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Freelance to Founder

Millo

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...

Episodes

20 of 673 episodes

How to Handle Interfering Spouse

What happens when a client's spouse starts meddling in your carefully crafted design process? In this episode, we dive deep into the tricky...

12:15Oct 30, 2026

Drowning in Client Paperwork?

Drowning in proposal and contract paperwork? Clay and Preston reveal the surprising truth about client management tools—it's not about findi...

16:26Oct 29, 2026

Scared to Invoice for Extra Work...

Have you ever sent a proposal, completed extra work, and then panicked about sending the invoice? Laura did exactly that—and she's convinced...

14:57Oct 28, 2026

Will You Get More Clients as a Freelancer or Agency?

Is it just me, or does it seem easier to close a sale when you're a freelancer than as a full agency? Amy Bridges asked this question which...

24:34Oct 27, 2026

Past Client Wants Source Files. Now What?

An old client from two years ago wants the original design files from a past project—but you're worried about losing future work by handing...

15:10Oct 26, 2026

Put Your Business in Airplane Mode

Feeling burned out on the business side of freelancing? You still love the creative work, but networking and client acquisition feel overwhe...

14:57Oct 23, 2026

You're Not Bad at Delegating. You're Bad at Hiring.

As your freelance business grows, you hit an inevitable ceiling: there's only so much you can do yourself. But delegating effectively is har...

20:40Oct 22, 2026

5:22 PM on a Friday and Your Client Calls...

It's 5:22 PM on a Friday, and a client emails asking if you can design an ad tonight. Do you drop everything and work late? Charge a rush fe...

14:02Oct 21, 2026

For Hourly Rates, This is Your Punishment

Should you charge by the hour or by the project? If you've ever struggled with this question, you're not alone. But here's the truth: you mi...

17:34Oct 20, 2026

Pressure to Be a Marketer?

Feeling pressured to add marketing services to your web design business just because a course told you to? In this episode, Preston and Clay...

22:39Oct 19, 2026

Pick a Tactic... Any Tactic.

Feeling paralyzed by the endless stream of marketing tactics you "should" be doing? You're not alone. In this episode, Matt from Barrow Stud...

22:33Oct 16, 2026

Introverts Can Become Millionaires

Feeling nervous about networking? You're not alone. In this episode, Brittany asks how to break into local networking as a shy person, and C...

22:15Oct 15, 2026

Fire Your Inbox

As your freelance business grows from solo operator to team leader, the chaos can hit fast. Emma Clark's question about transitioning from i...

24:07Oct 14, 2026

Your Client Hired YOU. Can you hand off?

Omar's business is growing, and so is his workload. His longtime clients love working with him, which is the problem. As he builds Vision Cr...

22:16Oct 8, 2026

What's Your Cut When You Hire Help?

Layla built Bright Horizon Media from the ground up, and now her social media agency has a team and real momentum. Her next challenge is spl...

24:22Oct 7, 2026

Your First Hire Could Save You… or Sink You

Christine Olivas has a calendar that won't quit and a pile of projects she keeps saying no to. The obvious move is to hire, but she knows th...

21:36Oct 6, 2026

Do Clients Actually Care If You're an "Expert"?

CodeCrafter's skills are solid and his work speaks for itself, but he keeps holding back. Charging more feels presumptuous, and calling hims...

15:01Oct 5, 2026

Is Subcontracting Quietly Erasing Your Business?

Garrett is a 30-year-old nonprofit consultant doing great work for a seasoned consultant. The problem is that almost nobody knows it's his w...

13:44Oct 2, 2026

Should You Go For Giant Projects?

A solo designer finally gets the call from a big-name client, and it's the kind of project that could turn a freelance business into a real...

19:30Oct 1, 2026

Non-US Freelancer: Roadblock or Excuse?

Dieter is weighing a big question from his home base in Europe: is it worth going after US clients at all, or is he fighting a battle he can...

18:40Sep 30, 2026