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Karen Bennett on Why Doyenne Advisory Group Works Both Sides of the M&A Table

Karen Bennett, managing partner of Doyenne Advisory Group, shares how a finance turnaround career led her to build an M&A advisory firm focused on AI infrastructure and behind-the-meter energy deals.
Host: Anthony V. Codispoti
Published: Nov 4, 2026
Karen Bennett on Why Doyenne Advisory Group Works Both Sides of the M&A Table

🎙️ From a Negative 9% Margin to Positive 19%: Karen Bennett's Path to Doyenne Advisory Group

In this episode, Karen Bennett, managing partner of Doyenne Advisory Group, shares a three-decade finance career that spans portfolio analysis at Chase Manhattan Private Bank, corporate turnarounds, ERP rollouts, and over a decade of independent M&A consulting before she formally launched her own firm in 2022. Karen opens up about a Goldman Sachs interview where her marriage was used against her, why she walked Doyenne away from capital raising entirely, and how the firm now concentrates exclusively on AI infrastructure and behind-the-meter energy deals in the lower middle market.

✨ Key Insights You'll Learn:

  • Turned a sales region running a negative 9% gross margin into a positive 19% within 12 months

  • Cut a company's outstanding payables by 90% in just three months during an interim CFO assignment

  • Spent over a decade doing independent M&A consulting before formally launching Doyenne Advisory Group in April 2022

  • Deliberately pulled the firm away from capital raising services after unspecified “war stories” made the work untenable

  • Works both sides of the table, concentrating most heavily on buy-side clients like family offices and high-growth companies

  • Chased one acquisition target through 15 rejections over the course of a year before finally landing a yes

  • Screens every sell-side client first for owner dependence and customer concentration before taking them to market

  • Sharpened Doyenne's focus to AI infrastructure, alternative and behind-the-meter energy, and technology-enabled SaaS businesses

  • Operates in the lower middle market, generally serving companies with $10 million to $150 million in sales

  • Uses AI for analytical tasks in her own practice but insists human judgment remains irreplaceable in complex deals

🌟 Karen's Key Mentors:

  • Her Master's Program Faculty: Sparked the shift in her relationship to learning, opening doors she hadn't previously seen as open

  • The Goldman Sachs Interviewer: His rejection based on her marital status became a formative, painful lesson in not letting others' assumptions define her career path

  • Her Buy-Side Family Office Clients: Years of working closely with them shaped her acquisition thesis methodology and her scrutiny-driven approach to due diligence

  • Her Deep Technology Sector Network: Built over 25 years, this network shaped her natural evolution into AI infrastructure and energy-focused advisory work

👉 Hear how a finance veteran who once turned a failing sales region profitable within a year built an M&A advisory firm laser-focused on AI infrastructure and the energy powering it.

Listen to the full episode here

Quick answers

Why did Karen Bennett establish Doyenne Advisory Group?
She wanted to build an advisory firm with its own methodology and standards, rather than continue taking individual consulting projects.
What does M&A readiness mean to Karen?
Preparing strategically before a transaction is underway, so key issues are addressed before buyer scrutiny and negotiating leverage become time-sensitive.
What should a business buyer prepare before an acquisition?
Karen recommends clarifying the acquisition goal and thesis, and making sure the buyer has financing, an operational plan, and a team ready to absorb the company.
What can sellers do to prepare for buyer scrutiny?
Address owner dependence and customer concentration, review operations and cybersecurity, and be ready to answer buyers’ questions with evidence.
How does Karen approach buy-side acquisitions?
She helps buyers define what they want to accomplish, assess whether a target fits that goal, and conduct due diligence before approaching targets.
Why might a business need more than two years to prepare for sale?
Changes to operations or customer concentration may take time to implement and show up in financial statements; buyers often want to review three years of financials.
What are “behind-the-meter” energy solutions for data centers?
On-site energy systems that reduce—but may not eliminate—the data center’s reliance on the power grid.
How does Karen use AI in her work?
She uses it to speed up tasks and analyze large amounts of data, while keeping human judgment central.
What lesson did Karen take from a job interview that ended in rejection?
She learned not to let other people’s assumptions define the limits of her career.
What does Karen want clients to expect from her firm?
Honest expectations, experienced guidance, and support through complex transactions while maintaining trust.

Transcript

Intro and Karen’s Background

Anthony Codispoti (00:01)

Let's do it, Karen.

Welcome to another edition of the Inspired Stories Podcast, where leaders share their experiences so we can learn from their successes and be inspired by how they've overcome adversity. As you listen today, let one idea shape what you do next. My name is Anthony Codispoti, and today's guest walked into a debold sales region running a negative 9% gross margin. Twelve months later, that same region was posting a positive 19%.

In another finance role years later, she cut a company's outstanding payables by 90% in just three months. Three decades in finance carried her from portfolio analysis at Chase Manhattan Private Bank to interim CFO assignments, ERP system rollouts, and corporate turnarounds. In April of 2022, after years of independent MA consulting work, she opened her own advisory firm. Karen K. Bennett is managing.

partner of Doyen Advisory Group, an MA advisory firm she runs out of the Atlanta metro area. She is a certified mergers and acquisitions advisor with an MBA in finance from Nova Southeast University. And she advises founders, investors, and boards on buy-side and sell side deals in the lower middle market, working across technology, high-tech manufacturing, SaaS, and professional services. But before we get into all that good stuff,

Today's episode is brought to you by my company, AddBack Benefits Agency. And if you advise business owners on their wealth, this is a lever most of your clients don't know they have. Here's the problem: your business owner clients are overspending on health insurance every year. That's money leaking out of the business that could be funding the very strategies you're building with them. But now there's a program from Bain Capital Insurance you can put in front of them that changes that.

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And they raise the value of the business itself. So your clients get stronger and more valuable, and you become the advisor who found the money and the one they tell their friends about. Learn more at AddBackBenefits.com. All right, back to our guest today, the managing partner of Doyen Advisory Group, Karen Bennett. Thanks for making the time to share your story today.

Why Karen Launched Doyenne Advisory Group

Karen Bennett, M&A Advisor (02:45)

Thanks for having me today, Anthony.

Anthony Codispoti (02:48)

So Karen, in 2011, you started doing M<unk>A advisory consulting on your own, and you were working with high-growth mid-market tech companies for over a decade before you formally launched the Doyen Advisory Group in April 2022. What made that the moment to get more formal, more organized with what you were doing?

Karen Bennett, M&A Advisor (03:09)

Absolutely. There came a point when I realized I was simply I wasn't simply doing individual consulting engagements anymore. I had developed a point of view about how MA should be approached, a methodology around preparation, execution, and a much clearer understanding of the clients I could serve best. At that point, continuing to operate simply as

Karen Bennett doing project work no longer reflected what I was actually building. So I wanted a firm, something with its own methodology, its own standards, and eventually a team and infrastructure that could exist beyond me personally. Doyen was really the transition from independent advisory work.

to intentionally building an advisory business. I stopped thinking only about the next engagement and started building the firm I wanted clients to be able to rely on long term.

Anthony Codispoti (04:20)

Okay, so tell us about what it was that you were seeing in the market, the gap that you wanted to fill, what it was that you wanted to do differently, the methodologies that you wanted to bring forth.

Karen Bennett, M&A Advisor (04:32)

What I kept seeing was a tremendous amount of attention paid to the transaction process what somebody had already decided to buy or sell. But some of the most important questions should have been asked much earlier. is the seller actually ready for buyer scrutiny? Is the buyer operationally prepared to absorb another company?

And what happens after closing?

Sometimes the transaction process becomes the first time those questions are seriously confronted, and that is too late. I wanted Doyen to operate further upstream to help clients think strategically about what they're trying to accomplish, identify vulnerabilities before they become transaction problems.

And prepare before the clock is running and leverage begins disappearing.

That's where M<unk>A readiness comes from. The transaction should be the result of preparation and strategy. It should not be the point where preparation begins.

Anthony Codispoti (05:53)

So what does that preparation look like and how early do you like to get involved with a company before they get to that transaction finish line?

Karen Bennett, M&A Advisor (06:06)

It depends on the client. So let's look at it from two different lenses. Let's look at it from the buyer's lens. The buyer could be a family office or a privately held company looking to do an acquisition. And that company is now asking the questions of what do I need in order for this transaction to be successful? And it is more than the actual transaction.

It's all of the preparation that they need to do ahead of time to ensure that they have the ability to absorb the new company that they're looking to acquire operationally, that they have the financing in place, that they have the team structure in place.

That's an example on the buy side. On the sell side, it's a completely different lens. The lens is: are you ready for scrutiny from the buyer? They're going to look at not just your finances, your operations, your people, your customers. How are you managing that?

How is it protected? What cybersecurity is in place, especially if you are in a tech industry business? and there's a great deal of scrutiny in there. That scrutiny you want to be prepared for. It will come. And the more you can answer those questions ahead of time and know the answers.

And even fix maybe some of the problems ahead of time, the better position you are in.

To be seen as attractive to the buyer and thus you have stronger negotiation leverage.

What Doyenne Does and Its AI/Energy Niche

Anthony Codispoti (07:59)

So Karen, it sounds like at Doyen, you guys are involved in a big chunk of this life cycle. Not just when the business is ready to go to market for sale, but all of this exit planning work that takes place in the months and years ahead of time. Maybe you can help lay out in your own words what Doyen does and who you do it for. Give us the full breadth of services.

Karen Bennett, M&A Advisor (08:29)

so our current focus is increasingly concentrated in AI infrastructure, alternative and behind the meter energy, technology enabled businesses, including AI, and SaaS, including AI enabled SaaS. so you know, the best client for Doyen isn't simply someone who wants to do a deal.

is someone who wants to do the right deal and be prepared to execute it well.

Anthony Codispoti (09:02)

So say more about that. Wha how was it that you found your niche here in this AI, SaaS, tech space?

Karen Bennett, M&A Advisor (09:10)

That's an evolution of my 25 plus years in technology and technology enabled businesses as well as in finance. so evolving into that AI space or that AI infrastructure as I refer to it was a natural evolution. It's not just something new and flashy for today. And

Combining the sectors, we're we're seeing a lot of overlap in those sectors.

So combining them and being knowledgeable about them was again an easy evolution for us because we already have come from that technology background and I specifically have have been around it for an extensive period of time.

Anthony Codispoti (10:03)

You obviously are working on the sell side. Do you also advise on the buy side as well?

Karen Bennett, M&A Advisor (10:09)

Yes, we do. That's actually where we concentrate the most. We concentrate very strongly on buy-side clients, so family offices and high growth companies. And we work with them through the life cycle of the company that they are growing. and saying, you know, also what's your end goal?

We want to know what your end goal because now we know what we're aiming for, and to ensure that the acquisitions that are made align with that end goal. And that then makes exit strategy so much cleaner because there's less work, less cleanup to do, less rearranging to do. It's already built in. It it's just part of the

entire environment of the company. On the sell side, that's a different story. Because we've often never worked with them before. They're coming to us new. They have often established businesses. Many owners have put their heart and soul and life of 15 to 25 years into the business. And they understand that business well.

What their n missing knowledge is how to exit it and exit it profitably. That's where we come in and say, Here's some expectations. Here let's do an analysis, see where you're at, see where the gaps are, and see how much time it would take to fill those gaps to.

adjust things to change things so that you're better aligned and more attractive to a buyer. Sellers, it depends on a lot of factors if they want to do it. I mean, Anthony, it could be a case of I'm talking to somebody who's 75 years old and they just don't have that kind of time and energy left. It could be you know

They're passing this on. It's a succession plan situation. So they're passing it on to the next generation. It could just be a number of years that they have in their head, I want to exit in two years, for example.

And I have to work within those constraints and try and get the best results I possibly can within those constraints. The more time I have, the better I can get them prepared for exit. The more constraints I have, it's not that I can't get them prepared, but I'm definitely not getting them.

The top dollar that they're they could be worth.

Value Levers: Owner Dependence and Customer Concentration

Anthony Codispoti (13:04)

What are some of those big levers that you like to pull for your clients, assuming that you've got a little bit of extra time before you go to market?

Karen Bennett, M&A Advisor (13:13)

So the first thing that we look at is going to be owner dependence. How much is that company dependent on you? The another one would be what I'm gonna call customer diversification. If and I've seen this where you know the revenue is great.

The EBITA is great. And then I look at the customer diversification and it's coming from two primary customers. And then I put my buyer's lens on and go, my, what happens if one of those customers falls off after transition? Now the value is not there anymore. The revenue is not there anymore.

The other one is going to be what I'm going to call a type of customer. So in the industry that I work in, there are often government contracts involved, whether that be at the state level or the federal level. And government contracts are lucrative, valuable. And you need to make sure that are transferable. And that relationship has been held entirely.

And managed entirely by the owner. A buyer's going to sit there and go, How do I get that transitioned over to me if I don't already have that relationship with that government entity? Who in my company is going to spearhead that and how are we going to transition that over? Because that government contract we find to be lucrative and we want that transferred over. Those are the kinds of questions that we ask.

sellers and say let's

Maneuver this in your benefit so that you're more attractive to a buyer. And because I spend so much time on a buyer's side, I know that lens well, I know that scrutiny well, and that includes valuations. If you're getting a valuation from and it's called a valuation assessment, often from or a value assessment.

From an exit planning company in a buyer's lens, I'm gonna disregard that.

Anthony Codispoti (15:35)

Yeah.

Karen Bennett, M&A Advisor (15:36)

But a certified valuation has more meaning, has more value to me.

Anthony Codispoti (15:42)

So the biggest things I'm

hearing are the owner dependency issue, right? Do you do you have that transition set up? Do you have a a leadership team in place where not everything is relying on that owner, as well as this issue of customer concentration, right? Is it a diversified customer portfolio? And if the answer to the both of those things are no, then it sounds like you've got quite a bit of work to do on the sell side.

Now, what's interesting for me here is almost everybody I talk to in this space focuses almost exclusively on the sell side. So you

Buy-Side Work and the Acquisition Thesis

Karen Bennett, M&A Advisor (16:13)

Mm-hmm.

Anthony Codispoti (16:13)

do buy side as well. And I'm curious to hear a little bit more about that work. For example, do your clients come to you and say, hey, we're looking for something in this space, go find us a deal? Do they already come with a target acquisition in mind? How does that relationship work?

Karen Bennett, M&A Advisor (16:33)

Actually, that's the majority of the time exactly how they do come to me. you know, hey, we've got this in mind. Hey, we want this specific target that we want to go after. And my job is to ask the question, why? And what I mean by why isn't to sit there and challenge them in a negative sense is to challenge them to answer the question of what are you trying to accomplish? What is the point?

In targeting that target. What is the point in doing the acquisition? What is that goal? And it you need to think that through. Have you thought that through? Is there an acquisition thesis? If there's no acquisition thesis, I encourage those buyers to come back to the table and think about that and say,

Instead of just throwing spaghetti on the wall and hoping it sticks, let's think through this. Let's plan. And one of my favorite quotes that I always put out there that's attributed to General Patton is those who fail to plan, plan to fail. It's not the plan, it's not stuck in stone. It's the ability to, I have thought through it. So when things change, I can easily adjust.

And still stick to the goal. And that's what buy-side readiness and acquisition thesis creation provides my buyers. Once we have that, now we sit there and say, okay, does that target still fit? And sometimes it does. And sometimes it doesn't. And that's an eye-opener when it doesn't. And now we sit there and say, okay, it doesn't. It's out.

What targets do fit? And now you're thinking through a clearer, more focused lens on the goal that you're trying to accomplish. And because you're thinking that way, you're now more aligned for a successful acquisition because you're already there in your judgment.

Anthony Codispoti (18:45)

So let's say that you've agreed that here's a target we have in mind, this makes sense, this fits the investment thesis, the acquisition thesis. What's your next move? you're going essentially to knock on the door of somebody who hasn't already raised their hand and said that we are interested in selling.

Karen Bennett, M&A Advisor (19:04)

Mm no. Our our next move is to do due diligence. And we're looking at everything that we can find about that company and saying, you know, does it still fit? Does it still fit? Does it still fit? And then we rank targets. And you depending on the bandwidth of the company, the buyer, we go after three to five targets. And yes, it then becomes a case of

reaching out, setting up meetings, having conversations with owners, CEOs, and taking them out to lunch sometimes and saying, where are you wanting to take your company? What does an exit look like for you? To understand their point of view.

And then moving that conversation to we have a client who's interested in you. And we often provide them a number at that point.

It's amazing how often that number is taken.

Anthony Codispoti (20:01)

Interesting. So how does that very first conversation happen? You're calling them up. I'm Karen Bennett from Doyen Advisory Group. I want to talk about buying your business? No, it's not that direct and straightforward

Karen Bennett, M&A Advisor (20:15)

Yeah.

Anthony Codispoti (20:16)

right away. What do you say in that first conversation, that first phone?

Karen Bennett, M&A Advisor (20:21)

It's more of a what I'll call a probing conversation. you know, we we are doing MA, we're not trying to hide that in any way or shape or form. often the the cli the the seller, the target will say to us, you know, is that what you're trying to call about? And some will hang up on us and others will take the call. It usually what I try and do on that call is can I take you to lunch?

And can we have a conversation about where you're at and where you're trying to go? Because I'm trying to figure out if the client that I have is a good buyer for you. And that is less threatening. It is more inviting to a conversation. And it gets them more willing to talk. It doesn't always work. It's it's a numbers game. And

Sometimes you have to do it two, three, four, five times. I did one last year. I hit on that target 15 times before I got a yes. and I got 15 no's beforehand. And I just kept going at it because they they were such a good fit for my buyer client.

Y you gotta be polite, but you gotta be persistent and um yeah.

Anthony Codispoti (21:33)

Persistence. Polite persistence. I like it.

Karen Bennett, M&A Advisor (21:40)

It it's it's a uh fine line though between annoying and persistence. And sometimes you just gotta be annoying.

Anthony Codispoti (21:49)

so I understand, Karen, that Doyen is currently refining its focus around a smaller set

Karen Bennett, M&A Advisor (21:55)

Mm-hmm.

Anthony Codispoti (21:55)

of advisory services, defined industry verticals that you mentioned before. What's driving this shift now?

Karen Bennett, M&A Advisor (22:03)

Focus is driving that shift. As an advisory firm grows, there is always a temptation to say, we can do all of these things for all of these companies. But I think expertise becomes much more valuable when you become disciplined about where you can genuinely add value the most.

We have chosen to concentrate around MA readiness for both buy and sell side, buy-side strategy and transition work, and selective sell-side strategic transitions. We're doing the same thing with sectors. So again, I've spent roughly 25 years around technology and technology-enabled businesses. So SaaS.

AI enabled businesses and AI infrastructure are a natural evolution of that history. The energy component is increasingly important because AI infrastructure doesn't exist in a vacuum. you know, data centers they need enormous amounts of power. And that creates opportunity around alternative energy, behind the meter solutions, engineering, infrastructure, and the other businesses that support.

That ecosystem. So, this isn't not about chasing whatever sector is fashionable this year. this isn't a runaway show. It's about concentrating on our expertise and our experience around areas where we see long-term strategic activity and where we can build deeper expertise and stronger professional ecosystems.

The point is I would really rather be highly relevant in a defined market, Anthony, than broadly visible in a market where we have no real differentiation.

Anthony Codispoti (24:01)

Riches and niches, right?

Karen Bennett, M&A Advisor (24:03)

Riches and niches, that's exactly it.

Behind-the-Meter Energy and AI Infrastructure

Anthony Codispoti (24:07)

So you've used this phrase a couple of times that I've not heard before, behind the meter solutions. What does that mean?

Karen Bennett, M&A Advisor (24:14)

Solutions are energy solutions for data centers that do not pull from the power grid. So I guess the best way for everyday people to think about it is it's a mini

energy generation plant or system that the data center utilizes to power the data center itself without pulling any energy from the grid. Now they still end up pulling some energy from the grid, but it can save them anywhere from 40 to 80 percent of pulling energy. So that's 40-80% less energy pulling from the grid. And that's a hot

topic right now so you can understand why that is becoming a real solution for the data centers. It brings up some other issues, but it's dealing with that one singular problem.

Anthony Codispoti (25:16)

So what would be an example setting up a solar farm next door to the data center?

Karen Bennett, M&A Advisor (25:23)

More setting up a solar farm on top of the data center and the roof would be a better example. another one would be literally it's what they call these micronuclear, and that's often that's sometimes being used. There's other alternative energy

what I'll call micro plants that are put, that's what we call behind the meter, micro plants that are put on these data center sites. And usually you see those next to the data center. So like in what was the parking lot.

Anthony Codispoti (25:54)

a wind turbine or something.

Karen Bennett, M&A Advisor (25:56)

They don't use wind turbines, but that's the concept, yes.

Anthony Codispoti (25:59)

What might they use? So we've got solar panels on the roof, we've got the micronuclear, which I know a lot of people are really excited about.

Those

the two big categories or we have others that we're really

Karen Bennett, M&A Advisor (26:11)

The other ones are,

if you want to think about it, it it's basically really big generators. So you see them in the hospitals. All hospitals have to have them in case you know, the grid goes down that especially the ER and operating rooms and things like that can continue to function and their freezers can s can stay frozen and things along those lines. And y they're huge generators. They're often gas powered, they're

diesel powered i is really the the fuel that they use. So you're seeing a lot of that as well. And it again creates another problem.

But it's helping manage some of the d data centers demand for energy.

Anthony Codispoti (26:58)

Gotcha. You also talk about working in AI infrastructure. Are we talking about the data centers then? Or are we talking about software kind of infrastructure? What what do we mean by that?

Karen Bennett, M&A Advisor (27:09)

So when I say infrastructure, it's the picks and the axes, you know, to the gold mine. it's the engineering firms, it's the it could be even construction firms, it's the services that the data center needs in order to continue to operate. So behind the meter, energy source may be actually owned by a different company and it's physically sitting on their

property but they don't themselves maybe own it. it can also mean software as far as what I'll call the AI integrated software. Those are the types of clients that we work with.

Anthony Codispoti (27:51)

as I look as an outsider here, the decision to go into this niche makes a ton of sense. There is not a space that's hotter than what you're describing right now. I'm curious though, how much of the decision was, ooh, this is what's hot versus, ooh, this is what we're already good in. you've already been around that space and been involved in.

Karen Bennett, M&A Advisor (28:13)

Yes, absolutely. And I've talked about this a few times. You know, again, I've been in technology and around technology clients for over twenty-five years. It was a very natural evolution to go into the AI space. Now that space wasn't open but recently because that space has exploded and all the infrastructure that supports it has exploded. so that move

was very natural for us because we were already connected to it. It wasn't again, this is new as hattest thing, let's go after it. It's we have deep-seated knowledge, deep-seated understanding, including in regards to cybersecurity, because that's one of those due diligence questions that we ask, especially the buyer comes from, it it's just constant cybersecurity questions related.

To make sure, you know, that what they're buying, of course, retains that value. So we've been doing this for years. I started doing this around tech security and what then had had evolved into cybersecurity starting back in twenty twelve. so it's it's been a few years.

What a Two-Year Exit Plan Looks Like

Anthony Codispoti (29:31)

Yeah, you've got a strong footing here already. let's say that I'm a business owner. I'm in one of the niches that, you know, we're talking about here, the AI, the energy, et cetera, that you work in. And I come to you and I say, Hey, I think I want to sell my business in a couple of years. Let's work together. Walk me through what those couple of years look like from the start of the engagement. What is it that our conversations entail? What is it that you're walking me through?

Karen Bennett, M&A Advisor (30:02)

My first response to that is, you know, two years is a is a good number to start with. It gives us information that tells me where you're coming from. What we're asking is is two years enough? Again, and I've already hit on this.

Two years of just might might be because I'm dealing with a seventy five year old. It might be because I just I wanna retire or I I need to pass this on to the next generation. Or it's just a number in their head.

I need to work with within those reasonable constraints, specifically if I'm dealing with somebody who is older. And I also am trying to do what is best for the company. And when we have a client like that, we kind of test their limits. We're trying to see where they're willing to give and what they're willing to do and what they're not willing to give and not willing to do.

Because inevitably a lot of these businesses that are selling are owner dependent. And that is one of the first things that we want to try and change. And we see it. But somebody who's 75 is likely not going to give us the time to do it.

And so we have to try and structure the

the readiness and ultimately the sales transaction of of that company around those constraints.

If the client just has that number of two years in their head, I sit there and say, Okay, let's have a conversation about that. Because they're now more I can move them more. And they can understand and they also have more time.

The client

Could say to me two years, and we sit down and say, okay, let's get some expectations straight. And one of those expectations is that buyers expect to see three years of financial statements. And what they're looking for is not just the numbers, but they're also going to look at your operations, how you're operating for the last three years.

Is that attractive to that buyer? Is the question. And in our assessment, if we sit there and say, if we make these changes, let's just say customer concentration and owner dependence, and we put in a C-suite, we diversify those customers more. we structure the data of the customers better and protect it better because.

we've got to protect that data and ensure that it is owned by us. And if it's not owned by us, who? we've got to answer all those questions for the buyers. Once we make those changes, now we need to implement them. And implementation can take a year or so. And now you need the implementation to flow through and show up.

in those financial statements.

So it could be four years. It could be five years. And if they don't have as many constraints, I can get a much higher valuation out of for them. If they have the constraints, I work within that as much as I can to increase the valuation as much as I possibly can.

So when that they're going to market to a buyer, they're getting the top dollar in that moment of where they're at that day from that buyer.

Anthony Codispoti (34:03)

So I hear what you're saying. I I come to you with two years in mind. You're like, hey, can can we do three? Can we do four years? Because I've got a bunch of ideas on ways that we can make changes in the company that are going to improve that that offer that we get. It's going improve the valuation of the company. But we're going to need time to implement these. We're going to need 12 months, say, to implement

Karen Bennett, M&A Advisor (34:24)

Mm-hmm. Yeah.

Anthony Codispoti (34:27)

these. And then we want

Ideally, if we can have it, three years of operating history with those changes in place, because like you're saying, Karen, they're gonna want to see three years of financial statements and tax returns with all of those changes having propagated through the system.

Karen Bennett, M&A Advisor (34:44)

Exactly. And you want as a seller, and remember, I I spent a lot of time on the buy side, so I know that buyer's lens. So when I switch over to seller, I'm bringing all that knowledge with me. As a seller, you want to make sure that the company and the information that you are giving to that buyer is sh not is showing the buyer the actual evidence.

Of your actions and the changes that you have made, the improvements that you have made, and that it had actually worked continuously. You don't want the buyer to sit there and go, well, you just did this six months ago. But is it gonna continue when I buy the company and this transition's over? Can I count on it? I haven't seen enough.

That makes me feel comfortable with that. And that's where buyers come from. So, like I said, I bring that to the seller and say, Let's beef this up. Let's make this real. Let's substantiate this. And then let's present it to the buyer so that you were presented to the buyer in the best possible way. So that you can get every dollar off the table that you deserve for your company that day.

Anthony Codispoti (36:05)

Tell me what's behind the name Doyen Advisory Group, D O Y E N N E.

Karen Bennett, M&A Advisor (36:12)

So that's one of the things actually that's going to change likely into the next year. But as of right now, the reason I chose Doyen is because that is a French word. the male version is D-O-I-E-N. And it means a person that has had years of experience and expertise that they're bringing to the table, and they've become a forefront thought leader in their space.

Anthony Codispoti (36:39)

That seems like an accurate description of you. You were a thought leader in this space. Yeah.

Karen Bennett, M&A Advisor (36:45)

And that is what we're putting out there more and more. and where some of that shift has also come into to ensure that we're more focused. 'cause that's something else a a a doyen or doyen will do. like I said, it it's both male and female.

Why Clients Choose Doyenne: Honesty and Trust

Anthony Codispoti (37:02)

Hmm. So tell me a little bit more about what separates Doyenne's approach from other advisory firms in the lower middle market. I guess to ask the question in a slightly different way, when clients choose to work with you, Karen, they've had lots of choices. Why do they ultimately decide to go with you?

Karen Bennett, M&A Advisor (37:25)

I would say there's a couple of reasons. one of the first reasons I would give is that they're dealing with senior level MA.

expertise at my firm and often you'll find this in boutique firms

You're not dealing with the analysts. Your daily interactions aren't with an analyst or somebody lower on the totem pole. Your interactions are with me. So you're getting the expert judgment of somebody that has been doing this for years, that has deep seated knowledge in the industry sectors and is bringing it to your table. I would say that's the first reason.

The second reason is surprisingly the fact that we are very upfront about expectations, about process, and about results. Which means I'm never going to tell a client, whether it's a like a buyer, I'm never gonna say that buyer, hey, we're gonna get that company really cheap for you.

I'm never going to tell a seller what they want to hear is, you know, we're going to sell that company for a hundred million when I know it's never going to pass the twenty-five million month.

I will never tell a client but they want to hear just to make them feel good.

Even if that's uncomfortable, even if that impacts the transaction, even if that costs me the fee.

Anthony Codispoti (39:11)

I gotta tell you, I respect that. As somebody who's been through a number of exits, I've worked with some folks that were very upfront, very straight with me. And I've interacted with some folks that yeah, they were telling the seller what they thought they wanted to hear, giving fantastical valuation projections that just had no basis in reality. And so, you know, it it it steals a lot of

trust and comfort away when you're you're dealing with that and it seems like y you take the opposite approach, Karen.

Karen Bennett, M&A Advisor (39:42)

So you just hit on the word that's very key to us here and is something that is a hard line for me, and that is trust. Trust is hard to earn and easily lost. And when somebody is trusting us with consequential transactions.

It we lose trust in doing that.

That's terrible for the client all day long. You just talked about it. I'm certain you can say that the ones who were up front, you had better experiences, it was likely a cleaner process, and you knew what to expect. The ones that sugarcoated things and gave you the sales song and dance, if you went with them, ended up actually harming you.

And possibly costing you actual money that was actually there on the table because they're so busy with the song and dance that they're not paying attention. We pay attention, we pay attention to those details, we set up that plan, we set up an assessment, we walk through it. Does this make sense? What does that look like? And from a self side, that assessment becomes action.

If the company needs to make any changes, the company makes those changes, shows up in the financials, makes them obviously operate better. Now they are more attractive to a buyer and they have more negotiating leverage at the table, which is what I'm after for them. And they're in a better financial position at the end. And we have kept that trust.

From the beginning and throughout I would rather lose a client.

Who would prefer me to do the song and dance, lose that fee, then lose the trust.

Anthony Codispoti (41:50)

Let's give our listeners a case study, a particular client example where maybe you had something unusual during the close process that you had to deal with. Maybe it was good, maybe it was bad, maybe it was a deal that almost fell apart at the finish line. Walk us through what was going on and how you resolved it.

Karen Bennett, M&A Advisor (42:11)

So I'm very limited in that I cannot provide actual examples. what I can do is give you the composites of examples and issues that we see repeatedly. On the and they're different from the buy side and the sell side's point of view, but at the table they become everybody's issues.

So let's talk about from the buy side point of view. a problem that will cut that does not come up with my clients, but if I've been on the sell side, I've seen this with buyers, is they have not identified the staff that the seller has in their company that will be kept. They have not put together.

contract agreements for that staff, they've not thought about comp compensation. They've not thought really about who's staying and who's going. It's just a number. We're gonna decrease staff by 80% or whatever. But they don't think about the knowledge that is walking out that door if one, even if one key person

goes with that knowledge. And you see it more after the the the deal with the buyers if they fail to do that.

It's detrimental to the buyer because often what they're buying might actually walk out the door with the people. So on our side, when we're working with buyers, that is one of the things that we go through very specifically and we identify and we make sure contracts are set are ready to go. We make sure we know what that transition is going to actually look like after the deal.

And I negotiate that and have all of that as part of the closing because for the buyer, closing isn't where the deal stops, it's where ownership begins.

Now let's switch hats and go to the seller side.

The seller, the big one that I see with the seller is, and of course, this doesn't happen with my clients because I actually will not go to the table with a client who's in this position, is that they will just come to the table with a business attorney. And I've seen this from a buy side all the time. you know, when I'm sitting on the buy side in the seller, it's got just a business attorney.

Or maybe their regular tax accountant. And from a buyer's side, I know that they're gonna leave money on the table.

Anthony Codispoti (45:02)

Just because they lack experience

Karen Bennett, M&A Advisor (45:02)

Because they don't

Anthony Codispoti (45:04)

in what's going on?

Karen Bennett, M&A Advisor (45:05)

Because they don't have the team around them that they actually need to adequately negotiate this deal and get every dollar off that table that they deserve as a seller. So as a buyer, I use that to my advantage. From a sell side now, because again, I sit on the buy side, I know the games. With my plants, I'm sitting there saying, Yeah, we're not going to the table like that. That's not acceptable. We're bringing a

With me, I bring in the specialists that are needed. An MA attorney. And when I say MA attorney, I mean one that specializes it and eats and breathes MA legal work all day long. A MA-focused tax accountant because that transaction has very specific tax implications that the business has never experienced before, and the person, the owner, has never experienced before.

It only happens at that time. I also bring in to that table, or I I should say all of this is actually happening before we get to the table, is a wealth manager. Because there is a liquidity event that is taking place. And what is done with that money, how much of the Uncle Sam gets versus you.

Is often dependent upon what a wealth advantage can set up. I don't do those things, but I bring those people to the table and say, let's get this set up. So when we get to the table, that MA attorney, that tax accountant, that MA tax accountant, and I are now across the buyer who has an MA attorney, an MA tax accountant, an MA advisor.

So it's now equal instead of very unequal.

Using AI as a Tool, With Human Judgment

Anthony Codispoti (47:06)

Talk to me about how you're using AI in your work, if at all.

Karen Bennett, M&A Advisor (47:12)

use AI as a

And as a tool. A tool that allows us to do things a bit faster, analyze things quicker, especially huge batches of data. and it even helps us ask better questions.

However, there's a difference between tasks and judgment. AI helps us with the tasks.

However, I still have to sit there and say, okay, you've given me a better question, but is that the right question to ask at this point?

Is that the right question? Does that need to be refined? And then the answer that I get, does it make sense in the context of what it is we're trying, you know, to discover?

That's a difference between task and judgment. AI helps us with some tasks, not all, but some. And helps us do it a bit faster, a bit more refined. However, we retain the judgment aspect. As humans, I think that that's where we need to stay when it comes to working with AI. That is my stance on it. We maintain the judgment and AI helps us with heavy tasks.

Anthony Codispoti (48:39)

That's very similar to how I think about it. It's like a great brainstorming partner who is

Karen Bennett, M&A Advisor (48:45)

Mm-hmm.

Anthony Codispoti (48:45)

a junior employee that kind of understands

Karen Bennett, M&A Advisor (48:47)

Mm-hmm.

Anthony Codispoti (48:48)

what I do, but not a hundred percent, and is really good at right, here is a pile of things, here is a long document I want you to review and you know and come back to me. Here's a set of tasks I want you to go do and come back to me. But at the end of the day, if I just take

exactly what it gives me and spit it back out into the world, I got an egg on my face. Like it's not

Karen Bennett, M&A Advisor (49:11)

Yeah.

Anthony Codispoti (49:12)

it's not replacing me and I I'm gonna guess you're you're thinking there's not a risk of it replacing you anytime soon either.

Karen Bennett, M&A Advisor (49:21)

Again, so the egg on the face part, I like that. because that is happening. We're seeing that in our MA space. We're seeing it in the legal space, time and time and time again. And in our firm, I am very that's a hard line. It's not that you can't use AI. And I see AI more as not the junior analyst that doesn't know what they're doing.

But the the analyst that actually does understand and knows what they're doing, but they don't have the judgment that comes with human experience. And to put it in context with with everything that we're doing, the complexity part of it. That's where I feel we humans do better. those repetitive tasks and things like that that you know we're,

we all fall asleep doing that's where AI does better. specifically, let's talk about the question that you just asked Anthony about how it's impacting us and that whole fear of replacement. Because that's a real fear out there. And it's a legitimate fear. In my world, I have very few analysts that I actually work with, human analysts that I work with. That is down

From the huge number we used to have. It's impacting a younger generation. And what that will look like in twenty years, I can't tell you. What I can tell you is I think it is

Unadvisable for anyone in this space to think that technology is not changing what we do, it is absolutely having an impact on us. The impact, however, I think is a positive one. Why should a client have to pay premium prices for analytical work that can be done by a computer?

In an nth of the time. And so it's healthy for that to be there. I also think it is healthy because it is forcing us to be better in our experience, our expertise, knowledge, and our judgment. And I think that's going to be the line where that differentiating line in most services where.

It's not what you're delivering, it's how thorough the judgment behind what you delivered is.

Her Hardest Lesson: The Goldman Sachs Interview

Anthony Codispoti (52:03)

So I want to shift gears on you now, Karen. In my experience, some of our greatest lessons come from the most uncomfortable times during our lives. What is one of the hardest things that you've had to overcome and what did going through that teach you?

Karen Bennett, M&A Advisor (52:28)

there there are experiences in my life that I choose to keep personal. So I probably publicly wouldn't like try and rank any of them or bring up a lot of them. There is one professional experience I had a sick that did have a significant effect on me.

shortly after I earned my MBA, I was flown up to New York for an interview with Goldman Sachs. I was so excited. I was on Newlywed as well. And during that interview, the interview noticed my wedding ring. And of course, I'm happily talking about how I just got married and I just graduated. I mean I'm and I'm here at Goldman Sachs. I'm so excited that my you know, the world is open. Everything's possible.

And I'm in that mindset. And he tells me, You just got married. You're gonna have a bunch of babies. I can't hire you.

At the time it was devastating.

But experiences like that eventually taught me something important. Other people will sometimes make decisions about your future based on their assumptions about who you are and what they think you're going to do. And you cannot always control that. What you can't control is whether you allow somebody else's assumptions to define the boundaries of your career.

My career ended up taking a very different path than the one I imagined that day and that interview.

But ultimately it became my own.

Anthony Codispoti (54:18)

So

This one door closes, but it ends up opening up all these other doors that takes you on a different path than what you were first imagining.

Karen Bennett, M&A Advisor (54:30)

Yes.

Anthony Codispoti (54:31)

I'm curious how long it took before you stopped feeling angry or bitter about that experience.

I think for a lot of folks, myself included, when I go through something like that, it's like it's not until I've I've got a lot of distance and I can look back in the rear view mirror and I can say, my life is measurably better because I went this way instead of that way. So you know what? I'm actually kind of

Karen Bennett, M&A Advisor (54:59)

Yeah.

Anthony Codispoti (55:00)

grateful that that happened. But it take for me anyways, it takes time. What about for you?

Karen Bennett, M&A Advisor (55:07)

Anthony, I I think you're correct. But I am also gonna say I don't think that the anger, the disappointment, the rejection, that that horrible feeling of rejection, especially at that pivotal time in my life, because that was that was a very substantial time in my life. I don't think that ever goes away. A matter of fact, I think it's still there. And when I remember it, it still hurts. And I think that that's okay.

Because the pain tells me something. The pain tells me that I didn't like something. That wasn't what I wanted. Now, how do I go and get what I want? So I can't go through that door. What door can I go through? Time has given me the ability to, and this comes with.

Getting older, which we don't want to talk about. But the positive of it, they say you get wiser as you get older. What it is is I think that you look back on things and either they weren't really as big of a deal in the end, or you look back on it with gratitude. I look back on that experience with gratitude. Now I definitely didn't.

And it still hurts when I think about it. And I'm grateful for that. Because that pain taught me lessons.

Anthony Codispoti (56:38)

Mm. I appreciate that honesty. As you think about the work that you're doing now, Karen, what is it that you most want to be remembered for?

Karen Bennett, M&A Advisor (56:51)

I think the focus is gonna be on

A few things.

From a business sense, I want us to be seen as the advisory advisory partner that ensures clients get through consequential and often complex transactions.

that meets their intended goal. And often that means profitable. It also means other things. it could mean, for example, like legacy or investment intention, things along those lines.

I wanna be the known as the person that helped them.

Make that happen, Get the win, as they say.

Personally,

Well, it may be even professionally. I guess I want to be remembered as a person who held to her standards, earned trust, and was respected in the industry as well as respected by the clients that she had meaningful impact on.

Anthony Codispoti (58:21)

Karen, before I ask my last question for you, I would like to do three quick things for the audience. First of all,

Karen Bennett, M&A Advisor (58:27)

Sure.

Anthony Codispoti (58:28)

anybody that wants to get in touch with Karen Bennett, go to her website, doyenneadvisorygroup.com. doyenneadvisorygroup.com. It'll be in the show notes, but it's doyenneadvisorygroup.com.

And if you're enjoying the show today, please take a moment to subscribe wherever you're listening. It also sends a signal that helps others discover our podcasts. So thank you for taking a quick moment to do that.

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So last question for you, Kenneth Karen, a year from now, what is one very specific thing that you hope to be celebrating?

Karen Bennett, M&A Advisor (59:38)

interesting. I guess right now, because we are going through the focus switch in the organization. And that focus switch is both on the services that we offer and the sectors that we service, is being seen as that thought leader in those spaces. And people coming to us and saying,

We would like your insights and thoughts because you're so embedded in what's going on. and our point of view is not from a political point of view, a governance point of view or anything along those lines. It's from a business impact point of view. What is the impact to the company? What is the impact to the value? What is the impact to the customers?

What is the impact to the people? And that's where we sit and being seen as the thought leader in those spaces are exactly where we want to be.

Anthony Codispoti (1:00:39)

Love it. Karen Bennett from Doyen Advisory Group, I want to be the first to thank you for sharing both your time and your story with us today. Really appreciate you being here.

Karen Bennett, M&A Advisor (1:00:46)

Anthony,

thank you so much for having me. I really appreciated it.

Anthony Codispoti (1:00:51)

Hey folks, that's a wrap on another episode of the Inspired Stories Podcast. Thanks for learning with us. And if one thing stood out, put that into action today.

Connect with Karen Bennett:

Website: Doyenneadvisorygroup.com