SSS #260: 5 Years Ago...

Livin' La Vida Luna y Luca

We've unsuccessfully tried putting Luna on this Pumpkin Train every Fall for the past 3 years.

During our most recent visit, she agreed to stay on if Luca sat in the same car as her. We reluctantly put them in there expecting them both to cry as soon as the tractor turned on.

To our surprise they had a blast. Our little girl is growing up... with a little help from baby bro. 🥹

5 Years Ago...

I was at a bit of a crossroads personally and professionally.

On the professional side, I was still licking my wounds after a failed restaurant venture.

From 9-5, I worked as a property manager for my parents' 46-unit roadside motel.

In reality, I was my dad's personal assistant. When he said jump, I asked how high.

Back then, real estate was just a side hustle. I spent my nights and weekends networking with big-name local operators and helping fundraise for their deals.

It was fun and exciting, but not lucrative. If I was lucky, I'd make a 1-2% vig on any money raised.

I told myself I would learn the game from proven players before jumping in with both feet. I didn't want to get my face ripped off like I had in the restaurant business.

I ended up doing that for a little over 3 years. After a while, I realized I had to shit or get off the pot.

The truth was I was scared to take down my own deal.

.. Until we found out we were pregnant.

Around this time 5 years ago our fertility doctor called us with excellent news: our embryo transfer for Luna was a success.

After failing to get pregnant for years, failing at a startup restaurant, and a few other setbacks, things were starting to look up.

Documenting The Journey

People react differently when they find out they're going to be parents.

My reaction was quite visceral. My mantra became, "Kill the boy to become the man". Many of you reading this might remember that quote from Game of Thrones. Maester Aemon said it to Jon Snow in Season 5.

It's a little dramatic, but I really just felt like I didn't have my shit together and I was getting by on a little bit of charm and a lotta bit of nepotism.

My perspective and motivations changed. But that can only last so long. To hold myself accountable, I decided to publish a weekly newsletter.

It would be a public diary of sorts. Documenting what I'm learning and doing in real-time. It was a forcing function to get out there and do cool shit.

"To think is easy. To act is hard. But the hardest thing in the world is to act in accordance to your thinking."

-Johann Wolfgang von Goethe

Looking Back

For the 5th anniversary of this newsletter, I thought it could be fun to look back on some of my favorite posts.

I don't expect you to read all (or any) of them, but taking ~30 minutes to flip through a few pages of my diary was enough for me.

Maybe one of these email subject lines piques your interest too?

What I'm Working On...

Whenever You're Ready...

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