This week on Trading Places, hosts Dave McClure and Aman Verjee cover the latest tech news, including OpenAI's path to a trillion-dollar IPO, Big Tech's massive AI spending spree, and Tether's $500 billion valuation. Plus, we sit down with Rick Baker, Managing Partner at Blackbird Venture Capital, to discuss the incredible Canva story, secondary transactions, and building Australia's venture ecosystem from the ground up.
📰 THIS WEEK'S NEWS
🤖 OpenAI's IPO Plans
-Potential $1 trillion IPO target-Microsoft ownership restructure (49% → 27%)
-California AG blesses for-profit transition
-Sam Altman hints at revenue north of $100B
💰 Big Tech AI Spending
-Microsoft, Amazon, Alphabet, Meta spending $125B/quarter on AI infrastructure
-Meta raises $30B in corporate bonds
-Oracle raises $38B for data center expansion
-Power constraints emerging as key bottleneck
📈 Secondary Market Consolidation
-Morgan Stanley acquires EquityZen
-Goldman Sachs acquired Industry Ventures
-Signals expansion of secondary market opportunities
🚀 IPO & Funding News
-Navan's challenging IPO (down 20% on day one)
-Mer raises $350M Series C at $10B valuation (5x step-up)
-Securitize going public via SPAC at $1.2B valuation
🪙 Stablecoin Market
-Tether considering $500B valuation round
-Coinbase reportedly pursuing $2B acquisition of BVNK
-Stablecoin revenue growing 300M+ per quarter
🎙️ FEATURED GUEST: RICK BAKER, MANAGING PARTNER @ BLACKBIRD VENTURES
The Canva Story
-Rick shares the incredible journey of Blackbird's investment in Canva—from a $250K seed investment to a company now valued at $40B.
GP-Led Secondary Transactions
-Rick walks through Blackbird's 2019 secondary sale:
-Sold ~$120M (1/3 of Fund I) at 93% of NAV
-Returned 3.5x to LPs while maintaining 9.5x exposure
-Used Lazard to run a competitive process
-StepStone + Australian super fund won the bid
Managing Concentration Risk
Owned 15% of Canva at peak, now ~11%
-Balance between maximizing returns and managing risk
-LP perspectives range from "sell everything" to "hold forever"
-Strategic sales during primary rounds to unlock growth capital
Australian VC Ecosystem
-Superannuation system: 12% of salary mandated into pension funds
-$4T AUD pool of long-term capital
-Reset after GFC: Blackbird, Square Peg, Airtree, Main Sequence
-Circle of life: Atlassian/Canva alumni starting next wave
💎 VALUATION CORNER: TETHER @ $500 BILLION
-Deep Dive on Tether
-Aman analyzes whether the world's largest stablecoin issuer is worth a $500B valuation:
-$13B+ in annual profit (2x BlackRock's profitability)
-75% market share vs. Circle's 20%-36x P/E ratio vs. Circle at 240x
-Medium transparency, aggressive reserve policy-Regulatory uncertainty in U.S. market
🔑 KEY TIMESTAMPS
01:12 - [ tech & vc news ]
01:21 - OpenAI Restructuring | $1T IPO?
08:24 - Big Tech Hyperscalers' Earnings and $125 Billion in Quarterly AI Spending
10:47 - Why This AI Boom is Different
15:58 - Morgan Stanley Acquires EquityZen17:39 - Navan's Public Offering Performance
21:05 - Mercor Raises at a $10 Billion Valuation22:23 - Securitize Going Public via SPAC ($1.25B)
24:37 - Tether's $500B Valuation Rumor
28:05 - [ interview: blackbird vc / rick baker ]
28:49 - Rick Baker's Background and Founding the MLC Venture Program
35:56 - The Canva Story45:06 - The Australian Venture Capital Market
01:07:44 - How the Secondary Market Solves the Liquidity Problem
01:15:48 - [ valuation corner: tether]
01:13:30 - Tether's Aggressive vs. $CIRC’s Conservative Reserve Policy
01:16:32 - Calculating Tether's Valuation Based on P/E
01:24:00 - The Regulatory Uncertainty for Stablecoins
01:31:30 - Final Thoughts on Tether's $500B Valuation & Stablecoin Market