Today’s coaching call is with Keegan who’s calling in from Louisiana, USA. Keegan is building a web design business (something Clay knows a lot about) on the side of his day job (something I have tons of experience in). And while Keegan has a very clear picture of where he’s going, he’s not exactly sure how to attract clients on a more consistent basis. This hurdle launches us into a conversation all about the power of finding local clients. We outline a few reasons you should try focusing on lo...
May 13, 2021•50 min•Season 11Ep. 2
On today’s show, we talk with Karl who’s holding on tight while his writing business is growing fast. After writing for a few highly technical development blogs, Karl’s business exploded and he now works with 50 writers to deliver articles for his clients. And while Karl is crushing it by some standards (his writing business has quadrupled since January), he’s naturally feeling like a bottleneck in his fast-expanding business. Clay and I have a fiery chat with Karl where we uncover what has done...
May 06, 2021•55 min•Season 11Ep. 1
On today’s episode we chat with Brady, who is building a web design business from his home in northern Idaho, USA. Brady has already built up a small team of contractors and aims to get the business running almost on autopilot in the next 6-12 months. To do that, he’s got to first perfect his sales process and then train someone else to do it. But he’s got a bit of a sales problem. After drafting a proposal and getting on a call with a client, too many people are just saying “no”—making it hard ...
Apr 08, 2021•59 min•Season 10Ep. 12
On today’s episode, we chat with Brendan—a sales consultant who wants to scale his business to something bigger. And while he finally started hiring people to help him scale, he’s still a bit unsure about a path forward. He’s working on a course for more passive income and he’s trying to transition away from one-on-one consulting gigs to more of a sales coach role. Since Clay and I are fresh off our recent 5-day recurring revenue challenge, we have some good advice for his course’s future and si...
Apr 01, 2021•52 min•Season 10Ep. 11
On today’s show, we chat with Jon who’s a physical product designer and prototyper. Jon’s got a highly technical business—which you’ll see as we chat with him on the episode today. That means that Jon is very smart when it comes to product design and 3D printing, but has a hard time translating that expertise into language that appeals to clients. So in today’s episode, where I'm also joined by my friend and guest coach Matt Olpinski, we walk Jon through some important ways to think about messag...
Mar 25, 2021•50 min•Season 10Ep. 10
On today’s show, we chat with Christine, the founder of Bryant Creative Company. Christine has a nice freelance business where she works on graphic design and branding for her clients. But over time, Christine has also begun to offer additional services such as web design—which, frankly, she doesn’t enjoy as much and she’s not as good at. That brings up a whole lot of questions on our call such as: should I outsource jobs that aren’t a fit? Or should I decline them altogether? If you’re not sure...
Mar 18, 2021•45 min•Season 10Ep. 9
On today’s show we chat with Augusto who’s running a local branding and video marketing company in the United States. Augusto has chosen to target local latino businesses because he feels they’re underserved and can really use his expertise. But Augusto keeps hitting a wall: his target audience is overly cautious when it comes to spending. Which makes it hard to charge premium prices for his work. So what can you do when you’re worried you’ve got the wrong target audience? Today, I’m joined by g...
Mar 11, 2021•1 hr 2 min•Season 10Ep. 8
On today’s episode we chat with Adii Pienaar who recently published a book titled Life Profitability: The New Measure of Entrepreneurial Success. As someone who’s very motivated by the lifestyle that freelancing and entrepreneurship can offer, I was intrigued when I first learned about Adii’s book. So today, Clay and I have a heart to heart chat with Adii all about the lies about "work/life balance" and how to build a business that doesn’t ultimately consume you. If you’ve ever felt burned out w...
Mar 04, 2021•54 min•Season 10Ep. 7
On today’s episode, we have a conversation with Matt Essam who helps freelancers attract and find their dream clients. Have you ever felt like you are more of an employee than a partner when it comes to your client relationships? Maybe you feel like you don’t have any creative input on your projects. Or maybe you feel like you’re underutilized pushing pixels, moving commas, or doing some other menial tasks for your client. If this sounds familiar, you’ll want to listen to our conversation with M...
Feb 25, 2021•1 hr 1 min•Season 10Ep. 6
On today’s show, we check in with Margaret Ryland. Now, if that name sounds familiar, that’s because Margaret joined us originally on Season 8 to talk about her branding and design business. Since we last talked, Margaret has had some luck on collaborating with other creatives, but is still struggling to build out the processes required to actually make a first contractor hire. It’s a big hurdle, but if she can’t push through it, she might be stuck as a one-person business for the rest of her ca...
Feb 18, 2021•51 min•Season 10Ep. 5
On today’s show, it’s just Preston and Clay. That’s because in early January, Preston asked Clay how things were looking for the new year and his response was something like: "I’ve already hit my 6 month revenue goal." Yeah, it was January 7th. NUTS! A couple weeks later—Before January was even over—Clay shared that he hit his complete revenue goal for 2021. That’s 12 months of revenue just in January. Naturally, Preston had to get clay on a call and find out what he had been doing. It’s a conve...
Feb 11, 2021•49 min•Season 10Ep. 4
On today’s episode we have a coaching call with Shelley, who works in the music industry—which can be a tough gig right now, but Shelley is making it work. There’s just a small problem with her principal business—booking artists into venues. Getting clients to understand the value Shelley brings to the table is proving more difficult than she imagined. After digging a bit deeper, Clay and I realize this is a simple messaging problem. A common pitfall in marketing. If you, like Shelley, want to g...
Feb 04, 2021•52 min•Season 10Ep. 3
On today’s show, we have a chat with Erica who, frankly, intimidates both Clay and me. That’s because Erica is working with some of the brightest people in the world to solve some of the biggest problems faced by humanity. But despite working with some incredible clients and solving some meaningful problems, Erica is stuck when it comes to moving her business to the next level. What we uncover during the conversation is Erica (like so many of us) is perhaps getting the cart before the horse by d...
Jan 28, 2021•48 min•Season 10Ep. 2
3 Ways to Spy on Your Target Audience On today’s episode, we have a coaching call with Nikolai—a freelance Webflow developer living and working in New Zealand. Nikolai’s entire freelance business completely turned around when he decided to focus exclusively on Webflow, showcasing the power of finding your niche as a creative. And while Nikolai has seen a nice bump in new leads and more projects from sites like Upwork and networks like Dribbble, he’s not 100% sure how to find more of his ideal au...
Jan 21, 2021•1 hr 1 min•Season 10Ep. 1
On today’s episode, we have a great coaching call with Andrea, who’s growing her agency—helping companies get the most out of the popular marketing software, Hubspot. Andrea has hired contractors to help grow her business in the past and just a month before this conversation, Andrea hired her first full-time employee. Which is a big deal. It’s also led Andrea to start wondering what exactly she needs to be doing as a manager or a leader which launches us into a great conversation about entrepren...
Dec 17, 2020•1 hr 7 min•Season 9Ep. 14
On today’s episode, we chat with Yusef who’s building his own small product design agency. Yusef’s got a lot going for him: he’s got great cashflow, he’s getting new clients regularly, and he enjoys the work he’s doing. But when it comes to the most profitable projects in his business, he’s limited to working on only 8 at a time. That’s a big problem. And since Yusef hasn’t built out the infrastructure he needs to scale the most profitable part of his business, he can feel the impending plateau....
Dec 10, 2020•1 hr 5 min•Season 9Ep. 13
In today’s episode, we chat with an up-and-coming agency-builder, Maddie. And during our conversation we come up against one of the most common issues hold many of us back: Getting out of our own way. The thing is, Maddie is extremely bright. She’s got a lot of great things going. And she’s got more freelance work than she can take on alone right now. But, like so many of us, she might be overthinking a few decisions in her business that could affect her success over the next few years. Follow a...
Dec 03, 2020•48 min•Season 9Ep. 12
On today’s episode we mix it up a bit with Craig Solid—a consultant in the healthcare space. Craig’s business is going well and he’s trying to figure out how to better serve his clients on an ongoing basis and potential find some subscription revenue as well. What we uncover is a potential mismatch between the target client and product offering. All of us leads us into a much-needed conversation about offering the right services for the right people at the right time. It’s an eye-opening episode...
Nov 26, 2020•59 min
On today’s show I (Preston) have a really great conversation with James O-Reilly, an indie artist who’s working on making the transition from freelancer to founder. James has had heaps of work come in over the last year which is good because he's making good money as an artist, but he’s not exactly sure where to go next with his business. Should he hire more artists? Should he hire a project manager or a sales person? And if he hires now, will work dry up and he’ll be in a bad place financially?...
Nov 19, 2020•58 min•Season 9Ep. 11
To listen to more episodes or subscribe to Remote Works, click here. On today's bonus episode, I share with you a fun podcast called 'Remote Work' from the team at Citrix. You know how, before Covid, only a relative few of us knew how great it was to work from anywhere? Well, Remote Works is on a mission to highlight the new ways that millions of people are now working—from wherever they want. Remote Works features stories of digital nomads working from the beach in Barbados, Bali and beyond. Bu...
Nov 17, 2020•24 min•Season 9Ep. 10
On today’s episode, we chat with Chase, a co-founder at Electric Eye. They help Direct-to-Consumer Shopify brands make more money. Like Clay and me, Chase started out as a freelancer, but over the last five years he and his business partner have grown their agency to eight employees. In this conversation with Chase, we talk about all the things we three wish we had known about making the transition from freelancer to founder. We cover everything from hiring (of course) to when you should niche, ...
Nov 12, 2020•1 hr•Season 9Ep. 7
On this week’s episode, we check back in with one of our favorite guests from last season: Amy Kuo. Amy’s business is growing well and she even hired her first intern this year. But she still has a lot of questions about hiring and outsourcing. And since Clay and I believe whole-heartedly that people are the best possible investment you can make in your business, we have a lot to say on the subject. If you’ve ever worried about introducing your employees to clients, letting go of important tasks...
Nov 05, 2020•53 min•Season 9Ep. 6
You'll be happier and wealthier if you can learn how to attract the right kinds of freelance jobs in your career. On today’s episode, I’m joined by a special guest coach, my friend Matt Olpinski, as we offer some coaching to Wyatt Hill. Wyatt’s got a really unique situation: his boss allows him to make connections with customers at his day job and then pitch them his side-hustle services. While this setup is incredible, it also has Wyatt a bit worried: as he gets more successful, if he chooses t...
Oct 29, 2020•51 min•Season 9Ep. 5
On today’s show, I’m joined by a good friend of mine, Chelsea Baldwin as a special guest coach. Together, we coach Australian freelancer-turned-agency-builder Caroline. She has built up a nice freelance business and has begun to work with subcontractors to begin scaling her business. But she’s realizing it’s harder to transition from solo freelancer to full-on agency than she initially expected. Chelsea and I coach her on two critical tasks: How to get her clients to start treating her like an a...
Oct 22, 2020•51 min•Season 9Ep. 4
On today’s episode, Preston has a one-on-one conversation with James Rose. James is a total rockstar when it comes to automating tasks in your business. In fact, as you’ll hear by the end of this conversation, in order to accomplish everything James automates in his business, he’d have to hire a full-time employee. Instead, he leverages affordable tech and brilliant workflows to save money and get more done. If you find yourself bogged down, short on time, or hoping to save money as you scale yo...
Oct 15, 2020•59 min•Season 9Ep. 3
On today’s show, we have a really great conversation with Natalie, who has built a nice freelance design business but has also encountered some serious trouble when it comes to hiring. And even though Clay and I both know how critical hiring can be to your scaling success, we can also empathize with her feeling like too much of a control freak (her words, not ours) to make the best decision. So how do you start hiring without losing control of the most important aspects of your company? It’s a t...
Oct 08, 2020•35 min•Season 9Ep. 2
On today’s episode, we have a coaching call with Ignacio, who’s building a growing web design business in Guatemala. Ignacio’s business is doing well, but he knows if he wants to go from freelance to founder, he needs to get more organized. So in today’s call, we coach Ignacio through how to organize his multiple brands, how to pick the perfect project management tool, and how to get his clients to pay more. If you’re ready to get your business in order so you can crush Q4 and hit the ground run...
Oct 01, 2020•47 min•Season 9Ep. 1
On today’s episode (the final episode in our eighth season) I want to turn the tables and share with you an interview I did with my friends Marc and Julia at The Clearing. I’ve done dozens of interviews over the years, but Marc seems to ask the perfect questions in this interview—leading to one of the best conversations on freelancing I’ve ever had on the air. We discuss getting freelance jobs, what to focus on when building a portfolio, how to build passive income, and lots more. In fact, Marc ...
Jul 30, 2020•50 min•Season 8Ep. 17
Do you ever get the feeling you're attracting the wrong kinds of clients for your freelance business or agency? Today's guest faces the same question: "how can I turn down clients who aren't a good fit?" Paul Chris Luke spent his first few years out of college working at an agency doing digital marketing. But then he decided to leave it all behind, sell his house and most of his possessions and move to Cambodia—a place he’d never even been. After taking a year off to reflect on where his life wa...
Jul 23, 2020•57 min•Season 8Ep. 16
Imagine catching the coronavirus and losing half of your clients in less than 48 hours. That's what happened to today's guest, Jim Huffman. Jim runs GrowthHit, a conversion-focused agency serving tech companies and startups. When Covid-19 hit the U.S. in March of this year, Jim got an email from one of his clients asking to put their work “on hold”—which was all fine and well until another client cut them off….and another… and another. The pandemic had led to Jim’s company losing almost half a m...
Jul 16, 2020•57 min
