This Operator-Turned Entrepreneur Raised Over $90 Million To Build The First Technology-Forward, Home-Services Platform

Shawn Weidmann’s story is one of transformation, resilience, and thoughtful decision-making. He is a fantastic operator-turned-entrepreneur who successfully raised $90M+ for his company, Zephyr, and scaled it to 300 employees.

Shawn’s journey illustrates the power of adaptability and the value of foundational leadership skills, from his military upbringing in Oregon to leading a cutting-edge roll-up in the home services industry.

In this insightful interview, Shawn explores the key moments that shaped his career, the lessons he’s learned along the way, and raising funding in challenging markets.

Listen to the full podcast episode and review the transcript here.

Military Foundations: Building Leaders

Shawn was born in Arizona and grew up in a family steeped in service, with his father in the Air Force. After years of moving, the family settled in Oregon, where Shawn spent most of his childhood.

Shawn’s military aspirations led him to West Point, a decision that would profoundly shape his future. Reflecting on his time in the Army, he describes the experience as a crash course in leadership.

“At 25 years old, I was responsible for 900 men and a $300M construction operation on an island in the Pacific. You don’t get that kind of responsibility anywhere else.”

These experiences instilled in Shawn the ability to lead, adapt, and communicate effectively across all levels of an organization—a skill set he would carry into the business world. He learned to interact with the equivalent of the factory floor–the soldiers–all the way up to the generals.

Shawn reveals how he is currently running a home services business, and he feels a connection with his technicians, who are very similar to the soldiers he worked with in the military – hard-working, practical, and very focused.

A Pivotal Shift: From Military to Civilian Life

The fall of the Berlin Wall marked a turning point in Shawn’s military career. As the Cold War ended, the nature of military service shifted, prompting Shawn to reevaluate his path. Seeking stability and new challenges, he transitioned to civilian life.

Shawn eventually enrolled at Stanford Graduate School of Business, where, surrounded by a culture of innovation and entrepreneurship, he began to explore the business world. Yet, he didn’t immediately identify as an entrepreneur, though he was exposed to great founders as his peers and classmates.

Jeff Skoll at eBay and Steve Jurvetsen at Jurvetsen Draper Fisher are two individuals Shawn still remembers. He knew so little about the civilian world that he showed up at a recruiting event, not knowing what an investment banker did.

Instead, Shawn leaned on his analytical skills. He entered the consulting world, joining McKinsey & Company, where he felt at home with several fellow West Pointers in the Cleveland/Pittsburgh office. He thought he could fit in there and understand how businesses work.

Shawn says his time there proved invaluable: “McKinsey taught me how to break down problems, communicate solutions, and work with exceptional leaders. Even today, as a CEO, I rely on those foundational skills to tackle challenges,” says Shawn. These skills helped make him a better operator.

Most importantly, Shawn learned to communicate with multiple levels through data, visuals, and words.

Learning from Legends: Operating Under Stewart Resnick

A turning point in Shawn’s career came when he worked for Stewart Resnick, the billionaire behind The Wonderful Company. Stewart’s hands-on mentorship taught Shawn the intricacies of running day-to-day operations and scaling businesses.

Here, Shawn absorbed lessons on efficiency, value creation, and operational excellence—wisdom that continues to guide him decades later. “That first year of owning a P&L was a baptism by fire. Stewart taught me how to truly manage a business. I still use his one-liners every day.”

After gaining operational experience at Teleflora and Public Storage, Shawn moved to Spring Education Group, where he oversaw a billion-dollar spree of acquisitions. This experience sharpened his ability to recognize patterns, integrate companies, and build cohesive operational systems.

Shawn learned a crucial factor that regardless of how unique founders may think their companies are, they are essentially more alike than different. When they were trying to buy schools, he saw that they basically operated in the same way and had similar metrics that made them successful.

For instance, Stratford School was similar to Public Storage or the Spring Education Group. What they were all doing was multi-unit retail. At the end of the day, the recruiting processes, marketing basics, the importance of local leadership and marketing, and digital marketing are similar.

When deploying capital, schools are similar to, say, an HVAC or a home services business. Ultimately, good leadership is the differentiating factor between a good and lousy company.

The Entrepreneurial Leap: Founding Zephyr

Despite years of working for established companies, Shawn eventually felt the pull toward entrepreneurship. Partnering with Juxtapose, a venture firm specializing in company creation, he founded Zephyr.

Shawn explains that Juxtapose does the base work of understanding the industry and doing commercial due diligence before deciding to build a company around it. Then, they recruit a CEO to build out the platform.

Shawn found that impressive and saw how Juxtapose derisked the Zephyr concept. He knew he could count on their support more than just the capital they contributed. He was also confident of leveraging his operating experience to build and run the company.

The Zephyr Business Model

Zephyr is a home services company with a mission to perfect the technician and customer experience. It is more than a roll-up; it’s a tech-forward, technician-first company. Shawn described the ethos behind the business:

“We focus on two people: the technician and the customer. Technicians are the backbone of our business, and we’re building systems that make their jobs easier and more efficient. For customers, we’re creating a trusted, transparent experience in an industry that hasn’t always prioritized them.”

By standardizing processes—from recruiting to technology—Zephyr has achieved operational cohesion. The company has already completed 15 acquisitions and raised over $90M despite launching during one of the most challenging fundraising climates.

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Zephyr is buying and building local businesses, leveraging most of its available capital. The objective is to perfect the home service experience from the inside out and use cutting-edge technologies.

As Shawn explains, traditionally, the customer has never been prioritized in this industry. Zephyr aims to change that by perfecting the interface with the technicians and their systems to provide a trusted consumer experience.

Shawn underscores that they are not trying to compile a bunch of assets quickly but are trying to build a team of operators and a great operating company. All the company processes are built on one technology stack, including sales and recruiting, and everyone has the same benefits plan.

This strategy may have resulted in slow growth in the initial stages, but it has allowed Zephyr to scale really fast and efficiently.

Fundraising in a Tough Market

Shawn’s fundraising journey wasn’t without its challenges. Raising capital in late 2023—a difficult time for startups—required persistence and a clear vision. Partnering with growth equity firms, Shawn successfully navigated these obstacles.

He secured the funding needed to expand Zephyr’s reach. He ultimately raised funds from two great firms, Elda River and The Pritzker Organization (TPO), and is excited to partner with them and tap into their expertise.

“You can’t always control the market conditions, but you can control how well-prepared you are. We leaned heavily on our operating experience and clear metrics to show investors our potential.” Zephyr is currently working with seven brands in 10 regions within the country.

The company is adding up several hundred million dollars in sales and is now operating with 300 employees. Shawn explains that the entire corporate team is virtual, and the company has a culture of collaboration and shared accountability for cultural and financial outcomes.

A piece of advice Shawn would give aspiring founders is to take more chances to raise their risk profile significantly and build a robust background.

Looking back, he recalls how people were skeptical about his moving from being the COO of Public Storage, a $50B company, to running a $90M+ in revenue organization at Stratford School. But he enjoyed the experience of taking it from that $90M+ to close to a billion dollars in revenues.

Looking Ahead: Zephyr’s Vision

Zephyr is poised to redefine the home services industry by integrating technology, prioritizing technicians, and delivering exceptional customer experiences.

Shawn’s career, built on a foundation of leadership, adaptability, and a commitment to excellence, serves as an inspiring example for those looking to make their own entrepreneurial leap.

Shawn’s story is a testament to the idea that it’s never too late to reinvent yourself. His path from military officer to corporate operator to founder shows that with the right mindset and skills, you can build something truly transformative.

Listen to the full podcast episode to know more, including:

• Shawn’s military background taught him to lead by handling high-stakes operations and connecting with people at all levels, lessons he applies in business today.
• From transitioning out of the military post-Cold War to navigating corporate roles and entrepreneurship, Shawn’s journey highlights the importance of evolving with changing circumstances.
• Shawn’s years at Stanford, McKinsey, and under Stewart Resnick prepared him to deeply understand businesses before taking the entrepreneurial plunge.
• Shawn emphasizes the importance of building scalable, efficient systems, starting with unifying technology stacks, sales, and processes.
• Shawn is transforming the home services industry from the inside out by prioritizing technicians and customer trust.
• His experience with acquisitions taught him to identify universal business drivers and focus on optimizing strong foundations.
• Working with Juxtapose allowed Shawn to launch Zephyr with financial and operational support, easing his transition into entrepreneurship.
  Shawn is excited to work with his new partners, Elda River and TPO, to drive the next growth phase.

 

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