066. The Power of Being Prepared with Jay Gabrani

After his first child was born in 2005, Jay jumped into the world of real estate investing. Despite several challenges along the way, he built a multiple seven-figure real estate portfolio. That portfolio helped him take a multi-year sabbatical to deal with the heartbreaking personal tragedy when his wife passed away in 2014.

The experience lead Jay to reevaluate the purpose of his life during that sabbatical. Before his wife passed away, Jay thought he was financially prepared. After going through the experience of being the executor of his wife’s estate, he realized he wasn’t.

Today, Jay makes an impact raising his three children and empowering Fathers to secure their Family’s Financial Future as the founder of Prepared Fathers.

“How hard you work has very little to do with how well you retire. You are either Financially Prepared or Financially Negligent.”

-Jay Gabrani

He achieves this through his one-on-one and group coaching programs and his daily podcast, A Minute with Jay. He is also a frequent podcast guests on other shows and does a limited number of speaking engagements.

Key Points from the Episode with Jay Gabrani:

  • Jay Gabrani is the founder of a company called Prepared Fathers, to help fathers be ready financially for major, unexpected situations life can throw at us. This was, of course, borne of Jay’s experience as a husband and father.
  • Jay grew up in Canada, and took a trip to India to spend time with his grandfather, who instilled in him a desire to build his own business. He didn’t start that way, but built a path to be able to be an entrepreneur, working for himself since 1997.
  • In the early 2000s, Jay got married, bought a house and started a family. All at ‘hyper speed’, as he puts it.
  • His first business was a restaurant franchise, which he ran successfully for 13 years. He’s gone on to other ventures, including investing in real estate.
  • The biggest benefit of being an entrepreneur is the freedom and choice to design your life. He decides what time is for business versus family versus exercise, etc.
  • With three young children at home, Jay worked and his wife stayed home with the kids. In 2011, his wife slipped and fell, leading to getting prescribed Oxycontin to deal with the pain, which she soon became addicted to.
  • Along with the addiction, his wife was battling depression and pain, while Jay’s style was to snap out of it and do what you have to do (similar to my approach when my wife went through her worst in 2011, too).
  • His wife decided she didn’t want to live, and took her own life in 2014, leaving Jay and the kids behind.
  • Overnight, Jay became a single father of a a 5, 7 and 9 year old kids. He used his real estate investments to fund taking a sabbatical from working so he could focus on his kids. He expected that to last a year, but ended up being a four year period.
  • The devastation is not something he feels you can ever fathom until you’re going through it.
  • Being a professional accountant, Jay expected he would handle being the executor of his wife’s estate to be easy. He quickly realized how mistaken he was. From not knowing her passwords, where the key was to her safe deposit box and more.
  • And he realized how much worse it would be for his wife if he was the one who had died since she knew even less about the things an executor needs to know than he did.
  • That woke him up to the need for a little bit of planning, a little bit of preparation. He says his company’s mission is to help fathers plan for life’s little curve balls.
  • My reaction was that this is all right, but easier said than done. Having these conversations is hard. People don’t like to talk about, “What would happen if I/you died?”
  • Through his tragedy, he realized he could help other fathers avoid that. There are a lot of fathers in trouble for various reasons, and he can help solve that.
  • It’s not about money, it’s about skills. If you lack the skills you need for what you’re facing, go and acquire them. Look at how you’re spending the resources you have (time and money) and see if you can spend those resources in a way that moves you forward.
  • There are some basics to be sure you have in place that don’t have to cost much, like wills and basic life insurance. A $250-500K life insurance policy would have made a tremendous difference for him and his three young kids when his wife died, and not having it put his family at risk.
  • The most important step, and likely the hardest, is the conversations. Not just between the two parents, but key others like parents, siblings, step-siblings or step-parents, etc. Doing that work up front will make things smoother and better and give you a sense of release.
  • We got into how you can have these conversations as it can be really hard. I shared my own struggle with my wife to have this talk, especially since there was a scare around her survival. Jay enlightened me with another approach.
  • Rather than making it about doom and gloom and the fear of being stranded, appeal to the family or the children. For the sake of the children, let’s talk about this. And once it’s done, we don’t have to do it again.
  • He suggests getting all the papers in order and together in one place, and then having the conversation focused on “here is where you find everything, in place.”
  • Jay put together a checklist for the key things you want to have in place to be prepared that you can get for free at preparedfathers.com/day
  • As fathers, we often feel a need to be a provider and protector, If we don’t have these things in place, we aren’t really providing or protecting our family.
  • And this transcends gender-stereotypical-roles. For any parent, this is a truism. We are leaving our family unprotected and unprepared.
  • Jay shared a brilliant thought that feels like it’s at the heart of this entire show – in order to impact the world, you have to take the worst moment of your life and convert it.
  • For him, that message is even more important because his kids are watching, and he owes him this.


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