Operator-Turned Entrepreneur, Shawn Weidmann, On Raising 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.

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 from investors like Elda River and The Pritzker Organization.

In this episode, you will learn:

• 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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About Shawn Weidmann:

Shawn Weidmann has diverse work experience, with a focus on leadership roles in various industries. Shawn is currently the CEO and Co-Founder of Zephyr, a home services platform that aims to enhance the experience for trade technicians and homeowners.

Prior to this, Shawn served as a Board Member at StorHub Self Storage and OAK PAPER PRODUCTS. He also held positions as a Board Member and Advisor at an undisclosed company.

Shawn’s previous roles include CEO of Spring Education Group, CEO of Stratford School, and COO of Public Storage. Additionally, he served as the President of Teleflora and Vice President – Strategy at Roll International. Shawn started their career as a Managing Director at EHS Partners.

Shawn earned a Bachelor of Science in Civil Engineering from the United States Military Academy at West Point in 1985. He later pursued an MBA in General Management from Stanford University Graduate School of Business, completing the program in 1995. Before higher education, he attended Wilson High School from 1977 to 1981.

Connect with Shawn Weidmann:

• LinkedIn
• Crunchbase
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty. Hello, everyone, and welcome to The Deal Maker Show. So today we have a fantastic operator turned entrepreneur. um you know We’re going to be talking about building, scaling, financing, all the good stuff that we like to hear. I mean, on their end, you know they’re doing amazing. They raised the over $90 million, 300 employees, but it’s been quite the journey.

Alejandro Cremades: and We’re going to be talking about you know things like fundraising during challenging challenging markets. ah and and Basically, you know why he decided you know to start, let’s say, a company versus you know doing more like the established companies like he was doing before. Again, a lot of stuff that we’ll be covering. Brace yourself for a very inspiring episode. and Without further ado, let’s welcome our guest today, Sean Whiteman. Welcome to the show.

Shawn Weidmann: Thank you, Alejandro. Thank you very much for having me.

Alejandro Cremades: So originally born in Arizona, and your dad was in the Air Force, so you guys moved quite a bit. So how was life growing up for you?

Shawn Weidmann: it was it was It was great. i um you know we We settled in Oregon after a couple of years, so I really consider myself an Oregonian to this day, spending from years 2 through 18 in Oregon.

Alejandro Cremades: So obviously, you’re that in the Air Force. You wanted to eventually do something along the same lines, which you eventually did because you went to West Point. And then from there, you know you went at it. I guess, how do you think your leadership skills um shaped up during that day phase in your life?

Shawn Weidmann: That’s a great question. i think I think many of your, you said you’ve had some military guys on the show before. I think they would all probably tell you roughly the same thing, that that um that military experience is so foundational for you as a leader. You learn at such an early age to take on huge responsibilities, be responsible for people, learn how to be a leader and a follower.

Shawn Weidmann: It’s just, you you don’t get that in any other job. I mean, think about, you know, I think about when I was 25 years old, I was in charge of 900 guys and a $300 million dollars construction operation on an island of the coastal Pacific. You know, it’s like, you just don’t get that sort of thing anywhere else. And so it really, really kind of builds those, lets you make a lot of mistakes as a leader, um makes you kind of understand how to relate to, you know, people from below, it you know,

Shawn Weidmann: the equivalent of the factory floor, your soldiers, all the way up to having to brief generals and understanding how to how to alter your style and and and connect with people at all those various levels. Really, you know for me, it’s come full circle. Now I’m kind of running a home services business and my technicians feel a lot more to me like soldiers than they do some of the other things I’ve done in my life. So it’s it’s been a great experience.

Alejandro Cremades: At what point did you realize, say, maybe you know I got to get into business school and and get to learn a little bit what what what is this business world about?

Shawn Weidmann: ah ah that’s it That’s a good question. I’ll tell you exactly when it was, when the wall fell. and the bur will ah a you know My war that we had prepped for, you know we didn’t know kind of what the my post-9-11 world would look like, but my war was the Cold War. And when that when the wall fell, life changed for the military. And it suddenly became not, I had learned a lot. and i And I actually really loved it, thought I was going to make it a career.

Shawn Weidmann: And suddenly it just become a lot less enjoyable of a place and you know decided to get out and try the try the civilian world, you know thinking we would have a you know nice stable life. And you know me and my wife, I think, have moved 16 times since we got out of military. So it’s been a it’s been kind of a wild ride.

Alejandro Cremades: That’s amazing. Now, in your guys’ case, I mean, you went to Stanford, and Stanford is the land of innovation, you know on entrepreneurship. you know Some of the best entrepreneurs have come out of that program. So you took a little bit of longer and to get going as an entrepreneur. you know I’m sure you had a lot of classmates, you know a lot of people that you met that went on and and did their own thing. So what do you think, you know why it took you so long?

Shawn Weidmann: Yeah, because I never really considered myself an entrepreneur. I was ah you know coming out of out of Stanford, having been mostly spent most of my career in the military. i I thought I had to figure out what this business world is about. i like you know someone One of my classmates was Jeff Skoll, who was employee number one at eBay, um you know and helped build that. You got Steve Jurvitsen, Jurvitsen Draper Fisher.

Shawn Weidmann: some really great entrepreneurs in my class. I wasn’t that guy. um I needed to figure. I didn’t I remember going to a recruiting event when they were talking about investment bankers. I didn’t even know what an investment banker was. So it’s like I so I went consulting the consulting world. Partially because there was a lot of West Pointers and at McKinsey that recruited me there made me feel like I could learn fit in and learn things there. So It took, you know, i’m I’m a slow learner, I guess, Alejandro. I needed to kind of understand the business world, understand how businesses tick, what makes them work. um And then, you know, i I found myself through my consulting days always really enjoying yeah working with the operators more, the business leaders more than coming up with the grand strategies and everything. I like working with them and making

Shawn Weidmann: um making things happen. So I remember one day, one of my clients goes, so when are you going to get a real job? And I kind of laughed and said, no, I got a real job. you know We do good things and make good money. And he’s like, yeah, happy come on. That’s not a real job. And that’s when I decided to it was time to go ah be more of an entrepreneur. Went to work for one of the greatest entrepreneurs in history, a guy named Stuart Resnick in Los Angeles.

Shawn Weidmann: and really learned how to how to run and build businesses from him.

Alejandro Cremades: And before before talking about that, i want to talk I want to talk about one thing specifically, you know, just to double click on the consulting years at McKinsey. At McKinsey, I find that it gives you an amazing training and basically on being able to grab one big problem and breaking it down into little problems that you get to tackle to to make it a little bit easier to go about problem solving. What kind of training or or or experience do you think that those years at McKinsey gave you to be an effective operator down the line?

Shawn Weidmann: Yeah, McKinsey was I don’t want to, you know, downplay that that McKinsey taught me so much. You’re right. The problem solving, the breaking down a problem, the commute and then yeah also communicating the solution and and getting people on board and how you communicate. That’s that becomes, you know, I feel like every time I’m doing a board deck now or something like that, I fall back to those McKinsey days and just how you How you communicate with multiple levels through through data, through visuals, through words. um Communicating how you’re going to solve that problem is a big part of, a I think, what you learn at McKinsey. Besides making the great network and look at you know getting to watch and work with a bunch of amazing leaders. ah But you’re right, that problem solving,

Shawn Weidmann: that analytical approach, how you use data to communicate the solution, that’s it is all really foundational. And something, ah frankly, it’s interesting, I find myself with, even in this world, that’s one of the few things that I end up doing as a CEO is helping my team do that sort of stuff. We just had a great board meeting, and you know all that kind of foundational stuff just helps me put that stuff together.

Alejandro Cremades: So let’s talk about, a like they ask you, getting getting a real job or a real role. So obviously you have the opportunity here to work with an amazing you know leader. I guess, how was that for you and and and obviously getting your feet wet now as an operator too?

Shawn Weidmann: ae Was it this he was a yeah, he was a great guy this guy who’s he was A green name now. It’s now called the wonderful company, but the guy is you know, he’s got DJ water um Teleflora a bunch of agricultural businesses and you know sale self-made multi-billionaire and he just really taught me You know just the basics of how you how you how you build a business how you create value the guy had you know how you How you create value efficiently? um how you Manage the business on a day-to-day basis what things you ought to be looking for he’s I still find myself to this day and that was I

Shawn Weidmann: almost 20 years ago I started working for him. I still spout off his business one-liners almost on a daily basis, because they were such pearls of wisdom. But I tell you, this is it is a tough, I think everybody probably feels that transition may be tougher for me than others, but yeah you know that first that first P and&L you’re responsible for, and you go from like just advising and thinking about it to you know having to put things in place and then owning the result, like truly owning the results. That was a um that first year was was some interesting times. That’s always, ah especially with somebody who’s successful as him. He would own that business for 20 years. he he He really taught me a lot.

Alejandro Cremades: So in your case, you know after after that, I mean, you you went to Teleflora, you did stuff there with him. Then you went to Public Storage. But one thing that I want to ask you about is, you were recruited eventually ah for Stratford School, and that ended up becoming Spring Education Group. And there you guys did a ton of acquisitions. I mean, a ton. I mean, we’re talking about a literally deploying a billion ah to to really acquire these companies.

Alejandro Cremades: I’m sure that that also gave you a tremendous amount of perspective to see you know on on pattern recognition on companies that work, companies that don’t work, also integration teams. What were some of the biggest takeaways that you took from but like that crazy you know spree of of of acquisitions?

Shawn Weidmann: um The good question. One of the things I’d say is businesses are more alike than different. I think everybody likes to talk about how unique their company is or their industry or their that really when you come down, you know, I go back to some of my my, you know, the one liners that Stewart taught me. But, you know, at the end of the day, you know, like when we were when we were buying all these schools, all the schools basically operate the same. They have the same metrics. They have the same.

Shawn Weidmann: Things that make them successful and they’re very similar to public storage when I really wanted to. Annoy the educators at spring. I would say, hey, all we’re really doing is multi unit retail um and they would, of course, it was much. We had a much more important mission maybe then self storage, but at the end of the day.

Shawn Weidmann: recruiting processes are the same, the basics of how you market, the importance of local leadership, um the importance of local marketing ah combined with digital marketing. It’s like there’s all these things are very, very similar. When you start deploying that capital and looking at businesses, like understanding how successful that business is and what you can underwrite, it’s you know there’s a whole lot more that is the same than different. and i and i you know And schools are very similar to HVAC businesses. you know how you And home services business, when you look at the kind of the basics of how the quality of that local leader, how they’ve run their business, even if they haven’t run it very sophisticated, you can tell if they’re running a good business or not. yeah

Shawn Weidmann: you know a whole lot easier to make a good business great than a lousy business good.

Alejandro Cremades: That’s amazing. Now, in your case, you know this was the most immediate step you know after spring education to really get going with becoming finally an entrepreneur.

Shawn Weidmann: Yes.

Alejandro Cremades: So what wanted needed it to happen for you to be like, okay, let’s go.

Shawn Weidmann: A big part of that was i I’ve teamed up with a a great venture firm, Juxtapose was my initial funding and they are, at yeah and I think you’ve done some, and you may have done some ah interviews with some of their other CEOs, but they are an amazing firm and they, I was really drawn to them, they are not your traditional venture firm, they really, they do company creation. so they had done a lot of the kind of the base work in terms of understanding the industry doing a lot of the commercial due diligence on the industry and deciding they wanted to form a company around it. So they decided to form a company and then they go out and get a CEO to help build out that platform. So for me, that helped D risk. And I, so when I say D risk, not just a financial risk, but more of a,

Shawn Weidmann: an emotional risk and, ah you know, because they put a lot of support around me to make it happen. And besides just the capital that they contributed. So that really helped me make that launch into entrepreneurialism and um and feel good about it. And it just feels like, you know, when you think about what a great kind of senior thesis for me as I get to this stage in my career to start up a company that’s gonna be a great, ah you know, pull on all that great operating experience I have and be able to, so you know, build it around the things I’ve learned and create something that’s going to, you know, I think last for a long time.

Alejandro Cremades: So then what are you guys up to here? What are you guys ultimately what’s the business model? How are you guys making money?

Shawn Weidmann: Yeah, so we are, you’d recognize this as a roll up. I think we’re very different. We can talk about some of that. But, you know, our, we are, we are buying up and partnering with local brands, great local brands, and and helping them ah building around those local brands. We’ve done, well, I think when we first started this, we said we had done 12 acquisitions. We have done 15 today because we closed another few in the last few weeks. um So we’re buying and building um these local businesses, and that’s most of what the capital is being used towards.

Shawn Weidmann: um But what we’re really trying to do is is we talk about we’re perfecting the the home service experience from the inside out. There’s a couple of elements to that, and I’ll take it in reverse order of perfecting from the inside out. What we really wanted to build the company around was we wanted to make it very tech focused, and I you mean that in two ways. technic Technology, like you might think, and we’re putting lots of interesting technologies into play, and and we’re very tech forward in that way, but we’re also technician focused. um You know, in my army days, we used to say there’s infantry and infantry support, and the company, now we talk about there’s only two jobs. There’s technicians and technician support, and technicians are the only ones that make us money. And so we’re actually building it with the tech everything with the technician in mind, making them

Shawn Weidmann: making their job better, making their job easier, making it so they’re more effective. Not just to be good guys. I mean, we think we are good guys, but it’s to, we have a really, there’s not enough technicians out there. We’re not producing enough of them. So making them ever more efficient is big, is very important. But also from the inside out, there’s two people in the inside of the home that you need to really optimize around the technician who’s doing the selling and the customer.

Shawn Weidmann: And this is an industry where the customer has not always been placed first. There’s a lot of horrible stories out there around you know you know grandmas being sold, ah you know things they don’t need. We don’t want that. We want to really perfect that interface with the technician and their systems that we’re putting into place and really having that trusted consumer experience.

Shawn Weidmann: And then around that we’re just trying to build a really great operating company. and We’re not just trying to slap together a bunch of assets as fast as possible. We’re trying to build this my team as a team of operators um and we’re going to we’re building a great operating company we have.

Shawn Weidmann: Everything is built, you know, we’re on one technology stack. we We have one sales process. We have one recruiting process. Everybody’s on the same benefits plan. Things like that that allow you to maybe go a little slow in the beginning, but allow us to scale really fast and really properly.

Alejandro Cremades: and Just out of curiosity, how did you guys come up with the name of the company?

Shawn Weidmann: Great question, actually. And it’s a funny story because juxtapose always When they do come up with a concept, they always have a project name. And this one was called Zephyr. So then we, which means a warm West wind in Greek.

Shawn Weidmann: And then we we went through all the, you know spin but you know, spent money on getting a brand firm to do a bunch of research for us and consumer focus.

Shawn Weidmann: And then we came down to Zephyr was the best name.

Alejandro Cremades: That’s amazing.

Shawn Weidmann: It was kind of funny, but i yeah, it’s it’s a great name.

Alejandro Cremades: So in your guys’s case, you’ve raised now about $90 million for Sephir. And I want to ask you, how was the journey of of going through those different financing rounds?

Shawn Weidmann: Yeah, that was ah so it’s really it’s really only been let’s call it two rounds because there was an initial with juxtapose. And then so then we spent the last we started raising money last up last fall, which was just a can’t always control your circumstances. But that was a horrible time, as I’m sure many you know everybody tells you to to raise money. So it was kind of a challenge. We um ah we were kind of that stage where going out to growth for growth equity firms was kind of the right play. And, you know, it was just a tough environment. You know, eventually came up with two great partners, TPO and Elder River. um And but you just it was, it was, it was a

Shawn Weidmann: It’s like doing a base i don’t know doing a house renovation. It always takes twice as long and costs you twice as much as you think it’s going to. But it was a challenge.

Alejandro Cremades: so then So then in that case, too, i mean obviously, when when you got these investors investing, they’re investing, too, in in a vision. right and and Not only that, you know also the customers, the 300 employees that you guys have. So if you were to go to sleep tonight, Sean, and you wake up in a world where the vision of Sapphire is fully realized, what does that world look like?

Shawn Weidmann: Yeah, I don’t even know. what I i and tend not to ti tether that to a um to a size. um to to you know Like I was talking about, we want to create a great operating company, not a great transaction. We think we’ll create a great transaction for current set of investors and follow-on investors by being a great operating company.

Shawn Weidmann: that would That’s what I would say is that we we would be um a great operating company that’s let’s call it you know somewhere in the neighborhood. We’re in we’re in five five regions right now. We’ve got seven brands, I’d say. We’re in 10 regions of a a the a country.

Shawn Weidmann: were ah you know several hundred million in sales but more importantly we’re a great operating company that technicians want to be part of and we are generating a nice unit level margins and creating great careers for all of our employees.

Alejandro Cremades: That’s beautiful. And how have you guys gone about culture too? um you know With 300 employees, you know how have you guys gone about building the fundamental pillars of culture for the business? And then how do you go about embracing them?

Shawn Weidmann: Yeah, that is, and and because, you know, my whole corporate team is a is a virtual team. I mean, everybody, we don’t get to sit around looking at each other and talking other than through this sort of medium every day. So we really try. I just got back from if you hear a little scratch in my throat, I just got back from last week we had a year and gathering of all of our local GMs. And that’s really the core of how we try to create that culture is this partnership with local business leaders, half of whom are former owners that we’ve acquired and they bought into the vision and they wanted to stay on and operate. um And so we really try to enforce it through them in and in really creating a system of both collaboration, but

Shawn Weidmann: shared accountability to each other ah for kind of the cultural and financial outcomes that we’ve all committed to for ourselves and our investors.

Alejandro Cremades: That’s amazing. so I want to ask you something. We’re talking about the future before. I want to talk about the past, but doing so with a lens of reflection. If you were able to go back in time,

Alejandro Cremades: And let’s say you’re coming out of Stanford and you, let’s say you were to follow you know the path of other you know classmates and start a company right away. Given all your years of having been, let’s say, a consultant, an operator, now an entrepreneur, successful entrepreneur,

Alejandro Cremades: If you were to be there in front of that younger Sean and be able to give that younger Sean one piece of advice before launching a business, what would that be and why, given what you know now?

Shawn Weidmann: One piece of advice, actually this is appropriate since I have, I think I told you beforehand, i I have a daughter who’s in and business and a son who’s at Stanford now. I always tell them take more chances, take more chances, you know, significantly raise your risk profile because you got such a great background, um you know, yeah it’ll be great, like take those risks. um I think that’s the,

Shawn Weidmann: That’s the thing when I look back on it, I go, I’ve had so much fun doing this, doing some of the other, like people thought I was crazy when I went from being the COO of public storage, a $50 billion dollar company to go run, I don’t know, we were $90 million dollars in revenue at Stratford School when I did. Had so much fun doing that. i’ Building that to taking it from $90 million to, you know, almost a billion dollars, or $750 million dollars in revenue, and that was fun.

Shawn Weidmann: But that was a big risk. And there’s other things we we don’t need to talk about v or where I chose not to because I wanted to avoid risk that turned into these wildly successful things. um So I always encourage everybody to take more risks than you’re comfortable with.

Alejandro Cremades: That’s amazing because at the end, you know, to where there is risk, there’s growth. And like when you get like stuck, you know, in those corporate jobs and you get intellectually stuck to there’s like no growth, you get you become too comfortable.

Shawn Weidmann: Exactly.

Alejandro Cremades: So I love that approach. sean So for the people that are listening that would love to reach out and say hi, what is the best way for them to do so?

Shawn Weidmann: Either on you know you can find me on LinkedIn or drop me a note that at zephyrhome.com.

Alejandro Cremades: Amazing. Well, easy novel. Sean, thank you so much for being on the Deal Maker Show today. It has been an absolute honor to have you with us.

Shawn Weidmann: ah Thank you, Alejandro. It’s really really been a pleasure.

*****

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