Lessons from Howard Marks

Howard Marks, co-founder of Oaktree Capital Management, is a value investor distinguished by his attention to risk, market cycles, and crowd psychology, offering a disciplined way to navigate the financial market’s recurring emotional extremes.

Lessons from Bill Ackman

Bill Ackman, founder and CEO of Pershing Square Capital Management, is an activist investor known for high-conviction bets and corporate change, with major wins and public battles sharpening his pursuit of businesses built for exceptional durability.

Lessons from Stewart Butterfield

Stewart Butterfield, the Canadian entrepreneur behind Flickr and Slack, applies a background in philosophy to communication, collaboration, and software at scale, grounding his work in empathy, craftsmanship, and technology’s capacity to augment human potential.

Lessons from Drew Houston

Drew Houston, co-founder and CEO of Dropbox, turned a personal frustration into a global cloud-storage utility, pairing continuous learning and “healthy paranoia” with a practical framework for entrepreneurship, product design, personal growth, and life’s finite days.

Lessons from Melanie Perkins

Melanie Perkins, co-founder and CEO of Canva, moved from teaching design in Perth to building a global platform, demonstrating how persistence, visionary thinking, and sustained attention to meaningful problems can turn an ambitious idea into widely used technology.

Daily Digest — 2026-03-28

AI autonomy is advancing through both larger models and better operating infrastructure, but real-world agency depends on scarce compute, trained tool orchestration, and payment systems that unite identity, authorization, and settlement rather than merely adding another wallet.

Lessons from Jessica Fain

Jessica Fain, a product leader at Webflow and former chief of staff to Slack’s CPO, studies the art of influence, arguing that this deeply human capacity becomes even more consequential in high-stakes organizations shaped by AI.

Lessons from Mitchell Green

Mitchell Green, founder and managing partner of Lead Edge Capital, applies a “Moneyball” approach to growth equity, using an extensive operator-LP network to uncover undervalued companies beyond the venture capital industry’s traditional geographic centers.

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