Freelance to Founder-logo

Freelance to Founder


Clay and Preston have each grown their own one-person businesses to something much bigger and now they offer weekly coaching calls with freelancers ready to do the same. Your weekly dose of real-world, practical, actionable advice to take your service-based business to the next level—with occasional surprise guest experts or deep dives on must-have skills for success. New shows every Thursday.

Clay and Preston have each grown their own one-person businesses to something much bigger and now they offer weekly coaching calls with freelancers ready to do the same. Your weekly dose of real-world, practical, actionable advice to take your service-based business to the next level—with occasional surprise guest experts or deep dives on must-have skills for success. New shows every Thursday.


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Clay and Preston have each grown their own one-person businesses to something much bigger and now they offer weekly coaching calls with freelancers ready to do the same. Your weekly dose of real-world, practical, actionable advice to take your service-based business to the next level—with occasional surprise guest experts or deep dives on must-have skills for success. New shows every Thursday.








Close 90% of Clients (without Proposals)

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...


Coaching at Scale

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...


How to Speak Your Clients' Language

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...


Should You Branch Out or Niche Down?

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...


Do You Have the Wrong Target Audience?

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...


You've Been Lied to About "Work/Life Balance"

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...


Do Clients Treat You Like an Expert? or Employee?

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...


Collabs vs. Hiring

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...


12 Mo. of Revenue in 30 Days

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...


Less Convincing, More Closing.

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...


Are You Stuck in "Create" Mode?

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...


3 Ways to "Spy" on Your Ideal Client

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...


Leader vs. Entrepreneur

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...


Are You Optimizing for Profit?

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...


Getting Out of Your Own Way

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....


Will Clients “Subscribe” to Freelancing?

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...


Make Art, Make Money

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...


Working From Anywhere (Remote Works Podcast Sneak Peek)

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...


The Truth About Being a ‘Founder’

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...


Giving Yourself a $40K Raise + Investing in People

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...