Rich & Sad

Wil Reynolds
4 min readMay 16, 2022


“NO such thing as a life that is better than yours, no such thing, no such thing.”
— J. Cole.

One of the most profound statements in my 23 year professional career came from a client who sold to Alibaba — in a pretty big deal, all over crunchbase etc etc. Millions — he was the founder / CEO so I was at the highest levels of the biz.

Me: “Congrats man, what a ride!”
Him: “Wil, sometimes it is better to own a lot of something small then to own a little of something big, I gotta run.”

That hit me, hard. This man just sold for “likely low 9 figures” and had a significant ownership stake — this was the FIRST thing he thought to say to me days after? Damn.

I shared that with Alex Hillman recently to which he replied,
there’s a lot of people out there Rich and Sad.

Got me thinking even harder. There’s a lot of Rich & Sad out there behind the facade. Alex went on to say, “Anytime someone sells their business, my first question is “are you OK, not congratulations.”

Happy on social, sad in real life

I was listening to a podcast about “van life” today and how much it sucked for someone who tried it, wait what, it sucked? But the awesome photos, the dropping the 9–5, the waking up every day to do what you want, how could that not be dope? Look. At. This. Life.

My morning, was boooooring.

The author talked about how it looks on vanlife tiktok and she described how that was what she expected, but the reality was a lot of skuzzy bathrooms, flat tires, really bad sleep, feeling like she couldn’t breathe in humid days(bad AC), rainy days, lack of showering, etc, etc.

This broadly gets me thinking of one J. Cole song I love, called Love Yourz — watch the lyrics video, but this line gets repeated a lot.

Start vs Finish (Getting married vs staying married)

Something else constantly on my mind is the start vs the finish.

When is the last time you were at a huge celebration of family members, likely a wedding right? 2 people committing to a life together starting today, lets send them off and throw a huge party, right?

Did you throw a big party on their 5th year of STAYING together, shocking how much effort and money we spend to send people off day 1, but on day 3,000 of being together, you send some happy anniversary cards. I wanna live in a world where we praise staying together cause staying together is hard.

Start vs Finish (Business edition)

I have a few companies whom I track, they are often written up in the press for raising money or moving into their new offices for expansion. The CEO’s typically are quoted with what they expect to happen over a few years.

Once a year I get the emails come back into my inbox, just to see where are they now, and how many of their interview stats played out?

There’s a lot of people out there saying “we’re going to triple in 3 years” who grow 50% in 3 years — which to me is still worth celebrating, but it does make me reflect how we entrepreneurs say a lot of stuff that never happens (Hey Elon, still waiting for my car to drive itself).

Are we putting out the highlights like “we’re going to grow revenue by 500% in 5 years” but no one holds us accountable to “did you actually do that?”. Where are the year 1, 2, 3 check in stories that start off like “Last year you said you were going to double headcount in 5 years, are you on pace?”

Contentment — Try it on for size

The world is telling us to do something different, start something new, get bigger, buy stuff, sell stuff — try to keep doing the same thing in those moments and try to find a new joy in the same old.

Every day I wake up, lace my shoes up, and I am reminded that there’s no such thing as a life that is better than mine, so I don’t seek one, I’ve felt this way pretty much every day for the last 20 years — and I’ve only had 1 day in 20 years I didn’t want to come to work, but that story is for another time.



Wil Reynolds

Serial Underdog @seerinteractive doing SEO, Marketing, & Stuff, I am whatever you say I am.