Carly Pepin sits down with Tommy Lather, founder of Takeoff Monkey, to explore how automation, customer service, and operational simplicity helped transform a hands-on service business into a highly scalable company.
In this episode of Built for This, Tommy shares his unconventional journey from working in landscaping and estimating to building a rapidly growing takeoff services company that now processes hundreds of projects daily for contractors across the United States. Along the way, he taught himself software development and began building custom automations that dramatically improved efficiency across the business.
One of the biggest breakthroughs Tommy discusses is how Takeoff Monkey reduced overhead by roughly 70% through strategic automation, process optimization, and smarter systems. Instead of relying on huge teams or outside funding, the company focused on simplifying repetitive workflows, eliminating bottlenecks, and using AI-driven tools to scale sustainably.
Carly and Tommy also dive into the realities of managing remote teams across the United States and India, building strong culture inside a fully remote company, and why responsiveness and reliability have become the foundation of customer loyalty. Beyond operations, the conversation explores the emotional side of entrepreneurship, including founder loneliness, staying focused during growth, avoiding shiny object syndrome, and why persistence is often the biggest differentiator between success and failure.
This episode is a practical and honest look at building a modern business through systems, simplicity, and relentless consistency.
Key Themes:
Automation Should Simplify, Not Complicate: How removing repetitive tasks and operational friction dramatically improved efficiency and scalability.
Culture Starts With the Right People: Why attitude, integrity, and work ethic matter more than credentials alone.
Persistence Beats Perfection: Why long-term success often comes from refusing to quit and continuing to adapt over time.
About Tommy Lather:
Tommy Lather is a lifelong landscape construction professional, self-taught software developer, and founder of Takeoff Monkey, a company helping contractors streamline estimating and takeoff processes at scale.
With more than 25 years of experience across supply, operations management, sales, and estimating, Tommy developed a passion for building systems and processes that improve efficiency and simplify operations. Today, he combines industry expertise with automation and software development to help customers save time, reduce costs, and operate more effectively.
Memorable Quotes:
“You can’t teach someone to give a shit.”
“Just by not quitting, you will be successful.”
“We do what we say and we say what we do.”
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Host: Carly Pepin
Co-Founder & Host Built For This
West Coast Growth Advisors
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