His Father Meant to Finish the Plan. Pleasant Randle Helps Families Finish Theirs

Pleasant Randle IV was seventeen when his father died.

About a week and a half before, an insurance agent had come by to talk through protecting the family. His father wanted to think about it. He already had coverage through work, and when he passed it took care of what the family needed. But the fuller plan the agent had laid out, the one that would have left everyone in a better spot, was never put in place. There had been time for the conversation. There had not been time to finish it.

That gap is what Pleasant built his work around. Sometimes it is a death that makes protection feel real. More often it is a new baby, or a marriage, the moment the people counting on you suddenly have names. It is just a plan that stayed a conversation, the protection a family means to finish and never quite does. His job is helping other families finish theirs while there is still time.

Today he is the founder of Pleasant Power Insurance Group, a Cleveland firm, and he has been licensed since 2012. Ask him what he does and he keeps it plain. “Life, health, and wealth,” he says. “I want to sit down and have a conversation.” What he offers, in his own words, is clarity and peace of mind about the things most people would rather not think about.

Here is what that looks like. It usually starts with a burial plan, so that when the day comes, the people you love are grieving instead of standing in a funeral home working out who can cover the bill. From there it can grow into life insurance, retirement, and living benefits. “A lot of people don’t know you can take advantage of insurance while you’re still alive,” he says. If you got sick and could not work, it can put money in your hands while you are still here, not only leave something behind for the people you love.

Whatever you have, the point is that your children are not left with a mess: a plan instead of a court process. For families with more to pass on, he also coordinates the estate and financial side through advisors and estate attorneys you can sit with, at no cost to you. The word he keeps coming back to is legacy: that the people you love are taken care of, not left carrying it.

The part that matters most comes later, when a family actually has to use what they put in place. They are not calling an 800 number and explaining their life to a stranger. They are calling Pleasant, the person who already knows them, and he handles it from there. He is not tied to a single company either, so the plan gets built around your family.

He has already seen what that looks like from the other side. The first death claim he paid out went to someone who later told him it let them take care of their children. That is the moment all of this is for, when a plan a family meant to finish becomes the thing that holds them steady.

This is hard to talk about, which is one reason Pleasant is also a standup comedian. A little humor makes room for the honest talk underneath. He sits with a family, lays the options out straight, and works it through with them until the way forward is clear, while it is still theirs to make.

If protecting your family has been something you keep meaning to get to, this is where it starts. The first conversation is free, and the pace from there stays yours. As Pleasant puts it: “The best two times to get something done is now. And right now.”

Pleasant Power Insurance Group 

(216) 327-3787

pleasantpowerins.com