CategoryAdvice

Building a successful business is a series of lessons. Many fail. Enough succeed. What I’ve learned from doing this process for three decades is that the quicker you learn the lessons, the easier the path to success. And by lessons, I don’t mean the big lessons that the world throws at entrepreneurs, but the little lessons that you set out to learn yourself, as you hypothesize on how...

I thought it would be enough to write a book about the startup pitch. I was wrong. I thought maybe that was too many rules, too many details, simplify it down to a slide-by-slide guide. Far more often than not, wrong again. What is missing from the vast majority of the pitches shared with me is the story. Pitches are supposed to tell a story. A nice, simple, logical story of a business. What...

It is incredibly useful in business decisions to have a financial model, and a critical (but often overlooked) step for startup fundraising. That said, over the last decade I’ve worked with thousands of entrepreneurs whose favorite Office tool isn’t Excel, who don’t know how to analyze someone else’s financials let alone create a financial model from scratch. It...

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...

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...

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...

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...

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...