‘Why Not You?’ and Dan Primack’s Peloton Ride

As I told my HBS students, it took me a while to figure out what I wanted to do for my career. And, it was a process to take on risk. Over time, however, I’ve subscribed to the view of “Why not you?” (taken from the 2004 Red Sox). More below.

I had an extremely traditional start to my business career: investment banking, management consulting, and private equity. Then, I became an accidental VC (who then started a new firm), whereby most of your investments fail and, if you’re lucky, a handful of your investments go public or are purchased for big sums.

It takes time to save some money to have a cushion if you’re not from a family with money. And, it takes time to get used to dealing with risk and potential failure.

When I was growing up, I didn’t have any entrepreneurial role models. All of the Asians on TV or in the movies fell into a few buckets: martial arts experts, nerds, scientists, doctors, or evil villains. There was no Tony Hsieh (Zappos), Alfred Lin (Zappos, Sequoia), Jack Ma (Alibaba), Rob Go (NextView), or Tony Xu (Doordash).

Over time, all that mattered less. I felt drawn to roles that gave me autonomy, and I slowly started to change career paths. And, that let me to VC, which back then was still a small industry comprised of small firms.

Fast forward, and taking risk then bled over into my friendships, too. Helping to start companies led me to realize that helping to start communities also was fun.

Today, my social life revolves around initiatives I help coordinate or helped start:

  • A parish-based men’s group. Six of us connect at least every week to discuss a reading or relevant topic, and we’ve been doing this for over 10 years. When the pandemic ends, we’ll again resume weekend get-togethers at restaurants or couples’ dinners at each other’s houses. It’s a good time.
  • A Zoom comprised of college friends. Each month, a person schedules the event, picks a discussion topic, and moderates the Zoom. I find a discussion is much better than a general Zoom cocktail hour with no agenda.
  • A fly-fishing blog. We writers all have day jobs, write posts for fun, and give away 100% of our ad-revenue profits. Before Covid, we periodically met up for long-weekend trips or day-long fishing outings. A great group of anglers who also happen to be great people.
  • B-school reunions. A combination of three of us have co-chaired all of our class reunions, and we’ve become a very tight trio. We text nearly every day.

To be honest, I didn’t have a grand strategy for this part of my life. I didn’t write business plans or pre-conceive programs. Instead, if there was a need, I decided to take the next step.

I think an example of this is what journalist Dan Primack has done with his Peloton Community rides. He uses his social media presence to rally riders and donors, and his morning ride today has raised nearly $200,000 to help restaurant workers. (It was a fun ride!)

So, as I asked my students on the last day of class: “Why not you?”

In life, you will run across potential business opportunities. Or, you’ll notice gaps in your social life or in your community. Rather than wait for someone else to take the initiative, you should consider being the person who kicks things off.

Why not you?

Leave a Reply