Buyer's Frenzy
What really kills a deal - before diligence even starts?
Buyers’ Frenzy is the podcast for founders, family business leaders, and the advisors who guide them through the emotional, financial, and leadership complexity of selling a business.
Each episode unpacks one of the hidden performance risks that silently erode value - from leadership missteps and buyer psychology to outdated metrics and team misalignment. Hosted by Will Lindstrom, this series brings together experts in exit planning, valuation, and performance analytics to reveal what drives enterprise value - and what quietly destroys it.
If you're looking to avoid the deal killers most people miss, Buyers’ Frenzy gives you the clarity, confidence, and tools to turn your business into a showcase - not a stress test.
Buyer's Frenzy
The $0 Business Test - Can Your Company Run Without You?
What happens when you’re the biggest asset in your business - and the biggest liability to its sale value?
In this episode of Buyers’ Frenzy, host Will Lindstrom sits down with exit planning advisor and business coach Len Breskowitz to unpack one of the most common- and costly - deal killers: owner dependency.
Len explains why a business that can’t run without its owner is essentially worth nothing to a buyer, and how his “two-week vacation test” quickly reveals the level of risk.
They discuss practical ways to reduce that dependency, including Len’s “80% rule” for delegation, step-by-step approaches to building owner independence, and the critical importance of defining your “next big adventure” beyond business ownership.
The conversation also covers the emotional and strategic sides of letting go, the surprising gap between owner expectations and family succession reality (50% vs. 25%), and why early, open conversations with family - ideally three to five years before a transition - can prevent valuation surprises and conflict.
Len also shares a simple way to explain valuation and risk to family members so everyone understands their role in protecting and increasing enterprise value.
Highlights Covered:
- Why buyers avoid businesses tied too closely to their owner
- The “two-week vacation” litmus test for sale readiness
- How the 80% rule helps owners delegate effectively and reduce dependency
- The emotional side of letting go and owner identity after a sale
- Why early family conversations (3–5 years in advance) prevent exit surprises
- The gap between owner expectations and reality in family succession (50% vs. 25%)
- Building an advisory team to guide the exit process
- Explaining valuation and risk in simple, relatable terms
Whether you’re years from selling or actively preparing for an exit, this episode shows why your ability to step away may be the single best indicator of your company’s value.
Have insights on “Deal Killers”? If you’re a CEPA, CPWA, CFP, or fiduciary with experience navigating the hidden risks that derail deals, we’d love to hear from you. Connect with us on LinkedIn or at theculturethinktank.com/contact
Today I am pleased to welcome Len Breskowitz. Len is a certified exit planning advisor and Focal Point business coach in Boston. He grew up above his family's small business, which set his professional trajectory and love for small to mid-sized businesses. Len has played key roles, leading FP&A and launching QuickBase at Intuit to scaling Constant Contact's partner network from 50,000 to over half a million users. He's played critical roles at Grasshopper, repsplee and Nextiva. Today Len helps small owners business owners, especially those nearing transition maximize value and prepare for life after business. And so with that, len and I today are going to talk about company-specific risk premiums and all the implications that goes into that. But before we jump into that, I'd like to let Len introduce himself and a little bit more about his background.
Len Bruskiewitz:Thank you, William. It's great to be here. I appreciate the invite. You hit on some of the high points. I literally grew up above a small business that was a 24-7. I learned the ins and outs of what it took to run a small business and then my entire corporate professional career was focused on serving small businesses as customers. That's what I live and breathe. I decided to leave corporate a couple years ago and got into coaching small business coaching, as you might imagine and then really started to focus on that kind of getting business owners and their companies ready to transition out of. It's been kind of a lifelong of experiences getting here, but there's a huge need for what I do and get a ton of satisfaction out of helping business owners get ready.
William Lindstrom:Now, that's great and I know you and I have talked before and deal killers are always one of those things that you try to teach business owners how to avoid. Lately there's been a growing sense of transactions happening, but the sense that the leader is the business and people trying to challenge the valuation of business. How do you avoid that? And, ultimately, what are the deal killers that are associated with people's perspective of the leader that's trying to exit or trying to sell the company?
Len Bruskiewitz:There's a bit of a double-edged sword here, because in order to have a great small business, you need a great leader, you need a great owner who sets the vision and implements things and makes sure that the business is growing and taking care of clients and all those kinds of good things. The other side of the sword is that the business, in order to be saleable and to be valuable, has to be able to operate without that owner. Because ultimately, if you're thinking about a small business that somebody is interested in acquiring, they don't want to acquire the owner. Right, the owner is riding off into the sunset, so that business needs to operate effectively without that owner there.
Len Bruskiewitz:That's a big piece, a big deal killer. You can see it happen is when a potential buyer comes in and says so, mr or Ms Owner, what do you do in the business? And if the answer is I do everything, the potential buyer heads for the exit. So it's really got to be. And if the answer is, I do everything, the potential buyer heads for the exit. So it's really got to be important that the owners can the business can operate without the owner there in order for it to be saleable.
William Lindstrom:How do you start that process? Because I know, like you know, owners hold real tight. You know I'm an entrepreneur, so I hold. I know I hold on too tight. How do you get them to recognize they need to let go? Because that was. I just came from this really interesting exit planning Institute conference, or a little chapter session, and all they did was talk about the whole issue with leadership, risk and transition and it being the business. But how do you get them to recognize it? Cause that was always that seemed to be the conflict.
Len Bruskiewitz:One of the ways I do that is a pretty extreme example and it's meant for a little bit of shock value. To be honest with you is I basically say if you need to make every decision, if the business falls apart without you there, your business is worth $0, right? Literally nobody wants to buy you, mr or Ms business business owner, so that's a bit of a shot to the system that works. I then turn to maybe some some softer gloves, some softer kid gloves, and say look, don't you want to be able to de-stress, don't you want to be able to take more time away from the office and make more money and grow people? Those are the positive benefits that come from letting go. There's a little bit of carrot, there's a little bit of stick and hopefully between those two, the business owner starts to realize that in order for this thing to be worth something, they've got to let go.
William Lindstrom:That's interesting. To the carrot and the stick. Do you have any specific questions? Because I know, for example, at this little conference talking about exit valuation and the whole concept of company-specific risk premium, they were always looking at the leader has all the relationships with the suppliers, the leader has all the relationship with the vendors, and then on the flip side they're saying but the leader doesn't, or the owner doesn't know that or doesn't recognize that, Is there any way you can help? Or how do you think about helping the leader get that or become aware of that issue? Because it seems like they got blind spots.
Len Bruskiewitz:I have this kind of litmus test that I've shared with you. I call it a simple question Can you take a two-week vacation from your business without your phone, without your laptop? What will your business be like when you get back On its surface? A pretty simple question, but it really delves into the kinds of things you're talking about. It's a simple way to describe owner risk premium.
Len Bruskiewitz:It's impossible to put an analytical answer to a business owner. What I do is I gauge their reaction and if they have a look of horror on their face to say, oh my God, I can't leave for a day, then I know that the risk premium based on the owner is very high. If they look at me and say, yeah, did it last quarter, Not a problem, Everything's fine, I know then that they've got that separation. It's kind of based on the reaction. Then there's some in between, like well, probably a couple of days, but maybe not too. You know what I mean. So the gradations within. But the answer to that question gives me a pretty good idea of whether this thing can operate independently or not.
William Lindstrom:And so if they do say, you know, oh my God, I cannot take, I can't do it, I can't, I can't step away, you know, as a you know come from the exit planning and the coaching perspective, how do you begin the process for them to get them to do that and to get them to position the company to be a company and not a reflection of their personality?
Len Bruskiewitz:What I do is assure them that I'm not going to ask them to completely let go of everything on day one. So I think there's a panic around that where you say you need to become independent and they say, well, ok, and I'll tell you why. A there are a lot of business owners. Identity is wrapped up in their company, so the idea that they're no longer needed or no longer important is goes way beyond the analytical and really hits at the emotional level. One piece is I say this isn't going to happen overnight, but the way that I get them moving is I try and get them to invoke the 80% rule, and the 80% rule is delegate some task, and that could be to your staff, it could be to a virtual assistant, whoever it is.
Len Bruskiewitz:Delegate some task, and that could be to your staff. That could be to a virtual assistant, whoever it is. Delegate a task to somebody and let them do it, and the 80% part comes in. If they can do the job 80% as good as you can, let it go. There's a whole thing of nobody can do it as well as I can. That may be or may not be true, to be honest with you, but the whole idea is that if you can get something low value off your plate and let somebody else do it, it's a huge win on a few fronts. One you're enabling your staff if it's your staff to get better and take on responsibility, but you're also de-stressing yourself. That's how I come at this is there's an emotional piece to it, but there's also just we're going to do this step by step, and once you've done one, then you build a little confidence that you can take on the next one.
William Lindstrom:You know you brought up a really interesting thing that I've heard from other people that I've talked to, particularly in the wealth management space, is the importance of identity and that if the identity is too strongly associated with the owner and founder of the leader, with the company, they can't let go and oftentimes they don't know what they're going to do afterwards. They're like getting family pressure to sell or they've got. How do you help them find that?
Len Bruskiewitz:offering identity. Wise, it's super important. And there's a part of you might ask me at some point hey, what? What should somebody do now? Right, what should if they're faced with this? And one of the components there are four components components I talked about. I'm going to fixate on one.
Len Bruskiewitz:To answer your question is the personal side, right, a big thing that a business owner needs to do is define what their next big adventure is. I'll give you the negative example. If a potential buyer comes in, sits down with a business owner and says what are you going to do when you sell? And that business owner says something like, oh, I'm going to play golf or I'm going to travel Bad answer, that's not a plan, right? You need a plan that is going to occupy your time and give you that identity. That could be hey, I'm going to start a nonprofit or volunteer, I'm going to teach something or I'm going to have some activity.
Len Bruskiewitz:Having the next adventure is a big piece of it. The second big piece is to discuss that with your family, right, so that your family is on board with what your plan is. But that solves a bunch of problems. One is they know they have some input. The other piece is. It really decreases the likelihood of miscommunication if there's a potential succession plan in place. A lot of business owners about half of them think that their family member they're typically their kids are going to take over the business. That only happens about 25% of the time, so there's a big gap there. What is that gap? It's a communication gap, right, it's because the elder and the younger generations were afraid to talk about it. Then you get into these awful situations where nobody's clear on what's happened. That's one component that I really tend to focus on is know what you're going to do next.
William Lindstrom:That's fascinating, especially around the, because I didn't know the statistic of like 50 percent want to pass it on to legacy and only 25 percent wanted. Running down that vein, how important is it to bring the family into the pre-due diligence, the consideration like how early do you bring them in? How do you bring them in without being a family counselor? How do you bring them into the process where you start to get that clarity? Because I think, de-risking the business if the leader's holding on too tight or the owner's holding on too tight because they think they're going to transition to the next generation, it might change the perspective of okay, I need to let go now because I won't be able to step back in, or I'm not going to step back in because obviously I've just sold the company.
Len Bruskiewitz:It's really dependent on the family situation. Normally, what my recommendations are as early as possible, just to float things and when I talk about exit plan, it's not a six-month process, right, I'm typically talking about three to five years in advance Sitting down with family members and saying here's what I'm thinking, and get everybody's opinions on the table before you make a decision. That gets to the point of is there a family member who's raising their hand and saying I am interested or are there not right? So you just starting that earlier rather than later is really important, because what you don't want to end up with is a situation where you think a family member is interested and then they turn out not to be, and now you're stuck.
Len Bruskiewitz:Or you start the process of selling to a third party and all of a sudden a family member chimes in and says wait a minute, I'm interested. So having those conversations really early and having them be not set in stone is a huge way to do that, and it ties in with what I talked about earlier, which is to say I, as the business owner, here is my plan, this is what I want to do next and on what timeframe. And then that helps guide that conversation of okay, you're going to have your chance now. Say your piece now. We're going to move down a path here. Hopefully that's helpful in terms of earlier is better.
William Lindstrom:Earlier is better, and it also sounds like keeping it into layman terms and asking those key questions. And I know, having come out, having been in finance and done valuations before, you know we can get into the jargon, but as you're sitting with the family, you know. How do you explain what valuation is and how it works and the concept of risk in a way that they can go? Okay, I see how my participation in this is going to either lift the valuation or potentially impair the valuation, and especially since I heard from GF Data lately that 82% of exits are actually below their optimal valuation, so clearly something's wrong and this process needs to be fixed. So, on that note, how do you explain it to them in a way that it becomes collaborative and team oriented and people understand their role?
Len Bruskiewitz:I think that's a big piece of it is having the conversation and assigning roles. One of the other early pieces is building an advisory team, which is a fancy way of saying you got to make sure that your financial planner is involved, you got to make sure that your estate planner is involved, you got to make sure that your estate planner is involved, the other professionals that can help. But really it's around just making sure that the family, in this case, understands at a basic level how companies do get valued. That can be a rather mechanical one. The basic idea is it's earnings times a multiple. That's a pretty simple way to say it. Then you say but there are these levers and the levers that impact that are how risky those earnings are to continue.
Len Bruskiewitz:What I typically do is bring up examples of risk factors. One risk factor may be that there's no management level between the owner and the workers. There's a gap there, and so if something were to happen to the owner, the earnings would be at risk because there's kind of nobody to fill in the gaps. And so that's what I try and do is just give examples of things that increase risk and other. If the family, or if the group is it kind of understands the business. I'll talk about customer concentration risk. I'll say, hey, there's a risk here because 80% of the revenue is coming from three customers and if one of those customers goes away that's a really big deal. So I talk about risks in as concrete a terms as I can, just so that they know that it's not a purely mechanical calculation as to how value is derived.
William Lindstrom:No, I think that's good to bring it back down to the, because I think people forget that you know, past performance is not projected a future performance, especially with all this topsy-turvy stuff going on with the economy. Really appreciate your time. So if you want to leave kind of the concept of like, what's the one thing? If you wanted to leave someone or piece of advice for a company that's thinking about selling particularly around the whole concept of company risk specific, you know, company specific, risk premium, that idea that the leadership you know the leadership can both boost and impair performance or valuations, what's the one thing you would leave us with?
Len Bruskiewitz:I'm going to go back to getting owner independence is the single biggest thing to work on today. And that back to my two week vacation test. If you can confidently say yeah, I could leave for two weeks and everything would be just as it was when I left, or even better. That would be the biggest indicator to me of where you are as a company and how prepared you are to transition out of.
William Lindstrom:No, that's great advice and I really appreciate your time. We try to keep these short and to the point, but this was a great conversation about risk, particularly around how to incorporate family into both mitigating against it and also preparing the owner and founder for the next journey beyond their company.
Len Bruskiewitz:Awesome, I appreciate the questions. This was fun.
William Lindstrom:Thank you so much and until next time. Thanks everybody.
