Andrew Wilkinson

Co-founder of Tiny, a holding company that buys and invests in internet businesses.

Mentions

Appeared in

Discussed in

Key positions and views

Prefers acquiring profitable, "boring" businesses with strong competitive moats (e.g., high switching costs, network effects) over high-growth, venture-backed startups. [46, 20, 25, 56]

Believes AI, specifically LLMs, will commoditize many SaaS businesses by drastically increasing competition and compressing profit margins. [22, 37]

Advocates for a "permanent capital" investment structure, similar to Berkshire Hathaway, which provides stability and avoids investor redemptions. [9]

Views most popular entrepreneurial paths like freelancing, content creation, restaurants, and angel investing as fundamentally flawed or high-risk models with low ceilings. [1, 2, 6, 7]

Employs a decisive and swift management philosophy, such as firing an employee immediately upon the first thought of doing so. [13]

Podcast consensus on Wilkinson

Points of consensus

▶Andrew Wilkinson co-founded and leads Tiny, a holding company that acquires profitable internet businesses and is often compared to a "Berkshire Hathaway of the Internet." [18, 5, 16, 40]Apr 2026

▶He prioritizes acquiring businesses with strong, durable competitive moats, such as the network effects of Letterboxd or the high switching costs associated with Serato's hardware integration. [20, 25, 56]Apr 2026

▶He is a strong proponent of using AI for personal productivity, building custom agents for tasks like email management, meeting preparation, and coding. [41, 44, 45, 47, 52]

▶He believes that AI, particularly LLMs, will fundamentally disrupt the SaaS industry by drastically increasing competition and compressing profit margins. [22, 37]Apr 2026

Points of debate

▶Wilkinson ranks the agency model as a low "C" tier due to its "feast or famine" nature, yet his own agency, Metalab, has been a massive success, generating "hundreds of millions of dollars in profit." [4, 27]Apr 2026

▶He advocates for entrepreneurs to pursue "boring," uncompetitive niches, but Tiny's recent high-profile acquisitions include culturally significant tech companies like Letterboxd and Serato. [46, 20, 58]

▶He ranks SaaS as a "B" tier model and is highly skeptical of its future due to AI, leading Tiny to reject most SaaS deals, yet a significant portion of Tiny's portfolio and revenue is derived from software companies. [12, 37, 32]Apr 2026

▶He dismisses angel investing as an "E" tier activity akin to "roulette" for most people, yet his core business involves acquiring and investing in companies, albeit with a different model focused on profitability and control. [7, 5, 14, 20]Apr 2026

Key themes

▶The 'Wonderful, Boring' Business PhilosophyApr 2026

Wilkinson champions acquiring profitable, often overlooked businesses with strong competitive moats, contrasting sharply with the venture capital model of chasing high-growth, high-burn startups. He explicitly seeks out uncompetitive niches and values stability and cash flow over rapid scaling. [46, 56]

This 'anti-VC' approach suggests a growing market for founders who want an exit without the pressures of hyper-growth, making Tiny a key player in the alternative funding landscape for profitable, sustainable businesses.

▶Business Model Tier-Ranking FrameworkApr 2026

Wilkinson systematically categorizes business models into tiers (S-F), providing a clear framework for his investment decisions. He ranks permanent capital vehicles as "S" tier while dismissing models like restaurants ("E"), MLMs ("F"), and freelancing ("D") due to issues with scalability, margins, and operational complexity. [9, 6, 11, 1]

This framework reveals a highly analytical and risk-averse approach to business, prioritizing structural advantages over founder charisma or market hype, which is a valuable lens for evaluating potential investments.

▶Pragmatic AI Adoption and Strategic Skepticism

Wilkinson is both an avid user and a cautious observer of AI. He personally leverages AI agents for productivity (email, calendar, coding) but predicts AI will cause massive margin compression in the SaaS industry, leading Tiny to reject most SaaS acquisitions. [41, 45, 47, 22, 37]

His dual perspective as a power user and a skeptical investor highlights the immediate productivity gains of AI versus the long-term strategic risks it poses to established software business models.

▶Entrepreneurial Realism and Personal Well-beingApr 2026

Wilkinson openly discusses his significant failures, including losing $10 million on his startup Flow, and the disconnect between immense wealth and personal happiness. He also speaks candidly about his ADHD diagnosis and the positive impact of SSRIs, grounding his business advice in personal experience. [19, 15, 48, 50]

This transparency demystifies the 'overnight success' narrative, offering a more realistic model of entrepreneurship that prioritizes sustainability and personal well-being over relentless, often destructive, growth.

Source episodes

Sentiment over time

Not enough data for timeline

Changes over time

Early Career

Founded and failed at multiple ventures, including a pizzeria, designer cat furniture, an online DJ school, and a skin cream business, resulting in losing all his money. [17]

2008-2015

Gained a strong reputation through his design agency, Metalab, which designed the first version of Slack and became highly profitable, generating hundreds of millions in profit over its lifetime. [24, 27]

Post-Metalab Success

Co-founded the holding company Tiny with Chris Sparling with an initial capitalization of $4-5 million, which has not required further investment. [5]

Unspecified (Pre-Tiny)

Lost $10 million of his own money trying to bootstrap the project management startup Flow while competing against the venture-backed Asana. [19]

2022-2024

Tiny has become increasingly cautious about SaaS acquisitions due to the perceived threat of AI-driven competition, rejecting nearly all opportunities in the sector. [37]

Recent Acquisitions

Tiny acquired several well-known brands, including AeroPress, Letterboxd, and Serato, the world's largest DJ software company. [14, 20, 58]

Suggested prompts

How does Andrew Wilkinson reconcile his "C" tier rating for agency businesses with the immense success of his own agency, Metalab? &nearr;What specific criteria does Tiny use to evaluate a "boring" business's moat, and how does this apply to recent tech-focused acquisitions like Letterboxd? &nearr;Given his prediction of AI-driven margin compression in SaaS, what is Tiny's long-term strategy for its existing software portfolio? &nearr;How has Wilkinson's personal experience with business failure and mental health challenges shaped Tiny's hands-off, post-acquisition management policy? &nearr;

Key concepts

Tiny (Holding Company) 2 ep Business Models 2 ep Artificial Intelligence 2 ep Investment Strategy 2 ep SaaS Industry 2 ep Entrepreneurship 2 ep Competitive Moats 2 ep Serato 2 ep Personal Productivity 1 ep Mental Health & ADHD 1 ep

Notable quotes

“I ended up losing $10 million trying to compete with venture-backed businesses and bootstrapping. It was all my own money, poured $10 million, lit it on fire, trying to compete with Asana because I didn't understand how the business world worked really.”

Andrew Wilkinson · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

“I just think LLMs increasingly can build software. And it's not that it's going to put all these businesses. Let's say you have a SaaS software company and there's 10 competitors five years ago. I just think there's going to be 50 or 100 competitors in the future. And when that happens, competition equals margin compression.”

Andrew Wilkinson · I Own 38 Businesses. Here's What Actually Makes Money.

“I think that is kind of the iPhone moment that we're going to have in some time in the next five years.”

Andrew Wilkinson · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

“the kind of heuristic I have is if I ever think, should I fire this person, even once, I should fire them immediately.”

Andrew Wilkinson · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

Report last updated: Apr 21, 2026

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