I grew up watching the original rainmaker—my dad. He started at New York Life Insurance in the old-fashioned way: knocking on doors in apartment complexes, selling check-o-matic life insurance plans one at a time. Most people would’ve given up after the first hundred slammed doors. He didn’t. He once made 100 phone calls and got 100 “no’.s” But the 101st call was a yes. He kept going.
At the same time, he was constantly afraid of being put out of business. That fear drove him to save relentlessly. By the time he retired, he was a multimillionaire—not because of extravagant deals or lucky breaks, but because he lived below his means, took nothing for granted, and worked every day as if the whole thing might vanish.
My dad was a natural extrovert. He loved people. He could strike up a conversation with anyone, anywhere, and he always left them smiling. I admired that, but I didn’t feel like I had inherited it. I was more introverted. I was comfortable in my own thoughts, in quiet spaces. My first career was as a middle school science teacher—hardly the proving ground for rainmaking.
But life has a funny way of pushing us out of our comfort zones. When I transitioned into financial advising, I thought the hard part would be mastering investments, tax strategies, and financial planning. Turns out, that was the easy part. The real challenge was rainmaking—learning how to connect with people, build trust, and open doors.
From Teaching to Rainmaking
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