a pod-chat with…

a pod-chat with…

Brennan Dunn

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Hear how Brennan moved on from trying to build his SaaS and ended up helping thousands of freelancers to build better businesses.

Lifetime Value is a one-day, single track conference for only 160 people who don’t want to spend their working lives trading time for money. We’re hosting it on the 19th of April in Brighton in the UK.

For tickets to the conference or even one of Brennan’s workshops and more details go to ltvconf.com.

Show notes

Brennan’s Twitter

Double Your Freelancing
Brennan’s courses, academy and online home.

The Blueprint: Sell Yourself Online
Marketing your brand online

Double Your Freelancing Rate
Make the transition from Hired-Gun Freelancer to Highly-Valued Consultant in less than 30 days

Mastering Project Roadmaps
Increase your conversion rates, make your time more valuable, and set yourself up as a premium consultant

Master Drip Email Marketing utomation
Go beyond the basics and become a marketing automation ninja

Double Your Freelancing Academy
Give us 7 months and we’ll give you a $100,000+/year freelancing business

Brennan’s SaaS, sold to focus on DYF.

Life. Time. Value. Videos from 2016
Brennan attended last year

A bootstrapper conference in the US & Europe

Email marketing software

Brennan’s tool of choice for automated email marketing


Andy [00:28]

Hello and welcome to the lifetime value podcast. I’m Andy Croll. In this show we’ll be meeting one of our 2017 speakers Brennan Dunn. Brennan’s a consultant-cum-educator helping freelancers all over the world to have better businesses through better sales. Hello, Brennan.

So, I’ve been aware of your work for probably the last 3 or 4 years. I checked my receipt for Double Your Freelancing Rate and it was 2014. But rather than me say what I think you’re about why don’t you describe yourself and what you do day to day.


Nowadays I’m running Doubleyourfreelancing.com where we’re helping people who are creative or technical but are pretty limited on the business side of things and are running successful and profitable businesses so my average customer or subscriber is someone who quit their day job, are working for themselves and they’re technically juggling a few clients but when it comes to how to market themselves, how to price, how to pitch they still have a lot of unknowns and then they come to me and I do my best to help.

Andy [1:32]

So how did you get into that world? Obviously I know you ran an agency at one point, but let’s go all the way back to leaving school and having no idea.


I left my liberal arts school to start a start-up because I thought it would be fun. It was unfortunately tied to the housing industry which, when it crashed in 2006, 2007 the business kind of collapsed on itself. I didn’t really know what I was doing but I thought it would be fun. So I ended up getting a job pretty quickly at an agency and learnt about the basics as much as I could in the technology department about a larger agency and how agencies work.

What ended up happening though is that I moved up to Virginia from Florida. I became a full-time freelancer kind of out of necessity. I didn’t really know any businesses locally. And I started freelancing and I did fairly well and I got to the point where I could either turn away work or grow a team. So I grew a team, got it to 11 employees and got sick of building apps for other people so I wanted to build my own.

I started my software company which was my third company at the time, and it was Planscope, a project management app for freelancers and agencies. Basically a tool that I wished I would have had when running my own agency. The conventional wisdom for marketing a SaaS is to do content marketing so I started writing about freelancing-related topics. Before I knew it I had a book out and a lot of other material. And then that material ballooned into a seven figure a year business and I wasn’t able to give Planscope any attention so early in 2016 I ended up selling Planscope through our mutual friend Tom Scale and that’s where I am now. I’m now full time on Double Your Freelancing.

Andy [3:33 ]

So you say you joined an agency, was it a big agency, was it a very process-driven agency or was it a smaller gig?


It was a 30 person agency that did work for big brands like different Airlines and resort chains. The work wasn’t anything outstanding but the owners were very good at wining and dining so they ended up having a great portfolio of clients who loved spending their budget on the fun agency.

But to me it was pretty eye opening. It was my first actual career job, I guess you could say, as my first out of school was running my own company with a friend of mine. It was eye- opening but what was nice was I started as a developer on a team but within a few months I was leading the department and I got to go and hang out with the owners on business trips and got to kind of see a bit about their world instead of being just a low level developer.

Andy [4:36]

Your start-up was obviously in the real estate world which is obviously all about sales, so was this agency your first exposure to that kind of salesy world or was that part of your original start-up as well.


So here’s what we did with the start-up that failed it was called Aganon Solutions. When I was in college I had done some side work for a mortgage broker and he wanted me to just do a simple edit, and I didn’t know anything about how to write copy. But he wanted me to just a code in a simple thing that he could run ads on AdWords back when it was affordable for this kind of stuff.

Plenty of people went to that page, people would opt in, and then he wanted to do it I wouldn’t do a revenue share with me. So instead of paying me I was naive enough to say “Sure, yeah I’ll just do a 50/50 rev share”. The average commission that they would get would be about $4-5000 per loan that they sold, I guess.

I made pretty good money in college doing this and what I ended up doing was when I got to thinking “Screw college, I’m going to do my own thing and really scale this because this is awesome” I thought “Well, what if we ran nationwide ads and what if these Nationwide ads could all funnel people into effectively an app but a landing page. And then I would just geolocate people when they hit the site. Because in the U.S., mortgage brokers can only work in certain states. So they have accreditation in one state for another. The person clicking on the ad happened to be in Florida we would have a pool of Floridian mortgage brokers and we would just route them through that pool. And then we would brand the page and put their picture and the company logo and copy about them and stuff. But everything else would be a standard template.

So the idea was- the traditional way of getting leads was to buy leads through a lending tree which generates one lead and sells it to 50 people. And the problem is mortgage brokers all sell the exact same thing. So if you’re not one of the first few people you’re not going to get the project or the client. Our thing was that you could get branded leads that already know about you and they come to you in real time versus buying a lead that opted in 3 days ago and that 30 people already talked to. That really resonated with people. But the economy didn’t really sustain it at the time.

Andy [7:05]

It’s interesting that this sales funnel thing appears to be a feature of your career. Has that been a deliberate thing or just a happy accident?


Yeah, my Dad owned a company when I was growing up. He didn’t own a timeshare company but he helped people who were conned into buying timeshares. He helped them re-sell them and get them off their plate. So he did a lot of direct mail, he got me reading up on the direct mail legalese. He got me into that and at the time I went to school for the classics, so I’m a little bit of a “Oh that’s cute sales post arts”.

It left it’s mark on me, definitely, when I went on my own entrepreneurship path. But if the stuff I knew nowadays about re-marketing, not that that was a thing back then, but optimising opt-in pages and forms and so on it would have been a much different business.

Andy [8:11]

You say you freelanced and you were getting too much work so did you immediately hire someone, did you go to a team of contractors you were friendly with? How did you structure that and get to 11 people?


I knew people I met at conferences and stuff who were freelancers. And I was getting a lot of work and I basically ended up contacting them all saying “Hey what if I I’ve got some projects…” At first it was all very - I’ve got a project. I can’t do it all myself, I need help with it. So it was a subcontracting arrangement at first. Got that up to 8 people. Unfortunately all 8 of us were on one project that ended up running out of money overnight. Or most of their funding overnight. Their investors weren’t willing to keep dumping money into a sinking ship and unfortunately at that time I didn’t really have the gall to push back and say  - this is a really flawed business model. Why are you having us build it?

But at the time I just thought, whatever I was hired to do, I’d do. So I did that. I had 8 remote sub-contractors. Then virtually overnight the rug was pulled from under us, and it was back to just me. But I had money in the bank at that time and I thought I want to do this properly. I’m going to open up an office even though I have no employees. I’m going to open up an office and I’m going to sit there in an open giant room on my own.

And then I went and found somebody who could basically do sales. I didn’t know a lot about sales at the time and I was introvert so I didn’t want to deal with talking to people, I just wanted to code. So I hired a salesperson and then it started to work. I would come in and kind of be the closer in a way because I would actually tell them how here’s how we can help you. But he would go to networking events and kind of get them in the door.


He would open the funnel up.


Exactly yeah. So we started to scale. I made the mistake of hiring around projects once again. But it worked out well because it started to really build an audience locally. I wouldn’t call it an audience, just our MailChimp had a few thousand people in it that were local. And we started doing events, we started doing seminars, we started doing some basic automation. And it got us to 11 employees, we had about 2 million a year in revenue and we were doing well. I had created a new 9 to 5 for myself which I was really happy with. Didn’t really pitch much stock into company culture, because I just thought, just hire smart people and the rest will just fall into place. It didn’t work that easily.  But I just wanted to get out. Because I had a six figure a month payroll overhead.

Andy [11:09]

That’s the thing about that size of agency. It’s the awkward size. You’ve got to keep feeding the monster once you’re beyond 3 or 4 people.


It sounds like, whenever I say 2 million a year. No, I didn’t do 2 million a year. I made less than 100k a year. But the company brought that much in. So we had high overhead and I wanted the opposite of that. I wanted a lot of people paying a little bit of money with virtually no overhead.  And that’s when I started the Planscope.

Andy [11:40]

You do get this story from lots of people, which is - I built this thing that I thought people wanted and it turned out the world dragged other stuff out of you. So you said earlier, the content marketing that you were trying to do for Planscope has eventually turned into the business that you’re running now. So how was Planscope as an experience?


I had experience building SaaS things before for clients but running one was a different beast because I got to be more focused and I really had to focus on onboarding and lifecycle emails and kind of the usual stuff that I guess small solo SaaS owners have to deal with. But early on it was like pulling teeth trying to get people to pay 20 bucks a month for an app. But I started to get a better understanding of what people wanted, I started to tweak the sales stage and it was really the first time I had ever gotten to that critical point which is, I’m doing my thing and then somebody I’ve never met brings me money over strength. Even though I had an agency and we did well all revenue was a result of annually invoicing and networked revenue coming in.

Andy:You felt like you really earned those? [13:03]


I think for any entrepreneur the biggest mind shift is the first unsolicited payment. That was to me a really big eye opener and it was really exciting but it was still hard because I didn’t have enough money coming in from the app to build a team or anything. Not that I wanted to at that point. I didn’t want to go down that team building route again.

But it was fun I got to do the coding of it, I got to do design on it. I got to do all the marketing myself. And I started to build a proper email list, I signed up for infusionsoft, all that sort of stuff. So I got my feet wet doing all that.

And up until about two years ago there was no Double Your Freelancing. I had all these courses and products but it would always be either on a single page domain or my podcast was on brennandunn.com and doubleyourfreelancingrate.com. I had all my articles on the Planscope blog. So it would be so schizophrenic in a way where people would be pushed over to the Planscope blog and they would be like “I bought Double Your Freelancing Rate. I don’t even know what Planscope is, why am I here?” But finally I detached the two and that was probably for the best.

Andy [14:28]

That is something that I have suffered from myself; I run a Ruby conference in Brighton and there were friends of mine who knew that I ran a Ruby conference who didn’t know that I was running LTV the same week last year. So, yay marketing 101 for Andy!

Talking of LTV you attended last year .


I did.

Andy [14:55]

How did you hear about it last year? I remember seeing your name pop up and going Oh wait a minute. Brennan’s coming. That’s interesting.


I think I saw it on twitter or something. It was actually after the conference I ran in Sweden and I was hanging out in Europe for a few weeks. Honestly if I was still in the U.S. I probably wouldn’t  have jumped the pond for it, but I was like, Oh I’m in Germany. That’s not far. I know every European thinks it’s far but for an American that’s like me going to Georgia. So I’m glad I went.

Andy [15:30]

As somebody who - this is about 8 months ago I guess – you’re already on top of your freelancing, you’re already selling the course, the e-books, your conferences - what did you get out of it as an experience?


When I go to conferences, I’m looking for two things: first off the bigger thing for me is ultimately the connections I make and the people I meet. And I usually stick to U.S. conferences so it was really nice. I knew people like Rachel Andrew and others who I had met in other ways before. But the bigger thing I think was just getting to meet people who I didn’t yet know who they were online. Because there are cultural differences between the U.K and the U.S. for example.


So they say.


I remember hearing a talk on sales at Microconf Europe and I had heard the same talk at Microconf Vegas and the reaction was totally different.


That’s interesting.


So it was really great from a few perspectives for me. First was the new audience, because the U.S. conference I go to, it’s the same probably in Europe. We all go to Vegas, we all go to Microconf, we all sometimes go to Business of Software. And this was a new group for me, which was great. And that was huge.

But the other thing was, a lot of the talks. For example I’m good friends with Alex and but I don’t think I had ever heard him talk before so it was great getting to hear from him along with people like Rachel and a lot of the others. Patrick is always awesome. He and I are friends so they weren’t any eye openers from him, but I know for others who hadn’t heard Patrick speak before they got a ton out of that.

It was my first time in Brighton. Even though I don’t consider that the beach because it has rocks


I like to think of it as big sand, if that helps.


I’m from Miami so my idea of a beach is different.


That’s fair.


But it was great, the weather was wonderful and it was a really cool time. I think at that point the only other place I had been to in the UK was London which is quite a bit different

Andy [18:09]

Yes absolutely. Cool. So this year you are speaking but also you’re doing some workshops for us. We’re selling these direct so if you want to go onto the workshops you have to drop John an email from the website. But broadly speaking we are running two tracks. We haven’t really got good names for them yet.

One is aimed more at people who are taking their first steps on a product journey I suppose. The second track is more for people with established something, and they want to take the next step. You’ll be teaching on both of those tracks but mostly on marketing automation which is something I know you’ve been pushing hard on over the last few months. So can you give me an idea of the stuff that you’re going to cover?


The more advanced track is going to be more focused on personalisation which I think is going to be the evolution of automation. It’s one thing to say “I’m going to drip out emails on a time limit. It’s another thing to say I’m going to have these emails tailored based on who they are.

I saw a stat the other day from a company called Monotape saying that 94% of companies want to automate personally but only 40% do. So the consultant in me thinks: Opportunity! Whereas the business owner in me is thinking I’m glad I’ve seen this now because I’ve seen first-hand what effect it had.

So for people with more established businesses it’s going to be more focused on helping them really maximise what they’re doing when it comes to segmentation, personalising their both their website and for example the marketing emails being sent out. We all know how powerful niching is. For most people niching is having to do with the product instead of the way that you present the product. So I look at it as niching on the fly.

So that will be one of the more advanced tracks. More beginners will be one of two things: I want to give people actionable steps in terms of getting started in automation but the other thing is to kind of give people an idea of what’s possible that they might not know is doable with automation.

Andy [20:36]

Absolutely. The aim of the “beginners track” is that people will leave there with something to sell. So they will leave with at least a strong idea of what products they could create/ Amy Hoy is also going to lead that track as well. And they will leave hopefully with a landing page and a few automated emails ready to go. Or at least a good solid plan of being close to shipping, which I think is super powerful.



Andy [21:09]

You talked about running it solo: everything from making the tea to doing the coding and the marketing. How long did you go at that as your main thing before you decided to sell?


It started out in 2011. While running the agency. And then I sold in 2016 so it was  5 years later from first commit to sale.

It was pretty much linear there was none of this hockey stick anything. It stagnated actually for quite a while when I got distracted by all the DYF shiny objects and money that were being thrown my way. I just kind of let it go into maintenance mode for the last year and a half. No changes. Which I felt really bad about but I just didn’t have the energy to run two businesses.

I ended up realising the better thing to do would be to just sell it to somebody who could just focus on it full time. So we found somebody who wasn’t a portfolio company acquirer but instead an individual who had money in the bank, they wanted to run their own SaaS but they didn’t want to go through all the risk of starting out with a new idea and building something from scratch and everything else.


And a base level of customers as well, of course.


Exactly and profit and revenue at that point so that was good for them.

Andy [22:43]

So there seems to be a big change during that period you were talking about in Planscope where you were focused on the Double Your Freelancing stuff. There’s a focus on sharing the stuff that you learned by accident, almost. Making that stuff actionable.

There’s a big educational part in all that, a big drive and you seem to be able to write an enormous amount I’m sort of half expecting an email from you to pop up in my inbox while we’re talking. So there is a big educational component is that something you consciously chose? Or did it sort of happened to you and you found Hey wait a minute I really enjoy this.


Part of it was early on I was building this Planscope thing, right? There were two tracks of content that I was producing. The first was the traditional content marketing stuff that would appeal to the target audience. The second was stuff that I honestly enjoyed writing about. The meta stuff. For example here’s something that I’m doing about how I changed onboarding. Now I realise that doesn’t appeal directly to the target audience.

That being said if you put together a Venn diagram of people who care about that and people who are consultants it does overlap a bit. It wasn’t the best focus of my time but I really enjoyed doing it. I’d still occasionally consult, maybe a few times a year to keep some skin in the game and it’s good to have somebody who helps consultants to still consult. It helped with that.

It also got me in the door of various conferences and such to speak at and it was just fun to write. Back then it was pretty easy to get the number one on hacker news thing. So I wrote a few things in the hacker news got a lot of traffic and some opt-ins but even though it was a miniscule percentage of overall traffic it was still huge for me. It was a lot of fun writing about. I don’t want to be the guy who creates a course on building courses or anything like that. You see that all over the place.

That being said the most recent thing that I did is kind of about a lot of what I have learnt. It kind of violates that principle I had in the beginning of not getting meta with my own products. But I found a way to take the new course and apply it in a way that says “Hey, if you’re a consultant, or a Freelancer designer, developer whatever, you should learn marketing automation because it will help you charge a lot more. Because that’s what your clients also want on top of the code you write or other designs you create.”

Andy [25:37]

Moving those two Venn diagram circles together


Exactly. It’s just a way to make yourself more premium. I could create a course on what I have learnt about sales copywriting and persuasion writing as well as everything else which again is useful to you as a consultant it’s not just me getting abstract about what I’ve done on my own. There is something more tangible.

Andy [26:02]

Another thing I’ve noticed in your recent work is you’re beginning to broaden your audience or at least broaden the scope of your writing. You talk more about anyone who consults rather than devs. It did seem in the early days that you were a dev speaking to devs and now you seem to have deliberately opened that up to people who are doing things both online and offline.


Yes exactly. Audiences naturally broaden over time. Now the book I’m working on that I’m hoping to publish this summer is going to be focused on helping people who are not yet freelancing but are full-time employees and want to make the jump. The self-limiting doubts and everything associated with starting a new business. So it’s definitely broadening. But that’s where for me personalisation is really effective because when you go to the sales page of any of my products specifically right now Double Your Freelancing, or in a month or two any of my products, depending on what you do the sales page will change.

So if I know you’re a developer the sales page will be very development focussed. Whereas if I know you’re a writer it’s going to be very focused on helping you charge more as a writer. My idea is I can niche on the fly both the courses I have and the content that I have specifically based on what I know about someone.

I collect a lot of data using Crest profiling that allows me to have a very good indication of who somebody is. Which means for example I can make all the testimonials be from people like them. So if you’re a designer and you’re an agency you can get testimonials from other design agencies. I still think you can broaden.

This is not stuff I would recommend for new people. I wouldn’t say “Go broaden and then just personalise”. I would start with personalised or very niche like I started with. You might broaden out over time but you can still accomplish the same thing with an on-the-fly method rather than it being one niche only.

Andy [28:12]

This is the idea with the two tracks of workshop. You’ll be able to show more advanced stuff for if you’ve already got an audience of a few thousand people. It’s much more akin to one of these consulting gigs that you were talking about in that more advanced track.



Andy [28:21]

I was browsing the Double Your Freelancing site today and it occurred to me - sprawling is the wrong word but, there is a lot of content in various forms. You have a very successful email course, the eBook, and you say another book coming. There’s a community. And then you run training courses.


So, Double Your Freelancing Rate, when you said you bought it, it was an ebook then. It’s now redone as a full fledged online course. So I don’t really have any books at the moment except that one that I’m working on. But then we also have 200+ meet-up groups that meet up monthly around the world.  


Yes, I saw that. That’s amazing.


And we have two conferences. We have a lot of moving parts but a very stream-lined, thin organisation because of automation.

Andy [29:15]

Yes that’s exactly where I was going. How many people is Double Your Freelancing? Is it just Brennan?


There’s two full-timers, me and my assistant. The academy, though, takes quite a few people to operate. So there are fourteen people who make that run. But that’s a very big intensive online school. Actually one of the speakers at the conference, Laura Elizabeth is helping me with the redesign of the site too. So it’s a small team, except for the academy, which is practically a separate company at this point.

So in terms of revenue split the Academy is the bulk of your income, is it [30:02] Andy

Not for DYF profit actually. Right now we’re just about barely breaking even with the academy. But that’s more intentional and we’re kind of getting our footing with that product. But it does bring in a lot of revenue. Tuition is $8100. But it’s practically an agency. It’s an online course but everything is taught live and we have 7 teachers and multiple success coaches and a lot of moving parts.  It’s not just like “Here’s a video course you bought. Have at it.”

Andy [30:46]

It really is a school type operation.


That also means that the overhead is tremendous. Most of the revenue is from Double Your Freelancing Rate new drip course, Mastering Project Roadmaps. A lot of the self-study courses that I offer. That’s where most of the profit comes from.


And obviously most of that stuff runs with just tweaks from you. It’s stuff that you’ve already written and re-tweaking rather than having to reproduce courses all the time.


I just re-filmed Mastering Project Roadmaps so we’re going to create a new version of that course as a free update and do another launch of that. But yeah, for the most part you pay, you get the product immediately, the fulfilment is already complete. Whereas with the academy, you pay and we still need to fulfil.  

Andy [31:37]

Your videos: how long do they take? Because they’re very professionally done. You sit in a nice office. Is that your office, or do you borrow someone else’s?


Which videos do you mean?

Andy [31:48]

Probably the first version of the Double Your Freelancing beta that you did. There’s a lot of Brennan talking to camera somewhere nice.


That’s probably the Mastering Project Roadmaps where I actually went out to Los Angeles, and hired a film crew. I actually learn better with more content written courses, and they’re easier to do things like personalising.

One of the things I’m doing this year, which I think is going to be really big both conceptually and also for my customers is making it so that for example if you buy a Double Your Freelancing Rate course, if you’re a designer all the language and examples are going to be focused on you. I already collect the data but if I don’t have the data yet, I want to know what is your goal of the course and what kind of work you do. And then the course will actually modify itself based off that. So that’s kind of the end goal of a lot of the personalisation. Right now I’m doing that in the marketing but eventually it’ll be the whole spectrum.

Andy [33:02]

Always the engineer


Yeah I can’t help it.

Andy [33:07]

Always tinkering with the machine.

So what does your regular day look like? Given that you’re mostly running this empire on your own, what does your day look like?


I’m always tweaking it. Currently I’m trying to start work at 4 am and then wrap up at around noon. I work more when there are fewer distractions. I think I work on English time, maybe. I try to exercise right after I’m done for the day and then spend the rest of the day doing whatever.

But in terms of getting stuff done, I schedule most calls on Tuesday. Occasionally, once, like today, on Wednesday. But most of my calls I try to do back to back on Tuesday. That frees up Monday, most of Wednesday, Thursday and Friday to do more themed days. So let’s say Thursday I’m going to work on this project. And Friday I’m going to work on tweaking all the automation that I’ve got in place. Look at data and make adjustments. That’s what’s worked best for me.

Are there things that you wish you could do more of or less of [34:17] Andy

I wish I could get more stuff done. I always feel like I’m behind. But a curse of running your own business is there’s so many things I could do that they all combined stack up massive in terms of helping growth and everything else.

But it’s really about saying OK, I’ve got 100 hundred things I want to do that all combine into something really big, I’m going to do one this week. Then next week I’ll do number two and so on. One curse of being a developer too and being able to be a jack of all trades with most things is I don’t need to hire anyone to make code adjustments to the frames on my site so I can just do it myself and it’s hard to restrain myself sometimes.

Always tinkering with the machine [35:11] Andy


Do you feel like you’re successful [35:16] Andy

Yeah. It’s cool because when I go to a conference of mine or I go to somebody else’s conference, people come up to me and they’re like “Hey! Been following you forever but you don’t know me yet.” To me that’s successful. But I think that what makes me most successful, beyond revenue and everything else is that I’ve had to basically hire someone to help manage incoming testimonials.

People who are writing whom I’ve never met, they just follow my stuff and they’re like “Hey, this happened as a result of me knowing you, or me knowing your business.” To me it’s like I’m able to do something I could never do as a consultant because consulting you work with typically one or a few clients at once. You can only affect so many lives at once. Here, even with software, even though I would have helped a lot of people with the software, they wouldn’t really attribute the software to any business growth.

I don’t credit Trello with helping me run a better business. It has but I don’t consciously credit it as such.

Whereas when you buy a training course or read a book by somebody you can usually directly credit a lot of what you learned to that. And I think for me, that’s what has made me feel successful. Knowing that all these people that I don’t really know have somehow benefitted from me.

Andy [36:56]

The question I normally follow that up with is, are you happy? But it sounds like that’s a big sort of personal pride for you.


It is. I’m extremely happy with what I’m doing. I wouldn’t want to do anything else. Some days suck, but that’s just life. I’m happy because I’ve got flexibility in time, so I’m able to travel without telling anyone or take a day off unless I’ve got meetings scheduled and then I can just reschedule them.  There’s a lot of flexibility there. And it works. I’m getting to benefit a lot of people in a way I never could do before I became diverse, and just talk to people and see what they’re doing and see how I can help them. It’s like consulting but done on a scale.

Andy [37:55]

Do you have any piece of advice for five years ago Brennan?


Yes. Don’t start a software company without an audience.

Andy [38:08]

That is good advice and I believe that was Patrick’s message from last year’s conference, wasn’t it? He basically walked through the steps from nobody knows who you are to successful software or other business. Were there people that you looked up to when you first started? And are there people who you’ve followed all the way through, or have the people you admire changed?


What’s cool is before I started on this stuff I’d been reading Patrick’s stuff, I’d been following Amy Hoy, all of whom were instrumental in getting to where I am now. And now they’re all really good friends of mine and we stay at each other’s houses.

I used to put them on a pedestal but at the end of the day we’re all just people. So that’s one of the reasons I get Annual Report posts and everything else; reading other people’s stuff is so instrumental to helping me get to where I am now.

I’m happy to talk about it but I don’t include specific revenue on my annual reports any longer because I feel like it doesn’t really help somebody who I’m hoping that it will help, who’s just starting out. I think if you’re starting from nothing and you just sold $10,000 of your first product ever, that’s really helpful because people who want to do that can see it and be like “Oh well if she did it, I can do it too”. Whereas if you’re seeing someone who is doing seven figures with their business, it’s like the gap between me and them is too big, I’m not going to start. So creating in the open and sharing in the open what’s working and what isn’t is so huge for me. And that’s what I’m trying to do now too.

Andy [40:18]

The internet’s bloody good isn’t it? So what’s your ambition and your challenges for Double Your Freelancing? What do you hope is next?


My big thing is I’m trying to not make myself as involved in the business, or needing to be as involved in the business, so a lot of what I do is still just in time. If I send out a newsletter I probably wrote it the day before or the morning of. I would love to have a backlog because I’ve been doing a lot of travelling and been a host at different business retreats.

I just got back from Thailand and I just did one in Colorado a few weeks before that. I went to L.A. to film the new version of the course. A lot of moving around. And the automation keeps kicking in but there isn’t new content being published to the blog or anything like that so I’m hoping to have a backlog of the stuff so it continues on without me needing to be there. So that’s one thing.

The other thing is just going all out on the whole personalisation stuff and really treating my blog like a SaaS. Really saying when you click on an email link of mine it’s a one click sign in where the link you click on identifies you and then the rest of the experience is then personalised. Really just doing a lot more of that. Not going to create new products or if I do, it won’t be a lot. Just really refine what I’ve got. Really streamline the automation that leads people to it. A lot of refinement I think this year for me.

Andy [41:58]

Cool. So at the end of our chats I like to ask if there is anything people have been reading or watching or that they’ve stumbled across that they think would be useful to the Lifetime Value audience. So is there anything that you’ve seen in the last weeks or so that you’d like to share?


In terms of what I’ve been reading actively, like I was saying before we recorded, I‘m going through Homer’s Iliad again so I don’t know how applicable that is for growing a business unless you plan on sacking a city.

Andy [42:31]

Some people do.


Actually if you want to go on that kick, reading Plato’s dialogues, the Republic or any of the better known ones, ae great for learning how to dig into surface level problems and figure out exactly why they really are problems. Getting to the root of it all. That helped me so much with how to solve them and how to set them out. I’ve probably learned more from Plato about sales than any other author.

So that’s one thing but in terms of actual business folks, I keep meaning to read Ryan Holiday’s new book. I think that will be good. I liked “Ego is the Enemy” but I haven’t really honestly gone through it yet as much as I’d like. I’m a bad person to ask about that because everything I’ve been doing has either been fiction or really old books that aren’t business books.

Andy [43:46]

That’s alright. That’s also a good suggestion. Sometimes a good story is just what you need right?


Yeah, read for fun sometimes. Go pick up an airport novel about the president being assassinated or whatever.  

Andy [43: 58]

All that remains is for me to say thank you very much for joining us today and we look forward to seeing you in April for your talk and especially the workshops if you can get onto those. Where should people look for you online?


doubleyourfreelancing.com is my site. You can also find me on Twitter @brennandunn or you can see me in person in Brighton.

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