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."