Caleb’s Newsletter

And just like that … it’s December! Is anyone else wondering where this year went? 

I spent time with my family in North Carolina over Thanksgiving. Going home is nice for many reasons – it’s grounding, slower-paced, more relaxed. It also reminds me that I created a life for myself outside of small town North Carolina. It’s surreal.

I’m extra appreciative of the time at home since I’ll be in Australia for Christmas. It’s summer there right now so it’ll be nice to briefly escape the New York winter. 

I’m still figuring out how to survive the cold-weather months in NYC but I do two things that help: I take a Vitamin D supplement and I plan at least one trip somewhere warm. There were many years when I couldn’t afford to travel; I haven’t lost sight of that and am very grateful to be in the position I’m in now.

Another not-so-recent update, but something I haven’t talked about much, is that I started taking acting and improv classes! I’ve even done stand-up open mic nights. Getting on stage and trying to make people laugh is the scariest thing I’ve ever done (and I’ve done some blood-rushing things!). 

I like that feeling, though – that feeling of discomfort and a little bit of fear. It means I’m challenging myself and stepping out of my comfort zone. I don’t ever want to get complacent or feel like I’ve “made it,” so this is a small way to keep myself on my toes. Plus, at the end of the day, I’m an entertainer. And these classes will help me become a better entertainer.

By the way, I hear crickets the entire time. My very first stand-up, I didn’t get one laugh. Not a single one! I now consistently get at least one laugh. But it’s a lot of crickets.

In case you missed my recent content …

I toured Toni Breidinger’s training facility! Toni is a professional race car driver making it in a male-dominated profession. She’s a certified badass. 

I saw her on Instagram, shot her a DM, and we planned the tour around my trip home. She moved from California, where she grew up, across the country to North Carolina because that’s the center of NASCAR. She’s dedicated her life to this profession where the odds of succeeding are slim – and even slimmer as a woman. 

Here’s a throwback video for you to get you in the Christmas spirit! 

I love this home tour from last year. I was in San Francisco with my buddy Bobby and we just went up to the front door of this house decked out in holiday decorations and knocked! 

It’s an older couple who live there and they had never seen my videos and had no idea who I was. I introduced myself and asked for a tour. I couldn’t believe they said yes! The whole time I was filming I was thinking, any second they’re going to kick us out! But they never did. It still astounds me today. 

Ask me anything!

Anything at all! Shoot your questions to [email protected] and I’ll pick one each week to answer in the newsletter.

This week’s question: How do you work up the courage to talk to strangers and ask them things like, “can I tour your home?”

For starters, I’m always super nervous in those situations. But then I remind myself of the worst thing that can happen: they say no. Sure, that stings. It always hurts to be told “no” in any situation but then you move on and keep asking until you hear what you want to hear.

I’m also very aware that asking a stranger to let you in their home is a big ask – and a bit weird. So I try to set myself up for success as much as possible by being super friendly and showing them that I’m genuinely curious.

When I first started this series I heard about 100 “no’s” before someone said yes. When you think about it, that’s not bad: Imagine if the thing you most wanted, all you had to do was ask or do something 100 times to get it. You’d do it. 

Bonus question: What is one thing you can’t travel without? 

A neck pillow. It’s annoying to carry around but a necessity.

This week’s listing!

To give you guys an idea of what’s currently on the rental market I’m going to start including some listings in the newsletter. It’s considered “low season” right now, meaning prices are at their lowest (but there’s less supply, since less people aren’t moving as much in the winter, meaning less apartments are freeing up).

As a general rule, the further you go out of Manhattan, the more bang for your buck you’re going to get. Jersey City, which is just across the Hudson River, is growing in popularity for this reason. It’s an easy train ride into the heart of the city, you have access to beautiful Liberty State Park, and it’s right on the water.

Here’s a two-room, two-bath $1,725 apartment in Jersey City (with a fireplace!).