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Just Go Grind Podcast: Jeremy Yamaguchi

Just Go Grind Podcast: Jeremy Yamaguchi

A conversation with the founder of Lawn Love and CEO of Cabana

Erika Braza & Justin Gordon
May 13, 2025

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Jeremy Yamaguchi is a lifelong entrepreneur.

The founder and CEO of Cabana Pools got his start selling balloon animals at age 12 and, from then on, he never stopped building.

In his teens, he launched a design and development agency that grew into a full-blown growth marketing firm. And by his early 20s, he had bootstrapped a successful housekeeping marketplace, which he later sold to private equity, dodging the wave of overfunded, unsustainable competitors that crashed shortly after.

Next up was Lawn Love, an on-demand lawn care platform he built into a national brand and ran for nearly eight years. Jeremy has always gravitated toward “high-suck” industries because he knows how to bring order through smart software and sharp marketing. He’s less about hype, more about execution.

Today at Cabana he’s bringing the same marketplace and tech-driven playbook to the world of residential pool services, another old-school industry ripe for modernization.

Listen to Jeremy’s interview on YouTube, Spotify, or Apple Podcasts.

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Rapid testing and data-driven validation to pick the next ventures. Before starting Lawn Love, Jeremy tested three business ideas (lawn care, pool cleaning, and personal training) simultaneously by building landing pages and driving traffic to see which had the best customer acquisition metrics. Lawn care won, not because of passion, but because of customer demand and scalable economics.
Be strategic about timing and competition. Jeremy exited his first home services startup just before well-funded Silicon Valley competitors entered the space. While they burned through capital and ultimately struggled, he sold his bootstrapped business to private equity at the right time, demonstrating sharp awareness of market dynamics and risk mitigation.
Jeremy values intrinsic motivation over external validation. When he applied to Y Combinator he didn’t pin his hopes on it, since he believed that true founders build regardless of outside recognition. A long-term grit mindset beats short-term credentials.
Be intentional about investor selection. Rather than chasing a single big check, Jeremy chose a “party round” to bring in a diverse mix of operators and angels who could offer strategic value beyond capital, turning his cap table into a growth engine.
Prioritize channels that align with user intent. Jeremy focused on SEO and SEM early on, recognizing that customers actively searching for home services were more valuable than passive social media users, leading to efficient, scalable growth.
Jeremy treats customer service as a core growth lever. He built in-house support early because he believed that fast, empathetic help not only retained users but turned them into advocates, creating organic word-of-mouth that compounds over time.
A hybrid of venture growth and private equity discipline was Cabana’s business strategy. To Jeremy, acquiring and vertically integrating home service businesses using custom-built software can yield venture-scale returns without traditional venture risk, creating a unique investment opportunity that’s increasingly gaining mainstream attention.
Some of the best hires may not look great on paper. Jeremy learned not to over-index on pedigree. One of his best engineers had never worked at a big tech company or gone to a name-brand school, but could out-execute just about anyone. He focused on finding people who could actually build, not just talk about it.
Bootstrapping builds discipline that venture money can’t replace. Before raising any capital, Jeremy bootstrapped multiple businesses, so he learned how to make every dollar count. That scrappy mindset stayed with him even after he raised funding for Lawn Love. He’s wary of founders who rely too heavily on outside capital to prove product-market fit or fund early growth: “Raising money should accelerate what’s working, not validate something that isn’t.”