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Learn by Stage
  • Starting
    • Idea Generation
      • Vision, Mission, and Enlightened Capitalism
      • Why You Should Start Before You Think You’re Ready
      • Wendy Tsu Shares Quick Tips on Ideation & Teams
      • How Do You Identify a Big Idea? AlleyCorp’s Kevin Ryan Shares Tips
    • Founding Team
      • 5 Tricks To Starting a Venture with Your Partner
      • Should You Add a Co-Founder?
      • Choosing a Co-Founder? How to Find the Right Person
      • Going Solo: Founding a Startup without a Co-Founder
      • Kevin Ryan Shares Insights on What Makes Great CEOs
    • Founders' Agreements
      • 3 Topics To Discuss Before Writing a Founders’ Agreement
      • Reasons to Write a Formal Founders’ Agreement
      • Key Terms to Include in a Founders’ Agreement
    • Equity Splits
      • Co-Founder Equity Splits—Ways to Approach Allocations
      • Why You Should You File an 83(b) Election
      • Structuring Equity Splits to Mitigate Co-Founder Conflict
      • Layering Value—A Different Way of Dividing Founder Equity
    • Fundraising
      • 3 Hacks for Calculating How Much Your Startup Needs to Raise
      • How to Build a Great Pitch that Hooks Investors
      • Should You Bootstrap?
      • Navigating a Deal Before You Sign a Term Sheet
      • Common Funding Mistakes when Scaling
    • Perspectives on Raising Venture Capital
      • Raising Money at an Early-Stage Startup? Tips from Joro’s CEO
      • What Qualities Do VCs Look for in Founders? Investor Nick Grouf Shares Insights
    • Fundraising Docs
      • Common Terms & Their Implications
  • Building the Business
    • Co-Founder Fit
      • Quick Tips for Finding Co-Founder Fit from Sunil Nagaraj
      • Searching for a Co-Founder? Lara O’Connor Hodgson on Why Perspective Matters More than Skills
      • Dinesh Moorjani on Finding the Right Co-Founder
    • Mental Health & Well-Being
      • Debunking Myths about Parenting While Founding a Startup
      • 5 Tricks To Starting a Venture with Your Partner
      • Strategies for Optimizing Wellness & Productivity
      • Entrepreneurs, Stress & Depression
      • Entrepreneurs and Depression—Ways to Help Yourself or a Colleague Who Is Struggling
    • Founder-CEO Roles & Challenges
      • Want To Build the Next Unicorn? Presence Matters More Than Capability
      • Saving the Planet from Your Smartphone: Sanchali Pal on Leading a Mission-Driven Startup
      • How to Mentally Prepare for a Difficult Conversation
      • How to Express Empathy While Working Remotely
      • Staying Motivated through Disappointments & Failure
      • Mindfulness & Entrepreneurs: How Meditation Makes You a Better Leader
      • Managing the Pressures of Rapid Growth
      • Sunil Nagaraj of Ubiquity Ventures on Co-Founder Compatibility
    • Recruiting & Retention
      • Thinking about Firing Someone? CEOs Share Advice for Framing Your Decision
      • Want to Build a Strong Team? Spend More Time on Recruiting—Not Money
      • AlleyCorp’s Kevin Ryan on Traits of Great Business Leaders
      • How Hiring for Growth Mindsets Can Help Your Startup Scale
    • Board & Advisors
      • Ways To Improve Your Relationship with Your Board
      • How To Get More Value from Your Board
      • 5 Mistakes Founders Make with their Boards—and How to Avoid Them
    • Culture
      • Strategies for Building a Strong Remote Team Culture
      • How Culture Helped Careem’s CEO Scale a Startup into a Unicorn
      • How Mission Helps You Build the Best Team
    • Joining a Startup
      • How to Value Your Equity at an Early Stage Startup
    • Product: Customer-Problem Fit
      • Turn Your Idea into a Product Users Want: Identify the Right Problem
      • Customer Interviewing Techniques That Uncover Your Users’ Unmet Needs
  • Scaling
    • Sales Fundamentals
      • What Founders Should Know about the Sales Process
    • Sales, Marketing & PR
      • What Founders Should Know about the Sales Process
      • Tinder’s Co-Founder Shares B2C Marketing Strategies
      • Tips for Technical Hardware Startups Working with Enterprise Customers
    • B2B
      • Tips for Technical Hardware Startups Working with Enterprise Customers
    • B2C
      • Tinder’s Co-Founder Shares B2C Marketing Strategies
    • How to Scale
      • Magnus Olsson on How To Find Your Purpose
      • 3 Consequences of Hypergrowth & How to Prepare
      • Tips for Scaling Startups from NOW Corp’s CEO
      • Why You Should Focus on Mission & Communication as You Scale
      • Scaling Your Startup? Focus More on People
      • Scaling Myths That Could Impact Your Startup
  • Exiting
    • Exit Strategies
      • CEO Dulcie Madden on Navigating Cash Flow Shortages & Adversity While Raising Your Family & Team
Expert Insights
  • Wes Hall on Systemic Racism—How It Affected Him and Why He Felt Obligated To Act
  • Wes Hall on Motivation for Founding BlackNorth Initiative
  • Wes Hall on the BlackNorth Initiative CEO Pledge and Summit
  • Wes Hall’s Rise from Mailroom Courier to Board Room Exec

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Workshops
  • Pitching 1
    • How to Build a Great Pitch that Hooks Investors
      • How to Build a Great Pitch the Hooks Investors
      • Guide for How to Build a Great Pitch the Hooks Investors
  • Pitching 2
    • How to Convince Investors to Make the Leap
      • How to Convince Investors to Make the Leap
      • Guide for How to Convince Investors to Make the Leap
  • Fundraising Basics
    • How Much Funding Do You Really Need to Raise?
      • Guide for How Much Funding Do You Need to Raise?
      • How Much Funding Do You Need To Raise?
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Contributor

Nick Grouf
Nick Grouf on Twitter Nick Grouf on LinkedIn Nick Grouf website link
Nick Grouf

Managing Partner, Alpha Edison and serial entrepreneur

A serial entrepreneur, investor, and philanthropist, Grouf has more than two decades of experience in finance and technology, founding Clementine Capital, a technology-based incubator (2011), Alpha Edison, a venture capital fund (2016) and co-founding several tech-startups including Firefly, (acquired by Microsoft, Inc.),  PeoplePC (acquired by EarthLink).

Firefly

Originally known as Agents, Inc., Firefly invented collaborative filtering personalization technology which could predict a user's tastes based on previously gathered preferences. Conceived in 1995 and focused on music, Firefly grew out of a project at the MIT Media Lab and was co-founded by Grouf, David Waxman, Pattie Maes, Max Metral, Upendra Shardanand, and Yezdi Lashkari. Grouf served as CEO and president of Firefly which, within a year of launching had built a community of more than 3 million users.

Firefly, which collected large amounts of personal data, implemented tools and systems for users to manage and note privacy preferences. Key contributors to OPS (Open Profiling Standard), the company developed the underlying data management technology which was later known as the P3P (Platform for Privacy Preferences). In April 1998, Microsoft acquired Firefly, and Grouf continued as Head of Privacy for a year, creating Firefly Passport (which became Microsoft Passport) and developing the .NET platform.

PeoplePC

After leaving Microsoft, Grouf became E-I-R at SoftBank Technology Ventures before co-founding PeoplePC with Waxman and Metral in 1999. WIth a mission to democratize technology, the company bundled personal computers with internet service and access to discounted products and services and PeopleGive, a separate 501(C)3 entity which provided computers and connectivity to low income people. Grouf served as Chairman and CEO for four years, working with firms such as Ford Motor Company, Delta Airlines, and the New York Times, helping give employees home Internet access. Its business model included collective buying, which allowed the company to generate additional revenue from advertising, partnerships, and premium products. PeoplePC debuted on NASDAQ in August 2000, and in 2002 the company was acquired by Earthlink. Following the sale, he spent six months working within EarthLink as Executive Vice President and CEO of PeoplePC.

Spot Runner

In 2003, Grouf worked with Waxman to create online-fundraising strategies for John Kerry's presidential campaign. After discovering barriers in the television advertising infrastructure, they co-founded Spot Runner, a platform which helped businesses customize effectiveness of pre-produced TV commercials by targeting ads to specific markets, after an algorithm determined the optimal time and locations of the ads.

Clementine Capital

In 2011, Grouf founded Clementine Capital, a Los Angeles-based technology incubator. Through Clementine, Grouf has developed his own ideas and provided resources, capital and strategic guidance for independent entrepreneurs and early-stage companies in both the consumer and business-to-business sector. Among others, he has worked with The BabyBox Company, Lootcrate, Pluto TV and Fig, which was acquired by eBay

Alpha Edison

In 2016, Grouf collaborated with former Goldman Sachs technology banker Michael Parekh and VC Nate Redmond to form Alpha Edison, a venture capital fund. Grouf serves as Managing Director and within a year of its founding, The Los Angeles Times reported that Alpha Edison was raising $300 million to invest in startups in addition to a $30 million side fund.

Background

Grouf completed his undergraduate studies at Yale University in American Studies, graduating with honors and composing an opera that won “best thesis” recognition. After working as a consultant with McKinsey & Co. from 1990 to 1992, he pursued an MBA program at HBS. While earning his MBA, hw held a position as Associate in Mergers & Acquisitions with Goldman Sachs.

Grouf has served on the board of 60Frames (now part of the United Talent Agency) and maintains affiliation with a number of professional organizations, including the National Center for Women & Information Technology and the education-focused SEED Foundation. He has established scholarships at Harvard University, Yale University, and the Horace Mann School in New York, emphasizing work in entrepreneurship and social health issues

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Contributions

  • Learn By Function

  • people seated at different sides of a conference table, person closest to camera is observing two people across the table, suggesting he is evaluating them for qualities VCs look for in startups
    Starting: Perspectives on Raising Venture Capital

    What Qualities Do VCs Look for in Founders? Investor Nick Grouf Shares Insights

    In this short, focused interview with Shikhar Ghosh, Nick Grouf identifies the qualities and competencies that signal future success for many investors. He offers insightful takeaways about the importance of your business model, team composition, clarity of thought, and attitude towards risk that can help entrepreneurs understand what VCs want.

    6 min read
  • Building the Business: Recruiting & Retention

    Thinking about Firing Someone? CEOs Share Advice for Framing Your Decision

    What do you do when your instinct tells you that someone has the potential to drag your company down? Deciding to let someone go is costly, complicated, and emotionally draining for everyone involved. Five entrepreneurs share tips on deciding to fire an employee—and how to do it in the least disruptive way possible.

    11 min read
  • Scaling: How to Scale

    Scaling Your Startup? Focus More on People

    What sets apart a founder who scales successfully? Many say it's shifting your focus away from executing to building and managing your team. HBS professor Shikhar Ghosh talked with serial entrepreneur and investor Nick Grouf. In this quick exchange, Grouf shares core insights on why founders need to focus more on people, especially as their business scales.

    5 min read
  • people seated around conference table, at a meeting, discussing how to get value from your board of directors
    Building the Business: Board & Advisors

    How To Get More Value from Your Board

    How can you benefit from the experience of board members and get more value from your board? In conversations with serial entrepreneurs, we explore ways to reframe your relationship with your board. Learn to maximize their value to your business and strengthen your relationship.

    7 min read

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