Brennan Dunn's Quest to Sell SaaS Without an Audience

Hello! What's your background, and what are you working on?

Hey! I'm Brennan Dunn. I'm the founder of Double Your Freelancing, and I live in Norfolk, Virginia.

Back in 2008 I started a web development agency, and a few years later I decided to "escape" consulting by getting into SaaS. In late 2011, I launched Planscope, a project management tool for freelancers and agencies. And, like many online businesses, I decided to start blogging about all things freelancing, hoping that it would bring me more Planscope customers.

It worked. But it worked a little too well. My weekly articles soon turned into a book, which later turned into a course, a podcast, another few courses, a North American and European conference, and over 40,000+ active members of the Double Your Freelancing community.

In early 2016 I sold Planscope so I could focus full-time on Double Your Freelancing, which is averaging about $78,000 a month in sales this year.


What motivated you to get started with Double Your Freelancing?

Selling a project management SaaS is hard. Really hard.

Building it was the easy part. After all, my agency built web apps professionally for our clients.

But actually getting people to find the product and try it… that proved to be challenging.

So I started writing about my own experience growing an agency. I shared what I had learned about getting clients, pricing our services, and even growing a team. My assumption was that there were a lot of people asking Google for answers to "what do I charge my clients?", and relatively few asking Google for project management software recommendations.

It's really hard to single-handedly support and grow a SaaS, especially when you have no audience.


Over time, I started to get a pretty decent uptick in organic traffic and shares to the content I was producing on the Planscope blog, but it wasn't translating into Planscope customers (and revenue) at the level I needed it to.

Thanks to the encouragement of Amy Hoy, I decided to ignore all the self-doubt that kept me from making any money off the content I was producing for free. I decided to self-publish a book on pricing.

This book was called Double Your Freelancing Rate, and it was a framework that emerged out of a lot of what I learned while running my agency. The title was a bit linkbaity, but it worked.

And, surprisingly, customers loved it.

Out of the need to pay the bills while scaling up the "long, slow SaaS ramp of death", I started to heavily invest in producing paid educational content. The book led to people asking for tips on getting clients, and that led to another workshop. Then people started asking about how to grow an agency, and that turned into a two-day online workshop.

Then came a weekly podcast, followed by meetups we helped organize around the world. In 2015, I hosted my first conference here in Virginia, and then another in Europe.

International Meetups

It was around this time that I realized that my business was all over the place:

I took a big gamble and registered and yanked all the non-product related content off the Planscope blog and moved it to this new site, along with my podcast and all my products.

How have you attracted users and grown Double Your Freelancing?

Right now we're at just over 41,000 subscribers, and we're growing at a rate of about 2,000 net-new subscribers a month.

Most of the growth has come organically. I put a lot of time into writing long-form content primarily optimized for human consumption, and this has led to Google sending me a little over 1,000 visitors a day (and climbing) over the last year or so.

Starting out I did a lot of things that don't scale. I jumped into Quora, HN, and other discussions about freelancing. I wouldn't spam, but I'd find ways of weaving in content from my site into the discussion and providing a backlink.

After I started to get some decent organic traffic, I focused on researching keyword gaps: What were people asking Google that I didn't have an answer for yet?

This has led to a number of 5,000+ word guides that consistently drive upwards of 100 visitors a day each from Google.

Besides organic, I also spent a lot of time finding people with similar audiences — many of whom were friends I'd met at conferences — and asking if they wanted to host a joint-venture webinar with me. This was an easy sell since I came to the table with a document detailing historical webinar stats of mine: average revenue per registration, per live attendee, and per sale, along with a complete breakdown of what I would cover and how I wouldn't hard-sell their audience.

In the span of summer 2015, I added about 10,000 people to my list and did over $150,000 in revenue just by making the rounds with a single webinar.

I think the best thing I did was that I never focused on the product itself. I tried to meet someone (in this case, freelancers) exactly where they were right now. Were they complaining about clients, even though they actually had a client communication problem? That was fine. Over time I'd prepare them to become my ideal customer… but at first, I just wanted to come to them on their level, wherever they were currently struggling.

How did you balance running a SaaS while running Double Your Freelancing?

Not well.

Planscope didn't ever take off the way I wanted it to. And I have theories as to why that was: I never took it as seriously as I should, it required customers to completely change the way they worked, and growing a business at $24/mo is hard.

But my inability to support and grow the product hurt the customers, so I turned to my friend Thomas, founder of FE International, to help me sell the company.

It was hard. If it wasn't for Planscope, there'd be no Double Your Freelancing. But I realized my own limitations, and I came to terms with the fact that I was pretty lousy at running two companies full-time.

What's your business model, and how have you grown your revenue?

My business model has evolved over time.

Most sales are one-off courses. The average transaction size is around $200-1,000, and the product is delivered in full immediately upon purchase.

Over the years, I dabbled in a few types of subscription products and more premium products. Recently, I retired a $9,000, super high-touch, 7-month long program. It required a more personal form of sales that we didn't have the manpower to handle, and the profit margins weren't that great (under 5%). I've also sold conference tickets, membership access, and other products in the past.

In the end, for the kind of business that I've designed and the sort of customers it attracts, a flat-priced transactional model has consistently won out as not only the easiest to make money with, but the most profitable.

When I started, I used to use outsourced ecommerce platforms (like Gumroad and SendOwl), but over time I wanted to consolidate everything into a single platform that I had total control over. These days, I'm using WooCommerce.

We're now moving away from the big launch model of sales. Instead of doing a quarterly list-wide launch for one of our products, we're moving toward more lifecycle and behavioral pitching. The goal here is to normalize cashflow, as some months can bring in $150k in revenue, but others bring in barely $50k. Not only do we plan on normalizing cashflow, but we're hoping more behavioral and targeted launches will double average monthly sales.

To do this, we've put in place a completely automated system for acquiring, nurturing, and ultimately pitching subscribers. Rather than a one-size-fits-all approach to both email and on-site messaging, we've put a lot of focus on super personalized content that positions our content (free and paid) against the exact needs our subscribers have.

Sales for Double Your Freelancing

On average, we're doing around $78k in monthly revenue with around $10-15k in business overhead (paid to contractors and software services — no other full-time employees.)

What are your goals for the future?

Double Your Freelancing is poised to continue to grow.

Because we've really honed in our automation and the way we get people who join our list to ultimately become customers, this lets us focus most of our time on:

  • Increasing leads by capturing more questions from Google we don't yet have answers to
  • Improving the products (and R&D'ing new ones)

I plan on keeping the team as lean as possible. Since we track literally everything (channel, funnel, and demographic valuations) it's easy for us to see what parts of our funnel are leaky and to quickly patch them up.

The single best thing I've done for the company is to take myself off the hamster wheel of churning out the right amount of content to nurture your audience, and then churning out a launch sequence to get them to buy. The amount of automation we've put in place has allowed us to maintain consistent (and growing) cashflow, minimize overhead, and really systematize and test what we're doing.

Like many online businesses, I decided to start blogging… It worked. But it worked a little too well.


I've started a new company, RightMessage, which is built on the underlying code I wrote to hyper-personalize Double Your Freelancing. While Double Your Freelancing continues to largely run itself thanks to automation and a few awesome people who help, I'll be able to avoid the crisis I had in 2015 when trying to simultaneously run a SaaS and an training business.

If you had to start over, what would you do differently?

If I could start again I would have not started with a SaaS.

The developer in me wanted to start with software because software is what I knew best. But it's really hard to single-handedly support and grow a SaaS, especially when you have no audience.

R&D'ing training products is much easier. Done well, it provides the same level of value per dollar as software. It also allowed me to engage in a different way with my audience and my customers (e.g. I never really thought, as a vendor of project management software, that part of my customers' success was because of me. With Double Your Freelancing, customers write in all the time to tell me just that.)

With Double Your Freelancing, I wouldn't have tried to take a shotgun to audience growth. I probably wouldn't have done a podcast or the short-lived daily video show, which lasted about a week.

I would have focused on doing a few things that work really well for me — and I'd have stuck with them.

Have you found anything particularly helpful or advantageous?

I credit a handful of people for helping me get down the path of building and selling products:

  • Amy Hoy and Alex Hillman for their course, 30x500. This started it all for me.
  • Patrick McKenzie for being so open about growing his businesses and being a "developer's developer".
  • Rob Walling and Mike Taber for hosting MicroConf, which has opened up countless doors for me, and Startups For The Rest Of Us

Recently, I've really enjoyed Chet Holme's The Ultimate Sales Machine and wish I would have read it years ago.

Writing often has helped, especially since being able to crank out a sales page or article can be done in just an hour or two. This has made it really easy to test new product ideas and create the kind of content that serves as the primary growth engine for my business.

What's your advice for indie hackers who are just starting out?

There is a lot of information out there presuming to tell you exactly what you need to do to start and grow any kind of business.

This information can be, and often is, good and useful. But the best advice I can give you is to not get too caught up in it all.

If you decide to sell to businesses, know that they will buy from you if you can make them more money or help them spend less. Look for a problem you can solve that accomplishes one of those two things (or, ideally, both!).

Maybe you've solved this problem for an employer or a client. Maybe you know enough business types that you can talk to in order to learn as much as you can about whatever specific business problems are holding them back, and discover ways that you're able to help them find a solution.

Once you've figured out an expensive business problem that you're capable of solving, your job becomes helping them get from the problem to the solution — that's it.

How you do that, whether it be software, an ebook, or an in-person workshop, is probably pretty immaterial. Just help them get from A to B.

Jobs To Be Done is a great framework for how to question people in the right way that sheds some light on why someone buys (or doesn't buy). But that often presumes the existence of a product (or a way of bridging the gap from problem to solution). By stepping back and doing a lot of listening, a lot of analyzing, and a lot of testing, you'll be able to come up with ways of getting people from the problem they're experiencing to the solution they care about.

…And that's the surest, safest way to figure out what to build and why it needs to be built, which is a prerequisite for any marketing or growth strategy you'll ever come across.

Where can we go to learn more?

If you have any questions for me about building Double Your Freelancing, consulting, personalization, or automation, I'll be hanging out in the comments below!

Brennan Dunn , Creator of Double Your Freelancing

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