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Owned by Benjamin

Educating Cohorts of Main Street owners & buyers to preserve businesses, legacies, income & communities. Succession over Closure.

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10 contributions to Main Street Succession Academy
Clearing the Hurdles
IN both buying and selling businesses there are hurdles that can seem insurmountable. These hurdles regardless of where they come from, either real or imagined, can delay, stall or completely derail a person from continuing on the path to business succession and wealth preservation (or creation for that matter). What are some of the hurdles you have been through or saw others struggle with?
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Know when to hold em, know when to fold em.
Kenny Rogers sung one of my favorite songs of all time. My siblings still will just start singing it sometimes, especially when playing cards. It's a poker song but it applies to any gamble really. Selling too early or too late can be a gamble. Best to learn from someone who knows thw ins and puts of the he game. I just spoke to a buddy tonight who just carried his omma and grampa and now the in-laws are showing signs. I suggested we work on a succession plan now , before they need it in hurray. He likes that.
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The more your business needs you....
This is a subject about how transferable your business and its value is to your eventual successor be it a relative of your, an employee or 3rd party buyer. The more your business needs you, the less it's transferrable value will be. I was having a conversation last night with an older couple I know well, thay are in their 70's and have ran a Construction cleaning Service for over 50 years. They have paid off all their assets, their house and all but 80k in rehabs on their home. they can and do run on a shoestring and almost half of their 400k annual revenue goes to their employees. He has has had to step back recently due to battling cancer (and winning), she still runs the office side of everything. What can they do? Their owner benefit is actually a wage for her, she is currently not replaceable and as he stepped back their income has dropped because their oldest son has had to cover more, and they hired another worker. They may have $30k of pure owner profit. That's it. What would you do if you were them? hand it all over to the son and train a replacement for the office? or grow the business through your decades old connections, hire subs or crews to do the work and hire a management trainee to take over the office work? I explained that they are currently a Service Provider, they should expand and restructure to be a Managed Service Provider or maybe a Managed Service Organization. Increased sales and contract service providers to provide capacity (they know many whom they helped get started over the years). Manage the sales and back office, let providers provide, take a cut of all they work and then train others to run your office for you. This improves stability of the business, removers owner dependance and so increases value and actual owner cashflows. This of course would have been better to do years ago, but it wasn't on their mind. Better now than never. Succession over closure.
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1st Organic Seller contacted.
Just got off a call with a business owner who responded to my offer for free exit assessments. 20 minutes later, she was in tears (good ones). Not because I told her what she wanted to hear, but because someone finally gave her honest, strategic guidance about her biggest asset. She's been building her business for 15 years. Never thought about exit planning. Didn't know where to start. Now she has clarity, a strategy, and knows her next steps. This is why I do this work.
The 3 Exit Paths Every Owner Should Know About
The vast majority of business owners would love to see someone in the family to take the business over and run it successfully for generations. This is the most commonly imagined path to business succession (aka Plan 1) and sometimes it works great depending on the family members. I know of a number of 1st generation successes like this, but it is a small number, definitely not the number one way business owners DO pass on their businesses. In fact less than 30% of all businesses are ever passes down to 2nd generational family (in US and Canada), 12% to 3rd and less than 4% to the 4th generation due to many factors, one of which is lack of planning. The 2nd Path) Sale to a third party This method involves selling the business to an external buyer, such as a strategic buyer (a competitor) or a financial buyer (a private equity firm). It is often the preferred option for maximizing financial return and making a clean break from the business. How likely is it? - Low probability of success: Data indicates that only 30% of businesses GET LISTED for sale and only 18% of those actually find a buyer and successfully close the deal (that's 5.4% of all businesses) Many owners are disappointed by the outcome, whether due to a lack of offers, low valuations, or other challenges in the sales process. - Best for: Businesses with a strong track record of profitability, defensible market position, clear growth potential, and a management team that can operate independently of the owner. Many businesses again fail here due to poor representation and Lack of Planning. Plan 3) Close the doors and Liquidate. Sounds easy and safe to some, and Sadly it's THE MOST COMMON, and has MASSIVE DOWNSIDE for the owners and the community. The data shows that liquidation of community based business are not just bad for the seller but pose an agregated threat to every community they leave behind; For the owners liquidation provides: Downsides of liquidation for owners - Lowest financial return: Liquidation involves selling assets individually, which usually yields a far lower value than selling a business as a going concern. Goodwill, brand value, and other intangible assets are lost. Owners who sell to a successor can often receive significantly more, even through a structured buyout or installment plan. - Minimal funds: After paying creditors, the remaining proceeds for the owner may be minimal or non-existent. In a worst-case scenario, if the business is insolvent and the owner has provided personal guarantees, they may be held personally liable for debts. - Loss of legacy: For owners who have dedicated their lives to building a business, liquidation erases their life's work. Passing the business to a successor preserves the legacy, name, and mission they worked to create. - Reputational damage: Liquidating can damage an owner's professional reputation, making it more difficult to start a new venture in the same industry. - Loss of control: The liquidation process puts control in the hands of a liquidator, removing all decision-making power from the owner. 
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Benjamin Redmond
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@benjamin-redmond-6699
A natural Seattleite, Benjamin is adaptable, informed, confidant and mission driven. Ask about Creative Exit Strategies saving Taxes & Growing values.

Active 11d ago
Joined Oct 9, 2025
Monroe, WA 98272