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3 reflections from some very rich friends

Over the last couple of years, I’ve enjoyed watching some friends sell their companies and get really really rich. Like 9-figures rich. Many of these people I’ve known for years and so I’ve watched the build, the process to sell, the sale, and the aftermath.  3 reflections: Money motivation can lead to a lack of fulfillment Some of my friends have been very “money motivated” others, barely at all. What I’ve noticed is the more money-motivated someone is the less fulfilling the big payday seems to be. Frankly, for money-motivated friends, the big check can seem like a letdown because no matter how big the number is, it could have/should have been bigger. For my friends who have a different view of money, the insatiable desire for more is lessened. Make no mistake, these are very motivated and driven people, who are competitive and want big numbers, but by quantifying what “enough” actually looks like, fulfillment is more readily achieved.  Observation: notice where your motivation is because if it’s all pointed in an insatiable direction then you’ll likely struggle ever being fulfilled by all your hard work. 

Allow the business to become what’s it’s meant to be

None of my friends started their companies with a 9-figure sale as the goal. Instead, they had an idea, which turned into a company, and 20 years later a sale was the natural, and often surprising next step.

Observation: while focusing on the outcome can help prioritize, the reality will likely play out a lot different than you think so stay focused on 6-12 month objectives and allow the business to become what it’s meant to be. Bonus Observation: getting a really big payday has a lot to do with industry (tech usually) and market timing making it even more unpredictable. So don’t count on it.

Setbacks, how you view them matters

All of my friends have faced significant challenges along the way such as lawsuits, personnel issues, big client losses, public embarrassments. That’s par for the course in business. For some, setbacks were personally devastating, for others they were seen as part of the journey and not deeply personal. Different mindsets created different realities. Those who viewed setbacks as personal have been left with damaged friend and family relationships. Those who saw the setbacks as part of the process look back on the difficult event with gratitude for lessons learned.

Observation: how personal you view setbacks now will dictate your ability to move forward later.

I’m several months into building my brand in a new direction with many new opportunities on the horizon and so these observations really resonate with me. I hope you found them helpful as well. It’s all too easy to focus on things that don’t actually matter so cheers to enjoying the journey. And may we all continue to remind each other of the importance of that!  Like this blog? Please forward this email and take a look at others here.

All my best,


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