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 19, 2025 • 18min
Switch From Hourly to Flat Rate (w/out Losing Money)
Chanda Koston, a Navy veteran and business strategist, shares her expertise on transitioning from hourly to flat-rate pricing, especially for purpose-driven entrepreneurs, particularly women over 40. She emphasizes the importance of researching market rates and realistically estimating project timeframes to avoid underpricing. Chanda suggests piloting flat fees and considering hybrid pricing models. The duo discusses how flat rates reward efficiency and the significance of effective messaging to enhance perceived value. They also tackle strategies for transitioning existing clients smoothly.
Nov 18, 2025 • 14min
Is It Best to Drop Late-Paying Clients?
Chanda Koston, a Navy veteran and business strategist, joins the discussion to navigate the tricky waters of managing late-paying clients. She emphasizes the importance of setting clear payment terms, including requiring upfront deposits for new clients. The duo also explores how building recurring revenue can stabilize cash flow and reduce stress. They provide practical tips, like securely storing payment details to ensure timely payments, and advise freelancers on whether to keep or let go of challenging clients.
Nov 17, 2025 • 20min
Should You Fill Income Gaps w/ Low-Paying Clients?
Chanda Coston, a Navy veteran and business strategist, offers invaluable insights for freelancers facing financial uncertainty. She discusses the risks of taking low-paying clients, urging clarity around ideal clients and pricing. While exceptions exist, she emphasizes temporary acceptance of lower pay only when absolutely necessary. Chanda also shares strategies for testing pricing and leveraging feedback to refine business models. Her approach balances short-term income needs with long-term sustainability, ensuring growth without compromising value.
Nov 14, 2025 • 20min
5 Places to Get More Leads and Attention
Dr. Noah St. John, known as the Zero Friction Doctor and creator of Afformations, shares his MAPSSS method for lead generation. He discusses the five key stages to scale a business, including crafting irresistible offers and utilizing effective funnels. Noah emphasizes leveraging other people's audiences through podcasts and media, building referral partnerships, and the smart use of pay-per-click ads. He also highlights the importance of positioning yourself as an authority through speaking engagements and adapting SEO strategies for AI-driven search.
Nov 13, 2025 • 24min
These Habits May Be Holding You Back
Dr. Noah St. John, known as the Zero Friction Doctor and the father of affirmations, shares insights on overcoming self-imposed barriers to success. He delves into how clarifying goals is essential before changing habits and discusses the concept of 'head trash' that hinders growth. Noah reveals why willpower isn't enough, introducing a five-element model of habits. He offers practical strategies to conquer procrastination and suggests morning routines to replace negative habits, emphasizing that strong desire must outweigh fear to drive meaningful action.
Nov 12, 2025 • 20min
How Long Does It Take to Succeed?
Meredith Rice Cooley, founder of Page and Purpose and a mentor to aspiring freelance copywriters, shares her journey from teaching to building a stable freelance business. She discusses the importance of testimonials and the value of raising prices for perceived income. Meredith emphasizes dedicating time to consistent marketing to prevent revenue gaps and suggests offering retainer services for predictable income. She also reassures listeners that with dedication, it's possible to leave a full-time job within a year after gaining clients.
Nov 11, 2025 • 18min
What We Wish We Knew Before Jumping In
Meredith Rice Cooley, founder of Page and Purpose, shares her insights on launching a freelance career, especially for teachers transitioning to copywriting. She advises against waiting for the perfect branding, emphasizing the importance of getting clients first. Meredith highlights the value of showcasing polished spec work and building a professional network early on. She also discusses accepting slow progress and celebrating small wins to keep the momentum going, insisting that consistency leads to eventual success in freelancing.
Nov 10, 2025 • 18min
Our Biggest Lessons Learned as Freelancers
In this engaging conversation, Meredith Cooley, founder of Page and Purpose and mentor for teacher-copywriters, joins Preston Lee to share valuable freelancing insights. They dive into setting boundaries with clients and the importance of effective communication. Meredith emphasizes the need to embrace change in entrepreneurship and discusses balancing flexibility with focus. Tips on time management, including the Pomodoro technique, and strategies for minimizing distractions are highlighted, making this a must-listen for aspiring freelancers.
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.
