A rising force in Chicago venture capital—women

Listed originally in Crains 

Women in Chicago's venture-capital industry back in 1989 didn't have much opportunity for networking, even when they traveled to Washington for the National Venture Capital Association's annual conference. After spotting the few women from other cities, they went out for dinner; the reservation was for fewer than 10, recalls industry pioneer Ellen Carnahan, who at the time was at William Blair Capital Partners in Chicago.

That gathering became a ritual that lasted nearly a decade, but the numbers didn't expand much. In the past five years, however, they have. "The pool is much bigger now," she says, pointing to her younger peer Gale Bowman at IrishAngels, who regularly assembles nearly 50 women just in Chicago.

Women are still underrepresented in venture capital, both in Chicago and nationally, with just one woman in a senior post for every four men. But a new generation of women is gaining traction working alongside men and launching their own venture firms and small funds.

As they seek to raise larger subsequent funds, women's new track record of investment returns will be scrutinized closely. "The proof is in the pudding, and the proof takes 15 to 17 years," says Maura O'Hara, the longtime executive director of the Illinois Venture Capital Association


Pensions, foundations, family investment offices and other institutional investors had $368 billion of value, both cash and assets, with U.S. venture-capital firms, as of the end of June, according to Seattle research firm Pitchbook. The firms, in turn, invest in startups and hope for big returns. They employed about 335 women in senior investment jobs, versus 1,239 men in those roles, such as CEO, chief investment officer and managing partner, Pitchbook says.

Chicago isn't a huge hub for venture funds, but it's the center of activity for Illinois. IVCA's in-state venture-capital members (a few are outside the state) have about $10 billion under management. Of IVCA's 34 active venture member firms, only three are mainly led by women. Pitchbook doesn't parse the data by region, and the IVCA doesn't have any headcount figures.

In Carnahan's era, some of the city's biggest companies gave women a boost in the industry. In her 20-year career at Blair, she became head of technology investing before co-founding Seyen Capital in 2006. Her industry pal Donna Williamson was a vice president at Baxter International from 1983 to 1992, with purview of emerging companies, before parlaying that experience into a managing director post at ABN Amro overseeing private-equity investments in health care.

Northbrook-based insurer Allstate hired a cadre of women as investment professionals in its venture-capital arm, including Sona Wang, who left with colleagues Len Batterson and Don Johnson to form Batterson Johnson & Wang in 1987, where they invested in high-tech startups. "They were just open to diversity, so that's probably what really drove it," Batterson says of Allstate.

Wang, a Korean immigrant and one of Chicago's accomplished women in the field, left the firm in the mid-1990s to join other partners in founding Inroads Capital Partners, which focused on investing in female and minority entrepreneurs. Later, she teamed with Williamson and another woman to found Ceres Venture Fund. While Wang is optimistic about the future, including for her daughter now interning at Chicago accelerator Techstars, she says it's hard to point to "significant progress." "Highly qualified women . . . are still finding their way," she says.

Both the annual Washington dinner that Carnahan instituted for the NVCA and a local women's committee of the IVCA she started there as chairman in 2009 died off. O'Hara says the IVCA women's group was dissolved to bolster national women's groups, such as the Women's Association of Venture and Equity, and avoid duplication of effort. "If those efforts fade, we will pick it back up," she says.


Wave's Midwest chapter picked up the ball in 2013 to bring together women who invest in privately held companies, including venture investing and private-equity investing in more mature companies. Women have struggled to get a toehold in both.

Wave meets a few times a year and hosts a popular annual golf scramble event, but Bowman wanted to create a group focused on venture, so she launched Chicago Women in VC in 2016. It welcomes women who touch any aspect of venture capital, from investing to marketing. It, too, is focused on networking, with cocktail hours and other social events. "The real hope is that we'll do more investing together because we're meeting on a regular basis," says Bowman, who is managing director at IrishAngels, an organization that invests about $7 million annually, mainly in businesses with a University of Notre Dame connection.

One woman in her new directory is Jessica Droste Yagan, who, along with Tasha Seitz, has been a top partner at Chicago venture investing firm Impact Engine since 2014. Yagan says that drawing more women into the process makes for smarter investing. "Having one kind of person making investment decisions is limiting," she says.

Some companies propelling women into leadership roles appear to agree. Futures exchange operator CME Group promoted Rumi Morales to head its ventures unit in 2013, and Kim Trautmann took over the venture unit at trading company DRW Holdings in 2016. Other women on the rise include Dana Wright, who was hired as a managing director at Math Venture Partners in October, and Momei Qu, a vice president who left Baird Capital in February for Penny Pritzker's PSP Capital Partners. "There is a movement of far more women getting involved," says Nancy Sullivan, who became CEO of Illinois Ventures in 2013.


Women today are taking another stab at starting their own funds. Constance Freedman, who founded Moderne Ventures, raised that firm's first $33 million fund in 2015. She got her start at Boston fund Cue Ball Capital and eventually moved to Chicago, where she led Second Century Ventures' $20 million fund for the National Association of Realtors. Now she's on the cusp of raising another fund next year.

Chicago's profile in venture has grown significantly, but the presence of women hasn't kept pace, Freedman says. It's a "network business," and people invest in people they know, she says. Until the playing field is leveled, there will be more funding for men than for women, she adds.

Gerri Kahnweiler and Cayla Weisberg also launched their own Chicago firm, InvestHer Ventures, in 2016 to invest in startups with at least one female equity partner. Morales, who left CME Group last year, is also angling to launch a fund.

Carnahan remains an investor in nine venture-capital funds through her Machrie Enterprises. For her, funds must have female investment professionals. "The more you can source from different networks, the better the deal flow you're going to have," she says. "It takes seven to 10 years to get a track record. You have to be patient and keep hanging in there."

That's key advice for anyone investing in startups, but perhaps especially for women forging a new place in the venture arena.

FastCompany: World's Most Innovative Companies, Hello Alfred

Listed originally in World's Most Innovative Companies

Founded in 2014, New York-based personal-concierge service company Alfred combines artificial intelligence with human assistants to create experiences that go beyond just picking up laundry or ordering groceries (though Alfred does that too). The Alfred platform works in conjunction with an app to provide customers with next-level services such as putting groceries away in the refrigerator and auto-ordering and restocking toilet paper. Alfred assistants also learn about customers’ usage habits, using that info to better inform the AI work. Meanwhile, Alfred has partnered with brands such as Diageo, Nestlé, and P&G to allow Alfred’s customers to test new products (and have the brands receive helpful feedback on beta goods). Available at various price points, Alfred is now focused on incorporating itself into more and more apartment buildings. In 2017, it signed a deal with major real estate company Related Companies, which added Alfred services to an additional 11,000 units while helping Related’s luxury buildings retain tenants.


2018: Top 50, Retail


Headquarters: New York, NY

Alfred On The Web





Wall Street Journal Pro: Rising Star- Constance Freedman Is Real Estate's Venture Capitalist

Rising Star: Constance Freedman Is Real Estate's Venture Capitalist

Wall Street Journal Pro Private Equity

By Scott Martin

2 May 2017

Constance Freedman wanted to earn money to travel to Italy one spring break during college, an impulse that led her to land a job as a realtor and paved the path to her future.

"It was really a college job for me," Ms. Freedman, 42, said. "It turns out you can make a ton of money."

Today her knowledge of the real-estate industry continues to pay off. She is a former managing director of Second Century Ventures, the investment arm of the National Association of Realtors, and is investing from a $33 million fund managed by Chicago-based Moderne Ventures, which she founded in 2015.

Ms. Freedman hit the radar while at Second Century with a prescient early bet on DocuSign Inc., a company now valued at $3 billion, according to VentureSource, an industry tracker owned by Private Equity Analyst publisher Dow Jones & Co.

Career Path

Ms. Freedman went into real estate in the 1990s while she attended college. Soon after graduating, she joined two startups amid the internet boom. After graduating from Harvard Business School, she worked at venture firm Cue Ball Capital. Ms. Freedman was at the National Association of Realtors from 2008-15 and launched its Second Century Ventures fund.

Notable Deals

Ms. Freedman has backed about 40 deals, including taking an early-stage stake in DocuSign Inc. while at Second Century Ventures. Previously on the startup's board of directors, she now is on DocuSign's advisory board and on the boards of TaskEasy Inc. and UrbanBound Inc. She has made 15 investments out of the Moderne Ventures fund to date.

Wit, grit and good fortune have played a part in her success. But until more recently, she had been building up an executive and investor network around a real estate-influenced startup accelerator without much forethought for a bigger roadmap. "I never had a five-year plan until about five years ago," she said. "I had some visions of what I wanted to do but never really constructed plans until after I launched the accelerator."

After years of helping make connections and solve problems in accelerators, Ms. Freedman has become more systematic in her approach. She has formalized her program, which includes about 400 executives from her network.

"First and foremost, she is an extraordinary connector," said Ken Davis, chief executive of TaskEasy Inc., which offers on-demand lawn-care services and is backed by Moderne.

Moderne's accelerator program includes speed-dating mentoring sessions between executives of established companies and startups, which aim to provide innovation to incumbents and new customers for venture-backed companies. That has turned into significant revenue for startups in the program, Ms. Freedman said.

DocuSign Chairman Keith Krach said Ms. Freedman's strategic work as an early investor in the digital document-signing company helped DocuSign achieve liftoff as an early product.

"The real-estate vertical was really a great catalyst for all of our success and all of our hyper growth," said Mr. Krach. "Constance was key to that. Of course, she had a great network. But she had an understanding of this super-complex industry."

When it comes to being a company connector, being an unbridled extrovert helps, said Ms. Freedman, whose Myers-Briggs personality type is ENFP. "I fall on the extreme side of ‘E' because of the extrovert. Being an advocate on behalf of our companies, I'd say, is the way that my ‘E' manifests itself."

Moderne's accelerator encourages people to help each other out, with the notion that what comes around goes around. There is a shared concept of "paying it forward," a mantra in which people make an effort to help others, she said.

Moderne's portfolio also includes online mortgage lender Better Mortgage Inc. and lead generation service Contactually Inc.

"I think there is another thing she is going to succeed at," said TaskEasy's Mr. Davis of Ms. Freedman. "Most of her [limited partners] represent logical exits for her portfolio companies."