EPISODE 230. This Shoot the Moon episode defines the real-world differences between a boutique M&A advisor and a middle-market investment bank, specifically for IT services founders. The team explains where banks shine (IPOs, capital raises, complex financings) versus where operator-led advisors excel (industry specialization, targeted processes, hands-on counsel). They contrast deal sizes and focus, why advisors lead with strategic and cultural fit before price, and how staffing models differ (partner-led vs. analyst-heavy). You’ll also hear how “long-tail” sell-side readiness (months or even years before market) can materially improve value, and the practical questions to ask any firm before you sign a mandate. Pick the partner who maximizes certainty of close, cultural alignment, and net proceeds—not just the biggest logo
Advisors vs. Banks = different centers of gravity. Banks are great for IPOs, raises, and complex financings; advisors excel at sector-specific sell-side processes.
In IT Services, specialization matters. Operator experience helps craft story, vet culture, and identify “1+1=3” combinations.
Lead with strategic + cultural fit. If those are right, the financials usually find a path.
Staffing models differ. Expect partner-level guidance throughout with advisors; banks skew analyst-heavy.
Start early. Long-tail readiness work (growth, margins, positioning) boosts value and certainty when the market moment arrives
Mike: Hello and welcome to this week's. Shoot the moon p..., are my partners, matt Lockhart and Ryan Barnett, welcome guys.
Matt: And good to be here and good to be back with you g...ime to get a lot done. So, what are we getting done today, Ryan?
Ryan: Absolutely. You know, I'd love to go back to Mike....ent bank, which seem like bankers. And I really want to kind of and would love to dig into the differences between an operator-led M&A advisory firm and a generalist investment bank. And so, Mike, I want to start with the definition of M&A advisor. You know, we kind of know ourselves as an M&A advisor. How would you define it and help me understand what is an M&A advisor?
Mike: Yeah, sure thing, Ryan. So, you know, an M&A advisor is a firm that can help companies either buy companies or sell companies, and generally they have deep specialization in a specific niche. And, you know, that’s different than an investment bank in that they may have more specialization in particular disciplines and industries than maybe growing up in finance.
Ryan: Sure. So if I was to say the roles of an M&A advisor, a lot of times that includes valuation, packaging, market outreach, and full support across diligence to close. And with an investment bank, you’re really thinking a bit more broad—IPOs, capital raises, take-privates, debt placements—those kinds of things. Matt, you’ve worked with both worlds quite a bit. How would you define that? Yeah, let’s just start there. What is an investment bank?
Matt: Sure. Well, you know, a key piece that investment bankers bring is their ability to participate in public-market transactions and complex capital markets work—IPOs, follow-ons, debt placements—and they can be involved in capital raises, right? Where they’re just raising capital for a company rather than running a sell-side process. That access to and experience of working within the public markets is a key difference.
Matt: …raising money from the public and/or private sources. And that’s the broader mandate that comes with an investment bank—versus a boutique advisor that focuses on M&A processes. That access to and experience working within the public markets is a key difference.
Ryan: Sure. So when you think about that investment bank, think about that massive umbrella of capital markets work—IPOs, debt, follow-ons, take-privates—plus M&A. With that in mind, Mike, can you contrast typical deal sizes and focus areas they go into?
Mike: Yeah, you bet. Typically, middle-market M&A advisors are very specialized in their niche—sector, sub-sector, even deal type—and they run focused buy- and sell-side processes. That’s a little different than the generalist approach you might see at a typical investment bank. When you’re in a niche market like IT services, specialization really matters.
Mike: …as a middle-market M&A advisor, we have the luxury of being very focused on a specific niche. In our case, IT services.
Ryan: So, in that case, you know, oftentimes when you hear us talk about fit, we’ll say “strategy and culture first, then financials.” Why is that? Why do advisors in our space tend to lead with strategic and cultural fits first compared to just focusing on the financials?
Mike: Well, it’s been, at least in my experience over the last many years—we’ve been doing this a long time—that if you can get strategic fit right and cultural fit right, you can almost always find a path on the financial fit. Conversely, if you lead with financial fit as the first criteria for measuring the deal, you can often run into trouble later.
Ryan: Sure. So, M&A advisors do a great job on establishing that strategic and cultural alignment. I think that’s a differentiator compared to some of the more generalist models you might see in other firms. Can you walk through that a little bit?
Mike: Yeah. I mean, I think that—
Matt: Well, let’s kind of take a step back. As a middle-market M&A advisor with a lot of time in one industry, we also tend to be closer to founder-led companies. That focus allows us, I think, a greater level of empathy to that particular journey, and it influences how we design the process.
Matt: …and understanding the journey of that particular founder—importantly, aligning strategic fit and cultural fit—and then, as Mike said, lining up the very best financial fit.
Ryan: Yeah, well said, Matt. I think that was really great. And I’d love to pivot to readiness. For a founder listening who might be 6, 12, even 24 months out, what can an advisor do to perhaps get your firm ready for a sale when the timing is right?
Mike: Yeah, that’s a great question, Ryan. You know, one of the things we’ve always done with our clients is take what we’ll call the long view—really working in the long-term interest of our clients.
Matt: Mind.
Mike: And not to say that investment banks don’t, but they’re certainly wired to move transactions along quickly when a process is live. Advisors who take that longer view can help you build value ahead of a process—things like refining the story, operational tune-ups, and getting profitability levels where they need to be in order to attract the best buyers and terms.
Mike: …to maximize value. And in that case, you need an outside advisor who will help you craft the story, identify the best-fit buyers, sequence the outreach, and then support you through diligence. That’s where advisors can really lean in—frankly, even a year or two before you plan to sell—so they can provide strategic advisory on how to build value.
Ryan: Yes. Well, I think that’s it—well said. Really, the other piece I’d love to hit is alignment. How do you ensure there’s great alignment in going to market with the right partner?
Matt: Yeah, I think that, first off, industry experience matters. You want someone who speaks your language, knows the buyer universe, and understands the nuances of your model. And you want a team that’s going to be in the trenches with you—day-to-day—so when you reach that finish line, you’re in the best shape possible.
Ryan: Yeah, that’s all great advice here, Matt. I really appreciate it. I’d echo: get a partner you trust, who’s proven in your space, and who will show you the actual process calendar and team doing the work. You want to know exactly who you’re working with that has industry experience and that you’re going to hear from every week.
Ryan: …to be able to communicate effectively with. So, I really think, for founders, that alignment and cadence matters. With that, I’ll turn it over to you for any closing comments or thoughts.
Matt: No, I really appreciate it, Ryan. I think that it’s an important conversation—advisor vs. bank—and the big takeaway is pick the partner who fits your business and goals. Mike?
Mike: Yeah, I would agree, Matt. I think it’s an interesting topic and hopefully helpful to founders out there. Choose the partner who brings real specialization in your market and business—and you. So with that, make it a great week.