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Countryside Road

Our Story / Team

Navigating a path through the small business landscape.

Back in 2007, we met while working together in the M&A due diligence group of one of the Big 4 accounting firms.  Due to a reshuffling of office space and renovations, we had the pleasure (and occasional displeasure) of sharing a 50 square foot office.  In these tight quarters, we bounced many business and investment ideas off one another and in late 2010, we decided to go in on our first investment together...a single family rental.  Though only one house, this was during the Great Recession – it was a scary time, banks did not want to lend, and there was no end in sight to foreclosures.  We did our research, challenged our thesis, and had the encouragement from one another to dive in.  After the first investment, we continued to grow our holdings and the experience solidified our conviction that the opportunity in private markets is immense, particularly when they are viewed as risky.  


With one side gig in full tow, we continued our professional services careers helping our clients buy businesses (ranging from Fortune 600 companies and renowned Private Equity funds doing billion deals to mom and pop owners looking to purchase local competitors for a few million dollars), but we were always drawn to the idea of investing in businesses ourselves.  In 2017, we found the right opportunity with Derek leading the purchase of a logistics company and Josh joining as an investor and advisor.  Despite working on over 500 acquisitions between us and being partners at separate accounting firms, we realized how different it is when you are on the front lines with your money on the line. We also learned how important people are to the equation and the value of partnerships. Every business is a collection of partnerships: customers, suppliers, employees and even lenders. Success occurs when everyone is aligned, the business has the right people to execute strategic plans and the money to do it.


So after a year of global change and uncertainty, we decided to start Cayne Crossing in 2021.  Breaking from the norm and pursuing your goals of buying, operating, and growing a business can be extremely intimidating and scary.  We have spent our careers helping people buy businesses and believe we can help you make your investment a success.  A good partner is there to give you encouragement when you need it, advice and tough love on hard decisions, and be a sounding board when you just need to vent.  We have been there, we have advised many buyers, and we want to partner with you.  

Meet The Team

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