This one is special.

On a recent podcast, I spoke directly to part-time, self-funded searchers and the very specific challenges you face. I break down why investing in help is the best way to shorten your 24 month search into as little as 6 months. My students have done it. So can you.

Here’s how:

Topic-Based Summary of the Podcast Below (for those who aren't video watchers):

Why 90% of Business Buyers Fail

Why Should You Listen To the Podcast:

90% of business buyers never get a deal done. But that doesn't have to be you. There are tried and true ways to get deals executed that differ from what a lot of people are spewing on social media and the web. Tune in so you can understand how to get that done. You can be a million-dollar business owner too.

Why Should You Listen to Me/Elliott:

I am Elliot Holland. I'm a Harvard Business School alum. I've spent 15 years in small business acquisition. I've been on all sides of it. A rich business buyer, poor business buyer, self-funded business buyer, business buyer advisor, and now I have a master class. I've been in this longer than almost anyone. I'm known for telling the truth. And I speak in simple terms, so nobody will get lost on the way, and that's why you should listen to me.

What Clients Do I Serve?

Most of my clients are working in corporate jobs. They've been there 10 to 20 years, and now they decide they want to buy a business. It sounds great, and everybody says it's easy. Three months in, they're bleeding. What do I mean by bleeding? They've called 10 brokers and got no responses. They submitted offers on three deals and got outbid all three times.

Why Do These Amazing Professionals Struggle? What Do They Struggle With?

They've been ignored. They've been told they're not qualified. They've been told they need to get pre-qualifications. They've had to go from their corporate jobs saying yes to everything and making their boss look smart. Sometimes they give their best work to their boss. Because who wants to piss their boss off and get fired?

Now they have to be the person that's gonna show up with a million dollar Brinks truck and they can't take crap from anybody. From a broker, seller, advisor, lawyer, all of that. Probably the biggest negotiation they've ever been in has been over $20k to $30k. Now they're in a negotiation about $3 million, $5 million, $7 million. They don't know how to handle those situations

The reason most people fail is that they're going from a very structured, protected corporate environment. They have the ambition and the brilliance to desire to buy a million-dollar business, but really in this new job, they don't know squat.

They don't have two or three years to learn. They don't have 10 years to apprentice. And so how do you get something done in a year that takes people 30 years to learn when you're already 20 years until your career making $100k, $200k, $400k a year? Typically, my clients have families, kids. There are just too many constraints on the system for people to do it themselves.

The other issue that makes it difficult is that a lot of people are making, let's call it $250,000 a year. They've been in their career 10, 20 years, and now they want to go be a million-dollar business owner and operator. But there's a huge gap in between. And so where people get stuck is sort of, there's enough pain to desire to do something outside of your job. But not enough pain to after three, six months of not being successful, to continue to stay on top of this very lucrative job that most of their friends would die to have. That pays all their bills, takes care of their family. They’re still motivated to do the extra 10 hours a week, 20 hours a week to get this other amazing thing done when first, the first amazing thing that they’ve done. Most people have not accomplished themselves. So you're really on an island yourself in this $250,000 a year track.

The other reality is you start looking up, and you're four or five, six rows below the CEO. And you've seen how long the people take to get to that CEO spot, and you don't think you have a real chance. And so now the desire you had when you started your career to be the big person, the head honcho now becomes a more fleeting less than likely outcome.

And so you want to get out of it, but all that money sure is fun to spend.

Let's talk about the skills that are most difficult to get on your own. You don't go from negotiating $20,000 differences on houses, $30,000 differences on salaries to $3 million differences on purchase price overnight or by reading a book. One of my favorite books is You Can't Teach a Kid to Ride a Bike at a Seminar, and that's what you'll be doing. Learning to ride a bike at a webinar. You actually don't know valuation or financial modeling for small businesses at all. And I don't care if you're the greatest Wall Street, billion-dollar business modeler or somebody that works at a tow truck company. You're not any good at this. And this is mission-critical to this new job you'll be doing, and you're not gonna get good at it. Where you'd be willing to bet two, $3 million on it in six to 12 months.

So how do you actually accomplish that? The other issue that you have to really get good at is calling baloney Bull Squat Sasquatch, because unlike in your corporate environment, where everybody tells the truth, because lying can get you fired, he or everybody lies and telling the truth can get you fired. How do you figure that out and how can you figure out a person telling you things smiling, especially a seller who probably made their 30 year career selling other people. How are you gonna tell if they're selling you a pound of lead versus a great opportunity? And so those are the three or four things you're gonna need to do incredibly well to put yourself in a position where a $3 million investment can turn into six or 12.

What Happens If You Mess Up On Something This Big

What if you mess up on one of those things and instead of putting up three and getting six? You put up three and get zero or negative 3 million. Are you willing to bet that on doing it yourself or trying to rush it?

So the first 90 days are all about two things: getting deal flow and getting your mind ready to execute.

Where Does My Mastermind Come Into This?

Let me tell you what the real benefit of my program is relative to others. You're not gonna learn this in a group or a cohort. With some online, group-based whatever. You're gonna need one-on-one time.

I'm the only program out there with one-on-one time with the expert. We meet for an hour every week. Before we even talk about what we learn, let me tell you how you won't learn it somewhere else because the topics aren't really it. It's actually the level of comfort, the level of specificity, the nuance that you actually have to learn these things with the format that's required to learn them.

Why Group or Cohort-Based Classes Don’t Work

Let me just further break it down. If I have seven or eight nuanced questions about a $1 million deal, but to get to the end, I might have to look at 50 million deals. So now I have 200, 300 questions over the course of six months, and I'm in a group course, so I get an hour of the expert's time amongst 30 other people.

 I get a question every fourth or fifth week. Out of my 200 questions, I get three answered. But you pay some money for that. You big dummy. That's what a lot of these people are offering, or you learned it in a video. So learning how to negotiate a $3 million deal on a video, let me tell you how that's gonna go.

You ever seen a plane crashing? That's what it's gonna look like.

What You Actually Need

The first thing is you need one-on-one time, because each week you're gonna have 4 to 12 nuanced questions that are gonna be backed up with spreadsheets, situations, brokers, lawyers, sellers, kids, industry, cities. And all that stuff is gonna have to intermix with your own risk appetite.

How much money can you afford for the answers at the nexus of all those things? How else are you learning that without one-on-one time? We go through deal sourcing, finding more deals than the average person. We go through quickly getting to an idea about an offer. We go through negotiating an offer letter, which is called a Letter of Intent, and there are 10 modules that we go through. I'd be lying to tell you that the modules are where you get the value.

It's the method by which you learn in one-on-one time. That's really the only way to learn this. That's truly the differentiation.

Case Study

One of my masterclass students was working a very lucrative job at one of the world's largest companies. Had been searching for a business to buy for a year and got nowhere. They joined my program right around the time when people were telling folks they needed to come back in the office from remote work.

Instead of having a zero-minute commute from the bedroom to the office in the house, now they have a one-way, one-hour commute each day. They ended up leaving their job because after spending a year looking for a business to buy and not being successful, they sort of knew they had about six months left to get something done or they have to quit.

They left their job. We spent two or three months in an intense deal sourcing endeavor, really recognizing that six months was the time that we had on the clock. Found an amazing deal in the United States, in the northwest sort of corridor. Went through the due diligence process of making sure that the business was what the seller said.

I helped them go through Quality of Earnings and going through fundraising, which was a big pain in the butt, but I coached him through that. And then going through the legal document process to make sure that all of the risks that were identified could be mitigated in the legal documents. In between the time when my students started in November of 2024 to April of 2025, when they closed in less than six months, they had gone from a job where they probably would never see a million-dollar upside to a million-dollar business that they own.

Now, when they go do a piece of work for this home service company. They get the check at the end of the day, and this person would like to do other deals

Their Process Before & After the Mastermind

They tried on their own for 12 months to get their first deal done and failed. This student isn't like your average, everyday high school graduate.

This is someone who could command a job at a Top 10 World Company, so you can understand how great this person was. But they failed at this job without help. Then six months into my program, they succeeded. And there are four or five others that are referenced on my YouTube channel about how they did the same thing.

Why Urgency is Everything! (Your Family Cannot Wait)

90% of my Masterclass members are married with one or more children. My peers who have two or three kids that are 10 to 15 or 20 years old. I know how much they run around between their job, their kids, their partner, their church, and by the time you have all that going, the likelihood you have another 20 hours to go do this is slim.

Come on, man. Any one of those on any given week can kill it. And in the four weeks, in a month you're gonna get killed. Three out of four, you're just not gonna have the time to do it. It's not responsible anymore. So why did I bring that up?

The Bigger WHY for Most Buyers (Family Level Up)

For most of my masterclass and mastermind members, one of the huge benefits of this is working a lot harder than the average person for a year or two to get ownership of a business, where now they can hire people to help out to buy their time back.

To be able to spend more time with their partner and their kids. And so by the time they get to a place where life and family and work are taking most of their time, they're able to buy that time back by hiring a general manager, by hiring a marketing manager, by hiring other people.

Not only do they get their time to spend with who they love the most, but they also get the ability for their children to not only have the regular job choices that everybody has, but also they can come in and either take a job or buy into the family business. So they have new options that their parents never had, that most people never had.

I've seen second-generation business ownership where the grandfather gets to spend a whole lot of time with his grandkids because the mother and the father aren't encumbered by somebody else's 60-hour-a-week ploys at a job.

I'll tell you, you'll see freedom. When you witness that second generation into a business, and so there's a bigger upside for most of my masterclass members in that the generation of wealth transfer is one part of it, but having the time to spend with your grandkids and your kids unencumbered is probably more so what people are going for.

90% Still Don’t See These Outcomes

I told you about a lot of great things that people have accomplished, but let's keep it real. I'm telling you things that 9 out of 10 people don't get done, and not 9 out of 10 everyday people. I'm talking about 9 out of 10 of the world's greatest, smartest, most capable, most well capitalized, most liked that have the best jobs.

When they set out to do this, 9 out of 10 of them don't get it done. Let’s not split hairs here. This is not easy, not simple. This is not a do-it-yourself weekend project. This is not putting a fence up in the backyard. This is not painting one side of your room so you can get some more light in it.

This is a life's work for a person of means. If you have the ability to get expert help on a one-on-one basis, you'd be a fool not to. And hey, I can't help everybody, but I sure wouldn't want you walking into something where 90% of the people fail and not knowing it.

Where to Find Me

If you want to find out more, and I bet you do, go to thebusinessbuyingmasterclass.com or check out my YouTube channel. I'm excited to hear from you there!