Episode Summary
Executive Summary: Andrew Wilkinson, founder of MetaLab and Tiny, discusses his journey from a design agency to building a holding company of 30+ businesses. He shares lessons from missed opportunities like Slack equity, his founder-friendly acquisition strategy inspired by Warren Buffett, and insights on managing diverse businesses. Topics include the WeCommerce IPO, buying Girlboss, and the challenges of being copied by big tech.
Main Topics: MetaLab's Role in Slack's Design (Priority: 5/5): Andrew clarifies MetaLab's contribution to Slack—designing the original logo, color palette, UX, web app, and mobile app for $80K. He addresses a Twitter controversy where he was accused of overstating his role, explaining it was a typo. Tiny's Acquisition Philosophy (Priority: 5/5): Andrew explains Tiny's approach to buying businesses: founder-friendly, fast (30-day close), no price changes, and minimal interference. Inspired by Berkshire Hathaway, they leave management alone unless self-immolation occurs. WeCommerce IPO and Shopify Ecosystem (Priority: 4/5): WeCommerce, a Tiny SPAC-alike RTO in Canada, went public at ~$1B CAD valuation on ~$20M revenue run rate. It buys Shopify ecosystem businesses, leveraging the platform's growth. Girlboss Acquisition and Turnaround (Priority: 4/5): Andrew describes buying Girlboss from Attention Capital at a distressed price, pivoting it from a venture-scale social network to a media business focused on newsletters, podcasts, and job boards. Big Tech Copying and Clubhouse's Future (Priority: 3/5): Andrew discusses how Twitter, Facebook, etc., copy innovations like Clubhouse, arguing it's a feature vs. product problem. He sees Twitter as underpriced and ripe for monetization via paid newsletters, analytics, and audio. Crypto's Lack of Real-World Revenue (Priority: 3/5): Andrew remains skeptical of crypto beyond speculation, noting no at-scale non-speculative use case has emerged in 8+ years. He compares it to the dot-com boom where Amazon had real revenue. Munger's Heuristics Applied (Priority: 2/5): Andrew applies Charlie Munger's 'fish where the fish are' (find quiet niches) and inversion (think about what can go wrong) to avoid misery and make better decisions.
Key Arguments: Missed Slack equity was a huge missed opportunity—$80K cash vs. potentially $75M in equity, justifying Andrew's shift to taking equity in some deals. Tiny's acquisition model works because it prioritizes founder experience (fast close, no price changes, operational independence), attracting quality businesses. Buying businesses with strong product-market fit and focusing on base hits (operational improvements) is safer than chasing venture-scale moonshots. Ad-based businesses are riskier than subscriptions due to volatile CPM rates and headcount-intensive sales; frictionless, self-serve transactions are preferred. Twitter is undermonetized and can build 20-30 new products (paid newsletters, audio, analytics) to capture value from its captive audience. Crypto has not yet delivered a non-speculative business at scale, making it a wait-and-see area despite its theoretical promise. Amazon's Shopify-like acquisition (Sell) will struggle because independent retailers distrust Amazon's data use and direct competition. Applying Buffett/Munger principles—like inversion and avoiding crowded 'fishing holes'—gives Tiny a high probability of success in lower-risk niches.
Data Points: Number of businesses owned by Tiny: ~30 - As of the interview, with ~700 employees. Slack design fee: $80,000 - MetaLab's fee for designing Slack's original brand, UX, web app, and mobile app. Potential equity value if taken: $75,000,000 - If Andrew had taken half the Slack fee in equity, based on Slack's eventual $27B valuation. Dribbble revenue growth: 10-12x - Since acquisition by Tiny, from single-digit millions to tens of millions in revenue. WeCommerce valuation at IPO: ~$1,000,000,000 CAD - Market cap upon going public via reverse takeover in Canada. WeCommerce revenue run rate at IPO: ~$20,000,000 - Annualized revenue when WeCommerce went public. Inbound acquisition inquiries per month: ~50 - Tiny receives about 50 inbound deal inquiries monthly. Deal closing frequency: 1 every 3-4 months - Tiny's typical deal cadence. Girlboss acquisition price context: Distressed - Bought from Attention Capital after venture-funded social network failed. Morning Brew acquisition price: $75,000,000 - Reported sale price, cited by Andrew as an example of a newsletter business. Morning Brew revenue: $10,000,000+ - Estimated ad revenue before acquisition. The Hustle acquisition price: ~$30,000,000 - Approximate sale to HubSpot, including Trends.co.
Pivotal Quotes: "We do quote unquote the mobile app. They came to us for design. We did the mobile app and web app. And I just typoed. I wasn't trying to ever imply that we did the development. We didn't even do the development back then. We didn't do dev work." — Andrew Wilkinson: Andrew explains the Twitter controversy with Johnny Rogers, where he was accused of overstating MetaLab's role in Slack. "Charlie Munger likes to say, fish where the fish are... Munger advocates finding a quiet fishing hole off the beaten path with two old fishermen and a couple fish." — Andrew Wilkinson: Andrew applies this heuristic to Tiny's acquisition strategy of avoiding crowded, competitive spaces. "I want to see someone do real revenue. And I don't know why that hasn't happened. When I talk to smart developers, they often say, Yeah, it's called a database. We've had these for a long time." — Andrew Wilkinson: Andrew's skepticism about crypto's lack of non-speculative, real-world revenue generation after 8+ years.
Implications: Founders should prioritize building product-market fit before seeking scale, consider founder-friendly acquirers like Tiny for exits, and be wary of ad-based business models. Twitter's potential monetization of newsletters and analytics could reshape creator economics. Crypto remains high-risk until a sustainable non-speculative use case emerges.
About This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.