Journey of a freelancer to agency owner - Brent Weaver

51:1 Journey of a freelancer to agency owner

How a struggling freelancer grew and sold a successful agency... twice!

Lee Matthew Jackson
Lee Matthew Jackson

Struggling to break out of the feast and famine cycle? Do you feel like you're constantly putting out fires and not making the progress you want in your business?

Brent is a seasoned agency owner who started his first digital agency at the tender age of 17. In this episode, he shares his journey of navigating the challenges of running an agency, from landing his first clients to eventually selling his business not once, but twice.

💡
Calling All Freelancers & Early-Stage Agency Owners
Free training with Brent! Click here

Through his own experiences and the countless agencies he's mentored, Brent has discovered the key strategies and mindset shifts that can help freelancers and small agency owners break through to the next level. He emphasizes the importance of having a clear understanding of your ideal client, a strong sales process, and the confidence to charge what you're worth.

But perhaps most importantly, Brent stresses the value of seeking out business mentorship and developing your entrepreneurial skills. As he puts it, "I think as you start to make that transition into agency owner and business owner, you need to start to diversify your basic business understanding."

💡
Calling All Freelancers & Early-Stage Agency Owners
Free training with Brent! Click here

Whether you're a freelancer, small agency or simply stuck... this episode is packed with actionable insights and inspiration. So tune in and discover how you can build a thriving, sustainable business on your own terms.

Free training

Brent is offering free training for all freelancers and early stage agency owners. You can find out more here.

Video

We recorded this podcast live, so if you'd prefer to watch you can do so on YouTube.

Key takeaways

I will never get bored of hearing Brent share his experiences. Here are a few of my aha moments as he spoke:

  • Breaking the feast and famine cycle is crucial for freelancers and small agency owners to achieve sustainable growth and success.
  • Having a clear understanding of your ideal client is essential for effective marketing, sales, and delivering value.
  • Developing a strong sales process and the confidence to charge what you're worth are key factors in building a thriving business.
  • Seeking out business mentorship and expanding your entrepreneurial skills are critical for transitioning from freelancer to successful agency owner.
  • Building a thriving, sustainable business on your own terms is achievable with the right approach and guidance.

Connect

You can connect with Brent via:

💡
Calling All Freelancers & Early-Stage Agency Owners
Free training with Brent! Click here

Transcript

Note: This transcript was auto generated. As our team is small, we have done our best to correct any errors. If you spot any issues, we'd sure appreciate it if you let us know and we can resolve! Thank you for being a part of the community.

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Lee
Welcome to the Trailblazer FM podcast. I'm your host, Lee. On today's show, we're speaking with not only the most handsome man on the planet, but also my friend. It's Brent Weaver. How are you doing, mate?

Brent
I'm doing awesome. Thanks, Lee.

Lee
I just thought I'd disarm you there and just soften you up as you join us here on the show, mate. Thank you so much for coming on. Could you just give folks an update? It's been a while since you've been on the show. What's been happening in your life? And then we'll get cracking.

Brent
Yeah. I'm still running. UGURUS. I'm not sure when the last time I was on, but we were acquired by Cloudways, and then we were acquired by DigitalOcean. And so it's been definitely a journey. It's been really cool to be able to help more agencies and freelancers through the Cloudways platform. We're still helping to accelerate digital agencies of all sizes. And yeah, it's been really cool to see the team grow from pre-acquisition. We had five or six full-time people, and I think now we're close to 20 people, which has been really cool. On the personal side, still just enjoying riding my bike a lot, hanging out with my kids and my family, my beautiful wife, and just living the life, man.

Lee
Amazing. Folks, we'll make sure we link to the previous episode. Like I said, it was about two years ago, but it'd be great. There's so much valuable content in there when me and Brent were talking. That was around the launch mate of your book, I believe. Oh.

Brent
Yeah, so pre-acquisition. We were still our own company, but it's been a lot of fun. I think as a founder, a lot of times we have a goal of maybe one day growing our business to the size that we can sell or be acquired. It's been a real honour to be a part of the DigitalOcean team now.

Lee
Well, let's have a conversation. Let's go back in time. When you were 17, you first started your first agency, which is pretty incredible. I presume your hair was already the colour it is.

Brent
Yeah, it was clearly just a couple of years ago that I started my first agency, Lee.

Lee
Well, when you started at age 17, what were your biggest challenges in the early years? Because just for context, folks, Brent has sold twice, so I'm intrigued. Take us right back to age 17, you're starting your agency. First couple of years, what are the biggest challenges?

Brent
I think getting your first client. I'm not going to say that our first clients fell into our lap, but I feel like we did let people know that we were starting a business. It seemed like something that people were really interested in. At that time, back in 1999, the Internet was relatively new, the web was new. I was just telling people that I could build websites, and I was really into building websites. Every website I built, I showed people that website, probably more people than ever wanted to see the website. I was messaging grandma and stuff like, You got to look at this website. She's like, What the heck is a website? I just told a lot of people about it. I got some clients, but let's call those my F&F clients, my friends and family clients, weren't really paying a lot of money for those clients. When I got my first real opportunities, these were people that I did not know, like or trust. They weren't part of my family. They were totally new relationships. They would ask me things like, Hey, this sounds great. We'd love for you to build this website. Can you send us a proposal?

Brent
And as a 17-year-old kid, I'm like, What's a proposal? And this is obviously pre-Google. We had like, AltaVista and WebCrawl at the time, but googling website A proposal nowadays gets you some really sick, awesome resources. Back in 1999, it was nothing. I mean, there was no content about writing proposals, about having a proposal template. And so literally, I called a friend of mine who I knew his dad, and I'm putting air quotes for you podcast listeners, did business. That was basically how sophisticated I was. And I asked I said, Can you help me write a proposal? Now, looking back on it, my friend's dad did logistics for a large clothing company. He didn't know anything about writing proposals, website proposals, whatever, but he helped me write a proposal. It looked a lot like a five-paragraph essay that you'd write for your college entrance exam when it was all said and done.

Lee
That's amazing though. But the one thing you did there, regardless of the fact he was in logistics, is that you reached out to to somebody for help. You didn't try and do it alone. You didn't put forward a terrible proposal because you at least had some pointers by somebody who had some chops in business, regardless of the fact it was nothing to do with Web. I would love to see what that proposal looks like.

Brent
I would as well. I think at some point I did find it in my archive, within archive, within Archives. It just said the record straight, it was a terrible proposal. It was awful. It was atrocious. It had my life story on there. I think somebody As a brand new business owner, one of the things that I think we struggle with is this idea of imposter syndrome. Why would somebody trust me when I have no portfolio, I have no clients of record, I've never gotten anybody I've had your results before? Why would somebody trust me? And I think my natural solution to that was, let me tell you why I'm a trustworthy person. I'm going to tell you why I love building websites, and I'm going to tell you about why I'm somebody that you could trust to do this project. And I think, that's a very, not looking back on it, it's a very me-focused proposal, when really, I think now, looking back, understanding what I do now about business, clients really, rightfully care mostly about themselves and what problems they have. And while they do need to trust you and they need to have some signals that say, Hey, this person isn't going to take a check and run away and go to Cancun and ever reply to my emails.

Brent
But generally speaking, They're very interested in what their own problems are and how you're going to solve those. I think if you show a client a good plan and you are able to communicate about their problems effectively, that that's going to be way more important than any past case studies Or as I wrote my five-paragraph essay on my personal history. You can definitely provide much more value through that process versus feeling like you're an imposter.

Lee
I love it. We all do struggle with that imposter syndrome. I think even now as agencies, we feel like we have to really up our creds document, as it were. We're attaching all of our creds and we're really trying to prove our medal. When, like you say, in most circumstances, a client wants to know that you've understood what they want to achieve, you've understood their problems, and you've presented to them a solution that they believe in and that they say, Yeah, all right, we'll part with some dollars to make this happen. Let's go. Now, you've obviously developed over the course of a few years a skill in creating proposals beyond a five-paragraph. Look at me, I'm great. I remember last time when we spoke, you talked about a feast and famine cycle. What point was that happening and how did you break out of that?

Brent
I would say in some level with an agency, unless you have really solid recurring revenue, you've got a really well-developed book of business, you have proven systems for how to generate leads, proven systems for how to convert those leads into clients, proven systems on how to take those signed proposals or engagements and actually deliver value on that. I think until you get to that point, you're always in a little bit of a feast and famine cycle. For me, early days, expenses were incredibly low as a single college student who could live with roommates and survive on mac and cheese and hot dogs and cheap 40s back when I was drinking. Expenses were very, very low. In the single couple of a few thousand dollars a month. And so that feast and famine cycle at that point in time, the risk was not that high. My business partner and I could land a couple of 3,000 to $5,000 clients a month, and we could keep the lights on and continue to develop our skills and develop our business. I think in the early days, we were able to keep that cycle of feast and famine relatively under control.

Brent
Now, our business did grow. One of the early mistakes that we made was we started to make business decisions based on what we thought you were supposed to do as a business owner. We thought we were supposed to hire employees in order to grow the business. We thought that we were supposed to get an office, which I think is a lot less common nowadays, but back then, to do business right before Zoom, before really awesome teleconferencing, to collaborate and do stuff. A lot of it had to be in person more so than now. But we got business, we got office space, we got a whole bunch of cool tools that we thought that we needed, all this stuff. We started to grow our expenses. I think that's where that feast and famine cycle really hit us, where if we didn't have those things I just spoke about, systems, generally systems, sign clients, getting high value clients, that stuff. Then all of a sudden, if we didn't land enough clients one month, my business partner and I were both cutting our own compensation in order to keep the business afloat. That's That's when we started to make other really bad decisions, putting a lot of our payroll expenses on things like credit card, grabbing loans, trying to figure out how to Rob Peter to pay Paul, doing the cash flow shuffle.

Brent
Once I was expenses started to explode, we had to keep pace with that in order to feed the monster. That's when the feast and famine cycle became potentially critical to the business.

Lee
Like you say as well, that actually leads to some really bad decisions. I can remember for us, not only did we get credit cards, we were also borrowing money from... Essentially, the money we'd put aside for the tax, so the taxman was going to come for us as well.

Brent
Yeah, done that.

Lee
By the way, maybe I shouldn't admit it. I don't know if I should admit that, but we paid our tax eventually, so we're all good now. It was all in the past. Thanks, your Majesty's government. I've lost track now. I panicked. They don't listen to this podcast anyway, so we should be good. But anyway, we did all of that, and that also led us to accept new jobs with clients who were definitely not ideal for us, but they had a chequebook. We were therefore accepting low-value business with essentially low-value or low-compatible clients, and things just got worse and worse for us. Now, for you guys, you did get out of that feast or famine cycle, and that actually eventually led to you guys actually selling the agency, which is phenomenal. So what practises or strategies do you believe led to your success and, of eventual sale?

Brent
I think there's different stages of an agency. There's what I call the traction stage, where you're just trying to find market traction. I don't think it's necessarily a bad thing to gig in that stage where you're taking jobs like anybody with a chequebook and you're able to keep the business afloat. Now, in the traction stage, what you probably don't want to do when you're not really sure who your ideal customer is, when you're not really sure what your core offering is, when you lack systems and processes, and you don't really have repeatable methods to get clients' results. Things in that stage, you want to keep your expenses really low in that stage. You want to stay really flexible. You don't want to put yourself in a position where you're having to rob Peter to pay Paul or take out really large, expensive loans or maybe take a loan from the government. We didn't pay our payroll taxes for close to three It was the worst mistake we ever made. We built up a balance with the IRS of $135,000. That's a lot of money to pay off. Actually, the IRS is great about charging you interest and penalties.

Brent
The interest is reasonable. The penalties, however, are not reasonable. It's actually a really expensive place to get capital to grow your business besides the fact that it's likely unlawful. You're going to pay a lot of interest and penalties with that. There are more smart ways to fund a business early stage. That's something that I didn't learn until later on. There are also expenses that are great to spend with borrowed or raised capital. The general payroll for employees that you probably can't afford is a really bad reason to take a loan or use a credit card. However, if you're just getting your business going and you need some runway to cover your own expenses, to to keep focused on the business. That's not a bad reason to use credit cards or a personal loan or a family or friend loan. That's a great reason because it's helping you launch your business. But if you have three employees and you have no work for them, or they're not very busy, or you could swap them for contractors, keeping those employees around just to save face or avoid a difficult conversation, those are really bad reasons to take out a personal loan.

Brent
At one point in my agency, I took out $50,000 our personal loan in order to cover payroll because I didn't want to have a hard conversation with employees. I didn't want to impact our culture. Now, it took me years to pay off that loan. It took us years to pay off the debt with the IRS. In hindsight, we should have rightsized our overall organisation. I should have gone to mentors and said, Hey, here's the situation. We only have this much business. We have this many expenses. How should we adjust the business? Instead, we tried to keep up appearances. Now, I can say, looking back, we were able to correct the business. The things that we did to do that, first and foremost, we got really clear on who we served as a business. And there's a lot of reasons to doing this. The best reason is that it helps you focus your marketing activities. No agency, no business has unlimited marketing budget. You probably, as a brand new business, have a very limited amount of resources to go out there and find new clients, both time and money. And so to focus those resources You do need to get really clear on who your customer is.

Brent
And so for us at that time, we were selling to some clients who had a lot of money, and we were selling to some clients who had no money. Turns out the ones that had money were established businesses and organisations. They'd been around for at least five years. They had revenues of at least a million dollars a year or more. And so that was one of the first things we did. We just said, Hey, we got to stop selling to people that don't have a business, that are starting something new, that have an idea. These are all very conversations to have, but they were just leading to lots of people that had $1,000 spend, $1,500 spend, and it was absorbing a tonne of my time. And so we just got a little bit more clear about who our ideal customer was, and that helped us to really start to dig ourselves out of that hole.

Lee
That's phenomenal. Being clear with who it is that you're serving, it doesn't necessarily have to be a niche. I mean, for me, it had to be a niche. We had to really focus on the events industry so that we could understand exactly who we were talking to. But regardless, whether it's a type of company, customer, avatar, etc, you learn how to talk to them, don't you? You learn how to find that particular type of business as well, because I do remember being a freelancer and I was talking to so many different types of companies. I'd be talking with a startup who had 200 pounds to spend on a website. The following day, I'd be in an office of a 50 million turnover company, absolutely bricking it, thinking, What am I doing here? And then still being scared to say that it might be about a thousand pounds and then potentially being left out of the room. Without any direction, without an understanding of who it was I was serving then, it was definitely a real struggle. For me, same as you there, having a real handle on who it is that we're serving, what it is that we're doing for them, and also having that confidence in yourself that 17-year-old Brent didn't have when you gave the five-paragraph essay about why they should choose you, which I think is still pretty cute.

Lee
I didn't even know about you, mate. It's so cool.

Brent
I didn't even go into my pitch for that meeting. I had just recently seen the movie The Matrix. I'm sure you all know. I had this image in my head of basically Keanu Reeves dressed in all black was the coolest person that you could possibly be. I remember I went to Banana Republic and I brought black slacks, black belt, a black shirt, a black jacket, a black tie. And that was my first. Just imagine 17-year-old bread going into a business meeting. I was this guy that was like, I think it was an import-export business in some random office park. I went in there and I was wearing all black. Just looking back on it, some 55-year-old guy in a sport coat in jeans in Plano, Texas, has this neo lookalike come in with the glasses. It was bad. It was so bad. But I was a nerd of nerds. But I think I still went in. I I still showed up, even if everything that I was doing was not correct, and it could have been much better. I did land a couple of thousand dollar client with that proposal. I probably could have gone with a piece of paper in a napkin that just said, Hey, two grand to build you this import expert website.

Brent
But the fact that I showed up, I think was key. In one of the things as I'm talking to early stage agency owners, a lot of folks aren't showing up. They're not sure on if they can help somebody. Instead of having a meeting with them and figuring it out, they sit and they think about it and they research and they plan and they research, versus just going and having a meeting with somebody and saying, Hey, what do you need? And, Okay, I can do this. This is how much it's going to be. Maybe you're not wearing the right clothes or saying the right things, but the fact that you're showing up, I think people, a lot of times, are going to give you the benefit of the doubt, especially early stage. They're going to want to believe in you. They're going to want to help conspire to make you successful.

Lee
Now, a lot of our audience may are either freelancers or they are small agencies who are perhaps two or three employees and are in that feast or famine mode. Perhaps they put some money on a card to pay staff, etc. They're very much where I was as well just a few years ago, and it was a very scary place to be. What do you wish you'd had back in those times in order to help you grow your business and also get out of that?

Brent
I think just besides having the core business skills, I spent a lot of time early on. If you looked at one of my very first offices I ever had, I had this huge stack of programming books like PHP, HTML, CGI, Per, all this stuff, like C+ products. I was really into the craft. I think as a freelancer or a practitioner, that's definitely like, you do have to spend a lot of time working on your skills because people are obviously hiring you. I think as you start to make that transition into agency owner and business owner, you need to start to diversify your basic business understanding of how do I create a marketing strategy? How do I actually build awareness for a business and find clients? How do I actually sell? I talk to a lot of agencies and people that are doing... They love doing the work, and they'll say things like, I don't want to be salesy. I don't really want to sound like I'm selling or whatever. You don't have to be salesy, but you do need to learn some basic fundamentals about how to build value. I'll talk to agencies that are doing mid six figures, Lee, and I'll ask them what their sales process is, and they'll say, Well, we have a 30-minute meeting, and then we even Nail somebody a quote.

Brent
And I'm going, Oh, my gosh. You are working with multimillion dollar businesses that have really complex problems, and you're going surface level at best. You're leaving probably tens of thousands of dollars, if not hundreds of thousands of dollars on the table. And so we'll just make a couple of quick changes into a business like that. And usually we'll see some really phenomenal success for them by just helping them true up those business skills. And so I think going back to early, I hate to I don't really regret anything, but whatever. I think I would have tried to find a stronger business mentor that would have really worked with me, maybe found an agency owner, even though they were less common back then. And I would have said, Hey, can you help me with some of my basic business stuff? At the time, I thought, Why would a competing business ever do that? Why would they ever help me? I think what I know now is that there's tonnes of people out there that want to help other businesses, even if they're the same business as them. I talk with tonnes of agency coaching businesses. I'm very open book about what we're doing and what's working, what's not working.

Brent
I think that's the type of thing that I would do that would make us more successful. Now, the agency that I co-own now, very similar to your event engine, Unlimited WP, we're a white label WordPress shop. When we launched that agency, we We launched it with a very, very clear ideal customer. We knew exactly who our customer was, down to what they're thinking when they wake up in the morning thing. We launched with a very clear offer. We knew exactly what we wanted offer. Now, we've made tweaks and changes to that. We launched it with some actual startup capital. We had money to hire staff. We knew what our runway was. We could basically operate the business for at least a year with very little growth. Now, fortunately, Our strategy did work really well because we knew it. We were able to get lots of clients very quickly. We were able to scale that business up to 100,000 a month plus in under 18 months. I look at that business and I think, Okay, the amount of time it took me to grow my first agency to 100,000 a month was a lot longer than 18 months.

Brent
We've been able to do that much faster now because we understand those business principles. We have a lot more confidence, and we don't feel like we're gambling or just throwing some spaghetti at the wall and hoping it sticks.

Lee
No worries. There's plenty of spaghetti on my walls. Just have to keep painting over it. Now, you've highlighted there something that's super important. Somebody who's in the very early stage as a freelancer or a small agency, they need some help. There is often a lot of noise out there, a lot of noise that assumes you are a lot further on than you actually are. I mean, for yourselves at YouGurus, you guys have for years now been providing medium to larger agencies that that support and that growth. Now, I believe you're going to be doing a live event specifically for freelancers and for smaller agencies. Can you tell us a little bit about what that entails? Also, I believe it's a free live event, I'll I'll throw that in there.

Brent
Let us know. We're actually doing an event series. We're doing three live events. The first one is on Agency Fundamentals, helping people really unpack their dream for starting a digital agency. Maybe they have a side Maybe they're a freelancer. I'm still surprised that how many people that have a business are generating some revenue. They haven't actually sat down and said, Okay, well, what am I doing? Why am I doing it? What's this thing going to ultimately achieve? We're helping them first build that foundational element. That's going to include just some of those key things you got to do to get the business live and be able to take money. Our second event is purely on how to get more clients for your agency, get that continuous lead and client flow. And then our third part of the series, we're actually bringing in very successful multi-six and seven-figure agency owners. Some of them are going to be some of our mentors for YouGurus, and we're going to pull back the curtain a little bit and have them talk about some of the things that they've done that have helped them to be successful faster. Our ultimate goal is if you want to start a digital agency, there's a lot of simplicity to what you have to do, but it doesn't necessarily mean it's easy.

Brent
But if we can help you avoid some of the costliest mistakes, if we can shorten the amount of runway that you need to become a stable business that's doing at least six figures, then I think that would be a huge success. If that's something of interest to people, we'd obviously love for them to join that live event series.

Lee
Awesome. I believe actually is today. We couldn't record last week. We had roadworks going on. It was ridiculous. We're going to try and get this episode out as soon as possible, i. E. Today or tomorrow. Folks, you'll still be able to join some of these live events. But Will there be either recordings or a way that people can still connect with you afterwards? Should they be listening next week?

Brent
Yeah. If you just register for the event, if you register before we kick off, then obviously you'll get the full schedule. If you register after we've kicked off the event, on the thank you page and the emails, we'll link you to the prior recording so you can catch up with us and make sure you're staying on top of the free training series.

Lee
That's amazing. Folks, you know where to go. Go and check the description down below. If you're watching us on YouTube, go and check the show notes or trailblazer. Fm as well for all of the links that you need to go and find out more about the live events, the event series, Brent. Thank you so much, mate, for your time and also for your generosity and just sharing all of that personal information to help other agency owners. I know it's your mission. I've seen it a few times in various different places. Is it like 10,000 agencies you want to help? How far are you with that number?

Brent
Yeah, with our core pro and elite programmes, we've graduated, I think, right around a thousand agencies from there. And so part of this launch series is to help us, obviously, accelerate even more agencies. We found a lot of people at that side hustle early, early stage. They need help, and a lot of folks offer that help maybe a little bit further along. And so we decided to tackle this problem and help people launch faster and more effectively.

Lee
Well, mate, all the very best of luck with it. And thank you so much for your time. Have an amazing day. Take care. Sure.. Cheerio.

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PodcastSeason 51

Lee Matthew Jackson

Content creator, speaker & event organiser. #MyLifesAMusical #EventProfs