How To Become A Professional Freelancer – Interview With Andy Strote

I got to interview Andy Strote lately about his journey building a successful freelancing and then agency career.

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09/23/2023 04:39 am GMT

Interview Transcript:

Andy, what is the difference between a professional freelancer and an amateur? 

 thanks for the question. a professional freelancer is, someone who’s, accomplished at their craft to start with. I see a lot of people want to be freelancers.

it’s been, uh, what everybody’s been talking about. Work for yourself, be a freelancer. but I think you need to be very accomplished at your craft, knowing what you’re doing, no matter what you’re doing, whether you’re a writer, designer, filmmaker, or whatever. When you go into the freelance market, You’re up against everybody else.

and it’s not to say that you have to have the experience of somebody who’s been a freelancer for the last 10 years of course you don’t. but you have to be good enough at whatever level that you’re at to be able to compete, there, right? So that’s part of it. So know your craft, be comfortable and confident in what you’re doing.

the second part is, as a freelancer, of course, you’re running your own business. running your own business means, scheduling, timing, uh, understanding how to work with clients. Assuming you’re freelancing for clients and you’re not launching your own product. Say, people depend on you. People count on you.

If you say you’re gonna deliver a project by Wednesday at 10 o’clock, You better. it’s the number one thing that clients are looking for really is, reliability. you can’t let people down. you just absolutely have to be there. Otherwise you become too difficult to work with.

And so professional freelancers, they deliver on time. They deliver what they said they would deliver. It’s complete, it’s done. And whatever it takes, whether you have to work nights or weekends or whatever,and only agree to something that you know you can deliver. Sometimes you’ll get clients who pressure you into deadlines that.

You already know you can’t meet. You gotta say that at the beginning. don’t say yes when you really mean no. say no at the beginning. Negotiate something that works out. That might mean changing the time, changing the scope of the work, anything but you and the client have to agree so that when it comes time to deliver, you’re both happy.

You’re both satisfied. you’ve done what you said you would, and the client is happy that you’ve accomplished that. So to me, those are some of the main things. when you start freelancing,if you’re just getting into it, you’ll probably do all kinds of jobs for all kinds of people.

and simply because you’re finding your way, you need the work. You need the money, you need to build a portfolio, right? So some people now, when they get into it, they already know exactly what they wanna do. They wanna, because maybe past work or life experience, they know I wanna write or I wanna design for, health related companies say so.

So that’s fine if you already know that, but most freelancers I find, don’t, I didn’t. and no. and so you’ll take on anything as it comes to you to keep yourself busy, to build up your portfolio to some money, right? But as you get along, in a while, in a year or two, three, maybe you wanna start thinking about.

What you really like to do, what you’re comfortable doing, what you’re good at doing, hopefully something that you’ve already done. And then start maybe looking for clients in that same area. And in other words, what we’re talking about here is forming a niche. Don’t worry about it too soon. it’ll actually come to you.

You don’t have to go out looking for if you don’t know, if you don’t know off the top, some people right first thing, oh, what’s my niche gonna be? If that’s your question, don’t worry about it. it will come to you. I wish 

I would’ve watched this interview a few months ago ’cause that was such a hard process for me.

So I’m so glad you’re talking about it. Yeah. Don’t worry about it. it 

will find you, it will find you and in the strangest way, sometimes you’ll do a job for somebody. and you’ll maybe enjoy doing that job, then they’ll give you another job. And now you’ve done, now you’ve done two, right?

And then maybe there’s a third one, and it is now you’re getting comfortable with the subject matter, right? you, yeah. Understand it more. you’re, it’s easier for you. it’ll come a little quicker for you. and the next thing if you’re lucky, you get a client where you get steady work and you get one job after the other, and that, by the way, is the next thing you should be looking for.

You should be looking for steady clients. But anyways, once, once you get a number of jobs, say for the same client, you should start looking for similar clients because you start to understand that marketplace, right? you end up doing things that you wouldn’t think of until it comes to you.

So I talked to one freelance writer. She was all about building materials, Roofing, different window types, caulking, all that stuff. She knew nothing about that until she started working in that field. And then she decided she, she liked it. and now most of her business is around building materials.

So Cool. Who would’ve thunk it, but yeah. there she is. so that’s, that’s something to consider. 

 I love how much you talk about in your book, the personal side of building client relationships. You do such a beautiful job of describing that part.

and something you may not realize as a new freelancer as I am, is that if you can connect with clients personally, they, as you said, the number one thing that they want is somebody who’s reliable and. If you can build that bridge of trust then, and also be adaptable as you also talking about your, in your book and be willing to take on the challenge of providing different services to that same client.

It’s more, it’s about that personal relationship that you build and all of these other beautiful things come from it. And if you’re just human in your interactions with these people. I, you gave some beautiful examples in the book we can talk about later, but just treating it like a person to person interaction.

Yeah. And that really resonated with me and I think that’s a great lesson, especially for new freelancers is hey,just show up and be like, be your best as a human and as a professional and all these other amazing things will start to take care of themselves. 

Yeah. Yeah. So I talk about business friends, I.

make them your business friends. And so what’s the difference between say, a business friend and a regular personal friend? And I give a couple of examples, right? as a business friend, we probably haven’t been in each other’s homes, we haven’t visited each other, but we’ve had lunches together.

We’ve had coffees together, right? We might’ve even gone out together. I’ve bought clients tickets for things. Sometimes I’ve just given them the tickets that they can go themselves. Other times I say, would you like to come? I’ve got four tickets. Bring your husband, wife as the case may be, and if you like, we will have a night out.

And it’s on me. Some people don’t like that. They sure. Gimme the tickets. I don’t wanna go with you though. That’s fine. Right? The point is you establish a deeper relationship than just transactional business to business all the time. you, when you talk, if you talk to each other on the phone, which is a whole nother subject I can get into, seems a lot of people don’t like talking on the phone, but I think that’s a mistake.

you just establish a completely different level of trust, and to me, that’s what it takes if you want to get job after job. with no competition. Yeah. And that was always my goal. That was always my goal. I wanted to be, my clients go-to writer when they needed writing down the kind of writing that I did, they would just call me or send me an email, whatever.

I never competed, I never had to compete. I’m not,and we never bargain much over money either. Now, maybe you could say, gee, I should have raised my rights to the point where we were arguing over money. But it’s so much easier if you’re not. And and that, that leads to, a third thing.

And when we talked about amateur and professional earlier about an amateur and professional freelancer, there are also amateur and professional clients. Yes. and I want professional clients. So just by nature for me, and it wasn’t a hundred percent like this, but most of them were in larger companies.

Okay. it’s just the way it is. Larger companies have bigger budgets and they have more experienced people. They have professional marketing communications people. These people know how to run a job, how to run their business. You know how to work with people like me, how to work with freelancers.

they understand deadlines, they understand their obligations. When they start a job, they have to have a written brief. They have to give you background material. when they talk about deadlines, they understand that the deadline is reasonable. If there’s any back and forth, they’re willing to talk about it, Whereas amateurs, the first thing they want to talk about is money. How much is it gonna cost? Yeah. And you haven’t even defined the job. I don’t know. What are we talking about here, right? What do you mean how much is what gonna cost? and then they have no idea the process you go through to get to the final product.

So they wanna jump from the briefing to the finished product without the steps in between. So normally, for example, for copywriting, In many cases, you would do an outline for the client just to make sure before you write the whole thing, if it’s a, if it’s a longer piece, shorter piece, you don’t do that.

But for a longer piece you might go through it and say, okay, here’s how we’re gonna structure this. Okay. ’cause I’ve written, I’ve written the whole websites, a hundred page websites. I’ve written,I’ve written, 96 page brochures. So you are gonna go through an outline before you just do the whole thing, right?

and those kind of clients know that they understand that step and they’re, and they want to pay, they’re willing to pay for it. So you’re gonna have a meeting either online or in person, and go through it just to make sure we’re all on the same path here, right? that’s what you want.

you want as you start to work with clients, you wanna filter out the amateurs from the professionals to me. you just want professional clients. the other big difference is,with professional clients, it’s not personal money. Okay. Yeah. Amateur clients, for the most part, small businesses.

Now, before I say this, I know there are a lot of freelancers who like working with small businesses, that’s their Jam that’s where they’re comfortable with. and they may have either a local business or they have a niche that is made up of a bunch of small businesses.

Small businesses can be fine as long as they’re professional about it. so it’s not always those only big businesses. we had a client, for example, his whole company was four or five people, two of them. One was his wife, one was his son, and he had a couple of other people. He was very professional.

I loved him. I loved working with him. because, one of the signs was he had an annual marketing budget, right? and he would tell us what it is. He said, uh, this, this is how much I got my budget this year. Then it was up to us to figure out, okay, let’s make a laundry list of all the things we wanna accomplish, and let’s start putting dollar figures next to all of these things and see where we net out. and it might take a little, so we were comfortable enough with each other to have that conversation. All right. And 

again, you’re sitting side by side with him as a partner, as a friend, as a business friend.


exactly. and figuring out sometimes how to optimize a budget that, in real life been, should have been bigger. But it’s not right. This is what he is got now. We have to make a really big impact with that money. How are we gonna do it? and let’s go through this and figure this thing out, right?

and so a small business, a relationship with a small business can be like that. and if you have that, then it’s fine, right? and then you make sure that the jobs you do are appropriate, that you’re getting paid appropriately for them. We charged him the same as we charged our biggest clients.

There was no difference. We didn’t have a special small business, right? There’s no need to, right? if you’re competent in what you’re doing, the writing, the designing, whatever, programming, then you should be able to do that at whatever your rates are. for all of your clients. I don’t believe in having, varying.

Now you can, sometimes there’s some, a little bit of back and forth, but, we don’t have, here’s the rate level A and rate level B and C. we never did that. but anyways, most of the clients that we worked with were bigger corporations and organizations. and when I started working freelance for some of them, back then, it was maybe a little bit easier to get in.

I remember, the biggest client, the one that we went for years and years through, through my freelancing, through my first agency, through my second agency, same client. I got in there just on a personal recommendation. There was no big vetting process. and I, and it was, They weren’t happy with the writer they had, and so now they’re gonna try me.

Okay? and so first job went well, so I got a second job and then I got a third job, and next thing they’re keeping me very busy. and that’s where we really established a good relationship. and then, the other thing that happens if you’re working freelance for a large company in their communications department, it might be so large that they have a number of internal clients.

So I, after a while, not at the beginning, but after a while, I started working for two or three different clients in that same com company, because each of those people within have different divisions. Right now, when you start working with one person, there. They’re not that anxious to share you because you are theirs.

And they don’t wanna share you because you might get too busy for them and they don’t want that. so it takes some time, but then eventually they’ll say, oh, their colleague over here, she just needs some help. Do you have time to help her? And of course you say, yeah, right? Yeah. and that, and now you’ve got two clients in the same company.

and that really helps. and then you see what happens after a few years, people come and go, they change jobs, right? So one of my clients in that first company, she left and went to work for the government and brought us in there. I still kept my old client. Yeah. Right now I got two big serious clients.

and then that’s why, that’s the other reason you wanna establish those kinds of business friends, relationships. People change jobs. Okay? If you’re lucky, you get to keep your old client because you already have a relationship with somebody else there, so that when the one person leaves, you don’t lose everything, which happens sometimes, but you gain, if you’re lucky, you gain a second client.

Now sometimes you have to jump through a hoop. They might have a pre-qualifying process or whatever. And, but if your relationship is strong enough and the person going there has a high enough position in that company, they can just bring you in on their say so. And we got into our biggest clients that way.

And it was all just personal relationships. and it was meeting at the right level, we did, I’ll tell you something else. and again, an individual freelancer wouldn’t be able to do this maybe, but if you have a small group of you, you can do this. we did with one client, we did this joint project where we contributed our work.

They contributed, it was a paper distributor. They contributed their paper and we hooked up with a printer. and the three of us, we created this publication. So we wrote it, we photographed it, we are directed at the whole thing. Free the printer, printed free. The paper guy contributed all the paper.

and now we each had something to show off and it was a real show piece and we entered it into awards shows and we won awards and everything then to launch it. And we did a number of issues, I don’t know, six or seven of them all together to launch each one. We’d have a party and each of us would invite our friends and business friends come, let’s, we’re gonna have a party, right?

it did cost some money, but, we could afford, it was fine. we got real clients through that. The printer invited some of his clients, some of his printing clients. We didn’t know, through that we were introduced to them, and formed a relationship. I, 

that reminds me of one of my favorite things I learned from the book is a strategy that you used, which again, is emphasizing this business friend, this relationship building thing that brings all these serendipitous things on the other side.

And that is the website cake. Can you tell us about the website cake? I love that idea so much. I definitely wanna borrow that at some point in my career somehow. It’s so beautiful. 

Do it. Just do it. Do it. if you build websites, so if you’re a developer, if you’re a writer and you’re involved in a website and so on, it’s some, on some.

That website’s gonna launch, right? And,ideally you have a formal launch event, right? So many times in our, for us, the formal launch, we would go to the clients and meet, in a boardroom somewhere. and then, one of their, IT guys, would coordinate it and, push the magic button.

And here comes the new website, right? So you’re all in the room, you’re all waiting, and there’s, there are a bunch of people who’ve only seen bits and pieces of it, or they haven’t seen any of it or whatever, but you’re all standing there, right? So we thought, this is an occasion for at least a little bit of a party.

we got,the homepage of the website. you can go to a baker and get them to make out of icing. Any kind of graphic or any picture trans transferred onto icing. so we got like a big. Sheet cake, like a rectangular cake that you could cut, 30 or 40 pieces out of. And the top of it was the homepage of the website.

so cool. Yeah. So when we come there, we would bring it as a surprise. We wouldn’t, we would unveil it the minute they pushed the button at the website went up, live on the big screen, open the box, there’s the cake, somebody get the coffee. Here we go. And often you get the c e O walking in, the president, walking in ’cause they wanna see the new website.

Yeah. And the first thing you do is you hand ’em a piece of cake. and next thing you’re talking to the c o At least they know who you are. I, these are the guys, 

I love that so much. It almost brings a tear to my eye. It’s such a magical human experience. And yeah.

There’s so many examples in your book and your lessons that you’re sharing with people about just taking. The time to build that real relationship. And that’s such a cool idea. I love that 

so much. Yeah. Like even, one of, one of my clients, she went to a job and they were in the suburbs in a building and they had office coffee there.

So the first couple times I went to meetings, she’d say, oh, would you like a coffee? And I’d say, sure. And it was horrible. It was just the worst coffee. It was the worst coffee ever. We both knew it, But that was what they had. But from then on, I brought coffee to the meetings. I knew how she liked her coffee.

So there was a good coffee shop on my way. I just stop, pick up a couple of coffees, Bring ’em to the meeting. It just makes the meeting. 2% nicer. Yeah. You know that. That’s it. Here’s here, I brought you a coffee. Got one for myself. Okay, let’s talk. It’s just so much nicer. it’s nothing.

It’s nothing but it, it’s everything and 

it really helps with you becoming their go-to person because you’re a copywriter, but you built an agency to be able to Yeah. Handle other types of things. You got into all sorts of marketing,internet marketing, design, a lot of visual arts.

you basically became their go-to person, not just for writing, but for everything related to marketing. And because that personal tie was so strong, then all these other things were allowed to flourish 

when I started the agency, I had been freelancing as a writer and, I worked with some designers sometimes, some of my clients would say, oh, do you have a designer you work with?

we need a designer on this project. I would say, sure. I also had people, that I knew that I could work with on different types of projects. but then what would happen, and this is one of the things that sparked the idea, I should form an agency here. I would bring in a designer and I didn’t, I didn’t wanna get into, you owe me a percentage of this for bringing into the job.

I didn’t do any of those things. I just brought them in on good faith. you do your part of the work, we’ll work together, we’ll make this thing, whatever it might be, and hopefully we keep the client happy and away we go. But then I realized sometimes too, the designer, his part of the job is worth way more than mine.

Like way more, right? I just brought somebody in for a $20,000 job. I’m building seven. And I think all. I don’t wanna go to ’em and say, I want a piece of that. But, I thought, if I had a partner and we formed a company and we divided all the money up more or less equally, then we’d each get a piece of it.

And I remember when I formed my first agency, and so I went looking for a designer and I advertised and I found when I had 30 people respond to the ad. I met with five of ’em and eventually I chose one. We did a few projects together and decided we liked working together and let’s give this a go.

And I remember we went together to my accountant. Who I loved. he was the best accountant. and I, and we just talked about different things and I wanted to introduce my, my new partner to the account and see if he liked him. everybody’s cool. but one of the things I said, how do we go about sharing the money?

Like sometimes, a designer or somebody could bring in a, their part of the job is worth way more than my part. And he had really simple advice. he just said, you just share it. 50 50, 1 day one of you is gonna bring in a bigger job and the next day is the other guy. do not split nickel and dimes here.

just decide you’re gonna be 50 50 partners and get on with it. And to me that was really simple, but really good advice. and that, that did us well, in doing that. 

Yeah. I’ve got some questions here I wanted to ask you. Go for it. And I have a, I have an interesting story I wanna bring up as well, but let’s, dig back into the freelancing thing and Yeah.

what lesson in freelancing took you way too long to learn? 

what I just described to you that,that I could and should do more than just the writing and find somebody and however I wanted that relationship to be. I talk about in the book about forming virtual agencies, right?

So if you’re a writer, Find yourself a designer to work with. Find yourself a front end developer and whatever else you need. Depending on what kind of work you’re doing, you may wanna find a photographer. If it’s a, if it’s a company that has a lot of products and need a lot of product shots, that’d be great.

If you found a photographer with a little studio, you, or you could do product shots and so you could offer the whole thing. as a freelancer, the bigger the problem is that you’re solving the better, right? the more you can take off your client’s hands. 

Yes. The better. That’s a lesson I’m learning a lot right now is 

Right, because if you don’t, let’s say if you’re just a writer, now the client has to find a designer.

Now they have to pair you together ’cause they want you to work together. Oh. We need a front end developer. Ah, now the client has to find one of those too, right? and hope that we all can work together. Then the client is gonna get three invoices or whatever, and, or three estimates, first of all, then three invoices and blah, blah.

It’s just work. it’s just administrative work that you could do, right? And so what we did when, in a virtual agency is whoever’s got the project, they lead the project, they’re the interface with the client. So if it’s my client and I’m bringing in a designer and I’m bringing in a front end developer, I’m the one who talks to the client, I handle everything else behind the scenes to take it outta the client’s hands so they don’t have to worry about it.

And when we come back with the whole solution. That took me too long to learn.

Luckily, I’ve had some good teachers and I have your book, to help me learn things like that much faster. I lost, just for context, I’m currently just working on Upwork, which is like a whole other kind of game. yep. And I lost one of my first potential clients that seemed very excited to work with me because he was like, do you, do, and I do YouTube, consulting, which is something I had no intention to do it, just like you said.

I started trying different stuff and I ended up in this YouTube niche and I really like it. But at the time I was like, I’m not an editor and I don’t make thumbnails. you wanna get a designer to do that, and you want get an editor. I’m just a marketing guy. Yeah. And this one person was like trying to start a startup, he just needed somebody to.

To handle this thing. And he said, do you do thumbnails? And I said, no, not really. just because of a lack of confidence. And he said, do you do editing? And I said, no. and he said, honestly, I need somebody who can do it all. And I was like, Yeah. Okay. 

So especially if you want to work for startups or for smaller clients, but act, but actually, even for bigger clients, the more you can take on.

And so figure it out. if you’re gonna be doing that kind of YouTube consulting and you’re gonna be, you’re gonna need somebody who has these skills that might be two or three people, pull your team together, have meetings, have, do it over Zoom or however, if they’re local, go to a coffee shop, figure out how you could work together, because then they can bring you into their jobs.

you could be a resource for them, and that’s how it should work, right? So that you see yourselves as a team when needed. They’re gonna be projects where you don’t need the other people and they don’t need you. And that’s fine, right? You do it on your own and that’s great, but don’t do things that you’re not good at, right?

if you’re a lousy designer Don’t be the one doing the thumbnails, right? Yeah. find an experienced designer who’s got a portfolio of a hundred great thumbnails and think, wow, I want this guy on my team. Because that’s what clients react to. They see that and think, wow.

So you need that. You need that for yourself. so find the right people. to do that and have a decent team and how, however, formal, informal, you wanna keep it. So if you wanna keep it a virtual agency where you’re all independent, figure out how you’re gonna pay each other and all that.

it’s not that hard. Or do what I did and form a company, with another guy and the next thing you know, you’re hiring employees and the next thing you know, you started with two guys and now you got 30 people here. however you wanna do it. Yeah. 

that actually brings me to the personal story.

I, I wanna bring up, because your book, as I was reading it, I was like, it’s,I’m really getting this strange sensation that I’ve read something similar. And it wasn’t about the subject matter, it was the tone. And the idea I got was that it was like a time warp because I got to live your whole career in just a few days.

Yeah. And the book that it reminded me of, I didn’t know you had a personal tie to, is Confessions of an Advertising Man by David Ogilvy. Ah. Which is a book that I read when I was , marketing director for a company. I got thrust into this role at 25 and yeah, and I was learning about copywriting and email marketing, all this stuff.

And I read Confessions of an Advertising Man and I remember thinking this sounds really cool. I could see a life where I build an advertising agency. Yeah. And I don’t know if it’s in the cards, at this point in my life and career, but by reading your book, I got to see what that might look like.

And I thought that was really cool. But I also heard on an interview that you have some personal connections with David Ogilvy. I wanted to hear you talk 

about that. I have two connections with David Ogilvy. the first and easiest one is his book, Ogilvy on Advertising. I should have brought it, it’s right there on a shelf.

It’s, I have an autographed copy of it. I met Sir David Ogilvy, when that book came out and he was doing a little promo tour, and I think he went to cities where he had, where they had offices. So Toronto has Ogilvy and Mayer, or I guess just called Ogilvy. so he came to Toronto, to visit the office and to pitch his book and signed copies.

And he gave a little talk, which was nice. And we all lined up and got our Stein copies. but the other, connection I have in my very first job. Walking into a little agency. Talked my way into it as a writer. Had no experience whatsoever. Didn’t go to school for it, just managed to talk my way into it.

got a job as a junior, junior, very junior copywriter. at one point they paired me with a senior designer, and so he was probably in his late sixties. By then. He had worked personally with David Ogilvy. Ogilvy opened an office in Toronto because in New York they had the Shell Oil business. And of course oil is big in Canada and Alberta.

And they were looking for some help in Canada. And they said to David Ogilvy, if you open a Canadian office, we’ll give you the business. And he said, okay. So he opened an office in Toronto and the art director I worked with, he was one of the first employees of the Toronto office of Ogilvy and David Ogilvy would come up to Toronto from New York and work on campaigns.

And so we got to talking about this and I’m just like thinking, oh my God, you’re kidding. you worked with David Oglevy serious. So he said, I’ll show you. Okay. I’ll bring in my, I’ll bring in a portfolio. So he brought in his portfolio with all these tear sheets, like newspaper ads, magazine ads and stuff like that.

And he’d say, yeah, David wrote that. David wrote that. Wow. That, you’ve gotta be kidding, right? Yeah. It was so great. it was such an experience, to live that. yeah. I don’t think this guy’s around anymore. it’s too bad. he was also, aside from being a good art, he was a very good art director and he had lots of experience.

He was just, he was a Scottish guy. I. He was just the most handsome guy. He was a male model in his sixties. if you wanted a debonair salt and pepper hair looking really good in a prince striped suit, he’s your man. So he was my art director, I was his child writer. yeah, it was fun. It was, yeah, it 

was great.

Yeah. And I think the common thread with all of these things is there seems to be something, maybe a natural talent that you have or had or whatever, that the human part of the this, connecting with other people seems to come easily to you and it, and I feel like that’s something that brought a lot of really amazing things in your career.

It was, yeah. I don’t know if this is just looking back, but when you tell the stories, now, you seem to have a general ease about you and the way that you think about business and life and, I heard another story that you. You took off young in life. You just went traveling, you lived in Germany, worked in a castle.

Yeah, that’s true. Yeah. I guess what drives that? What drives that like natural ability to connect with people? 

I’ll tell you the things I didn’t do and I actually regret some of it a little bit. Okay. not too heavily.

I never went to university. I finished high school. Interesting. And my parents weren’t that driven. They, you know, I know lots of people. They went to university, their mom and dad said, you’re going to university. Let’s go make sure you got the good marks and you’re going to University of Toronto or wherever you’re going, but you are going to school.

my parents didn’t say that, and I didn’t, and frankly, I had really no idea what I wanted to do. I never knew what I wanted as a career. If I sat for more than five minutes and thought about it, I might have figured it out. Because even the, even as a kid, I liked writing. I wrote,I wrote since I was like, I love school, like public school even.

I remember doing a big assignment in grade five on migration patterns of birds. I loved that. I loved doing the research and wrote my little project, whatever it was, and drew little maps and all that stuff. I loved that stuff. and then I should have also known in high school, a friend of mine who also was a copywriter later, we started our own newspaper that we wrote, produced.

So nearly got thrown outta school for it because the school had a newspaper. It was really boring. We wanted nothing to do with it. We wanted to talk about music, culture, whatever. Have funny cartoons and jokes. Make fun of the principal, that kind of stuff, right? they say, oh, why don’t you just join the school newspaper?

Are you kidding? Such a boring thing. So we sold our newspaper 10 cents, but we had to sell out in the street. They wouldn’t let us sell it on school property, so okay, fine, we’ll sell it in the street. and we sold out every edition, I don’t know, few hundred copies, and we wrote the whole thing and stapled it together, and had a little gestetner machine that we ran it off ourselves and that was it.

when I was finished high school, I had no idea. And yeah, my, my girlfriend at the time and I, ended up going to Germany. my, I’m, I was born in Germany. My parents were both German. my father knew somebody, a woman who ran this hotel, which was an old castle, had a turret and everything.

So he got us jobs there. So I brushed up on my German. I worked the front desk. I would answer the phone at this hotel, right? and then help guests when they came in. and to get to the rooms, you had to go up the turret. There were no elevators. there’s only, luckily there’s three stories, so that’s the highest you had to go carrying big, heavy suitcases with no roller wheels on them.

yeah, so I did that. And came back and I worked a bunch of odd jobs until I decided my friend had a copywriting job and he told me what copywriting was about, which I had no clue. I had zero clue. I can’t believe it in retrospect, really, how clueless I was and who knows, maybe still am. How, because I used to, read magazines and watch TV and stuff like that.

But I never thought about how did these ads get here? who makes these ads, right? I’ve talked to other copywriters who grew up in the business. Their father was a copywriter, so they knew all about the ins and outs of the business. I didn’t know any of that until my friend got a job and then we started talking about it.

I worked, A warehouse packing boxes at the time. And I thought, this, this can’t go on for too long. and what does a copywriter do? And so we talked about it and stuff, and I cobbled together a fake portfolio, obviously fake, wasn’t trying to fool anybody, just to show I could write something, right?

So I’d have like headlines and subheads and they’re all like little ads and stuff, right? And I managed to talk my way into this job, first job. So the regret, one hand, I wish I’d gone to university just for the experience. I’m not sure to learn what, in retrospect now, the things that I like to learn now.

they’re not things that would make you any money. I could have studied that in university. So the Italian Renaissance, for example. literature, that kind of stuff, which interests me a lot. But I didn’t, and here we are. but yeah, as far as, getting along with people, I don’t know.

I guess it’s just my nature. I don’t easily get intimidated by people. when we work with clients and the c e o walks into the room to see the launch of the new, oops, to see the launch of the new website. That’s fine. say hi. I got to get to know them. Then I ended up in, in further meetings with the CEO e he, they wanted to launch a whole new direction for something.

So he thought it was important enough for him to be there. That’s cool. I’ve worked with other CEOs, that’s fine. They’re just people. and I have some respect for who they’re and their job, and they’re your clients and, don’t be a smart ass,and understand why you’re there and what you’re doing, and you’re not there to be their buddy.

but you don’t have to, cower in a corner. 

I, again, see a common thread that maybe it wasn’t as evident to you as it was happening, this passion for writing, you have as a child, you start your first business while you’re still in grade school, and then you go out and get, worldly experience and you work in hospitality, interestingly enough.

Yeah. Yeah. So I can see where all these things end up blossoming over your career. Yeah. your interest in writing, your interest in people, your interest in, I guess stepping outside the lines of I. The school, you could have said, Hey, the school said we can’t do this, or we can’t do it.

But instead you were like, no, I wanna do it. And yeah. Yeah. It’s not against the law, it’s just they’re just saying they don’t want it, So that renegade kind of attitude, and I can see them all coming together into this creative agency idea and being a writer, a copywriter too.

a lot of writers have no interest in the business side of writing, but clearly from a very young age, you did. you thought, Hey, this is pretty, you prob you probably made more money than any other kid your age at that time, selling your creative work. So I can see a common thread throughout 


yeah. I don’t know, it just seemed logical. It just seemed easy to me. it wasn’t a struggle, Yeah. 

What was your favorite unexpected consequence from freelancing and building an agency? 

getting to work with a lot of great people.

great photographers, great illustrators, great art directors, designers, right? even as a writer, if I’m doing some writing, say for a website or an ad or whatever it might be, I’m in, in my head, I’m drawing a rough layout of, what it could be.

’cause I need to know where everything’s gonna fit, right? if this is the style guidelines. So we want a nice, big, bold headline, for example, and the subheads are like this and the copy’s like that. I try to write it that way. I wanna, I used to joke, I say rip to fit, right?

You want whatever, I’m not gonna write you a 12 word headline. We want a five word headline, please. Okay. so that’s what we do. but then when I see a good designer actually do that, it’s way better than my scribble. Way better. and to me, it’s always a marvel. I still marvel at it.

You still look at it and think, wow, that’s really nice. that, that’s just perfect. and even then you get into little things, and some of these are nearly lost arts, but not yet, beautiful type setting. I’ve, I work, I got to work with some people. beautiful type setting.

they were still from the old school. I. Professional Typesetters. Now anybody with a Mac, anybody with the Adobe platform, you become your own type setter. I get it. and Adobe, supplies, fonts and the different font, foundries supply with fonts and, they’ve current them properly and everything, but they’re still tweaking that can be done, right?

And so these guys, these guys were like the Michelangelos of type man. Like beautiful. You don’t even know why it’s so beautiful when you look at it, right? You just look at it. ’cause they would do like custom books. They would do like art books and stuff and you open a page and there’d be a big, photograph or illustration on the left side.

And then the copy on the right side, you look at, you think, wow, this just sings right. And you think that’s what you want. I want those people working on my jobs, right? I hire those people because way beyond what any, what I could do. They’re just fanatical about it. And that’s what you want.

You, you want people who are fanatical about what it is they’re doing, so that working together, you bring something to the client. I think, wow. first of all, obviously underneath everything has to be a great idea, right? Whatever’s appropriate for the job that you’re doing, right? and sometimes they don’t have to be, it’s not some crazy, wacky, creative idea.

It has to be appropriate. So you could be working for an insurance company, you could be working for a bank, you could be working for an investment company. You could be working for, I don’t know, a utility, whatever, a not-for-profit. Each have different, ideas of what’s appropriate, right? You know what I mean?

you can’t do something crazy for a company that has a different tone of voice. It has to be, it has to fit right. But even within that, It could be the best possible execution of that for their audience, for their other stakeholders. Why not make it as nice as possible. Make it,execute really well.

Take care of everything. look at how everything works together. And so forming an agency and even before that, working freelance with some good people. That was always a joy. I love that. just makes, if you’re a copywriter, it just makes your copy so much better. Your copy is already three times better than it was if you just printed it out on eight and a half by 11.

I definitely aspire to enjoy the journey as much as you seem to have. yeah. And I think that’s important, having cool people around you enjoying what you’re doing, Yeah. Digging deeper into the craft and also being around other passionate people. yeah, 

see. That’s those all contribute.

Yeah. So that’s important too. Like the, there’s lots of cliches around that. you are the, some of the people around you and all of that, and some of the five, most important people around you. It’s all true. it really is. and I’ve had, some negative people around me before.

I get rid of ’em. I don’t wanna be with them. I really don’t. They just drag you down. Everything, some hangdog face and everything is a pain in the ass. And, complain about this, complain about that, and who has time for it? Forget it. I don’t know if you only have one life to live, but you certainly have this life to live, right?

so be with people who are uplifting, who bring you up, who contribute something to it, right? who, who help you and you’re happy helping them. that’s where you wanna be. 

I love that. And on that note of reflecting back on perhaps the meaning of life, at least within the context of professional life, if you had five minutes to travel back in time and whisper something into past Andy’s ear Yeah.

When you were just getting started, what would you say? Yeah.

first of all, say how lucky you are to be here, but,yeah, just absorb, I think I did a reasonable job, but maybe could have done better. Just absorb knowledge from the people around you. we used to, we had a, a phrase we used often in our agency is stand on the shoulders of giants, right? So there are people ahead of you, people who have many more years of experience and expertise, learn from them and then stand on their shoulders, right?

make a point of finding those people. There are lots of people, out there who are. if you’re a developer and you’re just starting out, say there are people who’ve been doing development work for 15, 20 years, right? they’ve seen, they’ve solved so many problems. They’ve seen everything.

They’ve seen the iterations of platforms and the iterations of, sites and so on. learn from them. it’s a real shortcut. It’s a, you don’t need to learn every last little thing yourself. and that’s something I think you can purposefully go out of your way to do.

You, you can decide. That is one of the key ways that you’re gonna learn from other people. And you can learn from books, you can learn from websites. You can learn watching YouTube. You can learn by going to school lots of ways, but you can also learn from the people around you or the people that you seek out.

See that’s the beauty these days of, you and I are talking here, right? Like years ago this would never be possible. we could never run into each other. We just couldn’t. Yeah, It wouldn’t happen. Yeah. But here you can, if you go online on, on Twitter, on LinkedIn, whatever the platform is, you can approach people, most people will respond, right?

as long as you do it in a reasonable, respectful way, right? So you can find people who are years ahead of you. Now you need to be a little bit appropriate about that too. I get people, DMing me about writing and so on. and I’m happy to help any time, right?

So I’ve had lots of conversations with people and I try to help them answer their questions and so on. But I also get people who. they just haven’t done their part of it. They just haven’t, they unfortunately read all these things, how to be a six figure copywriter in six months, right?

and they want me to answer that question. There’s no answer for that question. and do yourself a favor. Don’t buy that guy’s 500 course it ain’t gonna do it, right? you barely know how to string together a sentence. you’re not gonna be a six figure copywriter in six months. Not gonna happen, right?

if you want to approach somebody, if you want to learn from somebody online, have your own act together, and then when you approach them, it’s a reasonable approach. it makes sense and then most people are willing to help you. 

that was a really beautiful answer and.

I think that by writing your book and being willing to come on my podcast, you are one of the giants on whose shoulders I can stand at least a little bit taller. So thank you so much for writing your book. I want to talk about your book a little bit,to let people know my thoughts on it that I think is a beautiful gift to the world.

I think I’m really glad you put it together. like I said, I felt like it was a time warp because I got to live your whole career in just a few days and being somebody who has never really, I never really strove to be a professional, freelancer or anything, but. I got to learn very quickly, not only the tactical things, like what is a retainer?

I hear that word a lot and I got to learn, how, what is, what does that mean? What, how does it work? And some of the expectations of working with clients long term of the kinds of pitfalls to watch out for. So there’s a lot of practical wisdom, knowledge, and tips in there. But there’s also the experiential stuff.

The sometimes my favorite parts were just one little sentence you would say that was like, a certain way to think about dealing with people or clients or your own business or employees. You just say something briefly that I knew was decades of wisdom being compressed into that sentence. thank you.

let’s talk a little bit about your book before we end the call. And what’s it called and where can people find it? 

Hey, there it is. We have a copy of it right here. it’s called How to Start a Successful Creative Agency. it’s the Essential Business Guide for graphic designers, copywriters, filmmakers, photographers, and programmers.

I, I wanna emphasize it is a business guide. So I’m not gonna teach you how to be a copywriter. I’m not gonna teach you how to be a designer or any of that. It’s all about how to run, how to start up and run the business, and what I think is important in the business. you can find it,online, Amazon,a bunch of places, and any online,bookseller will, will have it.

It’s also on Gum Road. If you want A P D F version of it. It’s available there. in, in, in paperback on Amazon. Amazon’s the only place you can get it in paperback. it’s an amazing service. They have. they also have a Kindle version, so if you like reading on the Kindle, there’s that. yeah,that’s about it.

It’s 320 pages, 23 chapters. 

 I would like to say too, that I don’t really consider myself necessarily, like I didn’t resonate as much with the creative part. And I’m not a designer, I’m a marketer. And I realized after, reading the book, that’s also very creative and I got a lot of value out of it not being, maybe not being one of the groups that you called out on the cover anyways.

there was just so much to learn about business and about. Freelancing about the, the different paths you can choose, to grow your business and your career over time. Yeah. And a lot of other really wonderful lessons. 

yeah. I’m pretty happy with it. and it sells well, continues to sell.

so I’m happy about that. and I know even for myself, when I had the agencies I then had, long before I wrote this, I had employees who left and started their own agencies, and I was happy about that. and I still talk to them, some of them, and their agencies are still running, which I’m also happy about.

one guy started an agency in Europe. Great. Now, other guy on Canada’s East coast in Halifax. Perfect. they, they learned, I guess from us, from work working with us. They were employees. And, that’s the other thing I talk about here. if you wanna be a freelancer or if you wanna start your own agency, and if you have, you get jobs, say in, in other agencies, but before you go out on your own, one of the things you should be doing, aside from the work that you’re supposed to be doing day to day, is really keeping a good eye on how this place runs what they do, right?

So learn how to open a job. Learn how to estimate a job. if you’re working, there’s right, you’re probably gonna see, you’re gonna see stuff, you’re gonna see estimates, right? Get ahold of one and read one. Study it. what’s in the estimate? How’s this estimate broken down? You can probably, without any trouble.

maybe ask one of the principals, they’ll be happy to take you through it, right? if you’re, if you wanna learn this,they’ll teach you. Take the time to learn. Un understand. even the really mundane things, file systems. how do you manage your files? How do you manage like the files for your Adobe programs and everything else?

Do you have ’em on servers? Do you have them on the cloud? What do you use? What programs, what platforms, what do you use for accounting software? Because when you start your own, you’re gonna have to know all that stuff. You’re gonna have to have something, right? You’re gonna have to figure out how you’re gonna do it.

You might not do it exactly the way the agency did it, and if you get two or three agency jobs, even better because then you can compare because each agency will run differently, right? You’ll see different operating styles, you’ll see different ways they do things. Keep your eyes and ears open.

That’s a free, that’s a free education to me, that’s your education right there, right? Aside from the education you’re getting, practicing your craft, so you know, if you’re lucky as a writer coming up, if you’re really fortunate, there’ll be a senior writer there who’s more experienced than you, who will work with you, who will make your writing better, learn the writing part from them, improve your writing as you go, but also see how the whole place runs.

look at the role. Look the creative director. How does the creative director work? With the studio, like how do they do that? Because it’s different. They have different ways of doing it. Figure it out. Because if you start your own agency, you might be the creative director. How are you gonna work?

even if you’re working with other people,in a virtual agency, you’re gonna have to work with other people. How are you gonna do that? I love that, that’s what you can learn. 

It all goes back to the lesson that you mentioned earlier of just always paying attention to your surroundings and trying to learn from other people around you and your situation.

Yeah. And I think that’s a recipe for a successful and happy career and life. Yeah. Yeah. Andy, other than picking up your book, where would you like people to find you online? 

on Twitter? It’s @strotebook, so SS t r o t e b o K, one word stro book. the website is creative agency book.com. if you go to the website, go to the blog, there are over a hundred posts there.

All of it, practical information, a lot of it based on what’s in the book, some of it newer stuff that’s not in the book. I try to write about things that I think will really help people that you can pick something up from and think, maybe I can apply this. So it’s all there on the blog. whether or not you buy the book, you can go read these blog posts and see if they help you.

yeah, that’s it. Creative agency book.com. That’s where you’ll find all that. And I 

would. Say also just being a follower of yours on Twitter, there are lots of lessons to learn. Your tweets are lots of great lessons there that some come from the book, some not, But yeah. Wonderful. Thank you so much Andy, for coming on the show and I look forward to continuing to learn from you.

Thank you very much for asking me, and I look forward to hearing from you as you launch your business. 

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