What Sig Taught Me About Angel Investing
I watched him and learned. He dedicated the first part of his life to helping a company. The next part of this life was helping entrepreneurs. The last part of his life is helping those who help entrepreneurs.
Sig Mosley invited me to attend the annual Siggie Awards. But this invite was different. There was an insistency about the invite. I felt he was saying, “You need to be at the Siggie Awards,” not, “I would appreciate it if you would attend this year.”
So I knew from the beginning something was up. It was more than trying to re-establish the in-person kick-off post Covid seclusion. Earlier in the week of the Siggie Awards, I got a call from Sig. He asked, “You are coming, right?”
That’s when I thought, “I might be a recipient.”
I got there on time. Sitting in my car in the parking lot, I thought about what I might say if I were honored as a recipient of a Siggie. This award aims to recognize angel investors in the Atlanta technology community who have demonstrated the heart to help entrepreneurs succeed. People who care and make a difference in our startup community by investing their time, advice, network, and money. These are my words as I understand the Siggie, having attended the very first event several years ago.
I asked myself, “What did I learn from Sig over the last thirty years?”
I met Sig in the early fall of 1992. He was investing John Imlay’s money back then under the banner of Imlay Investments. As a Georgia Tech grad and a high-profile, successful software tech executive, John started this fund to give back to the community after his exit from MSA. He wanted Sig to find the “tigers” in the tech community with great ideas to turn into great businesses.
He chose Sig to lead this effort because he trusted Sig. Sig was John’s CFO for the prior twenty years and then managed the family business and foundation.
Sig’s first investment was AudioFax. He was the only real outside money in the deal. The rest was friends and family. The founder, Mark Bloomfield, and his CFO, Charles Brewer, wanted to hire me as their president. Sig and other board members interviewed me, and I got the job.
I knew nothing about angel investing back then. What I learned, I learned from Sig. As the operator in the business, I watched him navigate the challenges of the business. These included the entrepreneur's demands, the management team's coordination, the proper formation of the board, deal structure, family money, emergency follow-on rounds, and coaching. I learned a ton.
Then I quit. I was not the right executive to lead the business forward. Sig was so gracious when I went to tell him what I had decided.
I didn’t know I was about to step into one of the most challenging periods of my life. It was a transition time. A time of massive change. I went from a career as a tech executive to a career as an angel investor. It was painful and included lots of personal change and growth. But on the other end, I was better prepared to be an angel investor.
As a new angel investor, I ensured I was in Sig’s orbit. I wanted to learn from him. He had a unique set of skills that I didn’t have. Skills I needed to develop if I were to have a chance at being successful.
Back to the Siggie Awards
I’m sitting in the audience as they are preparing to kick off this year’s Siggie awards. Before the presentations, the AV person looks through the PowerPoint to make sure the presentations are in the right sequence. I don’t think he knew they were displayed on the main screen.
I see a few names and pictures of recipients come up. And then I see my picture flash by. Under it was written “Lifetime Achievement Award.”
Now it was confirmed. I was getting a Siggie. I was in the slide deck! I kind of panicked. “What am I going to say?” I thought. “My friend and mentor is honoring me with his award. He is an angel icon in our community.” These thoughts went through my mind as quickly as the slide flashed by in the AV review.
My answer to the question was simple. Tell everyone how you met Sig and what you learned from him. Honor Sig.
Here is what I learned from the most famous angel investor of the past twenty years in the Atlanta tech community, my community.
Love the entrepreneur.
Sig was focused on the entrepreneur. He gave all he had to make them successful. He was always available any time, day or night. He coached them, comforted them, and disciplined them. He told them the truth. But the entrepreneur always knew Sig was right there as they worked hard to achieve their dream. In short, he loved them.
This is the heart of a successful angel investor. He is driven by love. To help. To sacrifice for others.
Give all you got to help them succeed.
Sig invested John Imlay’s money. More importantly, Sig invested himself.
This is the hard part. So many of us angels are purely passive. We’ll invest our money, but we won’t personally invest. Maybe we’ll help if you ask us if we feel so led.
This is not Sig. He was all in on all his investments. At one point in his angel career, I asked him, “How many boards do you serve on?”
He answered, “Thirty-two boards.”
“Are you nuts?”
Sig was married with three kids, one in elementary school and two in middle school, and he had two adult daughters in another state from another marriage. And he was running the Imlay family office and foundation.
But his first priority was always the entrepreneur. He would do what he could, anything he could, to make the entrepreneur successful. This dedication to these men and women sets Sig apart from every other angel investor I have ever met.
Serve the greater community.
Part of John’s life-long personal mission was to give back to his community. He worked tirelessly while the CEO of MSA, a high-profile alum of Georgia Tech, and the money behind Imlay Investments to raise the economic tide in our community. He knew that if he could use his influence, time, and money to help others (tigers, he called them), all of us in the community would benefit.
Sig worked for John. He represented John. He was on John’s mission. He succeeded in that mission.
I interviewed Sig at Angel Lounge at Georgia Tech in November of 2022. The room overflowed to pay tribute to all he’s done for each of us. He personally touched all of us in the community and many in the room. And he told the stories of how he and John got started. He gave us an inside look into his most successful deals and how close to the edge they ran from time to time. And he spoke of the entrepreneurs. Who they were and how he loved them.
After the event, he and I finally got to pick up some food from the buffet. We sat down in the room, just the two of us. As we started our meal, a young lady neither of us had ever met interrupted us. She was a former investment banker who wanted to help entrepreneurs in the selling process. She asked Sig, “Would you meet with me?”
“I would love to,” he said. “Here’s my cell number.”
I asked him, “Why would you meet with her?”
He said, “She wants to help entrepreneurs.”