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.








Getting Clients on LinkedIn

With millions of potential clients spending time on Linkedin, it's worth learning how to get it right. Today, we share our top tips for getting clients through LinkedIn. On today’s show, we have a coaching call with side-hustler Corey who’s building a web design business for physical therapists and other health professionals. Among other things, we end up talking in-depth about using Linkedin to get more clients. Our guest co-host and my friend Chelsea Baldwin and I share some of our...


Growing Beyond Job Sites

Freelance job sites are a great way to get your foot in the door as a freelancer. But are they the best long-term strategy for growing an agency? On today’s show, we have a coaching call with Ron, who has been freelancing on Fiverr for over 10 years—and he’s done quite well for himself. Ron gets a ton of new business from Fiverr, but he’s worried about two things: first, it can be difficult to build long-term relationships with clients on Fiverr and second, if there was an algorithm...


Does Client-Hunting Keep You from Scaling?

New clients are often the lifeblood of a freelance business, but what if taking on new work is holding you back from growing your business? On today’s show, we give some coaching to Will Gibbons—a product rendering expert who works with huge brands like Pelaton, 3M, Vizio and more. After a year of freelancing, Will is facing perhaps one of the best problems you can ask for: He’s got too many client requests coming in and too much work that needs done. So in this episode, Clay and I walk him...


Can You Win at Business ... Without Burning Out?

On today’s show, we have a conversation with Corbett Barr from Corbett has had a huge impact on my life and business and, after a recent conversation with Clay about hustling and burning out, I knew I had to introduce them. That’s because Corbett is one of my favorite thinkers when it comes to balancing life with the hustle of entrepreneurship. Corbett’s insights lead us down a path answering questions like: what am I giving up by hustling all the time? Do I really need to...


How to Unlock a Floodgate of Client Leads

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 working at about 20% capacity, and a desire to grow, she’s in a perfect place to make fast...


Getting More Clients (as an Introvert)

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 up some good relationships and they have the beginnings of a solid client base. But, as any...


Introducing 'Creative Elements'

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 business from their creativity. He’s had conversations with legendary marketer Seth Godin,...


3 Ways to Finally Raise Your Prices

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 to scale. Clay and I are up to the challenge as we spend the full second half of the episode...


Should You Do Your Own Marketing?

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 common question for service-based businesses: should you focus on doing the work for current clients...


Revenue on Autopilot—Is It Really Possible?

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—without really any work at all. Throughout the episode, I share how I’ve outsourced most of my daily...


Getting Press as a Freelancer (from the Editor of Entrepreneur Mag)

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 conversation chatting about the current state of freelancing and the future of freelancing in a...


Are You Attracting the Wrong Clients?

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 to attract my ideal client?" We walk her through a few key social media strategies that’ll also...


Unleashing the Power of Local Clients

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...


Hiring 50 Contractors in a Year (Whew!)

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...


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...