The conversations that usually stay behind closed doors.
Welcome to The Confidential Business Show, or as our listeners know it—Confidential BS.
Hosted by entrepreneur and business broker Kacy Carlsen, Confidential BS takes you beyond the headlines and highlight reels to uncover the real stories behind business ownership. From buying and selling businesses to leadership, growth, negotiations, setbacks, and the pivotal moments that shape an entrepreneur's journey, these are the conversations most people never get to hear.
Some episodes feature candid conversations with business owners, buyers, sellers, investors, and industry experts. Others are solo episodes where Kacy shares personal experiences, observations, and lessons learned from decades of building businesses and helping entrepreneurs grow.
Whether you're an entrepreneur, investor, business owner, aspiring business buyer, or simply fascinated by what really happens behind the scenes, Confidential BS offers honest conversations, practical insights, and stories that inspire, educate, and challenge the way you think about business.
Business Stories. Business Secrets. Business Strategies.
What happens when a million-dollar business deal turns into a full-blown love triangle? 🍷
This week on Confidential BS, I'm joined by Vanessa Sterling, a sharp-tongued, quick-witted business broker with 20 years of experience and enough stories to make your jaw drop.
Vanessa takes us behind the scenes of a seemingly perfect $1.2 million business sale. The financials looked great, the buyer was qualified, and everything appeared to be moving toward a successful closing.
Until due diligence uncovered a mysterious woman receiving $8,000 a month in “consulting fees.”
Let's just say… the biggest liability wasn't on the balance sheet. 👀
We're talking business secrets, questionable expenses, marital drama, and what happens when personal decisions threaten a million-dollar deal.
Because in business brokerage, sometimes the numbers aren't the only things hiding something.
🎙️ Business Stories. Business Secrets. Business Strategies.
Confidential BS with Kacy Carlsen — where we talk about the business behind the business.
Disclaimer: This episode features a fictional, dramatized story created for entertainment and educational purposes. Characters and events are fictional.
Thanks for listening to Confidential BS.
If today's story resonated with you...
Or you know another entrepreneur who needs to hear it...
Welcome to the Confidential Business Show, the podcast where we have the conversations that usually happen behind closed doors. Real business stories, business secrets, business strategies. I'm Casey Carlson, and this is Confidential BS. Let's get into it. Welcome back to Confidential BS, where we talk about the business of buying and selling businesses, and occasionally the absolute BS that comes with it. Now, today's episode is going to be a little different because I've got a guest joining me. And let me tell you, this woman has stories. My guest today is Vanessa Sterling. She's been in business brokerage for over 20 years, has handled everything from small mom and pop shops to multi-million dollar acquisitions, and has probably seen more drama in business transactions than most people see in an entire lifetime. Vanessa, welcome to Confidential BS.
SPEAKER_01
Casey, thank you for having me. Although I have to say, when you invited me on a podcast called Confidential BS, I thought, finally, someone who understands what we actually deal with in this industry.
SPEAKER_00
Right? Because people think we just list a business, find a buyer, collect a commission, and everybody lives happily ever after.
SPEAKER_01
Oh, bless their hearts.
SPEAKER_00
Exactly. But you've been doing this for two decades. You've seen the good, the bad, and I'm guessing some pretty ugly.
SPEAKER_01
Girl, I've seen business partners turn into mortal enemies. Family members who haven't spoken in 15 years suddenly show up wanting their share of a sale, and buyers who apparently think due diligence is optional.
SPEAKER_00
Ugh, don't even get me started on that last one.
SPEAKER_01
And that's just a Tuesday.
SPEAKER_00
So before we get into today's story, I have to ask you something. After 20 years, what is the one thing that still surprises you about this business?
SPEAKER_01
You know what? It's not the money. It's not even the negotiations, it's the secrets. People will tell you everything about their revenue, their equipment, their customers, but the things they don't tell you? Honey, those are the things that can blow up a million-dollar deal.
SPEAKER_00
Ooh, I feel like that was a little foreshadowing.
SPEAKER_01
Oh, you have no idea.
SPEAKER_00
Okay, so when we were talking about having you on the show, you said you had a story that involved a million-dollar business, a married couple, and a situation that went completely off the rails. And you wouldn't tell me anything else.
SPEAKER_01
Because I wanted to see your face when I told you.
SPEAKER_00
Well, you've got my attention. What happened?
SPEAKER_01
Girl, get comfortable because this one has everything: money, marriage, a mistress, and a million-dollar business. Oh, we're starting strong. So I get this listing. Beautiful company. Commercial cleaning business. 20 employees, recurring contracts, almost 2 million in annual revenue. Okay, we love recurring revenue. We do. And the owners are this married couple. Let's call them Richard and Susan. Married 27 years, built the business together.
SPEAKER_00
Aw, the American dream.
SPEAKER_01
That's what I thought. Richard tells me they're selling because they want to retire and travel. Famous last words. So we list it for $1.2 million. Get a qualified buyer, full price offer. Everything is moving beautifully until due diligence. Dun dun dun! The buyer's accountant notices an expense. $8,000 a month. Every month. For three years. For what? Consulting. Consulting what? Exactly. There's no contract, no invoices, no deliverables, just eight thousand dollars leaving the business account every single month.
SPEAKER_00
That's $96,000 a year.
SPEAKER_01
Thank you, Miss Calculator. So I call Richard and ask who the consultant is. He says, Oh, that's just someone who helps with marketing.
SPEAKER_00
Okay, show me the work.
SPEAKER_01
That's what I said. And suddenly he's very busy.
SPEAKER_00
Imagine that.
SPEAKER_01
Two days later, Susan calls me and she says, Vanessa, I need to ask you something. Who is Tiffany? No!
unknown
Yes!
SPEAKER_01
Don't tell me Tiffany is the consultant. Yep. Tiffany is the consultant.
SPEAKER_00
Oh, damn.
SPEAKER_01
But wait, it gets worse. How? How does it get any worse? Tiffany isn't just Richard's girlfriend. Richard has been telling Tiffany that he owns the business outright and that once it sells, they're moving to Costa Rica. With Susan's money? Yep, with Susan's money.
SPEAKER_00
Jeez, I need a drink.
SPEAKER_01
Oh honey, we're not done.
SPEAKER_00
There's more?
SPEAKER_01
Susan finds out. Obviously, she's furious. She calls her attorney, and now she doesn't want to sell the business.
SPEAKER_00
Oh no. Because now we're talking about ownership, authority to sell, and potentially a divorce.
SPEAKER_01
Exactly. But here's the kicker: the buyer still wants the business.
SPEAKER_00
Well, of course he does. If the company is genuinely profitable, he's looking at $96,000 in questionable annual expenses that might disappear after closing.
SPEAKER_01
Exactly. But we can't just call that an adback. We have to establish what the payments actually were, whether any legitimate services were provided, and what the real financial picture looks like.
SPEAKER_00
Right. And now the buyer's wondering what else hasn't been disclosed.
SPEAKER_01
Bingo! So Susan finally agrees to continue the sale, provided everything goes through the attorneys.
SPEAKER_00
Please tell me Richard went to Costa Rica alone.
SPEAKER_01
Better. Tiffany finds out Richard doesn't own the whole company. And she dumps him. Stop it! And Susan? She hires a divorce attorney, negotiates her interests, and eventually agrees to proceed with the business sale.
SPEAKER_00
Please tell us. Did the deal close?
SPEAKER_01
Six months later, after legal negotiations, updated financial disclosures, and a whole lot of due diligence.
SPEAKER_00
And Richard?
SPEAKER_01
Last I heard, he's living in a one-bedroom apartment.
SPEAKER_00
Vanessa! But seriously, there's a lesson here. When you're buying a business, the financial statements are only the beginning. You need to understand where the money is going, who's getting paid, who actually owns the company, and what obligations you're inheriting.
SPEAKER_01
And when you're selling a business, get your house in order before you put it on the market.
SPEAKER_00
Preferably your actual house, too.
SPEAKER_01
Especially if Tiffany has a key.
SPEAKER_00
And that is why I say buying or selling a business is about more than numbers. It's about people, personalities, and sometimes a whole lot of baggage. I'm Casey Carlson, your business matchmaker, and this has been Confidential BS. Remember, when it comes to buying or selling a business, make sure you know who you're getting into bed with. Vanessa! We are not ending with that. Oh, yes, we are. See you next time. That's today's conversation. But it's certainly not the last because every business has another chapter. Thanks for listening to Confidential BS. I'll see you in the closed doors.
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