David Siegel

Former CEO of Meetup, author of “Decide & Conquer”, and host of the “Keep Connected”

A recognized leader in developing innovative products, expanding revenue, and creating vibrant communities. He has driven growth and innovation at companies such as Meetup, Investopedia, and DoubleClick, transforming the way people connect and interact.

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Full Profile

David Siegel is a visionary business leader and speaker, renowned for helping organizations drive innovation, achieve rapid revenue growth, and build thriving communities in the digital age. As the former CEO of Meetup, Investopedia, and President of Seeking Alpha, he brings over 25 years of executive experience across technology, media, and e-commerce, making him one of today’s most influential voices on digital transformation and strategic management.​

David Siegel’s leadership journey is defined by his ability to address complex business challenges such as accelerating digital traffic, scaling operations beyond the startup phase, transforming company cultures, and cultivating high-performing teams. He is equipped with deep expertise in M&A, turnarounds, strategic planning, process improvement, and adapting organizations to meet evolving customer needs in competitive markets. With a Bachelor’s in Philosophy, Politics, and Economics, and an MBA in Finance and Marketing from the University of Pennsylvania, he complements his professional accomplishments with a strong academic foundation.​

As an adjunct professor at Columbia University and host of the top-rated “Keep Connected” podcast, Siegel is celebrated for his ability to share real-world insights on the power of community, entrepreneurial mindset, and effective decision-making. His book, “Decide & Conquer,” distills decades of executive wisdom into a practical framework for seizing opportunities and overcoming uncertainty.​

Speaking Topics & Business Challenges Addressed

David Siegel’s tailored talks and consulting engagements focus on pressing business and societal challenges, including:

  • Driving Growth & Innovation: How to foster continuous innovation, strengthen brand identity, and unlock new revenue streams.​

  • Workforce Transformation: Strategies for building agile teams, attracting top talent, and navigating change management in turbulent environments.​

  • Community Building: Why fostering authentic connections is essential for employee engagement, customer loyalty, and organizational success.​

  • Technology-Driven Strategy: Making technology a differentiator in markets disrupted by digital platforms.​

  • Work-Life Balance & Success: Lessons in sustainable leadership, prioritizing well-being for long-term performance.​

  • Decision-Making for Leaders: His “Decide & Conquer” approach to taking control of your choices and generating luck in business.​

  • Social Impact & Loneliness: Navigating the mental health crisis and leveraging technology to nurture meaningful relationships.​

Why Book David Siegel

Clients praise David Siegel for his engaging stage presence, actionable insights, and ability to inspire reflection and change. Whether addressing global summits, corporate off-sites, or leadership workshops, his talks deliver practical takeaways backed by real-world success stories. Siegel’s expertise is ideal for organizations seeking strategies on digital transformation, organizational resilience, and fostering cultures of innovation and belonging.

Talks

Why Community is the Ticket to a Happier Life and How to Find It Now

We live in one of the loneliest times in human history. 46% of American adults identify as lonely, and 25% feel they lack a trustworthy confidant. The pandemic has only further distanced us, and our health is at stake. David Siegel, the former CEO of Meetup, will explore why adults struggle to form authentic connections and share how people are using technology to find real friendships. Since 2002, Meetup has been the go-to platform for connecting with others through shared interests. Gain valuable insights from the only social networking platform that wants its members to log out of their devices and connect in real life.

Why Luck is Under Your Control: How to Create Your Own Luck

Why are some people prone to luck while others always seem unlucky? Learn from former Meetup CEO David Siegel how daily decisions can influence your opportunities and make you luckier. David guides you through his powerful decision-making framework in Decide & Conquer that will help you seize the choices under your control and generate favorable outcomes.

How a Better Work-Life Balance Can Make You More Successful

Despite a rapid career that included becoming an executive at the age of 26 and a CEO at 40, former Meetup CEO David Siegel prioritized work-life balance above all throughout his career. Learn from the author of Decide & Conquer how making a fulfilling life outside of work an advantage rather than an obstacle can lead to greater success.

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