Freelance to Founder Podcast Art

Real freelancers. Real growth.

Freelance to Founder is a unique weekly podcast featuring coaching calls co-hosted by Clay and Preston, two freelancers-turned-business-builders. Instead of typical interviews, each week a new freelancer calls in to talk with Clay and Preston with one goal in mind: overcoming the feast/famine cycle and scaling their service business. The highly acclaimed, top-rated podcast is a weekly dive into what it really takes to go from freelance to founder.

In partnership: Millo, Dripify, Podglomerate

New shows every Thursday. Subscribe with your favorite.

S13 E7 — 63 min

Charge Like a Founder—Not an Employee

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 duri ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG1490347720.mp3?updated=1637857451 Charge Like a Founder—Not an Employee

S13 E6 — 56 min

When You're Too Busy to Scale

On today’s episode, we have a great conversation with Will Gibbons—a product rendering guru who works with huge brands like Pelaton, 3M, Vizio and more. After a year of working for himself, Will is facing perhaps one of the best problems you can ask for as a freelancer: He’s got too many clien ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG7783921877.mp3?updated=1637139421 When You're Too Busy to Scale

S13 E5 — 53 min

Crushing it with Cold Outreach

On today’s episode, we have a coaching call with Mohcine who’s building a facebook ads business from Morrocco. Mohcine has had some great success getting jobs on Upwork, but he’s ready to diversify his marketing and has decided to go with cold outreach for starters. Clay and I give Mohcine eno ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG6504156821.mp3?updated=1637139462 Crushing it with Cold Outreach

S13 E4 — 53 min

If We Had to Start Over from Scratch...

Today, I (Preston) got a text from Clay. "I just let my entire team go." It took me completely by surprise, but also got me thinking about what it would take to start all over. On today’s episode, Clay and I answer the question: “what would we do differently if we had to start freelancing from s ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG1129756761.mp3?updated=1637138915 If We Had to Start Over from Scratch...

S13 E3 — 55 min

Getting Clients to Trust Your Team

On today’s show, we’re joined by Chad who’s working on building his agency in Utah, USA. Chad works with clients all over the world. They hire him because they like and trust him.  But now, Chad is beginning to hire some freelancers to help get the work done in his business and he's wondering ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG9182350650.mp3?updated=1637138750 Getting Clients to Trust Your Team

S13 E2 — 66 min

Filling Your Lead Generation Gap

On today’s show, we chat with Kendrick who is building a video production agency in Atlanta, Georgia, USA.  Kendrick’s a talented videographer with a highly-skilled team, but he’s feeling stuck when it comes to building a process to generate new business on a regular business. Kendrick and h ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG6311514886.mp3?updated=1637138672 Filling Your Lead Generation Gap

S13 E1 — 58 min

The Power of Personal Brand

On today’s episode, we have a coaching call with Denise, a freelancer from South Carolina, USA.  Denise works in higher education and is happy with the way her freelance business is going. But after finding some early success in e-learning thanks to Covid and other factors, Denis is ready to bran ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG4532803481.mp3?updated=1637140896 The Power of Personal Brand

S12 E12 — 51 min

A Flood of Questions (Can We Keep Up?)

On today’s show, our guest Nouman slams us with more questions than any guest before and we do our best to deliver some good answers. Nouman has quickly grown his agency from 3 partners to over 20 employees in just a couple years. But most of Nouman’s clients still come from Upwork or Fiverr an ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG6141181027.mp3?updated=1637138348 A Flood of Questions (Can We Keep Up?)

S12 E11 — 51 min

Are High-Ticket Clients Enough?

On today’s show, we have a conversation with Rachel Cooke who designs high-ticket training experiences for massive clients. Rachel’s business is doing well. She’s happy with the amount of money she’s making and where her business is headed.  But she doesn’t necessarily like the fluctuatio ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG9837945102.mp3?updated=1632863314 Are High-Ticket Clients Enough?

S E — 25 min

Should Managers Code?—Introducing 'Compiler', an original podcast from Red Hat

To listen to more episodes or subscribe to Compiler, click here. Technology can be bold. But it can also be complicated. Compiler breaks down the big questions about tech and the tech industry in this new original podcast. On today's bonus episode, I share with you a brand new podcast called 'Compil ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG9566906068.mp3?updated=1632337429 Should Managers Code?—Introducing 'Compiler', an original podcast from Red Hat

S12 E10 — 42 min

The Freedom of Being "Out of the Loop"

Looping yourself out of every aspect of your business can be a bit terrifying. But it's also incredibly liberating. Hear why on today's show. On today’s show, I talk with Joe Babi who’s building his own SEO agency. Not long ago, Joe found himself overworked and missing out on important life even ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG3928038816.mp3?updated=1637138179 The Freedom of Being "Out of the Loop"

S12 E9 — 53 min

Getting Agency-Quality Leads (w Big Budgets)

How can you get agency-level leads (big budgets, long timelines) when you're just a freelancer? On today’s show, we chat with Ilias a Shopify developer from Morocco. Ilias has been freelancing for over two years and thinks it might be time to move from freelancing to building an agency. He hits us ....

Listen Now https://pdst.fm/e/chtbl.com/track/4G278/traffic.megaphone.fm/TPG1381152146.mp3?updated=1637138137 Getting Agency-Quality Leads (w Big Budgets)

Show all episodes

Free on-air business coaching for freelancers.

On this show, real-life freelancers get 100% FREE on-air coaching to help them scale their business. And we want to chat with you!

Here's how to get on the show:


1. Book a time

Choose a time to get your free on-air business coaching to be included in an upcoming episode.


2. Tell us more

Tell us more about your business and your future goals by filling out this questionnaire.


3. Get ready

We'll email all the details you need to join us on the air. We can't wait!

Please select an episode...
00:00 00:00