Late Checkout - My 2022 in review… finally
Before we dive in: Podcast New episode of the pod is live with Twitter legend Trung Phan. We talk his new AI tool, why the Hustle bred major talent and who should buy TikTok (and why). Listen on Spotify, Apple and watch on YouTube. My video editor really liked this episode (lol). Community College Enrollment is now open for Community College. It’s our masterclass to teach you how to build products communities will love. You’ll learn how to mine places like FB Groups/Reddit to build million dollar ideas. This course sells out 100% of the time. And this time we’re including a free landing page for your brand so seats will fly. Check it out here. Class starts April 3rd. P.S: Most people expense the course through their company. Invest in yourself and let them pay ;). Ok - let’s get in today’s weekly post! Who said it’s too late to do a 2022 review?I realized that I laid out my predictions for where the internet, AI, and social products are headed in 2023… but I haven’t written down my full thoughts on the best wins and lessons from 2022. Sharing is caring and I hope that this post will encourage you to be reflective on your 2022. In rapid fire order: Biggest changed outlook of 2022: What retirement means What is retirement? Typically, it’s the moment at an older age where we have enough money to stop working and enjoy the rest of our lives. Days are spent golfing, on the beach, and any hair you have left is gray. In 2022, I started thinking about retirement differently: If you’re doing what you love, you’re retired. Period. If you’re spending your time the way you want to be spending it, you’re retired. Full stop. I don’t see myself getting old and taking up golfing. I want to write blog posts forever, record podcasts forever, run my agency/studio/fund forever. To me, it feels like I’ve achieved retirement — and I think we need to rebrand that word to mean “spending your days doing what you love.” There is no mythical end point or goal that I’m trying to hit and that is a peaceful feeling. Most underrated company of 2022: Zapier Zapier already has a valuation of $5 billion — how could they possibly be underrated? The ability to automate anything is increasingly valuable with the advent of AI. ChatGPT is already an incredible tool, but AI + automation could have incomprehensible power. AI and Automation is how we’ll get the world’s best salesperson. For example: a new client is added to Salesforce, Zapier sends it to Slack, and ChatGPT automatically follows up with the client in a personal way. There's a lot of interesting things that you can do with AI automation and generative AI — and that’s why, despite Zapier being a $5 billion company, I actually think it's underrated. Best decision I made in 2022: Continue doing the Where it Happens podcast Last year, my co-host, Sahil Bloom left the podcast to focus on writing his book. I could have easily given the pod up, but instead I asked myself:
This is a powerful question to ask yourself at moments of crossroads. So, I went ad-free (and removed our $360k/year ad sponsors) and changed the type of guests to be less VCs more people who are in the trenches in community/creators/commerce. And it’s been a blast. If you’re thinking of starting a podcast, do it. It’s an incredible way to have interesting conversations while letting people learn about you. Bonus best decision of 2022: Not selling my baby to Twitter I wrote about the time Twitter tried to buy Late Checkout with a healthy 8-figure offer last week. You can read more about it here. Worst decision I made in 2022: Not setting enough deadlines One of the things I learned in 2022 was I noticed that if I told the designer, “Hey, design this landing page in two weeks” — they would design the landing page in two weeks. If I said I needed it done in one week, it would get done in one week. This phenomena is called "Parkinson's Law". The law says, work expands to fill the time you give it. So, if you give someone a long deadline, they might take their sweet time even if they could finish quicker. But, if you give them a short deadline, they tend to work more efficiently and finish faster. That's because a tight deadline can motivate and focus them, leading to greater productivity and efficiency. Now, you don't wanna put too much pressure on your teammates — that's not cool at all. Keeping track of how long certain projects take and holding your team accountable to a deadline that’s just a little bit uncomfortable is the sweet spot. You don’t want to rush greatness, but you want the results in your hands when they’re ready. If I would've set more deadlines in 2022, I think we would've built and launched more products, and this was only something that I really got more stern with towards the end of 2022. My favorite YouTube channel of 2022: Hodinkee Hodinkee is a media company and app that focuses exclusively on luxury watches. They’ve got a show called Talking Watches, where they sit down with famous people and — you guessed it — talk about watches. You get to hear personal stories from these celebrities about their watch collection, why they bought certain watches, what the watch means to them. My favorite episode is with John Mayer. Hodinkee is a blueprint for what starting a community-based modern media company looks like. Billionaire of 2022: Mr. Beast Even though he doesn’t yet have a billion dollars cash, I think Jimmy will be one of the top 10 wealthiest people in the world by the time he’s 45. He’s 24 now. He has the biggest YouTube channel, and he’s growing the fastest of any creator you can think of. We’ve seen his ability to incubate products that resonate with his fans in 2022, like Feastables and Mr. Beast Burger. Creators who can create real brands are already in a perfect spot — but Mr. Beast will reach a new stratosphere of status and wealth. Best product I bought in 2022 under $150: YouTube Premium I’m obsessed with YouTube. I watch it every single day. I would take YouTube over TV any day of the week. I learn so much there. The YouTube experience with no ads (especially if you listen to podcasts) is so good. It’s a seamless experience, and I love it. Biggest health win of 2022: falling asleep In 2020, 2021, I started having a rough time falling and staying asleep. It made me a real-life zombie. I needed to change that in 2022 for my health (and sanity). Thankfully, I got sent Beam because they sponsored our pod, and it’s been a game-changer. It’s a tasty hot cocoa drink, that I drink 30 mins before sleep. I fall asleep and stay asleep like a baby. I’m obsessed with it. I asked them for a high discount code for my subscribers and they gave me one! 40% off a subscription that you can pause or cancel anytime or 20% off a one time purchase. Here it is (promo code is Gregisenberg). Happy sleeps! Most unexpected ROI of 2022: stop letting my push notifications push me around In 2022, much to the chagrin of people trying to get in touch with me, I’m mostly on DND mode. I didn’t realize the mega positive impact this would have on my personal life and business. Most inspiring book of 2022: Based on a True Story: a Memoir by Norm Macdonald This is a non-business book. It’s a comedic masterpiece memoir and had me cracking up. It's intriguing to see how Norm blends fact and fiction, blurring the lines between reality and his own creative spin on the truth. It inspired me to be more creative, take more fun adventures and be more playful. You must listen to it as an audiobook because Norm recorded the whole thing. Norm passed away in 2021. We in startupland can learn a lot from the great comedians. We’re in March now, but let me know what your favorite things and lessons learned were from 2022! I’d love to hear them. Be well, When you’re ready, there are 2 ways I can help you:
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