Nathan Gregory

I was 25 and just boarded a jet at Teterboro to fly from NYC to Toronto with the band KISS for a concert. As we made the short flight, the map showed us flying over the small town in rural upstate NY that I grew up in. I couldn’t help but but laugh to myself at how absurdly ironic that me, a homeschooled kid, was now part of the management team for KISS and other iconic artists. Thrown into the deep end with KISS, navigating Guns N’ Roses through fashion week, my music management career was nothing short of a baptism by fire. My stint in music management eventually brought me to the top talent agency CAA where I negotiated and managed brand partnership deals for top celebrity music talent for 10+ years. Something was gnawing at me though… - Did I want to be dealing with the drama that surrounds artists as I got into my 40’s and 50’s? - Did I want to be chasing commissions all my life? - Did I want my time to constantly be hijacked be the latest talent crisis? -------------------- From a young age, I had a burning desire for independence, control of my time, and a strong wealth building vehicle. Over time I dabbled in various opportunities that I thought would give me that freedom. - I bought and sold raw land in Arizona, Wyoming, Utah, Oregon and California. - I acquired multifamily real estate. First in Austin, TX, then switching to Long Beach, CA. - As an experiment, I started a party favor beer koozie brand, which then blew up into a 7-figure business which I sold in 2021 - Started my media acquisition path with acquiring content websites Around 2019 I learned about Acquisition Entrepreneurship and made a decision that this was going to be my path. A few years later, after over 100 deals analyzed, pauses, false starts, and multiple offers, we found the right business for us. Because of me and my partner’s background, and the need stable earnings, we were exploring the more enduring side of media - B2B media - as one of our target criteria. In 2023 we found a 42yr old B2B media business covering the automotive collision repair industry. The owners had acquired the business 16 years before us, had grown it substantially, and were ready to retire. We saw this as an incredibly stable platform, with an impeccable and long-lasting reputation in the industry, and plenty of opportunities for us to expand. 7 months ago we acquired Autobody News and I’m having the most fun I’ve had in a long time. My journey to acquisition entrepreneurship taught me a few important lessons: 1. Being true to yourself and your skills: Like so many searchers, during the majority of our search, we thought we’d acquire a home services business. It turned out that really wasn't right for us, and only when we pivoted to an industry we had some experience in (media) were we able to find and close on an acquisition. I've also seen that play out for us in a big way in the operation of the business, as I'm able to draw on prior skills, knowledge and even my network. 2. Being persistent and adapting over time: Our search process and criteria evolved over time as we learned more. Not only did we change, but the market changed when interest rates increased and the macro economy slowed. 3. How to overcome imposter syndrome: I was home schooled and went to college for music production technology, nothing close to an MBA. I LOVE to learn, and through endless reading, podcasts, acquiring and owning commercial real estate, starting and running various small side-projects businesses, I eventually developed the skill set to successfully acquire and run a great business. If you also have a winding path, I’d love to connect and hear about it. Share below!

@markcecchini Same for us real estate investors! 🤦‍♂️

What's wild to me is all these people who over-indexed to angel investments and random VC funds have had to watch those investments sit on their net worth statements at cost (or worse) while the S&P and NASDAQ have gone 2X over the last 5 years brutal

@SHistorians I'm just happy the street I live on is named after this course "Cypress Point Drive"

Ran into a guy literally 5 minutes ago at breakfast. He was wearing a Cypress Point belt. I remarked, “I see you are wearing a Cypress Point belt. That is my favorite golf course in the world. He responded: “To be honest with you, I don’t like it. It has thirteen of the most average golf holes I have ever played!” I am not proud of this- but I literally…kind of…yelled… “WHHHAAAAAT?” He then replied: “You couldn’t pay me to play there again.” I haven’t been in a fight since middle school- he was many year my senior and a thought crossed my mind that he would Bob Barker me. How anyone on this planet can have that opinion and still be a golfer.

@btaylor Our head of content says you can "take em dashes away from her cold dead hands"

I deeply resent that AI has forced me to eliminate em dashes from my writing for fear of signaling slop

Asked our advertisers to name their top marketing challenges: Half said brand perception. Nobody named the competitor that actually beats them. No trade show booth. No ad budget. Already inside the vendor's customer's business, talking to the owner every day. Status quo wins more deals than any competitor does.

Yes, everyone else should definitely do that! 🤣 For B2B publishers with sponsored content, no-click AI powered search results are boosting their value proposition to advertisers because of of Google AI, Perplexity, etc consider the authority of those publishers vs the advertisers’ own sites. A strong reason to not block Google for those publishers! x.com/nathandgregory…

Every other digital media company should block Google.

@sweatystartup Huge demand, and also really sophisticated competitors. The joke about competing against the "guy with the fax machine" doesn't fly in a market like ours, LA.

A lie a lot of entrepreneurs believe that expensive cities are bad places to start a service business. The truth is that they're some of the best places. In high cost of living cities, hourly labor is scarce because people can't afford to live there on $10-15 an hour. That means your competitors can't staff up, can't keep up with demand, and can't deliver consistent service. Meanwhile the customers in these cities are earning a lot of money doing what they're best at, and they're paying other people to do everything else. I grew up in a Midwest town where nobody hired anyone. We mowed our own grass, cleaned our own windows. My college friends from the Massachusetts suburbs had a pool guy, a lawn guy, a plumber. It's a completely different way of life. So yes, labor costs more in these cities. In the midwest we had people lining up to work for $12 an hour. In Boston and DC we were paying $18 an hour just to find someone who can pass a background check. But labor is only about half your expenses. Paying double the hourly wage only raises your cost to deliver the service by 25 percent. Meanwhile you can charge two to three times more for the same job in these cities than you can in a cheaper market. So start a low-skill business. Simplify the job so normal, moderately trained employees can run it. Compete on speed. Answer the phone, be eager and professional, and raise your prices.

@bmorrissey There is an inverse strategy for certain B2B publishers when it comes to AI powered search content. x.com/NathanDGregory…

USA Today Co CEO told me it will soon look at blocking Google altogether. "The traditional Google search model is dead."

@GaelBreton I don't know, but ChatGPT helped me win my NFL football pool this past season.

Can I use Codex Computer use to play online poker for me? 🤔

@shawngorham We're seeing some major developments with AI in collision repair. The most powerful tools we've been shown haven't even come out yet. x.com/NathanDGregory…

AI is never going to take over the trades...

PDFs aren't dead... Content that answers questions ain't nobody asking is dead. Our whole market is 35K collision shops. When we run lead gen for our advertisers selling high-ticket products, the best performing assets are always the ones that answer the burning question the target audience is already asking. Content format is basically the last decision we make.

Breaking news from Letterland Live: PDF lead magnets are DEAD. Basically... At least, that's according to @HubSpot's VP of Media & Content @jonathan_h on @davegerhardt's @exitfivemedia podcast. What will the next generation of lead magnets look like? Calculators? Tools? Quizzes? via @JPMorinChase and @louisnicholls_

4/ What belief keeps them stuck? Usually "what we have works fine." Put a crack in it with proof. Then when they finally go looking, they find your answer instead of your ad.

3/ Who feels it first? The tech, the owner, and the multi-location exec all live the same event differently. One message can't reach all three. Three pieces of content can.

Every SaaS or brand trying to sell a product to blue-collar trade businesses are running ads looking for "awareness" Almost none of them can answer the four questions that make awareness worth buying. 👇

“How To” books are great for learning. But the “How Did…” genre of History and Biographies will REALLY teach you.

I weigh myself every morning to capture an average over time. Today: 177.6 🇺🇸 🦅🇺🇸

There are times in our lives when imbalance is balance, when a short-term focus contributes to our overall mission in life. - Stephen Covey

@BlakeMycoskie Are you still doing sailing racing?

Today I’m 49. I started TOMS at 29. Sold it at 43. By 47 I was in the deepest depression of my life. These aren’t 10 hacks. They’re the things I wish I had understood before the résumé started mattering more than the soul.

@MarketingMax I’ve had a similar experience in Pakistan. Some of the best people, across several different businesses and industries.

I'm exclusively hiring from Serbia now Every Serbian I've hired is 100/10 complete all-star hall of fame, proactive, and above and beyond talent Sorry not sorry