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Freelance to Founder

Freelance to Founder

Charging 2X for the Same Job?

Sep 15, 2026 · 24 min · 12 segments

Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they actually need a…

Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they actually need a strategy first. Do you upsell them on the spot and risk scaring them off, or just deliver what they asked for and eat the extra work for free? Preston and Austin break down exactly when to introduce a strategy engagement, how to phrase the offer without sounding like a bait-and-switch, and the four pricing containers — from a quick clarity call to a full strategy sprint — that let you charge for expertise you've been giving away. 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

Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they actually need a…

Speakers: Preston LeeHostAustin ChurchGuest

Spotify Apple Podcasts YouTube Amazon Music Website

Top entities: Creatine×4 ElevenLabs×4 Google×7 Gmail×3 Organization

Show signals: SuitabilitySafeBiasNot politicalAudience≈32k followers

Welcome to Freelance to Founder0:00 – 0:55

Preston LeeHost

0:00

[upbeat music] 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/ask.

Preston LeeHost

0:23

I'm Preston Lee.

Preston LeeHost

0:23

I started freelancing 15 years ago, but from there I've built, grown, or sold a few successful businesses of my own.

Preston LeeHost

0:30

And w- together with my guest co-hosts, I wanna help you do the same.

Preston LeeHost

0:33

Uh, if you are interested in growing your business from being a freelancer to a founder, if you wanna scale beyond yourself, this show is for you.

Preston LeeHost

0:41

We're here answering your questions every single weekday, and today I'm joined again by a friend of the show, Austin Church.

Preston LeeHost

0:48

Austin is the founder of the Freelance Cake community for advanced freelancers.

Preston LeeHost

0:53

We'll talk more about that a little bit later in the show.

Preston LeeHost

0:54

But Austin, Austin, welcome.

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CreatineEntityCompound
97%4 mentions
ElevenLabsCompanySoftware development company
91%4 mentions
GoogleCompanyTechnology corporation
85%7 mentions
GmailWebsiteWeb site
79%3 mentions
OrganizationEntity
74%1 mention
LinkedInSoftware ApplicationSocial networking service
68%2 mentions
Google DocsSoftware ApplicationComputer program
62%4 mentions
search engine optimizationEntity
56%1 mention
Donald TrumpPerson45th and 47th U.S. President
50%2 mentions
Artificial intelligenceEntityProfessional field
44%2 mentions
ClickUpCompanyProject management software company
38%3 mentions
GeminiEntity
32%1 mention
NotionSoftware ApplicationProductivity software
26%1 mention
Asana, Inc.Software ApplicationSoftware
21%1 mention
SeattleCityCity in Washington State
15%1 mention
MiroSoftware ApplicationSoftware
9%1 mention
David SirotaPersonAmerican journalist
3%2 mentions

Time ManagementBusiness > Project Management > Productivity
OrganizationBusiness > Project Management > Freelancing
DeadlinesBusiness > Project Management > Freelancing > Organization
Project BriefsBusiness > Project Management > Documentation
TemplatesBusiness > Project Management > Documentation > Project Briefs
Client CommunicationBusiness > Project Management > Planning > Scheduling
WorkflowsBusiness > Project Management > Productivity > Time Management
Expectations ManagementBusiness > Project Management > Client Relations
Status ReportsBusiness > Project Management > Client Relations > Expectations Management
Project ManagementBusiness
Client RelationsBusiness > Project Management
PlanningBusiness > Project Management
DocumentationBusiness > Project Management
ProductivityBusiness > Project Management
FreelancingBusiness > Project Management
SchedulingBusiness > Project Management > Planning
Business

Welcome to Freelance to Founder0:00 – 0:55

Preston LeeHost

0:00

[upbeat music] 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/ask.

Preston LeeHost

0:23

I'm Preston Lee.

Preston LeeHost

0:23

I started freelancing 15 years ago, but from there I've built, grown, or sold a few successful businesses of my own.

Preston LeeHost

0:30

And w- together with my guest co-hosts, I wanna help you do the same.

Preston LeeHost

0:33

Uh, if you are interested in growing your business from being a freelancer to a founder, if you wanna scale beyond yourself, this show is for you.

Preston LeeHost

0:41

We're here answering your questions every single weekday, and today I'm joined again by a friend of the show, Austin Church.

Preston LeeHost

0:48

Austin is the founder of the Freelance Cake community for advanced freelancers.

Preston LeeHost

0:53

We'll talk more about that a little bit later in the show.

Preston LeeHost

0:54

But Austin, Austin, welcome.