Weekly Walk

I Went on 100 Walks with 100 Leaders. Here’s What I Learned.

May 28, 2020

If you asked me in May of 2018 if I thought my (selfie) recorded walk down the Fort Point boardwalk with Manjit Singh would lead to anything more than a one-time post, I would have told you no.

Turns out I was wrong.

Two years, ~18 miles walked, 17 cities, two continents and 99 episodes later, the #WeeklyWalk is celebrating its centennial! And to help mark the occasion, I wanted to share the 10 biggest things I’ve learned from these walks:

  1. My arm gets really tired after five minutes of holding up my iPhone. I need to either work out more or keep the videos under five minutes.
  2. When it comes to selling—especially to CXOs—most vendors don’t do their research. They try to sell to them without understanding their organization, their pain points or whether they’re even the right person to even be selling to. Know your target!
  3. Informal is better. People love the seeing the human side of people: unscripted, unedited, what you see is what you get, no retakes.
  4. Audiences are far more interested in the fun questions than the business ones.
  5. Zoom fatigue is real.
  6. Wind is not your friend when it comes to video.
  7. It’s cliche, but true: Don’t be afraid to make mistakes.
  8. Data is king. And data strategy is its queen.
  9. Never say no to an opportunity. If you aren’t given an opportunity, raise your hand and make one for yourself.
  10. 10 bullet points are nowhere near enough to summarize everything I’ve learned from 99 guests and 500 minutes of conversation.

So who’s the lucky 100th guest? After being asked countless times why I’m never interviewed, I temporarily passed the torch to OpenView’s Devon McDonald. In true Weekly Walk fashion, we talked about the origin of the Weekly Walk, if I have a job outside of them, and my new quarantine hobby. Watch the 100th episode below—it includes a very special surprise Cameo from one of my favorite reality TV stars.


Cheers to the next 100 Weekly Walks 🍾

Lace up and watch more episodes

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.