Creating Angels

Out of the 320 million Americans, fewer than 320,000 are Angel investors, investing in startups. Quick math, that is less than 0.1% of all Americans. The ratio only gets worse elsewhere in the world. Why? Investing in startups is complicated. Historically, it’s a skill learned in an ad hoc apprenticeship, with new Angels observing more experienced Angels for months or years. Few people have...

Three types of companies and three types of mission-driven companies

I categorize companies into three categories: A- Companies focused solely on profits, running extractive businesses, unconscious to the needs of their employees, their communities, and the world as a whole. Most of the S&P 500 and Global 1,000 are in this group. B- Companies that truly care about ESG: Environment, Social, and Governance. In short, companies whose management works on improving...

The Drought of Capital

Entrepreneurs are farmers of ideas.Farmers who are living in a perpetual drought.No matter how well we teach entrepreneurship, the drought creates year after year of failed crops. The fix has little to do with more and better incubators, accelerators, and startups labs. This drought is the lack of capital to support the existing startups. Just as we can’t solve a regional drought by...

Sharing Equity with Employees

There are a few aspects of venture capital whose origins are lost to history. One of these is the 20% stock option pool. Or more simply, the idea that everyone in the startup should own (at least a small amount of) the equity. Does this idea date all the way back to Rock and Davis, or did it come later? Why 20%? Why not 10% or 33% or 50%? Was this idea ever debated, or did one VC decades ago tout...

Yellow Flags, Yes vs. No

A few times per year I attend conferences full of fellow fund managers, managers of family offices, and big impact investors. The rest of the year I share investment opportunities multiple times per week with other investors. From all these conversations, I’ve come to realize the power and benefits of running a business accelerator rather than a traditional venture capital fund. From 10,000...

Too Big to Succeed

Blogging is just one more example of the key lesson I teach entrepreneurs, that it takes multiple iterations to find something that works. That is true not only for products, but also for sales, marketing, and messaging. The words I’ve failed to find in the story of WeWork and its lead investor Softbank I found buried in a CNBC article: Too big to succeed The problem with Softbank’s Vision Fund...

The Tokyo-Riyhad Capital Bubble Bursts

When the WeWork IPO was still a possibility, the Tokyo-Ridyhad Capitalism paradigm seemed outrageous but not impossible. Two weeks later, the bubble has burst but the unwinding seems to be just as outrageous. According to TechCrunch, for all the harm and fraud Adam has caused his employees, landlords, and investors, SoftBank is rewarding him with $1 billion buy out plus a $500 million loan to pay...

Investor Connect (podcast)

I’m on the other side of the microphone on the Impact Connect podcast, being interviewed about my unusual style of startup investing.

In this episode, you’ll get my unique perspective on questioning everything. Originally posted on

The Softbank Vision Fund vs. Reality

The venture capitalists following the traditional model of California Capitalism have a thesis that there are billion dollar business opportunities, there are business models able to capture those opportunities, and teams which can create those businesses if sufficiently funded. Softbank’s Vision Fund takes that model to a new level. A Tokyo-Riyadh Capitalism model. But a model that seems...


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