Welcome to

For the first twenty years of my career, I (co)founded a series venture-scale software companies, growing each from an idea to a company earning millions in revenue, collectively serving tens of millions of customers.

I now use the knowledge gained from those twenty years to help new entrepreneurs.  My goal is to have them increase their odds of success by not repeating the common mistakes that I and my peers once made.  I do this in many ways:


The Next Step series of books guides entrepreneurs step-by-step through the process of getting from idea to operational startup, breaking the paradigm of startup investing, and explaining years of lessons teaching entrepreneurship.


The Next Step: podcast shares the lessons from the books plus other advice, anecdotes, and interviews, all in bite-sized audio pieces.


Fledge is a global network of conscious company accelerators, providing intense guidance, mentorship, investment, and support for a small set of entrepreneurs.

Africa Eats is the first spin-off of Fledge, taking a few dozen graduates, all run by native-Africans, all focused on building the food/ag supply chain across Africa to lessen hunger and poverty, wrapped as an investment holding company to provide capital, guidance, and support beyond what is typically done within a business accelerator.


Answering questions from entrepreneurs on Quora.

Plus in these various efforts, I do my best to uncover hidden assumptions, break investment paradigms, and seek solutions to income/wealth inequality.

And despite writing checks to entrepreneurs, I still consider myself first and foremost an entrepreneur, and as such every so often I simply have to create something new, such as:

The philanthropic investing service at Realize Impact, a 501c3 public charity that I co-founded, which lets any philanthropist turn a donation into an impact investment.

I hope something from this long list is of help to you.

Latest blog posts

1979: Will WORD PROCESSORS start a HOME WORKING revolution?

From 1979… how different will be it be in the office of tomorrow…

… a “text editor” and electronic memos… which will lead to the office workers working from home. A reasonably good prediction of the future… but off by a few decades.

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

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...

The Apple //, ///, /V, V, … LXV that could have been

I fell down an 8-bit rabbit hole 45 days ago, looking back at how the computer industry evolved from the Apple ][ in 1997 into the 1980s, up to the first pen computers of 1991. Last week I found the needle hiding in this haystack (mixing metaphors) on why evolution took that path, and now it’s time to put together all the learnings into an alternative history of what might have been, given...


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Recent blog posts