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...
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? 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...
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...
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...
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...
Pitch decks need to be compelling, in as few slides as possible. Pitch decks need to suck the reader into the story, only letting go after the ask. Thus pitch decks need to be storytelling, not essays about the startup. The trouble is, schools don’t teach story telling, they teach essays. The other trouble is, investors see thousands of pitch decks, creating an expectation for how those...
Most of the entrepreneurs I work with have yet to raise money from an Angel or investment fund (venture capital or debt or any formal institution). It is daunting to sit (face-to-face or online) across the table from an investor, as investors know more about the process of investing than entrepreneurs. Life on the investor side of the table isn’t as easy as entrepreneurs think. The...
It sounds like an oxymoron, but it is not uncommon for investors to interview entrepreneurs while at the same time those investors have no money to make investments. This is one reason some funds take months to make investments, as they themselves are fundraising while simultaneously screening and doing due diligence. The reality is that fundraising as time consuming and challenging for fund...
In November 2010, Nick Brown happened to find himself at a Manchester conference attending a talk by popular British psychologist Richard Wiseman, who had written a book called The Luck Factor. “Basically, the way to be lucky is to just put yourself in situations where good things can happen,” Brown remembers, “because more good things will happen to you than bad on any given day, but nothing...
