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...

A quick explainer on Impact Investing

What is impact investing?  It’s a question that gets asked a lot, even in the crowd that calls itself impact investors.  I explained the general idea on-stage at The Nature-Accelerator in just three and a half minutes:

Revenue – Expenses = Profit

At a recent Seattle Impact Investing Group meeting, Leslie Christian was a guest speaker, sharing some of her wisdom on mixing impact with investing.  Her wisdom is wide and deep, but one idea especially popped out: the paradigm of shareholder value, especially in regard to investors, risk, and return. Specifically, what we’re taught in Finance is the following equation: Revenues...

Somebody’s Gotta Get Rich [SSIR]

Kevin Starr of the Mulago Foundation wrote a nice explanation of the need for and sweet spot of impact investing, Somebody’s Gotta Get Rich. Impact at problem-solving levels of scale doesn’t come from one-off businesses. “Levels of scale” as in making a noticeable difference in the world, rather than simply telling a good story imagining a world different from how it is today. Kevin...

The future you want, rather than the future that might otherwise be

One of the challenges of being an “impact investor” is explaining to others what you mean by “impact” as the definition varies from person to person.  The best explanation I’ve ever heard came from Ted Levinson of Beneficial Returns on a panel at a recent SOCAP 365 event in San Francisco (which I heard on the “Unusual Investments” episode of the new Money...

Don’t go chasing unicorns [Guest post]

Venture capital should never have become the standard way for us to fund new businesses. As an asset class, it’s uniquely designed to fund disruptive innovations. It does this by funding ventures that are likely to fail, but — if successful — can result in outsized outcomes. In other words, it’s a ‘home run’ based model. For a venture capitalist, seeing 6 or 7 out of 10 portfolio companies fail...

The 99 Investor Problem’s Solution

Thanks to the Angel Capital Association the so-called “99 investor problem” is sufficiently solved for small seed funds.  Specifically, S.2155 was passed by Congress and signed into law, which amongst a series of changes to financial regulations included: (Sec. 504) The bill amends the Investment Company Act of 1940 to exempt from the definition of an “investment company,”...


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