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Micro-wins-as-a-Service & North Star Metrics (Onaroll.co)

I am a big fan of celebrating your wins. I often highlight "micro wins" with executive coaching clients as moments worth celebrating. I also love figuring out where a founder is going and what their north star metric could be, both now and in...

A.T.S.L. (Always Take Some Liquidity)

water drop
I learned a valuable and expensive lesson about taking liquidity when the offer arises, or rather NOT doing so in my case. Earlier in my career I had the chance to sell some stock and take some liquidity and I passed. I was so...

More Fire Phones, Less Fyre Fests

Jeff Bezos notoriously launched the Fire Phone around 2014 to much attention - I think most agree that it was a spectacular failure. But was it really? This project was a $170M write-off for the company. There was the hardware, software, and marketing costs....

Tapestry.so – No code project breakdown of time, costs, and a guide for others

My partner (Steve Schlafman) and I recently launched Tapestry, an exercise for founders to invest in their relationships, and it was met with an incredible reaction. https://twitter.com/schlaf/status/1356993994568437761 One of the most interesting results was the outpouring of support and questions we received around how we...

What does this make possible?

I have been a fan of Rob Wilk since we first worked together years ago. I even wrote an incredible idea he shared with me back then called the "no update update" which I use all the time. Today Rob is building something very...

Tapestry – Weaving Stronger Co-Founder Partnerships

I strongly believe that one of the most important questions you can ask in a well-functioning, growing organization is: “How are you investing in your team's communication and relationships?”  It has also become a great question as an early stage investor and an executive coach....

SOS Shiny Object Syndrome

person catching sprinkles
“Everyone is always chasing after the next shiny object” -Founders This is a line I hear often from founders about their teams or themselves in early stage companies. While partly to blame, CEOs have gotten to where they are by trying, testing, iterating, and experimenting....

2021 Predictions

hands with latex gloves holding a globe with a face mask
Did anyone have global pandemic on their bingo board? Ok lets move on... Last year I decided to do my first ever public predictions for 2020 and the decade ahead. What a fun exercise and wow was I wrong! As mentioned at the top I...

What needs to be true?

wood summer industry technology
I reconnected with a CEO recently that launched their business about three years ago. We chatted about the long, harrowing lead-up to their first product launch. The list of things to do was long, the road ahead was unclear, and there was no end...

Don’t be afraid of a “No”

I was talking to a good friend recently who lost his job during the pandemic crisis happening in the US, and with a mortgage and a new baby was remotely looking for new work. While a challenging time for many, searching for a new...