Lessons from Jeffrey Giffon

A compilation of insights from investor Jeremy Giffon, former general partner at Tiny Capital, reveals a distinct and often contrarian approach to business, investing, and life. Giffon, who began his career in the tech industry as a teenager and later studied philosophy at Columbia University, has shared his learnings through various podcasts and writings, influencing a new generation of thinkers in the investment world. [1][2]

On Investing and Deal-Making

"The best deals slap you in the face." Giffon believes the most promising investment opportunities are immediately obvious and don't require extensive debate or complex justification. [3]
"Napkin math beats spreadsheets." He advocates for simple, high-level financial analysis focusing on profitability and realistic growth, rather than getting lost in overly detailed spreadsheets. [3]
"If it's not a screaming 'yes,' it's a no." This principle, similar to Derek Sivers' "Hell Yes or No" framework, is central to Giffon's decision-making in investments. [4]
"The perfect investment would be one where you actually never have to talk to any of the people or know anything about the business." Instead, one can simply understand the surrounding circumstances and incentives. [5][6]
"The best assets in the world are unloved, orphaned, and misunderstood." He finds value in "ghost ship" companies—businesses that are fundamentally sound but neglected by their investors. [4]
"You should do one deal, and every deal you do should be like the last deal." At Tiny, each acquisition was treated as if it were their last, ensuring a high bar for quality. [7]
"I don't want to be part of any club that'll have me as a member." Giffon applies this Groucho Marx quote to investing, questioning why a seemingly great deal has come his way. [6][8]
"Coordination problems are where the money is." He focuses on identifying and solving misaligned incentives between parties, such as founders and VCs, to unlock value. [6][9]
"If you're doing deals just to stay busy, you're going to underperform someone who waits for the fat pitch." Patience is a critical, though difficult, virtue in investing. [4]
"The big money is not in the buying and the selling, but in the waiting." Echoing Charlie Munger, Giffon emphasizes a long-term perspective. [4]
"After you have a convo, do you both leave feeling energized or drained? We've never regretted hiring someone we look forward to talking to but have made many mistakes hiring otherwise great people we did not." This is his single most important question when hiring CEOs. [10]
"The most successful people respond the fastest." He observes that successful individuals are effective "routers," quickly delegating tasks to the right people. [3]
"Trustworthiness is paramount." Giffon is vigilant for small "white lies" from founders and will walk away from a deal, no matter how good it seems, if he detects dishonesty. [3]
"Look for founders who have faced a major setback/tragedy in life." He believes such experiences build mental toughness and resilience. [3]
"The perfect business is one where you get paid an absurd amount of money for your words alone." He points to old-school merchant banks as an example of a business model based on wisdom and reputation. [4][5]

On Business and Strategy

"The highest leverage business is being a trusted, true partner to people who control capital. That's it. That's the entire game." [4]
"When people set out to build a company they either want the satisfaction of building a well-run machine that they can walk away from or they want to build scaffolding around them that lets them do more of what they like." He notes these two motivations are quite different but often get grouped together. [10]
"Any organization driven on common agreement will be unable to act on the highest ambitious vision. Must be rule of one." [10]
"The greatest good of capitalism comes from redirecting the energy of the ambitious away from zero-sum games." [10]
"Twitter followings are under-rated." As attention shifts to social media, those with distribution have increasing leverage. [1]
"One big idea is all you need. Great entrepreneurs repeat themselves without losing intensity or passion." He cites Jeff Bezos's relentless focus on the customer as an example. [1]
"The best business is one where you're getting paid for your thoughts." This not only generates revenue but also leads to meeting interesting people and compounding knowledge. [1][10]
"Time in the market is a dangerous idea for high agency individuals." For those who are money-oriented, he suggests that building something can outpace stock market returns in the first decade. [1][10]
"VCs and founders speak different languages." This disconnect is a source of the "coordination problems" he seeks to solve. [4]
"In the future, there will be co-founders who are Chief Audience Builders." Their role will be to leverage their audience for the benefit of a complementary startup. [3]

On Philosophy and Life

"I don't believe there is such a thing as laziness. Rather, I believe that most people spend their lives working on the wrong thing." Everyone has something they can do effortlessly for hours. [1][10]
"If you want to do something well, do it every day. And if you don't want to do it every day, you won't be able to do it well." [1][10]
"It's an acute symptom of modernity... that we foolishly look to our jobs for meaning." [1]
"Competition proceeds scarcity. Not the other way around. Things are scarce because first we desire them." [1]
"A pretty much constant paradox is that we expect outlier outcomes from people that we demand act in normal, average ways." [1]
"The Romans had the right idea that there ought to be distinct stages for distinct ages." He describes a life path of proving oneself, public service, and then elder statesmanship. [1]
"Nothing hurts ambition more than fear of conflict." [10]
"If you spend 6 months really trying to understand how you want to spend the rest of your life, that's 6 months well spent." [2]
"Read less, but better. Study the great books. Ignore basically everything else." [1]
"Discover God's calling for you." Instead of the paralysis that can come from being told you can do anything, he suggests listening for a specific purpose. [1]
"If you envy others, it's a sign you haven't found your calling." He uses the analogy of a quarterback who is focused on their own role and doesn't envy others on the field. [3][4]
"People often spend their life doing things they don't like because they don't know what they truly want or are scared of the consequences of acting like someone who doesn't." [8][11]
"The reward for good work is more work." [8]
"Basically three categories of colleges worth going to: top ten (to join ruling class), big state school frat/athletics (for peak life experience), weirdo lib arts colleges... (to actually become erudite). Highly suspicious of everything else." [10]
"Sage advice I got in a boxing gym once: there are guys in here whose survival hinges on winning the fight and there's everyone else. It's prudent to know which one you're competing with." He believes this applies to everything in life. [1]
"You can tweet your way onto a yacht." A reflection on the power of social media to create opportunities. [3]
"Pay $57,000 to have lunch with your hero." He references the story of one of Tiny's founders paying for a lunch with Bill Ackman, which led to Ackman becoming a major investor. This illustrates the value of bold, direct access to influential people. [3]
"Good investments should energize you and get you excited." If an investment drains you, it's not the right fit, regardless of its apparent quality. [8][11]
"You don't need to be a genius to win in investing. You just need to see the game differently than everyone else." [4]
"Most people wish that they like things that they don't actually like." This internal conflict leads people to live inauthentic lives. [8]
"It is important to have an explanation for why you think you can do better than everyone else when investing." [11]
"If it's just too hard, you don't need to do anything." He emphasizes that no one is forcing you to make an investment, and it's okay to pass on deals that are too complex. [7]
"Start small, use your own money." His advice for those wanting to get into acquisition entrepreneurship. [7]
"You have to be brutally realistic with yourself." This applies to hiring, investing, and understanding your own preferences. [8]
"The best opportunities aren't found, they're created." [4]

Sources and Further Reading:

Confluence.VC: 25 Lessons From Jeremy Giffon (Managing Partner @ Tiny) [1][10]
Tim Denning's Blog: One of the Most Underrated Investors Shared the Best Ideas (Perhaps) That I've Ever Come Across [3]
Invest Like the Best Podcast with Patrick O'Shaughnessy:
HoldCo Builders Podcast: 30+ Acquisitions And Counting – The Hidden Genius of Jeremy Giffon [4]
Spencer Kier's Podcast: Jeremy Giffon on Holding Companies, Incomplete Theses, Philosophy & Advice [7]
The Market Byte (Beehiiv): The Most Interesting Thinker You've Never Heard Of [2]
Jeremy Giffon's Substack: jeremygiffon.com [13]

Learn more:

Lessons from Jeffrey Giffon

On Investing and Deal-Making

On Business and Strategy

On Philosophy and Life

Sources and Further Reading:

Written by Antoine Buteau

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