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Building relationships with people over time using email

Yesterday it was Brennan Dunn’s birthday. Lucky for us, he took some time out of his day to share some email wisdom with all of us in this interview.

Brennan has always impressed me. He’s a great experimenter with landing pages and email. I think you’ll really enjoy his insights. Hopefully this interview inspires you to try something new this week with your emails.

Show Notes

Full transcript

Colin: Hey, everybody. I am here with Brennan Dunn. Brennan Dunn runs Planscope. He has a very popular blog for freelancers. I’m not doing this justice. Brennan, why don’t you introduce yourself and tell people what you do?

Brennan Dunn: Hey, Colin. My main app is Planscope. That’s my oldest product, and since then, I’ve written two books. I have a newsletter, podcast, a workshop, a new workshop that I’m doing, and just a lot of different things, all related to consulting and freelancing. It’s all very same audience, just different products.

Colin: You do a lot with email, with your newsletters, with a lot of lifecycle emails. How did you get started working with email? What was your introduction to the medium?

Brennan: The first time I really started using email as a way to actually be integral to my marketing was with my first book, so that was “Double Your Freelancing Rate.” I launched that back last August, and it was almost accidental. I did pre-orders.

People paid me, and I felt…I knew that they should be getting something while I wrote the book, so I just started writing once a week as a newsletter, and I would write to them about what I was working on, what I was writing that was going to come into the book that they bought, and I just never stopped after the book came out.

It turned into what was a book-specific newsletter to being my newsletter. I’ve used that now to…really, it’s my glue. It’s the glue between everything I do. It promotes…somebody can enter my newsletter any number of different ways. They can get to it from my blog. They can get to it from a paid ad that runs to a [inaudible 01:59] page. They can buy a book of mine and get on it.

What’s beneficial is, over time, they can come to know who I am, what I do, and my beliefs and consulting. There are the occasional outlets to all the different products I have.

Colin: I’ve been fortunate in that we came across each other really, really early on, so I’ve been lucky to see you grow and to see you just increase the breadth of the things that you can offer people. One of the things that I really like about what you do is the tone. How do you think about the way that you write and the tone that you use when talking to your audience?

Brennan: Any time I send a newsletter, or even any time I send mostly any type of email, I treat it as if I’m writing you directly. If I were to open up Apple Mail, and type in “Colin,” and then start typing, that’s how I treat all of my emails. They’re not designed. They don’t look computer generated.

They look like a peer-to-peer email, which helps, because the tone is very informal. It’s always like, “Hey, Colin, blah blah, blah. Cheers, Brennan,” and that’s literally my format for just about anything I send.

Colin: That’s your template. [laughs]

Brennan: Yeah. I should actually add the salutary and whatever they call the “cheers” part to the email template, but I do write that by hand. It’s very informal. I look at is…A lot of my call-to-actions are actually replies, so I ask people to reply and tell me about something. Truthfully, that’s how I do most of my discovery, how I figure out what language people use, instead of doing these mass surveys.

I run a lot of raw data that I can individually look at and see, “How do people describe their problems? Is there a critical mass of people who have this problem that I could potentially provide something to?”

Colin: I remember we were chatting, I guess about a month or so ago, at BaconBizConf. One of the things that struck me is you said…I think you were talking about the first email in one of your lifecycle series and the question that you ask people. Do you remember what that was?

Brennan: Yeah. It’s actually the second email. The first email is more of an introductory. The second email in my autoresponder sequence is I ask people what the number one problem they have with consulting and freelancing is, and I list out a few different examples. I get a lot of…

I don’t know the exact percentage off hand, but I get probably three or four replies a day that just get tagged automatically in Gmail. I just dig through that every once in a while, but I do make an effort to respond to everyone who writes me. It’s a way to build up a relationship quickly and help people out where I can. That’s the second email I write.

The third email, which is the follow-up to that, is the number one problem that people have written me about. I have enough data now, and I’ve been doing this long enough, that I can write this third email. It’s actually the biggest thing people struggle with is making more money and pricing. It’s a natural upsell for my book, “Double Your Freelancing Rate,” and I get a lot of…

I want to say I get maybe sell between $100 to $200 a day off that book, which I wrote last August. Even a year into it, I’m still getting consistent revenue. A lot of that, I think, is because I have this sequence setup that happens when somebody joins my newsletter.

It’s not a hard sell at all, it’s just like, “Here are some blog posts that I’ve written about pricing, or if you want to read 100-plus pages about it, here’s a book.” It works pretty well.

Colin: What are some of the other ways that you’re using, or thinking about using emails, either like autoresponder series or lifecycle emails, which are essentially like different names for the same thing, but… [laughs]

Brennan: It does get a little more complex than that, and I do send emails out based on my purchases. When somebody buys like a [inaudible 06:33] , I’m going to email them, I think I have it going out 20 days later, where I ask them what they thought, which is just fishing for testimonial. I also promote my other book that way, because usually Double Your Freelancing Rate is the first book that they’ll come across. Can you hear me OK?

Colin: You broke up a little bit, but, yeah, it seems to be OK now.

Brennan: I do have some lifecycle emails that go out based on purchases. Eventually, my goal is…It’s funny. We’re recording this on Tuesday, July 9th at 3:00. At 2:30, I just replied to an email from somebody who wrote me an email, saying they just joined my list a few weeks ago or something. They wanted to know if I had any resources I could provide on how to get more clients through your website.

I replied saying, “I literally wrote the book on that, right?” and pasted a link to the book. There’s definitely some room for improvement on how I can better expose the stuff I’ve done to my web as a whole. That’s going to be…when I have the time, I’m going to do a very big project that will hopefully allow me to wrangle stuff in.

Colin: You and I have talked about the idea of rather than sending people to a landing page, you send them to a lifecycle email course or an autoresponder course. I think we were both talking about that as an experiment we wanted to run last time. Have you implemented that? Is that in production now?

Brennan: I have. Actually, about two weeks ago, I put up a drip email course on Planscope. If you go to the Planscope site, there’s, in the bottom-right, I’m using Drip by Rob Walling, which is just a thing that’ll track actual visitor to trial conversions. It’s basically meant for [inaudible 08:44] . I’ve gotten a few…I think I’m getting about a five percent conversion rate from people who joined the course so far.

I’m only two weeks in, so I don’t really know how it’ll pan out, but it’s already…because it’s a lot easier to get somebody to put in their email address than it is to whip out the credit card and start off a trial. Likewise, with the book, if you’re sending random traffic to a landing page or a [inaudible 09:14] .

Colin: We’re breaking up a little bit.

Brennan: …who don’t trust it, they don’t know who you are, then it’s going to be very hard, I think, to sell them. I think we cut out again.

Colin: Yeah. Can you jump back to the bit where you’re saying if you send people to a landing page when they don’t trust you?

Brennan: Yes. If you send traffic that doesn’t know who you are to a landing page, and you’re asking them to buy something, the likelihood that they’ll buy it if they don’t know who you are is pretty low. You need to break down a few different trust barriers that will allow them to be comfortable enough buying your thing.

One of the best ways to do that, I think, is to build up a relationship over time, and to just ask them for an email address, maybe give them something immediate in return, like a PDF or lesson one of a course and, basically, use that to build up trust and give them free value over time. Then ask for the sale like a month into it or something.

Colin: Do you have any advice for people on how to find the content for the course, relative to their product? How do you make a decision on, “I should write about this, because my product’s about that?”

Brennan: It’s easy if you’re selling a book. You just take out themes from the book, and deliver it. For a software product, one thing I’m really big on is stepping back. I sell project management software, but that’s just one facet of a company that has clients’ needs. There are a lot of other needs that they have.

My email course is a five-day “Become a Better Freelancer” challenge, and I basically just took the…One of the benefits of having a newsletter is you can practice these courses through your newsletter. You can have a four- or five-part series.

I got feedback from it and I was able to modify the underlying content, and then put it into a lifecycle email course that I put out.

In my case, I knew that the people who typically bought Planscope were freelancers or small teams that they were trying to get their head around project management and managing clients and making more money and better scheduling themselves and stuff. I just took all that info that I knew about them and wrote a course — just a five-part series on how to…”Five Quick Wins That Can Improve Your Business.”

Obviously, the overarching theme is, if the topic is on transparency with your clients, I will plug Planscope and say, “One of the reasons I built Planscope is to make this problem a non-issue.” It’s a very subtle way of marketing your own product.

My benchmark is, if I stripped out anything sales-related for any of these emails, they should still be valuable to the reader. You should still want to read it, or it should still be something that somebody walks away better off than they were before they read your email.

I see a lot of people botch these up, where they do these really hard-sell emails, and there’s nothing of value. It’s a very one-sided email. All you’re doing is saying, “I want your money.” You’re not actually providing value to them in exchange.

Colin: You mentioned…I think a few things came up in what you were saying, as far as rules of thumb. Always provide value, and then I think your course on Planscope is a five-email course. What’s the spacing between the emails? How do you think about things like that?

Brennan: Some people say do a month course with multiple days in between. Mine’s literally a five-day back-to-back course. I could probably start experimenting with different types. But, for the time being, I don’t really see a lot of benefit. If I was selling a big, “Pay $1,200 right now, that’s it,” then you might want to invest a lot more time into building that relationship.

I think if all I’m asking for is to start a trial with this SaaS, I don’t think they need a month to do that.

Colin: That makes sense. Tailor it a little bit for the type of product you’re trying to sell. Yeah, that makes a lot of sense. Any other rules of thumb that you use when building these series of emails?

Brennan: Yeah. I won’t really aggressively promote anything — or even non-aggressively promote much — at the beginning. At the beginning, it’s all about them — understanding their needs, empathizing with them.

Later on, conveniently, it’s basically gluing…”We’ve defined the problem. This is the problem. Here’s data, or here’s what I think on how to solve that problem.” Then I will loosely link that with different products that I’ve had. They could be a free product — it could be a blog post I might have written, it could be a podcast episode — or it could be a paid product.

I don’t really draw a distinction between my newsletter and a book. The way I look at it is, you get lower value from the newsletter than you would out of a book, because a book is a very concerted effort by me to really focus on one problem and go really in detail on that. If you want to learn about that, there’s an exchange. There’s a monetary exchange. You buy the book, and you get a solution to that problem.

I don’t intentionally make it so my newsletter is nothing more than really elegant marketing. My newsletter by itself I think is very valuable, and people have said this, even if they don’t buy anything ever.

I look at it as, if the book is 10 to 1 — if the book is like 10x the value that the newsletter delivers — and that’s $50 for that book, then my $1,000 workshop is 100x or something. I try to peg it according…I forgot who…I think it might have been via Nathan Barry, Chris Guillebeau — I can never pronounce his name — I think he said something like, “You should always deliver 10x on the money you ask.”

Colin: I’ve heard that before. I think Patrick McKenzie might have even brought that up as well when he thinks about pricing. [laughs]

Brennan: I think we all…yeah. I make it very clear in the marketing, even, for my book. If you can just raise your rate by a dollar, that’s still a win because if you’re working even 1,000 hours a year, that’s $1,000 you’re going to make more, just by being able to do that.

Now, most people will go substantially higher, so the value they get is huge. You can get value out of a newsletter, but you can get more value out of other avenues. I really try to just make that obvious and evident in what I’m doing.

Colin: For someone getting started today, who maybe has a product — maybe they have a book that they’re writing — how do they get started with email, with building a list? How do they get attention for themselves? What would you recommend?

Brennan: It’s a good question. I was talking to somebody on Twitter today. He was like…It actually took me by surprise, because he kind of said, “Of course it’s easy for you to sell stuff, because you’re well known in that niche.”

I’m like, thinking back a year ago, no one knew who the hell I was a year ago. I think I replied saying something like, “Anyone with a name has been a no-name at some point.”

Planscope literally stagnated for a while, when I did the traditional startup-y, “Launch your product, think that people are just going to flock to it,” and then get frustrated and you’re like, “I’m going to run paid ads,” or “I’m going to do the whole blogging thing and that’ll just send people and they’ll buy.”

Planscope started taking off when I started focusing on creating value through my newsletter and through these books and stuff like that.

If you’re thinking about creating a product, whether it be…I don’t see a big distinction between a book or a software product. At the end of the day, they both solve problems. But what I would start doing sooner than later is really focus on building up the customers who are going to be the buyers for that product, and offer them something of value.

Over-deliver value as much as you can right now, and it will — it sounds cheesy — but it establishes good karma, and people will just want to naturally buy stuff from you because they already know you produce great stuff. You can use it to learn about what you’re building.

One great thing…Stop building stuff in isolation. Write a book collaboratively with future customers or even current customers if you pre-sell.

Colin: It’s funny. Your comment about nobody knowing you a year ago. Nobody knew us — Customer IO, me, or anything — a year ago.

Brennan: No one knew Patrick five years ago.

Colin: Yeah.

Brennan: There’s no predestination when it comes to this stuff. We’re not Calvinists.

Colin: I think all you have to do is start somewhere, but the advice that you’re giving — about focusing on delivering value now, and that will pay back later for your business — I think that’s really sound. It worked for us. It seems to have worked for you, too.

Brennan: Frankly, a lot of people think it’s the old hockey stick idea. My newsletter was built one subscriber at a time. My customer base, one customer at a time. There’s no…I like the predictability of a nice, linear, upward growth.

But I think a lot of people get discouraged when they launch, say, a SaaS and they have two paying customers or something. But, yeah. We were all…I was there. We’ve all been there.

Colin: Absolutely. I think that’s about it. Where would you want people to go if they wanted to get onto your list? What’s the URL for your list?

Brennan: My list is FreelancersWeekly — “Freelancer” with an S — Weekly, dot com. Actually, you join my list and then the thank you page has every product that I build, so that’s a good way to get there. If you want to see products without needing to give me your email, you can go to, and I have an About page and a Products page and stuff.

Colin: Thanks so much, Brennan, for taking the time and sharing your knowledge with us. We really appreciate it.

Brennan: No worries, Colin. Thanks.

Colin: Take care.