About this podcast episode…

FREELANCE DESIGNER BRENNAN GILBERT

Meet Brennan Gilbert, a seasoned designer based in Colorado - who after years of freelancing on the side went full time freelance in January 2023.

Multiple roles in agencies and tech startups gave him a tonne of knowledge in marketing, sales and processes that are paying off now. Brennan discusses the importance of time management, client expectations, and the intricacies of various business models, including subscription-based pricing. Yep, ‘subscription’ instead of ‘retainer’ - we dig deep into that one.

A self professed geek, Brennan’s leaning into the business as much as the design. Not many freelancers create an ‘annual report’, or have frequent ‘Straturdays’ to strategise at the weekend. But, maybe we should? See/hear what you think.

Read a full transcript & get Links in the tabs.

More from BRENNAN GILBERT

Brennan’s website
Brennan on LinkedIn
Brennan on Instagram

More from Steve Folland

Steve on Instagram
Steve’s freelance site
Being Freelance Community
Steve’s course for new freelancers
The Doing It For The Kids podcast

Transcript of the Being Freelance podcast with Steve Folland and Freelance Brand Designer Brennan Gilbert

Steve Folland: We're off to Denver, Colorado to chat to freelance brand designer, Brennan Gilbert.

Brennan Gilbert: Hello! Thanks for having me.

Steve Folland: Thanks so much for doing this. Okay, Brennan, as ever, how about we get started hearing how you got started being freelance?

Brennan Gilbert: Honestly, my journey with freelance is both long and short, right? So I actually started freelancing in probably technically high school and college but they were odd jobs, right? The way a lot of people get started. It was wedding invites and business cards for friends and family. I think I sold a logo for a hundred dollars at the time.

And so college I majored in graphic design and I just fell in love with it. I absolutely loved it. I've been a designer ever since. And so back then I just thought it was so cool to, to create something and get paid for it. And especially as a kid who, I'm still a nerd, I was definitely more of a nerd back [00:01:00] then but I loved just making something on the computer and then getting paid for it.

And so my first few projects in college were actually just like for fun. There's a band called John Butler Trio. They were one of my all time favorites. And I had designed a poster for them. I just sent it to them. It was unsolicited and they, they said they already had someone working on it.

It's at a famous venue here in my state. It's called Red Rocks. Yeah. Beautiful venue, world famous, and the consolation prize was two free backstage passes to meet my all time favorite band at my all time favorite venue. And so zero dollars, but I was like, yes, I will, I will definitely take that. That is a great deal.

So yeah, I actually ended up doing a few gig posters for a few bands. And then for a while, it was kind of touch and go. I really, it really came down to my fulfillment at the day job, if that makes sense, [00:02:00] right? Like if I had a job that I loved, I didn't really do freelance. If I started to not feel fulfilled at the day job, I would do more freelance.

And so I started in the agency world and that was the that was a lot of hours. I was super busy. So very minimal freelance, wasn't doing a lot. I started at a small agency and then I went to a slightly bigger one at the bigger one. I started to you know, feel a little restless. And so I started to pick up freelance again, and this was back in the day where Dribble, the platform, was really big for designers. And I was on there. I was putting my stuff out there. And this CEO of some random upstart reached out and asked for product design. I had never done product design before, but it sounded cool. It was neat. And that turned into a seven year long full time job as their design director.

And it was because I hustled [00:03:00] at the beginning, I was working my day job at the agency from nine to five, and then I'd go home, I'd eat a microwave dinner, and then I would work from five until late into the evening, every single night. I did that for about six months, and it was because I was young and single, right?

I didn't have much else going on. But it was because of that hustle that, they're like, yeah, why don't you come on full time? And so I switched over from agencies into, that was the opening for me into the world of tech startups, which is something that I still primarily focus on in my industry these days.

But I was there for a few years, again, slowed down on freelance switched over to a different startup. And then that was the final inflection point. I think like a lot of people during the pandemic, I questioned everything. And it was really like, do I want to do this career? Do I want to do this specific job?

Is it life? Like, what is it? Why am I not feeling great? And I came to the conclusion that I still love design even after all [00:04:00] these years. And so January of last year, January 2023, I officially, even after doing it on the side for many, many years I went full time freelance as of January 2023. And I wish I had done it sooner.

It was a great leap. I'm grateful. For a very exciting year and a half. But yeah, that was, that was kind of the whole journey from start to finish.

Steve Folland: I tell you what, let's break, break this down into little bits then. How would you say you managed your time and your clients and their expectations and things when you would be doing a full day, you know, a full day at work and then coming back and and cracking on of an evening?

Brennan Gilbert: Yeah, I mean, good question. Again, that's why I joke about like I was young and single. I would not do that lifestyle now. And I don't recommend it for a lot of people. I think when you're young and hungry and you want to hustle. That's great. If that's what you want to do. And again, like I was freelancing, but it was truly just for this one client.

[00:05:00] And so it was long stints of dedicated time on singular projects. It was not like these days my busiest months I'll manage up to 12 clients at once. But back then that's how I balanced it was, there was a very clear line between my day job and my freelancing. And so it was kind of just like working two jobs, which may be for some people that feels like a lot, but compared to having 10, 12 clients that felt very manageable at the time. So yeah, way back then it was pretty easy to set expectations and hit deadlines and all that, because that was all I was focused on.

Steve Folland: When you then decided, start of last year, to go full time into freelancing, what was it that you had in place that gave you the confidence to do that by that point?

Brennan Gilbert: You know, my wife's in the other room, so she might overhear this, but her.

We've been together for seven years, which is awesome, but we got married October [00:06:00] 2022. And so it's no coincidence that I went full time freelance January 2023, having that safety net, having quite literal things like her health insurance through her job and being able to have that as a legally wedded couple, which we did not have before that, that made a huge difference. I mean, as much as I'm a design guy, I really am more analytical and business driven than I am design driven.

And so I, I took so long to make that switch because growing up, my parents were very big on no matter what you do, you got to pay your bills. And so I was never a hundred percent sure on taking that bet on myself. Yeah. I mean, the biggest inflection point for sure was getting married, having that safety net. And I worked, I worked really hard for that last quarter of 2022 too.

I had never done Webflow before, which is this web development platform that I work on. So I learned how to do that so I could sell [00:07:00] that as a service. So I could build out my new portfolio, so that I could start putting lines out to get clients. And so I set up a lot of stuff behind the scenes before I officially said, Hey, world, January, 2023... I think I even waited until February because I, I am like, if this doesn't go well, I'm just not going to tell anyone for a month.

But luckily it, it did go well. So yeah, safety net and preparation were key.

Steve Folland: Because your website, I mean, I love your website. It's is that what it looked like when you launched, if you see what I mean, if I look at it now?

Brennan Gilbert: No, I mean, the very first launch was certainly a bit different. I had, you know, I study a lot. I like to always be learning and looking at examples and seeing how other people do things. And so anytime I see something where it's like, wow, that's interesting I apply that. So the very first one I would say is a little closer to what you might see with junior design portfolios.

It [00:08:00] was like a sentence description and then nothing but pages of work, and that was it. And then I started to research, okay, well, let's actually think about this from a business perspective, from a sales and marketing perspective. And so I redesigned it to be more of a funnel, more of a landing page, right?

So a little bit more about me teasing stuff out, only featuring few key projects. And so it's only gone through maybe two iterations and they've been somewhat minor each time because the brand is pretty set for my own personal brand, but yeah, it's definitely an evolving thing. I mean, if I see something that I love tomorrow, I'll implement it this weekend.

That's probably one of my favorite parts about doing this yourself is no, one's going to tell you, 'no, don't spend your time on that'. If you want to change it, go ahead and change it.

Steve Folland: Brilliant. Did you do all of it yourself?

Brennan Gilbert: I did. I thought it'd be ironic if I had someone else build my site if I'm trying to sell that. So I built and designed the whole thing myself.

Steve Folland: Because I love the what is it? [00:09:00] "Building BAD things with good people". It's great - explain BAD?

Brennan Gilbert: Yeah. So I, I'm a big fan of puns. I love cheesy jokes. And frankly, the clients who want to work with me do too. It's a good barometer, right? But that tagline I was proud is building bad things with good people through Brand design, Art direction and Development. So it's kind of those three for BAD and I try to highlight that in my socials and stuff.

But yeah, it's cheesy, but people like it.

Steve Folland: I like it! You obviously spent quite a bit of time both agencies and, you know, with startups and you said that you, you know, your business driven, you, you like analyzing things, seeing how the business works, did spending that time in house help you figure out how to run a business?

Brennan Gilbert: Oh, for sure. I mean, I think about that all the time, and these days I'm doing a lot more mentorship. When I was in house, I led a team, [00:10:00] and so I was doing mentorship and management all in house, but these days, I, I seek that out. I, I like to help people because a lot of people help me along the way. And that's probably my biggest answer is I, I do think, especially in my industry and design, there are a lot of coaches and YouTube personalities and social media personas who say freelance is the only way it's all you can do.

You should for sure do it as soon as you can. And that might be true for some people, but it was not true for me. And it's not something I always readily recommend because. I think the grass is always greener, right? I think there's goods and bads to a lot of different things and you have to figure out what's good for you.

For me to be able to, it was kind of this trial by fire because agency life, that was, that was burnout culture. That was, we're going to work you on a project that you might not love until like you pass out, like we just [00:11:00] need the hours, right? And you're getting low pay and you have to work through the holidays.

But I learned so much from the people I worked with and I had a great team. I think that kind of culture is more insidious. If, if you don't like the people you're working with, I think if you're young and you're willing to do that with people you like, that's fine. But I learned so much in agency world.

Then if that wasn't. I switched over to startups, right? And for the last 15 years, this is starting to change now. But when startups first became big Facebook was famous for saying, move fast and break things, right? So it's all about speed. It's about efficiency. And I was the sole designer for most of the, the time that I was at these startups, my first startup for seven years, I went from contract, right?

Like I said to their first. In house design hire. It was just me for a number of years. Then I started to learn how to grow a team. And again, I started with freelancers, [00:12:00] then brought people on and at the biggest, it was, it was never huge, maybe a team of seven people, but I was overseeing both product design and brand design, working with the marketing team, working with the developers, and had I not gotten that firsthand experience, I don't know if I'd be able to scale the business as quickly as I was last year. I mean, I am proud to say that it was, it was a quick year to scale up to the goals that I wanted to. And again, it's because the iceberg metaphor, all of this. Was under the water for so many years. So that, you know, I, I put out an annual report last year and I try to, I don't want to bum people out, so I did not highlight the negatives too much, but I had a slide in there about it, but by and large, it tells the positive story of.

Yeah. Able to move fast, able to move quick, able to scale this business because, you know, you, you don't want to run people on social, but again, yeah, to answer your question, I would not have said that. seen that level of success, or even frankly, a [00:13:00] lot of the times where I do have a slow month now, I don't feel as stressed as I think I would if I didn't learn the business side of things.

And I think a lot of designers jump headfirst and are like, I can do this for myself. And they don't think about the 90 percent of other things behind the scenes.

Steve Folland: What would you say were the, the biggest things that you took away for it? You've implemented in your own business beyond, you know, working fast.

Brennan Gilbert: Sure. Truly, it's all the sales and marketing stuff. It's like that old movie The Karate Kid, where he's teaching him with the spun and he's like, why am I doing this? And it's like, oh, that actually is part of the whole thing. To sit quite literally, physically next to sales and marketing teams, even if at the time I complained about designing another PowerPoint deck, I learned how to Set up pitches and how to look for leads and set up funnels and seemingly basic things on the sales and marketing commercial side that they [00:14:00] take for granted, but there aren't a lot of folks on the design side because a lot of designers, I mean, designers joke all the time, right?

I don't like the business bits, right? Like I just like, I just want to create and it's like, that's all well and good. But when you're self employed. You, you do still have to pay your bills, right? You do still have to do this stuff. And so, yeah, truly the business side, all of these, these things like lead gen and customer funnels and projections and cashflow and margins I think those have been monumental.

I've never considered myself the best designer in the room, but I think the intersection of business savvy, customer satisfaction and design, okay, you might have a little competition.

Steve Folland: So it sounds like you kind of hit the floor running. Like, did you have clients lined up for, for when you. Went full time freelance.

Brennan Gilbert: I did. Now I will say I was a little overconfident in that because my first two [00:15:00] I attributed to like, I'm so good at this. I'm already getting clients. And it was just luck, right? It was just pure luck that they reached out. One was, Like a friend of a friend and the other we had worked together previously and she just happened to be starting a new business herself in January as well.

So it was two brand design clients. And then I did make the switch. I took my most recent startup and I said, I am sorry, I'm, I'm gonna leave the full time world, but I'm doing this exact same type of work as a freelancer, so they were my first official freelance client, was my former employer, and if you can set that up, right, because they have the need, you know they have the need, so, That was a solid move to be able to do that.

But yeah, I mean, for the first, the first four months were tough because I did have those clients, but then I didn't set up a business strategy right away. So I'm like, I was just basing it off of luck. And. That's not a repeatable process. [00:16:00] And so I had to hustle to try and find those first few clients.

But yeah, these days, like I said, I mean, it ranges anywhere from six clients to 12 planets per month is kind of how I think about it.

Steve Folland: So what would you say your business strategy is now?

Brennan Gilbert: Yeah. I mean, I've enjoyed listening to your podcast I've learned things that I'm like, okay, let me try that. And so just seeing what these other folks are doing, I'm trying to be more deliberate about spending time on the business itself. Right. And previously, even three months ago, I wasn't doing that.

I do social every once in a while, but I wasn't thoughtful about it. And so now I do really focus on Prospecting is probably the biggest part of the business, right? How do I just continually fill that funnel to make sure that there's always someone moving through at any one stage of the business? So cold outreach is definitely the toughest.

I would [00:17:00] say that that's a nut I'm still trying to crack, right? I don't have like a proven methodology for that. Truly reaching out and just sending an email to a stranger who has no references or any connection. I haven't heard a lot of panic on those ones, but trying to be more thoughtful about asking for referrals, asking for testimonials and, and just being very clear, not being afraid to be a little cringy, like, Hey, no, like my business is built on referrals.

Anyone you can point me to big or small, please do. And then social media LinkedIn has been my big focal point. And I feel like that's working out very well. I say this phrase a lot, but. Brick by brick and that's how I think about it. I am not expecting to go from a thousand followers to ten thousand in two weeks, right?

But if every single week I'm doing something with the business, that puts that network out there and then those people see it and then their friends see it. And [00:18:00] maybe if a thousand people see it and a hundred people click to my profile and ten reach out and one turns into a client. And so hopefully that'll scale it for time, but that's kind of my current thought is, is LinkedIn to just get a, an awareness and then outreach and referrals to try and land to the business

Steve Folland: And do you have local clients?

Brennan Gilbert: I do. Yeah, I have a whole range. They're all based in the States, but I have clients on the East coast. I have clients on the West coast and then. If they're in between one in Tennessee and then a few locally here in Colorado. I like meeting people in person. I like chatting with folks in person. I work with a restaurant group here in Colorado, and it's even after all these years, I'm still like that kid who gets excited to be like, well, I'll be walking with my wife, we'll see a restaurant.

And I'll be like, I, I designed that. She's like, I know you tell me every time. But. [00:19:00] I love it, right? It's still cool. So to have physical, tangible clients based here in Colorado, I hope to always work with at least a percentage that is based here in Denver.

Steve Folland: Do you go to like any actual in person networking events?

Brennan Gilbert: I do a lot of in person networking. Frankly, the online networking, I don't like. I feel like trying to figure out what to type is just terrible. These like online, like I love that conferences do free online versions, but again, they'll like, they'll have like a Public chat room. I was like, I'm not going to do that.

I, I, I did a well chat back in the day. That was plenty for me. I don't need to do that anymore. But the in person stuff, I'm big on it. Like I have to psyche myself up. I consider myself an extroverted introvert, but at my heart, like There are days where I don't want to talk to people. I don't get energized from that.

And I have to say, no, it's going to be worth it. You're going to meet at least one good person. That'll make it worth [00:20:00] it. And by the end, I always feel great about having gone to these in person events. But I'm not always excited when I first think about it. Because it is a lot, right? And there There are like people who just want to sell you stuff or like, they're just looking for what's in this for me and that, that isn't always great.

But yeah, anytime I can do in person I prefer that by far,

Steve Folland: Nice. You mentioned goals. So you're, you're quite a goal setter?

Brennan Gilbert: I'm very big on goal setting. And I think that's that mindset from startups, startups are so goal oriented. And again, when I was in house. Uh, you would catch me rolling my eyes every week, like, why are we doing this, what is this for, KPIs and OKRs, like, all this jargon, it's like, no one cares, and like, I was younger too, right, so it's like, I just, I just want to design, but I had the safety net of someone who would tell me what to do, and now that I'm doing it myself, it's like, okay, well KPIs aren't [00:21:00] really a bad idea.

Maybe we should do that. And so I'm not super strict about it. I definitely give myself the flexibility of it's not like I set up a year long's worth of goals. I really think about things in months and quarters. So financially. To avoid because I'm an overanalyzer. I do think about all of this a lot.

And I know if I tried to set up a financial goal for say every quarter, in addition to each month, I'd constantly be looking in that and trying to be like, okay, well, it's only 20 percent attainment. It should be 22%. So I do monthly for financial goals. Like, okay. Why are we good this month? Yes. Are we good next month?

Yes. Let's look at the third month. And then in terms of like, how do I work on the business? I try to do quarterly sort of goals, right? And they're squishy. It's kind of like last quarter I call them stratter days, right? Strategy Saturdays. And I sit down and I actually think about. What went [00:22:00] well this quarter?

What did not go so well and how can I improve? And it's very basic. You know, I never walk away with more than two or three goals at a time. And quite literally I try to make them, I forget the, the business. Jargon for it, but there's something smart goals. And I forget what the abbreviation is, but you, you want to make them measurable.

You want to make them achievable. You don't want to say, I want to year two. I want to make a million dollars. How, there is so much between this and that, but if I say for Q2, I want to increase my followers on LinkedIn by X percent, that's more manageable, right? That's, that's easier to figure out. So yeah in summary, goals every quarter and financial goals I evaluate I'd say every six weeks.

Steve Folland: Speaking of which, you, you said that you did your like your own annual report.

Brennan Gilbert: I did. And I'm big on that. I even joked when I posted it, it's like, we're still [00:23:00] businesses, you know, we're, we're one person businesses. And so and also from a marketing lead gen standpoint, brilliant idea. If for any designers listening or freelancers do an annual report build buzz make it look slick.

Right. And like, that was probably one of my best lead gen pieces of content that I've ever put out there. But It was a great process. It gave me a lot to sit back and evaluate and think about. It gave me a lot to reflect on. It helped me understand what was working and what wasn't. And it was a cool way to connect with the community and talk about these behind the scenes things that a lot of people don't talk about.

Like we were saying earlier, you know, what is, what is the true business side? Why are you doing this? Like, how do you think about literally structuring clients and. Payment models and all these little nitty gritty things where it's like, I love them. I have buddies who only post here's my latest logo, but it's [00:24:00] like, I know for me, it's very helpful to understand like, okay.

But like, like you say, go out and get brand clients, but like. How, like, how do I do that? And so that's what I try to speak to both in things like annual reports, or I'm trying to be more thoughtful about content on LinkedIn these days, but yeah, it was great. It was a fun project. It took a lot. I'm trying to evaluate every quarter now, so I don't have to do it all at once, but it was a cool one.

Steve Folland: I love the fact that it, it ended up being a, essentially a portfolio piece as well of you saying, Hey, I can make stuff like this, look like this. What was your key kind of thing that you took away from it? Like when you were reflecting back on that first year?

Brennan Gilbert: Uh, you know, probably the key takeaway is money is only ever going to be so motivating, right? And I say that with a background of I've been in DEI spaces. I acknowledge privilege and [00:25:00] equity versus equality, all that stuff. And to be able to say, Oh, don't focus on money. You have to be in a certain position to be able to say that I get that.

But once you hit that milestone of whatever those financial goals are, It's, it's a quick path to burnout and I think in year one, my goal was as simple as when I switched to freelance and working for myself, I want to make sure, like, my wife doesn't regret marrying a guy who can't help pay the bills, right?

And I joke, she's my ride or die, she's got me no matter what. But truly my only motivator was like, let me replace my salary from before. And that only lasted so long because there were a number of months and quarters where it's like, I was either stressed about not having any work at all, or I was stressed about, oh my gosh, I booked myself too full.

And it's because my only guidance was to Are you at this number that you should be at based off of your old salary? And so this year I'm trying to be a lot more thoughtful about, like, think about the [00:26:00] longterm, think about, I mean, theoretically, I'm, I'm like 36. I don't see how I could retire before the age of 65.

So it's like, okay, I've got about 30 years, right? And I, I don't want to burn out. So how do I think about this methodically and in ways that like still bring me joy? And yes, we hit those financial goals. But in a way that's sustainable for the longterm

Steve Folland: Yeah. You mentioned having, was it like 12 or 15 clients on the go at once?

Brennan Gilbert: 12, yeah, 15 would be nuts, but 12 is also nuts.

Steve Folland: yeah. 12 is a lot. So how, how, how do you manage your, your projects and your clients? Both their expectations, but also just your, I guess, your workload across a, a day, a week, a month?

Brennan Gilbert: See, this is why I love your podcast. I like talking about the little gritty details. I'm a huge nerd for project management. I am big on project management. I use a sauna for all of mine, [00:27:00] but quite literally, I will follow the There's an input, right? I do have clients on slack. I have clients on email.

That's kind of the two main ones. I'll have a few rando clients who want to just call me and say, can you do this? I always religiously put that into a sauna and then I have done this enough years where I understand a quick gut check This thing should take me a few hours. This thing should take me 30 minutes.

And because I understand how to estimate my time, and I'm also very big on time tracking, not when the client like asks you to, I think that's a, that's a bad practice, but for yourself to understand level of effort so that once you've done this project 20 times, That's a pretty reliable average for how much that's going to take you to be able to complete that in a successful way.

Right. And then you can also start to see optimizations. Maybe if I didn't do this part of the brand identity process, or maybe if I increased this part, right. And [00:28:00] so with all of that, when I say 12, it's not. 12 one off gigantic end to end brand identity clients. It's a few clients on subscription models who might not need me that week.

And then there's clients who just need like a business card. And then there's a few clients who need medium projects and then one or two doing big projects, right? So that's how I'm able to scale at that point. 12 giant needs clients at once, but on the months where it works out, where there's a. bunch of things, small and large.

That's when I'm able to do that, but I don't recommend it. I mean, I would say six is a good average depending on what types of projects that I'm doing.

Steve Folland: And when you say subscription clients, so is that like a retainer relationship?

Brennan Gilbert: Yeah. I'm glad you guys, that was probably my favorite part about the annual report. It's like. Playing around with pricing models. I think that's another thing that especially creative freelancers, Oh, well, you know, I'll just do hourly. I'll adjust you [00:29:00] project based. I do three models. I do project based I do hourly, even though that one isn't always everybody's favorite and I do subscriptions.

And so to answer your question with subscriptions. Let's be honest. I mean, it's a fancier way to spin retainers these days, but the nuances I think are important and love him, hate him. There's a very famous designer. His name's Brett. He owns a company called Design Joy, and he's very infamous in some circles, and other people love him.

I won't get into my personal feelings on the guy, but he's big on design subscriptions. He's big on That. And so a mentor once told me, if you don't like something, either evaluate yourself or consider it from a different perspective. And I'm like, this guy is just like burning char, there's no way he's hitting these numbers with subscription.

He's just giving everyone five minutes. Now that may or may not be true, but parts of his model were really interesting for subscriptions. Instead of retainer, the [00:30:00] big difference being retainer is. Here are five hours and here's the exact cost for those hours. And we times that by four weeks and I'm, I'm sitting around at the computer, whether you use me or not.

And it's like, it's kind of just a fancier version of hourly, at least was my interpretation of the way I used to think about it. Subscription clients pay upfront. I use points, which sounds a little silly at first, but it's a way to abstract value, right? Because we all know that. Truly, even though I work with some clients who are hourly, an hour does not equate to whatever that dollar value is that you've attributed to.

That's not accounting for my 20 years of experience to be able to do that in 10 minutes. And so if I get something done in 10 minutes, why, why am I penalized for doing it more efficiently? Right? And so the subscription is more about. Frankly, it only works if you build a partnership with the client, right?

It's really about trust, but like all my [00:31:00] subscription clients get a certain number of points and I say big websites. That might be three points medium, landing pages, single, one pagers, that's, that's two points. That's a medium project. Business card, letterhead, small stuff, you need a social graphic, that's one point.

And we do that enough weeks where they start to understand, okay, this is a five point project so that's going to take Brennan two and a half weeks, right? And then the other key is you work on one task at a time. And that might sound like a silly nuance, but it helps the client understand we're not doing a lot of context switching.

We are prioritizing feedback. We're getting through this so they can do unlimited requests. They can put as much in the queue as they want, but we work through one project at a time until we're done. And again, I've, I've done this enough years where I understand level of effort. So when I gauge something, when I say this is three points.

I actually have a method behind the scenes that I use, like [00:32:00] it doesn't translate exactly to hours, but like, I, I understand my level of effort to be able to hit those numbers. So it's not completely arbitrary, but it works in a way that, you know, it's, it's more about once it starts to work really well.

And I'm, I'm grateful to have all of my subscription clients coming up on a year renewal. It's more like the fractional model, right? Like you're, you're basically paying to have me available to work on stuff. And if you don't use me in a week. That's fine. I'll be around next week, right? And it also gives them the psychological benefit of they can cancel at any time, which I thought was another great model from these other folks who have been doing it for a while.

They, they don't cancel if they like the services, but in their head, when you're first signing them on a one month commitment, They, they can do that, right? All of these clients have paid me close to the salary of a junior designer, right? But I was talking with someone recently is I'm not selling the salary of a [00:33:00] junior design.

I'm not saying pay me this one lump sum right now and trust me. Pay me month to month and we'll see how it goes. And if you like it, it automatically renews. I have them set up on Stripe, right? So it automatically goes through. And if you don't, you can pause it or cancel it entirely. And as long, again, as long as you have that relationship and you're doing good work, they're motivated to continue to work with you.

Steve Folland: And of those subscription packages, like, are they on your website? So I could go on there and I can go right, click buy, or do I have to go into a. a process with you ahead of

Brennan Gilbert: gotta go through the process. I've, I've thought about creating a landing page for it, but like, truly, I, I do like thinking about pricing as value based. And so, the price is not gonna be the same for a multi million dollar startup versus a mom and pop bakery. Right? And, To be fair, this subscription model only works for a certain type of [00:34:00] client.

They have to be big enough to have consistent weekly needs, but not so big that they've hired in house. Right? So that does tend to be a certain type of marketing team or startup that works really well for that. But yeah, I don't list that publicly just because I'm huge on land and expand, right? I would rather do a quick project for you for 400 bucks and then we establish a relationship and then I can slowly say, Hey, like, by the way, did you know I do websites?

Yeah. Oh. And like, you need this too. Hey, by the way, you're doing all these one offs. I have a subscription model that'll save you costs in the long run. If you'd like to try that, right. And it's, it is part of sales, right. It's part of offering that so that they have options.

Steve Folland: if I pay you and I get I know my 10 points Is is that 10 points for a month and if I've not used them then they they roll over or they're gone like how?

Brennan Gilbert: And to be fair, when I set up this model, [00:35:00] I was not convinced it would work myself. I had to test it out and the clients who gave me a shot, I will forever be grateful. They, they really put a bet on me and now it's working really, really well. But yeah, I thought through those logistics. And so something like points rolling over, they do not, they're, they're weekly.

And so that helps. Again, it's like, it's more about, I'm encouraging clients to come to me. If, if you have work, send it to me. And I asked them weekly, Hey, y'all, like, what's going on? What can I help you with this week? As a reminder, points don't roll over. And I even tell them to, it's like, it, it's like, It is squishier.

So that's where the partnership is really important. You got to have a trusting relationship. They, they trust that I'm not here to rip them off. And I trust that they're not trying to do the same with me, right? They're not trying to get 40 points done in a week. But yeah, it's like the points don't roll over.

And I also tell them if, if you come to me on a Friday [00:36:00] expecting four points, they also know that I work with other clients. And so that's not doable. So the points, I think. At first sound funny and confusing, but like dev shops, these giant development agencies who come in more as consultants, they've been using methods like this ever since they were created.

Right. And so again, like, that's where I think being tangential to developers has been interesting for my career because you just think about things differently than like, Oh, you got to do, you got to do a retainer and it's gotta be hourly. And you got to. Guarantee those hours and like they're for a full month, so they could use 30 hours in one way.

Why? Like that, that puts you as the vending machine model and then they don't respect you and then they don't care about your time. But if you're truly at that high level of like, I am your fractional creative director, I'm here to help you with whatever, but I'm also not so high level that I'm not, I will roll up my sleeves and do the work for you.

Right? So we'll think through the strategy, we'll execute, [00:37:00] and we'll do that at a cadence that makes sense for you. I have one client on a lighter plan, and there are some weeks where if we hit points, I tell her, Okay. Okay. We can do overages, but that'll be an additional fee because you did hit that cap, right?

So you got to make sure that it's not arbitrary. You do got to make sure that you're tracking that and like, telling the client, this is one point. I think I can get it done by tomorrow. Like being very communicative is key to that model, but it works. And I, yeah, if folks can shoot me an email, I'm happy to.

Talk about that all day. That one's, that one's interesting, and I'm, I'm glad I tried it. It doesn't always work, but for the right clients, it works really well.

Steve Folland: Yeah, because how do you avoid Overworking, I guess, as in

Brennan Gilbert: Mm hmm.

Steve Folland: thinking, Oh, well, I've, yeah, well, you see what I'm saying. You mentioned Friday. Okay, sure. You bring in the points on a Friday, but what if like suddenly there's a load of work comes in on [00:38:00] that Wednesday evening and suddenly your Thursday and Friday don't look the way you thought they were going to look

Brennan Gilbert: I will say that's just trusting fate and hoping that things work out. By and large, when I was worrying about it, I was stressing myself out more than I needed to. These days, those scenarios do happen, and And frankly, I've chalked that up to a part of being an entrepreneur who has different payment models because of that, there will be the occasional weekend or the occasional Tuesday night where I have to sit down for an extra five hours just to get stuff done.

And so. I think that's, that just comes with the territory of confidence in, in saying what you'll do and doing what you're, what you'll say, right? And if that client comes to me, I will get that done, right? And like, I think it's just, it's about expectation setting. And truly, if they come to me on a Thursday, I'll push back and say, look, like I am already [00:39:00] queued up.

I know that you haven't used anything for the last two weeks. Is this flexible? If they say no, I like I'll figure this out for you. Thank you for trusting me. But by and large, I'd say 80 percent of the time, they are flexible because we have that relationship. So that exact scenario almost never happens.

But when it does. You do have to just take a deep breath and dive into the work and, and figure out how to get it done.

Steve Folland: And just one more thought on this particular topic is, is really around taking time off. So what happens when you're going to take a week off?

Brennan Gilbert: I get more stressed about taking time off than I think my clients do. That's the beauty of it being month to month. And while I will likely be offering monthly, quarterly, and annual in the coming year, I'm still exploring that. The month to month is beneficial because I effectively prorate them.

As soon as I have a vacation planned, this is happening in a few weeks, my wife and I are going [00:40:00] out to the beach in a few weeks, we planned this like three weeks ago, I then, I'm able to look at the monthly rate, I calculate the number of work days available in that month, I divide that rate by the number of days that I'm missing, and then I prorate them, basically give them a coupon in Stripe that says for the month of July, please know I'll be gone for this week.

You will not be charged for that time. If the tie, like if they've already paid because they pay in advance and say, I don't always plan things eight weeks in advance, Then they get a prorated discount for the following month and worst case if they're like, no, we want a refund for this. Well, that's a red flag for me because that means they're probably going to churn.

So then that's a different conversation entirely. That hasn't happened yet. Knock on wood, but. That's how I think about it. And like, again, that's why I joke because projection wise, the subscriptions are great, right? They're able to [00:41:00] be slow and steady income, even when I don't have anything else. So I have a hard time justifying discounting for clients because it's like, well, that that's what I was planning against, but I realized like, again, long term you can't think about it that way.

And it's like, If I take one day in a week, I just frontload the week, and I'll tell clients I'm off on Friday, but we're doing all your stuff early, so just please let me know proactively. If I take more than three days, that's when I'll do the refunds, and it's like, it's just easier. I mean, with this vacation coming up, technically we're not leaving till Tuesday.

I'm like, okay, I'm, I'm like being stingy with my own PTO here. I almost didn't take Monday off and I was like, just take one day. And the funny thing is with the rate it's not anything crazy. Like when I break it down to a day, it's like 80 per client. Okay, just, just lose out on the 400 bucks and like, take the time because the time's a lot more [00:42:00] important.

The time is what we can't get back as freelancers, you know? So yeah, that's how I think about it. And then the hourly clients, it's just a pause. And then the project clients, I just work around it. Right. So definitely a good point to call that out. Subscription is the hardest model to account for vacation.

You just have to acknowledge that you're not going to be making those dollars for those days that you're gone.

Steve Folland: So interesting. Thanks for chatting about it. I know you've not been freelance that long, but if you could tell your younger self one thing about being freelance, what would that be?

Brennan Gilbert: Honestly, do it sooner. It was something that I had obviously, like, on the side. I had done it my whole career and I always, always, always loved it. I just didn't have the confidence to go full time. Now, set yourself up for success, right? Put whatever safety nets you need to in place, especially a community.

Have people who are willing to Help you out, including financially if you ended up needing it, but bet on yourself. Go, go earlier than you [00:43:00] think you might is probably the main thing I would tell myself.

Steve Folland: It's been so good to talk to you. Thank you so much and all the best being freelance!

Brennan Gilbert: Thank you so much. That was fun.

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