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Freelance to Founder

Freelance to Founder

Red Flags Every Freelancer Should Know Before Signing

Sep 8, 2026 · 22 min · 12 segments

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about…

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about winning in court — it's about setting expectations before the work even begins. They walk through the deposit rules, red flags, and reference checks that keep freelancers from getting burned, whether their next client is down the street or halfway around the world. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about…

Speakers: Preston LeeHostAustin ChurchGuest

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Top entities: Freelancer×2 Home Depot×5 United States×4 Lowe's×5 LinkedIn×2

Show signals: SuitabilitySafeBiasNot politicalAudience≈32k followers

Welcome and episode setup0:09 – 1:07

Preston LeeHost

0:09

Hello and welcome to another episode of Freelance to Founder, where we help you start freelancing, grow your agency, and live the work life you've always wanted.

Preston LeeHost

0:17

You can send in your questions at FreelanceToFounder.com. I'm Preston.

Preston LeeHost

0:23

I started freelancing 15 years ago, which Austin last episode called me a dinosaur poor.

Preston LeeHost

0:28

But from there, I've built, grown, or sold multiple successful businesses.

Preston LeeHost

0:32

Together with my guest co-hosts, I want to help you do the same.

Preston LeeHost

0:34

And speaking of guest co-hosts, Today I am joined again by my friend Austin Church.

Preston LeeHost

0:39

He's been on the show a number of times and was just on last episode.

Preston LeeHost

0:42

We talked all about pricing.

Preston LeeHost

0:43

Go back and listen to that if you enjoyed today's episode.

Preston LeeHost

0:47

But Austin is the founder of the Freelance Cake Community, helping advanced freelancers earn six figures and build profitable, joyful businesses.

Preston LeeHost

0:55

Austin, welcome back today.

Austin ChurchGuest

0:57

Thank you.

Austin ChurchGuest

0:58

I hope to insult you again if given the opportunity.

Preston LeeHost

1:03

I hope so as well.

Preston LeeHost

1:06

Let's dive into today's question.

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FreelancerEntityJob title
97%2 mentions
Home DepotCompanyHome improvement company
91%5 mentions
United StatesCountryCountry in North America
85%4 mentions
Lowe'sCompanyRetail company
79%5 mentions
LinkedInSoftware ApplicationSocial networking service
74%2 mentions
Donald TrumpPerson45th and 47th U.S. President
68%2 mentions
Whirlpool CorporationCompanyHome appliance company
62%2 mentions
Maya AngelouPersonAmerican memoirist and essayist
56%1 mention
PayPalCompanyFinancial technology company
50%4 mentions
TheanineEntity
44%3 mentions
Artificial intelligenceEntityProfessional field
38%2 mentions
MiroSoftware ApplicationSoftware
32%1 mention
Harvard UniversityCollege or UniversityPrivate university in Cambridge, Massachusetts
26%1 mention
GoogleCompanyTechnology corporation
21%1 mention
YelpCompanyCompany
15%1 mention
David SirotaPersonAmerican journalist
9%2 mentions
Upwork Inc.CompanyCompany
3%2 mentions

Society
ContractsBusiness > Freelancing > International Freelancing
Payment IssuesBusiness > Freelancing > International Freelancing > Contracts
Red FlagsBusiness > Client Relations > Trust Building
Best PracticesBusiness > Client Relations > Trust Building > Red Flags
Dispute ResolutionLaw > Contracts > International Law
Contract ClausesLaw > Contracts > International Law > Dispute Resolution
Global WorkforceSociety > Work Culture > Freelancing Trends
Remote WorkSociety > Work Culture > Freelancing Trends > Global Workforce
Freelancing ImpactGovernment > International Relations > Global Economy
Cross-Border WorkGovernment > International Relations > Global Economy > Freelancing Impact
Cultural ConsiderationsGovernment > International Relations > Global Economy > Freelancing Impact > Cross-Border Work
International RelationsGovernment
FreelancingBusiness
Freelancing TrendsSociety > Work Culture
Work CultureSociety
ContractsLaw
Trust BuildingBusiness > Client Relations
International LawLaw > Contracts
Global EconomyGovernment > International Relations
Client RelationsBusiness
International FreelancingBusiness > Freelancing
Law
Government
Business

Welcome and episode setup0:09 – 1:07

Preston LeeHost

0:09

Hello and welcome to another episode of Freelance to Founder, where we help you start freelancing, grow your agency, and live the work life you've always wanted.

Preston LeeHost

0:17

You can send in your questions at FreelanceToFounder.com. I'm Preston.

Preston LeeHost

0:23

I started freelancing 15 years ago, which Austin last episode called me a dinosaur poor.

Preston LeeHost

0:28

But from there, I've built, grown, or sold multiple successful businesses.

Preston LeeHost

0:32

Together with my guest co-hosts, I want to help you do the same.

Preston LeeHost

0:34

And speaking of guest co-hosts, Today I am joined again by my friend Austin Church.

Preston LeeHost

0:39

He's been on the show a number of times and was just on last episode.

Preston LeeHost

0:42

We talked all about pricing.

Preston LeeHost

0:43

Go back and listen to that if you enjoyed today's episode.

Preston LeeHost

0:47

But Austin is the founder of the Freelance Cake Community, helping advanced freelancers earn six figures and build profitable, joyful businesses.

Preston LeeHost

0:55

Austin, welcome back today.

Austin ChurchGuest

0:57

Thank you.

Austin ChurchGuest

0:58

I hope to insult you again if given the opportunity.

Preston LeeHost

1:03

I hope so as well.

Preston LeeHost

1:06

Let's dive into today's question.