Find Your Tribe

June 18, 2024

If you are reading this, the chance is high that sometimes you look around and wonder if it’s all worth it. Whether you are thinking about leaving your job and taking the leap into entrepreneurship for the first time or are deep into scaling your company, you tend to think differently than those around you. You see opportunities where others see roadblocks; you know that there is greatness inside of you waiting to be unleashed, and you walk a different path than the well-worn road of normalcy.

Let’s face it. The entrepreneurial path can be pretty damn lonely. Your parents may not understand why you wouldn’t just get a safe job with a 401k; your college friends don’t understand why you no longer meet them for drinks on weeknights. Even though you are often surrounded by people, you are the one who has to have it all together. If you lose your head, the whole ship goes down. There is a baseline stress level that you just can’t seem to turn off and eventually normalize as part of the game.

You’ve chosen to live life on your own terms and be the captain of your own destiny. But as your success starts to scale, the world seems smaller and smaller. Everyone says that they want to see you succeed, but the more you do, the more their actions say otherwise.

Your problems are not normal problems. If your assistant quits and leaves you with a flooded inbox and a wave of overwhelm, when you try to explain this to your non-founder friends, you are most likely met with the world’s smallest violin.

This was my reality in 2016. Five years earlier, I had started my company with a dream, a plan, and just a little sprinkle of delusion, and somehow it had worked. But despite my external success, I felt very much alone. Sure I had lots of friends, but deep down, they didn’t get me. Even though I had built a solid network in the oil & gas industry, I felt like I lived on a different planet than most of my peers.

Then, something happened that would take me down a road I could never imagine. At the bottom of Tim Ferriss’ Five Bullet Friday email, there was a short note that said he was speaking at an event in Denver. I was a huge fan of his podcast and figured it would be fun to see him speak and perhaps get a chance to meet him and thank him for the inspiration.

I clicked the link and was surprised to find it led to an application form. I filled it out and booked a call with the organizers. When we spoke, I told them that they didn’t have to sell me – I was already in and would buy a ticket. They laughed and said that not everyone was a fit for the event and asked me a few questions about my revenue and business goals. I was skeptical but answered truthfully, and luckily, we hit it off, and I booked a spot.

When I showed up, I had no idea what to expect, but I figured it was probably going to be sport coats and nametags like the oil & gas conferences I had been to. Luckily, I was in for a surprise. I met all kinds of people from all kinds of industries, from e-commerce to SaaS to tech startups. I met bestselling authors, internet celebrities, and all kinds of interesting, slightly crazy, outside-of-the-box thinkers. I was hooked.

It was at this first event that I met Hollis Carter. His long hair, long beard, and painted toenails gave more hippie than business vibes, but I was starting to learn that looks could be deceiving outside of the buttoned-up private equity world. He told me he ran something called Baby Bathwater, which I thought was a funny name for a business, but when he told me their next event involved skiing with a bunch of other business owners, I was all in.

7 years and 20+ Baby Bathwater events later, my world looks a whole lot different. In that span, I’ve experienced more than one might in multiple lifetimes. I’ve sold two companies, started a third, and reinvented myself multiple times along the way. I’ve been heli-skiing, rafted the Salmon River on a stand-up paddle board, and danced until dawn on a private island (twice). Along the way, I even managed to meet my wife. Needless to say, it’s been a long, strange trip.

Defenders of Good Times

The lessons and personal growth are too many to list in a single newsletter, but here are the top takeaways from finding a tribe and going all in:

  1. We all crave human connection. Humans evolved in tribes, and we are hardwired to seek a place where we can feel safe. Because of the constant pressure inherent to entrepreneurship, finding a group where I can be myself and commiserate with folks who are also going through it is a total game changer. I can share my ups and downs, my failures, and my big dreams, and instead of being met with cynicism, they are met with optimism and encouragement. These people have my back without judgment, and sometimes, that’s all I need when times get tough.
  2. Someone else has solved your current problem. When I started my first company, I thought I had to figure everything out myself. While trial and error is certainly one way to do it, learning from others to shortcut the pain tends to be a much more efficient path. I’ve become a huge believer in R&D (Ripoff and Duplicate). No matter what I’m trying to solve, surrounding myself with fellow founders always yields a solution.
  3. Sometimes, the best way to accelerate is to step away. While taking time off and pushing meetings and deliverables can often be daunting, my biggest breakthroughs and perspective shifts always come when I create space. Oftentimes, leaving my cell phone and inbox on hold for a few days and connecting deeply with a crew of brilliant minds is exactly what I need to move forward. I always come back inspired and invigorated, even if I need to catch up on a little sleep from burning the midnight oil.
  4. When you show up with a give-first mentality, your business naturally grows. Networking is transactional. But when you show up to a group ready to share lessons learned, help others, and give freely, the butterfly effect compounds naturally. Every time I invest in giving with no expectations or strings attached, I receive that energy tenfold in return. If you remain top of mind by helping others, referrals flow naturally rather than via quid pro quo. The doors that have opened as a result have been nothing short of life-changing.
  5. The hive mind effect is real. Just by immersing myself for 3 days with driven, brilliant founders, I learn by osmosis. We all level each other up, and a rising tide really does lift all boats. With every new genuine conversation, there is an opportunity to change my mind and upgrade my belief system. The more I am able to do this, the more quickly I can become the best version of myself and, in turn, help inspire those around me. The power of compounding is amplified by the group setting, and we all reap the benefits.
  6. We could all use more play in our lives. While some groups focus on business, the beauty of Baby Bathwater is a play-first mentality. Good food, good times, adventures and live music are what set this group apart. When you connect via fun first, the relationships are based on a whole lot more than business, strengthening the quality. When I was falling in love with my wife, I actually didn’t even know what she did professionally until after the event because we were too busy talking about philosophy, art, and big ideas. The business piece is just a bonus.

If you are a founder looking to upgrade your life and your business, the fastest way to do so is to connect with others who are on the path. If it’s true that you are the average of the five people you surround yourself with, then imagine what happens when you surround yourself with several hundred other high performers.

While the benefit to my business has been massive, it’s dwarfed compared to the experiences I’ve accumulated over the years. The late-night conversations where I’m laughing until my abs are sore are the real gold.

Whether you are struggling with loneliness or simply want to upgrade the quality of your relationships, go find a group that resonates with you and go all in. You never know what lies on the other side.

Here’s to building your band of merry misfits,


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