Sales: The Boomer Entrepreneur’s Main Hat

Jon Obermeyer
2 min readOct 30, 2018

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Let’s say you just retired and you’re launching a start-up based on your industry experience or professional expertise. There’s a big giant hole in the market, and you are going to fill it rather than drive an RV across Route 66 with your bride or play 36 holes a day and lower your handicap on the links. Perhaps you’re going to launch a consultancy or a speaking business, to supplement your retirement income.

If your career was mostly spent in corporate settings (a multinational enterprise, 100-employee company or even a law firm), then you need to get used to wearing many hats, including sales.

As an entrepreneur, sales is probably your top job.

Sales is not only about converting prospects into paying, loyal customers. Even when you are talking to investors, bankers and prospective employees, you are in selling mode.

If you have sold previously, it’s time to learn sales as the entrepreneur. More is on the line, and you will have fewer resources than you did in corporate sales. You may not have a large brand behind you or deep pockets to fund a marketing blitz in order to enter new territory. You may be selling a novel product or service, no one’s ever heard of.

If you have never held a formal sales job, don’t worry. You’ll learn. You’ll figure out. Sales is a one-on-one conversation, and a transfer of enthusiasm. It’s no more complicated than that.

Plan the work and work the plan. Let the magic happen, often times completely out of your control. Accept that you have power over nothing. You’ll become an expert soon enough.

Note: these posts are excerpts from the forthcoming book “60 Rules: The Retirement Entrepreneurship Roadmap.” (2019, Tomol Press). If you are in your 50’s or 60’s and planning to launch a business as a retirement hack, hedge or wealth-building entity, please reach to me on LinkedIn and share your story.

Photo Credit: Mike Cohen

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Jon Obermeyer
Jon Obermeyer

Written by Jon Obermeyer

Jon Obermeyer is a CA-based poet, fiction writer and memoirist who has independently published over 30 books of creative work on Amazon.

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