Greg Moran (00:01.948) Welcome back Founders Journey podcast. Um, if you've ever had one of those moments in your life where you make a decision and then you think, why in the hell did I just make that decision? When the moment comes around, this is exactly that moment for me. Um, so welcoming, uh, well, welcome back, Peter. Good to see it. And, uh, Peter Dean (00:27.271) I try not to laugh too much. Greg Moran (00:30.408) Actually, the reason I'm saying that is because I think I've just made myself vulnerable to the two guys I'm probably closest with in the world outside of my family here. So welcoming Ira Grossman to the podcast today. And Ira is my business partner at Evergreen Mountain Equity Partners. Ira and I have been business partners for on and off, probably almost coming up on, well, way too long, probably coming up on 25 years at this point. Ira Grossman (00:42.689) Thank you. Greg Moran (01:03.268) So, it's been a long time. He's also probably one of the top experts out there in terms of product roadmap, building product inside software companies. So we're going to be talking about that today, but undoubtedly this is going to devolve into mayhem. So just warning in advance because Peter and Ira are probably the two guys who know every sordid story, dumb thing I've ever done in my entire life. So anyway, welcome Ira to the podcast. Ira Grossman (01:17.645) Thank you. Ira Grossman (01:31.662) Thanks. Thanks for having me, gents. Peter Dean (01:33.521) I'll add one thing about Ira. So when you work with any of their portfolio companies, and sorry to really reveal this, if you want like fiscal responsibility and someone's gonna be like, we can or cannot do that, I call Ira, that's who I call, because he's like, yeah, we could get this done. Greg's like, yeah, do it all, let's go. He's like me. And then Ira's like, yeah, we can't do that. That's not gonna happen. Greg Moran (01:55.902) Ha! Greg Moran (02:01.323) Ira is definitely the more responsible of the two of us. Peter Dean (02:02.865) He's like the yin and yang of it's like a perfect combination. Exactly. Ira Grossman (02:06.71) Try to be the adult in the room. No, thanks guys. This is incredibly incestuous and fun to be on. I will say seriously though, congrats to you guys. I know creating a podcast, there's so many out there. It's so hard to break through the noise and provide some good value and trying to be reasonably objective here. I think you guys have done a really good job over the last year of really. Greg Moran (02:08.881) That's right! Peter Dean (02:16.067) Hahaha Ira Grossman (02:33.85) taking this to the next level, you probably like going the whole other direction now bringing me on, it's gonna devolve from a level of professionalism you've had previously, but seriously congrats. It's really cool that you guys are doing this and put the time and energy into putting this content out there for founders. Greg Moran (02:52.808) Yeah, no, appreciate it. Peter Dean (02:53.133) Yeah, but just didn't know. I know Greg did the intro, but like Greg, why don't you give the intro or Ira? You can tell us about your background a little bit because highly qualified to be here to be honest with you so. Ira Grossman (03:10.082) Yeah, I mean, the short version is serial entrepreneur built three tech platforms in my career. Each of them were sort of five to 10 plus year runs. The common thread where they were all SAS. One was in the software modeling business. One was in the pre-employment assessment space where Greg and I spent a long time working together. And one was in the in the life sciences space, which was kind of a left turn from a. from a vertical perspective, but again, it was a SaaS solution and a great opportunity to learn. I've been a bit of an accidental entrepreneur. All three of those, for all three businesses, they were about six months. So had a founder, they were about six months in, they were living in the sort of proverbial garage mode when I got involved through, you know, various paths. Um, so, and you know, my passion is really understanding how businesses operate and how do they scale. Um, and I've always had partners like Greg, who are a little bit more of the visionary rainmakers. Um, and this has been a great combination for me. I've been really lucky to, uh, to have that journey. And then in, for context of today, you know, a lot of what I've learned about myself over the years is of all the different mechanics of a business. and how they operate. I like a bunch of the pieces of it. The one I really have passion and enjoy is the product component. And how do you bring a piece of software to life, which is a challenging journey as everybody who's ever tried it knows. Greg Moran (04:47.292) Yeah, and I'm sorry, Peter. No, good. Peter Dean (04:47.737) Yes. Good. I was just going to say, so the product roadmap and creation, I know I've used you as a resource for my own businesses that I've been a part of, why don't you talk about your experience on product roadmap creation and you know, how that, how you got into that and why that's important to you. Ira Grossman (05:10.562) Yeah, I mean, the roadmap is sort of the manifestation of the product strategy and the product strategy. What I've gleaned after years of getting punched in the face and trying to figure out how to build a software business to scale is that the alignment of the product team, the client team, sales team, the engineering team, I mean, really all the folks who are executing within the business. The alignment of those folks, especially in a software company, just ties back again and again to what are we building? How fast can we build it? What can we deliver? What do the clients care about? Where are the pain points? How do we solve those pain points, et cetera? So to me, that's just a it's a really cool challenge. What I love about software is that you create something from nothing. A software startup, most of the time you try to build a new, a better mousetrap or you're trying to really disturb or disrupt a new market, but you're creating essentially something from nothing with software, which is really cool and really daunting. So having a clear product strategy to wrap around that, we can get into sort of all the vectors that come off of that, but it really impacts everyone in the business. And without it, I think you'll lose credibility really quickly if you... can't articulate, again, in a software SaaS business, if you can't articulate where your product is, where it's going, where it's headed, why, where the risks are, et cetera, et cetera. If you can't articulate that, you're just going to have a lot of challenges. So that's why. And for me, again, it was sort of like an accidental entrepreneur, a bit of an accidental product leader, just being miserly and cautious in software startup mode. There was no thought of we're gonna hire a product leader. No, somebody on the leadership team or several of us on the leadership team are just gonna figure this out. We love what we're doing. We're passionate about the product. Let's just figure out what we have to do next. And I just gravitated towards that and ended up taking on that role in multiple companies over the years. And quite frankly, in the early days, Ira Grossman (07:30.402) Some of the concepts that exist today didn't even exist. There's no such concept as a product owner. It just didn't exist. Even a product manager was a vague idea in the first business I started. Now it's predominant and there's a whole framework upon which people can work. And I'm a big advocate for that. But this is just, we need to survive. Let's figure out what our product strategy is. So it was very organic for me. to end up there is the answer. Greg Moran (08:01.588) So starting at the high level, so you and I, over the summer, we did a, the reason this whole podcast came about is over the summer, we did a summer camp for our portfolio CEOs and leaders up here in Evergreen, Colorado. And Ira gave a presentation that we sort of jokingly referred to as making a product roadmap sexy again, which will definitely be titling this podcast, by the way. But Peter Dean (08:30.385) Hehehe Greg Moran (08:31.484) But kind of taking it from really high level, why does this whole concept, if you're a high growth, early stage founder, starting to hit scale, why does this matter? Why does this whole concept of getting really serious about your product matter? Ira Grossman (08:51.566) Yeah, I mean, it depends. Obviously, it depends on where you are in the journey, but it always matters. The degree to which pressure will be applied to you in the context of product is going to change and likely increase over time. But it matters again because it is the manifestation of what you're creating in a software business. So. You have to be able to answer the questions. And the questions are gonna come fast and furious. Even before you have a board, even before you have investors who might be hitting you hard with questions, your team is gonna wanna know, what are we building and why? And not just the software engineering team, sales team. If that's you and one other person, they wanna know what can we sell? Marketing organization wants to know, what are we building? So I can promote that. The client team, if you have it, again, it could be one person early on. but what is the product I need to become an expert in? So everybody in the organization needs to understand where we are and where we're going. It is the defining map of where the business is moving outside of the financial models, which are always a defining map and you can't get away from it. It's even less sexy than the product piece, but the product piece is the defining map of where the business is headed. And as a founder, whether you're, you know, many... Peter Dean (10:05.587) Mm-hmm. Ira Grossman (10:18.998) Software CEOs are technical founders, so they're deep in the weeds of this and they're passionate about it, even though they may not be the best person to create the product roadmap because they might get too technical. But even if you're not a technical founder, you need to really have good clarity. And again, it's not a precise science. It's going to have a lot of variability over time, but taking a quarter at a quarter... Peter Dean (10:42.917) Hmm. Ira Grossman (10:46.402) approach to this and understanding where you're headed, what you're building and why. And then, you know, the different components of a roadmap. So what is new build? What's enhancement build? What, how much time and effort do we spend on fixing bugs? How much energy do we spend just on focused on what our initial clients are saying versus what our vision is saying. So all of those are reasons why if you don't have context in a framework like a roadmap to work from, it gets really messy really quickly. Greg Moran (11:19.708) Yep. Peter Dean (11:20.873) So, so what does what's a great product roadmap contain usually? Ira Grossman (11:27.058) Um, so this, there's a lot, um, and, uh, you know, I'm a, I'm a visual learner. I really think making these things visual is really important. Um, there's a, there's a, uh, leader, a thought leader out there. It's been out, he's been out there forever named Edward Tufte. He was sort of my hero in the, in the visualization of data and design. Um, and Tufte was all about how do you create. individual visualizations. I know it's an old reference, but we all have great hair on this podcast today. Greg Moran (11:59.857) I was just going to make fun of you for having a hero in data visualization and design. Ira Grossman (12:06.767) I do, it's super geeky. I actually, his books are on the shelf behind me. But he really was able to show how elegant visualizations can take mountains of data and really expose them in an efficient way. And he's got really interesting examples, the Napoleonic Wars and where that was gonna fall apart if you looked at the visualizations. Greg Moran (12:07.314) Thank you. Ira Grossman (12:33.622) and the changes in temperature, though you could see where he was going to get into trouble and his army is going to get into trouble. The space shuttle Challenger and the fact that the O-rings were the cause for that terrible disaster, his visualizations were able to show that in a way that nobody had ever found before. So that's the sort of theoretical concept here. So tying that into a roadmap, which compared to those examples, now seems much less complex. There's still a lot of information. The ideal ingredients, I would say minimally, you want to have unique time. So time-based, I like quarters. So four quarters, four rolling quarters. What is the probability of delivery within each of those quarters? The current quarter we're in, I'm hoping to see high probability. By the time we get three, four quarters out, everybody should understand that things are going to change in the software business. So those are probably 25, 30. percent probability when they're four quarters out. So probability of delivering successfully. What are the elements that are on the roadmap? Again, what are we building that's new, enhancement, sustained, bug fix, integration? There's many categories. And then there's a lot that we can talk about in terms of how much should you have in each of those buckets, but understanding what those categories are. And then some relative size and color. So that all stakeholders can get a sense that yeah, we're only working on two modules this quarter But they're both relatively high complexity and they eat up a lot of resources. So those are those are some of the building blocks Peter Dean (14:15.581) So just to follow up on that, so you kind of alluded to this, when people build these, I'm sure you've been through this before and I've kind of seen you do this, they have all these things and they may have like five modules in there that are really complex. Like we want to do all of this. Like how often do you see that and how do you monitor that? Ira Grossman (14:33.775) Yep. So it's interesting. I always say the mantra for being in the product business is like real estate is location, location. Product is prioritization, prioritization. And priorities change daily and that's okay. You need to have a strong, flexible DNA to be in the product business because things will change and stakeholders will have varying opinions. Peter Dean (14:50.074) Mm-hmm. Ira Grossman (15:06.026) Um, but you're going to have to have the discipline to really have those good, healthy debates with all stakeholders at the table, um, to prioritize what's most important to the business. Cause it's never, it's never one thing in some ways it's really easier in the early, early stages is like, we just need to get a minimal product out there. I like minimal lovable product versus minimal viable, but some minimal product that we need to get out the door. It's just, in a lot of ways, that's the easy time, right? Because we just know we need these three features. We've got to get these three features to market. Everything else is noise. But very quickly, it's a very nonlinear curve. Very quickly, there's a lot of competing priorities at the table. So you've got to just be really transparent about that. You can get more sophisticated with it over time as well. You could actually start to quantify what's most important to the business. Peter Dean (16:03.283) Mm-hmm. Ira Grossman (16:03.646) and start to put some quantification around your prioritization. So it's actually, it's got some scales and some measurement around it, but start with just getting the right people at the table and debating it in advance versus debating it after you've started down the roadmap path. Peter Dean (16:18.886) Yeah. Greg Moran (16:19.956) How do you, I've heard you talk about this a bunch of times, right? And it's always interesting to me and I think, you know, I haven't gone through this a bunch of times as well. How do you tell a founder? how to prioritize, right? Like how do you make those decisions around prioritization in a way that will have a positive impact on this? Because I think it's really easy, and I know I've lived this, right? It's really easy to get really confused on, like that prioritization can change on a daily basis. And there's this like balance that you've got to reach, right? Like how do you tell a founder to prioritize or a product leader? prioritized. Ira Grossman (17:08.078) Yeah, I mean, it is hard. You're right. What I like to do is just start with getting the stakeholders in the room. Again, it might be three people early on. It might be 12 people later on. But who's responsible for sales, for client, for engineering, for marketing, et cetera? Get those folks in the room and sort of ignore the roadmap for a moment and just talk about, we know what the values of the business are. Hopefully there's a semblance of what our values and what our mission is. If there isn't, that's probably the exercise you need to do first, but let's assume that exists. Have a really frank conversation about, okay, when you guys think about our earned gals, when you think about our product, what's most important to you? And people are gonna raise their hand and say, The most important thing is creating raving fans. The most important thing is that it's engineering, it's got engineering excellence. Most important thing is that it's high quality. So get that all out there because everybody needs to have that voice. And the reality is they're all the right answers. Then bring in the context of, okay, who are we? What do we care about? And then how do these priorities align with who we are and what we're doing? care about. So it's a really thoughtful exercise. It's useful if you have somebody who can lead you along the way. But I think I've seen it happen numerous times in having led these sessions, that there's a real eye opener for the founders, that there's many variables that play what, they may be really passionate about. Look, we just have to get to market. We've got to find product market fit. I've got... I've got pressures from my investors. I have to generate revenue. Nothing else matters. But then they're hearing some other voices, they're hearing some other contexts and really realizing why this is an important prioritization exercise. And it might be that the founder's priority takes hold and that is the precedent for two or three, four quarters or a year at a time. But there will be a point where it's gonna start to shift and... Ira Grossman (19:24.494) the priorities are going to start to change and become more strategic as a business versus just getting that initial product market fit and some initial revenue in the door, which is all anybody's going to care about appropriately early on. So I think the net and all that is get all the stakeholders in the room, again, whether it's three people or 30 people, have a really frank conversation about what's important to everybody when it comes to the product, and then try to really... quantifying and prioritize what that means to the business. And at the end of the day, say, look, if we only have three things we can work on, what's your top three? And that sort of starts to pivot it from a conceptual conversation into a more tactical conversation about the actual product and solution. It's fun and it's healthy if it's done in the right context. Peter Dean (20:13.074) So. Peter Dean (20:18.841) And so this, this is something obviously, after you get a couple of customers, sometimes you get a big customer. I know you, I've been in conversations or heard you talk about this before you get a big customer and then they start driving the product roadmap. How do you, how do you deal with that? Because you still have to sell this to other people. Like you can have a scenario where a company gets kind of in trouble because it's built for one company. And how do you, how do you deal with that? Ira Grossman (20:45.202) Right. Yeah. No, it's a great question, Peter. Um, and it's a real conundrum, especially early on. So, uh, the earlier are on you are in the business, the more likely that, um, you're going to let that drive your roadmap and that might be okay really early on the, the more you progress in your journey, the more dangerous that is going to become. Uh, so what I have found, to be successful is to start to think about the concept of a client council. And it might be three clients early on, it might be 30 clients later on, but key stakeholders from the client side, and I've seen this dynamic happen, which is really cool, is that you get a client, they come in, they say, this is the most important thing for us, we have to have this. And whoever's listening to that, whether it's the founder, whether it's somebody running client, They're trying to listen intently. They're trying to really make the client happy. I've seen that same idea come from the client in a room full of other client stakeholders. And the conversation changes to, oh, we didn't really think that was as important as these two other things. And they start to get into an interaction and a debate around what's really important. And that's been a really powerful tool in my experience. to try and really suss out what's important to the larger group. So that's one technique that I've seen successful. Another is to put some economics behind it. Say, look, we love you, client A, and we're gonna do everything we can to satisfy you, and 30% of what you're asking for, everybody in our client base needs. So we're gonna build that. Here's our roadmap, here's where you fit in that roadmap. Oh, by the way, here's another reason why the roadmap's so important. 70% of what you're asking for is a total one-off that only you care about, and we understand that, you're important. Here's what it will cost for us to do that. If you wanna partner with us on that, we'll build it into our roadmap. And very quickly, you find out how serious they are. Sometimes they come back and they're willing to spend, and it's still as important. Many times it's, oh. Ira Grossman (23:08.094) Yeah, we're okay with the 30%. We can wait on the 70% piece. That's a one-off. It's not as important as we thought. So those are two different techniques. Peter Dean (23:15.497) So it's, that's us is out people saying, I want all this stuff. And then that'd be nice. The nice to have turns into really the need to have, and it helps level instead of you reacting to kind of what they say. Ira Grossman (23:27.642) Right. It's also, so the proactive answer to it is get your, get a, an external facing version of your roadmap, which may be a variant of your internal facing, but get that external facing version of the roadmap proactively in front of your clients so they actually know what you're working on and know that there's some interesting things coming and know that. If they ask for something, it potentially changes that trajectory for everyone. So that also starts to change the relationship and change the expectation from the client. But it's a, it's a great problem. I mean, you, you want to have those conversations. You just don't want to become subject to answering to one client's requests and building, building that client's product versus building your vision. Greg Moran (24:15.46) There's two things that you just said that are both just incredibly powerful takeaways, I think for founders who are starting to hit that kind of growth trajectory, right? Where, you know, an MVP, you're building just that, right? It's, you know, there's probably not a lot of feedback that you're really getting at that point outside of what you're soliciting from customers. But as you start to actually get those customers, I, you know, one of the areas of pushback that I've heard recently are, and not this isn't pushback to... to you, but this is a debate I was having with somebody, which is, well, we're too early. We can't do a client advisory council. We can't do the client meetings because they're not gonna give us information. You can't get competitors in the room. And quite honestly, I've had the same exact experience as you multiple times, right? Where it's really this amazing thing that happens when you get people kind of in the room, literally or figuratively. Ira Grossman (24:46.991) Mm-hmm. Greg Moran (25:09.96) Those priorities that somebody is pounding the table on saying you have to deliver this you've got to look we're gonna cancel our contract Suddenly those things melt away when you're in a more kind of rational balance environment like that, right? Where people are actually weighing in and oftentimes, you know What we find is what I've found is that companies become so myopic in the way that they're thinking about it They're not even thinking about what's actually possible outside of their little world, I need you to replicate this functionality for me, right? But you get them in a room. It's like, holy crap. I never actually thought about that before. Now all of a sudden those priorities start to, you know, that, that pounding the table priority or demand starts to really melt away. I think it's just an incredibly important thing that you can do. Look, if you got a couple, a couple of customers, you can do this, right? It's not, this isn't something you have to wait until you've got 200 customers to do. Ira Grossman (25:36.708) Right. Ira Grossman (25:42.915) Right. Ira Grossman (26:00.634) Right. Yeah, exactly. And you can do a 20 minute Zoom meeting with three customers. And it's about building the muscle. That's what I, you know, both the portfolio founders we talked to at Evergreen and, you know, those I work with on other boards. It's all about just building the muscle early on in all of these areas and getting some practice at it and yields great results. So start. Greg Moran (26:04.249) and you can do that 20 minutes. Ira Grossman (26:29.858) start small, build the muscle, find out what works for you. But getting the voice of the client in a way other than them coming to you reactively just yields great results. Peter Dean (26:39.768) Mm-hmm. Greg Moran (26:42.82) Yeah. Are there frameworks that you would point people to that you're particularly, you know, like I know, um, I mean, I know there's a lot of frameworks around building roadmaps and things like that, but are there, are there frameworks that you're particularly, you know, a fan of or that you would point people to? Ira Grossman (27:01.811) I'm not, to be honest. I mean, there's tons out there. And again, this is not rocket science, just in terms of the manifestation of it into a roadmap. Any product owner worth their salt in the agile world today is gonna understand all of those sort of elements that need to be on the roadmap. I think the more potent piece is getting into a mindset of product prioritization that all stakeholders need to be at the table on a quarterly basis to have a really healthy debate about what's important to the business and why and how it aligns back to the values of the business. To me, that and that's an amalgamation of lots of people who've written on this and my experiences over the years. But to me, that's sort of more important than. the sort of tactical framework that you can apply to this because there's just a ton out there on that. I will say though, thinking about, getting that right product owner in place. And if you decide it's one of the co-founders, fantastic. If you decide you wanna hire somebody for that, I just think it's hard not to have that. It's almost as hard as not having a sort of a technical leader if you're building a... software product and you don't have a CTO equivalent, when you're in startup mode, it's really hard. Very quickly, it's pretty hard if you don't have somebody with that product mindset. Peter Dean (28:39.397) That's a good lead in. So I know you've helped hire or at least get people in place for that product leader. What, like as a high growth startup and you're thinking of hiring someone like that, what kind of would you be looking for in a person like that? Ira Grossman (28:57.186) Yeah, I mean, my thought is you don't have to go out and hire a chief product officer. It probably doesn't make any sense, both strategically or fiscally to do that. But a good product owner, somebody understands the mechanics of your agile development. Somebody who can be a true partner to the software engineering team and act as a bridge between Peter Dean (29:03.176) Yeah. Peter Dean (29:20.946) Mm-hmm. Ira Grossman (29:23.734) leadership, sales, marketing, everybody who's passionate about product deliverable and the engineering team, somebody who can be flexible enough to bridge those two worlds and have great organizational skills is just a really big asset. So flexibility, organization skills, some good vision makes a difference if they have design capabilities. Fantastic. But you can get that from a third party. I'm a great example. Like I can look at a. I can look at a product design and tell you pretty quickly what I feel about the UX. Generally had pretty good results there, but I can't draw a stick figure. So I don't have the inherent design capability, but I have a sense of what's useful for a user, what is easy, what's efficient. And design as a differentiator is a really cool tool also for. Peter Dean (30:11.261) Mm-hmm. Ira Grossman (30:22.606) for founders to think about. You can come into a space that might be, assuming you're not creating something brand new, but you're more likely disrupting or improving a market, you can really use your design to differentiate because there's so many, unfortunately there's a lot of poor designs out there. There's a lot of inefficient design. When I was in life sciences, I was like, that was a new vertical for me. when I started that business and I was blown away that 95% of what was out there all looked like a medical form. No matter what they were addressing in the industry, they made everything look like a medical form. It was horrible. So we built a business that was so the other end of the spectrum that people's head would just explode. You could do it this way. You can think differently. So... Greg Moran (31:13.631) different things. Ira Grossman (31:14.254) So I really think design as a differentiator is something that founders should really grab onto when they think about their product strategy. And it doesn't have to be earth-changing Apple level design strategy, but it can be just sort of nuanced ways that again, it's more efficient for your users to operate and maybe more fun. And it's something in a lot of different sectors people don't think about. Can you make the software fun in some way? Peter Dean (31:24.745) Mm-hmm. Peter Dean (31:40.487) Yeah. Greg Moran (31:41.856) What is the right time do you think where somebody starts to, where you do recommend a company start to really think about that, you know, VP level, C level product leader. Like how do you judge when the right time comes where you may be starting to outgrow say the founders capability or something along those, in that area? Ira Grossman (32:05.774) Yeah, it's a hard call. I don't think there's a hard threshold, but general sense is if you can get your minimum level product out the door without that investment because one of the founders has enough passion to drive it and or you might get a little bit of third party help, that's fantastic. I think once you've gotten, you can get past that, you've got some product market fit, maybe you've got a little bit of real ARR on the table. Greg Moran (32:08.02) It's a hard problem, I think there's a hard ground truth, but it's a general sense, if you get the idea that you're on the front of a company, you're down the best knee. Greg Moran (32:26.033) That's fantastic. They want you to get it. It's kind of standard. Ira Grossman (32:36.358) I think, again, you don't have to think about hiring a chief product at that point. But bringing in a really good product owner slash product manager who could start to lead to charge for you probably makes sense at that point. And that person may or may not grow into the true leader. And if they don't, I think once you're in the SaaS world, you're starting to look at a small Series A. You're in a million plus of ARR. That's probably the point where you want to have somebody who's a little bit more in a leadership role. But I think you can get pretty far along to that point, as long as you have some of those core concepts in place and you're not just completely winging it. Because there is, just like tech debt in your software code, you're gonna have a lot of tech debt in your product strategy if you don't have anybody thinking about this early. Greg Moran (33:10.865) Yeah. Peter Dean (33:25.008) Mm-hmm. Greg Moran (33:31.24) Yeah, yeah, it's especially, I mean, you see this, you talked about design, right? You see this in design too, all the time, where you start to build these kind of Frankenstein looking systems, right? Over, you know, over time, and suddenly you're going back and you're trying to redo this stuff, it just gets incredibly expensive and incredibly, incredibly hard to deal with as the complexity of the system starts to grow. Just, you know, dealt with that so many times where you'd say like, hey, can't we just reskin this thing? Or can't we make it look? know, eventually over time the answer becomes no, you can't, right? It's, there's just too much. Peter Dean (34:06.437) Is that, is that some of that inevitable though, that you have like your minimum viable product, you sell it and then you start selling it and you get, then you have to go, okay, what do I do? I know you have to probably, I know I'm not the expert here, but they have to look at how did we engineer this and we have to kind of rebuild that so it scales. And then the design piece too, you have to say, Hey, where is this going? That's that roadmap. Maybe it could help. Ira Grossman (34:07.226) Yeah. Ira Grossman (34:32.334) Right. Yeah. Peter Dean (34:34.449) to say like, we can't get stuck in this like, bad place that happens to, does that happen to everyone? I mean, I don't know when someone that I haven't heard that conversation go on for but. Ira Grossman (34:39.042) Yeah. I, right. Yeah. I think, I mean, it's an organic process, right? So both your, both your engineering design and your UX and UI design are going to evolve over time. However, I think there's lots of examples that still exist out there. Today, today you can avoid a little bit more because of design frameworks to build front end software are just a lot. Peter Dean (34:48.87) Yeah. Peter Dean (34:56.775) Yeah. Ira Grossman (35:07.934) easier and more powerful. But there's still a lot of examples, to Greg's point, out there of that nobody just worried about the front end. They just wanted to functionally work. And nobody thought about the user experience until it was too late. And then it's really hard to just completely reskin it at that point. So it's just something that's worth modest investment up front to really think about user experience. And again, the other. Peter Dean (35:10.621) Mm-hmm. Peter Dean (35:26.343) Yeah. Greg Moran (35:35.366) in the... Ira Grossman (35:36.41) The other extreme I've seen as well, which is like all you care about is UX and UI, and you don't have any functional utility. So you've got to have some balance. Right. Peter Dean (35:41.09) Over. Peter Dean (35:45.553) They over you could overspend to right like they're we have to build this awesome thing and they're so focused on that. Like wait, we need a customer like we need a couple of those. Ira Grossman (35:50.723) Right. Right, right, details. Greg Moran (35:55.74) It ends up being like the showers in a lot of the hotels I stay in, right? Like, you're like, wow, that is a work of art, but I can't get the water to run. Like, I have no idea how to turn the freaking shower on. Right? I mean, that's the, right, there's got to be a... Ira Grossman (36:00.398) Yeah. Ha ha ha. Ira Grossman (36:09.351) That's it. Peter Dean (36:11.353) It's a hidden tile. It's like the hidden tile. Greg Moran (36:14.184) Or trying to turn off your iPhone, right? Like, I don't know, my iPhone's been out for 12 years. I don't know really what to do, right? And, but I think that, you know, bored to the point that you see that less, right? Where it's really so design heavy. But you certainly see these examples. Ira, you and I have lived this, rumors too many times, I think, to mention, for, to save their reputation to people. Ira Grossman (36:20.851) I'm sorry. Greg Moran (36:44.496) But you have systems that are built by engineers that are, and not to beat up on the engineers, they're bulletproof systems, right? I mean, these things can withstand anything, but they're horrible, right? And that's the thing that, you know, it's so easy to just invest a little bit now. I mean, you know, when you and I were starting our first companies, like, you know, Upwork, Ira Grossman (37:08.814) Yeah. Greg Moran (37:13.496) and things like Fiverr and things like that didn't exist. It was really hard to pull in a freelancer and just say, give me 10 hours of work around making this UX usable and friendly. It softened it up. And now I think those resources are available everywhere in the world for you. And you can just start to invest a little bit of money to really, like you said, differentiate yourself just simply by the fact that Ira Grossman (37:16.87) All right. Peter Dean (37:26.365) Soften it a little. Yeah. Greg Moran (37:42.74) The software doesn't suck. Full again, right? Ira Grossman (37:45.91) Right. Yeah, and that's why I really like, I really like founding teams. Because I think when you have, when you have a visionary founder and a technical founder and they can work together and have that conversation and balance out the degree of technical complexity versus user experience and design, that's really healthy. And it works in other ways. So when you have a really technical founder though, you more often than not can end up down that rabbit hole where... Peter Dean (37:56.294) Mm-mm. Peter Dean (38:03.004) Yeah. Ira Grossman (38:13.466) There's like all this technical, what they perceive as really sexy, cool functionality that 80% of the clients don't care about and can't use because it's so complex. So that's a trap that highly technical solo founders fall in, which is again, why I love the sort of founder teams where you can have a more balanced view. Peter Dean (38:19.933) High function, yeah. Peter Dean (38:26.822) Yeah. Greg Moran (38:39.732) So wrapping this up, and everyone's been very well behaved. I do have to say. Ira Grossman (38:46.882) I was going to say this is when we were allowed to officially devolve into abuse, right? Greg Moran (38:50.952) No, no, before it devolves, before it devolves. If you were to just give kind of three pieces of advice, to a high growth founder, they're starting to deal with some of the issues around this stuff, they've got the MVP market, now they're getting customer feedback, what are the three pieces of advice that they should be thinking about right now? Ira Grossman (39:17.902) Yep. Um, number one, take a real hard look in the mirror and determine if you or any of your co-founders have that skillset to be the sort of de facto product leader for as long as needed and if the answer is yes, fantastic. You know, run that clock as long as you can. I was in that mode for years in, you know, two out of three businesses and I enjoyed it and we got great leverage out of not having to pay a head of product to do that. Peter Dean (39:32.143) Mm-hmm. Ira Grossman (39:46.998) But if you, but the answer is no, then really think about at least getting that first person in place. So have somebody who's passionate about it and can really focus on product as soon as you can realistically afford it. Number one. Number two, do that, do that transparent exercise where you bring the stakeholders to the table and have a healthy debate about what's important to everybody and how that fits into your core values. as a company so that you can really go back to that North Star. When you're getting 15 client requests and 10 requests from sales and marketing for changes, you wanna be able to go back to that conversation and say, okay, why are we doing this? Does it align with a North Star? Should we be doing it? Should we be doing it this quarter, next quarter or next year? Or not at all. So get yourself in a place where you have that framework. And then three is just know that it's going to be absolute chaos and that you're going to have to reprioritize sometimes on a daily basis, but more often than not on a weekly or monthly basis. And that's okay. That's what's cool and exciting about building software in my opinion, is that you can, you can pivot, you can, you can make changes, you're going to make mistakes, you're going to make the wrong calls, but you can course correct as long as you maintain this sort of open, transparent. vigorous approach to this whole thing. Greg Moran (41:17.484) Yep. I think that I think it's a great way to wrap it up. Obviously, I know what you're working on today. But normally when we're wrapping these things up, we're you know, get what are you working on? What are the kind of the things that you're that you're dealing with today? How does somebody who maybe wants more advice or to get in contact with you can reach out to you. Peter Dean (41:18.823) That's cool. Ira Grossman (41:25.894) Thank you. Ira Grossman (41:40.662) Yeah, my whole gig at this point in my career, and I had this epiphany with our mutual friend, Jeff Evans, who you've had on the podcast, is I'm at the point in my career, I want to be an entrepreneurial sherpa. And I want to really help founders get on that rope line and find their way through this complex founders journey, which you guys are talking about all the time on the podcast. So that's what I love doing. Evergreen is the vehicle to do that. Evergreen Mountain Equity Partners is Greg and I's baby where we get to do this on a semi-professional basis and use some of our operational experience to help others. So that's where my passion is. That's where I spend my time as well as individual and personal investing in startups as well that don't fit the Evergreen model. So people can pay just... just email me Ira at [emep.io](http://emep.io/). So my parents knew I wasn't too sharp, so I only have a three letter name, IRA, it's pretty easy. Ira at [emep.io](http://emep.io/). Peter Dean (42:48.585) But I'll tell, okay, here's the inside baseball. If you wanna get funded, you have to talk to Ira. You can talk to Greg, but you definitely have to talk to Ira. Ira Grossman (42:55.078) Good. Greg Moran (42:58.204) Well, wait a second. Ira Grossman (42:59.383) If you want love, talk to Greg. See, love, are you? Greg Moran (43:01.798) HAHAHAHAHA Peter Dean (43:01.933) Yeah, you have to convince Ira and then maybe you'll get a deal. Greg Moran (43:07.796) There's Irish-favorite saying to me is you fall in love with everybody. Peter Dean (43:13.169) That's the rule. So everyone's pitching Greg. That's great. But you got to pitch Ira too. Ira Grossman (43:14.808) Here we have it. Greg Moran (43:18.46) what I'll say, Ira is definitely the more rational one out of our partnership of two. I definitely the slightly more eccentric off the wall one out of two. So it is a good beginning, yeah, but if you want actual like real answers that aren't either going to get you injured or put out of business, talking about Ira's problem. Ira Grossman (43:23.379) Thank you. Greg Moran (43:42.8) If you want to have a pile of fun, I'm your man. Ira Grossman (43:45.613) Yeah, he's your man. Greg Moran (43:50.26) Well, this was awesome. I promised you it wouldn't be too painful. I didn't call anybody old, although for the record, I am the youngest on this call. No insults at all, no stories, no terrible stories that we threatened you with were told. So we're going to have to wait for that. Ira Grossman (43:57.19) I'm going to go ahead and close the video. Peter Dean (44:07.985) You didn't ask question five. Greg Moran (44:10.468) Wait, what's that? Ira Grossman (44:15.216) We're going to do a whole other podcast on question five and other various inappropriate things that have happened in our journeys. Peter Dean (44:21.701) And if you'd like to know what question five is, you should send an email to Ira or Greg or reach out to them on LinkedIn and you could, maybe they'll tell you. Ira Grossman (44:29.101) I'm sorry. Greg Moran (44:31.476) That's right. That's for subscribers only. If you subscribe to this podcast today, we'll tell you a question number five. So, we'll get you back. Somebody, we were doing a recording yesterday with two guys and they were talking about, it was all about like co-founder relationships and stuff. And during this, somebody actually suggested that Peter and I, Tim Ferriss does these. Peter Dean (44:36.397) Even though you can't subscribe. Peter Dean (44:42.322) Did he have? Greg Moran (44:59.548) does these podcasts where it's like him and Kevin Rose, and they basically just get drunker and drunker as it goes through. So I actually think we should do that with the three of us one time and everyone of us like. Ira Grossman (45:04.939) I'm sorry. Ira Grossman (45:10.375) I think it's a great idea. I think we should add in hot wings or something like that. Okay. Peter Dean (45:15.655) Yeah. Greg Moran (45:18.706) Somebody ends up in prison. This was great. Thanks for coming on. I already promised you it wouldn't be too painful. It wasn't. So. Ira Grossman (45:26.03) No, thanks, Jens. This was fun. Hope I could share something that was useful. Greg Moran (45:30.492) Absolutely, absolutely. Yeah, great takeaways, I think, for any founder. It's just stuff that's super important. So see you next time on the Founders Journey podcast.