How Did Two Best Friends Build a $25K/Month AI Agency With Tech Skills?

TL;DR

Jake and Kade grew their AI automation agency to $25K in monthly revenue by testing acquisition channels, winning clients through Upwork, scaling cold email, and developing practical technical skills. After joining Maker School, they landed a $7,500 win in their first month and climbed from roughly $10K to $25K. Read on for their lessons about outreach, niches, acquisition economics, and sustainable growth.

Transcript

And we were very much in the mindset that we have to make this niche work. If we pivot, we're failures. And we just kept pushing and pushing and pushing. And it wasn't until the start of this year, 2025, that we actually took a step back and said, well, maybe we're not failures if we pivot to a different niche, but maybe we're just not pigeon holin... Read More

Key Insights

• The agency reached $25K in monthly revenue after previously experiencing months of roughly $2K or $3K. The founders described revenue growth as approximately doubling month over month after joining Maker School, with an earlier month near $10K.
• Upwork applications produced the founders' fastest early wins even though they had not initially considered the platform an important acquisition channel. Its lead and customer acquisition costs were lower than paid advertising, making it an effective complement to cold email.
• The best acquisition channel is the one that combines low customer acquisition cost, high lifetime value, consistency, and scalability. Platform reputations should not determine strategy because price-sensitive prospects can appear through Upwork, cold email, advertising, and other channels.
• Technical ability creates practical leverage in an automation business. The discussion emphasizes that even a small amount of technical skill can make a founder considerably more capable when pursuing client work, delivering automation services, and identifying commercially useful opportunities.
• A pivot is not necessarily evidence of failure. Jake and Kade spent substantial time forcing one niche because they believed changing direction would mean they had failed, but they reconsidered that belief at the start of 2025 and stopped restricting themselves unnecessarily.
• Customer conversations are more urgent than perfect planning for an early agency. Founders do not need a fully developed ideal customer persona, mission, values, or go-to-market strategy before beginning outreach, especially when the immediate goal is finding customers and validating demand.
• Full-time entrepreneurship requires self-imposed structure because there is no manager controlling the workday. Kade described gaining complete control over his schedule after leaving retail, while also recognizing the greater maturity and personal accountability required to complete necessary work.
• Revenue milestones do not automatically transform daily work or create a lasting feeling of success. Even after reaching the founders' long-held $20K to $25K goal, their routine still involved Upwork applications, cold email optimization, and ordinary operational work.

Questions & Answers

Q: How did Jake and Kade grow their AI agency to $25K per month?

They tested client acquisition channels, used Upwork for fast early wins, and continued optimizing cold email. After joining Maker School, they landed a $7,500 win in their first month and described their revenue as roughly doubling month over month, rising from about $10K to $25K.

Q: Why did Upwork work well for their automation agency?

Upwork generated some of their fastest early wins, despite not initially being viewed as an important acquisition channel. It also produced lower lead and customer acquisition costs than paid advertising, making it an effective complement to their scalable cold email efforts.

Q: How should an AI agency choose a client acquisition channel?

The agency should compare channels based on customer acquisition cost, client lifetime value, consistency, scalability, and revenue contribution. Jake and Kade’s experience suggests concentrating resources on the channels with the strongest measurable economics instead of relying on assumptions about platforms.

Q: Does an AI agency need a perfect niche before starting outreach?

No. Jake and Kade initially forced themselves to remain in one niche because they believed pivoting meant failure, but they reconsidered that belief at the start of 2025. They stopped pigeonholing the agency and became more willing to follow evidence from the market.

Q: Do new agency founders need a complete go-to-market strategy first?

No. The discussion argues that founders do not need a polished ideal customer persona, mission, values, or complete go-to-market strategy before contacting prospects. The immediate priority is to start talking to people and use those conversations to test demand.

Q: How important are technical skills when building an automation agency?

Technical ability creates practical leverage when pursuing and delivering automation work. The discussion emphasizes that even a small amount of technical skill can make a founder considerably more capable and help reveal commercially useful opportunities.

Q: What changes after an agency reaches $25K in monthly revenue?

The remuneration changes, but the daily routine may feel much the same. Jake and Kade still submitted Upwork applications, optimized cold email campaigns, and completed ordinary work, even after reaching the $20K to $25K target they had associated with success.

Q: What revenue path did Jake and Kade follow before reaching $25K per month?

Before Maker School, they experienced rough months of roughly $2K or $3K. After joining, they secured a $7,500 win during their first month and described revenue progressing from around $10K to a record month of $25K.

Summary & Key Takeaways

• Jake and Kade grew their automation agency from rough months of roughly $2K or $3K to $25K in monthly revenue. After joining Maker School, they secured a $7,500 win during their first month and then approximately doubled revenue month over month, progressing from around $10K to their record month.

• Their fastest early results came from Upwork applications, a channel they had previously overlooked while relying mainly on cold email and paid advertising. Upwork offered lower lead and customer acquisition costs than advertising, while cold email remained useful as it scaled. The broader lesson was to evaluate channels by measurable economics.

• The founders initially felt committed to making one niche work because they associated pivoting with failure. In early 2025, they reconsidered and stopped pigeonholing the agency. Their experience suggests that founders do not need a perfect customer profile, mission, values, or go-to-market plan before speaking with prospects and testing demand.