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 28, 2025 • 20min
Why We Struggle to Delegate
Vijay Rajendran, a founder coach and author of The Funding Framework, dives into the crucial art of delegation. He explains how effective delegation distinguishes successful founders from struggling freelancers. Topics include the delegation spectrum, the importance of feedback loops, and managing perfectionism. Vijay offers practical strategies like setting clear outcomes and embracing servant leadership to empower teams. With insights on reducing mistakes and fostering autonomy, he provides a roadmap for entrepreneurs to scale their businesses efficiently.
Nov 27, 2025 • 18min
How to Navigate Your First Big Project
In this conversation, Vijay Rajendran, a founder and startup coach with expertise in AI ventures, shares crucial insights on leading your first big project as a freelancer. He discusses identifying your unique strengths and assembling a complementary team, avoiding the trap of hiring duplicates of yourself. Vijay emphasizes the importance of hiring for diverse roles and leveraging tools like the Working Genius assessment to align team members' work styles. He also warns against the pitfalls of poor communication and suggests testing a short-term team before committing.
Nov 26, 2025 • 16min
Why You're Still Afraid to "Sell" Yourself
George Azar, CPA and founder of Bright Budget, shares his expertise in helping freelancers navigate finances. He discusses the common struggle with self-promotion, highlighting strategies for authentic marketing without feeling pushy. Azar emphasizes the importance of aligning with clients' values and targeting the right audience, positioning genuine relationships as crucial for organic referrals. He also recommends networking locally and being patient, as cultivating connections can lead to future opportunities.
Nov 25, 2025 • 29min
The Real Truth About S-Corps (Don't Get Tricked)
In this insightful discussion, George Azar, a CPA with nearly a decade of experience, shares expert insights on the complexities of S-Corporations. He debunks common myths about big tax savings from S-Corp elections, emphasizing the importance of understanding marginal versus effective tax rates. George outlines the self-employment tax burden for freelancers and explains the significance of reasonable salary requirements. He stresses the need for a careful cost-benefit analysis before choosing the S-Corp path, warning against biased advice from some advisors.
Nov 24, 2025 • 18min
Should You Hire a Bookkeeper? (This Might Surprise You)
Join George Azar, CPA and founder of Bright Budget, as he shares vital insights on managing finances for freelancers and small business owners. He explains the differences between personal and business finances, emphasizing the importance of understanding taxes. George discusses when to transition from basic spreadsheets to professional bookkeeping services, highlighting key signs that indicate you should hire a bookkeeper. Learn how investing in these services can save you time and stress, making your freelancing journey smoother.
Nov 21, 2025 • 21min
How to Budget When Your Income Fluctuates
George Azar, a CPA and founder of Bright Budget, provides insightful strategies for freelancers managing fluctuating incomes. He stresses the importance of setting aside 25-30% for taxes and building an emergency reserve of 3-6 months' expenses. George suggests utilizing high-yield savings accounts to combat inflation. He recommends budgeting by percentages rather than fixed amounts and categorizing expenses into life, living, and savings. Finally, he highlights the benefits of maintaining separate bank accounts to streamline financial management.
Nov 20, 2025 • 14min
Client Asks for Favors—What Should I Do?
Chanda Coston, a Navy veteran and business strategist, shares her insights for freelancers facing the dilemma of client requests for unpaid favors after project completion. She emphasizes the importance of establishing clear boundaries by introducing sign-off steps and timelines. Chanda also advocates for offering maintenance subscriptions to transform casual requests into recurring income, and highlights the benefits of subcontracting to manage workload. With practical tips, she guides listeners on creating structured systems to support clients while protecting their own time.
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.
