Why Most Successful Founders Aren’t Dropouts: Orlie Benjamin’s Path from Law to Lasoh

In this episode of Project Gamma, Warner Moore speaks with Orlie Benjamin, Founder and CEO of Lasoh, about building companies after a full career, not before it. Orlie shares how her path from law to business shaped a deeply customer-centric approach to entrepreneurship, why experience is often a founder’s biggest advantage, and what it took to move Lasoh from MVP to version 1.0 while empowering others to become entrepreneurs.

Transcript

00:00 – Welcome to Project Gamma

Warner Moore: Hey folks, welcome to Project Gamma. At Project Gamma, we have smart conversations with smart people across entrepreneurship, technology, and cybersecurity. My name is Warner Moore. I’m a technologist and security leader who has helped build multiple business-to-business software-as-a-service companies across industries, and I’m passionate about modern cybersecurity practices. I’m also the founder of Gamma Force, where we help tech companies with cybersecurity strategy by acting as their fractional security organization.

Orlie Benjamin has an educational background in law, which she pivoted into business. Her career has been multifaceted, spanning business strategy, customer experience, and marketing. After a meaningful corporate career, Orlie decided to table-flip and founded Lasoh, and she’s now working to create more entrepreneurs. Welcome, Orlie — thanks for being here.

Orlie Benjamin: Warner, thank you for having me.

01:08 – From Law School to Business

Warner Moore: Let’s start with your origin story. You started on a pretty impressive path, becoming a lawyer — you’re a JD — and then decided to do things differently by moving into business. Share more about that. How did you choose the path you’re on?

Orlie Benjamin: I’d say I started on the path my parents told me to go down. As the child of two immigrants who value education, the answer was always “be a doctor or a lawyer.” My brother is a doctor, and so is my dad. I don’t like blood, so I figured maybe the lawyer thing would work out. I got into law school, went through the whole program, and passed the bar.

But while I was in school, I started noticing I had a real interest in the business law classes specifically. That’s when I explored adding an MBA to the law degree — they let you do it in one additional year, essentially for free. It felt like a no-risk way to buy myself time and figure out a next strategy for something I was finding pretty boring while I was doing it.

02:15 – A Nonlinear Career Path

Warner Moore: One thing we often glamorize is the young dropout founder. What’s understated in entrepreneurship is that the people who are more commonly successful have actually had a career first — they’ve built experience, learned an industry. You’ve had some big jobs in your career. How did that translate into the company you founded?

Orlie Benjamin: My career has been super nonlinear, a bit jagged. I’ve worked across a variety of industries and functional areas — pricing strategy at American Airlines, digital marketing at Victoria’s Secret, strategy and product design at NetJets. None of those functional areas were the same, and none of those industries were the same. From there I moved to a CPG company and eventually became head of marketing at a California-based startup.

Throughout all of these disparate experiences, I saw a common thread: my interest in people. I think really great businesses work backwards from customer pain and solve for people. Whether it’s pricing strategy — which is really about changing behavior through price — or marketing, which is about influencing behavior to drive revenue, or customer experience strategy, which is about understanding friction and solving it, all of it ultimately comes back to the people who engage with the business and the value delivered to them.

At the CPG company, I worked in the innovation group and had the opportunity to build something from zero to one for the first time — my first real exposure to entrepreneurship inside a corporate setting. I got way too into it. I’d always been part of a much bigger ship, helping steer it, but there were a lot of people on that ship, and it was big. Having complete ownership over building something unlocked a part of me I didn’t know existed.

After that, I moved into the corporate venture capital group, and I got really jealous of the founders we were funding. I realized I was sitting on the wrong side of the table. That’s when I decided to leave corporate America and go learn about entrepreneurship. I was in my mid-to-late 30s at that point, and I’d never even been exposed to it until a corporate environment put me in touch with it — my whole life, I had risk-averse parents focused on doctors and lawyers, and betting on yourself like that seemed entirely radical. It was completely off my radar. But I eventually found my way into it, and I feel like I’m really on my path now.

04:55 – A Family Skeptical of the Leap

Warner Moore: I didn’t know that about your background — the corporate entrepreneurship angle. I’m curious, and this isn’t unusual among founder friends of mine — did your parents give you a hard time because they couldn’t relate to the entrepreneurial path you took?

Orlie Benjamin: Absolutely. They thought I was crazy, and honestly, they still worry about me. The first business I built outside of that corporate setting was buying land near a state park here in Ohio. I bought a lot of it, because I’d started noticing that the drive-to-destination vacation rental industry was booming. It clicked for me when my favorite vacation rental sold out for an entire year in 30 minutes. I thought, “Okay, there’s real demand here.”

My parents thought I was nuts. I refinanced my house, bought 78 acres, and built a custom vacation rental business. In the first year, we netted six figures — I couldn’t believe how well it did. That’s actually how I discovered this industry I now work in: vacation rental management as a professional field. I didn’t even know it existed. It all started with identifying demand from something selling out fast, having genuine interest in it as a customer myself, and wanting to build something. My parents were terrified the entire time — they told me I shouldn’t do it, that I was being too risky.

Warner Moore: Yeah, it’s definitely not the easy path, but for some folks it’s the right one. One thing I like about your approach — and you mentioned this — is being customer-centric, and how part of founding Lasoh came from stumbling into a problem through that first rental property business. Talk more about being customer-centric, identifying the problem, and how you found it in the market.

07:03 – Being Customer-Centric From Both Sides

Orlie Benjamin: Throughout my career in commercial functions, you’re always trained to think customer-first — it’s practically a slogan baked into your KPIs every year. It’s how you’re trained to think, and it became something I naturally brought into any scenario. On top of that, I layered my own personal experience as a customer — someone who rents vacation properties all the time. I love to travel; a lot of the places I worked, like American Airlines and NetJets, were all about travel. But then I got to flip the script and understand what it’s like to actually operate a place people travel to.

By understanding both the guest and host sides of that relationship, I could see pain points I could imagine solutions for — partly because of my work experience, and partly because I’d seen how more established, later-stage industries had already built playbooks around things like experience strategy or nurture marketing and relationship management. This industry, being younger, hadn’t unlocked those things yet. Identifying the pain, imagining a solution, and feeling it personally from multiple angles — that’s all part of the problem identification process.

08:30 – Disintermediation and Empowering Entrepreneurs

Warner Moore: One thing that’s really cool about what you’re building with Lasoh — I travel a lot, and it’s not unusual for me to rent from individuals, whether that’s cars or properties. It drives me nuts that on some platforms I can’t communicate with the person until I’ve already booked, and I need to know details beforehand — like which tires I need for the weather. They intentionally make it difficult to do the thing I need to do, because they’re trying to control the customer relationship. With Lasoh, you’re disintermediating that — empowering people to become entrepreneurs. Talk more about your mission and your thinking around disintermediation.

Orlie Benjamin: What Lasoh does is enable professional operators of vacation rental businesses to build a direct relationship with the guests who come in through booking platforms, turning those distribution channels into lead generation for future direct customers.

Every marketplace is in the business of matchmaking — Amazon, Etsy, Airbnb, all of them. They’re two-sided marketplaces that make money from both sides of the transaction. What I don’t love about that model, as someone trained to think direct-to-consumer, is that if you don’t know your customers, how do you even know if your business is doing the right thing? That goes back to customer-first thinking. One of my strongest early reactions while building my own vacation rental business was frustration at not having a direct relationship with my guests — no visibility into what was working, what wasn’t, what they liked. Continuous improvement comes from continuous feedback.

So one of the things I set out to solve was the ability to essentially remove Airbnb from the equation once a guest arrives, and turn that guest into someone loyal to the vacation rental brand — not loyal to Airbnb. A lot of people use “Airbnb” as a noun, an adjective, a verb: “I stayed at an Airbnb,” “we went to an Airbnb.” Airbnb has done such a good job of becoming the whole experience that the operators behind the scenes — the people who actually own or operate the property — become invisible.

I think a truly good business is sticky and built on repeat customers, because repeat customers are essentially an annuity — a recurring revenue stream, and every business wants recurring revenue. So removing Airbnb from the equation by building and nurturing a direct customer relationship, driving repeat bookings, and maximizing revenue across the full stay experience — that’s exactly what Lasoh does. It’s a tried-and-true direct-to-consumer playbook: how many customers do you have, how much do they spend per transaction, and how many transactions are there? But if a platform doesn’t let you capture repeat business, or communicate with guests to increase their spend through upsells or extended stays, all you have are one-off transactions — and there’s nothing recurring about a transaction that comes in cold off a distribution channel.

Beyond the business model, I’ve also found so much personal joy in the process of being an entrepreneur. Most of the people managing these vacation rental businesses are small to medium-sized operators who’ve essentially been disintermediated by a large platform — they don’t have control over their own book of business. I feel like I’m enabling entrepreneurship for them by giving them a more sustainable business model, better marketing, and tools that are typically much more sophisticated — closer to enterprise-level — but brought down to the SMB space, so they can take action on things they may not otherwise have the training to do.

13:06 – The Loyalty Gap in Vacation Rentals

Warner Moore: I like that a lot — empowering folks. I travel a fair amount and frequently go back to the same places. I like going to Salt Lake, and I’ve tried to build relationships with the people renting properties there, since I don’t want to own property myself. But honestly, nothing has stuck consistently. I find it a bit ridiculous, because if I were in that position, I’d be thinking, “Yes, please keep coming back — make it easy, just show up every year.” I think a lot of these platforms let operators avoid ever thinking about the customer relationship at all, just assuming distribution will always be there, at least in a hot enough market. It’s really neat how you’re empowering people to actually be entrepreneurs, which isn’t always the case when it comes to running a rental property.

Orlie Benjamin: It’s definitely something that keeps me motivated, because I’m building a business that aligns with my personal values and the things I’m passionate about. Blending all of that together makes the work genuinely fun — it doesn’t feel like work. I feel like I’m doing something I love, which makes it a lot easier to work hard for long hours every day. If I were doing something I didn’t like — say, if I were a municipal attorney right now — I’d probably be pretty grumpy, feeling like every hour was onerous, unless I’d found some niche within law that I loved. But you tend to specialize pretty early in that field, and it’s hard to get out of it once you do. So for me, this was the right path.

Warner Moore: Vision, impact, values — those are things I think about frequently. We were talking earlier, and you mentioned that you’ve recently taken Lasoh from MVP to 1.0. What was that journey like? How did you get there?

15:02 – From MVP to 1.0: Team, Customers, and Capital

Orlie Benjamin: Everything is a team effort. I obviously have a vision for the business based on my experience in prior corporate environments, and I can see how those playbooks translate into this underserved industry. But getting to 1.0 is absolutely a triangulation of a lot of moving parts.

First, having a really good team that can take an idea, break it down into something implementable, sort out priorities — what’s MVP, what comes later — and then actually build it. I’m a non-technical founder, so my engineering team isn’t just a delivery team; they’re a strategic partner in figuring out how we make things happen. Delivery comes last. The building and shaping process — translating an idea into something buildable — is the most important part.

Second, it’s not just about the ability to build, but building the right thing, which is where leaning on customers becomes essential. We started the business with me as the first customer, but there’s a real risk of “me-marketing” — imagining only my own problem instead of the industry’s problem, and building a big solution to the wrong one. What was critical was actually working with other people and early users — we call them design partners, because they helped us design the product. It wasn’t a typical customer relationship where the expectation is simply being serviced; it was a real partnership. They’d identify pain points, and we’d commit to solving them, while also validating whether it was actually a broader industry problem through research and customer discovery. Taking something that started out kind of ugly and embarrassing as an MVP and steadily building it toward something with real customer demand was the second key piece.

And finally, having some money to do all of that. I was fortunate to get grants, and I bootstrapped paying high-quality people and bringing in help, because having a bit of capital is what takes an idea to a place where it’s actually actionable. So — team, customer-validated building, and capital. Those three things.

17:49 – Solving Your Own Problem vs. the Market’s Problem

Warner Moore: That’s such a knowledge bomb. For a lot of technical founders — engineers, technologists — it’s easy to think, “Oh, I can just build this,” especially if they’re solving a problem they personally have. What you’re describing is different: you solved a problem you had, which isn’t necessarily bad, but you didn’t assume your problem was the market’s problem. You went and validated that you were solving something the broader market needed, and built a business around that. Some founders are lucky enough to learn that lesson early; for a lot of people, it takes years. I’m curious — do you have co-founders?

Orlie Benjamin: Yes — me.

Warner Moore: I often talk with non-technical founders who are trying to navigate building a product when they’re not technical themselves. How did you navigate that? It sounds like you figured it out pretty well.

18:47 – Building the Right Team, Slowly

Orlie Benjamin: Slow and sloppy at the beginning, honestly. I had a co-founder for three weeks early on — a clear mismatch in skill set and life experience, and we unwound that quickly. Then I hired someone who looked really legitimate on paper, but their actions and words didn’t line up consistently, and I’d already spent about $50,000 of my own money by that point. A lot of people probably would have quit there, especially since I wasn’t yet working on this full-time — I was consulting on the side while moving toward going all-in.

The third time was the charm. I leaned on my network and found who is now one of the engineers at the company, and we started working really closely together — building in collaboration with customers, doing some reverse engineering around the marketplace, figuring out where we wanted to play and where we didn’t. My ability to bring industry knowledge and customer-centricity, combined with his building capability, was a really important combination.

I also found a great product designer early on, so it was a product designer, a full-stack engineer, and someone helping with project management. As we started getting more customer traction, I was able to dig up additional grant funding — doing the kind of administrative legwork ex-lawyers are good at, applying for things — and that let us move faster. Eventually that engineer brought on a partner, so we had two engineers, then three, and now I also have a fractional product leader.

It’s been organic, slow, and bumpy in terms of finding the right talent. That’s why I emphasized starting with the right team — ideas are cheap, and everyone has them, but if you can’t bring an idea to life and execute on it, it doesn’t matter. There’s a lot I can’t do myself. I have plenty of skills, but also plenty of gaps, and being really aware of where I need to build capability around those gaps — so we have a full-stack team as a business — is one of the most fundamental parts of my job.

21:16 – Culture: Transparency, Trust, and Conflict

Warner Moore: A strong team really is a luxury. Back when I was building a health tech company, something we said constantly was that people were our competitive advantage — and they were. I still think about it that way today. Companies that want to hire the best and take care of their people well — that’s not just how you build a good company, it’s how you build a sustainable one. Being less transactional in your own business seems to mirror how you’re helping operators be less transactional with their guests.

Orlie Benjamin: One part of the culture I really care about at Lasoh is that I’ve essentially flipped the script on everything I didn’t like about corporate life. I’m absurdly transparent — financials are shared, so if people feel like the business is risky, there are no surprises. Everyone knows how much runway we have, everyone’s aware of what ride we’re on, because I think people deserve to know and to make informed choices. There’s no bait and switch.

I’m also someone who gives trust first. If that trust gets whittled away, it’s through actions, not words — you have to pay attention to what people do, not just what they say. If trust is broken, I move quickly, because the red flags are already there, and I’m willing to end relationships quickly if they’re not working. This isn’t corporate America — we don’t have the luxury of PIPs and 90-day plans. Our runway is everyone else’s livelihood, so decisions have to be what’s best for the group. It’s fairly utilitarian in that way.

The one thing I do push people on is pushing back on me. If people aren’t opinionated enough, or aren’t challenging me enough, that’s the thing I care most about, because when you’re in a leadership role, you inevitably carry more weight in the room, whether you intend to or not, and people may not feel as comfortable disagreeing. I love debate — I went to law school, so I don’t see conflict as an issue at all. I love conflict. Diamonds are made under pressure. Push back, give me your point of view, tell me things I don’t know. The only thing I really give people a hard time about is being too quiet, or not pushing hard enough on how we approach problem-solving. Culturally, that’s really important to me.

24:04 – On Giving Candid Feedback

Warner Moore: We’re all always learning, in every role and every stage of life, and if we’re not getting feedback loops, that’s a real challenge. Throughout my career, I’ve often been the person who gives candid feedback to people who aren’t used to receiving it, and that hasn’t always worked out well for me.

Orlie Benjamin: What you say and how you say it can be two very different things.

Warner Moore: That’s true. People often say they want honest feedback, but they don’t always actually want it. I gave it anyway, because it’s a gift, whether or not it’s received that way. It’s also helped me figure out where best to spend my own time.

25:00 – Closing Thoughts and Book Recommendations

Warner Moore: I want to thank you for your time today — fantastic conversation, plenty of insight I’m sure folks will value. Any closing thoughts, book recommendations, anything else you’d like to share with our audience?

Orlie Benjamin: The one thing I’m really focused on right now is time — it’s my scarcest resource. I’m thinking a lot about how our team builds the right capabilities across everyone, and how I can remove myself from things someone else could handle, so I can focus only on what I’m uniquely positioned to do. I’m realizing that a lot of my job is about facilitating momentum, inspiring people, and creating safety for others so we can function as a team — the tribal aspect of a business is genuinely important.

I’ve shifted a lot of what I’m learning lately. Early on, I had to learn how to be at least okay at product strategy — I listened to a lot of Lenny’s Podcast, so thank you, Lenny, for all of that. But I’ve moved away from a lot of that now, since I have someone who owns that. These days I’m focused much more on human behavior and how to build the best possible team. I’ve got a couple of books on my nightstand around that. Honestly, I’d love to ask the group — what is everyone else reading right now? What are the best practices people are seeing work? That’s what I’m trying to learn.

One book I read recently — it’s kind of a classic, so it feels almost ridiculous to bring up — is a quintessential management book, “High Output Management” by Andy Grove.

Warner Moore: Yeah, I have that one.

Orlie Benjamin: Really, really good.

Warner Moore: I’m in the middle of it now. He was the CEO of Intel, right?

Orlie Benjamin: Yep — founder too. It instantly became one of my top management books. It’s a little less “squishy” than organizational psychology, but it’s fascinating. I went back and discovered that he’s actually the one credited with creating 360-degree reviews.

Warner Moore: That came from that book? I’m actually a huge fan of 360 reviews.

Orlie Benjamin: I didn’t believe it either — I knew the concept from the ’90s, but I didn’t realize he invented it. Really good book. Adam Grant is another one of my favorite authors — an organizational psychologist with really strong content on this subject too.

Warner Moore: If people have book recommendations for you, Orlie, how should they reach out?

Orlie Benjamin: I’m sure there will be some comments here I can follow up on. My email is my first name at Lasoh.io, and my full name is my LinkedIn profile. If anyone finds what we talked about interesting and wants to engage, reach out via LinkedIn or email — I’d love to hear what other people are thinking.

Warner Moore: That’s generous of you, Orlie. Thanks again for being here, and thank you all for listening to Project Gamma, presented by GammaForce.io. If you enjoyed this podcast, check us out on your favorite podcast platform to catch future episodes.