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PODCAST

Freelance to Founder

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

business entrepreneurship

All Episodes

19:17

What To Systemize First?

Freelance to Founder ·

2026/02/26

Dave's agency is humming along, but everything — how he prices, how he delivers, how he handles problems — lives entirely in his head. It's worked so far, but he can feel it starting to strain. So he's asking the question every growing agency owner eventually faces: if I had to pick just one or two things to systemize first, what would they be? Preston, Sabrina, and Jesse P. Gilmore from Niche in Control dig into exactly that — walking through a practical, priority-ordered approach to getting out of

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23:32

Real Freedom vs. Another "Job"

Freelance to Founder ·

2026/02/25

Priya left her full-time job to build an agency on her own terms — and now finds herself buried under client obligations she can't seem to escape. Every new project feels like a trap, and turning down work feels like a risk she can't afford. Preston and Sabrina sit down with Jesse P. Gilmore of Niche in Control to map out exactly how agency owners can build for freedom instead of accidentally building another job — covering time systems, ideal client selection, offer design, and the mindset work

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26:58

Stop Doing Everything Yourself...Here's Why

Freelance to Founder ·

2026/02/24

Marcus built his agency the hard way—doing everything himself until the clients came, the revenue got steady, and the team grew. But now, with real momentum on his side, he's still the one making every call, reviewing every deliverable, and firefighting every problem. He suspects this habit that once made him successful might now be the very thing capping his growth. Preston and Sabrina sit down with Jesse P. Gilmore from Niche in Control to help Marcus understand the difference between scrappy

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18:49

This Mistake Cost Me $30,000

Freelance to Founder ·

2026/02/23

Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try to handle it herself. Preston and Austin Church—both of whom learned the hard way—share what they wish someone had told them earlier, including the costly mistake that set Preston back $20,000 to $30,000, and the simple mindset shift that makes all the difference.Support our show

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19:11

This Matters Less Than You Think

Freelance to Founder ·

2026/02/20

Rashid wants to land clients outside his home country, but the unknowns are holding him back — different governments, tricky payment terms, and contracts that feel impossible to enforce across borders. Preston and Austin Church dig into exactly how to protect yourself when working with international clients, and their answer might surprise you: where a client lives matters far less than most freelancers think. The real work is learning to read the room early, set airtight expectations before a

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22:53

Are You Missing Out on Money?

Freelance to Founder ·

2026/02/19

Aisha is just starting out as a freelancer and wrestling with the question that trips up almost everyone in the early days: what should I actually charge? She knows she doesn't want to undersell herself, but she also has no idea where to set her rates. Preston and Austin Church—veteran freelancer and author of Free Money—unpack three different pricing approaches, make the case for building your rate around what your life actually costs, and explain why anchoring high (and negotiating scope, not

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19:09

Do I Have to Sacrifice Family for Growth?

Freelance to Founder ·

2026/02/18

Jenna finds herself wanting to build a successful business without sacrificing her values or family time. Preston Lee and Dawn Andrews share what it takes to design a leadership role that truly fits your life, offering compassionate insights for ambitious professionals navigating the complex terrain of work-life integration.Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Dawn on Linkedin ->

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20:35

The Real Power of SOPs

Freelance to Founder ·

2026/02/17

For Nicole, what started as a quest for freedom through freelancing has morphed into a complex leadership challenge—managing a team that seems to consume more time than the work itself. Preston Lee and Dawn Andrews explore the art of creating standard operating procedures (SOPs) that transform team management from a headache into a strategic advantage. They reveal the secrets to empowering your team, reducing management overhead, and reclaiming the entrepreneurial freedom you originally

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17:26

Fighting Imposter Syndrome

Freelance to Founder ·

2026/02/16

Amanda is standing at a pivotal moment in her leadership journey—wrestling with the internal doubts that plague many first-time team leaders. As she steps into her new role, the weight of proving herself feels overwhelming. Preston and Dawn Andrews dive deep into the psychology of leadership, revealing how vulnerability, communication, and embracing risk can transform imposter syndrome from a paralyzing force into a catalyst for growth and confidence.Support our show sponsors ->

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23:41

When Paperwork = Death

Freelance to Founder ·

2026/02/13

Jason from our listener community is stuck in a common entrepreneurial trap—feeling overwhelmed by the administrative demands of maintaining his LLC. Preston Lee and Bobby Casey dive deep into why business structure matters, how to manage compliance without losing your mind, and the critical steps every business owner needs to know about protecting their assets.Bobby Casey, founder of Business Anywhere and an international tax lawyer, breaks down the essential reasons why entrepreneurs should

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15:45

With Money, 'Just Surviving" Isn't Enough

Freelance to Founder ·

2026/02/12

Parker is stuck navigating the murky waters of freelance finance, desperate to transform his business from a mere survival mode into a strategic growth machine. Preston and George Thomas dive deep into the critical financial strategies that separate struggling freelancers from successful business owners. From understanding revenue forecasting to building a financial support team, this episode cracks open the playbook for freelancers ready to take control of their financial future and scale their

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19:42

Will You Actually Have Retirement Money?

Freelance to Founder ·

2026/02/11

Lana has built a successful freelance career but finds herself paralyzed by the complexities of retirement planning. Preston Lee and financial expert George Thomas unpack the essential strategies for independent professionals to build sustainable wealth. Diving deep into retirement accounts, investment opportunities, and wealth-building tactics, this episode provides a comprehensive roadmap for freelancers looking to secure their financial future without the safety net of traditional

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17:33

Family vs. Business

Freelance to Founder ·

2026/02/10

Lauren is navigating a pivotal moment in her entrepreneurial journey—her business has taken off since becoming a parent, but she's struggling to find harmony between her family's needs and her business ambitions. Preston and Lindsay dive deep into the messy, beautiful reality of being a parent-entrepreneur, sharing hard-earned wisdom about energy management, setting boundaries, and creating a life where both your family and your business can thrive. This episode is a raw, honest look at how to grow

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20:08

Should I Give Up and Go Back to Corporate?

Freelance to Founder ·

2026/02/09

Nicole is standing at a critical crossroads in her entrepreneurial journey. After leaving corporate America to start her own business, she's wrestling with doubts and financial uncertainty. Preston and Lindsay dive deep into the crucial strategies for new entrepreneurs facing this make-or-break moment: understanding that business success is a marathon, not a sprint, and learning how to navigate the challenging early stages of building your own venture.Support our show sponsors ->

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18:44

Where Should You Spend Your Money?

Freelance to Founder ·

2026/02/06

Amanda is standing at a critical crossroads in her entrepreneurial journey, wrestling with one of the most challenging questions every bootstrapper faces: How do I strategically spend my limited funds without taking on investors? In this powerful episode, seven-figure entrepreneur Lindsay Pinchuk breaks down the exact playbook for making smart financial decisions that can transform a bootstrapped business from surviving to thriving. With candid insights from her own entrepreneurial path—building a

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18:10

From Manager to Solopreneur

Freelance to Founder ·

2026/02/05

Kevin is standing at a pivotal crossroads in his professional journey—transitioning from managing teams to becoming a solopreneur. Preston Lee and Moe Choice dive deep into the mental and strategic shifts required when moving from leading groups to leading yourself. With insights from Moe's extensive background as a six-time co-founder and leadership coach, this episode unpacks the emotional landscape of going solo, building support networks, finding the right mentors, and discovering the unique

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25:09

Why You Still Don't Feel "Free"

Freelance to Founder ·

2026/02/04

Daniel is trapped in a calendar packed with work, questioning the true meaning of a "freedom-based business." Preston and Moe dive deep into the nuanced world of solopreneurship, unpacking what freedom really means—and it's not just about having an empty calendar. From passionate contribution to strategic positioning, this episode reveals how to create a business that doesn't just provide income, but fuels your daily excitement and purpose.Support our show sponsors ->

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21:12

The 'Freelancer Trap'

Freelance to Founder ·

2026/02/03

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 freelancers break free from the "bricklayer" mentality and become true business owners who sell

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18:04

Burned in the Past & Scared to Hire

Freelance to Founder ·

2026/02/02

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 value to your business. From communication techniques to creating robust systems, they reveal how to

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19:15

You've Got to Stop Doing Everything

Freelance to Founder ·

2026/01/30

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 episode reveals the strategic secrets of knowing when and how to start delegating, hiring, and working on

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545 results

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