I have known Dan for a decade through the NYC tech ecosystem. I lovingly call him the curmudgeon of fintech – in this episode we go deep into how he is building a venture capital firm and practice, not just running a fund and how he views the world of fintech investing. Below is the …
Tags: Building The Machine Podcast, Dan Kimlering, Deciens Capital, Eric Friedman
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 the future. In the fast paced world of startups, leveling the …
Tags: Micro Wins, North Star Metrics, Onaroll.co
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 preoccupied with the companies potential energy, that I didn’t think to …
Tags: Liquidity, VC
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. Not to mention the person toll on the people. I bit …
Tags: Big Swings, Fire Phone, Fyre Fest
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. One of the most interesting results was the outpouring of support and questions we received around how we built the product, why we built the exercise, and how much …
Tags: coaching, Executive Coaching, No Code
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 special inside Microsoft and Bing. I recently caught up with Rob, …
Tags: microsoft, Rob Wilk
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. It lets me in on exactly how the relationships work, …
Tags: Co-Founder Relationships, Executive Coaching
“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. However to me this is a call for help that …
Tags: Andy Grove, Shiny Object Syndrome, SOS
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 do not know anyone that predicted the global pandemic of …
Tags: predictions 2021
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 to the todo list in front of the team. At some …
Tags: Launch