Freelance to Founder

On today’s episode, Caroline calls in from one of my favorite places on Earth: the Netherlands. Caroline is building a graphic and web design business and has already hired quite a few contractors. She gets a decent amount of work every month, but each new month leaves her with the frightening question: Will we get enough new business this month? With some good lead generation in place, a team wor...

On today’s show, I’m joined again by my friend Matt Olpinski for our coaching call with side-hustler-turned agency-builder Jason Frostholm. After working on the side for years, Jason and his wife finally decided to take their freelancing full-time and build an agency together. That was right before the global pandemic. Now, after a year of eating into savings, they’ve used word-of-mouth to build u...

After working with creatives for 10+ years, Clay and I know it can be hard making a living from your art and creativity. If your creative business needs a little boost, I suggest you listen to Creative Elements—a really great podcast from my friend Jay Clouse. Creative Elements is a highly produced narrative-interview show where Jay talks to high-profile, successful creators about how they built a...

Today we have a coaching call with Joseph, a digital nomad working in Mexico. Joseph is building his Wordpress development company on the side of his day job with dreams of becoming a full-time entrepreneur. But there’s one major thing standing in Joseph’s way. As you’ll hear him explain during the show, Joseph is charging what he calls “employee” prices which just doesn’t give him enough cashflow...

Today’s coaching call is with Andy who’s calling in from Colorado, USA. And while Andy runs a business that Clay and I know virtually nothing about, he’s facing a question we have lots of answers to: Should Andy do his own marketing? He’s already working 40-50 hours a week in his business and he’s trying to figure out who to hire next, where to find them, and what tasks to assign them. It’s a comm...

Have you ever found yourself approaching burnout in your business and wondered: is there any way to generate revenue on autopilot? On this episode, Clay and I hit record on a rather personal conversation we were having about our businesses. The question is: can we make enough money on autopilot to finance a nice lifestyle without having to put in long hours every single week or—as Clay hopes—witho...

On today’s episode Clay and I are joined by the editor of Entrepreneur Magazine, Jason Feifer to talk about how to get press for your freelance business. Whether you want to get more visibility to your brand or attract new clients using earned media, this conversation with Jason will give you actionable, real-world advice on getting featured by journalists and influencers. We also kick off the con...

On today’s show, we talk with Mannat, a student calling from India with questions about her freelance business. Mannat is a typographer—she works with lettering and fonts. But everytime Mannat posts her work to social media, she gets packaging design clients and others reaching out who just don’t match her target audience. This leaves Mannat asking “what exactly should I be posting on social media...

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...

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...

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...

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 o...

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 m...

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 a...

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....

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 balanc...

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 men...

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,...

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 Ja...

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 realiz...

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 dur...

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 f...

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 n...

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 infrastru...

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 overthin...