『464 | Why Selling Your Business to a Holding Company Could Triple Your Exit. Josh Wilson Explains the Math.』のカバーアート

464 | Why Selling Your Business to a Holding Company Could Triple Your Exit. Josh Wilson Explains the Math.

464 | Why Selling Your Business to a Holding Company Could Triple Your Exit. Josh Wilson Explains the Math.

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Connect With ChazJosh Wilson started at seven years old on a cruise ship, charging his vacation friends a markup to use his grandfather's cruise card. He built a wedding DJ business at 16 and sold it at 19 for $25,000. His only W2 job was two months as a buggy boy at Winn Dixie before he got fired. Since then he has built a 25-million-dollar real estate portfolio, lost over a million dollars on a single investment, and pivoted to M&A where he is now acquiring his seventh company with a goal of 10 companies and 10 million in EBITDA before exiting to private equity.In this conversation with Chaz Wolfe, Josh breaks down the entire M&A framework he uses: what to look for in a target company, why he only buys companies doing at least a million in cashflow, the five reasons a contractor business owner should consider selling to a holding company instead of selling on the open market, why most businesses have not raised prices since COVID, and how the multiple arbitrage game works when you roll your equity into a holding company instead of taking a 3x exit alone.Key Takeaways:The first question in any acquisition: when was the last time they raised prices? Nine out of ten businesses Josh looks at have not raised prices in years. A 10 to 20 percent price increase is often the first value add after closing.Only buy companies doing at least one million in cashflow. Below that threshold, you cannot afford to hire the management team you need to actually run the business. You end up doing everything yourself again.A 3x multiple on your own is a mom-and-pop exit. Roll your equity into a holding company targeting 8 to 10x and you may triple your eventual payout for waiting a few years.PE companies buy cashflow, not hustle. When private equity looks at a portfolio, they want a C suite in place, a back office running, general managers in every entity, and systems that do not require the founder. Build that picture and you become attractive.Going wide to find your vertical is not always a mistake. Josh spent five years acquiring different industries to find where he could go deepest. He is now locking in on transportation. The path was the education.The mentor moment that changed everything: Josh was sitting in a hot tub during COVID, watching his real estate portfolio and wondering if his tenants were going to pay. In that moment he realized he could not keep living his entire life this way. That discomfort drove the pivot.If I can't do it, no one can is a guarantee that you will never scale. Josh learned it the hard way. The C suite he built is the only reason he can now focus exclusively on vision and growth.Pivoting is not failure. Real entrepreneurs master the art of knowing when things are heading in the wrong direction and correcting course before it costs them everything.$25,000 was enough to count as a real exit. The size of the deal does not determine whether the principle applied. Josh knew how to create value and find a buyer at 19 years old. The same principle runs his 7-company portfolio today.Build the right C suite first. CFO, COO, CEO roles need to be filled by people who love operating, not just people who are available. Josh found each one through deliberate relationships, not desperation.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you.Through peer mastermind and 1:1 coaching, we help you:increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply.Connect with Chaz Wolfe (Host):WebsiteFacebookInstagramLinkedInYouTubeProfit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the showLike what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
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