Episode #166 – Ian Dunlap On How To Guard Your Freedom By Adding Another Relentless Profit Stream To The Mix

by John McIntyre

Ian’s dad was an entreprenuer and it rubbed off.

When he was first introduced to the marketing rabbit-hole through A Dan Kennedy book…

there was no looking back.

Through consulting, he learned many hard lessons about managing clients and money.

What he enjoyed most though was the AUTONOMY.


So when a friend called him up after the recession and told Ian about the money he had scooped by investing…

It drew Ian into another world.

Soon he was spending every day studying markets with the same zeal nerds play video games.

His “Call of Duty” was money.

So today he’s coming on the show to share his journey through marketing to investing.

Showing freelancers and other entrepreneurs how to put your money to work for you.

Like a rabid, relentless money-sucking terminator that helps secure your freedom…

with one more revenue stream you can count on.

He made a quick $3500 in the morning hours before we recorded this episode…

So I know you’ll find it as exciting and informative as I did.

In this episode, you’ll discover:

  • 3 secrets of a “freedom” career. Save yourself years of frustration, confusion and anger.
  • Why Ian immediately came to know, like and trust Dan Kennedy because he reminded him of this man.
  • Can money buy happiness? If you can’t do this one meaningful thing…nothing else matters.
  • The “All-star team” way to dip your toes into the investing pool.
  • How to create wealth for your kids future by doing the bare mimimum right now (So easy!)

Email Marketing Podcast Episode 166


Intro and outro backing music: Forever More by CREO

David Allan: Hey, everybody – We’re back with another edition of the podcast. I’m David Allan and we have an interesting guest for you today which is taking a slight departure. You’ll see what I mean in a moment. We’re going to talk about some things that pertain to entrepreneurship which most people may be overlooking or just not addressing in any way shape or form and you’ll see why this is important later because the family you have on today sort of live that and he’ll be able to explain it a lot better than I can. Ian Dunlop Welcome to the show.

Ian Dunlap: I’m super excited to be here. Thanks for having me on.

David Allan: Yeah it’s great to have you on. You know I didn’t know really anything about you you know at first until I read the articles you put up and so forth and it sounds like you’ve had quite the journey so that’s usually where we like to start. Let’s start right up front with Tell us about your origin story your superhero origin story. Tell us where you were where you came from and and lead us down the garden path where you’re at today.

Wonderful. So initially how I got into entrepreneurship is because of my dad. He’s had a construction company ever since I was a kid. So he blessed me with that gift of wanting to be entrepreneur. Fast forward later on. Finally have the audacity to reach out on my own and begin to do some things. And I went to a Dan Kennedy submit our way back in that day I think it was maybe 2003 or 2002 or. And I said holy. I didn’t know there was an industry where you can actually do marketing. So I was into you know fashion and different things that were hot but I didn’t know how to monetize that by you know listening to Dan and all of its

greatness speed on about how you can market and get clients. And my first client in Bloomington Indiana where I went to college at Indiana University was a local insurance company there.

OK I was going to say now before we talk about that like how did you hear about that and what made you decide this is something I need to attend.

Back then it was the wild west so there wasn’t a ton of verified information so people were pitching Lam’s claim they were making a million dollars a day and you know all that crap back in the day and then whenever I would look because my dad would always tell me that sales and marketing are the two most important parts of the business. And then of course reputation ranch would just randomly look for marketing things in between classes and then I don’t know how I went down the rabbit hole of internet marketing. Right. And I think Corey Rudel And I think he was a man and one of my friends. No Bull. He said I got this book about time management. I don’t know who this guy is.

Hands down the most honest guy ever heard of business. OK.

I’m sure Dan would appreciate that.

And I said OK let me go run to the bookstore. Got the book and I was blown away. You know some of the teachings and I saw some of the old newsletters and then I really got wrapped up in learning you know through dad and his newsletter because back then I mean we’re older. There wasn’t a ton of information. You had a couple of books for a couple of magazines but there was not a proliferation of great info from people and wonderful podcasts like yours to help people who were beginning right now.

And so I’m always fascinated by how people are sort of you know the way that the way they find their way into this into this kind of world. So you know I like to hear those stories. It’s fascinating for me compared to how I got into it and so forth.

So you went to the seminar you’re surrounded by all these crazy entrepreneurs and the bluntness of Dan Kennedy and yes and so were you. Did you feel empowered coming out of there like I’m going to. I did. Yeah.

Yeah I feel empowered because a lot of the things that Dan would say I heard my father tell me early on because my granddad was in the military so he was very harsh and brash the way that Dan was and that got passed on to my dad. But now finally had like a friend. So I got the ultimate marketing plan the ultimate sales letter and I’m like now I have a blueprint to follow in those first sales letters and marketing plans I create it was terrible for the client I had they didn’t have anything but a sales force in the fleet came in. They will call no follow up. Right. We know how important you know things are respond to this. There was no follow up. Back in 2002 2003 of any kind so if a

person didn’t buy within 30 days they trashed delete and I said Hey why don’t we just send out something every week and just talk about some different areas in which they can be covered and then things began to converge and I began to tell my dad and he was like hey this makes a lot of sense. And he would put those things into place and his business I wasn’t compensated because he was paying for the school paid off radio. It was the it was equal trade off. But I know when he called me and said hey I think you’re really onto something that kind of empowered me to go on and start to pursue aforetime because before then it was a lot of hucksters out there to generate that information and they were promising the world but the results were not

coming. And so Dan was the first person who actually delivered on a lot of these promises.

Wow that’s high praise. Especially when you get started through it and at marketing I would say See the highest of praise I would say.

So you’ve got this local insurance client and like you said they had like a lot of things and no follow up. They had very limited marketing strategies in place. Did you start looking for other clients after that or were you.

I did. Then things got tough because you don’t know about how to manage your money for a client because it’s first client so I’m thinking hey I’m to cry every month I’ve made it king of campus. And then a 2005 Facebook as were available to college students so I remember the days when I could run an ad for $40 a week like Facebook. And so you know I would do other things like throw parties with my friends and we would make a ton of money because we would always spend $400 on ads and make five or six grand in a night. Right. Right. But then you had your hiccups of mismanaging money and then clients are not coming in or client does not want to pay.

They own the rights to that system and there’s nothing that you can do. So I’ve also had a decline as well. But I kept learning because I knew that I was on to something and with my dad. The one thing that I did see in comparison to other members in our family he did have a sense of liberation even though he worked a lot of hours right there was a lot more joy that he had because he found his sense of purpose and he had more money come in and people loved to say the money can’t buy happiness and they can’t buy the purpose or completion. But happiness is for sale. If you can’t provide for your family you’re going to be miserable. Yeah. So I saw that clearly in my family that worked the companies for 30 years and got a small retirement and then my dad will get

a contract. Six degrees would be jealous and I’m like but if you’re happy with what you’re doing why do you care what he made.

So I just kept down the path of entrepreneurship and find because once you sort of get into it at least I found it this way especially the direct response world of Dan Kennedy is now Albertsons open.

People we talked about off the air about that. You know you can’t and you can’t unsee this. You can check that box or what you want to say. Now you’re kind of like compelled to do something about it.

Yeah. And I think you have to make a clear distinction and the choice of either I’m going to go work the corporate route which there’s nothing wrong with that. And that’s what you truly want to do. But when I was done with college the recession hit shortly after and all of the friends who thought I was crazy for reading all these books in the library or in the Student Union when they were getting laid off they’re like hey how can I make some quick money. I’m like I don’t know because I’ve been on this journey now for two and a half three four years. I don’t have an easy recipe for you because I know people love to say that entrepreneurship is easy to read make all this money but that’s not always the case. Now

what I hate it is that people will glamorize how easy it was and it’s like any other endeavor any other sport. You have to consistently work at it. All in all I’m glad a lot of people like Ryan’s didn’t win that you had on him there telling you you have to work this every day. The facade of going on a yacht and making 200 grand from a launch and doing it every month I’m glad that’s been wiped away. But like you said as you see this the opportunity that is there is kind of hard to unsee it and go on the other path.

Yeah it’s fine.

And you’re right there has been like sort of you know it’s understandable why because it’s a lot easier to sell something that’s simple and easy and you know there’s a sort of like marketing and copywriting secrets to make your stuff after that stuff. Sort of Machiavellian things. You know you know you stay away from things that sound like work or learning or anything. Yeah. But yeah I think you’re right. I mean when you do encounter real people doing it for real. And certainly when I started to kind of people who were actually doing it and yeah they were working harder harder than any sort of job related people. But maybe they were doing it on their own terms and so you know there was a freedom to that.

Yes. You know there was a freedom to be able to do it when they wanted where they wanted with who they want and so forth.

It makes a huge difference. That sense of liberation even when my girlfriend was in the hospital two weeks ago with pneumonia she was in there for six days. I know a lot of my friends if they will work on someone somewhere they would have been able to take off six days and work from a hospital. And I’ve known you know other friends or family members will get sick and they would have like a two day furlough where they can leave but they would have to come back. I just don’t like that kind of life. And in entrepreneurship is a gift and a curse. But once you can find your own pocket for what works for you that’s an incredible thing when it goes right into the kind of I don’t know what the words are maybe but it’s like you don’t know when I had jobs.

I sort of hated working. You know I think all people experienced when you have a job and you’re not a good troll maybe and that’s maybe part of it but also what I would even if I was making not so much money or maybe it was making more money. The very fact is I was in control and I was doing what I enjoyed.

Yes because it was stuff I was reading and doing and applying it even if I was didn’t have a client I’d still be studying or doing whatever.

So yeah I think it’s the happiness comes from like you said you in sounds like what you’ve done is you found your purpose and that has motivated you to get into what you’re into. So take us up so you got out of college. What was the next step.

Then I moved to Atlanta and began taking clients and I went down the rabbit hole of being a consultant for a long time. Recently in the last three and a half four years I switched to investing which we’ll talk about in a little bit. I had clients over some of the most heart wrenching times of my life but also some of the most beautiful because you learning how to actually manage your business to manage clients keep the end flow and not focus on just having one client because if they walk away you’re in trouble. That’s why I like to refer to the masters of you know Dan Kennedy and halber and in direct response space but even like Auris and his books on

positioning and write all the books that he’s written on mark to them because I think entrepreneurs today because there’s so much information available on Instagram and Facebook they don’t read those classics and they’re going to run the same traps that I did. So for us five or six years like I had you know clients and I did that for a while and I was fortunate enough to partner with a big ad agency when I was around 29 to 30 and I end up working with rebought and Chevron and a couple other big clients so I got to learn how that infrastructure works which is really fascinating and for all of those of you who listen that right copy there’s a ton of money for you in corporate because there’s not a lot of good

content writers in the British you know a source like you have to learn how to navigate the creative with being a wordsmith. But there’s a ton of opportunity there. I think just a lot of people in this community don’t go after and reach it.

Yeah I think I think there’s a lot of truth in that. And you know I think from a lot of people perhaps it’s an us versus them mentality. It’s you know there’s a lot of there’s a lot of real obstacles mental and otherwise between that.

But yeah I think you’re right I think for somebody who’s looked to do stuff that the right choice you know that you can get in there somewhere. So you know when you were a consultant what sort of ways did you look at getting clients and stuff like how did you acquire the clients and what were you.

So a lot of it was doing what Ryan studen hates when someone does to him I would go to our go to a small business and say hey this ad is not going to pull well for you but the difference with me was I would I was a little bit more rogue so I would test ads all the time and I would bring data to them and say wow I think this will will perform better than I had more of a shotgun approach and I would just approach a bunch of people and that particular industry and then I had like a small newsletter probably that I should have sent out. I know Ben Seto’s you just sent it out to email every day and we’ll get into that. But I would send out an e-mail and say Hey here’s something that

could help me in your business. And I was a little bit of copy and it just sent this out in the e-mail solacing little blueprint to help them slowly build build a relationship. I will talk about it on social all the time. And then I will get clients in like that like hey because a person in a construction business a palm in business a dentist a dentist office they don’t know anything about building a marketing plan. They may know word of mouth networking events and a couple other things but they don’t have a full robust plan so and then in 2007 the book The Ultimate sales machine came out with just one of my favorite books of all time. My guy was his coach at home so he came up with the idea of targeting

100 companies or a best neighborhood strategy. And I began to use that so I would specifically focus on the industry at a time and go after. And then I would get one or two clients out of that mix and that process going and I really got good into real estate and construction areas just because my dad had been in the industry forever and I knew all of the pain points of what they needed.

Awesome. That’s awesome man. It sounds like you’re really out there playing what you learned. It’s nice to hear.

Yeah I mean I was listening to good times and bad times. Definitely. There’s a lot of things that I wish I would have done better have been more consistent in putting out content. That’s why I think the discipline of putting out an email per day. Right. That’s good. That’s something that I do now via video for those that follow me for investment advice and really just listening to those who came before me and just applied what they said and not try to remix or change anything that they said.

So right. Right. Yeah I think a lot of respect for you mentioned rhymes to earlier. People like that have a lower respect because they just love he’s just Khankan. I mean he just gets a done and he just gets stuff out every single day and it’s it’s crazy. So you know he’s super motivated and stuff but I mean there’s no reason why he couldn’t do that.

Absolutely. And I think for me it was just getting over my fear of what if I’m not good enough. There’s people who are. What if the content isn’t as good. But most people are going to create a video or post on anything. So and if you look at the success of Gary V in my opinion every V is nothing more than the newer version of Dan Kennedy or hauberk. Right. But he just puts out a ton more content. And of course technology was different. Back in the early 90s and early 2000s. But if you look at the things and principles that Gary talks about when the Superbowl we can’t I mean to me he is like a hybrid of Dan Kennedy and halber but he

just uses different media platforms. But the principles are exactly the same.

Yeah I think you’re right.

And you know he’s got that one thing that obviously a lot of these people have in common is this is a very strong personality they make they make delineations they draw lines in the sand where it’s like this is where I’m coming from and this is what I think is the best. And you may think otherwise but that’s for you to think you know. This is where the problem is and they’re not afraid to stand up for what they think.

Absolutely. Yeah same thing with Ryan and Perry Marshall. Clear line is saying get it done just execute don’t overthink it. That’s one of the things that I wish if I can go back 10 years I would tell myself I’m just saying don’t worry about it execute it to fails. It’s OK it’s going to cost you that much. Right. But having that confidence over time means a hell of a lot.

What sort of things do wish to impact those consulting days you think you might repair that and knowing what you know now.

We could be here forever well one when things are going good aspect for the bottom to fall out because here’s the thing that bothered me about all the marketing books and advice and there were maybe a couple people were telling me but but at some point Klein is going to feel that you’re not doing anything for them they’re paying you. No matter how much money you’re making. So I had a client and this was right when I quit. That’s the reason why I got out of consulting and went into investing. When they came on with me they just had started their store. They don’t have any employees no inventory no sales. So I started with them from the very beginning

and got to a point where they were selling out of all of their inventory. They ended up on the $80000 and they told me well you’re only putting together the marketing component. I don’t want to give you the 80 to get your own. And I said how could you not want to pay me and before I bought the building I bought the inventory but I had no customers. None. And that was the kind of thing where I mean it was my fault because I probably should have got all the money upfront and not allow payments to happen. So it’s one of those things we’re hindsight is 20 20 and I really just got tired of being in a situation like that where a client would end up being ship and you see in an ad agency world as

well. Like it would do incredibly well for big brand. And after four years they would just change the agency to go with us for no reason at all for no reason.

So yeah it happens a lot. And I think you know that’s it’s kind of a self-fulfilling prophecy because when I got into this as well and I do consulting now when I see you know when I watch those Holbert videos from back in the day in the early county ones and I sort of heard all the stuff that they had to say about these kind of situations.

And then you go through it yourself and I don’t know if or just don’t you don’t take it seriously or are you going to see for yourself for it.

Yeah I was like how were these just the all grim result. And he doesn’t know. Well I think it’s unlikely that he was right all along.

It’s funny because you almost have to like prove to yourself why one of these huge deals that were people a over and you’re like he was right you know or whoever you know it’s funny how it works that way with psychologists. But you yourself see it first and that really is the experience of course.

But what’s so much better than that. Yeah.

And one of the people yeah and I was younger and a little probably too arrogant at the time a little bit naive but that’s one of the lessons inside OK what you have to protect the money. And it wasn’t like I could afford not to have 80000. Not only was I upset financially but I was also heartbroken because I liked the person who ran the company. But I see why Kevin O’Leary and Dan Halbert as they got older they became so harsh because they had been screwed over so many times and they’re so blunt and in their dealings. So that’s one mistake that I wish that I could do over again. And then probably not putting

myself out there more earlier. And I think we all want to be great before we present ourselves to the world but at a certain point I think you’re just plain and let in the fear and your mind overcoming So working through whatever subconscious issues that we have and seeing the people that are out there now going back to write my cry and it’s just absolutely fearless like Gary Vaynerchuk fearless garden fearless so I’m really trying to just put myself out there more and get better everyday.

That’s awesome. That’s awesome. Love brings us up to where we’re at. I mean you decided to leave the marketing consulting world and decide to get something different.


Tell us about that process where you were sort of at the end of that phase and you are going to begin a new phase and sort of the thinking that went all that you know is perfect time and so I had a college buddy who called me and we both went to Indiana University together and a guy that he went to who we got his MBA with called him and said I have to get you guys on the phone to tell you something. So this was right after the recession. So he picked up city at I think a dollar 10 and previously I think city was like a five hundred bucks. Well I was like OK great. You know the whole stack thing I’ve heard of it. My dad had lost a ton of money in 2000 so my appetite was turned off too. And that’s when at that time

and then like four or five months later he called us back and he was like yeah I’m about to exit my position at seven dollars and I’m like What do you mean. And he was like remember what I bought it at a dollar and some change of say yeah sounds good now. Now seven bucks and I’m like oh geez. Are you serious. Got to let the fire. My other friend had already been investing. So he said I want to show you what I know. Because the guy who taught me told me to pass it on. So on. And at the time I mean I was getting fed up with the market in a tricky toad like I was good at marketing. I don’t know for some corporations but I knew I couldn’t be the best at it. So there’s a small niche

that I could be a part of. And there are so many marketers now. I couldn’t find a lane to to stand out and so we have to for a few sessions for about three weeks in a row and every day I’m telling you like a kid who’s playing Call of Duty I was around 30 hours a day and I felt like I finally found my passion because all marketers know what’s hot. We know trends very well and when you’re looking at the stock market and you’re looking at a graph you’re doing nothing more than looking at data. So if you are as are underperforming they’re going to go down. Well they’re going to go out. So I saw the parallels in the market and I just went all in and I asked him I said well if I

wanted to make more money per day what would I do. And he said just buy more contracts in a futures market or buy more shares. And I said well how much of my limited to he said as much as you can afford. And I said Oh and guess what. Eureka and the great part is like I don’t even know. I told the guy yesterday I said he said I don’t know if I’m going to work with you. I said well you work with me or not does not determine what I make. I’m completely fine with that come on when you’re ready. But I love the fact that if I do well in the market like a trader the German DAX which is their index today. OK. I was in and out of the market for two hours nice day. Thirty five hundred. And I’m really

happy because I didn’t have to negotiate with anyone to write right on money but going through that journey again and learning and apply myself and taken all the tools that I learned about discipline from marketing I’m just applied in here to a different skill set.

Right. Just basically when he told you about this you just got very excited about it.

Much like you probably did when you first step to move the room there the Kennedys.

The same feeling same feeling and autonomy.

Like you said you don’t have to negotiate with any person and so forth must be a draw to have the autonomy to just work on your own or your own leisure and or at your own frenetic pace.

So it’s very true you look at the market everyday because I think a lot of people saying in investing they give this illusion that you can sit on a yacht and make ninety seven thousand dollars in two minutes. And those are the people that are not making any money. They’re making all their money off of you know students who people buy subscriptions. So are you keeping the same discipline because in any industry the people at the top are working consistently. So I look at the market every day because I’m studying because what people are realize is that the charts that you see are representative of millions of people buying and selling. Right. So you have to study the patterns over and over again. But

I do love the autonomy deliberation and then taking something that most people think is such a difficult thing going through the process of learning of how to get in and get out of the market. And I think one of the biggest mistakes we were talking before we began recording no one tells entrepreneurs Hey I know that you’re going to be hustling and grinding away but you need some money to work for you. So in case things do not go well in your business. God forbid you will still have a nest egg there. I think one of the most important lessons there’s a Tony Robbins book money master the game is the one that I recommend the most. I don’t have any affiliation but that book has made me more money than

any other. Every entrepreneur has to be invested into the market. Man I know we can make a certain amount from our actual business sense but let the other wealthy people do follow their trend. Look at the S&P 500. And then also invest long term.

You know you’re talking off the air before we started. So it’s one of the things that people get into trouble sometimes people go back to look at the episode I did with just a goss most recently at the time of this recording he talks about how he was doing consulting him freelance copywriting and you could call that the three days I and heal.

He lost his biggest consulting client which was like 90 percent of his income while his girlfriend dumped them and then LeBron James left Cleveland for Madison on all three of the three big ones but you know 90 percent of your income out of the window. I mean that can happen if you don’t have a diversification and multiple income streams. And that’s why I think it’s important to have you on today. So you know I’m a complete moron when it comes to this stuff. What should I know. You know right off the bat about investing.

OK. First thing first don’t worry about the market crashing because everyone always asks me what are you going to do if the market tanks. And the short answer is there are many crashes that happen almost every year so like October 24th August 24th was a flash crash that happened in Japan and then spilled over here getting word of last year the market was down for 30 days straight Breck’s June 24th and then after the election. Trump you know the market went down and up and overall if you look at any chart I tell every entrepreneur you can see train because it’s what you do for a living. Especially marketers look at a five year month and just start with the basics. Look

at the Dow the S&P 500. Look at the Nasdaq. So the Nasdaq and indexes nothing more look at it like an all star team. So it’s the 30 best companies for the Dow the 500 best on the S&P. So you don’t have to pick a particular company to do well just go with the all star team. You may not be a great GM to pick the best player but if I tell you to put money on the West and All-Star team every year are the same concept so the Dow the S&P and the Nasdaq are the three biggest indexes that there is in our market. Just start there and then Vanguard has some very low cost ones so even like IWM which is a ticker symbol which is the Russell 1000

a smaller index is only around like $135 per share and I said do the minimum and just do 250 a month every month because my dad didn’t know so when I told him that you know if he would have put 250 in per month and if you would get 7 percent interest every year which is a very small amount it’s average by the time I turned 30 I would have 321 thousand dollars. My 30th birthday he said I could have taken half of that money and just put it away because technically I gave it to you that’s it. I still would have been adding 100 plus Grant sitting there for me. So if you guys have or Ogowe it listen to the podcast. If you have kids at least start for your

children. So when they get to be of age because I’m very terrified after the next recession. And then with robotics and AI coming into play I don’t think we’re going to have a sustainable job market in 2025. I’m going to be very doggy dog so so already mentioned money master the game. That’s a good book. And then I put out a video every day this let this shorter than seven minutes every day. If you guys want some more information there. But if you’re not invested in the market I would personally tell you. Just get into an index fund. Ride it up. And even after the recession the market went up 300 percent. And the Trump bump that happened is just an extension of what happened when Obama was in office and we

probably could get a 400 percent return off of bottom. But most entrepreneurs are not in the market and is only so much hustling and grinding that you can do to make your business work for you.

Absolutely. That’s great. Thanks a lot man.

You’ve dropped a lot of knowledge here today it’s good to hear you know your sort of career trajectory of your story and it’s been fascinating talking with you. I really want to thank you for coming on the show.

Thank you. I appreciate it so much. I had a blast. Awesome for everybody else listening to the show. That’s a wrap for another edition of the podcast.

We’ll be back again next week with somebody else who’s just as excitable and interesting and as fun as you and hopefully and told them.

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