Freelance to Founder

Natalie Chen is standing at a pivotal moment in her entrepreneurial journey, wrestling with a challenge many freelancers face: breaking free from being seen as just "the talent" and establishing herself as a true agency owner. Preston Lee and Jason Fishman dive deep into the strategic art of repositioning your business, revealing how to transform client perceptions from viewing you as a solo contractor to seeing you as a comprehensive, high-value agency with a talented team behind you.

Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠

Submit your own question -> ⁠⁠⁠⁠https://freelancetofound...

Marcus is stuck at a critical turning point in his freelance paid ads consulting business. Every time he tries to hire, his carefully built margins evaporate. Preston Lee and Jason Fishman dive deep into the strategic approach of scaling your agency, revealing the essential insights for hiring the right talent, structuring your offer, and ensuring each new team member contributes directly to your bottom line.

Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠

Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠

Jason Linkedin -> https://www.linkedin.com/in/jafishman/

Jason's Business ->...

Layla has achieved an incredible milestone, growing her business from a solo venture to a thriving team of 12 in just two years. But as her company expands, she faces a critical challenge: how to update her messaging, website, and social media to reflect her agency's growth while maintaining the personal touch that helped her succeed. Preston and Haley Raymond dive deep into the art of scaling your brand's story, revealing strategies for positioning yourself as an agency while keeping the human connection that makes your business unique.

Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠

Submit...

Andre is stuck at a critical moment in his freelance career—desperate to stand out but unsure how to transform his skills into undeniable expertise. Preston and Haley Raymond crack open the playbook for positioning yourself as the go-to professional in your field, revealing the strategic secrets of content creation, platform selection, and building a reputation that magnetizes clients. From leveraging LinkedIn to understanding the nuanced art of consistent, value-driven communication, this episode is your blueprint for breaking through the professional noise and becoming the expert everyone wants to hire.

Support our show sponsors -> ⁠https://freelancetofounder.com...

Navigating the world of publicity can feel like a mysterious art, but it's actually an accessible strategy for freelancers and agency owners looking to amplify their message without paying out huge advertising bills. In this episode, PR consultant Haley Raymond breaks down the essentials of earned media, revealing how even small businesses can start building credibility and reaching new audiences through strategic publicity.

Support our show sponsors -> https://freelancetofounder.com/sponsors

Submit your own question -> https://freelancetofounder.com/ask

Connect with Haley:

https://HaleyRaymond.com

https://www...

Transitioning from a solo freelancer to a business leader isn't just about hiring employees—it's about fundamentally changing how you approach work, leadership, and success. In this episode, Preston and Vijay dive deep into the critical mindset shifts required to move from being the person who does everything to the leader who enables others to do their best work.

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...

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. V...

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. Vi...

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 ->...

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...

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...

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...

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...

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...

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 mo...

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...

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 Co...

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 choice...

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...

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...

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...

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...

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...

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...

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 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...

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 yo...

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...

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 ques...

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

Su...

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...

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...

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 is...

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 im...

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 a...

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

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 th...

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 le...

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 spon...

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...

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 co...

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

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

...

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.

...

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...

Worried about raising your rates and losing clients? You're not alone. In this episode, Preston and Austin Church tackle one of the most common freelancer fears: how to increase pricing without damaging client relationships.

But here's the twist—your clients might care about way more than just saving money. Austin shares eye-opening insights about client psychology, the hidden costs of replacing good freelancers, and why charging higher prices can actually earn you more respect.

If you're planning to transition from freelancer to agency owner, this conversation will shift how you think about value, pricing strategy, an...

Lana from Homewear Designs has cracked the code on getting home staging clients through real estate agent relationships in New York and the Hamptons. But she wants to grow faster. Should she double down on what's working or branch out into new channels? Preston and Austin dive into strategies for scaling your proven client acquisition methods while exploring smart ways to reach broader audiences through visual content and strategic partnerships.

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/co...

On today’s show, how can you possibly hire other freelancers to help grow your business when it’s hard to know if you can trust them?

After all, if someone you hire misses a deadline, you’re on the hook with your client.

That’s where Tina finds herself on today’s call. 

She’s thinking about hiring and is willing to trust other freelancers' creative processes. 

But what about their ability to deliver on time? Can she overcome that somehow?

On today’s Q&A episode, A former guest on the show, Jim, writes in with an important question:

I know I shouldn’t charge by the hour, but shouldn’t I pay my subcontractors by the hour?

You might be able to guess our answer. Or it might just surprise you. 

Let’s find out on today’s episode of Freelance to Founder. Here we go!

This Q&A episode was originally aired on November 7th, 2023.

...

On today's show, we get called out by our call-in guest, Erik.

Here's the thing:

Clay and I are always talking about finding referral partners—other freelancers or businesses who can send you new clients as a sort of trade.

You'll refer them to clients, and they'll refer you.

It sounds magical.

But Erik's question is this: how do you actually FIND these kinds of partners?

So we get into it on today's episode of Freelance to Founder. Here we go.

This episode was originally ai...

I am joined by special guest co-host Austin Church on today's show.

He is a very talented freelancer and the author of the new book, Free Money.

It's all about growing your revenue as a freelancer, and we talked today about calculating your survival rate. That's the rate you need to stay in business as a freelancer.

What's the minimum amount you need to make to stay in business? So, if you've wondered how to calculate that rate best, stay tuned for today's Q...

On today’s show, ⁠Molly Cox⁠ calls in with questions about the freelance business she started just six months ago. Top of mind for her:

Should she stay a sole–proprietor or form an LLC?

Before the legal terms tempt you to click away, consider this. This single question could save you thousands of dollars a year in taxes. So keep listening.

That’s just part of what we chat about with Molly.

This episode was originally aired on July 20, 2023.

PS: Get featured in an upcoming Q&A! Just...

On today’s Q&A episode, Luqman writes in with a question. 

He’s a brand-new freelancer and wants to know exactly how to build a freelance network and attract more clients. 

We all know your network can lead to massive growth for your business. So Clay and I break down what has worked well for us and what has totally bombed when it comes to networking. 

If you want to build your network fast, you should try FeedCoyote, the all-in-one freelance collaboration network platfor...

On today’s show, how do you escape the trap of one-time projects and convince your clients that they need what you have to offer on a repeat basis?

That’s part of the hurdle Aurelie faces as she aims to grow her 3-year-old freelance business. 

Aurelie has worked with some huge clients like Wendy’s and the United Nations. 

But almost all of her work has been on one-time projects. 

Which naturally has its limitations.

So we walk Aurelie through a...

On today’s show: how many people does it take to call yourself an agency officially?

Is it one, two, or more than that? This question got us thinking about what it means to be an agency.

Plus, we discuss our ideal team size and answer the question: How many are too many for your team?

It’s all on this episode of Freelance to Founder. Here we go.

This Q&A episode was originally aired on March 5, 2024.

Duration: 00:18:24

On today’s show: do you ever feel trapped by the decisions you make in your business?

Our guest Morgan loves to write. But, early on, she took on quite a few social media clients.

Then, those clients referred more clients. And suddenly, most of her client work is focused on social media marketing — not writing.

So what do you do when your former choices have boxed you into a future you don’t necessarily want?

It’s all on today’s episode of...

On today’s Q&A episode, let’s talk about money. Exactly how much should you save before you can start your agency?

We do our best to answer this question, and it got us wondering: What in the world are we spending all of our money on these days in our own businesses?

So, as a bonus, we break down our finances a bit more to round out the episode. 

It all starts right now on this episode of Freelance to Founder. Here we go...

On today’s show: have you ever wondered when is the right time to start calling yourself an agency?

It can be a bit awkward early on. So Clay and I coach our call-in guest Austin through the right timing. Austin has many other questions as he grows his 6-month-old business. Thanks for joining us.

This episode was originally aired on July 13, 2023.

PS: Get featured in an upcoming Q&A! Just visit ⁠http://freelancetofounder.com/ask⁠ and submit a question. 

Suppo...

In today's Q&A episode, Travis writes about a problem: a few years ago, he moved from Australia to the U.S. to grow his video business.

While things went well at first, work has really slowed down, and he's wondering if there's something about the U.S. market he's completely missing. 

Clay and I have never lived "down under," but we have a few things to consider for anyone looking to break into the US market.

It's all on this episode of Freelance t...

On today’s show, your messaging matters.

And when it comes to getting new clients, it probably matters more than anything else.

So then, why do so many of us miss the mark when explaining our business to potential clients?

It’s something we tackle on today’s episode with call-in guest Tianna. It’s happening right here on Freelance to Founder. Here we go.

This episode was originally aired on November 16, 2023.

PS: Get featured in an upcoming...

On today’s show, we’ve got the longest Q&A episode we’ve ever published—coming in at a whopping 50 minutes plus.

Why so long? Well, I asked Clay a question that really got him riled up. 

It has to do with his experience using the software GoHighLevel—which has exploded in popularity lately.

But Clay’s experience was anything but ideal. You’ll see what I mean in this episode of Freelance to Founder. Here we go.

This episode was originally aired...

On today’s show: are you a bit of a control freak?

To be honest, most freelancers and entrepreneurs we meet are.

But if you never hand off smaller tasks, you never free yourself up to be a founder in your own business.

We talk about that today with our call-in guest, Silvia. 

It’s all happening today on freelance to founder. Here we go.

This episode was originally aired on May 5, 2022.

<...

On today’s show: if you work with a sub-contractor, something we highly recommend—how much extra should you charge your client? And do they have to sign two different contracts?

That’s what Kiki asks us in this Q&A episode of Freelance to Founder. Here we go…

This episode was originally aired on June 21, 2022.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-length coaching calls: ⁠http://freelancetofou...

On today’s show, can you grow without embracing hustle culture? 

That’s just part of what we talk about with return guest: ⁠Travis Boyco⁠.

A few months ago, Travis was trying to decide if he could actually quit his job and take his business full-time.

Now, he’s back, freelancing full-time and hitting us with some of his biggest learnings from going full-time, plus questions he’s run into since.

It’s a fun episode today, and it’s all here on Freelance to F...

In today's Q&A, Rachel Stoneking, from our free ⁠Facebook Mastermind Group⁠ asked how she could get the passion for her business back. She shares her personal feelings of anxiety and disappointment after losing clients with COVID-19 and getting burned out with everything around it. "How do you overcome these negative feelings and connect back with the passion for your business?"

We'll learn a lot from this difficult BUT important question.

This episode was originally aired on June 21, 2022.

To submit your question, visit ⁠FreelanceToFounder.com/AS...

On today’s show, which comes first: hiring to free up time to land big clients or landing big clients to pay for hiring. 

It’s a chicken and egg situation that our guest Zach has been stuck on.

We do our best to answer that question, plus a few others he has, including how to combine two completely different offerings into one killer monthly recurring offer.

It’s all in this episode of ‘Freelance to Founder’—here we go.

(This episo...

On today’s show, where do you start when it comes to making a marketing plan for your business?

That’s what Thomassina asks us and—since Clay and I both have extensive marketing backgrounds—we end up having a lot to say about it.

If you’re not sure where to start when it comes to marketing, then this episode is for you.

This is Freelance to Founder. Here we go!

This episode was originally aired on January 23, 2024.

...

On today’s show, we talk with ⁠Mannat⁠, a student calling from India, with questions about her freelance business.

Mannat is a typographer—she works with lettering and fonts.

But every time Mannat posts her work on social media, she gets packaging design clients and others who don’t match her target audience.

This leaves Mannat asking, “what exactly should I be posting on social media to attract my ideal client?"

We walk her through a few key ⁠social media strategi...

On today’s show: can you become a millionaire as a freelancer?

Podcast listener Suman wrote in with that simple yet not-so-simple question, and we do our best to reveal whether or not you can get rich working as a freelancer.

It’s all in this episode of Freelance to Founder. Here we go!

This Q&A episode was originally aired on September 26, 2023.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Duration: 00:17:55

Have you ever thought: “if I can just get the attention of more people, I could close more clients and grow my business”

That’s where we find today’s guest, Jay. He’s a web developer and SEO expert in Kentucky, USA. And Jay’s only been freelancing for a few months. He’s off to a great start having already closed a half-dozen monthly recurring clients.

Jay’s biggest question is how to get more volume. Or more awareness. So, of course, as marketing geeks Clay and I jump in with s...

On today’s Q&A episode, if you give your client full ownership of your creative work, how much should that cost, and how exactly do you even do that?

That’s the question Nicole hits us with, and it opens up another discussion on who should own your work in the first place.

It’s all in this episode of Freelance to Founder. Here we go.

This Q&A episode was originally aired on December 26, 2023.

To submit your questi...

On today’s show: do you keep hearing how important networking is, but you really just don’t enjoy it?

In this episode, we chat with Morgan, a freelancer from Chicago. Morgan can see the potential in networking with local clients, but can’t quite figure out how to enjoy it.

So, Clay and I start brainstorming a few fun and exciting ways she can leverage her unique talents to ⁠network with local business owners⁠ and potential clients.

Stick around for this fun brainstorming session st...

Today’s question comes from our ⁠free Mastermind group⁠ on Facebook.

Darielle asks: "What's the BEST Software for getting paid faster?"

Getting paid for your work FAST is key, but how do you make it happen?

You'll get the answer here!

This Q&A episode was originally aired on August 8th, 2023.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-length coaching calls: ⁠http://freelancetofounder.com⁠

Support our Sponsors

Our gene...

On today’s show, have you ever thought: if I could just find the right person to hire, I could scale up my business.

That’s how ⁠Virginia⁠ from Argentina feels about her unique content marketing company.

The challenge? Virginia’s company develops content around witchcraft and spiritualism—so she needs teammates who speak fluent English, write well, and understand her unique niche.

It’s a tall order, but Clay and I offered solid advice for ⁠hiring the best freelancers⁠. 

This episode was originally aire...

On today’s Q&A episode, what are the best tools to use as your freelance business grows?

That’s what Cesar asks us because his business is outgrowing tools like Google Drive. 

So, Clay and I launch into our best advice on what makes a good business tool and what makes your business worse… 

It’s all in this episode of Freelance to Founder. Let’s go!

This episode was initially aired on September 12, 2023.

To submit...

Sharing an episode of the Superhero Leadership podcast, hosted by Marvel's former CEO and legendary turnaround expert, Peter Cuneo. Each week, Peter is joined by top performers from business, media, and beyond, leaders who have mastered the art of impact, resilience, and vision. Together, they explore Peter’s 32 leadership essentials, revealing what it really takes to rise, inspire, and lead with purpose. In this episode, Jon Harris, CEO of AthLife, explores how leaders create lasting impact by empowering others, fostering empathy, and embracing lifelong learning. From his journey as DePaul basketball captain to building programs that support athlete development of...

Is freelancing as a family a good idea? Can it actually work?

That’s part of what we get into with our call-in guest, Dave.

Dave is the father of 3 talented young developers. Together, they’ve started an agency.

Well… sort of.

As we talked with Dave, we uncovered this: family dynamics are not the same as business dynamics. And sometimes, managing both can present a real challenge. 

If you’ve ever wondered whether or not to go into business with fami...

On today’s Q&A episode, if a client is willing to pay by the hour or by the project, which one should you choose?

That’s part of Pennygoo’s question, and our answer might surprise you… Here we go!

This episode was originally aired on September 5, 2023.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-length coaching calls: ⁠http://freelancetofounder.com⁠

Support ou...

On today’s show: Can you ever step away from your business? Or are you doomed as an entrepreneur to never enjoy a vacation or time off ever again?

That’s just part of what we talk about with our guest Jim, who’s calling back for a second time on today’s episode.

Jim has quit his job and taken his business full-time. But now he wonders: how do I take the next step so I can work more ON my business than IN my business.

If you’re wondering...

In this Q&A episode, Oliver asks us what it takes to create a portfolio that actually brings in new long-term clients. And since Clay and I are real marketing geeks, we have quite a few ideas for turning your sleepy portfolio into a client-converting machine. It’s all in today’s show, and it starts right now.

This episode was originally aired on August 29, 2023.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-len...

On today’s show: Do you ever feel like you’re just way too busy to actually spend time growing your business?

If so, you’re not alone. We chatted with Will Gibbons, who works with cool clients like Peloton, 3M, and Vizio. 

But Will’s got a problem. A great problem. He’s got too much work. Which means he’s busy.

And he’s worried he doesn’t have time to grow.

Clay and I help him punch through those barriers in this...

Today’s question comes from our ⁠free Mastermind group⁠ on Facebook.

Anna Keith asks: "I’m getting ready to do my taxes and am considering trying software rather than hiring a CPA.

What insights or pros/cons about using software vs. hiring a professional do you have?"

This episode was originally aired on May 3, 2022.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-length coaching calls: ⁠http://freelancetofou...

On today’s show: is it even worth trying to grow your freelance business?

That’s where Rakesh finds himself. He gets most of his clients from freelancing platforms like Upwork. 

And the market for web designers and developers is just so saturated, he doesn’t even know if he should continue with his business. 

If you’ve ever felt this way, today’s show is for you. It all starts right now on this episode of Freelance to Founder.

Oh, and really quick...

This episode's question came in via email.

Nico works as a designer for a company right now, and he wants to start freelancing on the side and build a business.

He said, “I was thinking of creating a portfolio, including the projects I've completed in my current company, but in a fictitious way (use different names, organizations, etc.) Also, state that this is a fictional project but that the process and outputs are the same. Do you think this will work to close deals?

If...

On today’s show: Is a VA a good first hire in your company?

We’re joined by call-in guest Nils, who wants to know when and how to hire a VA—a virtual assistant.

But Clay and I slam on the brakes and force Nils to answer the question: Is a VA even the best first hire to make?

The answer might surprise you. It’s all on today’s episode of Freelance to Founder. Let’s go!

This episode...

Today’s question comes from our ⁠free Mastermind group⁠ on Facebook.

Darielle asks: "What's the BEST Software for getting paid faster?"

Getting paid for your work FAST is key, but how do you make it happen?

You'll get the answer here!

This Q&A episode was originally aired on August 8th, 2023.

To submit your question, visit ⁠FreelanceToFounder.com/ASK⁠, and we'll feature you on an upcoming episode.

Listen to our full-l...

On today’s show: What should you do when you’re not getting the kind of respect you deserve from your clients?

That’s just one of many questions we got today from our guest, Cathal, calling in from Germany.

A few times now, Cathal has been hired by a manager only to later have that manager’s team give him pushback once he gets to work.

So, we work with him on a few ideas on how to get everyone on board with the outs...

On today’s Q&A episode, what are the best tools to use as your freelance business grows?

That’s what Cesar asks us because his business is outgrowing tools like Google Drive. 

So, Clay and I launch into our best advice on what makes a good business tool and what makes your business worse… 

It’s all in this episode of Freelance to Founder. Let’s go!

This episode was initially aired on September 12, 2023.

T...