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Entrepreneurship & Business keynote speakers
Kevin O'Leary
"Mr. Wonderful" — Shark Tank Investor & Finance Authority
- Keynote · Fireside chat · Moderation
- English
Headliner can arrange a booking with Kevin O'Leary or their representative. This profile is compiled from public sources; availability and fees are confirmed on request. A listing here does not imply endorsement, affiliation, partnership, or exclusivity.
Signature keynotes
What your audience walks away with
- Outcome
Cold Hard Truth — Business, Money & Life
His flagship keynote, built on the bestselling Cold Hard Truth series. Practical, no-nonsense advice: find your calling, build a dream team, turn adversity into opportunity, and grow your business and your money.
Lessons From a Shark
A behind-the-scenes look at Shark Tank: how the deals really work, what makes him invest or pass, and what 16+ seasons of dealmaking taught him about entrepreneurs, valuation, and risk.
Fireside Chat — Understanding & Thriving in an Uncertain World
His most-requested moderated format: a candid read on the economy, markets, geopolitics, tariffs, and policy — and how businesses, especially small ones, position themselves through volatility.
The AI Build-Out & the Economics of Energy
Drawn from his Wonder Valley AI-data-center work: the real economics of the AI infrastructure boom, the energy constraint behind it, and where the opportunities and risks actually are.
American Business 2.0
How business has permanently shifted — hybrid and remote work, the acceleration of online retail and direct-to-consumer — and what the new operating environment rewards.
Money, Investing & Personal Finance
From the Cold Hard Truth money books and O'Leary Funds/O'Shares: how he thinks about money ("I think of my money as soldiers"), diversification, discipline, and the rules he teaches relentlessly.
The story
Who Kevin actually is
Terrence Thomas Kevin O'Leary was born in Montreal in 1954. He earned a degree in environmental studies from the University of Waterloo and an MBA in entrepreneurship from the Ivey Business School at Western University — then went looking for a business to build.
In 1986, he co-founded SoftKey Software Products out of a basement in Toronto. Pursuing an aggressive consolidation strategy, SoftKey rolled up the educational-software industry, acquired The Learning Company in 1995, and took its name. In 1999, Mattel bought the company for roughly US$4.2 billion — the deal that made O'Leary's fortune and his reputation as a relentless dealmaker.
He became a household name as "Mr. Wonderful," the persona he developed on Canada's Dragons' Den (2006–2014) and carried to ABC's Shark Tank, where he's been a defining investor since 2009 across 16+ seasons. On screen and off, he's known for one thing above all: telling entrepreneurs the truth about their numbers.
Today Kevin is Chairman of O'Leary Ventures, his private venture-capital firm, and an active investor across dozens of companies. He founded O'Leary Funds (sold to Canoe Financial in 2015), co-founded the O'Shares ETFs, and built a consumer brand around "Chef Wonderful," including his own O'Leary Fine Wines. He's also a bestselling author — the Cold Hard Truth series on business, money, and life.
He remains squarely in the headlines: in 2024–2026 O'Leary advanced "Wonder Valley," among the largest proposed AI data-center campuses in North America (projects in Alberta and Utah), and in January 2025 he joined the People's Bid for TikTok, an effort to acquire and rebuild the platform's U.S. operations. Whatever the topic — money, markets, AI, or the next big deal — Kevin O'Leary brings a current, contrarian, headline-name perspective to the stage.
The receipts
Books & publications
Cold Hard Truth: On Business, Money & Life
2011The foundational, no-nonsense playbook on building wealth and running a business his way.
The Cold Hard Truth on Men, Women & Money
2012Money rules for every stage and relationship in life — blunt, practical personal finance.
Cold Hard Truth on Family, Kids & Money
2015Teaching financial literacy at home, across generations — money lessons for the whole family.
Cold Hard Truth on Marriage & Money
2015Money and partnership without the sentimentality — how couples can align on finances.
Digital Pivot or Bust in a Post-COVID-19 World
2020Adapting a business for the new digital economy — what permanently changed and how to respond.
The receipts
Companies & ventures
O'Leary Ventures
ChairmanHis private venture-capital firm — an active investor across dozens of companies.
O'Leary Funds
FounderInvestment-fund company founded in 2008; sold to Canoe Financial in 2015. Co-founder of the O'Shares ETFs.
O'Leary Fine Wines
Founder ("Chef Wonderful")His consumer wine brand — affordable wines from the Kevin O'Leary cellar under the Chef Wonderful banner.
Wonder Valley
Investor / O'Leary VenturesAmong the largest proposed AI data-center campuses in North America (Alberta and Utah projects, 2024–2026).
Gravity
Career highlights & recognition
- Milestone1999
Founded SoftKey / The Learning Company — ~$4.2B sale to Mattel
Co-founded SoftKey in 1986; rolled up the educational-software industry, acquired The Learning Company, and negotiated the ~$4.2B sale to Mattel in 1999.
- Milestone2009
"Mr. Wonderful" — defining Shark Tank investor since 2009
A defining investor on ABC's Shark Tank across 16+ seasons; the persona emerged on Canada's Dragons' Den (2006–2014).
- Credential
Chairman, O'Leary Ventures
Chairs his private venture-capital firm; founded O'Leary Funds (sold to Canoe Financial, 2015) and co-founded the O'Shares ETFs.
- Award
Bestselling author — the Cold Hard Truth series
Author of the Cold Hard Truth books on business, money, and life.
- Recognition
Headline AI-infrastructure investor — Wonder Valley
Advanced among the largest proposed AI data-center projects in North America (Alberta and Utah, 2024–2026).
Booking with confidence
What to expect when you book Kevin
- 01
Compiled from public sources
This profile is built from public, verifiable material and stamped with the date it was last reviewed. Nothing here is a claim we cannot trace to a source.
- 02
Availability and fees, confirmed
Tell us your date and brief, and we confirm Kevin's availability and current fee on request. We never publish a fabricated figure or imply an exclusivity we do not hold.
- 03
Managed end to end
From first inquiry to the day itself, Headliner handles briefing, contracting, and logistics, so your team can focus on the event.
Answers
Booking questions, answered
What is Kevin O'Leary's speaking fee?
Typically $100k–$200k (indicative; confirmed on request). Kevin's fee varies by event, date, format, and location, so we confirm the exact figure for your booking. Share your brief for current pricing and live availability.
Is Kevin O'Leary available for my event date?
Availability changes with Kevin's schedule and the season. Tell us your date and we'll confirm whether Kevin is open, and hold the slot while you decide.
What formats does Kevin offer?
Kevin is available for Keynote, Fireside chat, Moderation and Virtual engagements. We'll match the format to your audience and run-of-show.
What does Kevin speak about?
Kevin's keynote themes include Sales, Negotiation & Influence and Artificial Intelligence. Each talk is tailored to your audience and outcomes.
What languages does Kevin present in?
Kevin presents in English.
Where does Kevin travel from?
Kevin is based in West Palm Beach, FL and travels internationally for engagements; virtual sessions are also available.
Ready to book?
How to book Kevin — fees, availability & process
The fee context, real availability drivers, best-fit events, and the step-by-step booking process for Kevin.
Profile updated . Compiled from public sources — confirm current fees and availability with Headliner.
Book Kevin O'Leary through Headliner
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