Hard Lessons Learned from a Gifted Entrepreneur

Karim Abouelnaga is one of the brightest and most inspiring entrepreneurs I have ever known. We met at the Atlanta-based Points of Light Civic Accelerator, CivicX, which is in the shadow of the Georgia Tech campus. After my presentation on angel investing, I talked with several of the accelerator’s participating entrepreneurs, including Karim. Karim’s company […]

What Type of Angel Investor Are You?

“There are three ways to do early-stage investing,” Nelson Chu insightfully said. I was meeting with three of the smartest investing minds I know: Nelson Chu, Graham Osborn, and Chris Dardaman. We were discussing Graham’s upcoming presentation to Angel Lounge at the ATDC. His topic was applying Peter Thiel’s Power Law of Venture Capital to […]

Is the Business Model Sustainable?

17 Sustainability Questions I Must Answer Before Investing

This is the third in a three-part series on how I make investing decisions for follow-on investments. The first article described how I evaluate the entrepreneur. The second article described how I think about market timing. This third article analyzes sustainability. Deciding on putting additional money in a startup is a more difficult decision than […]

Is the Now, Now?

13 Timing Questions I Must Answer Before Investing

This is the second in a three-part series on how I make investing decisions for follow-on investments. The first article described how I evaluate the entrepreneur. This second article describes how I think about market timing. The third article analyzes sustainability. When the entrepreneur is asking for more money, I want to remember the reason […]

Are They My Kind of Leader?

21 Leadership Questions I Must Answer Before Investing

This is the first in a three-part series on how I make investing decisions for follow-on investments. This first article describes how I evaluate the entrepreneur. The second article describes how I think about market timing. The third article analyzes sustainability. Recently, I was asked to do some follow-on investments. These are companies I invested […]

“Help! I’m Losing Money!”

How Abandoning My #1 Rule Cost Me

Angel investing at its best is a really risky business. But risky does not lose money. Bad risks do. I’m losing money because I left my number one rule, my key discipline. Be all in. Over the years, whenever I’ve been involved in a business after I’ve invested, I’ve only lost money one time. Give […]

Why Early Stage Involvement Is Critical for Success

What I Have Learned in 24 Years of Angel Investing

“What do you see as the responsibilities of a Chief Operating Officer?” he asked. “A COO’s mission is to execute on the company’s strategy,” I replied. This was a high-level question. I gave a high-level answer. We then slowly moved our discussion to some useful advice. The kind he could act on when he got […]

An Entrepreneur’s Success Depends on the Quality of Their Questions

What I Learned From My First Months as a Paid Coach

When I decided to get into coaching entrepreneurs, I had some high-minded ideas on how I wanted to help. I learned that what I think they need and what they need are two different things. I thought they needed holistic advice on business, family, and faith. After all, it is clear to me these three […]

How I Became an Angel Investor

And How I Learned the Hard Lesson That Typical Angel Investing Is Not for Me

In May of 1992, I left a startup on less than good terms. After leaving the corporate world, I was aching to get back into startups. I found one and jumped in as their chief operating officer and president. They had great intellectual property but couldn’t figure out how to monetize it. I had a […]

First Steps to Angel Investing

And the Thrill of Being All In

“I’m thinking this investing in startups is exciting,” said my good friend. Ted is a senior executive for an F100 company. As we were talking at a Christmas party, he told me he’ll be retiring next year at 58 years old. To me he looks 40. Great Leader, Great Angel I consider him a great […]