Ep 132: Airtree Everywhere. Knockout Offer For Tanda

Aaron, Jack and Don are all back in the room and AirTree is everywhere this week: marking down Canva, warning its portfolio about AI disruption, fighting its own investors over a fund extension, and sitting on the Expert360 cap table as early backers get wiped out. Plus a stunning win for the bootstrap playbook as Thoma Bravo lobs a knockout offer for Tanda.

• Tanda's knockout offer: Thoma Bravo is the frontrunner to buy just under half of the 14-year-old bootstrapped Queensland HR and payroll player at about $800 million, well above the $500 million expected when Barrenjoey ran the auction, and why the four founders' bootstrap playbook and the rule of 80 got them there (AFR)
• AirTree reads the riot act: the fund warns its portfolio it will sell out of startups that cannot show they are safe from AI disruption, and tells threatened founders to strip cost and get to break even (AFR)
• Systems of record are in trouble: why a pure system of record with a human interface is exposed, how to become a system of agentic action before someone else does, and Aaron's story of replacing a subscription product with his own build in days
• AirTree v Canva stoush: the fight over extending the life of AirTree's first fund, Daniel Petre's angry email, and the existential question of whether Canva can keep winning free users against frontier AI products (AFR, and the resolution)
• Expert360 wipeout: Swipejobs buys Bridget Loudon's Expert360, a drag notice leaves only Series C and C1 preference holders with any consideration after $30 million-plus raised, and why founders must understand the pref stack (Capital Brief)
• Canva's leak hunt: Melanie Perkins' stern message to 5,000 staff, one Canvanaut sacked, and why a crisis should take no more than 10% of your time
• Tribe offsite: 24 founders at Spicers Hiddenvale, feedback of 'life-changing and business-changing', and three more planned for next year
• Themes of the week: playing to win versus playing not to lose, Jack's grand final black eye and nudie run, and 'whether you think you can or you think you can't, you're probably right'
• Sharts: the 1843 UK railway bubble, ChatGPT Work jumping from 6 to 20 million users in weeks, the AI homework study that lifted quality but tanked exam scores, illicit tobacco flipping the market, the Big Mac affordability index, and a Coke a day versus a pack of Marlboros compounded since 1986

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