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PODCAST

Freelance to Founder

Freelance to Founder is a call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle. The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own. Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level. You can submit your questions at FreelanceToFounder.com/ask If you enjoy content from

business

All Episodes

20:18

Stuck with Low-Paying Clients? Here's the Fix...

Freelance to Founder ·

2025/11/01

Preston and AJ dive deep into strategies that will help you break free from the local client trap and attract high-value, premium international clients. Learn proven tactics for transforming your outreach, positioning your agency, and landing the clients you deserve.Links: Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with AJ

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18:10

Can You Raise Rates w/out 'Scaring' Away Clients?

Freelance to Founder ·

2025/10/31

Preston and guest AJ Cassata dive deep into the art of pricing, revealing how freelancers can confidently raise their rates without losing momentum. Learn the counterintuitive strategies that can help you attract better clients, work less, and earn more. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with AJ -> https://www.youtube.com/@ajcassataofficial https://www.linkedin.com/in/ajcassata/ Learn

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16:07

Is "Find a Niche" Outdated Advice?

Freelance to Founder ·

2025/10/30

In this episode of Freelance to Founder, we dive deep into the art of finding your niche, exploring practical strategies for designers and content creators navigating the complex world of freelance work. Preston and Christine break down the myths about specialization and offer invaluable insights for finding your unique professional path. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad

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15:06

Charge More (Yes, Really)

Freelance to Founder ·

2025/10/28

Are you a freelancer struggling with the nerve-wracking task of increasing your prices? In this eye-opening episode, Preston Lee and guest host Christine Olivas dive deep into the art and science of rate increases, offering invaluable insights for freelancers at any stage of their career. Whether you're battling imposter syndrome or wondering if your rates truly reflect your worth, this episode is your roadmap to confident pricing. Links: Support our show sponsors ->

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16:28

Is Your Portfolio Broken?

Freelance to Founder ·

2025/10/27

It can be a real challenge to create a portfolio that actually converts new clients. This episode of Freelance to Founder dives deep into creative ways to showcase your professional expertise, even when you're new to the freelance world. Preston Lee and Christine Olivas share insider tips on how to build a compelling portfolio that attracts clients and demonstrates your value. Links: Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question ->

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17:32

Find Networking Groups That Don't Suck

Freelance to Founder ·

2025/10/23

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.Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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11:45

Spouse Making Trouble

Freelance to Founder ·

2025/10/22

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. Support our show sponsors: https://freelancetofounder.com/sponsors Submit your own question:

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15:56

Best Proposal & Contract Tool?

Freelance to Founder ·

2025/10/21

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. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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14:27

Did I Just Lose Money?

Freelance to Founder ·

2025/10/20

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,

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24:04

Is It Just Me? Or...

Freelance to Founder ·

2025/10/17

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

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14:40

Should I Fight This?

Freelance to Founder ·

2025/10/16

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.Support our show sponsors →

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14:27

Mental Health > Hustle Culture

Freelance to Founder ·

2025/10/15

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

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20:10

NEW: Why Delegating Isn't Working

Freelance to Founder ·

2025/10/14

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

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13:32

NEW: Rush Fees: A Trap or a Bonus?

Freelance to Founder ·

2025/10/13

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

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17:04

The Secret Weapon of Pricing

Freelance to Founder ·

2025/10/10

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,

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22:09

NEW: Do I HAVE to Be a Marketer?

Freelance to Founder ·

2025/10/09

Feeling pressured to add marketing services to your web design business just because a course told you to? In this episode, Preston and Clay challenge the "supposed to" mentality that keeps freelancers stuck offering services they don't enjoy. Erica, a web designer, asks how to balance project work she loves with repetitive marketing tasks she wants to outsource—but the answer might surprise you. Clay shares his game-changing monthly recurring revenue model for websites (no contracts required!) and

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22:03

NEW: What's the Marketing "Silver Bullet"?

Freelance to Founder ·

2025/10/08

Feeling paralyzed by the endless stream of marketing tactics you "should" be doing? You're not alone. In this episode, Matt from Barrow Studio asks the question every service business owner wrestles with: with so many marketing strategies out there—from email lists to podcasts to paid ads—where should you actually focus your limited time and resources? What's the "silver bullet"? Clay and Preston cut through the noise with a refreshingly simple framework that helps you identify what will actually

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21:45

NEW: Am I Too Shy to Network?

Freelance to Founder ·

2025/10/07

Feeling nervous about networking? You're not alone. In this episode, Brittany asks how to break into local networking as a shy person, and Clay shares exactly how he built a million-dollar agency through local connections—even as a total introvert. From joining your first chamber event to creative strategies that put you front and center without the awkward sales pitch, this episode is packed with actionable steps for anyone who wants to grow their business locally but dreads walking into a room

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23:37

NEW: There Must Be a Better Way

Freelance to Founder ·

2025/10/06

As your freelance business grows from solo operator to team leader, the chaos can hit fast. Emma Clark's question about transitioning from inbox management to real systems is one every growing freelancer faces. In this episode, Preston and Christine Olivas dive deep into the practical side of scaling—revealing why your tool choice matters less than you think, and what actually needs to happen first. Christine shares how her team of 24-28 people stays incredibly agile using surprisingly simple

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21:46

NEW: Please Don't Kill My Baby...

Freelance to Founder ·

2025/10/03

You've built incredible relationships with your clients as a freelancer—but now that you're growing into an agency, how do you transition them to work with your team without losing the trust you've worked so hard to earn? In this episode, Preston sits down with Christine Olivas, founder and CEO of No Single Individual, to tackle this exact challenge. Christine shares her insights on finding team members who reflect your values, understanding what clients truly value about working with you, and

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