Extravagance as Savviness

Look like a million bucks.

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Around 5 minutes to read

During my first year of running SuperFriendly, I was doing mostly “lone freelancer” work—straightforward design projects where I received a brief and I’d knock out comps at my desk. Slowly but surely, though, I was getting inquiries for larger projects that needed slightly larger teams to work on them, something I was more excited for and experienced at.

One day, I got an inquiry from a CEO who wanted a team to jam on some new ideas for his company. (Bonus: it was a company whose products I used regularly, so I was extra keen to help them with this work.) He offered to fly my team and me to his city for a few days to see how well we worked together, and we could all decide if it was something we wanted to continue. This seemed like a reasonable proposal, but the way he asked was pretty unique:

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Would you be up for a first class flight to [city] for a meeting on Tuesday or Wednesday of next week? We would put you up at the [swanky local hotel]. We could meet for lunch or in the early afternoon on either day if that can work for you.

I had traveled for clients before, but it usually involved booking the cheapest flights and lodging possible because of the combination of wanting to shell out the least dough and because reimbursement policies usually had a pretty low cap approved expenses. This was different! Flying first class? I don’t think I had ever flown first class before. And staying at one of the best hotels in the city? The opulence!

It didn’t stop there. Once we arrived, we realized that the CEO had booked the Penthouse suite for us. There was even a grand piano in the living room!

I was feeling two things simultaneously:

  1. We had arrived! This was peak agency life, where clients would spare no expense to work with us. We were in demand! This was the good life.
  2. How dare he! Was he just throwing is money around to show us how well the company was doing? Was this some sort of intimidation tactic to somehow give him the upper hand, to make us prove we were good enough to hang? Fine, we’ll bring our A-game and make him wish he bought the whole dang airline for us.

When it came time for our meeting—which was arranged in the living room of our suite—the CEO showed up a few minutes early, modestly dressed. This was not the guy I envisioned who had dropped all this cash. He was smart, a bit understated, and made great conversation that wasn’t about, I don’t know, buying yachts or whatever rich people talk about. Not what I expected, but we went on with the meeting and working session, which went great! Later in the day, we thanked him for the great working session and the more-than-generous accommodations.

Brazenly, I asked if he did this for all his partners.

“Oh, absolutely,” he replied. “It’s the most economical way to do this.”

That was not the response I expected, and “economical” was not the word I would have used to describe our experience. I probed more, and he explained. Apparently, booking the Penthouse suite was actually cheaper than booking multiple separate rooms and a conference room for the day. Plus, conference rooms are public spaces and often have cameras and such in the hallways and nearby. Doing the meeting in the Penthouse living room gave us some additional privacy to talk about some confidential company plans without worrying about anyone else overhearing.

Huh. Color me surprised.

“What about the first class flight?” I asked.

He admitted to it being a bit extravagant, but it also saved a little bit of money and time for us to have had a good meal before we showed up as opposed to having to go out to a fancy restaurant. Also, he found that he got better work from people when they had a comfortable flight, as opposed to when they’ve had an uncomfortable and labored travel experience and then had to be on their A-game for hours in a working session.

Instantly, what I initially saw as extravagance now looked much more accurately like savviness.

This was a formative experience for me as an agency owner. From then on, for any travel I’d book for my teams, I’d look to make it the most comfortable and easy-going as I could afford. This included every seat and room upgrade available and often meant taking the team to a tasting menu or Michelin-starred dinner the night before a full day or few of intense workshopping. I wasn’t necessarily trying to save money, but the return on investment in creating comfort for the team was almost always palpable in terms of innovation and morale.

Last year when I shut down SuperFriendly, my wife and I started to prepare for a season where money might be tight as I was making a career transition, so we started looking for all the places where we could cut our expenses back. At the time, we were both driving our dream cars—and we were paying for it, literally.

A few years back, we had invested in solar panels for our house to decrease our reliance on the grid, and one of the perks was that our installer threw in a free electric vehicle charger in our garage for if we ever got an electric car, something we figured might be in our near future. So, we sold our dream cars and bought two used Teslas from a local car dealership, cutting our car payments to a fraction of what we had been paying. Conveniently, the timing of this choice also coincided with the highest gas price surge in a long while—something that hasn’t really come down too much since—so moving to two electric vehicles meant a bonus of also saving hundreds of dollars a month by not having to buy gas.

Of course, when anybody asks or visits our house and sees two Teslas in our garage, they assume we splurged. Yet another case of supposed extravagance that’s actually savviness.

How have you been savvy in a way that might look extravagant to others? Drop me a line and let me know.

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