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From Landscaper to Software Builder: Tommy Lather’s Unexpected Journey
In this episode of Built for This, 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.
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:
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.”
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.
Connect with Tommy Lather:
http://www.takeoffmonkey.com
https://www.instagram.com/takeoffmonkey
View all episodes
By Carly PepinIn this episode of Built for This, 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.
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:
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.”
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.
Connect with Tommy Lather:
http://www.takeoffmonkey.com
https://www.instagram.com/takeoffmonkey