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When we first met Ron Gura in Tel Aviv, we had just launched our business and were finding our footing as founders. We stepped into his office on Rothschild Avenue, where he'd recently been acquired by eBay, and from that moment on, Ron became our trusted voice of reason. Now, years later, we're thrilled to bring his insights to Unfinished Business.
Welcome back to the podcast. This week's episode delves into the early — and often overwhelming — stages of entrepreneurship. We frequently hear from young entrepreneurs asking the big questions: Where to begin? How to find the right co-founder? Whether to seek VC funding? And most crucially, how to land on the right idea. With his extensive experience founding multiple companies, including his latest venture, Empathy, Ron brings invaluable insights into the common pitfalls, misconceptions, and critical first steps for new founders.
Read on to explore how to recognize when you've found the right idea and how to stay committed — even when faced with conflicting advice. Let's dive in.
Alex: With your experience, having founded multiple companies, including Empathy, what are some common misconceptions around identifying the right idea, getting market validation, and finding early signals to follow or ignore?
Ron: Well, my first question is always, why do you want to start this business? A lot of times it’s, 'It’s a good time,' or, 'I was approached by someone.' I’m a bit more romantic on the entrepreneurship scale — I think you should feel like you’re placed on this planet to start this specific business. Why this business?
There used to be a genre of “purposeful” or “mission-driven” companies, which sounded like nonprofit branding. But today, every company should be mission-driven. Why else would people follow you, connect with your brand, or want to join you? For me, it’s always been about creating something bigger than myself — I’ve always leaned into the “cheesy” side when it comes to defining a company.
Alex: Yeah. So it starts even before the idea. You’re saying it’s a calling to be an entrepreneur and a founder — it starts as something that you have in you and that's where it starts.
Ron: I believe so. When we talk about a calling or purpose, it doesn’t have to mean saving people from cancer or reducing car accidents; it could be a DevOps company. It’s just something you’re genuinely excited about and have a unique perspective on, maybe because you’re an outsider. You might not be an expert, but you’re passionate about something and think, Why isn’t someone doing this?
Most often, it’s from a personal need or “itch.” It doesn’t have to be physical pain; it’s just something you’re driven to solve. And if you’re bluffing — whether to your co-founder, investors, or yourself — then you won’t last through the ups and downs of starting a company.
Alex: Right. And that’s what I've always felt too. Lee and I have had businesses across different industries, but there's something about just wanting to crack that nut and wanting to be successful that is really a key driver. Creating something that impacts people that makes their lives better. So there's like that deep passion for solving problems.
Lee: But I do think back on the Clay process. Alex and I entered an industry we were passionate about, but as outsiders in an arena where you really can’t be an outsider — it made things very challenging. With Ivy, we were outsiders too, but in that industry — workflow solutions for home remodeling professionals — being an outsider helped us see their workflow differently. In healthcare, though, being an outsider isn’t as helpful; there are so many blockers to learning. But I have a question, Ron. What did you learn during your time at Aleph that you’ve applied to both building Empathy and advising other early-stage entrepreneurs?
Ron: Joining Aleph after my time with the GIF project at eBay was really an educating experience. I spent a year just across the street with Michael and Ed, and Aleph was relatively early-stage. I got to see so many different founders on so many different topics a day, and spent a full exact year thinking about what I want to do next and decided to go eventually back into the arena. Empathy was definitely something I spent a lot of time thinking about back then. The biggest distilled insight I got was you can't take naivety for granted. It's such a blessing and you lose it every day. You wake up, you learn something new, you see something that didn't work, you test something. You polish your instincts and you lose it. Every day you lose a little bit of your beautiful childish naivety that you had when you started your first company or wrote your first email. When you lose it, when you know too much, when you ask too many questions. Sometimes I see serial entrepreneurs struggling with that. And I think you too can say, if you're thinking about a third business, like, it's never gonna work and it's too hard these days.
Alex: Hmm. 100%. You know too much. You see the pitfalls before you even start because you've already done it and you have all these assumptions that actually don't work in your favor the second time you do it.
Lee: And you have the battle wounds that are still not healing, right? Like our wounds are still oozing. Whereas when we started ArtCenters, we were so naive. Like we thought the world was our oyster.
Ron: And you've got something to lose. At some point, you have to say, I'm going to burn the boats and just do it because I can't research it for another five, six months. That's also what happened here with Empathy four years ago. We knew we want to show up for people in a very non-trivial space — and that's loss. It's frequent, but it's inevitable. And I want to show up for them. I want to save them time and money and stress. And I'm sure technology can do it. But that's pretty much all I knew.
Would it be B2C or distribution or B2B? Is it going to be on the emotional side? It's like a head space for grief, or is it going be like a toolbox for a state settlement and a state administration or both? Is it going to be a service or technology oriented? There's 50 others I'm not gonna test for now with my limited resources. And even if you have a lot of capital, you still have limited resources.
At some point you have to say, that's enough for now. Let's go. And if you don't, then you let context get in the way of pure naivety. If you lose naivety, I think you can't do this. Not just start a company, but actually anything. When you're going on a Zoom call for the 10th time with a Fortune 100 player. You have to believe today is the day. Today it's going to happen. Today the stars will align. That's naive.
Lee: But what's the difference between naivety and arrogance?
Ron: I think there's a huge difference between being arrogant and being naive. If you go back to my example, I have a big meeting an hour from now. This is a Fortune 100 life insurance carrier that we’ve been talking to since 2022. I'm confident they’re going to join our partner network by end of year. But If I'm arrogant, I'm going to come in and I’m not going to be able to bring my best version of myself because I'm certain I know everything. I'm not listening. I'm not learning anything new. I'm teaching them instead of learning what's holding us back. And if I'm naive, I'm just going to manifest the fact that this is going to happen and I want it to happen. I'm gonna be excited about the meeting and I'm just gonna ask questions to people who know everything.
Alex: So asking the right questions in a way that they're not so self-conscious about where you land in terms of how the person sees you, how maybe the meeting dynamic will change.
Ron: And I'm not saying naive or manifestation in a fluffy shanty way, I guess. I learned that from Michael at Aleph, from a very different aspect. And he learned it from one of his mentors at Benchmark. And I remember him doing this breath before he entered the room. And like, I was like, what was that? Michael said, in the VSC business, 99% is going to be a no. It's a very negative business. You've got to believe this meeting is the one. I'm going to meet someone who's going to build a hugely successful, impactful, purposeful business for humanity in the next 45 minutes. Otherwise, it's going to be very hard for me to sit there.
Alex: That makes sense. Lee and I are big on manifesting. But I think part of it is believing in yourself and believing that you're already successful at what you're doing. And that's what gets you through the ups and downs of entrepreneurship is really that sense of purpose.
Lee: I do reflect to the early days when Alex and I were embarking on our first idea after the acquisition and meeting with an investor we really, really loved. And he was like, girls, I want to be able to invest in your idea. I want to be able to invest in you. But why do you have to do in the parents space? It's such a difficult space.
It's the trap that a lot of second time entrepreneurs fall into. We left that meeting being like, he doesn't know anything. Let's not listen to him. How dare he? But I wish we had listened to him. We were so blinded by the industry and the personal pain point we were feeling that we weren't receptive to wise words because we were a little bit arrogant that we could do it too. What are your thoughts on that? When does an early stage founder understand when to take that criticism on the idea they're going forward with?
Ron: It's really tough to draw the line. There's people telling you advice about go to market like, don't go there. Trust me, this is a really bad path for you guys. And there are others telling you that you should change your idea completely. My approach to ideation is, I can't shift my parenting idea because I came to solve problems for parents. I get that a lot of people that are a little bit resourceful, a little bit experienced think they have the solution for all other parents. But I actually believe my solution is going to be better for parents and I can't shift to another market because I want to solve a problem for parents.
Now, if you're telling me I shouldn't do it B2C or B2B and I shouldn't do it US or UK, I'm listening. If you're telling me I shouldn't solve the problem I was put on this planet to solve, I'm going to nod and leave, smile, and then do what founders need to do also every day.
You also have to be in denial all the time. It's going to work out. We were at this point last year in Q3, it was tricky, but we made it happen. We're going to do it again. Denial is also really important not because things are going to work out by themselves, but because you can only think about 5 to 10 problems at a time. Someone is showing you a problem that's definitely real and definitely tangible, but it's not on my top 10 problems today.
Alex: I would love to dig a little bit more on the product market fit side of things, since we're talking about good enough mentality. A lot of times founders will think they have traction. How do you distinguish between that early traction that is real and that true product market fit?
Ron: I think these two topics connect really well, and here again, I think you need to understand the fundamentals of your specific venture. One of our operating values is almost the opposite of good enough — and that is obsessing about the details.
If I’m preparing something for an HR manager, thinking about buying Empathy as the benefit to their employees or a head of claims at a life insurance company, thinking about connecting it to their user experience. Good enough? Let's go. But if you’re touching the delicate relationship of trying to get people back on their feet again, you don't get to make mistakes. So it's really about understanding your business.
Then saying not enough on these topics, good enough on other topics — because velocity has correlation with impact and fundraising and resources, which eventually is needed in order for us to create that impact. If we do things too slowly, we're never going to help anyone.
Alex: That's right. So what you're saying is there are things that are worth obsessing over, interactions with your customers, things that you define as principles for your company. And there are things that just good enough is good enough, and you just shoot for the sake of velocity and moving fast.
Ron: Exactly. People sometimes obsess about workspace or, you know, color palette. Sometimes they should. Sometimes they shouldn't. Really about what type of a business you're building. So your other topic is equally interesting, how do you take that good enough and decide that there is product market fit and I can double down and invest here again? The reason people say you feel it when it happens is not because it's the equivalent of love and you just know.
For instance, some people will say once you get to X amount of millions of dollars in recurring revenue, it's a product market fit. I disagree with that. That could be a really small number, a really big number. One of the challenges we had is that our average X size from a client is like a million dollars. So you close three clients and you're like, okay, this is working. But you've got a really small sample of three people. So what is enough? 10, 20.
But if you're selling something for $10,000 and you've got 200 customers, that’s a different story. So I don't think there's a line. You need to understand your business.
Alex: And it’s the difference between that vanity metric versus real traction.
Ron: Exactly. For example, I actually looked at a product-market fit only when we had renewals.
Alex: That makes sense. That's retention.
Ron: People paid a large amount of money for X amount of months. And then they say, you know what? I want it for five years. I want it for six years more. So I'll say, okay, this is now officially worth it.
Lee: So when you know you have the idea and then when you know you have that product market fit, that goes into execution, right? An idea is only as good as the execution. And oftentimes that comes down to that early founding team. Where are the mistakes you see a lot of early stage founders making with those first hires?
Ron: I think when you're adding people to a team, small or big, you're always balancing between potential and performance. And when you're big enough, you kind of want both. But you can't always get both. It's mostly, I would say almost always focusing on people who have really high unlimited potential that usually overlaps with affordability. You can't raise a million dollars seed and get the CMO of Amex and the CTO of OpenAI to join you guys.
Lee: But would you even want them at the early stage? I think back to Ivy, our best employees were the ones with the least amount of experience, but the most can-do attitude. The CMO at Amex would be amazing, but they're so far removed from being all in hands on.
But sometimes if you're building a very specific company, sometimes you actually want that person with the experience. You don't need them to manage a thousand people, but they might have insights that would accelerate your business.
One thing I learned after joining eBay a decade plus ago, is startups usually like to kind of mock at enterprise companies and corporate America. I really advise entrepreneurs not to embrace corporate America, but to understand enterprise dynamics, especially if you're in the B2B business. Yes, some of them are antiquated. But what you really want to understand is you need to add policies and add clarity, but you don't want to write policies that you don't need yet because that's corporate.
Ron: Right. In a startup, it's a waste of time and energy and attention. Long story short, learn from corporate America and decide when. I think too often people are looking for binary rules. This is product market fit, never do this. Always listen to that. Don't take his advice, take his advice. You need to develop a theory of why your version is going to work and what the other guys are missing.
Alex: Yeah, and part of it is acknowledging you don't have all the answers, right? You're not going to know what that policy is until maybe something happens or someone comes out with an issue that you have to deal with. And so much of that is entrepreneurship. And you're not going to know what your revenue is going to be next year. You have to make assumptions. You have to show a certain brain around unit economics and CAC and LTV. But these are all assumptions. And you have to be comfortable to be in that space of acceptance around acknowledging that you're not going to have all the answers.
Ron: Couldn't agree more. getting comfortable being uncomfortable is one of the most important virtues for founders. Like you literally swim every day in a lake you don't know anything about and you don't know if it's even a lake or an ocean or if there are sharks in it. You just have to get comfortable doing that.
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