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UpHealth tried to connect care. Then came the unbundling.
A bedside interpreter made the promise of connected healthcare tangible. UpHealth’s costly retreat shows how far a useful product can travel from the company built around it.
Harish Chidambaran and the distance between a bell and a balance sheet
He spent fourteen years taking iLearningEngines from a private venture to Nasdaq. Within months, the company was in bankruptcy; in 2026, its founder faced federal fraud charges that remain allegations.
AvePoint Spent 25 Years Guarding Your Files. Now It Wants to Guard Your AI.
Two engineers coded their first product in a public library. A SPAC deal, $419 million in revenue and 28,000 customers later, AvePoint is wagering that the next great data problem is the AI you just turned on.
Yellow.ai Is Going Public To Buy The Call Centers It Wants To Replace
The Bangalore-born, San Mateo-based agentic AI company is merging with Bluerock Acquisition Corp in a deal valuing it near $550 million - then spending the proceeds on the human-run BPO firms its software is designed to automate.
Tre Sayle
Robert 'Tre' Sayle is a Partner at Thoma Bravo, one of the world's largest software-focused private equity firms, where he has spent nearly two decades building the Growth platform - a minority equity investing practice targeting breakout software companies. He orchestrated roughly 22 deals worth ~$50 billion in transaction value, led the $1B Thoma Bravo Advantage SPAC as CEO through its $11.1B merger with IronSource, and was named one of GrowthCap's Top 25 Software Investors of 2021. A Harvard economics graduate who started his career in tech investment banking at Hambrecht & Quist and JPMorgan, Sayle is known for his patience, his preference for informal first meetings over stiff boardrooms, and a global outlook that includes aggressive investment in Israeli cybersecurity.
Shervin Pishevar
Shervin Pishevar is an Iranian-American entrepreneur, venture capitalist, and super angel investor known for early-stage investments in Uber, Airbnb, and over 200 startups. A former managing director at Menlo Ventures and co-founder of Sherpa Capital, he has achieved 93 exits in his 27-year tech career and averaged 73x returns on investments. Co-founder and former executive chairman of Hyperloop One, Pishevar championed Elon Musk's vision for high-speed transportation. Currently, he runs the Edison Fund and serves as chairman of Telly, continuing to shape the future of technology and innovation. His journey from an immigrant family that arrived with $35 to becoming a Forbes Midas List investor for four consecutive years exemplifies the American Dream.
Vishal Garg
Vishal Garg is the Indian-American founder and CEO of Better.com, the online mortgage broker that went public via SPAC in 2023. A serial entrepreneur since his early twenties, he previously co-founded MyRichUncle, which became the second-largest private student lender in the U.S. before collapsing in the 2008 financial crisis. Known for his blunt communication style - including the infamous 2021 Zoom firing of 900 employees - Garg has built multiple companies at the intersection of finance and technology while living in Manhattan with his wife and three children.
Chamath Palihapitiya
Chamath Palihapitiya is a Sri Lankan-Canadian-American venture capitalist, founder of Social Capital, and co-host of the All-In Podcast. A former VP of User Growth at Facebook who helped scale the platform from 50M to 700M+ users, he left to build one of Silicon Valley's most distinctive investment firms. Known for contrarian takes, a welfare-to-billionaire origin story, and pioneering the 'growth hacking' playbook, he now manages $2.147B in AUM while running a top-ranked Substack newsletter and co-hosting one of tech's most listened-to podcasts.
Jack Raines
Jack Raines is a writer, investor, and author who turned a $150,000 trading loss into a media career and a Penguin Random House book deal. He writes Young Money, a newsletter with 61,000+ subscribers covering behavioral finance, career philosophy, and what your twenties are actually for. He's now an investment associate at Slow Ventures, where he works on their $63M Creator Fund. Known for viral LinkedIn satire that got him reported to Columbia Business School as the 'Bacon Bandit of Hell's Kitchen,' he combines intellectual rigor with a refusal to take himself too seriously.