Episode 248
How Greg Moran Applies AI and Innovation to Solve Real Problems for His Customers
Greg Moran, a serial entrepreneur, venture capitalist, and podcast host who has scaled multiple businesses and achieved successful exits. Greg shares his founder’s journey, from starting his first business at 23 with no experience and no contacts, to building and selling a HR tech company to a…
Show notes
Greg Moran, a serial entrepreneur, venture capitalist, and podcast host who has scaled multiple businesses and achieved successful exits. Greg shares his founder’s journey, from starting his first business at 23 with no experience and no contacts, to building and selling a HR tech company to a large private equity firm. He also reveals how he overcame challenges, pivoted his way to success, and leveraged his network and mentors to grow faster. Greg also discusses his current ventures, including his podcast, The Founder’s Journey, where he interviews other founders and provides insights and advice for scaling a business. Greg also shares his views on AI, blockchain, NFTs, and other emerging technologies, and how founders can stay focused on what matters most.
Chapters:
- 00:00:00 - Welcoming Greg Moran: Serial Entrepreneur & Venture Capitalist
- 00:00:29 - Greg's Beginnings: From First Business at 23 to HR Tech Success
- 00:03:26 - Mentorship: A Key to Greg's Entrepreneurial Growth
- 00:04:55 - Teamwork & Collaboration: Foundations of Startup Success
- 00:05:53 - Overcoming Startup Challenges with Mentor Guidance
- 00:13:29 - Business Clarity: Staying Focused on What Matters
- 00:20:45 - Exploring AI's Impact on Business and Tech Startups
- 00:24:01 - Final Insights: Scaling a Business & Future of Tech Innovations
Links And Resources:
- Greg Moran on LinkedIn
- Evergreen Mountain Equity Partners
- The Founder's Journey Podcast
- Amplafy Media
- Hector Santiesteban on LinkedIn
- Hector Santiesteban on Twitter
Thanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!
Full transcript
[00:00:03] Hector: hello and welcome to another episode of the how to scale a business podcast. My name is Hector Santia Esteban and I'm your host for today and we're here with Greg Moran and had to get started. We had hit the record button because we're going to talk about making things easier for high growth founders or people who a growth stage and so I'm excited to have you on Greg.
[00:00:21] Hector: Thanks for being here.
[00:00:22] Greg: I appreciate you having me on, Hector. glad to be joining.
[00:00:25] Hector: So were just talking about it and I'd love add some context into what you were saying. I think that superhero or the, perhaps the villain origin story, I think always has an important part of the story you've built a couple of businesses, you've had some big exits, you've done the thing, you've climbed the mountain and now you're turning around and, you're the Sherpa, if you will, helping people up the mountain again, but talk to us about what some of those mountains were and then, maybe to what's, most relevant to what you're doing today with founders.
[00:00:52] Greg: Yeah, sure. So look, I've been super fortunate, In that, I've managed to have, start a few companies, a couple of them that, turned into fairly significant size companies and a couple of nice exits along the way. But along with that, like every founder, I, had.
[00:01:08] Greg: Many more than those two that didn't work out the way it wanted to, you know, andwhen I first started my career as, an entrepreneur, as a founder, it was, for me, I think about it in those terms, was a career. It wasn't something that I was going to do one time and go, and then go back into another corporate job or something like that.
[00:01:26] Greg: so when you think about what are the mountains to climb? I didn't come into this with this wealth of contacts or or anything like that. Right. I mean, I literally started this, started my first business as a, 23 year old.
[00:01:39] Greg: with no experience, didn't have the Ivy league education or anything like that, took the 1, 500 in life savings that I had at that point, and started it manage to just continue to build from there. I think the entrepreneurial journey. Is it's just one mountain after another, right?
[00:01:53] Greg: And, you climb one and you got to descend down the other side of it and get ready to climb it again. And whether that means, a lack of funding or lack of experience, or it didn't have the right people and needed to, replace those people or the product wasn't quite right, or you lose customers.
[00:02:08] Greg: it's all the same stuff that I think every founder experiences in that journey and they're all mountains. and so my experience was no. different. this was, my journey is one that has taken over, 20 years or so of being a, being a founder. And after my last, what you and I were talking about is after my last, exit company called Outmatch, it's now called Harvard, in the, it was in the HR tech space.
[00:02:31] Greg: So enterprise SAS software for HR tech, Sold that to a large private equity firm, stayed on as a CEO for about 18 months and decided it was time to move on from that really totally shift, And really devote my time and my attention largely around really trying to help other founders make their journey a little bit easier.
[00:02:51] Greg: then I'm happy to get into that more. I'll pause there for a second and how we're doing that. But, But happy certainly to get into that more.
[00:02:57] Hector: Yeah, I'm curious. you've had, you said there's a couple of mountains. Are there some key experiences when you look back to those first couple of, journeys, if you will, that you either lean on or find yourself coming back to often? Or, I've heard someone said that history doesn't repeat itself.
[00:03:16] Hector: It rhymes. And so do you see yourself whether it's going through similar phases or stages are there similarities between these different mountains? Yeah,
[00:03:25] Greg: there's no question. I think the one recurring theme, if I reflect back over, a few different companies, one recurring theme is it's, there's always been a person or two who've come along and sometimes, across multiple businesses, even the same people, that I've worked with my career, but mentors that I could really lean on when I didn't have the experience that would actually.
[00:03:49] Greg: Help me to think about things in a completely different way. And I think having individuals that were willing to help me through the really challenging parts. my last business, we probably ran out of money, five, six, seven times we were legitimately out of business, probably five or six.
[00:04:06] Greg: Times, except nobody told me thatI was so inexperienced. I didn't even know that. And I'm glad I didn't, but it was having other mentors around me to say, okay, just reframe this problem. let's look at this a little bit different. There is a way out of this when those dark moments just seemed so dire, I think that's the common denominator is I always had a couple people that I could lean on that would just help me get through those challenging times, whether they're really dark moments or seeing opportunities that I actually wasn't even seeing. I've got a great story about that, by the way, but, that I'm happy to get into and, a good example of that really this kind of defining moment in my career, but yeah, for me.
[00:04:49] Greg: It was always the mentors and the coaches and the guides. You use the word shirt, but the shirt was that would take me through it.
[00:04:55] Hector: someone told me that it actually isn't an African proverb, which is, it's so sad, but it doesn't matter. It's that if if you want to go fast, go far. Go to group things early. I found myself being that one that wanted to go fast. And as I've 32, but entrepreneur working for my now 15 years.
[00:05:13] Hector: And as I've realized that I've realized that Exactly what you're talking about that, whether they're working with us or whether it's a guide or a mentor or something that there's old, I'm going to go much further when I include or utilize or incorporate other people than I can ever go on my own.
[00:05:30] Hector: And that was a big, knuckle headed, hard headed thing that I had to give up, as an Early entrepreneur. and it took some finding some key people in my life to really wake me up. We're looking back and go Oh, that wasn't actually all you. There was some things that enabled that sort of success or some connections that allowed those opportunities to cultivate themselves.
[00:05:50] Hector: So curious how that's come up in your career.
[00:05:53] Greg: So I think back, great example of this right back in the very early days of my last company, the one I exited out of , about two years ago now, that I referenced a little while ago that we sold to private equity back in the really early days, we were just starting to, mean, I wouldn't even say we had traction.
[00:06:09] Greg: I think we probably had Million in revenue, something like that, but it was slow going. everything was just hard and we kept running out money and we'd have to drip feed this thing. And, one of my mentors guy who has been with me through several careers, who was. Built a very large company, took a public, I'll never forget.
[00:06:25] Greg: At that point, we kept running out of money. He said, you know what we need to do, Greg? He said, we need to go buy a company just a lot bigger than we are so that we can just put a better foundation under this thing. And I said, Martin, like that's not a thing, right? we're this like struggling 1 million company.
[00:06:41] Greg: How do we go buy a bigger company? He said, ask. He said, there's always ways to do it. If we can build a bit, if we can build a rationale, We should explore it. So lo and behold, there was a company that was a competitor of ours. what we had was great tech and we had the ability they have been trying to acquire our tech for a while.
[00:06:57] Greg: And he said, let's just ask them, let's ask them if they're willing to sell. I said, this is crazy, but sure, I'll do it. don't they say yes. And we end up putting together. A deal by getting venture funding for this thing. and going, here's this 1 million company going and buying a company that was doing about 9 million in revenue and instantly overnight, we now are a company with scale, with real customers, with.
[00:07:28] Greg: A history, which we didn't have before we were actually, we were no longer in this feast or famine mode, but we could actually get into this growth mode. It was only because I had 1 person that sat there and said, you're thinking about this problem in the wrong way. Stop operating out of fear. Think about this on a bigger scale.
[00:07:49] Greg: There is a way to do this and I think that's those are the kind of things that having that entrepreneurial support system having that kind of either whether it's a network of other founders or it's mentors and advisors. that have been there that can help guide you. That's how those conversations actually occur.
[00:08:08] Greg: and it took us from that point forward, we never looked back and continued to grow at a really rapid pace to a successful exit.
[00:08:17] Hector: Yeah, it's a great, it's a great example of how different sorts of thinking can really result in just a totally different path that isn't linear. And I
[00:08:27] Hector: think that's the value of having these mentors. when you. Now that you're working with founders, what I really enjoy about having someone like you on who helps a lot of different people is that you got a larger, you have a larger sample size, and you're able to have a maybe a bird's eye view.
[00:08:46] Hector: Or, that the landscape a little bit different. And so are there any challenges that you find are common among founders today? Or, when someone is looking to scale, they've got some things going, they're trying To figure out, they've gone zero to one, but now they're looking to go one to a hundred and there's that old saying that,what got you there, isn't always going to get you to that next place. are there things that you find yourself like either low hanging fruit that people are just missing that they can scoop that up or even things that you find yourself, slamming your hand against your forehead Like if you just. Saw this thing that was just right in front of your face, that if you fixed or did this, that would result in something different.
[00:09:26] Hector: Are those things coming up for you at all in the
[00:09:28] Hector: people that in the clients that you're working
[00:09:29] Greg: absolutely. And the only reason they come up for me is because I've done all the same things myself, right? I was that guy, for other people that said dude, what are you? Thinking what are you doing right now? And so you do see that. I think a couple of the really common things that, I see all the time that number one, this is something that I think was market driven largely where you see there were this kind of mindset of early stage founders on fundraising instead of selling, right?
[00:09:56] Greg: This over reliance on fundraising as an end goal in and of itself. When truly funding outside funding should be to drive growth, not support the business, right? But thinking about fundraising as an end goal, I think is one thing. I think the other thing is just not looking at the unit economics and the real scalability of their sales model.
[00:10:21] Greg: In other words, making their go to market. Making it really hard for customers to buy see this all the time where, you know, companies that have a relatively simple product for some reason, try to make it so complicated that it ends up being this really laborious sales process. And you lose people in the meantime, where if you just thought about the customer journey a little bit easier, made it easier for somebody to go in, get a quick demo of your product.
[00:10:49] Greg: So self select themselves in or self select themselves out. And get them into a free trial, you could really grow a lot faster, but there's this kind of bias of, Hey, my product, it's not that easy, but really it is. You're just making it hard. I think is, the other is the other big, thing.
[00:11:07] Greg: And I think the third thing that, I see all the time is a founder's fear or reluctance to pivot. The reality is. Whether you're me and you look at sort of my businesses where I probably had a pivot 15 times before we got on the right path, pivoting is part of the startup. It's part of that experience.
[00:11:25] Greg: You're not going to get everything right as a professional investor. as a investor, I run a venture capital front. I invested a lot of startups as an investor. I have no expectation that the founder is going to get it right on the first swing. I don't even have an expectation that they're going to get it right on the third or fourth swing.
[00:11:43] Greg: But I do have an expectation that they're going to look at the data and they're going to pivot and keep making those course corrections until they get it right. And there's a real fear, real reluctance on the part of founders in this thinking that like I'm doing something wrong if I admit that my initial plan wasn't the right one.
[00:12:03] Greg: There's nothing wrong with that. You've just got to pivot faster. And do it based on data.
[00:12:08] Hector: Yeah. Greg, I'm sure you've got some, you seem like a very thoughtful, intentional, perhaps systematic kind of guy. And so I'm sure you've got some systems or some frameworks, for founders who want to. go to the next level. And we're going to get into that, but before that, we've got to pay the bills and we're going to take a quick break.
[00:12:26] Hector: Hey y'all. Today's episode is brought to you by amplify media and we are a podcast. On the surface or podcast production company, but really we like to think of ourselves as a genius maker or a platform creator, because chances are, if you're listening to this, you have a mission, a message, a product, a service, something that's going to go out there and change the world.
[00:12:41] Hector: But don't necessarily have the time or the tech skills to be able to get it out there. And so if that's the case, we could help go do. Amplify media. com. That's a M P L a F Y media. com. All the details will be in the show notes. And with that, let's get back to the episode with Greg. Okay, great.
[00:12:56] Hector: So I'm a systems nerd.
[00:12:58] Hector: I'm a frameworks kind of guy.,I love that because it gives me sort of map. It gives me a legend to see things that are, unseeable in business. there's so many different scenarios. There's so many different things and nuances and niches and all the sorts. But. Frameworks give us some sort of, an M. O. Something to fall back on. So is there some sort of general, framework? Are there some stages, some steps, things that you see that founders need to go through if they want to it to this next level that we've been talking about?
[00:13:29] Greg: Yeah, I don't have a fancy title for it, or, it's not the, I've never named my sort of framework around this stuff, I can tell you the steps, right? And, talking in terms of, you know, a little bit around like early stage founders, but this extends to founders at even a growth stage, right?
[00:13:48] Greg: That just stepping back as kind of step number one, stepping back and getting crystal clear on what it is that you do. This is super elementary, right? What it is that you do, why it is that you do it and who it is that you do it for. And then being able to articulate that in a few sentences, right?
[00:14:17] Greg: Incredibly simple language. people use this kind of, if I told my mother what I do, will she understand? If I tell my, my, elementary school kids, what I do, will they understand? however you want to think about that, being able to get that level of clarity. What do we do?
[00:14:34] Greg: Why do we do it? Who do we do it for? Because if there's complexity, Or ambiguity, it causes huge friction in the process. So that's step number one, getting that kind of clarity.
[00:14:47] Hector: Is it okay if we double click on that? Because I think that there's probably some fleshing out. So when I hear what Why and who, the, what seems like the product or service, the, why, maybe that's the vision or the greater problem that someone is solving. And then the, who is their ideal customers, right?
[00:15:04] Hector: their target customers. is it more than that? Or when you think of it, does it break down to any more than that?
[00:15:10] Hector: or what are those components like?
[00:15:12] Greg: No, I actually, don't think it really breaks down to more than that. I think it is that simple in principle, but. Every day I talk to founders and ask that question, what do you do? And more often than not, I get really long, really elaborate, really complicated, really buzzword heavy or industry heavy answers to that question, right?
[00:15:37] Greg: What do you do should be a really simple question to answer, right? And, but not having it be full of that sort of the buzzwordy jargon, but tell me one sentence. What do you do? We make X software. We create Y solutions for X market, right? really simple. If I think about it, my, my business today, I'm the interim CEO Of a company right now in my other business is a podcast.
[00:16:12] Greg: We launched a podcast called the founders journey podcast. Very, sure. Same audience that is listening to this. Hopefully we'll, listen to ours as well. And if we think about that, what do we do? That question of what do we do? We have a podcast to help inspire and educate, founders globally.
[00:16:31] Greg: That's what we do. That's and it's, but it's that level. But when you start to get into technical products and things like that, it really becomes, there's this bias toward being able to like providing answers that nobody, even people in the space don't under don't understand. So yes, it is that simple, right?
[00:16:51] Greg: This is the product. But explain to me what the product does in a sentence that I can understand if I'm not Right? So that's the what it is that we do. Why it is that we do it. What's the emotion you're trying to evoke? what is the purpose of what you're doing? And it doesn't have to be some deep on a deep spiritual level, right?
[00:17:12] Greg: But why are you doing what you're doing? Very simply, right? That's going to resonate With that target market, and then that goes to the third point of who you're doing it for really defined for me, who are those? So if I go back to my podcast to use as the example, it's for the global founder.
[00:17:29] Greg: With generally about a million dollars in revenue, that's the market that we focus on. So tell me exactly who you're doing it for, right? It's getting that explanation and that alignment in your own head and with your team and with investors and with the market around that simple clarity of vision.
[00:17:48] Greg: Step two on this. Would then be to take this kind of broader explanation and then narrow and narrow and narrow and narrow some more. And when I say that it's because startups have early stage companies have such limited resources. That this goes to the mistakes you question asked before, one of the things you see all the time is they try to go out and serve a market that is way too big for what they can possibly do.
[00:18:16] Greg: The worst term in the history of venture capital is TAM, Total Addressable Market. It is the most useless term that has ever been created. It literally is a term that says, this is my conceptual. Number of buyers of whom I will never reach even 1 percent of them, right? Stupidly narrow on this, get really tight to say, here are the 250 to 500 customers in my ICP that my particular value prop, that clarity of vision is going to resonate with, go out, get a handful of those to become customers, get a couple of those to get you a case, give you a case study and start to expand slowly from that core.
[00:19:03] Greg: What this does. Is it not only creates scale by getting tight, but what it also does is reduces your reliance on external funding. If you can get really narrow and go out, you can go hand to hand combat with 250 to 500 people, right? And get. A couple of people to buy and service the hell out of them and get that case study.
[00:19:28] Greg: You can do that without millions and millions of dollars of venture capital, which is going to equate to dollars in your pocket at that eventual exit.
[00:19:36] Hector: Yeah, it's a great focusing exercise because you what you're able to do is you're able to start not broad, but you're able to, make it one sentence and the better that sentence can be. obviously the more clarity you're going to have, but I feel like there's a series of one sentences that you can have and the more that you can break down your
[00:19:58] Hector: what and your who and your why.
[00:19:59] Hector: And then you can continue to do that. And I think that's just a great framework. so maybe you do have it. the one sentence founder.
[00:20:05] Hector: We've got a few minutes left here.
[00:20:07] Hector: would like to take the time to talk about is looking forward for founders. I think the challenge that a lot of them have is there's so many shiny objects. there's so many rabbits out there that we can chase. and I mentioned at the beginning that I'm one that I love these new things.
[00:20:21] Hector: And I love, Shiny objects and rabbits but are there any that you're particularly paying attention to or staying away from? the easy ones are the A. I. S. And the, I guess before that it was, blockchain and there's all these things that become trendy. and if T's you know, are there things that you're like paying attention to or, Conversely, cautioning founders to stay away from.
[00:20:45] Greg: look, I'm a huge believer in AI. I fundamentally believe that AI is going to change the way that we live, the way that we work. everything about our lives will change because of AI. I did not feel that way about blockchain. I did not feel that way about crypto. I certainly didn't feel that way about NFTs.
[00:21:01] Greg: I still didn't really understand the purpose of an NFT, in any kind of practical reality. and I think the biggest thing for founders is let's just focus on AI for a second. We're so early, right? We are so early stage in what AI will be. you go on to chat GPT or something like that. 20 years older than you, Hector, and I remember the days of getting AOL disks in the mail when the internet was first starting and
[00:21:28] Greg: hearing
[00:21:29] Hector: I stocked up on those. I, you get like a, you get 20 or 40 hours, so we'd run through them, I'd run through it, and I'd create a new account, and my mom would, she'd be, she, that's actually a funny story. She would be curious how, why I would be store, like taking all of the free CDs from my phone.
[00:21:43] Hector: Friends houses and asking if they got it. So I remember those. it might even be like punch cards, right? I don't know if that was there. I was, that was before my time. but even like those floppy disks
[00:21:52] Greg: That was it. When I first started, when the internet, when, AOL first became a thing, you were literally getting the floppy disks, right? there were literally floppy disks that you were getting. And, when you look at where chat GPT is today. We're going to think in a decade from now, the same thing about where chat GPT is today that we're joking about with the old AOL floppy disks and the dial up, that crazy noise that you'd hear, right?
[00:22:16] Greg: That's where we are. We are so early stage. And I say that because it's incredibly easy for founders to really get themselves wrapped around that axle of, I've got to be focusing on AI. I've got to be doing more here. I've got to be doing more there. Be thinking about these things. But build a fundamentally good business on today's technology, because one of the biggest challenges you see is founders will get way it by definition, we're visionaries, right?
[00:22:42] Greg: That's why we do what we do. We see things that most people don't. And when we see that we have a tendency to act, right? I love new tech.even with my podcast, I'm constantly applying, I drive our producers insane because I'm constantly Playing with like new technology to experiment with it and stuff.
[00:23:01] Greg: That's fine, but understand where it fits. in that, the whole chronology of a startup, we are very early stage, stay focused on what it is that you're doing today to deliver to your ICP, do not get far ahead of the market. And that's really good at saying no, or saying, look, it's a great idea.
[00:23:20] Greg: But I need to wait.
[00:23:22] Hector: Yeah. Fantastic advice. I think, a very, informed, wise, insightful advice. Greg, you mentioned the, um, the podcast, the Founder's Journey. definitely go, we'll link that up in the show notes. Is there anywhere else that, that people can go get connected with you?
[00:23:38] Greg: Yeah, I'm super active on LinkedIn. you can find me. It's just that Greg Moran, G R E G M O R A N. and uh, so I'm super active there. Yeah, definitely.
[00:23:46] Greg: I'm on x, which sounds oddly dirty, but the former Twitter and LinkedIn. So yeah, definitely find me there. Hit up our website at the founders journey podcast. com. You can connect with me there and but I'm pretty accessible.
[00:24:01] Hector: Greg. I'm gonna wrap this up with, a challenge to you and that is in one sentence, what is the secret to scaling a business?
[00:24:09] Greg: Patience. Give you one word.
[00:24:12] Hector: I love it.
[00:24:12] Greg: This stuff does not happen. Overnight and I know been incredibly fortunate my career and I know people who if you look at financial metrics and things like that, make my head spin in terms of what they've accomplished. And I think the biggest common denominator is it took a long.
[00:24:34] Greg: Time. These things just take a while. Be patient. Enjoy the journey. Because if you're solely focused on the exit. And so many founders are right, we get ourselves so we're talking about selling our business the day it starts, build the business you want to work in for your entire career, build a team you want to work with, build a brand that you're incredibly proud of, build the products that, bring tears to the market's eyes because you're doing something so innovative and so revolutionary to solve a problem that they're having, build that business and let the exit come to you.
[00:25:10] Greg: Just be patient.
[00:25:11] Hector: Yeah. Listeners. You heard it. Greg said it much better than I ever could. And, we appreciate being with us today. If you got some value out of today, we would love and appreciate a rating or review wherever you get your podcasts. And if you know someone who's in the midst of scaling a business, send them this episode.
[00:25:25] Hector: Let's grow the community together. And, as always, we appreciate you being a part of the community. We'll see on the next one. There you go.
About How to Scale a Business
How to Scale a Business gives founders the systems, hiring frameworks, and operating habits to grow past themselves. Host Hector Santiesteban breaks down what actually moves a service business from owner-driven hustle to a company that scales — in practical, do-this-next episodes.