Randy Haykin is a serial entrepreneur, leadership coach, philanthropist, and angel investor with over 40 years of experience in the tech and startup world. He began his career in sales and marketing at Apple, helped build Yahoo as its founding VP of Sales & Marketing, and later held senior roles at Overture, NetChannel, and Electric Minds. In 1997, he co-founded Outlook Ventures, a ~$200M early-stage tech fund, based in SF. Randy has also backed over 70 companies as an angel or VC, bringing both financial capital and mentorship to founders.  He enjoys board work and to date has been on more than 35 boards in both the for profit and not-for profit worlds.

In 2013, Randy shifted his focus to global social impact and founded The Gratitude Network, a nonprofit dedicated to accelerating social entrepreneurs in the areas of children, youth and education. His work earned the organization a national (Silver) Jefferson Award for public service in 2023.

As a seasoned executive coach, Randy has mentored more than 30 CEOs in recent years. His work with leaders focuses on leadership development, innovation through AI, and personal growth & balance.

Randy has also been a member of the faculty at UC Berkeley’s Haas School of Business as well as Cambridge University’s Judge Business School, He taught classes on Entrepreneurial Finance, Venture Capital and Creativity/Innovation at both of these schools.

In 2009, Randy created Entrepreneur Wines, a Napa-based philanthropic winery that donates all proceeds to children’s causes.

Randy holds degrees from Brown University and Harvard Business School and lives out his faith through service, storytelling, and gratitude. Randy and his wife, Patty, are based in the Bay Area, and have three daughters and six grandchildren.