Articles Ranking
The longest-running businesses in the database, oldest first
A Calgary litter route from 1981, a $700 junk truck from 1989, a striping crew from 1999. Thirteen owners still running the business they started or bought ten or more years ago, oldest first.
Thirteen of the 33 owners in the database have run the same business for ten years or more and still run it. This page ranks them by the year they started or bought in, oldest first. The year comes from each owner's entry, and the length in years is our arithmetic against 2026, so treat it as approximate.
Revenue figures are as each owner reported them and are not all alike: franchisors report systemwide sales, and some owners report gross. The margin ledger covers what each trade keeps.
Started part time in Calgary in 1981 with about $250 of hand tools. On a 2024 podcast he put the business at $600,000 to $700,000 a year, and he still walks the properties. About 45 years.
Bought a $700 pickup at 18 and started The Rubbish Boys. Rebranded as 1-800-GOT-JUNK? and began franchising in 1998. Around $600 million systemwide in 2024 across 100-plus markets. About 37 years.
Rolfe bought his first park for $400,000 in 1996, four months after selling his billboard company. Reynolds joined him after they met in 2006. The portfolio is reported at 250-plus communities in 25 states. About 30 years in parks.
Luke was 19 when he bought striping equipment and started in Rochester, New York with Heather. 1-800-STRIPER approaches $739,000 a year in gross revenue and now franchises. About 27 years.
Graduated into the 2008 recession and spent $300 on used tools, including a $50 mower. Plan-It Vision now does $22,000 to $29,000 a month in Seattle at roughly 30 percent margins. About 18 years.
Launched Scoop Soldiers in McKinney, Texas in 2010, four years after McCoy formally founded his lawn company. About $1.25 million a month systemwide by 2023, across 96 franchised territories. About 16 years.
Bought a failing laundromat off Craigslist for $85,000 in 2010 after 25 banks said no. Queen City Laundry now runs four Cincinnati stores reporting over $2 million a year. About 16 years.
Bought Gray Brothers from his father-in-law in 2013 and grew it from about $1 million to about $3 million within two years. The company itself dates to 1929, the oldest in the database. About 13 years under Spracklin.
Bought a struggling Parkland, Florida wash for roughly $3 million and opened in April 2013. Rising Tide now runs three locations, washes close to half a million cars a year and reports nearly $6 million. About 13 years.
Paid $60,000 for an existing Tampa Bay route in 2014. Hill Vending grosses over $58,000 a month from more than 100 machines, and he typically works two days a week. About 12 years.
Founded Augusta Lawn Care in Blaine, Washington at 18 after canceling a medical school application. Franchising since 2019, now 200-plus locations and over $50 million systemwide. About 12 years.
Started Queen Bee Cleaning with about $5,000 in 2015. Now Bumble Bee, at $120,000 to $140,000 a month and more than $5 million cumulative, with a second market in Atlanta. About 11 years.
Spent about $5,000 on equipment in Nashville in 2016. Passed $1 million a year within about four years and reported about $2 million a year in 2023. About 10 years.
Not ranked
Sold. Nick Huber and Dan Hagberg started Storage Squad in 2011 and sold it to 1-800-PACK-RAT in January 2021; they now run Bolt Storage. Sam Evans started You Call We Haul in 2016 and sold it in September 2024. Both businesses lasted long enough to qualify, but neither founder still runs the one he started. The exit ledger covers what those sales are known to have fetched.
No founding year on record. Daniel Tom, Clayton Roll, Brannon Fowler and Alan Tursunbaev have no start year in their sources, so they cannot be placed. Neither can Dan Burnside, whose HVAC purchase ended in bankruptcy.
What the list shows
The oldest businesses started with the least money. Winch began with about $250, Scudamore with a $700 truck and Kokenge with $300 of used tools. All three sit near the bottom of the startup cost ladder. A small start does not cause a long run, but it does mean the owner never had to survive a large loan in the early years.
Most of them sell a service that comes back on its own. Litter reappears overnight, parking lots need restriping every 18 to 24 months, dogs produce waste weekly, and clothes get dirty in every economy. Each of those trades scores 91 or higher on the Boring Index.
Nearly all the long-runners ended up teaching or franchising. Winch sells his Cleanlots manual, Scudamore and the Menears franchise, Rolfe and Reynolds run Mobile Home University, McCoy franchised Scoop Soldiers, and Menz wrote a book. Our piece on the second business inside the first looks at what that income is worth next to the operating business.
New readers can find the rest of the database through Start here. This site is one of SideRoad's weekly builds, and owners move onto this list when their entries cross ten years.
Common questions
What is the oldest business in the Boring Millionaires database?
Under one owner, Brian Winch's parking lot litter business, which he started in Calgary in 1981 and still runs. The oldest company is Gray Brothers, a septic business founded in 1929 that Dan Spracklin bought in 2013.
How many documented owners have run their business for ten years or more?
Thirteen of 33, counting owners who started or bought in 2016 or earlier and still run the same business. Two more, Nick Huber and Sam Evans, reached that length but sold the business they started.
Do the longest-running businesses make the most money?
Not necessarily. Brian Winch reports $600,000 to $700,000 a year after more than four decades, while Joshua Brown reported about $2 million a year in 2023, seven years after starting. The largest figures on the list are systemwide franchise sales, which are not owner revenue.
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