5 Secrets to Business Success from Drip Master Brennan Dunn

If you’re familiar with Drip, you’re more than likely also familiar with Brennan Dunn.

Not only was Brennan one of the very first Drip users, but he’s also a well-known serial entrepreneur who’s started and sold companies, and has deeply embedded Drip’s marketing automation capabilities into his businesses.

He’s even created comprehensive documentation of the entire marketing automation stack he’s built in Drip for his main business, Double Your Freelancing. And he’s giving it away for free.

If you’re not yet convinced of Brennan Dunn’s brilliance as a business owner, marketer, and Drip user, then forge ahead. Recently, I was given the opportunity to sit down with Brennan and ask him about all three of those hats he wears on a regular basis. I was nothing short of blown away by the gems he dropped throughout our conversation.

Here are five of the most valuable takeaways from the hour I spent with Brennan. Spoiler alert: My bonus sixth takeaway is to find (and buy) the shirt he wore. You’ll see it in the videos below; it’s fantastic.

OK, here we go. Wisdom of Brennan, take us away!

1. The Importance of Recurring Revenue

As someone who started a variety of successful businesses, and sold at least one successful one, I asked Brennan what advice he’d give to a younger version of himself, knowing what he knows now. And I was indeed surprised by his answer.

“The mistake I made is, I rushed into building an agency. It sounded great on paper, just like: ‘Oh, if I had ten people and I paid them all 50 bucks an hour, and I billed them at 100 an hour, I’ll be set.’ But I didn’t really know the nuances of running a business.”

Brennan told me that he wouldn’t start the company he first started. Or maybe better said: If he did start it again, he’d do it differently. One of Brennan’s first companies was an agency, and during our conversation he referred to it as both high-touch and high-overhead.

Makes sense, doesn’t it? New client, new project, new contract, every time. No repeatable income that you can steadily count on month after month.

After outlining the difficulties of starting an agency without any recurring revenue, Brennan told me that he’d tell his younger self to go get 10 or so clients to pay him $1,000 a month on retainer for a set of repeatable tasks he was skilled at.

This, he said, would allow him the freedom to take a deep breath and build an income stream he could truly count on without constantly chasing the next client.

 

2. How Much Time a Marketer Actually Spends Marketing

As someone who wears many hats (did I mention Brennan is a developer, too?), I was curious to know how much time Brennan actually spends on the marketing itself. He’s a busy person—with products, clients, events, and speaking opportunities—and I wondered just how much time each week he carves out to market his creations.

While Brennan quoted me the roughly 20 hours a week he spends on marketing, I found a different element of his answer far more interesting. The question he asks himself is:

“What am I doing today that’s permanently increasing the value of this asset?”

This shifts the focus from the actual number of hours Brennan spends on marketing to the value he derives from the hours he does spend. This focus shift is indicative of Brennan’s marketing prowess and is a great lesson for all of us to avoid being distracted by minutia, and spend our time wisely in a way that will passively pay back dividends later on.

 

3. Balancing Your Product and Your Strategy

As you can see, Brennan takes marketing automation pretty seriously; he’s quite literally trying to automate the entirety of his business. In the clip below, he even asks himself this question:

“How is this business an asset that is independent of me and my continual input?”

Since Brennan is juggling the automation of his marketing funnels with the creation of his products and services, I also wanted to ask him how he balances actual product creation and the strategy he uses to sell it. You may be able to see here that a pattern starts to emerge with the way Brennan approaches his business.

Brennan spends the majority of his time strategically engineering his conversion rates at specific points of his funnel, because he knows that every improvement he makes, at any point, will continue to positively affect the rest of his funnel downstream.

“It’s just math. Ultimately, I’m trying to get my business to be a really long math equation that I can go and optimize different points of.”

Sometimes it can be helpful to remember that for your business to succeed, it’s not always about creating a brand new product, a brand new workflow, a brand new website, or a brand new email campaign. Sometimes, it’s about testing and making small optimizations to your existing strategy that can have a 10x impact further down your funnel.

 

4. The Very Best Thing About Drip

At this point it probably goes without saying, but everything Brennan talks about related to his email campaigns—lead capture, tagging, segmentation, and optimization—is being done in Drip. Here on the Drip team, we’re both honored and proud of what an amazing Drip supporter Brennan is, and we’re constantly amazed at the new and effective ways he uses Drip as a product.

Because of his long and involved history with Drip, I was curious to know what he viewed as the very best part of Drip. You’ll see our theme of automation, in the truest sense, continues in Brennan’s answer:

Brennan refers to his primary marketing funnel as “a well-oiled machine.” And if you checked out the documentation of his marketing automation stack that I mentioned at the beginning of this blog post, you’ll know that is a more-than-accurate descriptor of what he’s created. Regarding that well-oiled machine, he also said this:

“It’s taken me a long time to build, but Drip has allowed me to make it so I don’t need to be there on that business hamster wheel.”

What better feeling is there in the world than being able to automate your business in such a way that you can step off of the hamster wheel?

 

5. The Secret to Brennan Dunn’s Most Successful Drip Marketing Funnel

Brennan says his most successful funnel isn’t just an email campaign. The secret is to think of your primary marketing funnel and Drip workflow as an actual asset that you improve on and test over time.

If you think about marketing automation as the bridge between a prospect’s introduction to your business and them becoming a customer, you start to see the journey that your funnel needs to take on.

Ask yourself: Right now, is your primary marketing funnel fully bridging the gap between someone learning about you for the first time and them becoming a customer of yours?


Brennan breaks down his funnel from Double Your Freelancing into three pieces. First, he offers his free email course. Then, he provides recommendations and next steps. And finally, he offers his contacts a paid course that extends their learning.

“It’s been the single best thing I’ve done. It works every day. Every Monday through Thursday, there’s a sale happening. I can be off the grid, and it just does it. It’s really liberating.”

 

Some Final Thoughts

It was an honor getting to sit down with Brennan Dunn for an hour and ask him about how he got where he is today. Not only is he a great and kind person, his effort and his story are truly inspiring.

His persistent efforts to improve his marketing and his business continue to pay off dividends. It shows in the way he talks about what he does and continues to do. You can see how happy he is to have truly automated something that works—something that works extremely well.

Brennan’s presence of mind is maybe the most inspiring part of his business acumen. He’s able to switch quickly between executing on the granular pieces of a marketing funnel, like writing copy, adding tags, segmenting, and more, then change gears to looking at his business from the highest level. He moves from tactical to strategic seamlessly, and it’s something we could all improve at.

These secret pieces of wisdom from Brennan are secrets no longer. So, take them, run with them, and implement them in both your mindset and in your work.

Let us know which tip from Brennan resonated with you most and why in the comments below!

  • Rohit kumar

    Hey Ryan,

    Firstly, I would thank you for the beautiful quotes and especially video clips. While reading this article I was able to spot some of my unnecessary activities.

    I’m inn, downloading Getting started course. 🙂

  • Great interview and getting off the hamster wheel was a statement that truly resonated with me. I have been chasing revenue instead of creating automated processes.

  • Revved up after reading this. Although I’m not dealing with large corporate clients – hmmm, maybe I should be… – getting dependable revenue monthly would be a dream, and that’s what resonated for me.

    My particular challenge is selling high-end, relatively high-priced artwork – my artwork – online. My works sells beautifully when in a gallery, but I have yet to crack the code of online sales. My instinct is that it will be a combo of online and offline strategies and steps. But which ones and in which order? I’ll definitely download the course.