Ep 278: Readiness 360 for Exit Planning
Key Takeaways
- 73% of business owners who feel ready to sell are actually missing at least one of the two crucial numbers needed to know if a sale will fund their future.
- Having a minimum required number and a recent credible valuation is not the finish line of exit planning readiness, but rather the starting point.
- Over a quarter of business owners cannot name a single activity they are excited about after exiting, highlighting the danger of lacking personal readiness.
- Exhaustion and burnout are driving nearly half of all exits, often causing business owners to agree to deal structures they deeply regret later.
- Evaluating exit planning readiness through the Readiness 360 framework ensures that both the owner and the business are truly prepared for a successful transition.
73% of business owners who say they're ready to sell are missing at least one of the two numbers required to know if a sale will actually work. In this episode, David breaks down a new data study of 10,548 business owner assessments and lays out the Readiness 360 — the three questions every owner has to answer honestly before they sit across from a buyer. Are you personally ready to let go? Is your business actually ready to be sold? And does the math even work?
What You'll Learn
- The two numbers every owner needs before they can know if a sale will work — and why 73% of owners are missing at least one
- Why even owners who did the homework still get bad news: 1 in 5 discover their business is worth less than they need
- The “pushed vs. pulled” problem — why burnout and stress are driving more exits than actual planning
- Why 25% of owners can't name a single thing they're excited about after the sale, and what that means for a deal
- The eight drivers that determine whether your business survives buyer diligence — separate from how much cash it generates
Timestamps
- 0:00 — Cold open: You've decided to sell. Here's why you're not ready.
- 0:45 — Intro: framing the Readiness 360
- 2:30 — Segment 1: Are you financially ready? The two numbers
- 9:30 — Mid-episode: the Sellability Score
- 10:00 — Segment 2: Are you personally ready? Pushed vs. pulled
- 16:30 — Segment 3: Is your business ready to be sold?
- 21:30 — Wrap-up: putting the 360 together
- 24:00 — Where to start: Sellability Score and PREScore
Key Takeaway
“Wanting to sell is not the same as being ready to sell.”
Only 27% of business owners have both a minimum number and a recent valuation — the two things required to know whether a sale will fund the life they want afterward. And even among owners who have both, roughly 1 in 5 find out the business is worth less than they need. Readiness isn't a feeling. It's a diagnosis, and the earlier you run it, the more options you have.
Ready to Find Out Where You Stand?
Start with the free Sellability Score — a 15-minute assessment that shows you where your business stands on the eight drivers that determine what it's worth:
weeklywealthpodcast.com/sellabilityscore
Want to go deeper on personal readiness? The PREScore assessment measures whether you — not just the business — are ready for what comes next:
weeklywealthpodcast.com/prescore
Frequently Asked Questions
What is exit planning readiness?
Exit planning readiness is a comprehensive diagnosis of whether you are financially prepared, personally ready to let go, and whether your business is genuinely prepared to be sold without your constant presence.
What are the two numbers every business owner needs before selling?
Every owner needs to know their minimum number—the least amount of cash needed to feel financially secure—and a recent, credible valuation of what the business commands in the market today.
Why do business owners fail their exit strategy?
Many owners fail because they rely on feelings of burnout rather than objective data, leading them to discover shortfalls too late or enter deal structures that do not match their personal tolerance.
How can I assess my exit planning readiness?
You can evaluate your preparedness by utilizing assessment tools like the Sellability Score to review business drivers and the PREScore to measure your personal readiness for life after the sale.
00:00 - Untitled
00:00 - Introduction to Business Ownership
03:12 - Understanding the Readiness Gap for Business Exit
08:31 - Understanding Owner Readiness for Business Exit
11:37 - Understanding Exhaustion vs. Readiness in Business Exits
15:19 - Understanding Business Readiness for Sale
Hey, you.
Speaker AHey, business owner.
Speaker AYeah.
Speaker AYou know who you are.
Speaker AYou've been working at your business.
Speaker AYou've been pouring your blood, sweat and tears into it for decades.
Speaker AYou've taken risks.
Speaker AYou've had years where you've made a lot of money.
Speaker AYou've had some years where you literally made negative money.
Speaker ANow you're in your 50s, your 60s, and you're thinking about selling your business.
Speaker AYou're thinking about, am I ready to exit my business?
Speaker ASo today we are talking about three questions that need to be answered by business owners who are even considering exiting their business.
Speaker AAnd these would be about three different areas of their lives.
Speaker AAnd if we're not on point for all three of those questions, and if we don't know the answers properly, it can be an expensive mistake, both for quantitative and qualitative reasons.
Speaker AToday we're talking about readiness360.
Speaker AThese are three questions that every owner has to answer honestly before they ever sit across from a buyer or even really think about finding buyers.
Speaker AAre you personally ready to let go?
Speaker AIs your business ready to be sold?
Speaker AAnd are you financially ready?
Speaker AWelcome to the weekly Wealth Podcast.
Speaker AI am certified financial planner David Chudick.
Speaker AThis podcast and my wealth management practice are both designed to help the mass affluent to live better lives by how they handle their money.
Speaker AWe talk about financial strategies, prosperous mindsets, and simply how to build true wealth.
Speaker ASo come on and let's enjoy this journey together.
Speaker AWelcome to this week's episode.
Speaker AI'm David Chudick.
Speaker AThis is the weekly wealth podcast and we talk about the mindsets, the tactics, and the strategies that can help you to build and maintain wealth.
Speaker ANow, I ask every week, if you're not driving, take a moment to follow us on Instagram, follow us on YouTube, follow us on Facebook, and if you've gotten any value from the show, it would be amazing if you would forward an episode to a friend, a family, a colleague, a co worker, or a business owner.
Speaker AAll right, so now that that's out of the way, if you're a business owner, at some point you've thought about selling.
Speaker AI know that you have, because I have also.
Speaker AMaybe you've thought five years from now, maybe it's just your dream that you're going to walk away with that proverbial hundred million dollars.
Speaker AMaybe your health is declining, maybe you have another business or another interest that you.
Speaker AYou might like to pursue.
Speaker ABut most business owners have exiting their business in their plans in some way, shape or form.
Speaker AMaybe you thought about it when you woke up this morning.
Speaker AYou're thinking I just can't do this anymore.
Speaker ABut here's the problem.
Speaker AMost owners judge their readiness by how they feel.
Speaker ALike I'm tired or I'm done, or the timing feels right, or like I feel like I still have more to give and I shouldn't sell.
Speaker AI feel.
Speaker ASo feelings are not a plan.
Speaker AFeelings are just feelings.
Speaker ARight?
Speaker ASo wanting to sell, or maybe even not wanting to sell is not the same as being ready to sell or being at a point where maybe you should sell.
Speaker ASo today we're going to talk about the readiness gap.
Speaker AAnd it's built off of three different assessments that we use.
Speaker AIt's based off the prescore, the personal readiness to exit.
Speaker AIt's based off the freedom score, and it's based on off of the sellability score, all of which are available for you to take.
Speaker AAnd it breaks readiness into exactly three lenses that I've mentioned.
Speaker AAnd I want to walk you through all three, because most owners, and honestly, most advisors, only ever check one of them.
Speaker ASo there are exactly two numbers that you need to know before you can know whether a sale would work.
Speaker ANumber one is your minimum.
Speaker AThat's the least amount of money you'd need to walk away with and still feel financially secure.
Speaker AAnd number two is a recent and credible valuation, what the business could actually command in the market today.
Speaker ANow, this is not what you think it's worth, and this is not what your friends think it's worth.
Speaker AThis is not what it was worth three years ago, and this is not what you think it might be worth in three years.
Speaker AThis would be a credible valuation now.
Speaker ASo that's it really.
Speaker AThat's two numbers.
Speaker AAnd it doesn't really require a PhD.
Speaker AAnd yet only 27% of owners have both numbers.
Speaker AOne third have one, but not the other.
Speaker ANearly 40% have neither.
Speaker AYou add that up and you get a headline.
Speaker A73% Of owners are not financially ready to exit by the most basic definition of the word.
Speaker ASo let's be clear here of what that doesn't mean.
Speaker AIt does not mean that 73% of owners are incapable of selling.
Speaker AIt means that 73% of owners have no way of knowing whether a sale would even hit their number.
Speaker AThey're driving towards a destination without knowing how much gas is in the tank.
Speaker ASo here's a part that might surprise you, and it surprised me.
Speaker AYou'd expect this cluster.
Speaker AMaybe burned out owners, skip the homework, or maybe owners who've been at it forever have it more dialed in, right?
Speaker ANope, that's not the way it works.
Speaker AOwners who are burnt out, ready to retire, long tenured, or eager to cash out are all missing both numbers at nearly the same rate, roughly 30 to 41%, depending on the group.
Speaker AEven the owners who say cashing out is their main motivation, the ones you think are the most financially dialed in, nearly a third of them still don't have that number either.
Speaker ABeing motivated is not the same as having the math done.
Speaker ASo if you're listening to this and thinking, I'm not the type of owner this applies to, that's exactly the thought the data says to ignore.
Speaker AThere's no reliable tell.
Speaker AConfidence isn't proxy preparation.
Speaker AFatigue isn't tenure isn't.
Speaker AThe only way to know is to ask yourself right now, do I actually have both numbers?
Speaker ANow, here's the part I think is the most important finding in the whole report, and it's the one most people will skim past.
Speaker ASay you're in the lucky 27%, right?
Speaker AYou've got your minimum number.
Speaker AYou've got a real valuation.
Speaker AYou did your homework.
Speaker AYou must be ready, right?
Speaker AWell, among owners who have both numbers and compared them directly, 64% found the business was worth at least what they needed.
Speaker ABut 21% discovered it was worth less than what they needed, and another 15% weren't even sure.
Speaker ASo if we say that again, more than a third of the owners who did everything right, they got their minimum number, they got their valuation, they still walked away, either with a shortfall or a giant question mark.
Speaker ASo having both numbers doesn't mean you're ready to sell.
Speaker AIt means you're finally reached the point where you can find out whether you're ready to sell.
Speaker AThat's a completely different thing.
Speaker AAnd the valuation doesn't just validate the plan.
Speaker AIn a lot of cases, it changes the plan.
Speaker AAnd here's why timing matters so much.
Speaker AA shortfall you discover five years before a sale is a planning problem.
Speaker AAnd that can most likely be fixable growing the business a little more.
Speaker AAdjust the number, build a bridge.
Speaker AA shortfall you discover six months before a sale when you've already told your team, already started imagining the boat or the golf schedule or the tennis schedule or the pickleball or whatever comes next.
Speaker AThat's not a planning problem anymore.
Speaker AThat's a failed transaction or a delayed retirement or a disappointed owner sitting across the table from a buyer trying to renegotiate.
Speaker AThat's the whole case for starting early.
Speaker ANot because you have to sell soon, but because the earlier you find the gap, the more options you have to close it if you're a business owner and if you're not 100% sure, you have both of those numbers, your minimum and your recent valuation.
Speaker AThat's exactly what the sellability score is built to surface.
Speaker AIt's free, it takes about 15 minutes, and it'll show you where you stand on things that drive your business worth.
Speaker ASo go to www.weeklywealthpodcast.com saleabilityscore that's www.weeklywealthpodcast.com be in the Show Notes okay, so let's say the numbers work.
Speaker AYour minimum is covered.
Speaker AYour valuation is at least in the ballpark of where it needs to be.
Speaker AYou're financially fine.
Speaker AYou're ready, right?
Speaker AMaybe.
Speaker ABut the report asks one more question.
Speaker AI think it's the sneakiest one in the whole thing.
Speaker AWhat are you most excited about after you exit?
Speaker AAnd a full 25% of owners could not name a single thing they were excited about doing after the sale.
Speaker ANot that they had a boring answer.
Speaker ANot that they said travel.
Speaker AAnd I don't believe them.
Speaker AA quarter of owners, when asked what they're moving towards, came up with nothing.
Speaker ACompare that to the owners who could answer.
Speaker A46% Said spending time with family.
Speaker A40% Said travel.
Speaker A28% Said getting healthier.
Speaker A28% Said said a hobby.
Speaker AThose are people with a picture in their head of Tuesday morning, six months after the closing.
Speaker AThe 25% with nothing.
Speaker AThey don't have that picture yet.
Speaker AAnd quite frankly, they may lose a sense of purpose in their life and they may not have happiness.
Speaker ASo this fix is not really like a spreadsheet fix.
Speaker AIt's not a numbers fix.
Speaker AIt's a conversation about life after the company.
Speaker AI've said this on the show before and I'll say it again.
Speaker AFor a lot of owners, the business just an asset.
Speaker AIt's an identity.
Speaker AYes, I know my business is part of my identity as well.
Speaker AAnd whether that's good or bad, it simply is.
Speaker AA lot of days it is a big part of the reason why I get up.
Speaker AIt's the reason people call me.
Speaker AIt's the reason people know who I am and when it's gone and there's nothing built to replace it.
Speaker AThe money in the bank doesn't fix that Tuesday morning problem.
Speaker AAnd then the second layer to this is like why the owners are even considering an exit in the first place.
Speaker AThe report splits reasons into two buckets.
Speaker APlanned reasons, things like wanting to cash out.
Speaker AIt's time to retire.
Speaker ADiversifying wealth, which is a big one, and reactive Reasons like stress, burnout, it takes too much time.
Speaker AHealth concerns.
Speaker ASo too much stress.
Speaker A49% Burnout, 48% takes too much time.
Speaker A43%.
Speaker AThose numbers have barely moved since before the pandemic.
Speaker ANo spike, no.
Speaker ANo decline.
Speaker AIt's not a moment.
Speaker AIt's structural.
Speaker AExhausted owners are not necessarily prepared.
Speaker AOwners, they're not ready.
Speaker AThey're just done.
Speaker AAnd the distinction matters more than it sounds like it does because of what happens next in the deal.
Speaker ALook at this one.
Speaker A76% Of owners are willing to stay on as a consultant after the sale.
Speaker AOnly 31% are open to an earnout.
Speaker AJust 9% want to leave immediately.
Speaker AA tired owner will say yes to almost anything in the room to get a deal done.
Speaker AThen, six weeks into a required transition period, they resent every minute of it.
Speaker AAdvisors and buyers who don't catch that risk.
Speaker ABuilding a deal structure that looks perfectly rational on paper and completely misreads what the owner can actually tolerate on the other side of the signature.
Speaker AIf you're pushing yourself towards the exit door because you're exhausted, that's real.
Speaker AI'm not telling you exhaustion isn't valid.
Speaker AI'm telling you exhaustion is not the same thing as readiness.
Speaker AAnd conflating the two is how owners end up in deal structures they can't stand six months later.
Speaker ASo let's talk about the third lens.
Speaker ASo far we've covered personally and financially, the third lens is the one that actually determines whether your valuation number is any good in the first place.
Speaker AIs the business itself ready to be sold?
Speaker AThat's where the saleability score comes in.
Speaker ABecause it's built around eight specific drivers that determine whether a business commends a premium multiple or gets picked apart in diligence.
Speaker AThings like how dependent the company is on you personally.
Speaker AIs revenue recurring or one off.
Speaker AHow diversified is the customer base?
Speaker AIs there a management team that can run this without the owner in the building?
Speaker AHere's the connection.
Speaker ABack to that 21% we talked about earlier.
Speaker AThe owners who got a valuation and found out it was less than they needed.
Speaker AIn almost every one of those cases, it's not that the market is being unfair.
Speaker AIt's that the business has one or two of these drivers working against it.
Speaker AToo much owner dependency.
Speaker AA customer lists with three accounts that are 60% of revenue.
Speaker ANo documented system, so a buyer can't picture running it without you standing there.
Speaker AA business can generate great cash flow and still be nearly unsellable.
Speaker AThe two are not the same thing.
Speaker AThis is the piece that's fixable furthest in advance.
Speaker AAnd it's the one that owners are least likely to check on their own.
Speaker ABecause from the inside, a business that feels like it's working fine is a business that's valuable.
Speaker AThis is the piece that's fixable furthest in advance, and it's also the one owners are least likely to check on their own.
Speaker ABecause from the inside, the a business that's working feels like a business that's valuable.
Speaker AThose aren't the same question, and a buyer will absolutely tell the difference.
Speaker AThe only choice you have is to find out from a buyer or from a saleability score assessment two or three years before you need the answer.
Speaker AAll right, so let's put this whole thing together, right?
Speaker ABecause this is what I want you to walk away with now, when you're thinking about potentially exiting your business, and preferably we're thinking several years out, right?
Speaker ARight.
Speaker AYou first have to think, am I or will be financially ready to exit?
Speaker ASo financially ready means you have your minimum and you have a somewhat accurate valuation, and you've compared them because having both isn't the finish line.
Speaker AIt's the starting point.
Speaker ARight?
Speaker ASo.
Speaker ASo we have a tool called the Freedom Score, and it can help you determine what your minimum needs to be.
Speaker AAnd then the sellability score will give you a range of values of what your business might sell for.
Speaker ANow, again, the sellability score is not a certified valuation, but it's a great starting point.
Speaker ANow, personally, are you ready?
Speaker AYou know, so we have the prescore, the personal readiness to exit score.
Speaker AAnd personally ready means you can name what you're moving towards, not just what you're moving away from.
Speaker AAnd you're honest about whether you're being pulled away by a plan or pushed away by exhaustion.
Speaker AAll right, so what would you do when you're no longer working in the business?
Speaker AWould you volunteer?
Speaker AWould you.
Speaker ADo you have interest?
Speaker AHow is your health?
Speaker AThings like that.
Speaker AAll right, so again, we need to be financially ready.
Speaker ASo is our money ready for us to sell?
Speaker AAre we ready to sell?
Speaker AAnd then is the bag business ready to sell itself?
Speaker ARight, so we're not just talking about the P and L. We're asking, can your business survive diligence in the selling process and stand on its own without you in every room?
Speaker AAnd if you miss any one of those three, and I'm ready to sell is a feeling and not a fact.
Speaker ASo the transaction is a visible event.
Speaker AThat's when you're in the attorney's office and you're signing papers and money is changing hands.
Speaker ABut readiness is the work that happens long before it.
Speaker ABut the good news is, and this is genuinely really good news, every one of these gaps is fixable.
Speaker AThe data backs that up too.
Speaker AReadiness hasn't meaningfully improved industry wide over seven years.
Speaker AWhich tells you the problem isn't awareness, is that nobody's actually sitting down and doing the diagnosis.
Speaker AThat part's on us, it's on you, it's on the advisors.
Speaker AAnd honestly, it's a pretty short conversation to start.
Speaker ASo why are we talking about, like business readiness?
Speaker AWhy are we talking about, you know, why is a financial advisor talking about are you personally ready to sell your business?
Speaker AHow would you feel?
Speaker AWhat would you do?
Speaker AWhat would give you meaning?
Speaker AYou know, your typical financial advisor, they're trying to convince you that they have the best way of managing money, that they can get you the best return.
Speaker AThey have investment processes, blah, blah, blah, blah, blah, blah, blah.
Speaker AAnd yes, that is all important.
Speaker AHowever, as I always say, I believe that how we handle our money should positively impact our lives and the lives of those around us.
Speaker AAnd if you're a business owner, your business is a tremendously large part of your life.
Speaker ASo how you manage that asset is a large portion of your life.
Speaker AAnd it should be part of the financial planning process with you and your advisor.
Speaker AWhen you should exit and if you should exit should be a major part of your financial planning decisions.
Speaker AOkay, so we're not just talking about fluff stuff.
Speaker AThis is really, really important.
Speaker AIf you've built a business and it could be worth multiple 6, 7, 8, 9, 10 figures, we need to treat that as the asset that it is.
Speaker AAnd we also need to deal with the quantitative and qualitative aspects of exiting your business.
Speaker AI want my clients to feel really good about their exit.
Speaker AIf they choose to exit, I want them to exit at the right time, for the right price and for the right reasons.
Speaker AAnd if I'm not helping with that, quite frankly, I'm not a very good financial advisor.
Speaker ASo that is a little bit of food for thought there.
Speaker ASo if any of this jumps out at you and you would like to have a 10 or a 15 minute conversation, let's do a vision call.
Speaker AGo to www.weeklywealthpodcast.com vision.
Speaker AThat's www.weeklywealthpodcast.com Vision.
Speaker AWe can take 10 minutes, 15 minutes.
Speaker AWe can meet in person if you're local, or we can meet via Zoom and we can talk through a couple of these concepts.
Speaker ANo pressure, no fluff, just a conversation.
Speaker AAll right everybody.
Speaker AUntil next episode.
Speaker AI wish everybody a blessed week.
Speaker AThanks everybody.
Speaker BThe information presented on this podcast is for general educational purposes only and does not constitute financial investment, legal or tax advice.
Speaker BParallel Financial is registered with the U.S. securities and Exchange Commission SEC as a registered investment advisor.
Speaker BRegistration does not imply a certain level of skill or training, nor does it constitute an endorsement by the sec.
Speaker BAll investing involves involves risk, including the potential loss of principal.
Speaker BPlease consult a qualified financial professional before making any financial decisions.
Speaker AHere is your bonus content for this week's episode.
Speaker ANow, there's something in investing called concentration risk and that talks about having too much of your net worth or too much of your investment in any one position or one type of position or maybe a certain sector or anything like that.
Speaker ASo oftentimes, maybe you'll have someone who works for Apple or IBM or Microsoft and they're getting stock options or they're getting granted stocks frequently.
Speaker AAnd little by little their portfolio starts becoming too heavily weighted in that one stock.
Speaker ASo maybe they have a million dollars and, I don't know, $50,000 of their of their portfolios in Microsoft, that's 5%.
Speaker AThat's probably not 2 too overly weighted.
Speaker ABut let's say between automatic purchases and an increase in that one stock, we look at it and now they have 15, 20, 30% of their money in that one stock.
Speaker AWell, that's concentration risk and that's kind of the proverbial all the eggs in one basket.
Speaker ANow let's look at the same thing for business owners.
Speaker ATypically a large portion of their net worth is tied up in the business.
Speaker ASo at a point, maybe if you've reached the freedom point or if you're close to it, it might make sense to take some of those chips off the table and to diversify by selling all or part of your business and not having so much of your net worth tied up in that one asset.
Speaker AJust a thought.
Speaker ALet me know what you think.
Speaker AEmail me davidarallelfinancial.com.