#174 with Andrew Wilkinson - How to Network with Billionaires, Andrew and Sam's Recent Investments, & A Better Investor Than Buffett

Episode Summary

Executive Summary: The episode mixes a promotional intro with a wide-ranging conversation with Andrew Wilkinson about capital allocation, buying undervalued businesses, networking, and small experimental ventures. Wilkinson explains how he acquires and grows assets like Girlboss and Medimap by spotting hidden value, building moats, and using lean teams. He also discusses crypto-enabled creator incentives, his charitable giving, and using relationships and room selection as a long-term business strategy.

Main Topics: Podcast promotion and listener growth (Priority: 4/5): The hosts open with a strong appeal for iTunes reviews, explaining that reviews improve chart ranking, audience growth, ad revenue, and the ability to reinvest in the show and tour live. Andrew Wilkinson’s acquisition strategy (Priority: 5/5): Wilkinson describes buying businesses with hidden value, especially assets that look messy on paper but can become profitable with a lean operating model and stronger monetization. Girlboss turnaround and media assets (Priority: 5/5): He explains buying Girlboss assets after its venture-backed structure became unsustainable, focusing on social followers, newsletter reach, and podcast distribution rather than the legacy cost base. Medimap as a network moat (Priority: 5/5): Wilkinson details how Medimap built dominant coverage of Canadian walk-in clinics by solving an operational pain point, creating a defensible local healthcare search and booking network. Crypto, creator incentives, and Braintrust (Priority: 4/5): He argues crypto could realign labor and capital by giving early users and contributors ownership-like upside, using Braintrust as a promising example. Small experimental ventures and lifestyle investing (Priority: 4/5): The discussion covers his sugar-free bakery idea, his interest in hobby businesses, and how personal curiosity and local impact can justify small investments even when upside is uncertain. Networking, access, and philanthropy (Priority: 5/5): Wilkinson outlines a deliberate networking strategy built on paid rooms, hosted events, and cold outreach, plus a charitable giving model that doubles community donations and supports causes selected by others.

Key Arguments: Hidden value can be unlocked by replacing a venture-style cost structure with a lean bootstrap model. Large audiences and distribution assets can be profitable even if the company has been mismanaged. The best businesses often come from owning a network or database that competitors cannot easily replicate. Crypto may create a new model where early users and contributors share in the upside they help build. Valuation matters less when investing in proven operators, but at high prices it is still dangerous to generalize from the winners. Networking is an asset that compounds over time if you consistently meet interesting people and place yourself in the right rooms. Small side projects can be both personally fulfilling and strategically useful as a way to stay engaged while waiting for better opportunities. Delegating email and automating screening rules is a practical way to reclaim time and reduce cognitive overhead.

Data Points: Metalab revenue: about $50 million - Described as the scale Andrew Wilkinson grew his design agency to before using profits for acquisitions. Metalab profit: about $20–30 million - Wilkinson said the agency was highly profitable relative to revenue. Girlboss social following: about 2 million followers - Used as part of the rationale for buying the business/assets. Girlboss email subscribers: about 250,000 - Wilkinson cited newsletter size as a monetizable base. Girlboss team size: 7–8 employees - Current lean operating structure after acquisition. Possible Girlboss monthly ad revenue: $40,000–$50,000 per month - Wilkinson’s base-case ad monetization estimate for the newsletter. Girlboss long-term revenue potential: $20–30 million per year - Host and guest speculated on upside if ads, events, and user revenue scale. Rolling fund size: $11 million - Wilkinson mentioned an AngelList rolling fund he raised quickly. Annual venture investing pace: $2–3 million per year - He described venture as a side hobby separate from control acquisitions. Braintrust/no-fee model: 0% platform fees - A key differentiator in his description of the crypto-powered freelance marketplace. Medimap clinic coverage: 86% of Canadian walk-in clinics - Wilkinson said the network reached dominant coverage over five years. Medimap traffic: 100k-ish visitors per month - A Similarweb-based estimate discussed during the conversation. Medimap referring domains: 750 - Podcast host looked at backlink metrics to assess SEO moat. Medimap backlinks: 7,100 - Discussed as a sign of SEO strength and authority. Bakery startup cost: $5,000–$10,000+ - Wilkinson estimated the launch cost for his sugar-free bakery experiment. Charity donations enabled by AMA: $58,000 - Total donations generated through his ask-me-anything model, doubled with matching. Personal charitable giving: $3–4 million - Wilkinson estimated total lifetime giving so far. Pershing Square investment: $5 million invested - He bought into Bill Ackman’s holding company as a value play and networking opportunity. Pershing Square return: about 3x - Wilkinson said the investment grew from roughly $5 million to about $15 million over several years. Ted Conference spend: about $30,000 across 3 years - He described paying to be in high-value rooms as a networking strategy.

Pivotal Quotes: "We like to buy airport businesses." — Andrew Wilkinson: His analogy for businesses with captive audiences and multiple monetization opportunities while customers wait or pass through a network. "If you see something and you get lit up about it, ignore the valuation and just invest." — Andrew Wilkinson: Wilkinson’s advice on backing standout founders or ideas even when the price looks high. "The best way to be able to do what I want is by having enough opportunities that I'm not worried about saying no." — Andrew Wilkinson: Paraphrased sentiment expressed during his discussion of networking, optionality, and delegation.

Implications: Listeners should see how distribution, network effects, and founder quality can outweigh ugly financials. The episode suggests future winners may come from asset-heavy, platform-like businesses and crypto-aligned creator tools, not just classic VC startups.