Freelance to Founder
Millo
Freelance to Founder is a call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle.
The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own.
Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level.
You can submit your questions at FreelanceToFounder.com/ask
If you enjoy content from shows like The Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder.
Join us every weekday to take the next step on your journey from ... freelance to founder.
The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own.
Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level.
You can submit your questions at FreelanceToFounder.com/ask
If you enjoy content from shows like The Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder.
Join us every weekday to take the next step on your journey from ... freelance to founder.
Episodes
Mentioned books
Nov 7, 2025 • 21min
Balancing Self-Employment Dream with Full-Time Job
Join Meredith Cooley, a former educator turned savvy copywriter, as she shares her journey and insights on balancing a full-time job with the dream of freelancing. She emphasizes the importance of mindset during transitions and offers creative strategies for maximizing small time blocks, like using morning hours and commute times for prospecting. Meredith also reveals how a time audit can uncover hidden hours and discusses setting boundaries with clients. Her teaching experience adds an edge of credibility, making her advice a goldmine for aspiring freelancers.
Nov 5, 2025 • 12min
How We Got Our Very First Clients
In this discussion, AJ Cassata, the founder of Revenue Boost, shares his journey in helping B2B businesses with cold outreach. He recounts how he landed his first client by engaging directly with a bagel shop owner. AJ emphasizes leveraging your existing network for quick connections and suggests offering low-cost or free services to build your portfolio. With practical advice on outreach strategies, he reminds listeners that successful freelancing is often a numbers game, where the first client leads to more opportunities.
Nov 4, 2025 • 17min
Buying Back Your Time as a Freelancer
In this engaging discussion, AJ Casada, founder of Revenue Boost and a former freelancer, shares invaluable insights on reclaiming time as a freelancer. He emphasizes the importance of conducting a two-week time audit to identify where time is lost and recommends delegating low-value tasks. AJ highlights the dangers of low pricing and stress from client demands, suggesting strategies like setting boundaries and utilizing AI for efficiency. Listeners will learn how to balance workload, streamline processes, and ultimately buy back their time to focus on revenue-generating activities.
Nov 3, 2025 • 19min
Why You're (Still) in the Feast-Famine Stage
In this engaging discussion, AJ Casada, founder of Revenue Boost, shares his journey from freelancer to agency owner, focusing on how to escape the feast-famine cycle. He emphasizes the importance of creating recurring revenue to stabilize income. AJ advocates for automated lead-generation systems, highlighting low-volume ads and email lists. Consistent marketing is key to avoiding income dips, and he recommends practical tools for automation. Lastly, AJ offers insights on hiring strategically to support growth while keeping lead generation a priority.
Nov 1, 2025 • 22min
Stuck with Low-Paying Clients? Here's the Fix...
In this engaging discussion, AJ Casada, Founder of Revenue Boost, shares his expert strategies for freelancers trapped with low-paying clients. He highlights how referrals can limit income and recommends proactive outreach methods to attract premium international clients. AJ discusses effective lead generation techniques, like offering free audits, and emphasizes the importance of personalized communication. He also explains the nuances of performance guarantees and how to craft a compelling pitch for higher-value companies.
Oct 31, 2025 • 20min
Can You Raise Rates w/out 'Scaring' Away Clients?
In this insightful discussion, AJ Cassata, Founder of Revenue Boost, shares his expertise on pricing strategies for freelancers and agencies. He emphasizes the importance of gradually raising rates and testing market tolerance to find the sweet spot without alienating clients. AJ explains how higher prices can attract better clients and reduce workload, and stresses that pricing should reflect the value delivered rather than costs. The conversation also highlights the need for confidence and clarity in communicating value to justify rate increases.
Oct 30, 2025 • 16min
Is "Find a Niche" Outdated Advice?
Join Christine Olivas, Founder and CEO of No Single Individual, as she shares her expertise on niching in the creative industry. Christine breaks down the myth that specialization is always essential. Instead, she advocates for a thoughtful approach, encouraging freelancers to experiment before committing to a niche. Discover how to validate market demand through client conversations and the benefits of building a small team to balance various services. Ultimately, it’s about pursuing what you love while ensuring it aligns with market needs.
Oct 28, 2025 • 15min
Charge More (Yes, Really)
Christine Olivas, Founder and CEO of No Single Individual, shares her expertise on pricing strategies for freelancers. She explores the psychological hurdles like imposter syndrome that hold many back from raising their rates. With insights on the impact of inflation, Christine emphasizes the importance of confidence in value assessment. They discuss effective tactics for communicating increases to clients, advocating for tiered pricing to alleviate price sensitivity. Throughout, the focus remains on nurturing client relationships, which can soften the blow of rate hikes.
Oct 27, 2025 • 16min
Is Your Portfolio Broken?
In this engaging discussion, Christine Olivas, Founder and CEO of No Single Individual, shares invaluable insights on crafting an effective portfolio that converts clients. She reveals creative strategies for showcasing limited work, such as using employer logos for credibility and anonymized case studies to illustrate your process. Christine emphasizes collecting predictive testimonials and suggests alternative proof like recorded consultations. Tune in for tips that make building your portfolio both strategic and compelling!
Oct 23, 2025 • 18min
Find Networking Groups That Don't Suck
In this engaging conversation, Clay Mosley, founder of GoLinus.com and agency-builder, offers savvy insights on effective networking. He explains why many local groups can feel spammy and shares tips on vetting them online. Discover the importance of visiting multiple groups to gauge member reliability and the value of personal invitations. Clay emphasizes that higher-cost groups often attract more serious members, making them worth considering. Plus, he encourages building trust through one-on-one meetings for better referrals. Networking doesn’t have to be painful!
