Freelance to Founder

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. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → ⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → ⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 reveals how eliminating one major client bottleneck doubled his revenue. If you've been following someone else's blueprint and feeling like an imposter, this conversation will give you permission to build a business that actually lights you up. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → ⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 move the needle for YOUR business, not someone else's. If you've been stuck in analysis paralysis while your marketing sits on the back burner, this episode will give you permission to start small, focus strategically, and build momentum without burning out. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → ⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 full of strangers. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 systems, and why defining roles before deploying tools is the secret to avoiding the productivity trap that kills so many growing businesses. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about guest co-host, Christine → ⁠https://www.linkedin.com/in/colivas/⁠ — ⁠https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 reframing the handoff process from loss to gain. If you're struggling with letting go while scaling up, this conversation will help you move forward with confidence. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about guest co-host, Christine → ⁠https://www.linkedin.com/in/colivas/⁠ — ⁠https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

You've made your first couple of hires—congrats! But now comes the tricky part: how do you price your services high enough to pay your team well, while still remaining competitive enough to win clients? In this episode, Preston and Christine Olivas tackle the delicate balancing act of agency pricing, exploring the two-sided marketplace challenge of keeping both clients and team members happy. From identifying premium clients to articulating your unique value proposition, this conversation reveals why pricing isn't just about numbers—it's about positioning yourself in the right league. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about guest co-host, Christine → ⁠https://www.linkedin.com/in/colivas/⁠ — ⁠https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

You're swamped with client work, staying up late to meet deadlines, and turning down opportunities because you simply can't handle more. Sound familiar? In this episode, Preston and Christine Olivas tackle one of the biggest transitions in a freelancer's journey: knowing when—and how—to hire your first contractor. Christine shares her experience growing from solo freelancer to running a 24-person operation, revealing why volume of work alone isn't the right reason to hire, and how choosing between "deliverable hires" and "business hires" can determine whether you build real freedom or just create another job for yourself. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about guest co-host, Christine → https://www.linkedin.com/in/colivas/ — https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices