How to Avoid the ‘Idea of Entrepreneurship’

My guest for today is a freelancer, turned agency owner and entrepreneur. His first introduction to working for himself was doing side-work after hours.

This eventually grew to the point that he was able to quit his job and freelance full-time.

He expanded to a physical office and had eleven full-time salaried employees with clients all over the world.

Family and health reasons forced him to step away from his brick & mortar agency while moving into software and online training.

Now he makes his living by providing great software and products to freelancers and consultants from his upstairs office, with his wife and two girls just a room away.

He is currently the founder of, a project management tool built for consultants and he is the founder at Double Your Freelancing where helps 24,000 freelancers every week with his weekly newsletter.

Now, let’s hack …

Brennan Dunn.

In this 41-minute episode Brennan Dunn and Jon discuss:

  • Never falling prey to ambivalence
  • Why you need to keep showing up day after day
  • Growing your business doesn’t happen overnight
  • Taking his MBA on the spot
  • The one thing that caused Brennan’s biggest business mindset change
  • Freelancers — are they entrepreneurs?
  • The importance of having a “road map” in business


The Show Notes



How to Avoid the ‘Idea of Entrepreneurship

Voiceover: Welcome to Hack The Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jon Nastor: Welcome back to Hack The Entrepreneur. I am so glad you decided to join me today. I am your host, Jon Nastor, but you can call me Jon. My guest for today is a freelancer, turned agency owner and entrepreneur. His first instruction to working for himself was doing side-work after hours. This eventually grew to the point that he was able to quit his job and freelance full-time. He expanded this to a physical office and had eleven full-time salaried employees on payroll with clients all over the world. Family and health reasons forced him to step away from his brick and mortar agency while moving into software and online training.

Now he makes his living by providing great software and products to freelancers and consultants from his upstairs office, with his wife and two daughters just a room away. He is currently the founder of, a project management tool built for consultants, and he is the founder at Double Your Freelancing, where he helps 24,000 plus freelancers every week with his weekly newsletter. Now, let’s hack … Brennan Dunn.

I want to thank today’s sponsor, Freshbooks, for making my life easier. What is the one thing that I am no good at? I am horrible at staying on top of my bookkeeping and accounting for my business. But now, rather than losing receipts and handing my accountant this giant, messy box of papers, Freshbooks has this amazing app for my iPhone and lets me instantly take pictures of receipts and sort them by touching a couple of buttons.

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Welcome back to Hack The Entrepreneur. We have a brilliant guest today who I’ve been looking forward to speaking to. Brennan, thank you so much for joining me.

Brennan Dunn: Hey, what’s going on, Jon?

Jon Nastor: Not much. This is going to be fun though.

Brennan Dunn: Yeah, I’m excited.

Jon Nastor: Excellent. Let’s jump straight into it. Brennan, as an entrepreneur, can you tell me what is the one thing that you do that you feel has been the biggest contributor to your successes, so far?

Never Falling Prey to Ambivalence

Brennan Dunn: It’s funny because my natural gut reaction is to go into specific tactical things that I’ve figured out, or whatever else. But to be honest, it’s just coming in. Doing a lot of small things over and over again, and not letting myself fall prey to ambivalence. Showing up each week, producing content, talking with people, talking with customers, and doing that over and over and over again. What’s going to happen is that it’s snow-balled into this business now that not only pays my bills, but it also gives me a pretty good lifestyle.

Jon Nastor: Nice. Not falling prey to ambivalence. It’s an interesting way of looking at it. And the small things over and over again. Do you mean that it’s just necessary to keep going? The small things that don’t seem like they’re going to add up to anything, eventually do?

Brennan Dunn: Yeah. In my past, and in the experience of a lot of other people I’ve talked to, what ends up often happening is you get excited over the idea of entrepreneurship. You get excited over the idea of running a business. And then, once that you’ve produced your first product or you start a blog and write a few posts, you don’t really see any sort of result immediately. There’s the kind of delayed gratification.

Jon Nastor: Definitely.

Why You Need to Keep Showing Up Day After Day

Brennan Dunn: A lot of people give up there. I think the biggest monument or testament to success I’ve had — and the success a lot of my peers have had — has been even when you don’t have that initial hockey stick growth curve that you are hoping for, you just keep coming. Keep producing those blog posts. Keep going on interviews. Keep refining your products. Keep working on your marketing and everything else. You know, it’s a lot of trial and error.

I think a lot of people just get burned out easily because they’re expecting: start from scratch, release first product, and retire on the beach. And it doesn’t work that way. There’s the whole idea of that “overnight success” ten years in the making.

Jon Nastor: Yeah.

Brennan Dunn: I think a lot of us get caught up in the big success stories, but we don’t always look at the grunt work, I guess. The showing up and grinding your axe each week that needs to happen to get there.

Jon Nastor: Yeah. I feel like you sort of read my mind there. I just put a post out last night on my site that I call, “Live in Days, Work in Months.”The whole “Live in Days” thing is just me not getting too caught up in my work and really spending the time with my daughter and my wife. But then the “Working in Months” is something that I realized that I didn’t realize at first, but when I look back on it now … you can’t go into a project and think that you’re going to create this product, launch it, and by next weekend you are going to have made $100,000 and live on the beach. It doesn’t work.

Brennan Dunn: Right.

Jon Nastor: It just doesn’t. If it does, it’s because you worked for three months leading up to that launch and did everything you could in your power to make it an amazing launch. You have to get over the mindset that there’s these overnight entrepreneurial lotteries. Where, “If I just do enough of them, one of them is just going to take off and I’m going to make a million dollars.” And that’s it. It doesn’t work.

Growing Your Business Doesn’t Happen Overnight

Brennan Dunn: You see that a lot. You read different websites where they profile startup X that got acquired for so many millions or billions of dollars. I forgot who wrote it, but somebody wrote a blog post called “EntrePorn,” I think is what he called it? It’s true because there’s so many people who get caught up on the idea of entrepreneurship but don’t always realize that it’s not like …

It’s like getting caught up in the idea of body-building. The great body-builders are the ones who go to the gym daily. It’s not because they’re maybe genetically superior, well that probably has some effect, but for the most part they show up. They go daily to the gym and they’re the ones who get fit and have that beach body and everything else. We’re all looking for that magic pill. You talk to any successful body-builder or successful entrepreneur and they’ll tell you that that pill doesn’t really exist.

Jon Nastor: Exactly. I saw a quote from this famous guy who trains Olympic athletes, ones that have won amazing gold. I don’t know who, I’m not really that into sports. He was trying to find that magic thing that makes some athletes these star, world-class athletes. The guy’s answer was, “They’re the ones who can deal with boredom the best.” Usually, most people train . They work on their business. Or they do whatever it is they want to do until they get bored. That’s the part where we stop.

Brennan Dunn: That’s right.

Jon Nastor: The people who just…”Nope, I’ve got to keep going, keep my head down. I have to keep working through and working through.” Those are the ones who … I was like, “Wow! It has nothing to do with how fast they could run. What they eat. What time they wake up in the morning. What their routine is.” No, they literally can deal with boredom better than anybody else.

Brennan Dunn: That’s funny, because actually I got an email last week from somebody who had just read my last blog post. “Can you tell me how you’ve gotten to be pretty good at writing and how you can knock out this 4,000 word blog post in a day?” My answer was, “well, I’ve been writing a blog post a week for the last three years. That’s why.” Go to my archives. Go back three years ago. You won’t see what you see in that last blog post I just wrote.

Jon Nastor: Yeah.

Brennan Dunn: I think that that’s true with just about everything.

Jon Nastor: Exactly. All right Brennan, there’s a time in every entrepreneur’s life when they realize one of two things. Either they have this calling to make something big in the world and a difference, or they simply cannot work for somebody else. Can you tell us when this happened to you and which side of the fence you are on?

Brennan Dunn: My father was a business owner. So growing up it was interesting because I would go to my Little League games and he would be the only dad who was there every practice. Everyone else had their parents working nine-to-five. Three in the afternoon, my dad would be there at the practice and everything. It was like that for everything.

I was kind of raised with my parents around me. And now that I’m a dad myself and I have kids, I wanted that same thing for my children. I realized that it really did influence me a lot. It really did affect me a lot to have my parents, both of them, always around.

I had a really good job. I was early twenties, making six figures at an interactive agency. What ended up happening was my wife got pregnant and she wanted to live closer to her parents up in Virginia. We moved from Florida to Virginia. I didn’t know anyone up there. I didn’t know the business scene. I didn’t know what companies there were, and so on. So I ended up freelancing.

I was kind of forced into it. It wasn’t like I decided one day, “You know what? I want to own my own business. I’m going to start this.” I went into it out of necessity. What ended up happening was I built up this agency. People kept knocking on my door and asking me to work on their projects. I got to the point where I could either turn away work, or grow.

Taking His MBA on the Spot

Brennan Dunn: Not really knowing much about how to run a business, I decided to grow. Which meant I had to get into the whole payroll and dealing with business development so that I could know with certainty that I have enough money coming in each month to pay my expenses. It was a huge crash course. That was my MBA. I learned it the hard way, going through and kind of needing to learn on the spot. Before, I was selling my time, I was selling my experience to whoever wanted it hourly. And now I was running this business that ended up making me think differently about what I was doing in the world and what I was doing for my clients.

Started doing that and then over time it got to the point where — and you see this a lot, especially with consultants and freelancers — even though I had an agency and I had people working on my behalf, I wanted to eventually have a lot of customers paying me a little bit of money instead of four or five customers paying me a lot of money. I was kind of beholden to these four or five primary income sources. I got bit by the product bug. Started a software company. And then I started getting the training business kind of as a direct result of the other support tickets I was getting.

So I started this project management app. And I got all these people who were supposed to be writing in with questions about the software, who instead were writing in with, “How do I get clients?” or “How do I price myself?” That kind of led me to starting my side business — which is now my primary business — of producing the training that I wish I would have known when I went into freelancing blind. That I learned that hard way through growing this company, getting to 11 employees and two million a year in revenue, and everything else.

That’s the story, from employment to where I am now. Obviously it’s a lot deeper than that, but ultimately, I didn’t really have this wake-up call where I was like, “You know, I want to change the world,” or anything. I think what happened to me … It’s kind of funny. I have this milestone of “I want to be able to work from home, work around my kids’ school hours and be able to hang out with them a lot,” and everything else. That’s when I decided to sell my agency and start the product business.

Then I learned the hard way that it takes a while. A subscription software business … Let’s say you have fifty people paying you twenty a month. If you get five new customers this month, congrats, you make $100 more this month. Which, do that for years and you’re doing really well, but it takes a while for that kind of product revenue to make any impact in your revenue, in your finances.

For me what ended up happening was I started a software business and it was taking a while for it to be profitable. Just because $20/month takes a long time for that to make an impact. I started the training business, like I said, as a result of the support tickets. And when I realized I was actually making an impact was when I would get email from people saying something like, “Hey, we haven’t met before, but I bought your book, and I’m now able to get married sooner than I thought.”

To me, that’s how I’ve changed the world. I’m not an Elon Musk. I haven’t started a space company or whatever else. But to me, for my small group of customers — the few thousand people who I can claim now as customers — I’ve changed their world. Therefore, I’ve changed the world. That’s how I look at it. I’m not looking to create this billion dollar company that radically transforms the way that society works or anything. But I’m changing the lives of a lot of people.

The thing that I love about the business that I have now is I don’t need to … When I was a consultant or freelancer, if I wanted to change a client’s life, I had to show up, do a lot of work, do a lot of custom coding, designing, whatever else and then I could change their life by building something for their business. Now, I can build things once and affect a lot of people simultaneously. To me, that’s been far more rewarding, at least personally, than the handful of clients I had as a consultant. Now that I just have broader reach, if that makes sense.

Jon Nastor: Yeah, it does. Makes perfect sense. The difference you’re making is absolutely real and powerful, man. That’s awesome.

Brennan Dunn: Yeah, it’s funny because there’s one thing to be said about waking up in the morning and seeing somebody you don’t know, who you didn’t ask for money, has paid you. That is a huge eye-opening experience for me. Most of us, we’re used to salary payments, it’s expected. I’m showing up and sitting in this cubicle for forty hours a week, and I expect every two weeks for this much money to go into my bank account. That’s the norm.

And then you have consulting or independent work where you issue invoices and you’re basically saying, “I just worked forty hours for you, and here’s my hourly rate; therefore, you need to send me a check for this much money.” It’s kind of the same thing in a way as employment.

The One Thing That Caused Brennan’s Biggest Mindset Change

Brennan Dunn: But then you get to products and you can literally have somebody who goes to a website that you wrote once. Who purchases a product that you created once. And now they’ve sent you money without you requesting it. That first sale I ever made that way, was probably the biggest life-changing, epiphany moment for me as I look at business — from birth.

I’m used to the whole, “You need permission. You need to ask somebody. You need to do something in order to get what you want.” Which in business, is typically money. I need to apply to the job, show up at the job, and do good work, and then I’ll get paid every two weeks. Or I need to do great work for my client and then I’ll get paid for that invoice. Now it’s more like I can set up something that’s a flywheel that I put together once and now people are responding to that without me needing to show up and spend time making that sale happen. That was a big eye-opener for me.

Jon Nastor: Yeah. That first sale is always in so many of our stories. That’s the epic moment where somebody somewhere transferred money from their PayPal account to yours for something digitally that you made. It’s amazing. Even if it’s for $5.00 that first time, I don’t think we ever go back to thinking the other way again.

Brennan Dunn: It doesn’t get old. It doesn’t. Eventually, if you’re doing well, you get to the point where you need to disable email notifications, which is a good place to be at.

Jon Nastor: Right.

Brennan Dunn: Even still, just the idea that … I went on a cruise with my family a few weeks ago and I was a little worried because I’m typically used to the whole — especially with consulting — “if you don’t work that whole week, you don’t get paid for that week.”

I went on this cruise, had my VA manage my inbox, and was able to respond to everyone who emailed me and everything else. I come back and I’m like, “Wow, I just paid for that cruise without needing to!:” That sort of thing, right? You start out at first, when you’re making twenty bucks a day and you’re like, “Well, this is my coffee budget. It just paid for my lunch.” And then it gets to the point where it starts to be able to pay for your house, and your car, and your trips and everything. It still floors me to this day.

Jon Nastor: Yeah. I like how you mentioned we keep those notification emails in our inbox up to a certain point. I did that for almost a year at first and then it got overwhelming. Still I just wanted to see them. And then I was like, “Okay, it’s not annoying, but I’ve got to put these somewhere else. It’s distracting.”

Brennan Dunn: That’s a total first-world problem. When you are being sent too much money that you need to stop being told that you are making money.

Freelancers — Are They Entrepreneurs?

Jon Nastor: Exactly. Would you agree or would you say that freelancing isn’t entrepreneurship or is?

Brennan Dunn: I think it is. I think it can be. I think most freelancers, unfortunately –and this is actually what the kind of work I do now is trying to fix — most freelancers go into freelancing with their employee hat on. They’re selling themselves on their technical credentials. They’re basically planting their flag and saying, “I’m a talented web designer. You can pay me for fifty bucks an hour and I will bang on my keyboard for you for $50/hour.” That’s how most freelancers operate. Unfortunately though, that’s just basically employment, but under a 1099 instead of a W-2 arrangement.

The thing that I try to advise freelancers and consultants to move towards instead, is to really position yourself as a product. Learn how to market yourself from the, “here’s benefit or the benefits I’m able to deliver to my clients.” Basically, pitch yourself like I would pitch a course or I would pitch my software, the same sort of thing. I’m not pitching my software based off of the language I use to write it, how many lines of code there is, and everything else. I sell it on the benefits that the software delivers.

If you can learn how to do that for your time, you can eventually start to productize yourself. You start selling your availability — as you would a product — and what you are able to do. From the perspective of the buyer and the client, there’s no difference between paying you a thousand a month to solve a problem or paying a software product a thousand a month to solve that problem. As long as the problem gets solved, they don’t care.

If you can position yourself and represent yourself as a product — I know it sounds weird, especially if you’re not used to doing that — you learn, “Who is my customer? What needs do they have? What problems do they have? What solution am I offering, and how am I offering that? What objections do they have”? You do that maybe for your time at first, then you can start to incorporate more turnkey products that you can use to deliver that whole need that somebody has.

Let me give you a good example of this. I’ve got a friend who helps make websites more money: whether that’s more leads, or more sales, or whatever that might be. When he started out, he was selling himself — or selling his product service — as, “Pay me monthly, this much a month, and I will run experiments on your behalf. I will tailor the way that your website operates with the explicit goal of increasing your profit. Increasing your sales.” Over time, what he’s been able to do is incorporate custom software to help deliver that increased sales to his clients and start to also delegate out things to juniors, to other people.

The clients are still getting that same end product, but he’s able to start to withdraw himself out of the hourly swapping engagement to deliver that product to his clients. I think that’s a great way to make that transition from selling your time to selling a turnkey product. That’s what he done and that’s the golden path from selling time to selling something that doesn’t require your time as an input as a requirement to fulfill the transaction.

Jon Nastor: Excellent. I love the way you started. Really it’s just a mindset change between a freelancer being an entrepreneur or not.

Brennan Dunn: Totally.

Jon Nastor: You’re like, “they are, yes.” And then, “well maybe.” I’ve talked to people who are freelancers who absolutely think they are entrepreneurs, and other ones who absolutely it is their consulting job that they do and it is exactly like they work for that company or those companies. They just get paid differently.

Brennan Dunn: They’re all, legally, entrepreneurs. They own their own business.

Jon Nastor: Legally entrepreneurs.

Brennan Dunn: On paper. But that doesn’t mean that they are what you and I might label an entrepreneur.

Jon Nastor: The productization of your services or of what it is you do. That’s the way to transfer and be able to trade exact hours for payment.

Brennan Dunn: That’s right.

Jon Nastor: That’s cool. Let’s move to struggles and failures. As entrepreneurs, as human beings in general, one of our greatest struggles is the fear of being wrong, making mistakes, and failing. Brennan, can you walk me through how to be wrong?

Brennan Dunn: How to be wrong? Interesting question. You mean like what somebody does to-

Jon Nastor: You.

Brennan Dunn: I’m guess I’m trying to figure out exactly-

Jon Nastor: It can go one of two ways, but I would like to see … You in your business decide to do something. You decide to take something on or go in a certain direction that turns out to be completely wrong. How do you pick yourself back up off of that and decide to redirect and to not get mowed over by this issue?

Brennan Dunn: By the depression that might ensue, you mean?

Jon Nastor: Yeah. To me, that’s what it is. If I’m fully on to something and then it turns out that this doesn’t work or this deal doesn’t go through. And I thought, “Wow, I spent a couple of days. Geez, that was brutal.” I want to know how you deal with this as an entrepreneur in your business.

Brennan Dunn: Sure. I’ve done plenty of things, whether it be products or initiatives or whatnot that in my mind failed. I think two things are important. The first is to realize that failure is rarely binary. It’s very rarely I flat out failed or I’ve flat out succeeded. Maybe you didn’t hit the number of sales that you wanted to get. That’s the first thing, is that it’s very rare to have a full-on like … Actually, let me give you a great example of this. You see a lot of people who launch products, right? They get very obsessed over launch day.

They are very like, “going to launch and TechCrunch is going to pick it up, and all these bloggers will write about it, and then I’ll be good to go.” Then they do their launch and maybe they get a few customers, or they don’t even get any customers. They look at it as a failure. The way I look at it is, each time a new prospective buyer comes in front of you and your product, you’re launching. You’re launching to them. They are now hearing about you for the first time ever and for all intents and purposes you are launching to them. That’s one thing, where you need to look at it like that.

The second thing is when things don’t go the way you want. Let’s say you run a new ad campaign that just bombs. Don’t look at it as you lost money. Think of it as you paying for data. You’ve learned about why your audience is not responding to the pitch that you put in front of them. You’re learning about why your sales page didn’t convert as well as you thought. There’s an opportunity cost. Maybe the people who were exposed to that sales page you’ve lost for good, but you can learn from that. You can see, “where did I lose them? What objections did I not overcome?” Things like that. That will make you stronger for the next cohort that you launch to.

Launching, I think, is overrated. It’s one thing to say, “okay, we’re going to do a big media push.” When I launched my SaaS, my software product, I was obsessed over launch day. I launched and I got maybe a handful of people who started to try the software and everything. At first, I was really depressed over that. Not depressed. I was just kind of, “meh.” That’s not what I wanted.

The more people I talked to and had run business like that and had been there, the more I learned that the businesses that succeed do not obsess over something like that. They obsess over, “What can I learn from that first launch and make it so the second, the third, the five hundredth, the thousandth, the subsequent launches are more profitable for us?” They learn from that and they get up and do it again. And then they do it again. And so on.

Jon Nastor: Nice. So level-headed.

Brennan Dunn: I try to be.

Jon Nastor: It sounds great when you say it. What seems in our heads sometimes as like a catastrophic sort of failure. You do, you hype up this launch day and you get a couple of customers. You take that as something you did is not either up to snuff or not valuable enough. And you sometimes start questioning, “Should I even be doing this? Should I just go get a job?”

Brennan Dunn: “Maybe this isn’t right for me.” To be honest, you see that happening a lot, especially with freelancers. They get on a lucky streak where a client comes at the right time and then another client comes at the right time, and then they have a lean month or a lean few months. They give up. They’re like, “Well, obviously, this isn’t meant for me.” They give up and they go back.

I think if you can step back and have a lunar perspective of your business, where you want to be, and your journey along that path. Very few businesses have a straight, linear, predictable path. People sometimes backtrack. Sometimes they skip ahead a little. For the most part, it’s very jagged. I think the smart business owners are the ones who understand that and push through.

Jon Nastor: Yeah, exactly. It’s harder to realize at the beginning stages of your business, but over the years you do get used to those things. Things that would have knocked me out of it before, I notice myself days later being like, “Wow, that didn’t even phase me at all.”

Brennan Dunn: Right.

Jon Nastor: I guess it’s just experience and knowing that this is how it works. It’s not just a linear …

Brennan Dunn: That’s right.

Jon Nastor: There’s this idea I’ve been working with called the entrepreneurial gap. Meaning that, as entrepreneurs, we are always sort of looking ahead. We are always looking towards the horizon. Always setting goals ahead of us: three months, six months, a year, five years ahead. And sometimes before we even get to those goals, we set five or ten more, loftier goals. And we never seem to stop and turn around. Look at where we’ve come from and appreciate all that we’ve accomplished and done.

We’re always, “when I get there in six months, when I do this, though, it will be better. It will be better. It will be better.” You said you went on this cruise with your family and then had to stop and realize, “Wow! I just paid for this whole cruise while not working!” That’s amazing. If you were to, right now, Brennan, for us, stop and turn around and look at what you’ve accomplished up to this point, would you be happy with everything that you’ve done, where you’ve gotten, and what you’ve learned?

Brennan Dunn: Very much so. I think, to go back to what you were just saying, I journal weekly about, “What did I do in my business this week? What immediate impact do I know it’s had? And what other big events have affected the business this week?” That alone, has been great. You know you are going to have crappy weeks. Being able to go back and look at a business journal and see, “Okay. Yes, this week was bad, but normalized trajectory of the business is still on a good path.” You can look back and see the highlights and successes and everything else. I think that’s what it is.

To be honest, there are weeks when nothing happens, nothing sells. You are getting worried. You are thinking like, “Is something wrong? Have they realized I’m a fraud?” Something like that. You start to have these emotional doubts. I think the best way to overcome that is data. I can pull up my monthly revenue graphs for the last three plus years and it’s up and to the right. The movement is up and to the right. That’s the movement that any healthy business should be going toward.

The Importance of Having a Road Map in Business

Brennan Dunn: If you don’t have that, and you are reliant on your short-term emotional outlook, then you are going to set yourself up for failure. I think also — to go back to your lofty goals and that sort of thing — I see a lot of people, myself included, who try to set these, “One year from now I want to be here.” The problem is, you can’t convert that goal into a to-do item. It’s not like doubling revenue can be a task that you accomplish. I do have these “where I want to be” twelve months from now goals set up, but I deconstruct them into quarterly, monthly, weekly, smaller goals that get me there. It’s like thinking, “I’m in Virginia now. I want to drive to Chicago.” I have a general idea in my head about the direction that I need to drive in. But until I can actually plan the different legs of the trip on a map — not that nowadays do that anymore, right?

Jon Nastor: You just use the GPS and we listen to what she says.

Brennan Dunn: Exactly. But you need to treat that goal like trying to get to a far-flung location, and realizing that the way to get there is not to just point your car in a general direction and drive. Instead, to come up with a road map that will get you there. That’s why I think it’s really important to deconstruct these high level …

Imagine yourself sitting on a beach with your daiquiri. With your laptop on your lap, and seeing this amazing bank account balance. That’s noble. Go for it. Great. But realize you need to deconstruct that into more tangible, actionable to-do items to get there. I think it’s easy to dream. It’s easy to dream about that daiquiri on the beach with your laptop, but the place that I see most people falling off in actually pursuing that into its next logical conclusion. Which is, “What steps do I need to take to get there?”

Jon Nastor: Yeah. That was well said. I guess you’ve got to enjoy that daiquiri on the beach now. I agree fully that you do need goals. I know from talking to so many people, and myself, that sometimes we don’t even allow ourselves to celebrate and congratulate ourselves on those goals before we already set new ones. It’s always, “When I’m there, when I’m there.”

I’ve been following you on Twitter now for the past seven or eight months. I know that you are very much respected, very much looked up to, and very much admired for what it is you do. Respected for it, man. I would hope that you really do stop. You do. You journal it. That’s awesome. I hope that you do really appreciate where it is you are, because it’s amazing, man. It’s really, really cool.

Brennan Dunn: Yeah, thank you.

Jon Nastor: Brennan, we’ve got to talk in passing about your businesses. Could you specifically tell the listener where they can go find out more about you, please?

Brennan Dunn: Sure. The best place is probably That’s my hub site that I’ve set up over the last year. That has my weekly blog posts. It has my podcasts. Also there’s a contact link if you want to email me about anything. I’m also on Twitter like you mentioned, @BrennanDunn. Those are probably the two best places. I also have, which is my software company. If you are in the market for project management software for consultants and agencies, I have that for you.

Jon Nastor: Excellent. I will link to your Twitter, Double Your Freelancing, and, as well as some other things we’ve mentioned during the show in the show notes for you just to make it easy for you to find. Brennan, please, thank you so much for taking the time to join me today. Keep doing what you’re doing, man, because it’s really, really awesome and inspiring to watch.

Brennan Dunn: Awesome. Thanks for having me, Jon.

Jon Nastor: My pleasure.

Brennan, thank you so much for stopping by today and you just … man, just thank you. I’ve wanted to talk to you. My friend, Nick, actually told me before I’d even launched the show that I have to have Brennan Dunn on one of these days. Sorry it took me seven months at this point, but I’m so glad that you stopped by. That was great. I love your story of starting out freelancing, building into this huge agency, and then stuff happens in life. And now you are working from home and doing amazingly for you and your family, and you literally just get to walk upstairs as your commute to work. It’s beautiful. I love it.

Brennan said a lot of smart things. He said a lot of smart things, didn’t he? He did. He did. But he said one thing. He said one thing. Did you get it? Did you hear it? Let’s do it … let’s find the hack.

Brennan Dunn: But then you get to products and you can literally have somebody who goes to a website that you wrote once. Who purchases a product that you created once. And now they’ve sent you money without you requesting it. That first sale I ever made that way, was probably the biggest life-changing, epiphany moment for me as I look at business.

Jon Nastor: And that’s the hack.

Yes, Brennan. Yes, yes. That first sale where during the day — or you wake up — you get that notification on your phone. I guess at the time it was not on a phone, it was just to my computer, but now you get it to your phone — and it’s amazing. That one sale. I believe my first sale was like $7.00 or something and it completely changed my life in the fact that, “Okay, if I just do this thousands of more times or just do it for more money,” I literally didn’t have to physically go anywhere. I didn’t have to physically give somebody anything. That’s amazing.

I talked about this back, I think, Episode 8. If you haven’t listened to it, you should go back. Stu McLaren, he’s a fellow Canadian, has an amazing story that I heard years back at a conference, actually in Las Vegas, he was speaking at. It was amazing. He has this beautiful first sale story. I think we all get them. If you haven’t had that first sale, don’t go for something big. Go for something small, that $7.00 sale, if you can. It does something to your mindset and it shifts your brain in a way that you will not go back to.

As Brennan said, it’s the one thing that changed him. The greatest change or epiphany in his business mindset was just getting that first sale digitally through the Internet. Where somebody literally takes money out of their bank account and puts it into yours. It’s powerful, powerful stuff. We can get ahead of ourselves sometimes thinking, “Well, when I make $5,000 or $10,000 a month it will be amazing. I can live on the beach.”

But you have to start with that first sale. That first sale can be as small as it has to be to get you to get that first sale quickly and get that sort of win into your system. Because it will change you. It will change your perspective and it will change your mindset. And it will instantly, even though it’s such a small amount of money to pay for a coffee. At that point, you realize that everything you’ve heard about this online business thing really is true, and you just have to now scale it to a level that you can live and support your family off of. Which you absolutely can do. So Brennan, thank you so much. That was awesome.

All right, guys. You should check out the site, it’s great. Get on the email list. Every Sunday I’m sending it out. I still have four more Seth Godin books to give out. If you would like one, get on that email list. I’m giving out two every Sunday, mailing out actual physical, beautiful books that Seth made back in December of last year. I would love to give you one. Get on that list and you might win next Sunday.

Please, if you are not one of the 258 people that left me a review and a rating on iTunes, I would absolutely love it. Go on your phone or just to iTunes. Look for Hack The Entrepreneur or go to It will take you straight there. I would love a rating and review. It helps the show so, so, so much.

All right guys. This has been a lot of fun. I appreciate you taking the time — half hour here — to stop by with me. I know you have a lot of choice, and I absolutely love that you listen to the show. Thank you again, and until next time, please keep hacking the entrepreneur.