3 Prerequisites to Becoming a Successful Entrepreneur

“I have to ask you a serious question,” Bob said. “Go ahead,” I replied, having no idea what he was about to ask. “How do these entrepreneurs pay their living expenses?” Bob is a professional services vendor who is new to the entrepreneur community. He sees a lot of money and attention being focused on […]

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 […]

Founding Entrepreneur’s Key to Priority Setting

“There is just too much to do,” said Mike, Jim, Tyce, Greg, Robert, Kristin, and all the other entrepreneurs I am involved with. I hear this all the time. They will come to me with a problem. It all starts with fundraising. After fundraising, it is all about growth. This quickly gets to strategy and […]

How to Know Your Startup Idea Is Lousy

Sometimes Your Experience Does Not Matter

“We quit our jobs and started this company, and we would like your help,” said the entrepreneur and his partner. They are not recent college graduates. They are both smart, well educated, and about 40 years of age. They are married with kids, which includes houses, cars, and future education expenses. They left high paying […]

4 Questions That Reveal What’s Important To You

What kind of entrepreneur are you?

“The first thing I do with someone who asks me to mentor them is ask four questions,” said Alan Urech, one of the most dedicated and experienced mentors in the Atlanta startup community. Learning from Alan I was just leaving the Grace@Work Bible Study that met in the Atlanta Tech Village Speakeasy room off the […]

Why Communicating with Your Investors Is Essential

I haven’t heard a peep since we closed, I thought. There is always a flurry of activity associated with fundraising. The entrepreneur starts the process by putting together a presentation which shows just how amazing the investment opportunity might be for the investor. Dissolving Abandonment Fears The investors who are interested are then filled with […]