How I Found Fulfillment in Angel Investing and Learned from Sig

I was dissatisfied with my current career. I was thirty-nine years old and had helped build and exit a startup, and was now a software and services executive. I was the president of a national professional services company that was a public company subsidiary. I had the title, salary, and perks. What I lacked was fulfillment. I was the proverbial dog that caught the car. “Now what?” I asked myself.

But I had responsibilities. I couldn’t just abandon my career. It was the economic engine that supported my family: the wife, the kids, the schools, the cars, the whole thing. My earnings paid for everything.

Then my boss stepped in over breakfast one morning. He said, “If you aren’t happy working here, you should leave.” I told him he was right to see it in me. I needed to man up and move on. And that is what I did.

I missed my previous life. I missed working with a real entrepreneur, building a business from scratch, and making daily decisions that spelled success or failure. I did the work knowing it mattered to my peers and customers, worrying about money, talking about our cash position in every management meeting, and figuring out how to get cash from customers as our primary focus. It’s called sales. I loved it, and I missed it. Now I needed to get back.

AudioFax and Sig Mosley

I networked with an entrepreneur named Mark Bloomfield, who had started a company called AudioFax. The principal investor was a new angel in the community. His name was Sig Mosley . I became their COO/President.

I stayed in that role for eight months. I did all I could to identify a market for this fantastic product. After a few misses, I determined I needed to be the right leader, or it was the wrong business model.

But I watched Sig. I learned from him as he tried to figure out this angel investing thing. And of all the people on the board of directors, I wanted to do what he was doing. But I wondered, “How do I even get started?”

I had accumulated my nest egg from selling our company back in 1981. But during the ten years since then, I was more focused on not losing my money than taking on the risk of growing it.

Claudine Clark, former branch manager

A former branch manager came to me with a business opportunity. She wanted us to start a professional services company together. She would be sales and recruiting, and I would be the president and financier. We did it. We started the company.

Six months passed, and there were three of us in overhead and two consultants on billing. My partner walked in and quit. I was sitting in a sublet space with no windows. I was down $150k. And I hadn’t had the income to support my family. I asked again, “Now what?”

Bob Lasher and Application Partners

Within the hour, I got a call from a friend. He was an accomplished salesman and sales manager. He wanted lunch, saying, “I am leaving where I work. You have a good network. I want to tap into it.”

We got together, and he told me, “I am leaving because of how the CEO runs the company. I don’t like the way he treats people. The way he treats me.”

“You feel this way because you now know who you are,” I responded. “You’ve lived long enough, made enough mistakes, and done enough things right to know who you are. You should start your own company. Stop working for people. Build a company in your image with your values.”

He said, “I don’t know how to start a company.”

I said, “Don’t worry. I’ll help you. And, by the way, I happen to have one.”

Then he said, “It takes money to build a company. Where would I get it?”

I said, “I’ll finance it.”

He refocused that company on analytics and built it to $7mm in revenue in three years. Then he started a SaaS company inside that company. We spun it out and sold it ten years later for $12mm.

And that was the beginning of my angel investing career. Since then, I have helped start five companies and invested in another thirty companies. Looking back, here are the steps of my journey and what I learned.

Knowing my why was just as important as my what.

My motivation for becoming an angel was just as important as being an angel.

I love entrepreneurs. I wanted to spend my working hours around them. They are amazing people. They are creators. They are dreamers. World-changers. Bold. Persistent. Hopeful.

I love being a part of creating from scratch—going from an idea to solving a problem to attracting a team. The whole startup process is invigorating to me.

I love making money and building wealth. This is a complex and risky way to do it. And the payoffs come every seven to twelve years, but I can’t think of a better way of living my professional life.

I needed to bring all my resources to this new occupation.

This is what makes being an angel so special. Just like the entrepreneur, I was willing to give this new business everything I got. I would contribute all my time, talent, and treasure. My years of experience in business, from startup to exit to earn-out to corporate. All the skills I developed. My network. My experience. I love it.

Preparing to become an angel investor could be a complex process.

It was for me. It started with needing to be fulfilled in my current career. To realize what I was doing wasn’t suitable for me. Despite my responsibilities as a husband and father, I needed to do something else.

This led me to AA. And then to God. I became a follower of Jesus.

This life transition, centered on recognizing there was a God and it wasn’t me, changed everything. God was now the authority in my life. He loved me and saved me. From now on, I was to live my life trusting and serving him.

This new belief system moved me from being an independent leader to a servant. I was finally ready to help entrepreneurs achieve their dream of starting and owning their companies. Being an angel wasn’t about me. It was about the entrepreneur.

Angel investing is a business.

Angel investing is a business just like any other business. It needs to have all the elements of a business. I had to identify a problem in the marketplace. I figured out who had the problem. I had to design a solution that solved the problem. I needed to make money doing this by developing a sustainable business model.

My market was professional services VPs who wanted to start a business. Their problem was they didn’t know how to get started. They didn’t have the money to do it. They didn’t have risk tolerance because of their family responsibilities. I solved these problems, and together we built businesses.

I became a disciplined investor.

In the beginning, this was easy. I knew what I was aiming to achieve. I knew what I needed to do to achieve it. And it worked most of the time.

As I made money, I began to lose my discipline. New opportunities in my market weren’t coming along fast enough. I started to invest more broadly. This led to losses, but more importantly, it diluted my brand in the marketplace. Finding deals over time became more difficult. I solved this by refocusing on software-enabled services companies.

I did well over the last thirty-plus years as an angel, but I sometimes wonder, “What might have been had I stuck to my knitting? If I continued to focus on starting professional services companies with experienced operators?”

And that’s how I became an angel. And that’s what I learned looking back.

I’ll leave you with this. If your why is strong enough, you can accomplish any what.