2015 Year In Review

By Brennan Dunn

2015 has been a wild ride.

Product revenue has doubled. I successfully hosted my first conference. And I pulled off my biggest course launch to date.

Most importantly, the amount of success stories and testimonials that hit my inbox each week has skyrocketed (in fact, I’ve had to hire someone whose only job is to catalog these case studies.)

Double Your Freelancing is working. It’s helped more people than I could ever have imagined truly master the business behind their business.

And we’re just getting started.

Why do I write a (public) annual review?

I’ve looked up to a lot of people over the years.

When I started my agency in 2008, I soaked in as much as I could from other people who were running agencies. At the time, I attended a few technical conferences each year — events like RubyConf, Mountain West Ruby, and so on.

I got to know a lot of agency owners and had the privilege of being able to ask them about the hows and the whats of how they ran their businesses. I met people like Obie Fernandez of Hashrocket, CJ Kilhbom of Elabs, Joe O’Brien and Jim Weirich (requiescat in pace) of Edgecase, Justin Gehtland of Relevance, and more. These hallway discussions led to me learning the business lessons that enabled me to hire 10 full-time employees and bring in millions a year in revenue.

A few years later, I got bit by the “product bug” — thanks largely to blog posts and such from friends I’ll mention in a bit. I knew that I was getting into a world I knew very little about. Sure, I’d built products for plenty of clients over the years, but many of them had fat marketing and PR budgets or, unfortunately, were bad product ideas that were dead long before my team had written any actual code.

It was then that I came across people like Amy Hoy, Patrick McKenzie, and others who had taken the time to blog about their successes and failures.

They made me realize that I could do this, just like I could start and grow a multi-million dollar consulting agency.

There are plenty of things that I knew I had to learn. If I wanted to sell a software-as-a-service, the tried and true offline marketing methods I’ve used for years weren’t going to work. High-touch networking makes plenty of sense when you’re selling a $250k consulting engagement, but not so much when you’re selling a $24/mo product.

But I had to first convince myself that this was possible. By me. Yeah, sure, I wasn’t exactly new to running a business. But doing this would require me to break out of my comfort zone.

I was really good at selling consulting; I knew nothing about selling products to strangers.

But the experiences that people who have gone ahead of me and opened up about what was working and what wasn’t was a huge boost of confidence. And at the time, none of these people knew me (amazingly, they’re all BFFs now.) But their work, their annual reviews, helped give me the confidence I needed. Which led me to Amy Hoy’s 30×500, Planscope, Double Your Freelancing Rate, and then to everything I’m doing now.

No matter if you’re just starting out as a freelancer, are looking to grow a big and awesome agency, or have your sights set on building a product empire of your own, I hope this annual review helps you the same way the reviews of others have helped me.


This year, rather than breaking down everything into an income statement, I’m following the model pioneered by Chris Guillebeau. What went well, what didn’t go so well, and what’s next?

What went well?

Consolidating under the Double Your Freelancing brand has really paid off

If you’ve been following my work for a while now, you might remember back when I had all of my articles living on the Planscope blog, my podcast on, and then my courses living on their own separate domains.

I took a risk and decided to consolidate it all under, but it’s made things so much better.

Now there’s just one place to subscribe and read everything I’m doing. Google’s done their thing, and I’m ranking near the top for a lot of freelancing and consulting related terms, including “freelancing” itself. Organic traffic keeps moving up and to the right. And my entire SEO strategy boils down to: write good content that people like to read, and write it consistently.

This year I’m going to be working on a few things to make the site more navigable, including adding search, better-sectioned content, a few design tweaks (though I really like the simplicity), and more.

I’m selling Planscope

I’m not sure if this should be in what went well or what didn’t go so well, but I’m now in the process of selling Planscope. I’ve been totally blown away by what Nathan Barry has done over the last year with ConvertKit. He took a product that was totally stagnant, dedicated his full-time attention to it, and is now doing over six-figures a month with it.

What I realized was that if I ever want Planscope to be as successful as I know it can be, I’d need to work on it full-time. I’d be a fool to think that a SaaS with all its support, marketing, upkeep, and all can be a passive income stream. And since I’m so focused on growing Double Your Freelancing I just don’t have the energy to take on another full-time job.

I’m working with a broker who is looking for another team to take on this product. Ideally, we’re going to find an agency or someone who is passionate about helping freelancers and agencies to buy. I owe it to Planscope’s customers to hand off the baton to someone who can go all-in on it. But while, and even after, this transition is taking place, we’re still building and supporting the product as we always have.

I’ve put this in the “what went well” section because this is a huge weight off my chest. It’ll be one less thing to worry about. But it straddles the “what didn’t go so well” section because this is bittersweet. It’s my first successful product. It’s what got me started doing everything I’m doing now.

(If you or someone you know might be serious in acquiring Planscope, let me know and I’ll intro you to my broker.)

My biggest course launch yet: Double Your Freelancing Clients

Following the success of Double Your Freelancing Rate (which just crossed 7,000 students!), I’ve wanted to create the ying to DYFRate’s yang for a while. It’s one thing to know how to sell to leads, but all of that’s for nothing if you don’t have any leads to begin with.

During the summer of 2014, I broke ground on Double Your Freelancing Clients (DYFClients) and I launched the first version in March 2015. Because of how much time and effort goes into hosting the class, I decided to only offer it once a year. (It’s a giant consulting / coaching gig for myself backed with curriculum, content, and a team of trusted mentors.)

Like with anything new, I made a few mistakes launching DYFClients:

  • I was a little too Apple-ish about it pre-launch. I didn’t give many details, outside of what it would do for your business. After surveying people who didn’t buy, I realized that they all thought it would cost and be structured a lot like DYFRate. Well, it ended up costing about 5x what DYFRate does and required 6-months of on-going effort. Plenty of those I surveyed wanted to join, but couldn’t budget their time or money for it. When I prepped for the 2016 launch, I hinted at the cost and time requirements months in advance.
  • I screwed up when coming up with the mentoring program. One thing I like to teach people who want to grow an agency is that it’s not as easy as just hiring smart people and throwing them at client problems. Well, one feature of DYFClients was that everyone had a dedicated mentor — somebody who I trusted, knows my philosophy on consulting and what’s covered in the course material, and is good with people. I had hoped that everyone would proactively work with their mentor over the 6-month period of the course by asking the right questions, soliciting help when necessary, and keeping their mentor abreast of what was going on in their business. Some did just this, many didn’t. I learned that access doesn’t mean anything. What’s important is structure, and that was something v1 of the DYFClients mentoring program lacked.

After the class, which opened for registration in February, launched in March, and concluded in August, I knew that for the next round — which I was going to open up for registration at the end of the year and kick off in January of 2016 — I needed to really fix the mentoring thing. So I came up with a more structured and hands-on version of it, sold it entirely over email (something like -> “P.S. I’m kicking off a pilot program for some DYFClients changes I’m doing. I’ll be personally mentoring you. If you’re interested, reply and let’s chat.”)

I booked two cohorts of students and kicked off the Pilot Program of DYFClients in September. It worked… really, really well. In fact, a few of the students are at the point where their biggest struggle is on backlogging and scheduling all the months of work they have available. I let everyone from the first run of the course know that they’d be re-invited, free of charge, to take the class again if they’d like. The ones who didn’t have a great experience with the first mentoring program took me up on that. Truthfully, this ended up costing me tens of thousands of dollars since I pay each mentor per student, regardless of if they’re new to the class or not. But it was the right thing to do.

The 2016 launch of DYFClients, which opened for registration in November, was bigger and better than I could have ever imagined. I also wrote custom courseware to facilitate all the weird nuances that hosting the class required (weekly Office Hours with me, the live Mentoring sessions, etc.) The class kicked off the first week of January (which is why I’m a bit delayed in writing this annual review.) I’ll be sharing more success stories as we get them, but so far the momentum with the new class has been extraordinary.

The conference was AMAZING

In September, I took a huge gamble and hosted my first ever in-person conference. I flew in some incredible speakers and we ended up with a dozen actionable talks that left attendees with mile-long to-do lists. On top of that, it allowed me to finally meet so many people who I’ve known forever online — customers of mine who have been with me since the beginning. I’ll let the video below tell you the rest:

I (finally) called in for reinforcements

After growing a team to $100k/month in payroll overhead, I was dead set on minimizing overhead as much as possible with whatever my next venture was. I didn’t want a lot of meetings, calendar entries, and all the stress that can come with being responsible for other people’s livelihoods.

For way too long, I’ve tried to do all of this myself.

But in 2015, I smartened up and let people who were better than me at certain things help out. Gina’s been helping manage the chaos that is my inbox, and she’s also been writing profiles that focused on students of mine who have been killing it. Katrina’s helped me out by normalizing all the raw data that hits my inbox or survey forms to help me identify trends, overarching sentiments, etc. Kai’s been managing all of the outreach I do and the podcast lineup. And Xander helped make the inaugural Double Your Freelancing Conference a reality.

Hats off to the Double Your Freelancing team.

Health and happiness at home

Things weren’t looking so great last year. We got hit with a huge health ordeal that threw off my business for months, and motivation levels plummeted. (The dark side of working for yourself is that you have few tasks or requirements that you truly need to do. When faced with “do I get up and do what I need to do… or continue sleeping?”, it sometimes sucks to have no real external objection to sleeping.)

But this year, things were fantastic.

  • I spent more time at home, and when I did need to travel I made an effort to bring my wife and kids. (MAJOR points scored here.)
  • We got a lot of small but noteworthy things done around the house, including a bunch of gardening.
  • I bought my dream car, a Tesla Model S. For years, it seemed like all of my money was going to doctors, home improvement companies, or the IRS. It was nice to actually splurge for once (and the car works as both a sports car and family sedan).
  • We started to actually focus on properly saving for retirement.


(Why I do what I do.)

What didn’t go so well?

My daily Q&A show

A few months ago, I started Freelance Answers, which was supposed to be a daily Q&A show that publicly replied to a lot of the questions I receive over email every day.

The biggest impediment to its success was that I do too many things “just-in-time”, which I’ll cover more in a second. I had organized and was sitting on months and months of questions, but the recording of my answers was always done a few days before the episode would go live. And since it was a video show, that meant dragging out all my A/V equipment from my office closet, putting on a dress shirt, and hoping that none of the animals or kids at my house interferes too much.

I’d really like to get this going again. I think it was valuable, and I get so many questions over email that it makes total sense to do it. If and when I kick it back up again, it’ll probably be as just an audio podcast.

I need to get a lot better at queuing things up

In general, I do too many things just-in-time. I’d love to get to the point where I have months and months of articles and guides queued up to be published, along with podcast episodes, guest posts, and so on. This year, I want to be much more intentional with the time I spend on creative things like writing. It’s always easier for me when there’s something tangible and expected on the other end… like a book or video course.

This also means that if I end up getting sick or going out of town, it impacts my newsletter cadence and such. Last month, I was hit with the flu and lost my voice for basically the entire month of December so I ended up publishing no podcast episodes, even though the “meat” of the episodes (the interview) were all recorded in advance. I couldn’t bring myself to recording the intros and outros, which meant none of the episodes I was sitting on were published.

I still have a love / hate relationship with email

Gina’s been absolutely fantastic in helping me sort through my inbox. Twice daily, she catalogs all of my emails into things from customers, things I need to reply to, things that are just more of an FYI, and more. This allows me to cater first to customers, then to things that are time sensitive, and go on from there.

But if I fall out of inbox zero, it’s hard for me to not face my inbox and get overwhelmed. At a minimum, I try to be on top of any customer emails and time-sensitive emails. But if someone writes in telling me about who they are and what they’re hoping I can help them with, they might go weeks, months, or worse waiting for a response. I’ve built my business on openness and not being some untouchable guru or whatever, but often times the input outpaces my output. I’m trying to come up with ways to mitigate this in 2016.

What’s next for me?

I love the process of planning and writing these posts because it helps me really focus in on what I want and need to get done in the year ahead.

Here’s what’s on deck:

A new course titled Mastering Project Roadmaps

A long term student of mine has taken what he learned in DYFRate and ran with it, and now has a business that does over a million dollars a year in paid Roadmapping engagements alone. (What’s Roadmapping? It’s a process I cover in DYFRate that allows you to charge for your estimates and discovery work in a way that substantially increases your lead -> client conversion rates and helps position you as a consultant rather than an order taker.)

His agency has done hundreds of these sessions, which they call Rootstraps, and I wanted to do a joint course with him that covered the ins and outs and selling and hosting Roadmaps.

Last week, I flew out to Los Angeles to record the course and we’re now in the process of getting it edited and finishing up all the supplemental material that we’re including in it. It’s going to end up clocking in at probably around 5 hours of finished instruction, along with hours of raw sales conversations, the document templates they use to sell Roadmaps, turnkey marketing material, and even access to software they’ve written to facilitate Roadmapping.


We’re hoping to ship this in early February.

I want to write a book for new or potential freelancers

Most of my material, and especially all of my paid courses, are focused on helping somebody master some crucial concept of consulting.

What’s missing, though, is something that has more reach. A product that can help somebody who is thinking about quitting their job and becoming a full-time freelancer. A product that’s systematic and covers all the mindset issues that are required prior to jumping head-first into freelancing, the practical steps needed to get yourself up and running, and how to get your first few clients.

The best format for something like this is a book. I’ve started drafting this new book in late 2015 and once it’s done — even though I plan on self-publishing — it’ll be available both digitally and in print on my website, Amazon, and wherever else books are sold.

My first European conference, and another US conference

DYFConf Europe is happening on June 22-24th in Stockholm, Sweden. Some of the same speakers will be back, but I’m also opening up a call-for-speakers (that means you!) It’ll be hosted at the beautiful Yasuragi Japanese Spa and will be all-inclusive — meaning, your conference ticket, food, room, spa access, and more will be one flat price. You just need to get to Stockholm.

More details and registration will be coming shortly once I figure out the ins and outs of VAT and what that means to me, an American company hosting an event in Sweden with attendees coming from both EU and non-EU countries.


I couldn’t be happier with how 2015 has shaped up, and I’m even more excited about what 2016 holds.

A few weeks ago, I surveyed you and asked you to tell me about what kind of guides, podcast interviews, and more you’d like me to focus on this year. I’ve read every submission and have started mapping out this year’s content calendar for

THANK YOU again for being a part of this journey. When I started this business, I wanted to help people learn to avoid the mistakes I made when growing my agency by sharing my own experiences. But more than 4 years later, I now see my job as to help curate, research, and capture the best, most actionable information out there for freelancers and agencies who want to build and sustain a successful consulting business.

Thanks for reading.