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The Highest High, the Lowest Low
The first $250,000 to start the business. Someone believing enough in the idea. Attracting really strong players around me has been incredibly validating for me. Getting stabbed in the back by the people I started the business with because they would have rather gotten their money out than seeing the company move forward. A hostile takeover attempt that aligned a bunch of my early shareholders and his co-founders around exiting the business to a big multinational. The saddest part of that is how people sacrifice their own character and sense of what was right and wrong.