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The Ins and Outs of Angel Investing

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Anna Mason
Revolution LLC, Partner

Anna Mason is a Partner in Rise of the Rest Seed, a Revolution Fund backed by many of America’s most iconic entrepreneurs, investors and executives. The fund invests catalytic capital in high-potential early stage startups that are based in regional innovations hubs in cities all across the country.

In this capacity, Anna leads the investment process for select deals in the fund across a variety of industries including the fund’s investments into Summersalt (Consumer; St. Louis, MO), Pryon (Enterprise AI; Raleigh, NC), STORD (Logistics; Atlanta, GA), Dispatch (Logistics; Minneapolis, MN), Replica (Urban Planning; Kansas City, KS), Glow (Podcast Media; Seattle, WA), and Kenzie Academy (Future of Work; Indianapolis, IN).

Anna also leads strategy and execution for the Rise of the Rest Network and Platform, including the annual Rise of the Rest Road Trip and annual Network Summit. Her passion for this work is centered around two core beliefs: investing in startups sits at the intersection of realism and optimism; Rise of the Rest is a platform that helps us see the country through the eyes of the entrepreneurs who are re-imagining its future.

Anna brings over a dozen years of experience in finance, startup operations, and venture community programming to Revolution. Prior to joining Revolution, she co-founded a fitness-community startup that was acquired by Beachbody in 2015. Before that, she began her career on Wall Street, where she spent seven years as a distressed bond and post-reorg private equity trader, most recently as a Vice President at The Seaport Group.

Since 2015, Anna has worked to support early stage female founders in the DC community, through various leadership roles at The Vinetta Project DC, including as city co-director and then as co-chair of the Advisory Board (2015-2019). She was a founding member of BEACON DC, a community-led campaign to make Washington, D.C. one of the most influential and supportive cities for women entrepreneurs. She currently serves on the Board of Trustees for the National Children’s Museum, which focuses on STEAM-centric exhibits for children.

Anna received her BA in Government from Harvard College and her MBA from the NYU Stern School of Business. She was named to Business Insider’s list of 100 People Transforming Business in 2019, a Washingtonian Tech Titan in 2017 and 2018, Washington Life’s Tech25 in 2017 and featured in Inc. Magazine's 2019 coverage of Washington, DC.

In 2015, she published a book based on her Wall Street experiences during the 2009 financial crisis called They All Fall Down.

Juan Pablo Segura
Babyscripts, President

Juan Pablo is the President and co-founder of Babyscripts. Under his leadership, the company launched the sale of the Babyscripts virtual maternity care solution in May of 2015, converting several large hospital systems into customers within its first year of business. His primary roles and responsibilities include establishing and cultivating strategic relationships, such as the company’s partnerships with Startup Health, Philips, and General Electric, among others. Juan Pablo manages both the day-to-day and long-term finances of the company and recruits key personnel to implement the strategic vision of the company. Juan Pablo has been named a “Healthcare Transformer” by the Startup Health Academy in New York City and a “Wireless Lifechanger” by CTIA for his work in delivering more effective technology tools for pregnant patients.


Prior to his work in entrepreneurship, Mr. Segura was a Risk and Tax Consultant for Deloitte and Touche, where he advised several large corporations on matters of risk mitigation, bankruptcy liquidation, and international tax planning. He graduated Cum Laude from the University of Notre Dame and is a Certified Public Accountant.

Melissa Bradley
1863 Ventures, Founder & Managing Partner

Melissa L. Bradley is a co-founder of venture-backed Ureeka, a community where small businesses gain unprecedented access to the expertise needed to grow their business. The Ureeka mission is to democratize economic opportunity by enabling community and by reducing the cost and risk associated with growing a small to medium business (SMB). She is also founder and Managing Partner of 1863 Ventures, a business development program that accelerates New Majority entrepreneurs from high potential to high growth. In this role she created a community of over 10,000 New Majority entrepreneurs in three years. Melissa is a Venture Partner at NextGen Ventures and serves an advisor the New Voices Foundation and New Voices Fund, as well as the Halcyon Fund. Melissa is the former Co-Chair, National Advisory Council for Innovation and Entrepreneurship and was recently named one of The Most Entrepreneurial Women Investors in 2018.

Tien Wong
Opus8, Inc., CEO

Mr. Tien Wong is a tech entrepreneur, CEO, and angel investor. He is Chairman & CEO of Opus8, Inc., a private investment and strategic advisory firm specializing in tech investments and fundraising for alternative investment funds and companies seeking to raise capital. Opus8’s Phoenix Fund makes early stage investments in remarkable fintech, proptech, healthtech, and martech companies that are disrupting their markets and changing the world. Tien is Chairman of Lumious, a Virginia-based EdTech company which provides advanced tech training, mobile e-learning, and software development to Fortune 500 customers. He is also Chairman of Lore, a national provider of IT and business process outsourcing services to commercial and government clients.

Tien has made direct investments in over 25 early stage companies and VC funds. He has been an investor/shareholder and mentor to several successful companies including Parature (exited to Microsoft for $100 million+), Transactis (exited to MasterCard), DataRPM (exited to Progress Software), LiveLook (exited to Oracle), TerraCycle, and TopBox, among others.

Tien has assisted several dozen leading venture capital and private equity fund managers in raising institutional and family office capital. Some of these clients include Morgan Stanley, Blackstone, Mitsubishi Corp., TPG, Ares, StepStone, HarbourVest, Thomas H. Lee, K1, and US Venture Partners.

In 2012, Tien created the Big Idea CONNECTpreneur Forum, a now-global community of over 20,000 founders, CEOs, angels, VCs, CXOs and other business leaders. The community hosts bi-monthly live Forums with upwards of 600 attendees, as well as monthly virtual online Forums and pitch events with several hundred attendees. Events feature VIP guests, speakers, exciting presenting companies, and the best CXO to CXO networking on the East Coast.

In 1991, Tien co-founded and served as Chairman & CEO of CyberRep, Inc. until its acquisition in 2003 by ACS, a “Fortune 500”company which was then acquired by Xerox. CyberRep was one of the world’s largest privately held CRM outsourcing companies, operating 9 customer interaction centers throughout the USA with over 2,300 employees and $80 million in revenue. Today, the CyberRep business units comprise about $2 billion in revenue as divisions of Xerox and Conduent. CyberRep garnered multiple prestigious awards including Customer [email protected] Solutions magazine's MVP Quality Award and Customer Interface magazine's ACCE (Award for Call Center Excellence), as well as INC. magazine's 1997, 1998, 1999 and 2000's "Inc. 500" recognition as the 51st, 53rd, 72nd and 408th fastest growing private company in the USA, respectively. CyberRep was profitable for 11 consecutive years and was backed by Allied Capital Corporation, a $5 billion investment company.

A recognized international expert in CRM, direct marketing, and BPO, Tien has presented at dozens of conferences around the world. He has also provided industry commentary on the ABC, Fox, NBC, CNBC, Maryland Public Television, and China’s CCTV networks, as well as for publications such as Time Magazine, The Washington Post, Inc. Magazine, and Success Magazine.

Tien received the 2001 Ernst & Young Entrepreneur of the Year award for Greater Washington and the 2003 Ernst & Young Performance Excellence Award. He was inducted into the Ernst & Young Entrepreneur of the Year Hall of Fame. He was recognized by Washingtonian magazine as a “Tech Titan” in 2017, 2018, and 2019. Tien is a 2012 and 2013 Washington Business Journal "Power 100" selection as one of the region's most influential leaders, a three-time SmartCEO Magazine selection as a "Smart100" CEO ('09, '10 and '11), a 2013 DCInno "Fifty on Fire" awardee, community service honoree as a member of Greater DC Cares 2009 "Class of Change” and The Gazette of Politics and Business selection in 2010 as one of "25 CEOs You Need to Know." He is a member of YPO and is a frequent guest lecturer on entrepreneurship, leadership, venture capital, and private equity at the University of Maryland and Georgetown University, where he is an Entrepreneur in Residence.

Tien was appointed by Governor Martin O'Malley to the 9-member Maryland Venture Fund Authority which oversees $84 million in venture capital allocations; he serves on the Boards of Directors of the Montgomery County (MD) Economic Development Corp. and Junior Achievement of Greater Washington. He serves on the Investment Advisory Board of the Commonwealth of Virginia's Center for Innovative Technology GAP Fund and is a Mentor at the Mach37 Cybersecurity Accelerator and Conscious Venture Lab. In the past, he has served as Treasurer and National Board Member of the American Teleservices Association; Chairman of the Executive Leadership Committee for the Network For Teaching Entrepreneurship (NFTE); Trustee of the Baltimore Symphony Orchestra, and on the Boards of the Maryland Tech Council, Association for Corporate Growth - National Capital, Digital DC Tech Fund, Northern Virginia Chamber of Commerce, Potomac Officer’s Club, Trade-Up Capital Fund, Monte Jade Science and Technology Association, FounderCorps, and Startup Maryland. He is a graduate of Dartmouth College.

Stefan A. Nagey
Capbase, Inc., Cofounder

A serial entrepreneur, Stefan cofounded Capbase to democratize the creation of tech startups. Capbase focuses on giving entrepreneurs the best start possible: form a company, incentivize employees with stock, raise money, and reducing administrative overhead. Capbase will take care of your corporation so that you can focus on building your business. Prior to founding Capbase, Nagey had successful exits of three companies to private and public buyers.


Join us for an interactive panel discussion to learn what entrepreneurs need to know about raising money from angel investors. The panel will discuss investment strategies, what angels look for when investing, common deal structures, key terms from the investor and founder perspective.