When Sig Mosley was a fresh 20-something staff accountant at Atlanta-based software developer Management Science America, he was the quiet kid raising his hand in the back of a room full of suits and financial bigwigs.
“I always seemed to know where the things they wanted to know about were,” says Mosley, who went on to become a vice president at that company. “Here I was, this little blond-headed kid, and I’d just show up with the answer. I was always just there.”
Always there. It’s a common refrain about Mosley, a prolific early-stage investor who has been a constant in Atlanta’s tech industry since 1990, when the internet was in its infancy and the term angel investing didn’t even exist. As former president of Imlay Investments and head of his own fund, Mosley Ventures, he has backed more than 145 burgeoning companies and turned a profit on 106 of them—an astonishing rate during a time when 75 percent of venture capital-backed start-ups failed. His approach—nurturing entrepreneurs in addition to funding them—plus the sheer number of his disciples, may be what has earned him the moniker “the godfather of angel investing” in Atlanta. By all accounts, his nature is patient, affable, firm, and wise—even fatherly.
This approach seems to have paid off: Many of Mosley’s protégés have achieved huge success. Most spectacularly, he invested early in then-26-year-old Daniel Aegerter and his B2B e-commerce software company Tradex Technologies, which went on to hold the record as the largest venture deal in the Southeast.
Mosley bought in during the company’s infancy in 1995, when the company was going through a dicey period. But Mosley leaned in. “He’s someone I would reach out to for advice,” says Aegerter, who now lives in his native Switzerland, where he helms his firm, Armada Investment. “He was in the details, he was in the know, and he cared.” Five years later, Tradex sold at the height of the dot-com bubble in 2000 to Silicon Valley-based Ariba in an all-stock deal valued at $5.7 billion, landing Mosley with a return 180 times his investment.
Stats like that often intersect with arrogance, but not with Mosley, who cultivates an aw-shucks persona (while simultaneously eyeballing a complicated spreadsheet and pinpointing a formula error). He attributes just showing up, sticking around, picking up the phone, raising his hand, and a willingness to take on any task, big or small, as keys to his success.
“He’s the kind of guy who will roll up his sleeves,” says Melanie Leeth, who took over as president of Imlay Investments when founder John Imlay and Mosley stepped down in 2012. Leeth and Mosley have worked together for 30 years; she considers him a mentor. “He’s just a doer. He’s one of the most amazing multitaskers I’ve ever met. He has the capacity to see the big picture, but he’s also really good at remembering the details.”
If Mosley invests, he digs in. He doesn’t bail when things get slippery. “He does what he does to build the community,” says Leeth. “He really believes a rising tide lifts all boats. He’s always there to take the phone call.
The Wonder Years
Mosley grew up an only child, the son of a car salesman/banker and a homemaker in the Appalachian foothills in Jasper, about an hour northwest of Atlanta. In high school, he mowed lawns, worked the school concession stand, wrote for the school newspaper, was a Boy Scout, and cleaned the Baptist church as an assistant janitor. He describes his youth as old-fashioned and fairly unremarkable—he wasn’t an ace student or athlete, but he did a lot of things well. He was industrious, but he also liked to cut class and had an understanding with the local cops that he could drive a car long before he had a license. During his senior year at Jasper High School, he was voted “most dependable.” In 1964, he left the mountain town for Oxford College of Emory University, where he fell in love with accounting and later graduated with an accounting degree.
After a short stint as an auditor, Mosley became the 700th hire at Atlanta-based Management Science America (MSA) in 1968.
“Being the brilliant accountant I was, I joined,” he jokes self-effacingly. “They were financially insolvent.” It turned out to be a good decision, although the company “led for bankruptcy in 1971 and shrunk from 800 employees to 45. Mosley was kept on as one of two in accounting, eventually becoming a vice president in 1980 and working under John Imlay, who bought the company and turned it around. This act of fate shaped Mosley’s entire career.
MSA went public in 1981; it was a $330 million company when it sold to Dun & Bradstreet in 1990. By that point, Mosley had become Imlay’s right-hand man, and when Imlay took the proceeds to launch Imlay Investments, he brought Mosley along to manage it, with the express intent of fostering entrepreneurs and building up the tech community in Atlanta. “Now it’s called angel investing,” says Mosley. “Then, it wasn’t called anything.”
When the pair set out, they were pioneers, and Atlanta’s tech scene was in its infancy—the VC scene even more so. The internet was young, and it wasn’t clear where it was going. Atlanta was a real estate town, an airline town, and a building supplies town, not a tech town. But Imlay was already well-known in the tech sector from MSA, and the pair started cutting checks, primarily in the security, big data, and healthcare software sectors. Their styles were different, but their goals were the same. (Imlay, who was known to have a flair for the dramatic, more than once brought Bengal tigers to company meetings to inspire employees to “be a tiger in business.” Mosley hardly gives off tiger vibes. More like the aura of a St. Bernard, the famously patient and watchful rescue dog of the Alps.) Their vision was simple: support entrepreneurs, mentor them, watch them grow and multiply, make Atlanta a tech hub.
Mosley has never been a suit-and-tie guy, which fits his mellow persona. He’s been dressing like a tech bro since long before the pandemic, dropping the tie from his white collar uniform decades ago, and then the coat, and then the top button, until finally, he landed in a T-shirt, hoodie, and Allbirds. His gaze and features are soft, he’s easy to talk to, and his feathers don’t readily ruffle. For Mosley, investing is all about connecting with people.
“Gut” is another term that surfaces often when you ask people about Mosley, including from Mosley himself. “A lot of it is gut [instinct],” he says. “You have to find out if people want to solve problems. If they’re passionate, honest, trustworthy.”
Mosley and Imlay took a leap of faith early on, in 1994, with Internet Security Systems (ISS), at a time when few investors understood why the internet needed to be secured, or even what the internet was. Founders Tom Noonan and Chris Klaus came to them and laid out 36 maxed-out credit cards. Noonan was five months behind on his mortgage, with three kids at home. “We kind of hemmed and hawed,” says Mosley. “But we believed in ISS, and we believed in them.” He cut them their first six-figure check.
Ten years later, IBM bought the company for $1.2 billion.
ISS proved so successful that it ended up as an incubator for further talent. Patrick Taylor was employee number 12 at the company. In 2003, he launched Oversight Systems, an auditing software company. Mosley was among the original group of angel investors, and Taylor recalls the air of credibility that gave him.
Routinely, when Mosley was a lead investor in a company, he would form a special-purpose LLC that other investors would buy into, as he did with Oversight Systems. In this way, capital would be funneled straight to the entrepreneur, making life much simpler as they would only need to chase down one signature (Mosley’s) when decisions had to be made. There was no great governance behind it, other than Mosley’s word, but no one batted an eye.
“It only worked because everybody trusts Sig,” says Taylor. “He’s honest and incredibly detail-oriented, and nothing’s going to fall through the cracks.”
There were times, Taylor says, when he was stuck between receivables and making payments. Rather than get a loan from a bank, he’d call Mosley and ask for a short-term note from the bank of Imlay Investments. “I don’t want to think about how many times I had to do that,” says Taylor. “To have somebody who would bridge that gap—it was a lifesaver.”
It was 17 years before Oversight Systems was acquired by a private equity “rm. “Sig was never anything but a positive force,” says Taylor. “He’d give you a pat on the back and say, ‘Keep at it.’”
Eye on Diversity
At 76, Mosley maintains an advisory role at Imlay and is working to wind down Mosley Ventures, which has funded 22 companies and currently maintains 10 in its portfolio. He’s tried twice to partially retire, unsuccessfully. Instead, he has turned his attention to supporting another local fund, Zane Venture Fund, which invests in diverse founders of tech companies.
Zane founder Shila Nieves Burney discovered Mosley via Google. “I searched something like ‘best angel investor in Atlanta,’” she laughs. “And Sig came right to the top. I emailed him, and I asked him to get coffee at the Gathering Spot and he agreed—he doesn’t even drink coffee, by the way, he drinks sweet tea. He gave me some names and said, ‘Feel free to reach out.’”
Burney took that to heart, and at one point, she said, she might have been texting him three to four times a day with questions. “I worried I was overdoing it,” she says. “But his approach was always the same,” she says. “Giving examples, sharing anecdotes, always in a mild-mannered way. He’s never said, ‘That’s a dumb question.’”
Diverse entrepreneurs—people of color, people of differing physical abilities, immigrants—and their businesses are often underfunded compared to their white, non-disabled counterparts. With Zane, Burney intends to close that gap in capital, providing funding and mentorship for young companies helmed by young founders of diverse backgrounds.
“With Zane, I thought I could have more of a positive impact,” says Mosley. “Shila is a good people-person, a good people-reader, but when she started she knew nothing about investing.”
Now, she’s met with Mosley for coffee—or sweet tea—every week for five years, and in 2020, Mosley joined as a venture partner in the $25 million fund, with eight companies in its portfolio. Burney says she still relies on Mosley as a trusted adviser, but she does most of the pitching these days, only bringing him on when she needs a heavy hitter.
Building the Future
Niesha Butler knows something of the challenge women of color face when trying to raise capital. A Black woman of Aruban and Puerto Rican descent, Butler is a former Georgia Tech and WNBA basketball star, actress, Hawks sideline reporter, software engineer, and entrepreneur. She met Mosley when she landed second place at Jesse Jackson’s PushTech competition at Morehouse College in 2015 for her amateur sports database, ScrapSports. She asked Mosley, nervously, if she could follow up with him. He said sure.
“It was my very first time pitching,” says Butler. “I didn’t know what a pitch deck was, I didn’t know what an executive summary was, I didn’t know what ROI was. I didn’t know any of that.” At the first meeting, she was visibly flustered.
“He said, ‘Calm down, tell me who you are,’” she recalls. “He was genuinely curious about me and what I wanted to do and why I thought I was the person who could do it. He said, ‘This is what you need to have before you speak to me again.’” She came back with it, and he coached her again. After several edits, he cut her first check for ScrapSports.
“What was so beneficial to me,” she says, “is that he gave me an opportunity to learn while I was building it. Now that I’m a more mature entrepreneur, I’ve asked him ‘Why did you invest in me? My pitch deck was horrible,’” she laughs. “He said something like, ‘You are an expert in the field. You didn’t realize it, but you knew what you were talking about. You had the relationships. Your company was about you, and I believed in you.’”
That swift bestowal of trust, Butler says, doesn’t come easily for Black women in technology and business. “Normally Black female founders, we have to be 20 times, 1,000 times better to get crumbs,” she says. “For a woman of color, he put a stamp on me. I really don’t know if I’d be here without him.”
Butler, who is now back in her native New York and in the seed round for the first STEAM camp in the U.S. founded by an Afro-Latina, notes that for all the patience and kindness Mosley’s shown her, he’s also got an edge and a dry sense of humor. “There’s something about his look,” she says. “He’ll just be listening to you, but there’s something about his aura that commands respect. He speaks low. He’s obviously not intense—he’s so kind—but whoever coined ‘the godfather’ term was spot on.” “He prepared me to pitch to other investors,” she says. “He set the bar high, but was also kind and patient.”
Wins and Losses
Over the years, Mosley has served on more boards than he can count—as many as 25 at one time. He’s won almost as many awards, including a Lifetime Achievement Award from TiE Atlanta, part of a global network that incubates entrepreneurs. In 2007, he was inducted into the Technology Hall of Fame of Georgia. In fact, there’s now an annual awards ceremony in his name to recognize unsung angel investors: the Siggie Awards. In the ultimate dad joke, he even requested bobbleheads made in his likeness to serve as the trophy (Mosley is, by the way, a father of seven and a grandfather of three. He lives in Brookhaven with his wife, Jodi).
Along the way, he has missed some opportunities. “We turned down Kabbage,” he says of the online lending company that sold to American Express in 2020 for an estimated value of about $850 million. “And Mailchimp. We tried to get in, but we couldn’t negotiate the terms, so we walked away.”
Adding to his stature as a local legend, T-shirts are floating around from a dejected entrepreneur that read, “Sig Said No.” Mosley gets a kick out of this.
“For every deal I’ve done, I’ve seen 100 [opportunities],” he says, “And I’ve had a lot more losers than winners—to me that’s just part of venture capital and angel investing.”
Mosley doesn’t try to take credit for Atlanta’s tech boom and the flood of investors, hubs, incubators, and flourishing companies the city has seen since his start more than 30 years ago. He gives that nod to Georgia Tech. But, he says, “I do think we helped.”