If you're new here, welcome to Never Enough, where I brain dump interesting stuff that has been on my mind over the last week.
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Now onto this week’s issue…
I started wearing makeup. Kind of. I’m almost forty, and the thing I always thought I wanted to happen, has happened. I’m starting to look old. As someone who didn’t have armpit or facial hair until the age of nineteen, I’ve always wanted to look older. But over the past few years, I’ve started going gray. Losing my hair. Seeing crow’s feet appear near my eyes, and I gotta say, I’m not a fan. It’s not the end of the world, but I’d prefer not to go bald and have my face slowly turn into a catcher’s mitt. This year, I vowed to start paying attention, and decided to do what I could to age gracefully. One of the easiest things you can do to reduce skin aging is to wear facial sunscreen. So, I bought some and started applying it every morning. Oddly, on the days I wore it, I kept getting compliments. My girlfriend would tell me I looked extra handsome. My friends would ask if I was doing anything different. I’d look in the mirror and think I looked better than usual. It turns out that I had accidentally bought tinted sunscreen. Sunscreen that had a bit of color in it and evens out skin tone. Kind of like a foundation. I started wearing makeup without even realizing it. And I loved it. It’s such a great aesthetic hack and I feel like it’s one of those things that I never really registered that most women were doing. It’s time to level the playing field, gentlemen. This is the one I use: La Roche-Posay Anthelios Ultra Fluid Tinted Sunscreen.
What does it feel like when a wire transfer for tens of millions of dollars hits your bank account? Kind of weird, according to Marshall Haas, who came on my podcast in a semi-shellshocked state the day after he’d just sold Somewhere(formerly Shepherd) for $53 million dollars. It’s a fun interview. YouTube/ Spotify / Apple Podcasts
I’m a bubbling pot of stress today and, as I think about it, I’ve realized that it’s entirely because of my calendar. Nothing overwhelms me quite like a packed calendar. It’s my white whale. The thing that I have never been able to tame or conquer. I’ve tried a bunch of different strategies:
2-3 hour booking window: Results: booked 4+ months out, important company issues or CEO calls get jammed in at the last minute, leading to 4-6 hours a day of meetings and no deep work.
No calendar at all, just calling people: Results: massive call list I can never get on top of, and many people get offended when I won’t book with them.
Using Calendly: Results: a lot of unwanted meetings booked into eternity.
I’m at the point where I’m ready to declare calendar bankruptcy and I want to tap you, my audience’s, collective intelligence. The core issue is that I am an inch deep and a mile wide. I oversee over 40 companies, I have hobby businesses, I’ve got 150+ minority investments, I’m trying to do a podcast and this newsletter, I have a broad ranging, highly extroverted social life, and I’m a father of two who often has to travel for work. TLDR: My ambition exceeds my time. I’m curious to hear from other people who nod along with this and have significant work and personal responsibilities. How do you handle this? How have you prioritized? How do you delegate some of this? Please respond to this thread on Twitter if you have any ideas (systems, delegation workflows, heuristics, etc), I’m all ears!
Negotiating is miserable. The last thing any of us wants to do is spend their afternoon calling their cable provider to negotiate ten bucks off a month, even if we know we’re probably being ripped off. That’s why I LOVE this startup I just found called CostCutter. You upload your bills, and they negotiate them automatically (I believe an AI voice agent calls and negotiates on your behalf). The future is terrifying, but this is one innovation I’m excited about: RoboNegotiators.
Easy choices will ruin your life. I’ve observed this time and time again. Leaving the wrong person in the job because they’re your friend. Staying in a toxic relationship out of fear of being alone. Hiring someone mediocre because you need someone ASAP. We’ve all been there. I’m fond of this saying, which sums it up well: “Easy choices, hard life. Hard choices, easy life” – Jerzy Gregoric Today, I saw this illustration, which nails it.
Giving your business baby to a foster parent is scary. So, last week I went on My First Million and spent an hour sharing everything I know about hiring, transitioning, and managing CEOs. Enjoy. Here’s the episode on YouTube
Two Asks:
I’m coming to Austin and New York June 10-15 to record some podcasts to promote my book. If you know any podcasters with a huge audience (top 500 podcasts) based in either city, please intro me!
I’m trying to get the finance teams across all of our companies to start utilizing AI tools. If you know somebody who trains/implements teams on AI tools, specifically in finance/accounting, please send me an email :-)
That’s all for this week…but one more thing. If you’re enjoying this, can you do me a favor and forward it to a friend? Thanks.
