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Transform Success Into Significance

The Upside brings together a diverse group of leaders —executives, investors, entrepreneurs, and creators— interested in having meaningful economic and social impact.


Experience The Power of The Upside

Receive private, curated matches with members based upon mutual goals and interests.

Let The Upside facilitate introductions so you can focus on what matters most: your impact.




Real. Meaningful. Connections.

We believe connecting the right people can unlock amazing possibilities. Let us take care of the hard work of finding and reaching those people. Pick your goals and let’s get started!

Before you know it, you’ll be on your way to a purpose-filled business life.

The Upside Member Benefits

Platform Tools

Research and explore opportunities, review matches, schedule meetings, and privately interact with the community.

Exclusive Programming

Exclusive programming from inspired thinkers that challenges you to reflect, re-energize and refocus.

Concierge Support

Get concierge support from a real person who can assist you in navigating The Upside and uncovering opportunities.

Featured Professional Members

Bob has been involved supporting high growth companies for more than twenty years as an investor, advisor, board member or founder. He was an early General Partner at Spectrum Equity, helping the firm grow to over $4B of capital across five funds. He has served as a board member/observer for over a dozen companies, and gained extensive operational experience working alongside portfolio executives while leading their acquisition and capital markets activity. His notable investments include Patriot Media Holdings (sold to Comcast for $493 million), Classic Media (sold to Entertainment Rights, plc for $305 million), Jazztel (IPO) and ITXC (IPO).

After Spectrum, he became an entrepreneur, building an alternative asset manager from “white board” to a successful exit via a strategic deal with BNY Mellon. Since leaving BNY Mellon, he has been active as an investor and advisor to both early and growth stage private companies, including Hometap Equity Partners (a General Catalyst-seeded fintech). His areas of interest are Internet, software, fintech and technology-enabled services companies.

Earlier in his career, he worked a consultant at Bain & Company in Boston and was a member of the Charter class of Kauffman Fellows.

Bob is a proud Pittsburgh native, but has lived in the Boston area since graduating from Williams College with Honors in Economics. He received his MBA with High Distinction from Harvard Business School and was a Baker Scholar.

Robert Nicholson

Investor, Advisor

Prag (Pragnesh) Shah is a global revenue growth, customer experience and transformation leader at publicly-traded and private-equity consumer companies. He has provided value-creation and innovation domestically and in Europe and Asia for companies across multiple industries. Most recently he was Global Head, Customer Experience & Innovation for Princess Cruises, leading broad transformation for the $4B cruise line at the intersection of guest experience, employee experience and digital, IoT technologies in hospitality.

A strategic operator from the Boardroom to the front-lines, his prior roles include Global Consumer President for E-learning company Rosetta Stone and COO for Zubie in the mobile automotive services sector. Previously, as VP E-Commerce for General Atlantic’s portfolio company, Network Solutions, he led the revenue turnaround driving a $600M exit to Group. His post-MBA career began with 10 years in E-commerce, customer, and innovation executive roles at Sprint.

Prag’s early career started as an aerospace engineer at NASA. His intersection of business and technology leverages his MBA from Harvard Business School, and MS and BS engineering degrees from George Washington University. He currently serves on the Board of Pratham, a non-profit driving literacy education in India and Africa. He also serves as an advisor, investor, and transitional executive to B2C companies.

Prag is an outdoor enthusiast having done immersive travels on all seven continents and is an active certified ski instructor. He also enjoys creative pursuits via photography and design.

Prag Shah

Digital Transformation, Customer Experience

Emmanuelle leads all the post-sale customer-facing functions at Toast as the Senior VP of Customer Success. She sits on the advisory board of four startups and is a frequent industry speaker and blogger. Prior to Toast, she lead Sales & Customer Success at DigitalOcean, scaled Influitive 10x in two years leading Sales, and ran the Global Channel Sales at Sophos. She was also the first hired sales person at Endeca and Vertica and was fortunate to see both through rapid growth and successful acquisitions.

She holds a B.S. in Industrial Management from Carnegie Mellon University and an M.B.A. in Marketing and Finance from New York University’s School of Business.

Emmanuelle Skala

SVP Customer Success, Advisor, Board Member, Investor

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