2016 Year In Review

By Brennan Dunn

Since 2012, I’ve been writing annual reports and making them public.

In these reports I do my best to sum up what went well over the last year, what didn’t, and what’s next for me.

I write these reports for myself—they serve as time capsules that I can look back on to see how the business has shifted and occasionally taken big leaps forward over the years.

But I make these reports public because I owe to you, customers and readers of Double Your Freelancing (DYF), to let you know what’s next for us and how that will impact you and your business.

When I first started writing these reports, I was just starting out selling my first products.

I wanted to help those who were thinking about building and launching their own products learn from my mistakes and to use me as inspiration. I owed it to that next generation of creators because I followed in the footsteps of those who were a little bit ahead of me, and I wouldn’t be here doing what I’m doing today had they not shared their experiences publicly.

Now, 4 years later, my business is doing 7-figures annually and there are a lot of people involved in the success of DYF. And while this might not be as inspiring as past reports have been in helping someone who’s just starting to build a business, hopefully seeing the big picture (from 2012 -> now) will show what’s possible in just a few short years.

But, more importantly, this year’s report is for you—the DYF customer or subscriber—because you are our shareholders.

It’s because of you that we do what we do, and we rely on your feedback to help us figure out what’s next for the company. Your success is our success.

A brief history of Double Your Freelancing

Whenever I go on a podcast, I’m asked to give a brief overview of who I am and what got me to where I am today. If you’re new to the DYF community or don’t dedicate as much headspace as I do to Brennan Dunn’s history, here’s how we got to where we are today:

  • 2006: Dropped out of college to start a company with my friend. We generated exclusive leads for mortgage brokers (sexy, right?)
  • 2007: The housing bubble burst, we went out of business, and I found a job coding PHP at a local agency.
  • 2008: I was now CTO of the agency, but with Baby #1 on the way I found myself moving to Virginia. Forced to quit my $105k/year job and start freelancing.
  • 2009: Expanded my freelancing business, leased an office long before I needed one, and hired my first few employees. I guess I was now an agency owner?
  • 2011: Started building Planscope, an online project management tool for agencies and freelancers. I thought this would be my ticket out of consulting.
  • 2012: Exited my agency (read more here) to focus full-time on Planscope.
  • 2012: I started creating content for freelancers that I thought would help sell Planscope accounts, and against my better judgement wrote a short little ebook, Double Your Freelancing Rate.
  • 2013: Created a few more products and courses, recreated DYFRate to be a much bigger and better online course. (read more)
  • 2014: All of my stuff was floating on a bunch of different domains (,, …) I moved everything over to Continued splitting my time between managing my training products and Planscope. (read more)
  • 2015: I launched Double Your Freelancing Clients (now known as the DYF Academy) and continued managing my other products. I was reaching my breaking point in trying to run a software company AND a training company.

Enter 2016…

I sold Planscope

I was having a really hard time running DYF and Planscope simultaneously.

Two sets of customers, two separate support inboxes, and the switching back and forth from owning a training business to owning a software business was really taking a toll on me.

And Planscope customers were getting a bit miffed.

I wasn’t really shipping any new features. I was really bad at responding and mitigating bug requests, and because this was a tool that their clients and teammates would use those bugs were starting to hurt the reputation of some customers.

At the end of 2015 I decided to sell Planscope, and the sale happened in the Q1 of 2016.

Things took a lot longer than I expected, but that was largely my fault. I mixed Planscope expenses and revenue with DYF. After all, they were all umbrella’d under the same parent company.

So when my broker, FE International, did their due diligence I had to dig up 12 months of bank and credit card statements and figure out what was Planscope and what wasn’t. And since I’d often use some services, like hosting, where I’d pay a single bill that would be for both DYF and Planscope… yeah. It was a mess.

Lesson learned: If you want to build a business that you could one day sell, silo its finances once it gains a bit of traction.

“Me” -> “We”

When I started DYF, the articles and products that I created were largely based on my own anecdotal experience.

I was the center of it all. I did everything.

And, to be perfectly honest, I loved it. I like that people interacted with me personally, and not support tickets from a faceless business. I liked telling people that emailing support meant sending a note to my personal inbox.

But we’re now 10,000+ customers strong.

Having me handle everything meant that customers would get shortchanged because I’d get overwhelmed with the amount of stuff that greeted me in my inbox each day—and if I was writing a support email, that meant I wasn’t writing a new guide or article for DYF, which started to really bother me.

DYF now has conferences, quarterly retreats, more than 200 groups that meet monthly around the world, a growing portfolio of products and courses…

There’s no way I can handle it all myself.

I’ve been working closely with a core group of people, and their involvement with DYF has started to scale up considerably in 2016.

Here’s a list of the people who help contribute to the growth of DYF:

  • Kai Davis
  • Jessie Goodell
  • Laura Elizabeth
  • Naomi Bush
  • Craig Hewitt
  • Annabelle Dura
  • Eleanor Edwards
  • Shai Scheter
  • Andy Baldacci
  • Philip Morgan
  • Jonathan Stark
  • Gina Horkey
  • Kurt Elster
  • Mojca Mars
  • Matt Inglot

We gave Google what they wanted

Traffic growth this year has been great.

2016-12-19 at 11.06 AM

We’re now getting around 5,000 organic visitors a week, with weekdays getting close to 1,000 a day.

That’s up more than 100% over the same period in 2015.

We’re also adding about 2,000 subscribers a month to our list (for the first 3 quarters of the year, we were averaging ~1,000 new subscribers a month.)

2016-12-19 at 11.16 AM

We started the year at 30,767 subscribers and today (December 19, 2016) have 36,136, or a 17% growth in list size. We’ve also been getting a lot less unsubscribes, which is due to minimizing list-wide broadcast emails in favor of more personalized and segmented campaigns.

We also hit 10,000 total customers. Holy s*)@!

So how’d we do this?

What “SEO tricks” did we use? What did we do to game the system?

We increased the human-readability of the website.

The homepage used to be the 5 most recent articles we published. Who does that help? Maybe someone who is really on top of our content and wants to see what we just published—but that’s it. It doesn’t help someone who stumbled across our website for the first time.

We put together an upside-down home page that promotes our most popular free course, Charge What You’re Worth. It also highlights a few of our most popular articles. The homepage is far from perfect (it’s not yet tailored to anyone who’s already gone through the free course and has no need to enroll again,) but it’s proven effective.

Additionally, we created a topics page that lists out each of our content categories and highlights the top 3 articles in each. From this page you can access every article we’ve published.

This means that with just 2 clicks you can access any article we’ve ever published.

Home page -> topics area -> an article.

Before we did this, you’d need to wade through pages of 5-article-at-a-time summaries to find all of our content. Not very useful, but it’s the way most blogs are designed.

We tried to consider the reader at every stage.

If someone just found our homepage, what should they do next?

If they Googled an article of ours, what should we promote? (Hint: not a product.)

The current structure of the website is just the 2nd iteration. We’re working on a complete redesign, and I’ll be sharing the full details of this redesign next month.

Invested heavily in personalization and intelligent automation

You know how it important it is to choose a niche…

But have you ever thought about why niching is so important?

It’s because you’re able to speak directly to someone. When you’re not positioned, you end up speaking to no one specific. Which means you’re requiring that people mentally tie together what it is you’re saying with what they actually need to determine if you’re able to help.

DYF serves anyone who sells services to businesses. And as our reach has grown, so has our diversity. We’ve just started doing some progressive profiling of subscribers, and in the image below you can get an idea of who our community is made up of.

2016-12-19 at 3.02 PM

Not everyone wants the same thing from us, either. Some are looking for more in-depth business tutorials while others want more 1-on-1 support.

2016-12-19 at 3.07 PM

So where am I going with all of this?

We’ve started personalizing our on-site experience.

When it comes to developing a subscriber profile, we look at 3 factors:

  • Behavior. What kind of content has this person read? Have they visited key pages, like the DYF Academy? Do they listen to the podcast? What can we tell about this person based on what content they’re engaging with most?
  • Demographic. What have they told us directly about themselves? We’ve built a survey widget (that you’ve probably seen on this site) that cycles through a series of questions, with followup questions determined on already supplied answers. We also have worksheets in our email courses that helps us better understand our subscribers.
  • Purchases. What have they bought, joined, or attended? This tells us a lot about who someone is and what they want from us.

Using these 3 factors, we’re able to better customize the emails we send and the content we show on our website. We’re slowly starting to utilize this data, but here’s what we’ve done so far:

  • Personalized navigation and call-to-actions based on who someone is and what they’ve done.
  • Enter people into a “promo loop” sequence for a particular product when key events take place.
  • Customized the content and examples in Charge What You’re Worth based off business type and goals.
  • Personalized the sales page of DYFRate.

I’ll be sharing what else we’ll be doing with this data in a later post. It’s unlike anything you’ve ever seen before.

Launched the DYF Academy

We launched our most ambitious project to date this year, the Double Your Freelancing Academy.

It’s a 7-month intensive program that provides individual support and training to up to 30 new students a month.


Unlike our self-study courses, the Academy is a program with a lot of moving parts and overhead.

The first cohort of the Academy kicked off in August, and we’ve had a perfect, 100% retention rate from everyone we’ve brought onboard. So far, everyone is pushing forward and making great leaps forward.

A few things we’re doing right:

  • Mandating an application and 1-on-1 video call in order to join. A lot of programs allow you to join if you can click a “Buy Now” link, which means the only way of qualifying a candidate is financially. This allows us to make sure that those who join are prepared to join, and those who aren’t are pointed in the right direction for the time being.
  • Bi-weekly Masterminds led by a personal support rep. A condition of joining is blocking out the time to attend live sessions with your Success Coach.
  • Recognizing that our students are also running their businesses full-time, and making sure we don’t overwhelm. By stretching the program out over 7-months, we’re able to help students build a new business while running their current business.
  • Having built-in feedback loops that allow us to see when someone’s at risk of going missing-in-action. Every student is assigned a Success Coach, who’s their cheerleader-in-chief, first line of support, and a former student of the Academy. We rely on our SCs to help bring to our attention anyone who needs a little help… and it’s working.
    2016-12-19 at 11.39 AM

Is it perfect? Far from it.

But we’re learning. And, most importantly, our students are succeeding.

We see the DYF Academy as being the program that we’re ultimately known for. And in 2017, we plan on taking the Academy to the next level.

Hosted our first European conference (and hosted another in the US)

Last June we hosted our first DYFConf Europe in Stockholm.

It was a huge risk, because we weren’t sure if Europeans were different than Americans when it came to attending conferences, especially when you don’t have an employer footing the bill.

On top of that, we hosted it at an all-inclusive Japanese resort in Sweden, and we had to collect a 25% VAT. This meant that just to break even we’d need to sell tickets for more than €1000.

Nathan Barry presenting at DYFConf EU

While we didn’t sell as many tickets as we expected (we sold 62 and budgeted for 90) what resulted was an intimate and extremely valuable few days with some extraordinary people.

We’re doing it again this June at the same venue, and it looks like upwards of 90% of attendees will be returning 🙂

We also hosted another conference in Norfolk, Virginia that went really well. We’re thinking that next year we’ll want to match Europe and find an all-inclusive spa we can book out in the US.

For the last 3 conferences, we’ve either barely broken even or lost money. Conferences definitely aren’t making us a profit, but they’re great for building the DYF community and getting like-minded freelancers and agency owners in the same room together.

Launched our Global Meetups Initiative

At the beginning of 2016, we sent out a survey to the list to see if anyone would be interested in helping us kick off the creation of local groups of DYFers that would meet at least monthly.

Since then, we’ve organized over 200+ groups from around the world.


Our goal with the directory isn’t to make any money, though we have brought on sponsors (thanks GoDaddy!) to help cover our costs in managing this directory.

But we hope that by giving people access to other business-minded freelancers in their community we’ll do our part in helping create mastermind groups, business partnerships, and lifelong friendships.

We’re slowly going through and meeting with each group to figure out who’s in charge, when they’re meeting, and more. Over the next few weeks, we’ll be pushing out more group management features, like being able to see a list of past and future events. Additionally, we’ll be highlighting select events and sharing photos and attendee takeaways here on DYF.

If you haven’t yet joined your local group, what are you waiting for?

Broke ground on Freelance Without Failing

I finally broke ground on the book I started thinking about last year.

A few weeks ago, I took a few days off to hole up in a hotel room and get to work planning and outlining this book. It’s focused on helping those who aren’t yet freelancing safely make the jump to full-time freelancing.

Much of the content on DYF is focused on helping people grow the business they already have. My goal with this book is to help those who aren’t yet freelancing determine if it’s right for them. This means giving an honest overview of the pros and cons of freelancing, and what changes need to happen prior to quitting your job and starting your own business.

I’m aiming to write for about an hour a day, and sometime in January or February I should have a draft ready for editing.

The book will be available in print and on Amazon. Like with most books, I don’t expect to make much money off the book, but I do think it will contribute significantly to the growth of DYF.

So that’s what we’ve been up to in 2016…

In the first week of 2017 I’ll be sharing with you what we’re planning for next year.

Here’s a little teaser… 🙂

  • A complete redesign of the site.
  • Tailoring the copy, testimonials, case studies, imagery, call-to-actions, and product listings based off of what you’ve consumed (like the type of articles you’ve read), what you’ve told us (through the passive surveying we do), and what you’ve bought or joined.
  • The most badass courseware you’ve ever seen. We’re taking our obsession with personalization and will be modifying our courses based on the kind of work you do, where your business is now, and where you want it to be.
  • More courses that make you more valuable to your clients by teaching you skills like marketing automation.
  • Bringing on our first full-time hire. (Everyone who helps me now is an independent contractor.)
  • Ramping up our paid acquisition budget. Right now we’re just spending $60 a day, but because we track literally everything we know exactly what we can spend to generate leads. Time to scale up!

Thanks so much for being a part of this adventure.

And I speak for myself and the rest of the DYF team in saying that we can’t wait to help your business continue to grow in 2017!