Freelance to Founder

Breaking free from the day-to-day grind isn't just a dream—it's a strategic necessity for freelancers and small business owners looking to transform their work. In this episode, Preston and Vijay Rajendran dive deep into how to create a meaningful vision and actionable roadmap for your business, offering insights that go far beyond traditional growth strategies. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Vijay -> ⁠⁠StartupSystem⁠⁠  | ⁠⁠Read My Book⁠⁠ | ⁠⁠Follow me on Substack⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelance writing can feel like a financial rollercoaster, with many creators struggling to price their services confidently. In this revealing conversation, Preston and Amy Suto crack open the complex world of freelance pricing, sharing hard-earned strategies that transform how independent professionals value their work. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Amy -> Book: ⁠https://amysuto.com/power⁠ Website: ⁠https://MakeWritingYourJob.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing offers incredible freedom, but it can also lead to overwhelming stress and exhaustion. Many freelancers find themselves trapped in a cycle of constant work, juggling client demands, marketing efforts, and administrative tasks. But it doesn't have to be this way. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Amy -> Book: ⁠https://amysuto.com/power⁠ Website: ⁠https://MakeWritingYourJob.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

The world is transforming FAST, but creative professionals aren't going extinct—they're evolving. In this eye-opening episode, Preston and Amy Suto dive deep into how freelancers can not just survive, but truly thrive in the age of AI, revealing surprising opportunities for those willing to adapt and specialize. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Amy -> Book: https://amysuto.com/power Website: https://MakeWritingYourJob.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Feeling overwhelmed by the endless tasks of running a solo business? You're not alone. In this episode of Freelance to Founder, Preston and guest Amy Suto dive deep into practical strategies for automating your workflow, saving time, and protecting your mental energy. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Amy -> Book: ⁠https://amysuto.com/power⁠ Website: ⁠https://MakeWritingYourJob.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Delegation is the critical skill that separates struggling freelancers from successful business founders. In this episode, Preston Lee and Vijay Rajendran break down the complex art of managing subcontractors, offering a roadmap for entrepreneurs who find themselves constantly fixing mistakes and feeling overwhelmed. Learn how to transform your leadership approach from constant oversight to strategic team development. This episode provides practical insights that can help you build a more efficient, scalable business by mastering the nuanced art of delegation. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Vijay -> ⁠StartupSystem⁠  | ⁠Read My Book⁠ | ⁠Follow me on Substack⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Growing your freelance business often means taking on larger projects that require collaboration. But how do you successfully manage a team when you've been a solo operator? In this episode, Preston Lee and special guest Vijay Rajendran dive deep into the art of building and leading your first team project, offering invaluable insights for freelancers ready to level up their business. Vijay Rajendran brings a wealth of experience from venture capital, startup coaching, and founding multiple businesses to provide a nuanced approach to team building that goes far beyond traditional hiring practices. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask Connect with Vijay -> StartupSystem  | Read My Book | Follow me on Substack Learn more about your ad choices. Visit megaphone.fm/adchoices

Feeling uncomfortable promoting your business? You're not alone. Many freelancers struggle with the fine line between effective self-promotion and feeling like a pushy salesperson. In this episode, Preston Lee and George Azar dive deep into strategies for marketing your services genuinely and confidently. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with George -> ⁠https://brightbudget.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Navigating the world of business taxes can feel like walking through a minefield of conflicting advice and flashy marketing promises. In this eye-opening episode, Preston and George Azar pull back the curtain on S-Corp elections, revealing the nuanced truth behind those tantalizing internet ads claiming massive tax savings. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with George -> ⁠https://brightbudget.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Managing finances can make or break a freelance business. In this episode, CPA George Azar breaks down the critical decisions around tracking your money – from simple spreadsheets to professional bookkeeping services. If you're wondering whether it's time to upgrade your financial tracking, this episode offers practical insights that could save you time, stress, and potentially money. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with George -> https://brightbudget.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing offers incredible freedom, but it also comes with financial uncertainty. If you've ever stressed about managing your money when paychecks vary from month to month, you're not alone. In this episode, Preston and George dive deep into practical strategies for creating a solid financial foundation, even with an unpredictable income stream. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with George https://brightbudget.com/ https://www.youtube.com/@BrightTaxTalk Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing can be challenging, especially when clients expect ongoing work without additional compensation. In this episode, Preston and Chanda Coston dive deep into a common freelancer dilemma: how to handle clients who continuously ask for small free favors after a project is completed. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Chanda Instagram, Facebook & TikTok: @chanda__co LinkedIn: ⁠linkedin.com/in/chandacoston⁠ 1:1 $21 Tiny Challenge ⁠https://join.chanda-co.com/home-page-page Learn more about your ad choices. Visit megaphone.fm/adchoices

Switching from hourly to flat rate pricing can feel like navigating a minefield for freelancers. In this episode, Preston and Chanda break down the strategies that will help you confidently transition your pricing model, protect your revenue, and position your services as a premium offering that clients will love. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Chanda Instagram, Facebook & TikTok: @chanda__co LinkedIn: ⁠linkedin.com/in/chandacoston⁠ 1:1 $21 Tiny Challenge ⁠https://join.chanda-co.com/home-page-page Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing offers freedom, but it can also bring financial uncertainty—especially when clients drag their feet on payments. In this episode, Preston and Chanda dive deep into a common freelancer nightmare: managing clients who consistently pay late while trying to maintain a healthy, stress-free business. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Chanda Instagram, Facebook & TikTok: @chanda__co LinkedIn: ⁠linkedin.com/in/chandacoston⁠ 1:1 $21 Tiny Challenge ⁠https://join.chanda-co.com/home-page-page Learn more about your ad choices. Visit megaphone.fm/adchoices

Every freelancer faces moments of financial uncertainty. When bills are mounting and opportunities seem scarce, the temptation to accept low-paying work can feel overwhelming. But is compromising your rates really the smart move for your business? In this eye-opening episode, Preston and guest Chanda Coston dive deep into the critical question: Is it ever smart to take on low-paying clients just to fill an income gap? Their insights will help you make financially savvy decisions that protect your business's future. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Chanda Instagram, Facebook & TikTok: @chanda__co LinkedIn: linkedin.com/in/chandacoston 1:1 $21 Tiny Challenge https://join.chanda-co.com/home-page-page Learn more about your ad choices. Visit megaphone.fm/adchoices

Struggling to grow your freelance business and attract quality clients? In this episode of Freelance to Founder, Dr. Noah St. John breaks down his proven MAPSSS method for generating leads that can transform your business from a side hustle to a thriving agency. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Noah -> ⁠https://noahstjohn.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Breaking free from self-imposed limitations isn't just about willpower—it's about understanding the deep-rooted habits that keep you stuck. In this eye-opening episode, Dr. Noah St. John reveals the psychological mechanisms behind procrastination, fear, and success, offering freelancers a transformative roadmap to move from survival mode to founder status. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Noah -> https://noahstjohn.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing promises freedom, but the path to steady income can feel uncertain. In this episode, Preston and Meredith dive deep into the strategies that help freelancers build a reliable revenue stream, sharing practical insights from their own experiences of transitioning from uncertain earnings to a stable business model. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Meredith: Website: ⁠⁠www.pageandpurpose.com⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/meredith-rice-cooley/⁠⁠ ⁠⁠Free Weekly Resource on how to make the jump from Teaching to Copywriting Learn more about your ad choices. Visit megaphone.fm/adchoices

Embarking on a freelance journey can feel like navigating uncharted waters. Many aspiring freelancers get stuck in the preparation phase, overthinking branding, websites, and perfect portfolios instead of taking the most crucial first step: getting clients. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Meredith: Website: ⁠⁠www.pageandpurpose.com⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/meredith-rice-cooley/⁠⁠ ⁠⁠Free Weekly Resource on how to make the jump from Teaching to Copywriting Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing isn't just about the work you do—it's about understanding yourself, managing your time, and staying flexible. In this episode, Preston Lee and Meredith Cooley dive deep into the most valuable lessons they've learned while building their freelance businesses, offering insights that go far beyond simple tactics and touch on the personal growth required to truly succeed as an entrepreneur. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Meredith: Website: ⁠www.pageandpurpose.com⁠ LinkedIn: ⁠https://www.linkedin.com/in/meredith-rice-cooley/⁠ ⁠Free Weekly Resource on how to make the jump from Teaching to Copywriting Learn more about your ad choices. Visit megaphone.fm/adchoices

Dreaming of launching a freelance business while working full-time can feel overwhelming. What if you could strategically carve out time, optimize your schedule, and build momentum without burning out? In this episode, former teacher turned copywriter Meredith Cooley shares her proven strategies for transforming side hustle aspirations into reality. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Meredith: Website: www.pageandpurpose.com LinkedIn: https://www.linkedin.com/in/meredith-rice-cooley/ Free Weekly Resource on how to make the jump from Teaching to Copywriting Learn more about your ad choices. Visit megaphone.fm/adchoices

Breaking into freelancing can feel like an impossible challenge when you're just starting out. But what if landing your first client is simpler than you think? In this episode, Preston and AJ Cassata dive deep into practical strategies for new freelancers looking to secure their inaugural client, sharing personal stories and actionable advice that can transform your freelance journey. 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 more about your ad choices. Visit megaphone.fm/adchoices

Freelancing offers freedom, but it can also lead to working more hours than ever before. In this episode of Freelance to Founder, Preston and AJ dive deep into a listener's struggle with time management, offering practical strategies for freelancers feeling overwhelmed and overworked. 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 more about your ad choices. Visit megaphone.fm/adchoices

Freelancing can feel like riding a rollercoaster of unpredictability. One moment you're scrambling for leads, the next you're buried under a mountain of projects. In this episode, Preston and AJ dive deep into practical strategies for stabilizing your freelance business, transforming sporadic opportunities into a consistent, sustainable income stream. 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 more about your ad choices. Visit megaphone.fm/adchoices

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 -> https://www.youtube.com/@ajcassataofficial https://www.linkedin.com/in/ajcassata/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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. [Links] 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

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 choices. Visit megaphone.fm/adchoices

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

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 -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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: https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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. 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

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). 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

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 → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices

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. 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

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

Feeling like you're not skilled enough to start freelancing or to grow your agency? You're not alone. In this episode, Preston tackles one of the biggest mental barriers new freelancers face: imposter syndrome. CodeCrafter asks how to build confidence when you don't feel expert enough—and Preston's answer might surprise you. Turns out, you don't need to be the world's best at what you do. You just need to be good enough to solve your clients' problems. Learn how to reframe expertise, overcome self-doubt, and start building your freelance business with confidence. 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

When subcontracting becomes your main income source, it's easy to lose your business identity in someone else's brand—almost like you're getting swallowed up. In this solo episode, Preston tackles a question from Garrett, a 30-year-old nonprofit consultant who's concerned about being overshadowed by the seasoned consultant he subcontracts for. Should he merge his business, continue the partnership, or strike out on his own? Preston shares practical strategies for testing your market, setting boundaries, and transitioning from subcontractor to independent consultant without burning valuable bridges. 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

Every freelancer faces this dilemma: A dream client wants to hire you for a project that's bigger than anything you've tackled solo. Do you hire help first and risk the overhead, or do you say yes and scramble to build a team afterward? Preston and Austin dive deep into this classic chicken-and-egg problem, offering a surprising third option that could save your reputation and your sanity. They break down exactly how to de-risk those make-or-break moments when you're ready to level up from solo freelancer to agency owner. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever wondered if your location outside the US is holding you back from landing American clients? In this episode, Preston and Austin tackle a question from Dieter in Europe who's hesitant about offering his services to the US market. You'll discover how to flip perceived geographical disadvantages into powerful positioning strengths, why cultural differences might matter less than you think, and the surprising ways that being "foreign" can actually make you more attractive to American clients. If you've ever doubted whether distance or cultural barriers are limiting your freelance potential, this episode will shift your entire perspective. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Ready to hire your first virtual assistant but not sure where to start? Elena's question hits on something every growing freelancer faces: you have a million different tasks that need doing, but how do you find the right person to handle them all? In this episode, Preston teams up with Austin Church (founder of Freelance Cake Community) to break down the hiring process from character evaluation to smart delegation strategies. Austin shares real insights from his 4+ year relationship with his VA, including why he prioritizes character over skills and his brilliant low-stakes/high-frequency framework for deciding what to delegate first. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → ⁠https://www.freelancecake.com/community⁠ Get Austin's Book, Free Money → ⁠https://austin-l-church.kit.com/cf0feb3e27⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices