Function over Fashion - Building the Right Team with the Right Roles

I might be a different type of investor, but I’m also a different kind of traveler. 

As my wife will attest, I get picky around hotels – and not for the normal reasons. I could care less if the room looks trendy, or cool. I have almost no interest in how the lobby looks, or if the hotel restaurant serves great food. I normally love the gym, but am usually too tired to use the ones at hotels. And, I prefer self-parking over valet parking, even if it means walking a few blocks out of the way. 

I’m usually looking for a hotel in a good location, with a really good HVAC system, comfortable bed, doors that don’t slam, and good blackout curtains. Most of this might seem either basic, or specific. However, all of them translate into a good sleep environment. If I’m traveling, I’m not usually hanging out in the room all day - I can do that at home. I’m also not going to derive a real benefit from a cool headboard, or giant glass enclosed shower. The only thing that really matters is saving time (from a good location), and having the best chance of sleeping well. 

Travel is more challenging post-pandemic - airports are overloaded, rental car companies have horrible technology, and hotels seem very disorganized. Many of the newer hotels also lack basic functionality (for me at least). The blackout shades (not curtains) don’t cover the windows, rooms don’t get cold in the summer, and the doors usually slam. So, between being hot, or woken up by light or noise, they don’t provide basic functionality. The funny thing is that most HVAC systems can properly cool the room, but temperature limits make it challenging. 70 degrees rarely feels like 70 actual degrees in a hotel room - and I prefer to be even colder. Most blackout shades probably cost about as much as curtains, and door dampeners are not very expensive. And, the bane of my existence are HVAC systems that loudly click on and off all night - it’s a completely unnecessary noise (that is impossible to block with anything I’ve tried). 

I might seem obsessed with sleep hygiene, and that’s true. But, I also tend to travel in a pretty intense manner – I want to get in, do everything, and get out. I’m not sitting around much, and I don’t build in a lot of down time. There is some flexibility built in, especially given the tendency for travel problems/delays, but I generally know what I’m doing and where I’m going. 

On one trip, I drove around most of Florida in 3 days. On another trip, I was in Boulder, Vail, Golden, and all over Denver in 3 days. While I could have taken my time, and spaced out meetings, I’d rather get everything done efficiently. And, I also leave time to actually have real meetings - I’m not usually staring at my watch wondering if I can make the next one. 

These types of trips might seem like a nightmare to many people, and a way to kill the fun of traveling, but I can still have some fun. In Florida, I walked around Clearwater Beach, most of the University of Florida, and Ormond Beach with a portco founder. In Colorado, I caught a Rockies game with a friend, drove through a hail storm from Vail (fun for me), and walked around the University of Colorado. Either way, I’m pretty sure people think I’m a little nuts, and need to relax more. 

This might seem like a weird article, but there is a point. 

Every founder has a different style - and builds their companies in different ways. They also have a supporting cast that helps them, and their companies do their best. Some of this support is very functional, and some of it is just window dressing. However, resources are limited, and founders try to give themselves the best possible odds of success. Resumes and interviews help find the right skills and culture fits. Hiring for the right roles helps put those hires in the right place to push the company forward. 

In 2020-2021, many founders hired for functionality, and fashion. Sales teams exploded, new roles were created without a tangible impact, and product teams iterated on mostly meaningless changes. Money was burned as fast as possible, and ultimately, many companies ended up in increasingly precarious positions. The best founders did spend some money, but on impactful hires in the right roles – and continued to operate with a function first mindset. Sales hires are notoriously hard to get right, but building the right culture with the right leader (and right marketing collateral) mitigates issues. Developers cost their weight in gold in 2020-2021, but there are also amazing developers overseas (and products don’t need to be overengineered with unnecessary features). 

One of my best hotel stays in 2023 was at one of the simplest hotels - an Embassy Suites in Phoenix. It was a big, but fairly basic room – there was not even real A/C in the bathroom. However, the A/C worked well in the bedroom, the bed was comfortable, curtains did their job, and doors did not slam. The front desk guys were also very knowledgeable about the hotel, and really cared about their jobs (both of those elements are challenging these days at hotels). As a result, they gave me a room that checked the right boxes (away from the elevators, and in the corner). No part of the hotel or room was Instagramable or fancy, but it had the perfect amount of function. 

The best founders are more like the Embassy Suites than the Pendry (San Diego) or Gwen (Chicago). The Pendry had a cool shower, fancy bathroom, and amazing pillows – but it also had a bad HVAC system and curtains that let in a ton of light. The Gwen had crazy wallpaper, a fancy bathroom, and an HVAC system that clicked all night (and didn’t work well). Although I got a Bonvoy discount at the Gwen and AARP discount at the Pendry, both were much more expensive than the Embassy Suites. And at the end of the (long travel) day, function is all that matters.