May 23, 2025 · 29m · we-live-to-build
He Let a Filipino Team Run His 7-Figure Agency for 2.5 Years
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of We Live to Build, host Sean Weisbrot interviews Matthew Yaes, CEO of Extend Your Reach, discussing how he scaled a remote offshore staffing agency, overcame past entrepreneurial failures, and leverages modern AI tools for business acceleration and technical prototyping.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 41.9% of the talking time here. How this is scored →
Sean as informed peer 5.4 Guest teaching 2.3 Guest disagreement 1.1 Sean pushing back 1.1
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 9:49 Correcting the assumption about Filipino operator ambition
Yaes pushes back against Weisbrot's assumption that the employee left due to hidden ambitions for equity, clarifying that her role shrank because she specifically preferred individual contributor work over management.
Hardest push from Sean ▶ 8:58 Challenging the narrative on employee departureWeisbrot uses his 14 years living in Asia to challenge Yaes's explanation of his Filipino employee leaving, arguing cultural deference often masks unspoken career frustrations.
Biggest teaching moment ▶ 12:23 Explaining the breakdown in B2B booking conversionsYaes educates Weisbrot on why high click-through rates failed to produce calls, analyzing the distinct buying psychology and communication channels required for B2B staffing prospects.
Sean holds their own ▶ 13:27 Detailing the mechanics of podcast-driven salesWeisbrot demonstrates his strategic expertise by outlining how podcast interviews bypass cold outbound sales by establishing deep trust and generating qualified agency leads.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Forged by Adversity: Entering Entrepreneurship | 4 | 0 | 1 | 0 | Both host and guest bond over being thrust into entrepreneurship due to unfair corporate layoffs and toxic bosses. Weisbrot shares his personal experience living in China, creating a collaborative, empathetic dynamic. | |
| Analyzing Past Business Failures: Restaurants and E-Commerce | 5 | 2 | 1 | 0 | Yaes breaks down the failure modes of his prior restaurant chain and wedding e-commerce business during COVID-19. Weisbrot relates with an anecdote about his own investment in an FBA brand disrupted during the pandemic. | |
| Founding Extend Your Reach with Philippine Talent | 6 | 3 | 2 | 4 | Weisbrot leverages his 14 years living in Asia to question Yaes's narrative about his Filipino operator leaving, suggesting cultural deference and fear of rejection might have masked a desire for a bigger role. Yaes validates the cultural observation while clarifying she specifically preferred an individual contributor role. | |
| Structuring Executive Roles and Offshore Management | 5 | 4 | 1 | 2 | Yaes explains his rationale for hiring a US-based Asian operator to interface with clients while managing Filipino talent. Weisbrot digs into why inbound leads have lagged, prompting Yaes to dissect differences in B2B buying cycles. | |
| Utilizing Podcasts for High-Trust Client Acquisition | 7 | 1 | 1 | 2 | Weisbrot outlines his inbound podcast acquisition framework, citing how high-trust interviews eliminate cold calling and convert into high-ticket sales. Yaes agrees and explores how that model applies to business tear-downs. | |
| Mentorship Breakdowns and Entrepreneurial Honesty | 6 | 1 | 1 | 1 | Both speakers discuss offering blunt, tough-love mentorship sessions. Weisbrot shares how he gives candid pitch deck teardowns on GrowthMentor, noting founders rarely want their unprepared sessions published publicly. | |
| Mid-Roll Interlude: Supporting the Podcast | 5 | 3 | 1 | 0 | Following the mid-roll call to action, Weisbrot and Yaes discuss the dynamics of nominal friction fees to eliminate ghosting and filter out unserious clients. | |
| Orchestration vs Execution: The Entrepreneurial Shift | 5 | 3 | 1 | 0 | Yaes elaborates on shifting from hands-on execution to orchestration and team assembly as the key to scaling. Weisbrot affirms this insight and mentions his own approach to delegating weaknesses. | |
| Vibe Coding and AI-Powered Business Acceleration | 6 | 4 | 1 | 1 | Weisbrot and Yaes discuss vibe coding and rapid prototyping using tools like Replit, Cursor, and ChatGPT. They note that while AI lowers technical barriers, founders still need core business judgment to build viable products. |
Statements from this episode (14)
Yahes: Many people pursue entrepreneurship because it is thrust upon them
“And I bet you, there are a lot of people who are. Just like us who maybe wanted to be an entrepreneur, but it was kind of thrust upon them, right? Where you said sink or swim, buddy, what are you going to do? Sit there and cry. Get after it.”
Yahes: Scaled restaurant chain to 14 locations before bad investment forced exit
“We had 14 locations in four years from concept, but once we took the bad money, things, I left and things just didn't go the way they should have.”
Yahes: Multimillion-dollar wedding e-commerce portfolio collapsed to zero during COVID-19
“So what was a multimillion dollar business became I like to say I grew it to zero. Wasn't exactly zero, but it didn't make sense to keep it open and it wasn't profitable when you start factoring in people and advertising.”
Yahes: A single Filipino manager autonomously ran his $5.5M e-commerce business
“Specifically one person that was running the e-com, I said to her, everyone is always fascinated that I found some of the Philippines to fully run a business at the time is doing, I think five and a half million dollars where I was not involved in the operatio…”
Yaes: Remote Philippine Team Ran Staffing Agency For 2.5 Years
“So I had that business run on its own for
Two and a half years, I would say, while I was involved in a financial technology company, which I got involved in because of my staffing business, that financial technology company scaled massively.
It was a point in …”
Weisbrot: Asian workers struggle to express themselves and defer to Americans
“And I found that Asians are really bad at expressing themselves because they're afraid of being rejected. It's just, you know, plus they also defer to Americans.”
Yaes: Filipino offshore teams operate in a hierarchical 'boss is God' culture
“When I talk to my team, it's there in a I'm boss, I'm God culture, and you have to really pull things out of them.”
Yaes: Scaling Offshore Agencies Requires American Executives to Close US Clients
“And it made more sense to have an American who also has inroads with businesses in the United States. So understands the psyche, understands what they need and understands how to talk to the business people at a very high level.”
Yahes: Staffing agency paid ads generate high clicks but zero calls
“In this case, my, I've advertised a ton. The click through rates are very good, but the book a call rate is non-existent.”
Weisbrot: Coach generated $250K in sales from her first 60 podcast guests
“She launched 60 episodes, like in the very beginning, she pre-recorded 60 episodes, and from those 60 episodes, she booked a quarter million in sales off of the guests.”
Yaes: Requiring refundable upfront deposits filters out unserious clients
“It's also a good customer filtering tool. Someone can't give you, it was 350 dollars, right? For something that's two to 3000 a month for, you know, full-time staff. If you can't deposit a couple hundred dollars, well, you're going to get the money back. You'r…”
Weisbrot: Only ~2% of Podcast Guests Actually Promote Their Episode
“A hundred percent of the people promise to promote it. Probably two percent of them actually promoted.”