Maker Manager Money - Entrepreneur & Business Owner Inspiration
Hello there. Welcome to the Maker Manager Money podcast with Kyle Ariel Knowles. This podcast is about entrepreneurs, solopreneurs, founders, business owners, and business partnerships, from startups to stayups, to inspire entrepreneurs to keep going and future entrepreneurs to just start.
Maker Manager Money - Entrepreneur & Business Owner Inspiration
Building Value in Startups: Adam Coughlin and the Unique Approach of York IE
In this Maker Manager Money episode, host Kyle Ariel Knowles welcomes Adam Coughlin, co-founder and Chief Marketing Officer of York IE, an innovative advisory and venture capital firm focused on helping early-stage B2B SaaS companies grow.
KEY TAKEAWAYS
The Power of Storytelling in Startups: Adam emphasized the importance of storytelling in the startup landscape. A founder's journey begins with selling a vision and an idea. Data points can validate that story as time progresses, but the initial narrative attracts people to your mission. This highlights the need for entrepreneurs to craft compelling narratives that resonate with their audience and stakeholders.
Responsible Fundraising and Pragmatic Growth: In today's evolving market, Adam shared that the approach to fundraising has shifted. Gone are the days of "growth at all costs." Instead, founders should focus on understanding their "why" and ensuring they build a sustainable business. Responsible fundraising means being mindful of the equity you give away and ensuring your growth strategy is grounded in reality. The "Rule of 40" is a great framework to consider, balancing growth and profitability to create a healthy company.
Leveraging AI as a Tool for Success: The conversation also touched on the increasing role of AI in startups. Adam pointed out that AI should be viewed as a powerful tool to help founders do more with less. However, it's crucial to have a strong strategy in place before diving into AI solutions. Founders should focus on understanding their market and crafting a unique value proposition before leveraging AI for marketing and operational efficiencies.
Explore Adam's journey from journalist to tech marketer and entrepreneur. He shares invaluable insights on the startup ecosystem, the importance of storytelling, and the challenges of transitioning from a corporate environment to the founder's seat.
We dive deep into essential topics such as:
- Responsible fundraising and pragmatic growth strategies
- The significance of understanding your "why" as an entrepreneur
- The increasing role of AI in startups and business transformation
- The unique all-in-one approach of York IE that aligns founders, investors, and their teams
Adam's passion for inspiring entrepreneurs shines through as he discusses the value of building strong relationships and creating a supportive startup environment. Whether you're an aspiring entrepreneur or a seasoned founder, this episode is packed with actionable advice and thought-provoking perspectives.
Don't miss this engaging conversation, which encourages you to keep going, start your journey, and embrace the entrepreneurial spirit!
LINKS
- Follow Adam on LinkedIn
- York IE - Advisory and Investment Firm for Technology Companies
- The Third Door: The Mindset of Success by Alex Banayan
- Follow Kyle on LinkedIn
Adam Coughlin: Hello there, welcome to the Maker Manager Money podcast, a podcast to inspire entrepreneurs to keep going and wantrepreneurs to just start. My name is Kyle Ariel Knowles and today's guest is Adam Coughlin. Adam is co-founder, chief marketing officer and managing partner at York IE. York IE is an advisory and venture capital firm that helps technology companies grow by investing in and providing services to early stage B2B SaaS companies. York IE utilizes a unique all-in-one approach to align founders, investors, and their teams. Adam leads the company's go-to-market efforts and works with startups in marketing communications, digital marketing, and revenue operations. In our conversation today, we'll delve into essential topics such as responsible fundraising and pragmatic growth, providing a supportive environment for entrepreneurs, and the increasing role of AI in startups and business transformation. Adam is passionate about inspiring entrepreneurs, and I'm thrilled to have him join us. Welcome to the show, Adam.
Adam Coughlin: Thank you very much for having me, Kyle.
Kyle Ariel Knowles: All right, where are you dialing in from today?
Adam Coughlin: In subtropical, rainy Manchester, New Hampshire.
Kyle Ariel Knowles: Okay. We've had rain here in Utah as well. You know, looking at your profile on LinkedIn and doing some research on York IE, I guess my first question for you, based on your career journey from Oracle to co-founding York IE, what key lessons did you learn about the startup ecosystem?
Adam Coughlin: Yeah, that's a great question. And I would say, like, even if you go further back into my career, I actually started as a reporter. So I was a journalist, I worked in here in the US, I lived in Beijing, I lived in Italy, I lived all over the place. And I think one of the best lessons that I've learned that has transcended whatever those different stops on my career is the power of storytelling. And that's how we learn, that's how we remember things, that's how we process information. And I think that's particularly important in the startup landscape, because at the beginning of a founder's journey, really what they're trying to sell is a story, an idea. And then as time progresses, they begin to get some data points that actually prove that that story is correct. Uh, but at those early days, you really just kind of, uh, spinning a vision and spinning a tail and seeing if you can get people to kind of line up behind it and head in that direction. And, uh, that's been a lot of fun in my career to sort of, uh, have different stops where I was telling different types of stories along the way.
Kyle Ariel Knowles: Okay. And you were always in marketing and all the roles you were in before you even joined a startup?
Adam Coughlin: Absolutely. Well, yeah. So like I started the career as a journalist, right. And that's like. communicating, writing, understanding, you know, what is going to motivate people to continue to read your story. So that was a very natural transition from that into tech marketing. And that's where I started at a company called Dyne and built out sort of the marketing communications function at that company, which then got acquired by Oracle, which then led us to kind of reflect on that growth journey at Dyne and felt like a lot of sort of the legacy institutions that we were turning to for help were antiquated. And that's what we wanted to disrupt when we launched York IE in 2019.
Kyle Ariel Knowles: And how did you meet your co-founder then?
Adam Coughlin: We go way back. So Kyle York, who is the namesake of our company, was my friend in kindergarten. And then one of my other co-founders I met much later in life at Little League, Joe Raska. And so Kyle, Joe, and I were actually on the same Little League team. We really enjoyed working together, but weren't very good at baseball. So he said, we got to develop some other skills. We kind of all went out and did complimentary things. And then we reunited at Dine. That's where we met our final co-founder, Mike Vailleux, who worked with us there. And then that team, plus our CFO, Janelle, who worked with us at Dine. Having all worked together, had been through the grind and were successful. left that and started York IE together. And I think that's really nice. It's nice to work with your friends, but it's also nice to have a track record of some success as well too.
Kyle Ariel Knowles: Yeah, your previous success at other companies and you know what each other's strengths and weaknesses are.
Adam Coughlin: Yeah, and I think you know as well as all of your listeners do that the startup journey is not for the faint of heart. It's difficult and you're gonna stretch yourself sort of beyond the capacity that you think you're capable of and you're gonna have to run through some walls. And I think when you genuinely care about the people that you are working with and don't want to fail, not only for yourself, but for them as much, it can have you go that extra, the distance. And I think that can really be a positive impact in those early kind of chaotic days.
Kyle Ariel Knowles: For sure. And what are some of the key differences that you found working in a corporate situation like Oracle and then going to startup and startup mode? What are some of the key differences?
Adam Coughlin: Yeah, I think I realized how cushy my marketing seat was at Dyn and then Oracle, right? Like you're very responsible for your own sort of little silo. When you sit in the founder seat, you are responsible for everything. Right. And I think the learning curve for that is, uh, uh, really intense. Um, and I think that that's why, like, you know, I often talk to, to, to people, you mentioned the, the entrepreneurs and the people that are, you know, sitting and thinking about what to do next. And, you know, I think that like, Knowing why you want to start a company is really important, because you can't really lie to yourself when it becomes difficult. And if your general purpose is to make a lot of money, there's a lot of easier ways to make money. But I think if your purpose is, well, I only get one shot at life. I want to have a rich experience where I'm challenged, and I learn from that, and I develop all sorts of different skill sets from the technical to the soft skill sets. The founder's chair is the best place, I think, to sit to do that. And you really can't replicate it in, you know, that larger sort of corporate environment because so many of those things have already been figured out and you are more into the management phase versus the building phase, right? And those are different skill sets. You know, personally, I gravitate toward now having experienced both of them. I really feel a lot of meaning and value in the building.
Kyle Ariel Knowles: What was cushy about your job before becoming a founder?
Adam Coughlin: Well, I don't necessarily, I just think it's like the limit of the purview, right? Like you are not, you are responsible for like sort of your thing that you have developed a subject matter expertise over years. And I obviously wasn't to like on the executive team of Oracle. And so there's always people sort of layered above you in the founder chair, right? Like the, the old saying, the buck stops with you. You know what I mean? Like that. I feel like that responsibility is much heavier. Additionally, when you are in a larger corporate environment, you have a lot of resources. At your disposable disposal, which don't necessarily exist in the startup world. Right? Like, I, I've seen that particularly on the sale side of it. I've seen like, uh, sales leaders that were very effective in larger organizations think like, oh, I, I could be the VP of sales at a startup. And then they realize that, like, and this is actually where the, um. Kind of learnings of my early days as a community journalist are really interesting, like not that hard to get an interview when you are the New York Times. easier to get a sales call when you call up and you tell them you're from Oracle. You got to be much more creative when you're from a newspaper that nobody's ever heard about or from a company that has no brand equity, right? And sometimes people go from that environment and realize that maybe it was the name on the front of the jersey that was doing a lot of the work and not necessarily the name on the back of the jersey and they struggle with that sort of transition.
Kyle Ariel Knowles: that makes a lot of sense. And, you know, when you're in startup mode, you don't have a big budget. You don't have a fully formed staff and department and all those kinds of things as well.
Adam Coughlin: Yeah. And a lot of times you like part of growing in your career is that you outgrow some of those jobs, which is good. And you get into more of the strategy and the leadership and the management and everything like that. And then when you go into the startup, you go right back to square one and like, you know, I was literally like writing every single blog post for York IE, as opposed to having a team of writers do those things. And then if you're successful and you build the team and everything like that, you begin to bring in other people that can take over some of those functions. But it's certainly a grind to get there. And, you know, and I think some people think they want to do that and then other people, you know, understand what it takes to do it.
Kyle Ariel Knowles: maybe not as glamorous as it seems.
Adam Coughlin: Yeah, right. It's definitely not as glamorous as it seems on the day to day. But then, you know, so much of life is like sort of when you zoom out and look back at those, you know, three, six, nine, 12, two year months. And then you say, wow, look at all that's been accomplished. And, you know, I mean, there's a lot of value and excitement when you get that perspective.
Kyle Ariel Knowles: I had another question you had mentioned. It's important to understand the why you want to go into entrepreneurship and why you want to be a startup founder. What was the reason why you wanted to do that?
Adam Coughlin: I think that like, I think the, you know, it's like, uh, the initial why was sort of like, Hey, I have been part of a very interesting, exciting startup journey as sort of an ancillary player. I feel like I've learned a lot through that experience, that being kind of my ride at Dine into the acquisition of Oracle. And now it's like, I think that I've learned a lot from that. And now I want to see if I have the capacity and the skills to do that from the lead. Right. And then I think that was sort of the genesis. I think there's like, you know, the old comedian, Dane Cook said, if I had realized how hard it was going to be to be a successful comedian, I probably never would have started. And so I think it's good to have a little naivete at the beginning. But now I think it's like what I, my why is sort of like, I really love creating value. and providing value to different people. And for us, that's really exciting because we have so many different constituents, right? Like we have on our services side, the value that we're providing to the founders and operators that we're working with. On the investment side, there's the value that we're providing to our investment partners and all of those different things. And I'm just really excited by if you build value, then all of these good outcomes will come from it. But it's really hard to build something valuable that people want. And that challenge, I think, is really inspiring to me.
Kyle Ariel Knowles: So explain to the audience what kind of value you create as a company then.
Adam Coughlin: Yeah, absolutely. So as you alluded to in your introduction, we're trying to help technology companies grow, right? And so we do that through sort of two avenues of our business. So on the one side is we have an investment practice. So we are a seed stage, early stage investor in, as you mentioned, exclusively kind of B2B software companies right now. The thought there was the sort of historical venture model was feast or famine, right? It was like one of my companies in my portfolio is going to be a decacorn and that it's gonna pay for everything. And even if the other nine out of 10 fail, I still return value to my investors, right? Maybe it's because we are in New Hampshire, we felt like, that doesn't seem like really good math. And like, when you think about, hey, these companies are being founded by people, you know, we would like those people to be more successful than having nine out of 10 of them fail. There must be like a way to look at this model in a way that allows more people to be successful. And so that's how we kind of approached the investment practice that we started. And now five years in, we have a very happy to report that we have a 90% survival rate so far. So most of the companies that we've invested in over the years are still going. and working and 60% of them have gone on to raise a up round after our investment, right? So I think a lot of those companies are doing well. And I think that's a good way to sort of add value and kind of flip that model on its head and provide value to those companies. Now, one of the ways that we've been doing that is that we realized that companies of all stages need help. Many investment firms and partners and advisors, they're providing a lot of strategic help, which is great and very important. But at the end of the day, people need stuff taken off their plate. And so that's why we built our advisory as a service kind of practice to be executional help, cross-functional. So we are helping companies with everything from product development to go to market, building their website, implementing their CRM, to the GNA functions of accounting and bookkeeping, right? And like allowing these smaller teams to get some uplift and execute against the strategy that everybody collectively has worked on, right? And then I would say those are like really tangible things. And then like, because so much of our reputation is built off of the ecosystem and our relationships that we just want to add value in doing things like, You know, we do different round tables in different cities where we bring together a bunch of CTOs and, and allow them to have a community where they can talk about some of the different challenges that they are dealing with. We, we try to do virtual workshops with our portfolio companies or our clients, where we bring in expert speakers to talk about, these are the latest trends that we're seeing in hiring, or these are the tech stacks that we're seeing successful companies on using on GTM and, you know, I just feel like if you provide value to people outside of the black and white scopes of any relationship that you have with them, that's going to be good in the long term. And that's kind of one of has always been one of our models, which is play the long game. And that just tends to, I think, you know, again, like, if you can do that in the short term, I feel like the long term takes care of itself.
Kyle Ariel Knowles: And so were you an investment firm first or a services firm first, or did you come out swinging and offer services and investment at the same time?
Adam Coughlin: Yeah, I think we, we came out swinging and felt that the, the uniqueness of that joint combination was going to separate us. Right. And, you know, you kind of see that like, you know, over the last few years, sort of, um, capital has become commoditized and people really want that value add. So like, how are you, you know, how are you doing capital plus something else? And I think that the whole part around the execution played towards that, which you had mentioned earlier, sort of our philosophy on the pragmatic growth and that maybe a company that has 3 million of revenue isn't worth three billion dollars and that like that actually isn't the necessarily the best strategy for the founder and that like if you build a good, strong, healthy company, you're going to give yourself options. And then if you have options, you're, you know what I mean? Have a lot of, um, kind of power in the situation, which is, which is really good. And I feel like the more options that an entrepreneur has, the better outcomes for everybody that's involved.
Kyle Ariel Knowles: Yeah. And it looks like you're, I mean, you have a really good chance of having ROI because you're investing in a company and then sort of paying yourself back in services. So there's a little bit of ROI there, but you're also making sure that the company is successful in it with a 95% survival rate. That's a really good survival rate for an investment company.
Adam Coughlin: Yes. And, and, and, uh, I don't want to over embellish 90%, but yes. Uh, and, uh, and yes. And to that point, it's like, you know, we came out doing both because we didn't want to just be passive investors that only got a quarterly update. We wanted to roll up our sleeve and really get involved. And, um, the people, the, the, the firm, the companies that we work with on the investment side really appreciated that. Like. Yeah, we can come in and add those services and be helpful knowing that we're actually incentivized by their long-term success. We're not trying to squeeze every dollar out of them on a services perspective. And to our investment partners, it does de-risk the situation a little bit because it's like we are intimately involved working collaboratively. And then what's interesting is that the flip side of that is that you are gravitating toward the investment to services. The other way that the situation can emerge is that we work with companies on the services side, get to know them, enjoy working with them, and then the opportunity exists where we then invest in them. Right. So it works in both ways because we do services and investments. Oftentimes they overlap, but we can also operate them both exclusively too.
Kyle Ariel Knowles: And so as far as investments go, what percentage of the companies that you're working with, do you invest in first? And what percentage of the companies that you work with, do you do services for first and then invest later?
Adam Coughlin: You know, on the investment side, we have the strict constraints of capital, right? We do 10 to 15 deals a year. I would say the majority of those companies over time leverages our service in some way to be helpful to them. We don't have the constraints on the services side, so we add a lot more services clients. We have become really good at delivering value and help to the companies. And so on the services side, we range from Pre revenue. So we're working with companies prior to even like our investment stage and then we're working with companies all the way up to 200 and million in revenue. So way past our investment stage. So we have, you know what I mean? Like. onboarding a lot of new services clients. Some percentage of them hopefully we will invest with, but a good percentage we never will because they just are either not in the right stage on the services side. We're not constrained by needing to be B2B. We can do product development for B2C companies and different things like that. So, you know, and one thing that we're also seeing from a flywheel perspective is On the investment side, we have all these portfolio companies. It behooves us to have relationships with later stage investment firms, whether that be later stage venture, growth equity, private equity. In getting to know them, they all have portfolios of companies who need help. on the services side as well. And we've begun to start doing, you know, they say, Ooh, look at these York IE companies who have been helped with their services. They're really seem mature. Could you help us with some of the other portfolio companies as well too? So it's a very interesting kind of model that we've created. And I think to my point about being naive, I think coming out, swinging and doing all of those things at once was really hard, but it also helped build a very kind of broad foundation that we're now able to build off. you know, really build a unique sort of firm.
Kyle Ariel Knowles: Yeah, and what's interesting about the model and why I say, you know, come out swinging, because you're basically taking money and investing it and reaping the rewards of future clients on the services side from that investment. And so over time, you know, services leads to investments and investments leads to services. So you kind of have this built in, I don't know, lead magnet going on throughout the whole, everything that you do at York.
Adam Coughlin: Yeah. And I think that's like, again, like to our point of like, can you figure out how to add value in different ways? And if you can do that, then you have different levers that you can pull.
Kyle Ariel Knowles: Right. And so do you feel like it's a, a good time to be a startup founder in tech right now, or is it a difficult time to be a startup founder?
Adam Coughlin: I think it's a, it's a good time. I think that like, you know, I think there's a lot of different, ways of which I think there's like, I think that there was a period of time where there seemed to be a playbook, right? And it was like, go, you know, get your idea, go raise money, spend that money, raise more money, spend more money. And like, it was like you either became, you know what I mean, a unicorn or you didn't. And now I think that there are a lot of different sort of paths Uh, that entrepreneurs can tape I think, like, right? Like, there's like, obviously, there's always been the historical bootstrapping approach a term we're seeing, uh, out in the market more now is seed strapping. where you're building some sort of a software, some sort of a product, you need some additional capital to do that, but you're doing that with the intention of using that to get to a state of profitability of which then you can kind of decide what you want to do. There's obviously still the traditional sort of venture. Now you're seeing private equity and growth equity moving down market. I think that there's a lot of different ways that a founder can build their company. And then I think which you touched upon early, there's a lot of new tools and technologies that are allowing you to kind of lower even the barriers of entry into building, right? Here's a funny anecdote. Like when we started the company in 2019, we thought we were going to replicate the formula that we kind of had done previously in our career, which was like, be the go-to market extension of a deeply technical founder. because from 2008 until 2020, the only tech companies that were being built were founded by computer scientists, engineers, deeply technical CTOs. Fast forward to 2025, and there's been so much advancements in, or just even like, I mean, open source, AI, the access to remote talent, the access to offshore talent, that actually we're seeing a big trend of GTM founders who know how to bring something to market and sell it. And then we're actually oftentimes being the technical execution of them. So it's almost flipped the model a little bit. And so to your first question, I think, There's like a lot of different archetypes of founders now. And so I think it's, it's, it's very ripe for, for somebody who maybe even 10 years ago said, Oh, I don't have the skillset to do that. Uh, there's new opportunities presenting themselves.
Kyle Ariel Knowles: And so with, um, chat GPT, you know, released to the public two and a half years ago now, it'll be three years in November. If you look back two and a half years ago at, you know, I don't know if you were doing 10 to 15 deals a year, but think about those deals two and a half years ago. And then think about just last year, the deals that you did, how many of those 10 to 15 companies. Are, would you classify as like AI specific? They're doing something specifically with AI as a service.
Adam Coughlin: Yeah, I would say that I, that has probably exploded. I think every company that's new now has AI as some component of it. I think the reality is, is that our investment team on the other end of it has to do a lot of due diligence because it's always, you know, is it buzzwords or is it actually, you know, proprietary and value add and interesting. We've always been from an investment perspective, interested in sort of the vertical software. And so now we're seeing a lot of interest related to like the vertical AI, right? Like I think to your point, the sort of horizontal long, large language models of the open AIs and the Geminis and the Anthropics, like They're pretty good, where there's a lot of opportunities in that sort of small language model. You have some very unique vertical-specific, industry-specific data that you're baking into sort of the platform, et cetera, that could be really valuable to a certain level of audience. And maybe those companies don't grow to the size of OpenAI. Uh, but that goes back to our sort of like, uh, pragmatic responsible fundraising, the way that you're building it still huge opportunities to be, you know, life changing, uh, wealth creation.
Kyle Ariel Knowles: Right. And speaking of responsible fundraising and pragmatic growth, for an entrepreneur currently fundraising, what does this look like in practice? Like, can you give us an outline of what responsible fundraising and pragmatic growth looks like for?
Adam Coughlin: Yeah, well, I think it's just like, like, you know, three or four years ago, right? Like there was just sort of like a frothy frenzy where people could go out and raise money. I think I remember reading an anecdote about like an ice cream truck that got 2 million in funding, like just like completely illogical, like doesn't make sense, right? And now, you know, like the goalposts has sort of shifted from all of the different milestones at the different stages and like you need to show more traction. So I think that part has gotten more difficult for founders. But I think that also allows them to be further along in knowing what works when they actually take in money, which is going to make that money work much harder for them than just throwing at it and trying to hope what it accomplishes. And then the further sort of along that you've gotten and developed some of those traction and customer-funded milestones allows you, again, to have a little bit more of that flexibility and decide, OK, what do I actually need the fundraising for and how do I want to do it? And I think along the way somewhere, it became a little bit forgotten that when you went out and fundraised, you were selling a piece of your company. And I think it's like, I know a lot of entrepreneurs started because they are free spirited like to be in charge like want to build something and then like, you know, if you if you kind of go down that fundraising hamster wheel suddenly you wake up one day and you realize like, oh, like. the reason that I started this and all of the things that I wanted are not necessarily there anymore. And I think that that's slow and steady. And again, that's not to say there are certain technologies and spaces and stuff like that where you have to go for it. You've got to raise a ton. You've got to go be first to market. It's a land grab. It's all of those different things. But it's just like, that's not the only approach. And I think that there's a more universal acceptance and there's more investors that understand that there's different sort of options. And then it's the, you know, the fundraising is a two-way street and it's making sure that like you as the founder have a partner that is viewing this thing the same direction in the same way that you are too, right? It's when those things get misaligned that some of the difficulties happen.
Kyle Ariel Knowles: Right. And so what is your definition of pragmatic growth and what does that look like for a startup?
Adam Coughlin: Yeah, so I think there used to be this approach of triple, triple, double, double. It's like you triple revenue, then you triple revenue, then you triple revenue, then you double revenue, then you double revenue, all of that. And now you're seeing a lot of companies that are trying to be more like the rule of 40, which is some combination of growth and profit. Right, so it could be 40% growth and no profit. It could be 10% growth and 30%, like those sort of like that sort of guardrails, I think, begin to show you that like, that you are a healthy company. You know, I think there's a real attraction to healthy companies.
Kyle Ariel Knowles: So more focus on profit than simply growth.
Adam Coughlin: I think there was a time where it was growth at all costs. I can't light money fast enough on fire to get those outrageous growth milestones, even if that growth is built on a little bit of a foundation of a house of cards. And I think we've seen those companies then struggle to uh, fulfill some of those valuations and some of those growth expectations in the long run. Um, whereas, you know, that, that rule of 40 approach is like still aggressive, but aggressive in a way where like, you know, maybe there is some bricks that have been put down and you feel a little bit more confident in, in the foundation that's been built.
Kyle Ariel Knowles: OK, we talked about a little bit the increasing role of AI in startups. How should early stage companies think about leveraging AI effectively and maybe explain again what vertical AI is as a key area for future success?
Adam Coughlin: Yeah, so vertical AI would be more of like the the industry that we're thinking about investing in, like cybersecurity, DevOps, like vertical AI, or sort of like this segment of companies related to the actual founder's use of AI. I think at the end of the day, AI is an excellent tool. I think that it's an excellent tool that can allow a founder to do more with less. I think the important part about AI is that It's a reminder to the founder that they really need to have a strong strategy. And that's why when we work with companies, we sort of start every engagement with a messaging hierarchy. What's your vision? What's the thing that, in 10 years, the world is different because you were successful? Then what's your mission? What are you working on every day to make that vision a reality? And then you work your way down into your elevator pitch and your differentiators. value prop, your kind of product marketing. And then in that, you know, the reason that we do that exercise is like, it's really important for founders to take a market in approach to company building. What happens a lot of times is that founders take a product out approach. I had a problem I solved it. Now I assume everybody else will want it. But the reality, though, is that no company is operating in a vacuum, right? You are part of an ever-changing, evolving ecosystem, the market itself, competitive landscape. And so kind of taking that marketing approach allows you to sort of say, hey, I've surveyed the market. I understand what the competitors are offering. I understand the trend, the direction that the hockey puck is going in the market, and I'm going to provide a unique perspective and point of view that will lead people to that. And then I think once you've developed that point of view, you understand where the green space is for your company, then great. Then you can leverage some of the tools to help you with marketing and sales collateral and getting those things out there. But they should be distribution of the message and the strategy that you've been built. Sometimes people go right to tools and right to distribution. And now one of their problems is they're just saying stuff, but they're not actually building on anything and being
Kyle Ariel Knowles: Yeah, that makes sense. So what specific AI tools and workflows have you adopted?
Adam Coughlin: So we use a lot of it on sort of like me being our chief marketing officer and thinking about our own practice of building our brand and different things like that. Right. So I use a lot of the sort of generative AI tools for creating social posts and repurposing pieces of content. Right. I like to kind of put a lot of effort manually into some sort of an anchor asset, whether that be a webinar, whether that be a really, you know, thought leadership posts, etc. But then I find that the AI tools can be really good to sort of take that anchor and repurpose it through some of the different channels because, you know, people consume information in so many different ways. You kind of have to be sure that you can hit them in those different places. But if you don't do it from the anchor and you end up doing it like completely different in each of those places, then like all you've done is introduced a fragmented version of yourself as opposed to, you know what I mean? That, that thing that you really want to be known for.
Kyle Ariel Knowles: And what is your repurposing tool of choice then?
Adam Coughlin: We use both Jasper and then ChatGPT.
Kyle Ariel Knowles: And do you use any AI tools to, I guess, post in multiple locations?
Adam Coughlin: Not currently. I mean, we use like, you know, our CRM of choice is HubSpot. So we're doing that for a lot of our marketing campaigns and email automation. And they have that baked in there, like a social calendar that you can post to and stuff like that to get that process going. And I think that's the key for founders, particularly in the early stage. I once talked to a founder who said, oh, yeah, I do my marketing at 4.30 on Friday afternoon. the key is the consistency of those things, right? And I think that's what you mentioned when you were talking about like the people that are thinking about, you know, do I get into entrepreneurship? Do I work for a startup at ever? And it's like, you know, a little bit of doing is much better than perfect thinking. You know what I mean? And like, unfortunately, like, you can, particularly like the landscape of technology and that evolving ecosystem of the market and the competitive and You know, things are changing at such a rate that like you could spend years trying to perfect something and the moment that you share it with the world, it could become irrelevant. It could be outdated. It's going to have to evolve. And so I think just getting out there and executing off of a plan, learning, iterating, improving is really the best place. And that's where consistency is important, right? I love the saying that intensity is overrated and consistency is underrated. And that is very true, particularly of exercise, something that I never actually paid attention to or follow. But I do believe it on the company building. Putting a little brick down every day is much better. And what happens, especially on the marketing side, is you see somebody and they go, oh, yeah, I need brand building. I need marketing. I'm going to write eight blogs and six social posts. And oh, no, none of those blogs went viral. And those social posts didn't get any responses. So I'm going to go do something else. And then six months later, they say, ah, you know what, I should have done that. And they go back and they do that cycle as opposed to sort of just that consistency, right? And I think that's where the tools can be really valuable to just help you sort of get that calendar filled out where you're just kind of slow and steady when in the race.
Kyle Ariel Knowles: Yeah, I like that approach, just the slow and steady for sure. And the consistency and one brick, one brick laid every day.
Adam Coughlin: Yeah, absolutely. Right. And then I think you can, you can, you can bake into your approach some swings that like, great. If you, you know, it's kind of like our philosophy on the company building in general, right? Like, yeah. Like if you have that brick, then you've built yourself the luxury to take a couple of swings. And maybe one of those things connects and suddenly you've expedited the whole process. But if that swing misses, you're still slowly building. You haven't like, you know what I mean? You're not, it's not home run or strikeout.
Kyle Ariel Knowles: Yeah. You're not going to take nine months off because something didn't go viral. Right. Yeah. So as far as use cases for AI, personally for yourself, what, what has been the most amazing use case for AI for you personally, Adam?
Adam Coughlin: I think it's nice to just sort of have, uh, again, like with, with the startup, you're doing so many different things and you have like, um, some gut decisions that you're making on different things. Like, should I do this? Should I do that? And I almost like it as sort of a sounding board to bounce something off of and kind of like just use that universal knowledge that it has to just allow me to sort of poke holes at something. And maybe I haven't like necessarily thought of or an angle. And that's, I think such an important thing for founders. I always say like, choosing not to do something is a fine strategy. Not doing something because you didn't even know that you should have done it is not. And that's why I think shows like yours are so helpful. So much of the content that exists that can help entrepreneurs just kind of begin to understand the things that you don't know. Because that's like, you don't want to you know, like, had not have done something just because you didn't even know it was a possibility or that you should have done it. And that's where I think, like, that I've enjoyed sort of the AI to be kind of that quick-sounding board. Obviously, I have advisors and different people that I think are, you know, way better. But, you know what I mean, sometimes there's maybe a degree of which, like, you're not going to burden somebody with this quick question. And then there's like a, there's an outlet for it.
Kyle Ariel Knowles: Yeah, I like that. Use case as thought partner, using AI as a thought partner. It's always available. You don't have to wait for your Monday meeting or.
Adam Coughlin: Yeah, absolutely. Right. And I think that like, as I mentioned earlier, like from a value add perspective, we're trying to do things like these roundtables and different things. And it's like, the reality is, is like, there's so much remote work. So many teams are being built completely hybrid, right? There's a lot of like, loneliness in in this and like you can often think like oh, I must be the only person in the world struggling with this problem, right or And that's where like, you know, we like these roundtables because they end up sort of becoming therapy sessions It's just to have that community that you can talk to and be like, okay good Like somebody else is dealing with this as well too. And here's how they're approaching it, right? and I think that that Obviously the human element is the ideal scenario, but to your point, there's that, at least that quick term option that exists too.
Kyle Ariel Knowles: For sure. And I have a few more questions. Adam, I want to get to know you a little bit better. What TV, movie, book, musical, opera, novel character do you most relate to?
Adam Coughlin: Oh, that's excellent. You know, it's kind of funny that you would say that. Like I've always felt that I've been sort of too I've always wanted to be sort of, I've always been sort of two different things. Like I've always, as a young person growing up as a writer, why I got into journalism, et cetera. Like I always wanted to be Ernest Hemingway.
Kyle Ariel Knowles: Okay.
Adam Coughlin: And then it turned out that like, you know, I don't like drinking gin and I'm maybe not into bullfighting as much as I want. And then the other part of me is like Phil Dunphy, who's the father on Modern Family. So I've always been torn between those two worlds of wanting to be like this grand adventurer, but then like at my heart, just like truly like a, you know, a husband and a father. And I feel like I've landed in the perfect mix where company building is sort of like the adventurer for people that get motion sickness, right? Because it's really hard, it's challenging, it's exciting. But then at the end of the day, I can still come home you know, go to my kids' baseball game. And, you know, so I feel like I've kind of, and, you know, building that, building this company in New Hampshire, which is where I've grown up and my family is, working with people that I've really been close with out through my life, I really feel like I've done a nice job of sort of architecting a life for myself.
Kyle Ariel Knowles: That's great. I love that answer. So kind of dual characters mashed into one. A little bit of a mashup.
Adam Coughlin: A little mashup, yeah. And some days one wins over the other in my mind.
Kyle Ariel Knowles: Who has had the most significant impact on your life?
Adam Coughlin: I would say definitely my parents, right? I think they've, you know, like just set the foundation. And, you know, I think it's like, you know, we live in such a chaotic world that especially with like all of the digital media and all of these different things, it can be really overwhelming and it can be really easy to sort of forget like why you're doing the things that you're doing and like what's the point of all of these different things, right? And I think, you know, they really anchored me in, you know, we have a very strong Catholic faith, we have all of these different things, and it's like, really, like, I'm playing the long game, like, I want to get to heaven someday. I want to bring my family with me. I want to bring as many people with me as possible to that. Like, I want to keep that perspective in everything that I do. If I, you know what I mean? If I, if I live like a certain way, I think I can bring that into business, into the relationships that we build in business. And I think those are going to be strong. And I think at the end of the day, hopefully that manifests itself into a really nice company that is, you know, helping people be successful in all of these different things. But it allowed, I think that, that teaching and that growing up allowed me to sort of stay centered in a fairly crazy world. And I've been fortunate enough with my co-founders and the team here to share those sort of same, you know, do right and the rest will take care of itself principles.
Kyle Ariel Knowles: Yeah, I love that. Your parents must have been awesome. Were either of them entrepreneurs or entrepreneurial?
Adam Coughlin: It's so interesting because it's like, That word is so interesting. Cause like, to me, like for a long period of time, it had the connotation of like a hoodie wearing startup founder. Right. And it's like entrepreneurial means that like, you just look at things differently and you love solving problems. And like both of my parents were lawyers, but they started their own law firm. Right. Like that's very entrepreneurial. Like I didn't even realize, like when I was a reporter at the first part of my career and you're responsible for. your stories and going out and getting the interviews and doing all of these things, like that is an entrepreneurial approach to those things. And so that's where I always say, like, I love the entrepreneurial mindset. I think building a company is an awesome way of using it, but I think it's a skill that like we should continue to teach and showcase to young people because we would all be beneficial. I think if more entrepreneurial minds went into education or law or medical practices or whatever, you know?
Kyle Ariel Knowles: I agree. And I think you can be entrepreneurial even if you work in corporate, you're working anywhere. And to me, it just reminds me entrepreneurs or being entrepreneurial is that growth mindset. And it's also kind of that extreme ownership, right? you're you're going to make something happen. You're you know, the buck stops with you and you're going to make something happen. You're going to be creative. You're going to find creative solutions to solve problems. So I love that that your parents were very entrepreneurial because they went into business for themselves.
Adam Coughlin: Yeah, absolutely.
Kyle Ariel Knowles: That's great. So I have a lightning round of questions before that. Is there a book that you recommend the most to people and if there is what what is that book?
Adam Coughlin: I really like this book called the third door, which I think is particularly valuable for young entrepreneurs. And it's, it's sort of that exact concept, which is like, there's the first door, which most people take, which is just waiting in line and waiting for your turn. Then there's the second door, which is like, and he uses the kind of analogy of a, of a dance club. Right. And then there's the VIP, like, you know, some people are just born with better access and everything. And then what this author found was like the most successful people find the third door, which is like, they figure out how to get into the back alley and sneak into the club. Right. And I think like, just having that mindset that like, you know, you can accomplish anything if you like, kind of like outthink and, and, and outwork people. And I think that is a universal approach and mindset that I think would be really valuable, irregardless of what path you end up taking in your career.
Kyle Ariel Knowles: I like that. I can't wait to check that book out.
Adam Coughlin: Yeah. It's a good read too. It's fun.
Kyle Ariel Knowles: Yeah. Cause it's almost like where there's a will, there's a way to kind of get into that building, whatever it is. And, uh, you see two doors, but you're going to figure out even a third to, to make sure you get in there. So lightning round of questions. My, my first question for you is your favorite candy bar.
Adam Coughlin: I'm going to go with Snickers favorite music artist. I'm going to go with Simon and Garfunkel. I used to listen to I played this is now I'm getting off your lightning. I'm sorry, but I played football, but I was the quarterback. Okay, so the locker room was super loud and like AC DC, but I needed to stay like super calm. So I would listen to the sounds of silence by Simon and Garfunkel and now my 12 year old son is a quarterback and we listen to that on the way to his games as well too.
Kyle Ariel Knowles: just to put him in the zone and relax him. Yeah. That's great music for it. Favorite cereal?
Adam Coughlin: Probably life. Maybe there's a metaphor there.
Kyle Ariel Knowles: Mac or PC?
Adam Coughlin: Oh, Mac.
Kyle Ariel Knowles: Google or Microsoft?
Adam Coughlin: Google.
Kyle Ariel Knowles: Dogs or cats?
Adam Coughlin: If you had met me prior to being married, I would have said dogs, but my wife had a cat and now I'm very pro cat.
Kyle Ariel Knowles: Phantom or Les Mis?
Adam Coughlin: Oh, I'm going to go with Phantom.
Kyle Ariel Knowles: Okay. And the last question I have for you, Adam, is what's the worst thing about being an entrepreneur? And what's the best thing about being an entrepreneur?
Adam Coughlin: I would say the worst thing about being an entrepreneur is that there are constraints on time. in that there's always so much to do and that you have to figure out how to do, you could exponentially work every single day, all the time, and you have to figure out necessarily, like, how do you do that without sacrificing every other aspect of your life? That's the hard part. And then the good part is, like, it's kind of funny, like, my kids were out there, like, a program that they were doing and it was dressed like your parents. And my son said like, what's, you know, he's 12 years old. It doesn't think I dress cool. He's like, what's the coolest thing you even own? And I'm like, well, what about a shirt with the logo of the company that I helped build? Like that feels pretty cool. Right. And I think like that, being able to build something from scratch that other people find value in and it begins to be a part of like their workflow and helps them achieve their dreams is like, it's just about, I think as cool as, as anything.
Kyle Ariel Knowles: I love those answers, Adam. Thanks so much for being generous with your time today. I've really appreciated the conversations about AI startups being pragmatic and growth and also responsible fundraising. I look forward to seeing how you and your co-founders do over the next few years, especially now that AI is so big. You know, so many companies are being started now because of AI and this AI boom, if you want to look at it that way. But thanks again for being so generous with your time. I've learned so much with the conversation today.
Adam Coughlin: Well, thank you for having me. And thank you for doing this is a great speaking of adding value, just a great value resource for everybody.
