The Achieve Podcast - Ramesh Swamy (Halifax West)
In this episode of The Achieve Podcast, host Jesse Warner interviews Ramesh Swamy, founder and chairman of Halifax West, a merchant‑bank focused on independent sponsors and capital‑solution services for privately held companies. Swamy recounts how Halifax West grew from a moon‑lighting advisory side‑project in 2015, after leaving a senior consulting role, to a full‑time firm in 2019 that now employs a hybrid on‑shore/off‑shore team of roughly 10‑15 core staff plus interns. He explains the firm’s evolution from a broad advisory practice to a narrow, deep merchant‑bank model that underwrites deals, structures financing, and co‑invests alongside independent sponsors, charging only success fees. Swamy details how AI is used for business‑development research, email personalization, deal‑screening, and daily briefing agents, while warning of over‑reliance and the need for human oversight. He outlines three macro trends driving demand: baby‑boomer exits of sub‑$10 M EBITDA businesses, the rise of private‑credit funds in the lower‑middle market, and the growth of independent sponsors who raise capital on a deal‑by‑deal basis. Scaling challenges stem mainly from talent constraints on the supply side, especially for capital‑solution work, which AI cannot fully replace. Lessons learned include focusing narrowly rather than being a “wide‑shallow” firm, avoiding operating acquired businesses, staying on top of rapidly changing market regulations, and maintaining rigorous AI checks. Swamy advises aspiring entrepreneurs to “burn the boats,” commit fully, and consider entrepreneurship‑through‑acquisition, leveraging co‑investment and mentorship. Looking ahead, he is excited about meeting the overwhelming deal flow demand, expanding the supply of talent, and capitalising on seasonal market cycles. The interview closes with Swamy’s personal commitment to the International Pemphigus and Pemphigoid Foundation, a nonprofit he chairs after his own rare‑autoimmune disease experience, highlighting his advocacy and fundraising efforts.
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Welcome to the Achieve Podcast, the show where we highlight the leaders, creators, and entrepreneurs who are building meaningful businesses and shaping their industries. My name is Jesse Warner. I'll be your host today. We're excited to have Ramesh Swamy today, who is the founder of Halifax West. Ramesh, great having you on the show today.
Thanks so much, Jesse. I'm excited to do this.
So our audience can kind of get to know you a little bit better, tell us the quick backstory of Halifax West and kind of how it all started.
Yeah, so, so there's a pretty good story here. So basically I was at a very big firm and I was the, uh, you know, retail leader for, you know, a big, big consulting firm. And I used to be in the media a lot and do a lot of different things, um, serve our biggest clients and that sort of thing, a lot of private equity firms and such. And then I decided in 2015 to become an operator. And the reason I did that is because, you know, I was tired of being on the road all the time. I lived in LA. I would serve big clients across the country, and one of my biggest ones was at CVS in Rhode Island, and I'd have to go back and forth for years. And so I decided to, you know, get off the road, and I became an executive. And so I joined a local company, one of our audit clients it happened to be, but I ended up joining as one of their most senior executives. And what happened then was a lot of folks from my old life started calling and asking for advice. So that's kind of how Halifax West got started. It was kind of, I'll call it a moonlighting type situation. So I would just do some stuff on the side and help guide private equity firms primarily and other companies through various different things. And ultimately in 2019, I decided to do this full-time and that's kind of how it started. And it's interesting if you want to hear more, basically the journey started where we were a broad-based advisory firm. So basically we would do transactions, restructuring, and operations. We did that for a few years. Then we went into a stint where we were still doing that and we decided to add on buying companies. We decided we're not very good at that. That's a different business than advising companies and operating them. So that was a little bit of a different model for us. So we moved away from that in probably 3 years ago, and we started focusing specifically and exclusively on our merchant bank. So right now we only focus on transactions and we serve 2 audiences. One is independent sponsors looking to buy companies. Another one, the other audience is privately held, closely held companies, I'll call it, usually family owned or Privately held, where we help them with basically capital solutions. So help them create balance sheet efficiency.
So 2019, you decide to go out. Was it just you or did you have partners with you?
Nope, just me at the time. Just me at the time. And then then we've actually built up and we've we've grown.
And how big is your team now?
It's hard to say. So there's people that are on our website and there are people that aren't. So there are people that are you know right now I think I don't remember on the website maybe I don't know six or eight people plus. We have about anywhere between 8 and 10 interns at any given time. So somewhere between, call it, you know, high teens. And then, um, there are people that aren't on the website that are, call it Halifax West Tangential. And, and, and there are probably gonna be a handful of those too. So people that we partner closely with. So there's quite a few people in the, in the ecosystem.
So first of all, congratulations on growing business. It's hard to kind of get past that You know, those first few employees and say, okay, now I've got a real business. You know, you don't have to wear all the hats.
Right.
But you've got a business now that's growing. You've got multiple people on your team. How has that changed the way you do business as you've grown?
Yeah, so I'll tell you, when we first started, what I would work— I worked a lot with a team in India. So it was me, I had like marketing folks, and I did have some analysts kicking around and interns too. But it was mainly using the India team primarily for what I was doing. And then I started moving to having an, I'll call it an onshore team, you know, probably starting in '21 or '22. Because '21, I spent basically all of '21 as an operator again, because again, back then we would do 3 things, right? We would do operations, restructuring, and transactions. So at the time, I actually was an interim executive at another company turning it around all of '21. So I didn't really need the big team then because I was running a company primarily. And then in '22, I started to bring on, I'll call it onshore resources. And it's been great. It's been great. I think one of the things that's actually changing the landscape of how you bring on talent and also engage talent is AI. So we're really, really seeing the impact of AI because we are a people business, right? We provide a service, you know, conducted by people. We're not selling widgets or anything like that. And I think AI is creating a meaningful impact in what we do.
We can jump to AI. It was gonna be one of my questions a little bit later, but let's talk about AI and automation. How are you using it today in your business?
So in our business, we, you know, obviously there's, there's a couple of phases to our business, right? So there's one phase, I'll call it the business development side, right? Where we actually go out to try to attract clients. In that phase, we are pushing more to AI to try to automate some of those processes, right? So for example, sending emails and things like that, really tailoring emails. spending a lot of time doing research that would take, you know, tens of, you know, man people hours versus now AI can do it in, in seconds and, and really you don't have to do much, right? So we're spending a lot of time on researching potential clients. And then we also, because of our model, we have a lot of, um, um, independent sponsors that we work with in our network already and they're always sharing deals with us, but we are spending time creating meaningful content for them, right? So there's a lot of research involved there and then outreach and those sorts of things. So that's on the business development side. That's what a lot of people are using it for. And then on the execution side, we're really trying to streamline what we're doing here as it relates to execution. And that is, you know, post-signing on to an engagement and actually doing a project for somebody. We're using it to help, you know, speed up the materials prep processes, speed up again the engagement and outreach with potential, call it investors/lenders, and that sort of thing. So there's a lot of there. We're trying to use it more for process-oriented things. Me personally, I'm using the agents as well. So every morning I get up and I'm pointing at my other laptop. That's my laptop I used to work. It— the, the, the ChatGPT goes out and it looks at my calendar. It looks at our CRM at MidMarket and looks at all the emails I've received related to my calendar, and it gives me a daily recap first thing in the morning. Okay? So first thing I do, I wake up, I read that, and I see what's on my calendar for the day and what's germane to what's on my calendar. So it tells me what we've discussed with that opportunity before or that particular stakeholder. It also goes through the emails and it consumes the data and it tells me what to think about in terms of that. So it really speeds up my day. So that's one use case I have for it, but I'm using it for so many things now, especially the agents. I think it's been really helpful to me.
Yeah, and it's changing so fast too, right? Yeah, what you used to not be able to do a couple months ago, you can now do, and the quality continues to improve as well, which is Just a lot of fun to be a part of, right?
Now, having said that though, and not to cut you off, but there is a downside. So one of the things we struggle with, and I'll constantly— I'm on the team about— they probably want to kill me if they watch this podcast. They're going to say, oh yeah, no, you shouldn't have talked about that. But I'll say it anyway, is overreliance on AI. So AI makes mistakes a lot. And I say this on every call, AI lacks context. It doesn't know contextually what you're doing. It only sees what's going on, but doesn't know what's happening behind the scenes and what the conversation conversations have been between me and you, Jesse. Then it knows I'm doing a podcast with you and it knows I'm gonna be discussing certain things with you. But what it doesn't know is the context behind all of this, right? And so there's a little bit of lack there and sometimes it, it will misread the situation. So, you know, it'll send an, you know, if, if we use it to send emails, it can send an email that's not meant right by way of tone or it doesn't have the same context associated with it, right? And so there's a lot of that that happens that we're working through.
Right?
And so that, that is really where the downside of AI is. Unless you're watching it, it still needs a human oversight. So it's like my Tesla, right? I let it self-drive. Okay? But it, I'm always behind the wheel. Right? And I think that behind the wheel piece, sometimes you get a little complacent about, and then it ends up doing something that's not correct, and then you end up sending it to somebody and it turns into a bit of a, a problem. So we have really spent a lot of time making sure that, that we put the checks and balances in because There have been issues. So I'll just say it that way.
Yeah. Let, let, let it create the first draft, but don't send the first draft.
Right? That's exactly right. Yeah. I never let it submit anything or send anything on my behalf unless I've reviewed it.
Yeah. Let's talk about sales, marketing, outreach a little bit. Where are you seeing traction as you try to grow?
So our business model is one that is very interesting. So we have a captive, I'll call it audience, because we cater to what's called independent sponsors. Are you familiar with that term?
I don't know if I do in your context.
So I'll tell you 3 macro trends. Well, 2 major macro trends, right? So one is— well, they're really 3. So basically the first macro trend is between now and I like to use 2030, but it can go on beyond that. You have a lot of baby boomers exiting businesses that are sub-10 of EBITDA. Okay, so there's that. In years past, you know, decades past, A lot of these businesses may have just closed. The owner says, okay, I'm getting too old, I'm just going to retire, and the business is gone. Or somebody takes it over, but it's not like a formal thing. So that's happening. So all of these businesses now have to exit. So you know that's happening. That's just a big trend right now. So a lot of businesses are coming on the market to sell. The second trend, what that led to is the rise of private credit. So there's a lot of people entering the lower middle market with private credit funds versus the old bigger funds or banks or anything else. People are really catering to the lower middle market. You're seeing a lot of activity there. The third trend that's been led to by both of the first two trends is the rise of the independent sponsor. An independent sponsor is a private equity firm that does its transactions on a deal-by-deal basis. They don't have committed funds. Okay, so they raise equity on a deal-by-deal basis, debt on a deal-by-deal basis. Okay, that's our main client on the buy side. We right now have, I think, over 200 independent sponsors in our network we've spoken to and we've actually looked at deals with. So what that basically means is our marketing really doesn't have to be too much to like hard sell you. I'm not here saying, Jesse, hey, here's our product and we're trying to hard sell you on it. What we have to do is simply to stay in touch with these sponsors because they are looking at deals every single day. They're getting deals in their inbox every day. What we want them to do is send the deal to us for us to screen it with them. So we underwrite the deal upfront. We help them structure the deal, help them get an LOI in place, right? So all before we even sign an engagement letter, we do that for them. So that's our form of marketing. So rather than us trying to hard sell people and trying to, oh, hire us, hire us, we don't have to do that. We simply look at deals together with people and we show them, hey, the best way to know what we do and what you do and get to know each other is to look at a deal together.
Really, you're going down that partnership strategy, everything you're doing. Most, most of your lead flow is coming from those relationship partners.
On the buy— that's on the buy side. And the reason that works is because we are a true partner. We help them structure the deal, we underwrite the deal, we do all the analysis. We even call the broker sometimes, or the banker on the other side, and help them convince them that, you know, this is the right party, because we create certainty of close just by our, our skill set and reputation. The second thing we do is we go out and we get the debt for the guys, right? So our gals. So we go out and we get the debt for them, right? Such that they don't have to. And that's a monumental lift sometimes. Getting the debt is a real pain. You have to go out to a lot of stakeholders. You've got to create materials. You've got to answer Q&A questions. You've got to— it just takes up a lot of time. So we take that off their plate. The third thing we do to actually become a real bona fide partner is we co-invest. Okay? So in a transaction with them, We'll say, look, we will co-invest alongside of you. And that comes from a different pot of funds. And so that's kind of our model. And so because we do those 3 things and we don't take a retainer, everything we do is success fee. Because of all of those dynamics, we're basically risk-free. We are a true partner. We are aligned in every sense of the word, right? We're putting our time in, we're handling the transaction, and we're putting our money in. So we are 100% aligned. If that deal doesn't close, we've lost a bunch of time. Right, which we can't ever get back. That's our, you know, our biggest resource.
So let's talk a little bit about, as you try to scale and grow your company, where do you— where are you hitting constraints and where are you hitting the wall and kind of having to rethink things, redo things? What does that look like on your side?
Yeah, that's a good question because that is the issue. Our issue is not demand. We have more deal flow than— I can say this, I don't know I think we have as much or more deal flow as anybody because of our model, right? And I firmly believe that nobody else really has emulated our model and probably shouldn't even be talking about it because people are going to start to do that now. But our deal flow is extreme. When I get, you know, we get congratulations emails from people saying, you know, we've seen so many deals from you, this is unbelievable, right? Everybody else is slow, but you guys are fast. What is going on? It's because of our model, right? And so there's that. That's really on the independent sponsor side. Where we could see more growth is on our capital solutions business. And that's where we're focused now, right? Because we see deals every day on the independent sponsor side. We don't see capital solutions deals every day. And those are what many call direct deals. So basically it's a company looking to refinance. That's where we see we need to do a lot more growth from a demand standpoint. As it relates to our supply, that's another issue. We do need more people. That's our biggest constraint. Because we can pick and choose what deals we do today, right? We have the luxury and the capacity to do that because we have so many deals, right? But there's probably deals that we want to do that we can't because we just don't have enough people. And so that's really where I think we need to focus. Now, AI helps that to a certain degree, which we discussed earlier, but it doesn't completely alleviate the problem. And the reason is there needs to be a human being sitting behind the screen here and having that conversation. Right? AI can't do that. And so there's not enough of, for example, me to go around, right, to have those conversations, right? And so that's what we really need to focus on a little bit more, if that makes sense.
Yeah. Let's look back for a minute, Ramesh, and think about kinda your journey here.
Yeah.
Some of the wins, the mistakes. What are some of the lessons that you've learned along this path?
Yeah. Look, I think we've learned a lot of lessons, right? So number one is Don't try to do too much, right? Again, we were a broad-based advisory firm. We had a lot more people at one time, by the way, and we were doing different services, right? We were trying to do a lot of more broad services. What we came to realize is, is not that we're not good at those, but you can only focus on so many at one time, right? So you can either be really wide and shallow, or you can be narrow and deep, right? And it's not necessarily a choice, but I think We made a choice. We said, okay, we're not going to be wide and shallow. We're going to be narrow and deep. That's number one. Number two is we needed to realize because we know how to buy businesses, we can buy businesses really easy, Jesse. I can snap my finger and have 5 if I want, literally. And I can do that very quickly only because this is what we do. We're in the business of buying businesses. The problem is once you buy them, you got to operate them. And I think that's another different business that we're not in, right? So we said, you know what? We should probably not be in that business because we don't have the time to dedicate to do that. So that's another lesson we learned, right? In terms of other things, I'm just trying to think about other lessons that we've learned. I think, you know, I think those would probably be the 2 main, right? Just try to stay focused and, and try to grow that way. I think, you know, obviously I've talked about some of the AI lessons, right? If something, if something is, is, is done through AI. But so we learned a lot through that and we, we're constantly learning, by the way, right? We're learning the market. Even though we have probably thousands of lenders in our database and we're learning how best to engage with them and the market is constantly changing. And I think that's the last key I would say is because this is such a fluid market, it's changing so quickly, right? So for example, and we don't do many SBA deals, but the SBA is changing their regulations nonstop. And there's a new rule that's coming out, I think in October, that's creating a lot of buzz in the lower middle market. So you've got to stay on top of all of these things. That's another big thing. It's just the market is changing so quickly, right? Especially when it comes to investing in companies, it's when it comes to lending to companies, uh, even that SBA side, the, the, the, the players are changing, the size ranges are changing, everything is changing so quickly. And so we got to be mindful of that.
So you shared some good lessons. What, what advice would you give to other entrepreneurs who are kind of going through what you're going through?
Okay, that's a good question. So most entrepreneurs— there's 2 types of entrepreneurs, I would say. There are entrepreneurs that are like me that are starting something, right? And so that— I'll talk about that first, right? So typically when you're an entrepreneur like me starting something, you've had a job before, right? So I think the first thing you have to do, unfortunately, which— and people aren't gonna like this, but, you know, I think at some point, you know, you can start, you know, doing this entrepreneurship as a moonlighting thing. But at some point you have to actually jump in and I call it, you know, burn the boats, right? Like there's no going back. Boats got burned. You're on that island and you gotta see it through. A lot of people will, you know, do this kind of half, you know, half and half thing for a while. And I learned this lesson too. Do the half and half thing for a while and then they will try to get onto the island, but they won't burn the boats. So they always have an escape hatch to go back, right? The training wheels will never really go away. They're there. They take them off for a bit, but they still have them in the garage so they can put them back on. I say, you know what, throw the training wheels in the trash, you're done. You got to burn the boats, right? And it's very uncomfortable. Oh my gosh, the very first 2 weeks when you don't have a job and you don't get the paycheck, after about 6 or 8 of those weeks, you start to think, what in the world did I do? You start to get nervous, right? That's normal. And I coach people through that. Oddly enough, there was somebody else that left their job in finance and a bank. And they started to do what we do kind of thing, right? And I said to them, anytime you want to talk about what that feeling is, and when you get that feeling and you have your resume ready and you're about to apply back to a bank, call me first. Call me because I can tell you that there's light at the end of the tunnel. Don't give up easily. Now, if you do this for 5 years and you can't get any traction, that's a different story. I'm not saying then your business isn't right because that's a different issue, but I'm saying you have to burn the boats. So that's the kind of thing you have to do. And so this partly applies to the other part of entrepreneurship. The big thing we're seeing is entrepreneurship through acquisition, right? That is an independent sponsor. An independent sponsor is an entrepreneur that's acquiring businesses to become an entrepreneur, right? They're acquiring businesses. Their entrepreneurship is the business of acquiring businesses and bringing them in and managing the portfolio. So entrepreneurship through acquisition. That requires, again, a little bit of skill, right? So they'll make a lot of mistakes. We have had the good fortune of making every single mistake in the book when it comes to doing deals. We know what works and what doesn't because we've made every mistake, right? So what we always advise people, and they don't have to follow our advice, but we work with a lot of first-time sponsors. Spend some time with us. We'll show you the ropes. We'll do a couple of deals together. Then maybe you can do a deal on your own. Maybe you still want to work with us.
We're fine.
Right. But we've worked with sponsors that are some of the most experienced sponsors really out there, and they still find value with working with us. So we know that we're doing something right. We found like, you know, money that they wouldn't otherwise know about because not everybody's going to know everything about the market because we have our ear to the ground. So we know the market. They may not. And so there are ways that we can actually still add value if you're a longtime sponsor, but specifically to a first-time sponsor. We can be enormously valuable. Enormously. You can just work with us, do a deal together. We're co-investing in the deal anyway, so we're in the deal with you. And so at the end of that, you'll see, okay, oh, I see what, you know, how these guys do things, how the deal needs to be structured. Some of the, some of the tricks of the trade, I guess, is what I would say.
Well, what great advice, right? I mean, first of all, it's scary being an entrepreneur, right? Especially that first leap, but you gotta take the leap, right? Burn the boats. Go all in, um, and then, and then embrace that, right? And, and work through the challenges instead of kind of giving up on those challenges. Uh, some great advice. Last question for you, Ramesh. As you think about the future, what are you most excited about? What, what are you energized by?
Yeah, look, there's, there's so much. I think that, um, the, the amount of entrepreneurship through acquisition or independent sponsor, those mega trends, the macro trends, I should that I was speaking about earlier, those are still reaching, you know, fruition. So we're always seeing new and exciting ways to get deals done and new and exciting ways to help our clients. And so I am very thrilled with where we are today, what the future looks like from a demand standpoint. I think what we need to solve for and what I'm excited to do is solve for the supply side, right? Because we could probably, you know, bring on as many people as we want And still not meet the demand, to be honest. We're very fortunate, right? And so I think what we're looking at is various options to try to meet that, you know, supply side, right? We could go in organically and, you know, do what we keep doing and bringing on more people. We could try to partner with other people. There are so many different opportunities out there. And so I'm excited to see kind of as things unfold here. It's what, 9/15 today?
9/15.
9/15, September 15th, 2026. I'm excited. Between now and the end of the year, basically the deals start to slow down, right? They say never take a deal to market past Thanksgiving, right? Because everyone's on holiday. So you're going to start to see less deals coming to the market, and that gives us time to work on our internal growth, our internal— shore up our internal mechanisms. And so all of those strategic conversations can happen with us internally, and all of those conversations can happen with third parties. And so we're very excited. I'm looking forward to that. And then obviously '27 will be even bigger than '26. And as it goes, it continues. So we're very like, this thing is going to be like a ball rolling downhill. So we just need to keep it going.
Well, Ramesh, thank you so much for joining me today, sharing your story. I do want to give you a moment. I know right before we started the podcast, you mentioned that you are part of a nonprofit organization. Yes. And you're the— I think you said you're a chairman of the board on that. Tell us a little bit about that organization as well.
Yeah, so that is the International Pemphigus and Pemphigoid Foundation. It's a mouthful. So basically what that does is it helps support patient care, research, and a whole host of activities for people with that disease. So pemphigus and pemphigoid are rare, ultra-rare, or very rare, they call autoimmune diseases. And what it does is the immune system attacks your skin. So back in 2015, you know, one day I woke up, I think I was in Italy on vacation, and my gums were falling out of my mouth, literally. You picture that, pieces of your gums just falling into your hands, right? And I won't go through my whole diagnosis story, but it took about 17 months to diagnose me with this disease. And all of that time, I started, you know, having those symptoms. I was having lesions appear on my neck and head and on my body, and those lesions would break. And I literally would be walking around, Jesse, we could be doing this podcast and my head would be bleeding, open head sores. Okay, this is back in— 2015 through the end of 2016, and I went into remission in 2017. So that's kind of my disease journey, and it's a lot of talk. There's a lot more conversation there. But basically at the end of that disease journey, I said, okay, I'm in remission now. Now I need to find a way to give back. And so I found the foundation, joined their board, and then over time, you know, I think I just became the chair. Maybe because nobody else wanted to be, but it's a lot of work. But I think what we're trying to do now is really raise awareness this rare disease. We're trying to help patients as much as we can. And raising awareness would lead to raising money and providing more services that we need to provide more to this community. And so I just wanted to make a— thank you for allowing me to make a plug on that. It's very important to me. Something that actually affects my daily life. I've been in remission for 9 years. Any minute now, I probably will not be in remission, and then I have to go back to the treatments. All that stuff, right? And so I knock on wood today. I'm still in remission, but I know a lot of patients are suffering through this. We just had our conference 2 weeks ago in Chicago, and it was well attended. It was fantastic. We have all the top doctors in the world. And so anybody that wants to donate, please, pemphigus.org is our URL.
Yeah. Well, thank you so much, Ramesh, for joining. If you want to— for those listening, if you want to learn more about Halifax West. I invite you to go to their website, halifaxwest.com, as well as learning more about the nonprofit organization. I will include a link to both of those, uh, as we post this. And that'll wrap up today's episode of the Achieve Podcast. A big thank you to our sponsor Achieve CMO, which provides fractional marketing leaders for growing businesses. And if you enjoyed today's conversation, invite you to follow the show, invite other entrepreneurs that also find value in it. And again, thanks for listening. We'll see you on the next episode of the Achieve Podcast. Ramesh, again, thank you for joining us.
Thank you so much, Jesse. I appreciate it. It was a lot of fun.
