How a Surfer Built One of America's Fastest-Growing Software Companies episode artwork

EPISODE · Jul 3, 2026 · 22 MIN

How a Surfer Built One of America's Fastest-Growing Software Companies

from Legends N Leaders · host Ben Weiss

In this episode of LegendsNLeaders, we sit down with Kai Stone, founder and CEO of StoneSystems.io, the software platform helping contractors streamline their operations, grow faster, and build more profitable businesses.Growing up in Hawaii, Kai never followed a traditional entrepreneurial path. What started as helping a few local builders solve operational challenges evolved into one of the fastest-growing software companies serving the construction industry. Along the way, Kai built a multi-seven-figure business by combining innovative technology with an authentic, no-nonsense approach to leadership and entrepreneurship.Known for his bold perspectives and willingness to challenge conventional thinking, Kai shares what it really takes to build wealth, create freedom, and scale a business without losing sight of your values. We also discuss leadership, marketing, personal branding, and why some of the biggest opportunities come from modernizing industries that have been overlooked by technology.In this episode, you'll learn:* How Kai built a multi-seven-figure software company from the ground up* Why the construction industry is ripe for innovation* The mindset required to build wealth and long-term freedom* Lessons on leadership, authenticity, and personal branding* Advice for entrepreneurs looking to scale without compromising their visionWhether you're a founder, entrepreneur, business owner, or someone looking to build a life on your own terms, this conversation is packed with practical insights on business growth, resilience, and creating lasting success.#Entrepreneurship #Business #Leadership #Construction #Software #Startups #PersonalBrand #Innovation #KaiStone #LegendsNLeaders

In this episode of LegendsNLeaders, we sit down with Kai Stone, founder and CEO of StoneSystems.io, the software platform helping contractors streamline their operations, grow faster, and build more profitable businesses.Growing up in Hawaii, Kai never followed a traditional entrepreneurial path. What started as helping a few local builders solve operational challenges evolved into one of the fastest-growing software companies serving the construction industry. Along the way, Kai built a multi-seven-figure business by combining innovative technology with an authentic, no-nonsense approach to leadership and entrepreneurship.Known for his bold perspectives and willingness to challenge conventional thinking, Kai shares what it really takes to build wealth, create freedom, and scale a business without losing sight of your values. We also discuss leadership, marketing, personal branding, and why some of the biggest opportunities come from modernizing industries that have been overlooked by technology.In this episode, you'll learn:* How Kai built a multi-seven-figure software company from the ground up* Why the construction industry is ripe for innovation* The mindset required to build wealth and long-term freedom* Lessons on leadership, authenticity, and personal branding* Advice for entrepreneurs looking to scale without compromising their visionWhether you're a founder, entrepreneur, business owner, or someone looking to build a life on your own terms, this conversation is packed with practical insights on business growth, resilience, and creating lasting success.#Entrepreneurship #Business #Leadership #Construction #Software #Startups #PersonalBrand #Innovation #KaiStone #LegendsNLeaders

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How a Surfer Built One of America's Fastest-Growing Software Companies

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This episode was published on July 3, 2026.

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In this episode of LegendsNLeaders, we sit down with Kai Stone, founder and CEO of StoneSystems.io, the software platform helping contractors streamline their operations, grow faster, and build more profitable businesses.Growing up in Hawaii, Kai...

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