00:29  Hey, welcome back to the program. And today we are so blessed to have with us Adam. And I love what Adam does. So this is gonna be a really fun interview. Adam, will you tell us who you are and what you do?

00:41 Yeah, absolutely. Thanks for having me, Todd. My name is Adam Coughlin. I am one of the co-founders and the chief marketing officer of a company called York IE. We are a strategic growth and investment firm, which really just means that we try to help technology companies grow. We do that through two different ways. One is on the investment side of where we invest in early stage B2B software, recurring revenue companies. And then we have an advisory services side of the business where we help companies with both strategy and operational execution in finance, product, marketing, and sales.

01:20 Love it. And so primarily dealing with SaaS companies, right? And the technology with month of recurring, that's kind of another way for saying SaaS, right? 

01:28 Yeah, absolutely. Yes.

01:29 Or is it different? OK, OK. So as you jump into the SaaS world, obviously, there's a lot of players here and there's a lot of people that need to hear this interview, I'm guessing, because it's it. There's a lot of ways to screw it up. And so everyone thinks that jumping into a recurring revenue model is easy. Tell us what you see. What are, as you are trying to, well first of all, tell us why are you into this marketplace? Have you had something like this before personally, or what kind of drove you into this advisory, this type of advisory?

02:01 Yeah, absolutely. So prior to starting York IE, I worked with my two partners at a company called Dine, which did the domain name system. So very deep technical infrastructure. And we really were sort of the go to market side of that business that we were able to grow to about 100 million annual recurring revenue and was acquired by Oracle. And as we reflected back on that growth journey. And we looked at all of the different sort of legacy institutions that we turned to help, whether that was our VC, whether that was our vendors, whether that was our advisors. We kind of felt like they were operating out of antiquated models that were beneficial to them, but not necessarily to us as the operators. And so we wanted to disrupt that. And so that was the genesis for launching York IE because, to your point, B2B software is very competitive, but it's also still at its infancy. And so I think there's a lot of opportunity for companies to, to continue to grow, but continue to grow. One of the things that we've always advocated for, which is I think because we're based in New Hampshire, is strategic efficient growth, not necessarily growth at all cost. 

03:14 Nice, nice.

03:15 That's a viewpoint we've been trying to bring to the market.

03:18 I think that's a good viewpoint to bring to the market. I think there's a lot of people that just grow to grow. And sometimes you're like, what are you doing playing in this part of the niche? You know what I mean? It's kind of goofy sometimes. 

03:33 Absolutely.

03:34 So, now you were very casual in saying that you reached 100 million in recurring annual revenue. That is no small feat. Congratulations, by the way. It's awesome.

03:43 No, thank you.

03:45 And for those of you listening who are trying to build a recurring monthly revenue model, there are a lot of things to consider in building, you know, that there's so many different facets of, of SAS and there's so many different ways to hit this Adam, when you're evaluating opportunities for your investment side or your advisory, what are some red flags you see? I mean, there's obviously things people do wrong and everyone thinks that everything goes right in SAS. What are some red flags that you see that you're like, yeah, this probably isn't gonna work for us?

04:16 I mean, I think one of the things that you see a lot of is sort of like a product out approach, right? Like a lot of times, like especially for new companies, you'll have some sort of a founder that's a subject matter expert in a field and they had a problem, so they solved it. So now they assume everybody else wants it as well too. And what we always advocate for is a market in approach, right? Which is like. Okay, great. Like that's awesome. You know your product, but how does your product play in the broader competitive landscape? Because successful companies have not just features for features sake, but they have features that people want and they are rising as the market is expanding. And I think taking that kind of approach as early as possible will help influence sort of everything that you build for your company.

05:07 So are you talking more about just really paying attention to what your competitors are doing or paying more attention to what your current subscribers are saying they want?

05:15 I think the combination of all of those things.

05:17 I think you're right too. I was wondering, I don't look at as many use cases as you do, so I'm really actually very curious about this because so many people out there, especially developers, are trying to create something that's gonna build that month of recurring. Everyone wants month of recurring or annual recurring. And so as you're looking at that and trying to build that, what are some of the big green lights? I mean, you probably look out on the landscape of the opportunities that you see and you're like, dude, I wish I had a piece of that one. Well, are there things and opportunities that you see that are really just like, you know they're going to work?

05:56 I think what I am and the company is really big into is at this moment, vertical SaaS that has horizontal applications. Because to our point about the pragmatic growth, the old Silicon Valley model is like a home run or I strike out. And I'm much more of a moneyball approach. Hey, can you manufacture a double? And then like, hey, if that's where you end up, like, you know, if you have a platform that, and you're kind of attacking, say, like the pest management space, and you become a really big player in the pest management space, that's a win. But then maybe you unlock some other verticals as well, and then you become that home run, but at the least you hit that double, right? And I think like one of the things to your thing about red flags is like founders have this vision, this grand vision, which is awesome. But like, what are the actual, yeah, what's the tangible steps to get there? Right? And that's what I like, that unlocking additional opportunity as you go along.

07:03 I like it. I like it. Now, now, Adam, one of the things that makes you unique in terms from an investment standpoint is that you do have this advisory side to you. You know, I think that a lot of people out there listening who are attempting to raise their, their initial seed rounds or maybe you're in an A or B round, a lot of people, they, they look for the wrong things. They don't really know what this, this investor is looking at when they're looking at their financials, looking at their numbers, looking at their product even. And you have the unique advantage of being able to come in and not only offer the funds that they need, but also the advisory piece. How important is it for people to be looking for strategic money as opposed to just any money to help fund their business?

07:49 Yeah, I mean, I think that's like going back to the to the point you made about like having just seen companies like raising a bunch of capital. It's like you have to understand that, you know what I mean? That is like you are selling a piece of your company when you raise money. And so just as just as you are so thoughtful in who you co-founded with and who you bring in as a leadership team, the same should be said about who you bring in as an investor, right? And not all money is created equal. And so you want to find a partner who's bringing some additional value and also viewing the opportunity in the same way that you do, because when there's misaligned expectations and misaligned incentives, it really takes the joy out of the startup journey, which is gonna be hard even on its best day. And like lose is sort of the whole point of it if it's just not a great experience.

08:40 Now, I know that in talking with a lot of other, different industries have different exit strategies, right? There's a lot of service providers who really don't see an exit until it's time to retire, and they just wanna exit to maybe family or pass it on through that kind of exit strategy, which is a strategy. But when it comes to SaaS, there tends to be this mindset of, all I gotta do is hit this revenue number, and then I should get this multiple. What else is there to it? Because a lot of guys, you know, they tend to think that they over-stimulate what their perceived valuation of the company is. How do you look at valuation? You know, a lot of these guys are just kind of bloated in their own heads. How do you read that?

09:28 Yeah, I mean, I think that like the last couple of years in tech have been a reckoning of that false valuations, as it turns out that like a 3 million revenue company is not worth, is not valued at $2 billion. It's surprising to everybody. But that's where, again, I think it's about, you know, I have always believed good companies have good options. And if you take that look at the beginning and you take that marketing approach and you have a full understanding of what kind of company you're trying to build. And then you go about build it in a responsible manner. You have a lot of options, right? My, my, my co-founder and my longtime friend, Kyle York, his most retweeted tweet is saying like, you know, in the tech industry, we have to celebrate a $25 million exit, uh, because that's still like for the founder. And the founder that owns. 

10:19 That was Game Changer.

10:20 Yeah, exactly. Right. But like in the tech crunch world and the, you know, the Sequoia world, like those are like scoffed at. You know, right. 

10:30 Really? I know. It's crazy. It's crazy.

10:32 And I think there's a lot more of a universe of potential opportunities for that than the, you know, $3 billion exits.

12:05 You know, which leads to another question. You know, there are not all founders created equal. I think you'd agree with me there. And as you think about founders in tech, some people are clearly very, very advanced and technical in terms of their ability to visualize a platform that can solve a lot of really cool problems. And then there's others that are just really good at being the face of the company and the visionary and kind of guiding it that way. As you look at both types of leaders in these SaaS companies, clearly there just are points where certain people are meant to exit sooner than others. Where do you see that difference in those two different personality types that we just talked about?

12:55 Yeah, it's interesting. And I think that realization that not every company and not every stage is right for every person is a very liberating thing, right? And that's where like, I love working with second time entrepreneurs because they kind of understand that a little bit. A first time entrepreneur, even myself as a first time co-founder, right? Like it's very easy to fall into the, oh, I must be doing something wrong because this part of what used to be my kingdom is now moving to somebody else. And the reality is you've actually done something right, right? Like a lot of times in those early days, like, um, you have kind of two jobs because there's not enough, you know, and then it's like, well, if you've done your job, yeah, right. 

13:37 Two or ten.

13:38 Yeah. Exactly. Right. Um, and so, you know what I mean? I, and I think that like, you know, I talked with a performance coach once and she said, you know, most companies fail not because of external factors, but because of internal factors. 

13:58 Agreed.

13:59 Right? And I think just having that self-awareness can be the difference for different founders on the different stops on their journey.

14:02 Love it, love it. Now let's take a step back. Now that we know kind of who you're trying to help, how you help them, the problems you're trying to solve, let's talk a little bit about your business. I mean, you guys have been doing this now for how long?

14:16 So we founded the company in September of 2019. So we're going on four years.

14:23 Okay, oh, just right before, right as people are starting to get that cold, right?

14:28 It was very, yeah, we thought, and it's funny that you say that because we thought like, okay, we wanted to have this sort of hands-on investment approach. So we thought we would be very biased to the Northeast being in New Hampshire. And then, then the world shut down. And it didn't matter if you were in the town next to me or if you were in Utah, which really, really expanded our model and opportunity because I truly believe there are great entrepreneurs everywhere. And I really do think that we are entering into the sort of phase where the Silicon Valleys of the world and the Austin's and the New York's, that they aren't gonna have that stranglehold. 

15:06 I agree with you.

15:17 Yeah. And smart, yeah, and it's smart. And that's a fun opportunity to try to go and look and find those founders doing cool things.

15:15 I love it. I love it. You know, I agree with you in a lot of ways and I'm glad that you had a positive effect from COVID because it did really, really launch people out of their own comfort zones in a lot of ways. And so as you started to like, you know, build this model, which came first, the advisory or the investment? But what kind of led, which came first in your little puzzle there?

15:39 The investment side came first because as it turns out it's easier to give money than to ask for. And then what we did was we kind of piloted that hands-on execution with the companies that we were investing in and then we found that there was real product market fit and there was that real need at that sort of C, early C, A, and then we were able to then go and say, okay great, now let's go take that to more companies and then as a result, that's continued to grow and begin.

16:13 But you knew from the start that companies you wanted to invest in, you wanted to help guide and coach. Is that right? You wanted to strategically kind of align with companies that you knew how to expand and grow.

16:25  Yeah, to your point about what kind of capital did we want to be, right? Like, I think a lot of traditional VC are more money managers who think that companies are built in spreadsheets. Whereas I think we realized that companies are built by human beings. And we wanted to really get involved with those human beings and help them, you know, chase their dreams.

16:47 I love that you say that because I am a self-proclaimed master at playing spreadsheet billionaire. And it does definitely take a real executioner though to really take the model and put it into action. And I think to your point, it's a beautiful thing that you're doing. You're really kind of helping them understand the spreadsheet that they've put together to pitch you with and now say, okay, to really execute on this, you don't just need the money. You need X, Y, and Z also. How do you fulfill that with these guys?

17:22 Yeah, so we've built a very large, like a very strong team. So across those four services that I talked about, we have over about 120 employees. And I always joke with my co-founders that we had to start the company because right now we're not even qualified for an internship because we've been able to attract such talented folks. Because I think they believe in our vision of really helping reshape the way startups are built, scaled, and built.

17:53 I love it, I love it. And as you jump in, after investments have been made and you really jump into more of the advisory and plugging people in, what does that look like? Are you replacing people, are you just supplementing? Like, are you coaching training? What are the typical problems you're seeing on initial early stage guys?

18:11 Yeah, yeah, absolutely. And just to clarify the point too, like we're doing these advisory services for both the companies that we invest in and just companies in general. And what we're seeing is like a lot of companies will come to us with a point solution, like, hey, we just had the seed funding, we wanna do an announcement and we wanna start building our brand. And in that case, we'll come in, we have like basically like your Swiss army knife of a marketing team, we can either directly work with the co-founder or potentially maybe you have a more junior marketing resource that you want to supplement. And so those are the problems we're seeing. Hey, we got some funding. We need to accelerate the product. We need some dev help. Hey, we have the product. We wanna go and build a brand and tell a story. Or hey, we have some traction now, but is our sales process as clean as it could be? We're not really even, we're not a spreadsheet, not a CRM, and we come in and help them in all those different areas.

19:10 I love it. What a fun stage. And you're really attracting, I think, the types of people listening to this podcast. And so for those of you listening, I hope you're really listening carefully because a lot of you are at that stage where you're launching or launched, and now that you've launched, you kind of look around and say, okay, we're making money, we've got revenue coming in, we've got great team, what do we do next? And so I love people like you who can actually jump in and say, Here's the strategy, here's what needs to happen next, but let's evaluate where you're at right now. That kind of where you're at in a lot of ways.

19:46 Yeah, absolutely. And that's where we'd have like a lot of times we would start with like a kind of like a corporate strategy deep dive project that we work with companies. Look at the financial model, we look at this, you know, the tech stack, we look at website architecture and we just come in and help make suggestions about, you know, you push these levers and start running.

20:06 I love it. You know, this is such a great conversation to have. And as you do this, and as you've been able to grow to these hundred and whatever plus employees and this team that you're building, where do you anticipate taking it? I mean, what's your strategy? Do you have an exit plan? Or is this kind of a forever grow and scale game that you're playing?

20:25  Yeah, I mean, like, you know, I always say that I started working at York IE in kindergarten, because that's when I met my partner, Cloud York, for the first time. And so we really do want to, yeah, we want to build something of, of substance and in scale. And so I think two areas that we're doing that is like, we're continuing on our full service business. But one of the things that we realized was that companies even earlier in the journey, right at that ideation stage, they have all the same problems but they have even less resources to solve them. And so we're really trying to productize our full service into sort of a strategic growth platform that earlier stage entrepreneurs can self-service themselves on and get real value. And you might see, I have like a little stat up here that says 80% of startups fail. And I believe that a lot of that is at those earliest days where they just don't, to our point about, hey, these companies are growing everywhere they may not have access to some of that strategic advice. They might not have access to some of those resources. So if we can figure out a way to get them some of that stuff even earlier, maybe that number goes down to 75% or 70%. And then you're talking about millions of people that are being able to fulfill their dreams, which to us is a really exciting problem to tackle.

21:40 I love it. Love it. Yeah, there's definitely no shortage of people that need the things you're giving.

21:45 Yes, right. And that's it. Like, how do we reach as many as we can? Because that's really like, you know, we want to have that impact.

21:51 I get it. I love the passion and I love the mission. That's very, very aligned with what I'm doing. So I'm grateful, so grateful to have you on the show because I think we're both reaching the same target audience with very similar solutions. And I think we can do nothing but continue to add value to them to hopefully turn that into a 70, 30, 60, 40 number to get people out of failure.

22:13 Exactly. And because I write, you agree, these are like, you know, people that are willing to be brave and start a company, you know, that's, those are the best kind of people in any way that we can help them. I'm all for it.

22:26 I love it, love it. All right, so challenges. The big problems, you know, challenges within your own company, and then challenges within the companies you work with. Let's start with your own company. As you started to build and grow this model, it doesn't sound like, to me, a very easy prospect of saying, okay, shoot, these guys need a CMO, and these guys need a CMO, and we've only got three of them. How do we spread these guys out? Like, how did you grow and build the process that's gonna adapt your team to fit all the challenges that these new investments are bringing to you?

23:01 Yeah, no, I think that like, I think one of the biggest problems for us in the earlier stage was like we wanted to be helpful in everything. And then one, that becomes like a very complicated thing to try to articulate to people. And then two, that's a very hard thing to kind of make repeatable and scalable. And so I think we also had to be a little bit more disciplined in our offering and sort of say, hey, these are the four things that we're going to be really good at. Then we're going to try to build a nice partner network for when things come in that we're not good at and say, hey, we recommend these people to do that, right? And it's like, and it's anybody when you're chasing, you know, and we've tried to do this company very, like we bootstrapped, which also means that like, we had to try to get everything right on the first time, which is really hard to do, 

23:56 Yeah. It is, it is. Or at least partially not right and change it really fast, right?

24:02 Yeah, absolutely. Right. And that's the thing I think like, for anybody listening, that's chasing revenue because they need it to be sustainable. It's like sometimes, you know, and you got to learn it from doing it. But like, sometimes you bend yourself into a pretzel to get the revenue and then it would have been much more valuable. 

24:19 Faster just to get clients.

24:22 Yeah, yeah, just well just to get Yeah, like, you know, it's like, if you spend so much and this is true, if whether it's a service or whether it's a product, like, if you're gonna you're gonna fall victim to spending so much time trying to fix a bad customer, then would be much better served realizing that that's not a fit, being okay with it, and putting that emphasis towards finding two or three new good customers.

24:46 Love it, I love it, and so true. Spoken like a true bootstrapper too. You know, it is very much, I mean really, there's not many of us that like to bootstrap, and I'm finding that to be more and more true as I hear a lot of early stage founders thinking, okay, I've got a good idea, let me go raise some money. Instead of, hey, I've already onboarded a handful of clients, it seems to be working, I just need some operational money, right?

25:16 Well, one of the things that we're seeing a little bit more of Todd, where we've been helpful is like taking successful services companies to your point, which are relatively investment light to get off the ground and then having them get some traction. And then from there, productizing an element of the business either to A, make their margins higher on the services side or B, have a product that they can then offer at a higher margin from more of a SaaS perspective. And I think that's a really compelling approach for more entrepreneurs to start doing.

25:50 I love it. Adam, this has been such a fun conversation and you're the type of guy that I think we could probably have another hour and a half, really fun conversations, talking back and forth about this stuff because we're both passionate about this. And for those of you listening, I highly recommend you go check out what Adam's got built. He's got a really amazing platform in helping people like you bridge that gap between, hey, I just launched and what do I do next? And do I need to raise money or should I just try and keep going on this path? And I think that if you're in those questionable moments, go check out what Adam's doing. I mean, really, it's a very, very cool site, very easy to navigate. And Adam, before I let you go, I always love to get a shout out for somebody who's inspired you to do what you're doing. I mean, this is not an easy business. You're high risk, you know, business model. How are you doing it and who inspired you to get into this?

26:46 Yeah, I would say like, if I'm going to give a shout out, I'll give a shout out to my dad. As a father myself, that's always good to get the shout out. And I would say like, he always said, like, find what you're passionate about, and the money will follow. Right. And like, I have always been passionate about storytelling. And like, when I was a kid, I thought I was going to be Ernest Hemingway. Turns out that I can't drink very well. But then I took that. So then I started telling stories as a journalist. And then I realized, like, I could tell corporate stories and businesses stories, right? And that has led to some of the more financial success. But at the core, I'm still doing what I love, which means I feel like I haven't really worked a day in my life.

27:30 I love it, love it. Adam, thank you. Thank you for spending time with us today and sharing these insights with our audience. And I truly hope that some people look you up and connect with you because this really is a value, huge value you're adding to the world. And SaaS companies, you know, it's not as easy as it looks sometimes. In your corner, who is advising, coaching, mentoring, possibly investing, getting you to where you need to go without all the scrapes and scratches that people like Adam have seen. So I highly advise you check him out. Adam, thanks again for being here and the rest of you, we'll catch you on the next episode. Thanks Adam.

28:09 Thanks, Todd.