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This issue of WDODTW? is in partnership with Age and AI. Everyone covers AI at work. Age and AI covers AI at life. AI is quietly reshaping how we are growing up and growing old, from the classroom to care, and nobody handed you a guide. Age and AI is that guide: what is actually going on, what to ask before you trust it, and how to stay in charge of the decisions that matter most. In plain English, with no hype and no fear. Practical, human, and independent.
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OpenAI submitted its S-1. The real story arrived on Friday night.
OpenAI filed its S-1 this week, then spent the following days quietly conceding the more interesting ground to Anthropic. What happened at 5:21pm on Friday matters more than any of it.
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The GTM bets that shouldn't have worked, and did
One grew revenue 50x after half his team quit over the strategy. One brought in 50K signups in a single day with no paid budget. One generated 100M+ views from a stunt that took 50 hours to conceive. One asked every prospect to demo the product themselves instead of demoing it for them.
None of them followed the safe playbook. They treated GTM like an experiment, moved before they had proof, and made bets most founders would never get approved.
HubSpot for Startups documented all 6 stories in the free Bold Bets Playbook. The risks they took, why it was risky, and what it returned.
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