Entrepreneur in Focus: Nathan Gregory

Sometimes the Winding Path Can Get You There

Pete Weishaupt
6 min readApr 10, 2024

Whether you’re new to Entrepreneurship through Acquisition, or ETA as the cool kids call it; or an old hand at buying and selling small businesses, Nathan Gregory’s story is nothing short of inspiring. Sometimes the winding path really can get you there. Nathan comes from an unconventional space. He was a guitar player in a touring band, worked in the entertainment industry, spent time in a tech startup, dabbled in e-commerce, and invested in commercial real estate. After his recent appearance on the Acquiring Minds podcast, I caught up with Nathan to learn more about his journey from guitar player to purchasing a business in the B2B media space.

The Making of an Entrepreneur

Unlike a lot of small business owners, Nathan’s parents weren’t entrepreneurs. The driving force for him came from the “6 Human Needs” summed up by Tony Robbins as:

  • Certainty
  • Uncertainty/Variety
  • Significance
  • Connection/Love
  • Growth
  • Contribution

Nathan felt he needed to become an entrepreneur to fully realize those core human needs. He was restless when working at various companies. Nathan is always trying to take things in the direction he wants — which isn’t really possible when working for someone else.

His journey into acquisition entrepreneurship began with acquiring and repositioning commercial multifamily real estate with the goal of increasing the Net Operating Income (NOI) of his properties. Commercial real estate values are tied to a ‘cap rate’ on NOI, and a rising NOI means a corresponding rise in the value of the properties. And not to get bogged down in the math, Nathan says the light bulb came on when he realized you could apply the same approach to business acquisition. But you actually have far more levers to pull with a business than you do with real estate. Later, he used this insight to form a thesis around acquiring niche information/media/content businesses that he could improve and grow.

Once the thesis was formed, Nathan’s toughest challenge was understanding how to evaluate and value a business. Once he’d moved beyond the basics, the next challenge was to truly understand the nuance of valuation and “value” in general to understand how to separate the good businesses from the rest of the pack.

This led Nathan to acquire Autobody News, a 42-year old trade publication for the automotive collision repair industry. Autobody News stands out from the crowd by delivering regional content on a national scale. Nathan is currently doubling down with more reporting sources and audience segmentation.

After immersing himself in the automotive collision repair industry, Nathan says thinking about the niche altered when it came to the audience and how to serve them best. A core value at Autobody news is “Audience Obsession”. This spirit came from Nathan’s experience in entertainment media where you serve fans. Other B2B media seems obsessed with advertisers. The audience tends to come second. Nathan has ‘flipped the script’ by focusing on audience engagement. He notes having an incredibly engaged audience and offering measurable and effective ways for advertisers to connect with that audience means the advertisers will be there.

Another piece of advice, and one that Nathan rates as probably the best advice he’s received as an acquisitive entrepreneur, comes from his fractional CFO: “Run your business like a financial asset.” “I think it’s easier for someone who acquires a business to think this way rather than a founder,” Nathan says, “but it’s still a crucial framework that you need to put in place so that you are solving for increasing the value of the business overall, not just solving for annual income.”

But Wait, There’s More!

Now strictly speaking, there are many stripes of entrepreneurs from all different industries, and by and large they all beat to a different drum; though there are a few common threads we can learn from. Especially when it comes to inspiration and motivation. Nathan says for inspiration he’s constantly absorbing blogs, books, podcasts, tweets — anything that will help him synthesize and cross referencing ideas. He points out, “I don’t think I actually have a lot of original ideas, I think most of my ideas are inspired by others.” For whatever reason, this sentiment seems to be a common theme across most ‘acquisition entrepreneurs’, myself included. And when it comes to motivation, Nathan says having two kids lit a fire under him he didn’t know he had. There’s also a bit of a shift in motivation as he looks at being an entrepreneur or an investor, and those areas in between the two. Understanding both approaches and developing frameworks around each feeds his motivations and time allocation. Nathan says, “I’m always reading to learn, and trying to engage and network with other interesting people.”

Pivotal Moments

One entrepreneurial endeavor Nathan is particularly proud of was starting an e-commerce company in 2018. The company sold beer koozies with designs and phrases printed on them. The brand was started from scratch and grew to be a leader in its category on Amazon. He sold the business in 2021, which validated everything he’d been trying to do — mainly create something with real and transferable value. It may not have been his biggest financial outcome, but he says it’s one he’s really proud of.

A Deeper Dive

Among the things one picks up on a winding path is good advice from unexpected places. A very successful rockstar client once asked Nathan’s music management firm, “do you know why we pay you so much? Not to ask us what we want, but to tell us what we should do.” And this is a lesson Nathan has always carried with him. The point is to make sure he’s offering a valuable perspective to his clients and customers.

“Follow your passion.” If that seems like good advice, For Nathan it’s not so good, and one most people haven’t really thought through. He loved music, so he pursued a career in the music industry. But as he grew in the industry, he found himself spending his days reviewing legal contracts, negotiating, chasing clients, and appeasing partners — none of which really had anything to do with music. Rather than “following your passion”, Nathan says, “I think it’s far more important to know what kind of actual work (meaning the actions you take like: writing, selling, coding, planning, laying tile, forecasting, etc) gives you energy, and when you figure that out, you can operate in different industries that you may not be “passionate” about and still really enjoy the process.”

When it comes to defining success, Nathan says making progress on the direction and timeline of a plan he’s set sums it up.

But no entrepreneur profile would be complete without a few ‘favorite entrepreneurs’ and a couple of books. This one is no exception. For inspiration, Nathan likes the calmness and holding company approach of Andrew Wilkinson of Tiny. He also admires the big thinking and platform building approach of Brad Jacobs. Those themes are central to Nathan as an entrepreneur. He finds himself more aligned with successful entrepreneurs who do acquisitions as a main part of their playbook.

Nathan has read many books which have provided him with tactical guidance and frameworks — he could list several dozen. But, Disney War by James B. Stewart made a particular impression. It’s a beast. “If you think that you operate with intensity, think again.” says Nathan. The book is packed with stories of round the clock board meetings, two lines of people outside of Jeffrey Katzenberg’s door cycling in to meet him while he was rolling calls…on and on. The lesson in the book is how to operate at a savage level of ferocity and how to handle immense pressure, competition, and adversity.

Key Takeaways:

The most important thing about being an entrepreneur is the constant need to adapt and learn.

  • You must be able to quickly change course when necessary. You must be willing to learn new things in order to stay ahead of the competition.
  • You must be able to build strong relationships with customers and other key stakeholders.
  • You must be able to manage your time and resources effectively in order to succeed.