Freelance to Founder

By MilloBusiness Entrepreneurship Education Self-Improvement

Freelance to Founder episodes

November 02 How to Vet Network Groups Before Joining
Tired of networking groups that feel more like spam factories than genuine connection opportunities? In this episode, Clay breaks down the art of finding professional groups that actually deliver value, sharing insider tips from his own successful agency-building journey.
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19 min
October 30 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 dynamics of managing client relationships when unexpected stakeholders enter the scene. Whether you're a freelance designer, consultant, or creative professional, you'll want to hear our strategies for navigating these delicate professional waters.
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13 min
October 29 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 finding the perfect software, but something else entirely.
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17 min
October 28 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 she's about to lose a valuable client. But here's the thing: the disaster she's imagining might only exist in her head.
In this episode, Clay and Preston tackle the all-too-common problem of freelancers building up worst-case scenarios before anything bad actually happens. They break down why you should send that invoice, how to handle pushback if it comes, and why the story you're telling yourself is probably far worse than reality. If you've ever hesitated to bill a client for work you've done, this episode will give you the confidence to stop panicking and start acting.
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15 min
October 27 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 lead Preston and Clay to tackle the counterintuitive truth about sales, retention, and positioning—revealing why individuals often win deals faster, but teams keep clients longer. Whether you're debating growing your team or staying solo, this discussion will help you understand which approach actually attracts the clients you want (and why the answer isn't what you might expect).
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25 min
October 26 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 them over. Should you push back, charge for the files, or just let it go? In this episode, Preston and Clay tackle Kevin's dilemma about whether to fight for those source files or take the high road. Their advice might surprise you: sometimes the smartest business move is the one that feels like you're giving something away for free.
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16 min
October 23 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 overwhelming? You're not alone. In this episode, Rachel asks how to reconnect with her passion for her business when the hustle feels exhausting. Preston and Clay dive deep into why we lose motivation, the importance of slowing down, and how to give yourself permission to coast without guilt. This is a conversation every entrepreneur needs to hear—because your mental health matters more than your growth metrics.
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15 min
October 22 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 harder than it sounds. How do you train team members to run with tasks independently without constant check-ins? How do you avoid becoming a bottleneck that slows everyone down? And how do you set boundaries without seeming hostile or unavailable? In this episode, Preston and Clay answer listener Peter's question about delegation, drawing on Clay's experience managing a 20+ person team generating over a million in recurring revenue. They share practical strategies for creating SOPs, setting communication boundaries, and hiring people who can actually think for themselves—so you can focus on growing your business instead of micromanaging every detail.
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Check out Clay's business → ⁠⁠https://golinus.com

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21 min
October 21 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 fee? Or simply say no? In this episode, Preston and Clay tackle listener Kirsten's question about handling urgent client requests outside business hours. They break down when to charge rush fees, how to set boundaries without damaging relationships, and why communication is the secret weapon for managing client expectations.
If you've ever felt pressured to work weekends or evenings because a client needed something "right now," this conversation will help you draw the right lines while still being a great service provider.
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Check out Clay's business → ⁠⁠https://golinus.com

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15 min
October 20 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 might be asking the wrong question entirely. In this episode, Preston and Clay dive deep into pricing strategy with a question from Lanya, revealing why hourly pricing punishes you for being good at what you do—and introducing the game-changing concept of value-based pricing. Learn how to have conversations with clients that uncover the true worth of your work, why asking about impact matters more than counting hours, and how solving a $300,000 problem for $10,000 isn't sleazy—it's simply understanding your value.
Support our show sponsors → https://freelancetofounder.com/sponsors
Submit your own question → https://freelancetofounder.com/ask
Check out Clay's business → ⁠⁠https://golinus.com

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18 min