Now that we’re all used to Zoom, the question arises as to the courtesy of how to talk on a media which has an inherent lag time. The most common expectation is that you wait for the other person to finish speaking, then wait for the lag, then take your turn. But I was raised in a part of the world where those expectations were not the norm for in-person conversations, and that half second...

Ruthlessly Resourceful and Pathologically Persistent

pretty pattern

Years ago I came across a great explanation of what makes a great entrepreneur. It is someone who is “ruthlessly resourceful”, ignoring the resources at hand but still able to realize their vision. Another trait common to successful entrepreneurs is “pathological persistence”. Not taking “no” for an answer is a consequence of that behavior. Iteration upon...

Rules, Razors, and other Aphorisms of Advice


The follow thread popped up on my Twitter feed from Sahil Bloom… my favorites are copied below… A “razor” is a rule of thumb that simplifies decision making.The most powerful razors I’ve found:— Sahil Bloom (@SahilBloom) July 17, 2022 Luck: When choosing between two paths, choose the path that has a larger luck surface area. Your actions put you in a position where luck is more...

Writing can be music

Writing as music

I saw this on Twitter… and wonder why none of my English teachers were ever this eloquent? This sentence has five words. Here are five more words.Five-word sentences are fine. But several together becomemonotonous. Listen to what is happening. The writing isgetting boring. The sound of it drones. It’s like a stuck record.The ear demands some variety. Now listen. I vary the sentence...

Imperfect information is more fun

Chess pieces

I had an epiphany yesterday related to chess and entrepreneurship. I figured out why chess makes me so frustrated and why when I picked up chess in the pandemic, my chess rating hit a plateau above average, but no where as high as I expected. The problem is that chess is a game of perfect information. The challenge isn’t in predicting the next few moves. The challenge is in finding the best...

10 years… 20,000+ contacts/connections


This year I’ve hit a lot of milestones. 10 years since the founding of Fledge. The 10th anniversary (update) to The Next Step. 30 years as an entrepreneur. And this week… 20,000 connections in my spreadsheet of contacts, a.k.a. my CRM. I started this list back in early 2012 when I left “tech”, jumped into the world of mission-driven for-profits, i.e. impact companies and...

Where is your horizon?

harbor with sailboats

Where is your horizon? How far away from home does your daily life take you? How far into the past and future do you think about? I live on an island, and know quite a few people whose daily lives never even reach the beach. On the other end of the spectrum (to mix metaphors), few days go by when I’m not talking on Zoom to someone from Africa, if not also calls in the morning from Europe...

The 10th Edition of The Next Step

The Next Step 10th Anniversary (header)

Ten years ago I published my first book, The Next Step. This was inspired by a few life changes, including being asked to teach entrepreneurship to MBA candidates at Bainbridge Graduate Institute, working as an Entrepreneur in Residence at the University of Washington, and the imminent launch of Fledge, which at the time was one small business accelerator. This first book covered the process from...

Reminiscing of 30 year old (failed) technology

Remembering he Apple Newton

I’m not the only one this week looking back 30 years at failed tech gadgets. Today in my news feed was a post on ars technia, Remembering Apple’s Newton, 30 years on. Thirty years ago, on May 29, 1992, Apple announced its most groundbreaking and revolutionary product yet, the Newton MessagePad. It was released to great fanfare a year later, but as a product, it could only be described as a...

Seeing is hard, especially into the future

Cover of BYTE 1991

This year I’m celebrating 30 years as an entrepreneur, and with that round number reminiscing more than usual about three decades of learnings. My personal journey into startups began a year earlier, in February of 1991, while still a senior in college at Carnegie Mellon. That month’s issue of BYTE magazine focused on the future of laptops, with a series of articles talking not just...


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