Freelancing Origins of an 8-Figure Agency episode artwork

EPISODE · Jan 23, 2026 · 1H 39M

Freelancing Origins of an 8-Figure Agency

from That Agency Show · host Kyle Sulerud and Drew Carrell

This episode of That Agency Show covers the journey of starting a career as a freelancer, detailing the progression from low-paying gigs and unprofitable businesses to finally cracking the $10,000/month barrier. https://thatagencygroup.comhttps://usejuiced.comKey Sections:00:00 Opening teaser and episode setup01:50 Kyle: Early life, college, and chasing passion vs career07:24 Starting first business: foreclosure maintenance11:13 First business struggles and ultimate failure16:38 Pivot to junk removal with a used U-Haul17:23 Marketing to find junk removal customers18:47 Juggling full-time job, school, and the business19:16 Going all-in: quitting the call center21:18 Mastering Google Ads during the winter slowdown24:13 Fiverr gig: $5 ad setups and first Google Ads offers29:50 First recurring fee client and realizing the value of recurring income34:04 Hiring a VA to help scale, first team member38:12 Upgrading to experienced VA from the Philippines (still with the company today)42:48 Big milestones: $480 and $4,000 clients48:56 Selling junk removal to focus on Google Ads53:03 Using Facebook Ads to grow a community and generate leads58:12 Stabilizing at $10,000/month and key learnings01:00:19 Transition from freelancer to agency: hiring for client support01:01:05 Evolving the offer and niching down (Kyle & Drew)01:02:05 Drew: personal journey, early work experience, and discovering marketing01:13:25 Early affiliate mistakes, quitting, outreach, first clients01:25:41 Delivery challenges, COVID wins, joining AdLeg01:33:47 Tragedy leads Drew to fully focus on AdLeg

This episode of That Agency Show covers the journey of starting a career as a freelancer, detailing the progression from low-paying gigs and unprofitable businesses to finally cracking the $10,000/month barrier. https://thatagencygroup.comhttps://usejuiced.comKey Sections:00:00 Opening teaser and episode setup01:50 Kyle: Early life, college, and chasing passion vs career07:24 Starting first business: foreclosure maintenance11:13 First business struggles and ultimate failure16:38 Pivot to junk removal with a used U-Haul17:23 Marketing to find junk removal customers18:47 Juggling full-time job, school, and the business19:16 Going all-in: quitting the call center21:18 Mastering Google Ads during the winter slowdown24:13 Fiverr gig: $5 ad setups and first Google Ads offers29:50 First recurring fee client and realizing the value of recurring income34:04 Hiring a VA to help scale, first team member38:12 Upgrading to experienced VA from the Philippines (still with the company today)42:48 Big milestones: $480 and $4,000 clients48:56 Selling junk removal to focus on Google Ads53:03 Using Facebook Ads to grow a community and generate leads58:12 Stabilizing at $10,000/month and key learnings01:00:19 Transition from freelancer to agency: hiring for client support01:01:05 Evolving the offer and niching down (Kyle & Drew)01:02:05 Drew: personal journey, early work experience, and discovering marketing01:13:25 Early affiliate mistakes, quitting, outreach, first clients01:25:41 Delivery challenges, COVID wins, joining AdLeg01:33:47 Tragedy leads Drew to fully focus on AdLeg

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Freelancing Origins of an 8-Figure Agency

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This episode was published on January 23, 2026.

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This episode of That Agency Show covers the journey of starting a career as a freelancer, detailing the progression from low-paying gigs and unprofitable businesses to finally cracking the $10,000/month barrier....

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