first ever cheque I received in my business name. It was for $1,700.

Location, Location, Location

The skanky box I lived in happened to be about 100 metres down the road from a well-known commercial radio network in Melbourne. One of the on-air DJs lived in the same block of flats as I did, and we got chatting in the car park one day. Long story short, he put me in touch with one of the creative writers at the radio station, and they started training me as a voiceover artist. You know, somebody who reads the commercials for radio and television.

This was a huge turning point for me, as it turns out I’m quite good at reading the commercials, and this kind of work pays pretty well and doesn’t require a lot of time.

So I was earning enough money to survive, and I had quite a bit of spare time on my hands – a dangerous combination.

I used, this time, to discover that the Internet was a very powerful business tool, and my mind was opened to the possibilities all these new connections the internet afforded me.

It was 2001, and little did I know that my journey as an entrepreneur was just beginning.

Tip # 1: You do not need to be highly qualified or have lots of money or resources behind you to build an online business with recurring revenue. You just need to be really stubborn. (And being highly unemployable helps.)

My First Sale

I really need to drive the bus.

So between 2001 and 2005 the glory days of earning a good living as a voiceover artist taught me that sitting around waiting for the phone to ring made me vulnerable. I wanted more control over my income and I had figured out how to publish websites to promote myself as a voice artist and singer. In 2006 I published a few websites for friends in the post-production and film industry in Melbourne as favours and as a way of learning the craft. They were horrible, and I would like to take this opportunity to apologise to anyone who ever visited them.

In March of 2007, a local record company offered to pay me $1,200 to build them a website, so I decided I better learn how to write HTML and CSS. I had just landed a six-week gig singing at the resort on Great Keppel Island – a tropical island off the coast of Queensland in north-east Australia. Despite the crappy dial-up Internet, this was the perfect opportunity for me to study and learn how to build websites.

I realised very quickly that the record company would want to update the new website, and I did not want to be responsible for making that happen on a weekly basis. I decided I would build my very own content management system. A friend of mine put me onto PHP and MySQL as a good open source tools to use. I had no idea what she was talking about, so I bought a couple of cookbooks and got to work.

For six weeks I studied, hacked code and refreshed the browser a gazillion times a day and played “Brown Eyed Girl” and “I’m a Believer” to the drunken punters at night. When I returned to the mainland, I had built a working content management system and delivered the website to my client. Then, I had to teach them how to use my clunky system. To my surprise, even though I had built their website in a way that allowed them to update it themselves, they were not particularly interested in learning how to do it. This was a very important lesson for me that would eventually pay off.

Teach a Man to Fish

A friend of a friend had been trying to convince me to use a piece of software called WordPress to build websites, but I was insistent on making my own content management system. During some downtime after returning to the mainland, I decided to download WordPress and give it a spin. I realised that what had taken me six weeks to code, I could have achieved in about half an hour if I had taken his advice.

I made the decision there and then to build my next website using WordPress. Another friend of mine owned a post-production studio where I had been doing some voiceover work, and he needed a new website. This was my perfect opportunity to get to know WordPress. I made an educated guess that even if I built the website on WordPress (which allowed them to make changes quite easily) I would still have to train them in how to use the processes.

While building the website, I managed to compile a 100-page document with over 80 screenshots explaining how to use WordPress to manage the content on a website. I deliberately kept all the instructions and screenshots as generic as possible so that I could reuse this document for future clients. I was totally scratching my own itch.

I delivered the new website to the client along with a 100-page PDF, which I called the “Website User Manual”. I even printed a copy out for them. They were so impressed by the user manual that it prompted me to share it with my buddy who had been trying to get me to use WordPress for months.

This is what the same document looks like today.

My buddy Brian was impressed with the amount of work that had gone into the user manual. He suggested we turn the manual into video tutorials and make a plug-in that we could sell to other WordPress developers. I volunteered to make the videos, and he worked out how to build the plug-in.

A couple of weeks later, we reconvened, put our new plug-in through its paces, and threw together a very quick website to start promoting it.

We also decided that it would need to be sold on a subscription basis because we would need to keep updating the videos whenever WordPress was updated.

Our sales checkout form was thrown together pretty quickly and seems quite ugly by today’s standards, but it did its job: it allowed us to accept money from our customers.

We had no email list and no email marketing software.

We just emailed people who we actually knew from our Gmail contacts: people who had helped us build websites, other WordPress developers and agencies, and people who organised local WordPress MeetUps.

Oh, and Brian had the genius idea of making a free plug-in to allow WordPress developers to re-brand WordPress and turn it into a white label CMS. He wrote that plug-in, and we submitted it to the 

WordPress plug-in repository. It was called White Label CMS (we have a habit of naming products based on exactly what they do).

The plug-in was accepted, and WordPress developers all over the world started downloading it because it fulfilled a very specific need for them. Upon installing the plug-in, a few settings need to be configured, and on that settings page is an image advertisement for the Video User Manuals plug-in. The two plug-ins perfectly complement each other. This small advertisement in our free plug-in has been one of our most successful marketing strategies to date.

We also placed a signup form for three free e-books to help users build a better business as WordPress consultants on the settings page. This has been the biggest generator of leads for us and has allowed us to build a modest email list of around 9,000 in three years with ZERO advertising.

At the time of writing, the free White Label CMS plug-in has been downloaded over 335,000 times.

Our first sale for the Video User Manuals plug-in came from a customer in Western Australia named Kelly Exeter.

I hope you’re paying attention, because this is how you build an online business and create recurring revenue.

Tip #2: Provide recurring value to a targeted group of people with a common need and make sure that value exceeds your asking price. Oh, and give a bunch of awesome stuff away for free.

Focus, Focus, Focus

Just after we launched the plug-in, I landed a large website project that I couldn’t handle on my own, so I teamed up with a designer and we decided to build a web design agency.

For the next three years we hustled, experimented, built processes, hired staff (locally and offshore), won projects, lost projects, used various CMS platforms, came back to WordPress, built a good portfolio of clients, wasted tons of money on stuff we didn’t need, built recurring revenue, made video blogs, spoke at conferences, and learnt a million lessons along the way. By the middle of 2012, I was miserable.

In the meantime, Brian and I would meet on Skype for around two hours every Tuesday and check in to see how our little plug-in was doing. I was unhappy in my web agency business (primarily because my business partner and I couldn’t agree on anything and the long debates just wore me down), and I was convinced that with a little more focused effort, the plug-in could probably support us full time. I was recently engaged and had just taken out a decent mortgage to buy our apartment. My fiancée was studying psychology at university, so we were essentially a one-income family.

I was terrified of losing revenue from building websites for clients, but I also knew that if I didn’t focus on one business or the other, I would properly screw both of them up. My fiancée also threatened to change the locks if I came home complaining about my web agency business once more.

You Can’t Be Half Pregnant

Around this time, I had a meeting with my accountant, who told me that I was essentially half pregnant with two business partners. His advice was to roll the dice and focus 100% on one business. I wanted to move more into selling digital products, and my business partner in the web agency and I could hardly agree on anything by this point, but the plug-in business was not generating enough revenue to support Brian and me full-time.

I received a promotional email from Ed Dale, who was offering business mentoring. It took me about three weeks and several emails and tweets to get Ed’s attention and convince him to mentor me. I tried to deposit money into his bank account twice and failed because he had given me the wrong details. I was determined and said I was happy to meet him for lunch and hand over the cash if need be. Third time lucky – the money went through and I had myself a mentor.

When I met Ed for lunch, he was accompanied by his friend and colleague Guru Bob. I later realised this was probably for Ed’s safety, as he has quite a public profile on the Internet, and I could have been a serial killer for all he knew. The upshot of this was that I had two immensely respected people telling me the same thing my accountant told me. They both made it perfectly clear that while I was trying to build two businesses, I was dramatically reducing my chances of succeeding in either of them.

They helped me get clear and unstuck. I left that meeting and phoned Brian on the way back to my office to tell him that I wanted to go full-time in the plug-in business. He was thrilled to hear this, but we had no idea how we were going to make it work.

Just as I was dissolving the web agency partnership, I was fortunate enough to meet Dale Beaumont, who had seen some of my content online and reached out to me. Dale ran a community of over 200 small business owners who met four times a year at a conference called Business Blueprint. He asked me to speak at his next conference about online marketing. This connected me with enough people to pick up consulting work to support myself as a freelancer while we tried to scale the plug-in business.

Tip #3: This is a key point. The fact that I had published some video content and blog posts based on what I had learnt led me to a connection with Dale Beaumont and over 200 potential leads. Other leads approached me because they could see I was speaking at conferences and therefore, must be knowledgeable in my domain. This is Content Marketing 101.

Our Flagship Story

With a new focus and some time to devote to the plug-in business, Brian and I decided to sponsor some local events, and I was asked to speak at WordCamp Melbourne in early 2013.

I had spoken at similar events in the past. My presentations had always been based on how to improve one area of a professional’s business. This time, I wanted to give the most engaging and entertaining presentation I possibly could.

I came up with the title “101 Ways to Elevate Yourself and Demand Higher Fees”.

Brian and I fired up a Google spreadsheet and started collaborating to develop the 101 ways a WordPress consultant could make their business offering stronger and therefore, demand higher fees. After a few weeks, I had built a keynote presentation with 103 slides (101 with two bonuses – hey, I’m a marketer) and rehearsed it to make sure it fit within the 45 minutes I was given.

I was the first presenter on the day after the opening keynote, and just before I hit the stage, I was told I had 25 minutes, not 45. Do the maths. That’s four slides per minute or one every 15 seconds. I still managed to give a great presentation to a packed room. The ideas that we presented sparked a lot of conversation over the coming weeks (particularly later that night at dinner, when a bunch of us were discussing how we wished there was more business training available for us WordPress freelancers).

I ended up recording a video presentation of my 101 ways and posted it online a couple of weeks after the conference. You can see the full “101 Ways …” presentation here on Vimeo.

Opportunity Plus Preparation Equals Luck

The video of the “101 Ways …” presentation got shared around a lot on the Internet. I’m not going to use the “V” word – but it got shared quite a bit and resulted in over 10,000 views of the video and some earlier presentations I’d done on YouTube, Slideshare and Vimeo. I made ZERO effort to promote this content, apart from uploading it and writing a relevant description.

This traction motivated me to try something. In the spirit of the Lean Startup, I decided to test whether or not our existing email list of around 9,000 would pay for business coaching from us.

The quickest way to do this was to build a sales page using Unbounce to sell tickets to a webinar. I plugged the sales page into EventBrite to manage the ticket sales and GoTo Webinar to manage the webinar registrations. We priced the webinar at $197 and made early-bird tickets available for $97. I told Brian that if we sold 10 tickets, I’d refund them and pretend it never happened. If we sold more than 10, I’d turn up and run the webinar. I was secretly hoping for 30 sales.

We sold out of our 50 early-bird tickets within 24 hours and then released Round 2 tickets for $127 and finally Round 3 tickets for $197. We made a sale of $11,500 in 48 hours, and we had ourselves a webinar to build.

At this stage, I had not prepared one slide.

We ran the two and a half hour webinar (which was epic, by the way) and I taught 84 people everything I knew about running a WordPress agency. I surveyed all 84 registrants after the webinar to ask them what they wanted next, and 55 responded with some very common desires and pain points.

You can see the original survey here.

After sifting through the responses, I had a Skype call with about five or six of our customers and asked them point blank to help me design the business coaching programme, from features and frequency to content and pricing. They were willing to talk to me for free.

I also asked them to tell me whether they would buy it if I came back in two weeks’ time with what they asked for. They all said yes.

So I went away to a friend’s farm for a few days and made some sales videos and a welcome video and built a membership website.

Two weeks later, we had a new product. We opened the doors to our business accelerator programme WP Elevation for 4 days only, and 55 people joined at $97 per month.

Collaborative Content

I started a podcast pretty quickly after we launched WP Elevation and began reaching out to influencers in the WordPress space, interviewing them about their success and their struggles. The great thing about a podcast, or any other form of content that involves a guest, is that they will usually share it with their audience, which brings fresh eyes to your website. It’s the quickest way to expand your reach.

If you don’t have the skills or courage to start a podcast, then send questionnaires and publish the answers on your blog.

The podcast attracted traffic, which in turn attracted signups for our free e-books, which in turn resulted in more and more people joining our programme.

In the meantime, I was asked to present the “101 Ways …” keynote at WordCamp Phoenix via video link up and the following year flew to Chicago to present it in person at WordCamp. My video link up on Phoenix was discovered by a guy named Rich Thurman, who tweeted to me afterwards to talk about marketing automation (he’s an Infusionsoft Certified Partner).

Long story short, Rich introduced me to Ryan Deiss from Digital Marketer, who asked me to speak at his Traffic and Conversion Summit conference in Australia in 2015. At that conference, I was spotted by the guys from The Entourage, who asked me to speak at four events for them in Australia and New Zealand. I also met Greg Cassar, who asked me to speak at his Digital Marketing Summit in Sydney.

I accepted all of these invitations. In the course of speaking at these events, I have met some of the most inspirational entrepreneurs and continue to nurture meaningful relationships with them.

These entrepreneurs include Tammy May, who started My Budget; Glenn Martin, the inventor of the Martin Jetpack; Michelle Bridges, host of TV show The Biggest Loser and founder of the 12 Week Body Transformation programme among many other ventures; Andrew Morello, winner of the first Australian Apprentice TV Show and Head of Business at Yellow Brick Road; and Jack Delosa, founder of The Entourage, Australia’s largest educator and community of entrepreneurs.

Tip #4: All of this podcasting and presenting and speaking with others is ‘collaborative content,' where two or more publishers of information share each other with their respective audiences – a trend that has been adopted quite heavily in the music industry over the last couple of years. It is a valuable technique to expand your reach and positioning. 

Take a look this recent snapshot of the iTunes charts and notice how many collaborations there are:

All of these things combined, along with my stubborn determination, extreme unemployability, and the processes and team we have built have now put me in the luxurious position where I am earning more than I have ever earned before. I don’t have a boss and I can pick and choose exactly what I want to do and when.

I work extremely hard. I can start whenever I want and knock off whenever I want. I can take as many holidays as I like. But the truth is, I work more hours than I have ever worked in any job because I love what I do. The feedback and testimonials we get from customers every day makes it all worthwhile, and is what gets me out of bed every morning.

I Would Not Trade My Business For Anything

So I know what you really want to know is what you should do next. Here are a few ideas, in no particular order, to get you started:

• Start building a list of emails now.
• Make people an irresistible offer to join your list.
• Give away as much free stuff as you can without giving away the farm. If in doubt, give away the farm.
• Talk to your list and ask them what they want. Offer them what they want and ask them to buy it. Then build what they want once they have committed to buying it.
• Don’t quit.
• Partner with other companies that are serving the same audience with complementary products.
• Produce videos.
• Speak at events.
• Don’t quit.
• Partner with other companies that are serving the same audience with complementary products.
• Produce videos.
• Speak at events.
• Don’t quit.
• Give away free software.
• Don’t be afraid to buy traffic, just find a way to pay for it.
• Don’t quit.
• Don’t try to build a company just to sell it – it won’t keep you motivated, and the chances of selling it are ridiculously slim. You’ve got more chance of writing and releasing a number one hit single.
• Start a podcast.
• Unsubscribe from anyone’s list unless you actually look forward to their emails. Email marketers are all trying to sell you something eventually. I know because I’m one of them.
• Reach out to mentors.
• Admit you don’t know what you’re doing.
• Don’t buy software apps unless you absolutely bloody need them.
• Only use technology and automation when you are overwhelmed and can no longer do it manually.
• Don’t believe everything you read and don’t believe that other people are as successful as you might think.
• In my experience, there is a lot of horse shit on the Internet.
• Publish your thoughts and opinions on the Internet with no expectation that anyone else is going to read them.
• Learn stuff and publish what you are learning. It helps you learn it and it keeps you accountable.
• Don’t quit.

Here are some people you might want to follow and learn from because they give away amazing value, and they don’t bullshit (I either know these people personally or have bought several of their products):

• Seth Godin
• Guy Kawasaki
• Neil Patel
• Nathan Chan
• Rand Fishkin
• Michelle Bridges
• Dale Beaumont
• Jack Delosa
• Tammy May
• James Schramko
• Frank Kern
• John Lee Dumas
• Tim Reid
• Dan Norris
• Brian Clark
• Amy Porterfield
• Jeff Walker
• Brendon Burchard
• Pat Flynn
• Andrew Warner
• Jeff Bullas
• Ryan Deiss
• Chris Ducker

I wish there were more women on this list, but it seems my experience in online business and marketing has been dominated by men. If you know any amazing women in online business and marketing who I should follow, please let me know.

Don’t Quit

“Hit the publish button,” as my friend Bill Belew says.

Don't quit, don't quit, don't quit.

I’d love to hear about your story and your journey towards creating an online business with recurring revenue. Maybe you’re just starting out or maybe you’re on your way and you’re trying to scale it. Wherever you’re at, feel free to get in touch, and hopefully we can all help each other achieve our dreams.

Hit me up on twitter @troydean

Stay curious and make some noise.