David Siegel
Most leadership writing is produced from the outside in. Operators who have made the hard calls at the centre of a company, the carve-outs, the layoffs, the pricing pivots, rarely sit down long enough to write them up. Boards and executive teams want guidance from someone who has lived the decision, not theorised it.
David Siegel is the former CEO of Meetup and Investopedia who turns the decisions a sitting CEO actually faces into a working playbook for senior leaders and founders scaling under pressure.
Full Profile
Why organisations work with David Siegel
- He led the carve-out of Meetup from WeWork to AlleyCorp in March 2020, a transaction completed inside the first weeks of the pandemic, and can speak from inside the deal rather than around it.
- He took Investopedia through a near-fivefold valuation increase and the sale to Dotdash, which gives him operator authority on building a category-leading consumer brand and exiting it.
- His book, “Decide and Conquer,” published by HarperCollins Leadership, gives audiences a structured 44-decision framework written from the chair, not the seminar room.
- He teaches strategic planning and entrepreneurship at Columbia University, which means the operational material is sharpened by working with the next generation of founders and senior leaders.
- His “Keep Connected” podcast has turned community-building into a measurable commercial discipline, useful for organisations rebuilding internal engagement or customer affinity.
Biography highlights
- Former CEO of Meetup; led the company through the WeWork-to-AlleyCorp acquisition in March 2020.
- Former CEO of Investopedia; led the sale to Dotdash after tripling revenue and driving a near-fivefold valuation increase.
- Former President of Seeking Alpha and former SVP at 1-800-Flowers; early-career executive at DoubleClick.
- Author of “Decide and Conquer: 44 Decisions that will Make or Break All Leaders” (HarperCollins Leadership).
- Adjunct professor at Columbia University, teaching strategic planning and entrepreneurship.
- Bylines in Harvard Business Review, MIT Sloan Management Review, CNBC, Business Insider, and Entrepreneur.
Biography
Meetup was a difficult business when David Siegel inherited it. It had been bought by WeWork, was burning cash, and was about to face a pandemic that emptied the rooms where its product lived. Inside eighteen months, he had made it profitable for the first time in its history, and in March 2020, he led its carve-out to a consortium led by AlleyCorp.
That arc, distressed asset to functioning standalone business under pandemic conditions, is what gives his speaking work its weight. Before Meetup, he was CEO of Investopedia, where he tripled revenue and led the sale to Dotdash at a near-fivefold valuation. Before that, President of Seeking Alpha and an SVP at 1-800-Flowers, with an early-career chapter at DoubleClick.
His book, “Decide and Conquer,” published by HarperCollins Leadership, is organised around the 44 decisions he argues a new chief executive will face. It is a working playbook, not a memoir, and it draws on the specific judgement calls, hiring, pricing, communications, and board management that he made in the seat.
He teaches strategic planning and entrepreneurship at Columbia University, hosts the “Keep Connected” podcast on community as a business lever, and has published bylines in Harvard Business Review, MIT Sloan Management Review, CNBC, Business Insider, and Entrepreneur. The teaching and writing keep the operator material structured; the operator material keeps the teaching honest.
Key speaking topics
- Decision-making for chief executives and founders
- Community as a commercial growth engine
- Carve-outs, turnarounds, and post-acquisition leadership
- Scaling consumer internet businesses
- Building and selling category-leading brands
- Entrepreneurial leadership through crisis
Ideal for
- Founders and CEOs of scaling businesses, particularly those facing a financing event, carve-out, or sale
- Boards and executive teams working through restructure, integration, or post-acquisition leadership questions
- Senior commercial and product leaders rebuilding customer community or engagement at scale
Audience outcomes
- A working set of decision frames drawn from a real CEO seat, not a consulting model
- A clear view of how community translates into commercial outcomes, with examples from a platform business
- Specific lessons from a pandemic-era carve-out, applicable to current restructure and divestment conversations
- A sharper read on what to do in the first ninety days of a new chief executive role
Talks
A talk on community as both a personal and commercial asset, drawing on Siegel’s tenure leading Meetup.
Key takeaways:
- How community translates into retention, advocacy, and commercial growth.
- What organisations can borrow from consumer community platforms to rebuild internal engagement.
- Practical entry points for leaders trying to restart connection across a hybrid or fatigued workforce.
A talk on the decisions and behaviours that compound into what looks, from the outside, like luck.
Key takeaways:
- The decision habits that consistently widen the opportunity surface for senior leaders.
- How to read and act on weak signals in a market or organisation.
- What separates leaders who get lucky repeatedly from those who do not.
A talk arguing that sustainable performance is a commercial variable, not a wellbeing concession.
Key takeaways:
- Why exhausted leadership teams make worse strategic decisions.
- How to design executive rhythms that protect judgement over a long arc.
- The cost, in commercial terms, of treating recovery as discretionary.