Hey there!

I hope you’re having the most amazing start to the week. The NFL season is officially back and I’m writing to you about something better than my Jets starting the season 1-0 and winning their first week one game in almost a decade.

Last week, I officially retired my mom.

It has been one of sweetest, most incredible feelings I’ve ever experienced and to see her smile and cry tears of joy for almost a week straight is a feeling I’ll never forget.

I lost my dad in my arms when I was 19 years old. He had an unexpected heart attack in my arms two days before Christmas. I lived in the farmlands of Connecticut and it took nearly 30 minutes for the fire department to come to try to save him. They coached me how to do CPR over the phone and they got there too late.

From that moment, I immediately became the man of the house and have been dreaming of the day I got to tell my mom, “I got you and you don’t need to work anymore”, my entire life.

In a flash, I went from a sophomore in college whos parents visited on the weekend to the kid who lost his dad on Christmas and immediately became the person his family looked at when something was needed. Bills, planning, working 40 hours a week through college, trying to hold it all together, while listening to sad music in his dorm room. That was me. All hoping I’d be able to do this one day.

I always knew it would happen. Just not this soon.

Not at 33 years old.

And for that, there comes some fun and hard conversations that are needed to be had. Even during a moment that should be one of the greatest moment of your life.

I've been carrying this job now for fourteen years, trying my bet to fill the void my dad left. My parents were together for over forty years. She had a husband and a plan that the two of them had built since grade school. And then you wake up one day and realize the plan for your life is gone overnight and so is your best friend.

I was handed one of the worst jobs in the world as a 19 year old kid and I’m damn proud of how my brother and I have showed up in all the moments, the good and the bad.

So last week, when I told her she never has to work again, I wasn't only doing something nice for my mom. I was finishing something my dad started and never got to finish. I did the thing he would have been the most proud to have of done himself. So I guess that’s the closest conversation I’ve had with in fourteen years, outside the morning of my wedding day.

This week we are upgrading her and getting her a brand new apartment. A beautiful new spot, with the bathtub of her dreams and a few minutes closer to the ocean. Right next door to her her favorite restaurants and bars that frequent some incredible Grateful Dead and Steely Dan cover bands.

But let me tell you, if you haven’t had this conversation yet with your parents its a doozy and doesn’t come without some incredibly hard and honest conversations. What you’re trying to do is not only a nice gesture, its planning the rest of somebody’s life. So we built out an entire plan, the monthly allowance, the spending, and tried to get close to the real numbers as she prepared for the day where she no longer had to wake up to an alarm clock.

Sit with that for a second, because I have been sitting with it for about a week now.

If she lives the way I am praying she lives, I just took financial responsibility for a stretch of time longer than I have been alive on this planet. I'm 33 years old. I'm underwriting something longer than my entire existence, using numbers I built two weeks ago.

I did this before I "made it” because I want her to have a better life. Before the house, before some things that would make my financial advisor nod and say "yeah, that's a safe decision."

I did it earlier than I may should have because I’m so confident in what we’re building. The Founders Club will be my last company and every day, every member, every life changed it becomes more crystal clear that my kids will one day be applying to join this thing.

But it still doesn’t take away the fear of the unknown. My life is going to change. My expenses at 33, are not my expenses at 38 and I know that to be true. What if the math I built when I sat down with my wife to “crunch the numbers” turns out to be completely wrong?

And to make matters worst, there's the biggest unknown, which I did not really think about until we pulled the trigger. What does she do with the 40 to 50 hours a week that used to be occupied with work? It stresses me out. Not just the aspect of how many of those hours will now be spend shopping, visiting coffee shops, but more about the concept of having a purpose and a reason to wake up every day.

Outside her relationship with her husband and children, work has been her structure. Her identify. A reason to get out of bed in the morning and fall asleep a little earlier at night, knowing you have to wake up and conquer the next day. I just removed all of that from her life overnight and handed her a calendar with a nothing on it, and called it a gift.

Does the budget we set actually hold, or does free time quietly become the most expensive thing in her life? Not because she's irresponsible, she's the opposite, but because a person with forty new hours a week finds new things to do with them, and most new things cost money. Lunches. Trips. The grandkids from my side that she doesn't have yet. I can't project what I don't know.

The fear isn't that the business gets tight. Businesses change, things get tough. Thats life and inevitable. I've been down to my last dollars before and I survived it.

The fear is that I have to sit down across from my mother, in the apartment I just moved her into, and tell her the money has to stop.

That's it. That's the whole thing keeping me up at night these days.

Not bankruptcy. Not losing the company. The act of un-retiring her. Looking at the woman who worked her entire life so that I could have a shot, and telling her I made a promise I couldn't keep. Being the second man in her life who ran out of time, for a completely different reason, but with the same result.

I guess this is just me pouring my feelings out and being a bit vulnerable. So if you’re still reading, let me say I appreciate you for hearing me out and I hope this has been useful for you. I read each and every response back to these newsletters, so if you’ve been here before and have any tips on budgeting for a parent or any advice from a similar situation, I’m all ears.

With that, I’m heading offline and about to attend the largest mastermind we have ever hosted in Los Angeles. Over sixty people will be driving from all over the city to meet up for four hours of networking, learning, and becoming a better version of themselves.

Whether this was your first newsletter or you've been reading for years, thank you for getting this far down. Thank you for reading. Thank you for caring. I don't take it lightly that nearly fifty thousand of you read this every single week.

And I mean it about the replies this week. If you've retired a parent, or you're saving toward it, or you've had the version of this conversation I'm dreading, I want to hear it. Or even if you’re just going through something and want to say hi. Believe it or not, I'm an inbox zero guy and I read every single response.

All the love in the world,

Chris