From Survival to Scale: The Power of Acquiring to Grow

Entrepreneurship is not for the faint of heart. It is full of high hopes, unexpected challenges, and defining moments that test every ounce of your creativity and resilience.

When I sat down with business strategist and entrepreneur Tom Shipley on The Amanda Kaufman Show, we explored one of the most underused yet powerful strategies for growth: acquisition. This was not a conversation about corporate takeovers or mergers of billion-dollar brands. It was about something far more relatable and inspiring. It was about how entrepreneurs can use acquisitions to scale faster, solve big challenges, and take control of their growth journey.

The Hard Truth About Building a Business

Let’s start with the part few people talk about honestly. Building a business from scratch is hard. Tom described it perfectly when he said it feels like being “dragged through asphalt and glass.” Every founder knows that feeling. The sleepless nights, the cash flow crunches, the constant pressure to make the next move work.

As Tom shared his story, it was clear he had been through it all. There was a time when his business was running out of money, and he had only ninety days left of cash. Most people would panic, pivot, or shut down. But instead, he did something different.

He asked a bold question: What if the fastest way forward was not to start over, but to acquire?

Turning Crisis Into Opportunity

Tom’s first acquisition was not part of a grand plan. It was born out of necessity. With little cash left, he found a company that was twice the size of his own and managed to structure a deal that allowed him to acquire it.

That single decision changed everything. Within ninety days, his business went from barely surviving to tripling in size. Within a year, he exited the company successfully.

It was not luck. It was perspective.

That experience showed him what was truly possible when you stop thinking only about organic growth and start thinking strategically about acquisitions. As he put it, “Acquisitions can solve almost every business problem.”

Rethinking Growth

For many entrepreneurs, the default approach to growth is to work harder and aim for steady, incremental gains. But as Tom explained, that approach has limits.

He broke it down with simple math. Most business owners spend years grinding for 10 or 15 percent annual growth. If everything goes perfectly, they might increase the value of their business by 50 percent after five years. That sounds respectable, but it is also exhausting.

Now compare that with a well-planned acquisition. One strategic move can double or triple your business overnight. It can add new revenue, talent, infrastructure, or cash flow that you would otherwise spend years trying to build.

This is not about buying companies recklessly. It is about thinking like a visionary. It is about seeing your business as part of a larger ecosystem instead of a single, isolated project.

The Real Reason Entrepreneurs Hesitate

Many founders think acquisitions are only for large corporations or venture-backed startups. Tom’s story proves otherwise. His first deal happened when he was nearly out of money. His second major acquisition came when he and his business partner had proven their model but lacked cash, team, and infrastructure.

Instead of stopping, they found a company that had everything they needed and worked out a deal. They placed their smaller brand on top of a larger platform and grew it into a one hundred million dollar business within three years. Over time, that little skincare brand generated one billion dollars in revenue.

The key was not resources. It was resourcefulness.

Opportunity Is Everywhere

One of the most powerful insights Tom shared was about the landscape of opportunity in today’s economy. He said, “Did you know that there’s a thousand baby boomers that own businesses that are retiring every single day? Two thirds of their businesses will never sell.”

That statistic stopped me in my tracks. Thousands of businesses across the country are closing because their owners are ready to retire and have no one to take over. Behind each of those businesses is a loyal team, a base of customers, and a legacy waiting for someone with vision to continue it.

Imagine the possibilities if more entrepreneurs stepped in, honored what those owners built, and grew it further. This is not just about buying businesses. It is about preserving livelihoods, serving communities, and creating win-win opportunities for everyone involved.

The Mindset That Makes It Possible

At the heart of this episode was a lesson that applies to every entrepreneur, no matter what stage of growth you are in. The real breakthroughs happen when you are willing to see your challenges differently.

When things fall apart, you have two choices. You can panic and pull back, or you can get creative and look for opportunities others might overlook. That mindset shift is what separates the entrepreneurs who survive from the ones who scale.

Acquisition is just one example of what becomes possible when you adopt that mindset. Whether you are buying a business, forming a partnership, or creating a new offer, the goal is the same. Keep expanding your thinking. Keep looking for leverage. Keep moving forward.

From Struggle to Scale

Tom’s story is proof that strategy and resilience can turn the toughest situations into the greatest opportunities. He did not wait for perfect conditions. He acted with purpose, clarity, and courage.

If you are in a season where growth feels hard or uncertain, this episode is a reminder that there is always another way. You are never stuck if you are willing to look at your challenges differently.

Because at the end of the day, business is not just about surviving. It is about scaling with vision, purpose, and heart.

Chapters List

00:00 Changing Paradigms in Business Acquisition

01:14 The Moment Everything Changed for Tom’s First Business

03:43 How an Acquisition Solved Cash Flow and Tripled Growth

06:02 Why Most Entrepreneurs Grow Too Slowly

07:25 How to Buy a Business When You Have No Cash

10:43 Lessons from 16 Acquisitions and Exits

11:52 The Birth of DealCon and the Future of Entrepreneurial Growth

15:22 The Opportunity Hidden in Baby Boomer Businesses

Full Transcript

Tom Shipley (00:00)

it's difficult building a brand.

It's like being dragged through asphalt and glass and startups are tough.

things happen in business that are out of your control and it impacts your business. And then, so what do you do?

Amanda Kaufman (00:30)

Well, hey, hey, and welcome back to the Amanda Kaufman show. And I'm so excited to introduce you to Tom Shipley. He is a serial entrepreneur, an ⁓ &A strategist. And for those that don't know, that's mergers and acquisitions. And he's the creator of Add A Zero growth philosophy. He's been helping founders to 12X their business through strategic acquisitions.

Tom, welcome to the show. Thank you so much for joining me today.

Tom Shipley (01:00)

We're excited to be here.

Amanda Kaufman (01:02)

my gosh, so mergers and acquisitions. When I very first started as an entrepreneur about eight years ago, it was all about getting clients and getting started and writing. We were talking about copy before we went live and it was just like this frenzy of you have to be in the room and you have to talk to people and then you have to sell something great. there's just all this noise, I think, around the front of building a business. And why I was so excited to have you here today is because you're talking about

businesses as assets and you're talking about building something that really lasts. So I have to ask you like what told you when you were an entrepreneur that you needed to do something differently to grow to that next level?

Tom Shipley (01:44)

didn't start with is when I did my first two acquisitions. I didn't know any better. There was no one teaching this. There was just, there was no rule books back then. And it was just the first one I fell into and my second one. Both were acts of I had no other choices. What do do when your business runs out of money? And let's put this way as an entrepreneur, it's difficult building a brand. Building a business from scratch is

Amanda Kaufman (02:01)

Mm.

Tom Shipley (02:09)

It's like being dragged through asphalt and glass and startups are tough. So I remember my first business is, you know, from concept to getting it up to the level we did to a nice solid business. was just a miracle. And then we had this great little business and then things happen in business, whether it's dot com crash going back and dot com bust, whether it's the 2007

2008, whether it's COVID, whether it's 9-11, things happen in business that are out of your control and it impacts your business. And then, so what do you do? And for me with my first business is we were doing great. It was an online store. We mailed in out millions of catalogs and we grew this from our initial fundraising where I raised $10,000 and suddenly life is going good. Wins at our back.com. Bus happens.

recession hits, we're losing money. My CFO says we're out of, we have 90 days of cash left. As I think I share with you, I knew that was nonsense because I knew we had 90 days. We'd stretch for 90 days. He was, he's being a little bit dramatic, but, and we were very fortunate that a gentleman that I met at a catalog conference at that time was an investment banker. And he said, Tom, I have the perfect acquisition for you. And I went, I don't have money for payroll in my head.

But I said, sure. And in that case, was a, he was representing companies selling it off and they have an orphaned asset that the buyer didn't want, which was a $15 million business. And for us, was double, that was twice your size. And so we worked a deal out within 90 days, we acquired this business, got an ROI in 30 days and a year later I exited that business. And it was like, wow, that was cool. But I didn't think of that as a business model. But imagine this is,

In 90 days time, I'll sign one, we solved our cash flow issue and we were triple the size. Okay? So, and we were out of cash when we did that.

Amanda Kaufman (04:05)

And there's no way, like

I'm trying to think of examples in business where you would do that in 30 days. I, no way. Or even 90 days, yeah.

Tom Shipley (04:13)

Or 90 days. Yeah, yeah, or 90 days. How could you do that? Right, you can't.

You can't. Most people, let's just say this, most people grind really hard and they say, we're going to go for a 15 or 20 % growth. But we know that it goes like this. So if they average 10 % growth a year for five years, assuming nothing bad happens, they increase their value of their business by 50%. Five years of grinding and they increase their business by 50%. Compare that with an acquisition. Now let me fast forward three years later.

where we decided to take my blueprint for building iconic brands using direct response marketing applied to the industry. Everyone said we fail, especially two former special forces guys in Richmond, Virginia, launching, saying, we're going to build a $100 million beauty brand. And everyone laughed at us. We're not from the industry. We don't know. No one's ever used direct response in 2005 to build an iconic beauty brand. And here we are. We said, watch us.

And suddenly at the end of the year, we proved the model work, but at $331,000 in sales, again, Richmond, Virginia, two former special forces guys, we proved the model work, but we lost a little bit of money. We couldn't borrow the money. We couldn't raise any money. But what do you do when you run out of money? I learned from lesson one is you buy a business. We bought a $15 million business, throwing off a million in the cashflow. But let's go back to what acquisitions do. One is

you can solve almost every business challenge through acquisition. What was our challenge? We didn't have cash and cash flow. Number two is, we didn't, back then, there was no SaaS platforms you could plug into. There was no Shopify. There was no microsite platform. So we actually needed a platform, a funnel or a microsite platform. We didn't have a team. It's everything else was great. So we needed everything. And suddenly we did this acquisition and we had everything we needed.

We put our little $331,000 brand on top of this little $15 million platform. Within three years, we did $100 million. That little skincare brand, we did a billion dollars over its life cycle. Now, if you think about it, we didn't have resources, we didn't have money. Again, we knew we had this big aspiration, but we had some real key challenges. Acquisitions can solve almost every business problem. You can grow. I'm going my method.

Amanda Kaufman (06:31)

This is what I'm starting to really begin to appreciate. I started my career in consulting and I got to work on some really cool like mergers and acquisitions when I was earlier in my career. We'll just say that. And I could appreciate why like these big, it was actually the biggest merger in Canadian history. There were these big oil and gas companies that were coming together and I got to work on the merger.

side of things to help them activate their synergies. So like I understood that. But now I've been an entrepreneur for about nine years. I'm working on my ninth year. And what I'm really beginning to appreciate more as a founder and as a business owner is that so many business problems or puzzles can be solved if you're willing to look at it through a new lens and a different way. And to your point, I mean,

the acquisition, I think a lot of people listening might feel the same feeling that a lot of people have, which is these golden handcuffs. Like I have to keep doing what I'm doing because this is the way it's the way that it's always been. It's how I've always done this, maybe in their business. You acquired large companies when you had no cashflow. So can you break that down for the listener? Because they may be thinking about acquisitions like I acquire a car. They might be thinking in terms of like,

consumer acquisition and not business deals.

Tom Shipley (07:55)

percent. So let me break down the second acquisition that we did. So here we were is that we ran out of money. We couldn't feed our own families. Again, things got really, we just went all in because that's who we were from personality. We're out, so we're cash-strapped, but the metrics for our business were good, so we were committed. But here we are, we were able to, basically we were doing some consulting with the company in New Jersey, helping them out.

because we need direct response offline marketing. They're really good online and we're doing some coaching for them and a way for us to bring in some income. And so we said, now, this is the way it happens. It's very simple is we love your business. We'd love to buy it. And again, we didn't have any resources. Would you be interested in selling it? A lot of times now I give discussions with different entrepreneurs and I said,

What is your long-term goals? And that's where I start my discussions. Because what's your long-term goals and when do you want to sell your business? What will you do afterwards? And so I get into discussions and you'll find out where people's role goals are, which is really, this is selling your baby is a people. with them, was they had bigger goals, what are their aspirations and what do they want to do? And we said, we'd love to buy your business. And, and suddenly they said, well, for how much? And then we.

came to price and with that just chatting with them. And then, okay, now we need money to buy this business. Back then it was an e-comm world. We bought it for under about 2.7 times their EBITDA, which is great. So again, from a multiple price perspective. And so then we went out and I again used my network, asked around who can help us find the funds to do it. So and our accountant said, I have a great broker.

This is all he does and he helps people find debt financing. We met him and we found out somehow found the cash up for a retainer for him because we had nothing left. We paid him and he was great. And he went out and he reached out to his network, put together our book and our, our, our plan, reviewed it. And then he called, then he reached out to his network and he had five companies that were interested. Three came into Richmond to meet with us. We presented to them over a

one day period. And then of that, two of them gave us term sheets. And so we bought the business for 80, in that case, 85 % cash is what we bought it for. But remember, it was, they brought, and we didn't have any, it wasn't that we didn't have any equity put into it. And they didn't loan us the money on a three to $31,000 business that was losing money. They lend us the money because they saw two smart guys buying a profitable business that was growing every year.

and two very smart guys were coming over to take this over and we're going all in with that business. So the mezzanine level financing company believed in us. They backed us and we bought the business and we bought 85 % of the business. Now, two and a half years later, we bought the extra 15 % from the owners for as much money as we paid them for the initial 85 % because we grew that. So it was a home run for them. It was great for us.

Amanda Kaufman (11:13)

just good business. Seneca said that luck is when opportunity meets preparation. And so I understand you have a convention around deal making that you've put together to show entrepreneurs another way forward. So can you talk to us a little bit about what is DealCon and all of that?

Tom Shipley (11:32)

Absolutely. I

sure will. And let me get some context to this is that over the years, I've done 16 acquisitions and exits. I'm an industrial engineer by background. So therefore, you take complex and make it simple into processes. So when it comes to buying businesses, 70 % is the processes and systems and knowing what to do.

30 % is the EQ because you're buying businesses from people, knowing what to say, how to say, developing relationships, again, having those scripts, but it's all part of the process. And so it happened that I was dragged into with friends, teaching them how to do acquisitions in a group of friends that we got together three years ago to teach them. Basically, people ask me, can you teach us your process?

for programmatic &A and my answer was, I'm too busy buying businesses. I don't have time for that. Finally, we said yes and we had a dozen friends come in Austin. We taught them how to acquire basically our blueprint and we thought that was great. And then we did it six months later for 25 different companies and then five months later for 40. And now every six months we get a group of entrepreneurs together that are action oriented.

They're open-minded. They're looking for ways to scale disproportionately to organically. Some of them have clear exit opportunities. They want to sell in one year. They want to sell in five years. They want to sell in three years, or they want to become the platform and do other acquisitions. For long-term growth, it really doesn't matter. we bring seven to nine figure entrepreneurs. Our events keeps them growing by 20 % each time. So we just had an event in Austin.

DealCon CEO M &A Summit with 120 entrepreneurs. And our next one's gonna be about, we're gonna cap it at 150, it'll be in Miami, February 9th through 11th. And my goal is very simple. We want, we're passionate and we will go on and we will share everything from our blueprint, our resources there, our attorney that we use is there, our financing sources there, our brokers there. Our goal is that a lot of times I think we talk about a mandate is that I see entrepreneurs doing acquisitions because they...

can, but it's kind of like playing with a chainsaw and throwing a chainsaw in. Okay. If you know the process of the system, you can responsibly and successfully acquire a business. even, and again, the example I gave was a cash deal on We Road brought money in. But I can share this with you that we brought about two agencies over the last few years for 5 % cash at close.

The rest of it's seller notes and or not. Everything was about the motivation. And the other thing we didn't talk about is just kind of a stat on this. Did you know that there's a thousand baby boomers that own businesses that are retiring every single day? In the United States, a thousand baby boomers that own businesses. Two thirds of them, their businesses, only a third will ever sell. Two thirds of their businesses will never sell.

Amanda Kaufman (14:32)

daily.

Tom Shipley (14:44)

What do they do when they don't sell the businesses? Well, they're ready to go on so they close the businesses down. So the opportunity is there as you go to those business owners and say, hey, I love what you built. I want to take care of your customers and your team. Here's my vision. What I'd like to do for your business. And then you do a financial structure that is really good for them, which is better than them getting zero and closing it down. Their employees are out of work and their customers are out of luck.

Again, so that's the paradigm shift and everything is about seller motivation. I don't like to go through brokers because I don't like to be in that time constrained period of time and in a competitive environment. I believe in buy size processes where we just do, we generate leads, we get to talk to sellers on a regular basis and find ones with businesses that want to sell. it's the right one, that's really the metric and that's the process that we like to teach. And that's the opportunity. But the first thing is,

changing people's paradigm about what is possible. And then here's how to do it. And then here's the playbook. And that's what we love to teach. And we do this right now twice a year at DealCon.

Amanda Kaufman (15:52)

Amazing, Tom, what is the best way for someone to keep up with you and find out what's next?

Tom Shipley (15:59)

Okay, so very simple. Go to my website, tshipley.com, t-s-h-i-p-l-e-y.com. There's a link to dealconlive.com right there and there will be links to all my social media handles because I publish regularly on Facebook, Instagram, and LinkedIn.

Amanda Kaufman (16:18)

Beautiful and dear listener, we've got all of those links in the show notes below. Thank you so much for shining a light on this opportunity. I know that there are definitely listeners of this show that you need that plan of where you're gonna go next. So like really thinking about what are you creating? I love how it can help so many business owners have a real path forward.

at the time that they wanna exit, whether they're exiting to grow some more or they're at a different life stage, just having all these small businesses and medium businesses and large businesses really go somewhere through collaboration. That's what this is all about. So, fantastic. And dear listener, if you love this and you actually have a friend who is in business and wants to learn more about mergers and acquisitions as a strategy, make sure you grab the link to this episode and you text it to them and you tell them,

how helpful this was for understanding. And don't forget to hit subscribe, of course, for the next episode. And if you really love this, the thing that helps the most is when you take a moment to leave us a kind and honest review because it helps people to choose this show. Tom, thanks to you again for being here. Really appreciate you.

Tom Shipley (17:32)

Absolutely, only the best to Amanda.

Amanda Kaufman (17:35)

All right, and dear listener, we'll see you next time and until then, do what matters.