Freelance to Founder

Alex has built a solid freelance income but feels trapped in a cycle of trading time for money. Seeking to transform his business from a job-like grind to a strategic growth engine, he asks a critical question: How do you know when it's time to completely redesign your business or just keep working harder on what you've already got going? Preston and Moe dive deep into the strategies that help fre...

When bad contractor experiences leave you gun-shy about hiring, how do you rebuild trust and create a successful team? Emily's struggle with past hiring mishaps is a common challenge for freelancers and agency owners. In this episode, Preston and Kevin Rice dive deep into the art of effective hiring, offering practical strategies for finding, integrating, and supporting contractors that truly add...

Mark is stuck in the freelance grind—working nonstop and wondering how to transform his solo operation into a real company. Preston Lee and Kevin Rice dive deep into the critical moment when freelancers must shift from doing everything themselves to building a sustainable business. Drawing from Kevin's experience scaling a two-person startup to a 200-person agency with a nine-figure exit, this epi...

Kevin Rice knows the delicate dance of entrepreneurship and fatherhood all too well. After scaling his digital agency to a nine-figure exit, he discovered the hard truth that success means nothing if it comes at the cost of your family connections. In this powerful episode, Kevin shares his personal journey of learning to be an intentional parent while building a thriving business, offering a road...

Michael is standing at a critical crossroads in his entrepreneurial journey—desperate to break through the seven-figure barrier but unsure how to transform his current six-figure business into something truly scalable. In this episode, Charles Gaudet, CEO of Predictable Profits and renowned business coach, cracks open the playbook for moving beyond referrals and hard work into a strategic, demand-...

Jordan is struggling with the modern remote work challenge—feeling like his brain never fully switches off. Preston and Steven dive deep into practical strategies for creating mental boundaries, exploring how freelancers and remote workers can design intentional work rituals that help them transition in and out of professional headspace. From creating dedicated workspaces to developing personal 'c...

Anthony is standing at a critical crossroads in his entrepreneurial journey—he's just hired his first two teammates and is wrestling with the most fundamental leadership challenge: how to spend his time effectively. Preston and Steven Puri dive deep into the art of leadership, unpacking the delicate balance between empowerment and oversight, and revealing the transformative power of deep work in a...

Ethan has been hustling for three years, but feels stuck in a business that's just "meh". Preston Lee and Steven Puri dive deep into the critical strategies for transforming a stagnant freelance business into a thriving agency. From identifying true market pain points to finding authentic mentors who have actually achieved what you're aiming to do, this episode provides a raw, no-nonsense roadmap...

Omar is standing at a critical crossroads in his business, wrestling with a fundamental hiring decision that could shape his team's future. Should he bring on a jack-of-all-trades virtual assistant who can handle multiple tasks, or invest in a specialized VA with laser-focused expertise? Preston Lee and Joey Vitale dive deep into the strategic nuances of VA hiring, revealing a framework that helps...

Melissa is standing at a critical crossroads in her freelance business—overwhelmed by workload but paralyzed by the fear of delegation. Preston and Joey Vitale dive deep into the art of hiring your first virtual assistant (VA) without risking your business's reputation or quality of work. From accountability strategies to building emotional safety for new team members, this episode provides a road...

Keisha's agency is at a critical turning point. As her business grows, she's wrestling with the ultimate entrepreneurial challenge: how to build a team without losing control or compromising quality. Preston Lee and Joey Vitale dive deep into the strategic art of hiring, revealing a nuanced approach to scaling your business from a one-person show to a thriving agency. From the risks of top-down hi...

Hannah is wrestling with a critical question every growing freelancer faces—when and how to implement professional contracts that protect both parties and set the stage for successful client relationships. Preston Lee and business lawyer Joey Vitale crack open the playbook for creating contracts that do more than just protect your business—they build trust, clarify expectations, and serve as a pow...

Luis is standing at a critical crossroads in his agency's journey. Clients keep requesting additional marketing channels—email, influencers, partnerships—but he's worried about becoming a "do everything" agency that loses its core focus. Preston and Jason Fishman dive deep into the strategic art of service expansion, revealing how to grow your offerings without sacrificing quality or diluting your...

Samantha is wrestling with one of the most critical challenges for new freelancers: how do you actually price your services based on value? Preston Lee and Amy Suto dive deep into the nuanced art of pricing your freelance work, breaking down the myths of the starving artist and revealing strategic approaches to valuing your unique expertise. From understanding the emotional weight of your delivera...

Beatriz has been a graphic designer for six years, working for others, but now stands at a critical crossroads. She wants to start freelancing as a digital artist but finds herself wrestling with an internal conflict: how can she confidently charge for her creative work without feeling like she's "selling out"? Preston Lee and Amy Suto dive deep into the psychological hurdles creatives face when t...

David is at a pivotal moment in his writing career, caught between continuing lucrative client work and pursuing his dream of building a personal writing platform. Preston and Amy Sudo dive deep into the strategic approach of simultaneously serving clients while investing in your own intellectual property. From leveraging Substack to creating multiple income streams, this episode reveals the bluep...

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 contr...

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...

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 you...

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 levera...

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...

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 -> http...

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:...

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 Submi...

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://freelancetofounde...