Ep 131: Canva Val Slash. Market Places Are In Trouble. Sophii AI. Agentic Outcomes. Venture Debt Rules & Thumb. Sharts.

Aaron is off sick, so Don and Jack unpack a big week in venture, AI and building companies.

• Canva marked down at every level: Blackbird and AirTree cut their carrying value 17% ($42B to $34B) while 20VC's Jason Lemkin pegs it closer to $12 billion after growth guidance fell from 30% to 20%, why no AI agent recommends the Canva API, and Don's case that a founder-led company with $1.5B in cash can still reinvent from within.
• Should I sell or should I stay: the checklist Don gave a portfolio board (AI talent, proprietary data, strategic functionality, can you thrive as the API, capital availability, energy and passion, risk versus reward), and Jack's advice to meet M&A advisors early and take some money off the table.
• Marketplaces are in trouble: Google's Have AI Get Prices agent now phones local businesses directly, why companies will need return-fire agents, and the cyber boom that follows.
• Sophii AI raises $30M: the Gold Coast startup building an AI receptionist for tradies at a tenth of a wage, with a free job-management platform as the Trojan horse for context. Don holds a small angel investment.
• Pay only on outcomes: Sierra charging $1.50 per resolved case, free if it escalates to a human, on its way to $200M ARR, and what outcome-based pricing means for how software gets bought.
• Agents becoming goal-seeking geniuses: the gym waitlist agent that read the booking API, found a vulnerability and deleted a stranger's reservation, arguably Australia's first autonomous AI cyberattack.
• What moron would sign up for this: Harry Stebbings' new growth bar ($1M to $4M to $12M to $30M to $75M) versus Adam Robinson's bootstrap rebuttal, and why many founders don't need venture money in this new world.
• Venture debt rules of thumb from Tractor Ventures' Jodi Imam: borrow 1 to 3x monthly revenue, six-month deployment window, model against a bad quarter, and count the cost in dollars. Plus Advanced for accessing R&D funding mid cycle.
• Sharts: Palantir's rule of 40 score hits 155%, Mailchimp revenue now falling after its $12B acquisition, agents overtake humans on OpenRouter token usage, and roughly 72% of vested startup options never get exercised.

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