Barry O'Reilly
@barryoreilly
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Entrepreneur | Advisor | Cofounder of Venture Studio @NobodyCrowd | Author #Unlearn #LeanEnterprise | Faculty @singularityu
San Francisco, CA
Joined June 2010
Huge congratulations to the @evalify.ai team for being featured in @incmagazine as one of the AI startups shaking up the LegalTech space. From day one, the team has been relentless about using AI to transform how intellectual property is understood, valued, and protected.
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Ever wonder why 95% of enterprises get zero ROI from AI? It’s not the tools or the models. It’s the system they’re dropped into. My new blog breaks down why AI adoption stalls, and what leaders must redesign for 2026. 🔗 https://t.co/cBYB6Jv9Kt
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AI Adoption in 2026 demands new workflows, decisions, and operating models. Learn how leaders build the conditions for successful AI adoption.
Last quarter I rolled out Microsoft Copilot to 4,000 employees. $30 per seat per month. $1.4 million annually. I called it "digital transformation." The board loved that phrase. They approved it in eleven minutes. No one asked what it would actually do. Including me. I
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A major divide is forming between companies that treat AI as a capability shift vs a tool. In 2026, that gap becomes impossible to ignore. Here’s what leading AI adoption in 2026 actually looks like: 🔗 https://t.co/cBYB6Jv9Kt
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Imagine if everything in life was as good as gold. It’s easy to invest in, could help grow your wealth, and protect it too. A timeless asset that stands strong when others may not.
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There’s no platform for the decisions that matter most. Strategy, tradeoffs, tough calls—most execs are still managing it all across disconnected tools. Steve Elliott shares why Dotwork was built to fix that. 🎧 Full episode here: https://t.co/mNoYsY1iZY
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You spend millions on enterprise software… Then your org changes, and it all breaks. So you go back to spreadsheets. Steve Elliott explains why dynamic companies kill static tools. 🎧 Listen now on the #UnlearnPodcast
https://t.co/mNoYsY1iZY
#enterprise #productstrategy
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Acquired five times. Built, scaled, sold—and had to adapt every time. Steve Elliott shares what it’s like to go from startup momentum to corporate reality… then back to building again. 🎧 Full episode on #Unlearn podcast: https://t.co/mNoYsY0Laq
#startups #leadership #ai
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After 5 exits—including AgileCraft—Steve Elliott could have stopped. Instead, he built Dotwork to help leaders act decisively with the right context at the right time. We talk strategy, unlearning, and agentic AI on this week’s #Unlearn Podcast. 🎧 https://t.co/mNoYsY1iZY
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AI doesn’t change the business unless it changes how decisions are made. Where in your work would better decision-making create the biggest impact right now — personal, team, or organization? 👉 Read the full blog here: https://t.co/UwPOCY7imz
#ai #leadership #unlearn
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#VibeCoding is redefining who gets to build software. No technical background needed. #AI does the heavy lifting. Join me & Steve Yegge on Dec 3 to dig into the origins, the movement, and the frameworks teams can use today. 📅 Dec 3 — 5:00 PM PST 🎥 https://t.co/9ndgDyf1MC
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When your old playbook stops working, leadership gets real. Tomorrow, I’m live with David Mitchell to share how he rebuilt trust, clarity, and momentum at @futurice, how you can do the same. 🕒 Dec 2, 9am GMT / 5pm Manila 🔗 https://t.co/PziAAGtWyb
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Why These Lessons Matter Now The leaders who thrive are leaders that transform—they’ll be the ones willing to let go, learn fast, and reinvent how they lead. 7 years in, Unlearn is a mindset for an era defined by accelerated change. And it will belong to those who practice it.
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7. Reinvention Is the Real Work of Leadership The world doesn’t care about your old expertise—it cares about your ability to adapt it.
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6. Continuous Learning Is a Leadership Advantage Unlearning isn’t something you do once. Leaders who build “always learning” muscle stay sharp and relevant when everyone else is losing pace.
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5. Your Environment Shapes Your Evolution People change best when their environment supports new behaviors. Leaders must design conditions—incentives, workflows, culture—that encourage teams to stretch their abilities.
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4. Discomfort Is a Signal, Not a Stop Sign The edge of your competence always feels awkward. That’s where growth happens.
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3. Small, Bold Bets Create Big Transformations Extraordinary results come from repeated cycles of making small bets, learning quickly, and compounding what works.
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2. Behaviors, Not Beliefs, Break the Bottlenecks Unlearning is ultimately about replacing outdated behaviors with new ones—innovation rewards action, experimentation, and iteration.
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1. Success Can Be a Trap What made you successful in the past can quietly become the biggest constraint on your future.
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A decade of learning. A decade ahead to prepare for. Seven years after Unlearn, the AI era makes its message even more urgent. I’m sharing the seven principles that still matter most 👇
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Turnarounds start with leadership, not decks or strategy docs. I’m sitting down with David Mitchell to unpack the early signals, tough calls, and first 90 days that got @futurice back on track. If you’re rebuilding momentum, this convo is for you. 🔗 https://t.co/PziAAGtoID
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