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# Lessons from Jeremy Giffon
- URL: https://www.antoinebuteau.com/lessons-from-jeremy-giffon/
- Published: 2025-09-13T17:19:03.000Z
- Updated: 2026-07-22T00:42:00.000Z
- Description: Jeremy Giffon, an investor and former Tiny Capital general partner, brings a contrarian lens to business, deal-making, and life. His path from teenage technology work to philosophy study informs questions about judgment and investing.
- Author: Antoine Buteau
- Tags: Profile, Investing, Venture Capital Profiles

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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[2\]](https://themarketbyte.beehiiv.com/p/jgiffon?ref=antoinebuteau.com)

![Infographic for "Lessons from Jeffrey Giffon".](https://www.antoinebuteau.com/content/images/2026/07/lessons-from-jeffrey-giffon-optimized.webp)

### **On Investing and Deal-Making**

1. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
2. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
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. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
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. [\[5\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-replay?ref=antoinebuteau.com)[\[6\]](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com)
5. **"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. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
6. **"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. [\[7\]](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com)
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. [\[6\]](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com)[\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
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. [\[6\]](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com)[\[9\]](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000663067868&ref=antoinebuteau.com)
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. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
10. **"The big money is not in the buying and the selling, but in the waiting."** Echoing Charlie Munger, Giffon emphasizes a long-term perspective. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
11. **"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. [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
12. **"The most successful people respond the fastest."** He observes that successful individuals are effective "routers," quickly delegating tasks to the right people. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
13. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
14. **"Look for founders who have faced a major setback/tragedy in life."** He believes such experiences build mental toughness and resilience. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
15. **"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. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)[\[5\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-replay?ref=antoinebuteau.com)

### **On Business and Strategy**

1. **"The highest leverage business is being a trusted, true partner to people who control capital. That's it. That's the entire game."** [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
2. **"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. [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
3. **"Any organization driven on common agreement will be unable to act on the highest ambitious vision. Must be rule of one."** [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
4. **"The greatest good of capitalism comes from redirecting the energy of the ambitious away from zero-sum games."** [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
5. **"Twitter followings are under-rated."** As attention shifts to social media, those with distribution have increasing leverage. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
6. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
7. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
8. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
9. **"VCs and founders speak different languages."** This disconnect is a source of the "coordination problems" he seeks to solve. [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
10. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)

### **On Philosophy and Life**

1. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
2. **"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."** [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
3. **"It's an acute symptom of modernity... that we foolishly look to our jobs for meaning."** [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
4. **"Competition proceeds scarcity. Not the other way around. Things are scarce because first we desire them."** [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
5. **"A pretty much constant paradox is that we expect outlier outcomes from people that we demand act in normal, average ways."** [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
6. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
7. **"Nothing hurts ambition more than fear of conflict."** [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
8. **"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."** [\[2\]](https://themarketbyte.beehiiv.com/p/jgiffon?ref=antoinebuteau.com)
9. **"Read less, but better. Study the great books. Ignore basically everything else."** [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
10. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
11. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)[\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
12. **"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."** [\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)[\[11\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com)
13. **"The reward for good work is more work."** [\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
14. **"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."** [\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
15. **"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. [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
16. **"You can tweet your way onto a yacht."** A reflection on the power of social media to create opportunities. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
17. **"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. [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
18. **"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. [\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)[\[11\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com)
19. **"You don't need to be a genius to win in investing. You just need to see the game differently than everyone else."** [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
20. **"Most people wish that they like things that they don't actually like."** This internal conflict leads people to live inauthentic lives. [\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
21. **"It is important to have an explanation for why you think you can do better than everyone else when investing."** [\[11\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com)
22. **"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. [\[7\]](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com)
23. **"Start small, use your own money."** His advice for those wanting to get into acquisition entrepreneurship. [\[7\]](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com)
24. **"You have to be brutally realistic with yourself."** This applies to hiring, investing, and understanding your own preferences. [\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
25. **"The best opportunities aren't found, they're created."** [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)

### **Sources and Further Reading:**

- **Confluence.VC:** [25 Lessons From Jeremy Giffon (Managing Partner @ Tiny)](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com) [\[1\]](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)[\[10\]](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
- **Tim Denning's Blog:** [One of the Most Underrated Investors Shared the Best Ideas (Perhaps) That I've Ever Come Across](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com) [\[3\]](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
- **Invest Like the Best Podcast with Patrick O'Shaughnessy:**
  - [Apple Podcasts Episode](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000620745533&ref=antoinebuteau.com) [\[9\]](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000663067868&ref=antoinebuteau.com)[\[12\]](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000620745533&ref=antoinebuteau.com)
  - [PodPulse Notes](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com) [\[5\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-replay?ref=antoinebuteau.com)[\[11\]](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com)
  - [YouTube Upload](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com) [\[6\]](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com)[\[8\]](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
- **HoldCo Builders Podcast:** [30+ Acquisitions And Counting – The Hidden Genius of Jeremy Giffon](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com) [\[4\]](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
- **Spencer Kier's Podcast:** [Jeremy Giffon on Holding Companies, Incomplete Theses, Philosophy & Advice](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com) [\[7\]](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com)
- **The Market Byte (Beehiiv):** [The Most Interesting Thinker You've Never Heard Of](https://themarketbyte.beehiiv.com/p/jgiffon?ref=antoinebuteau.com) [\[2\]](https://themarketbyte.beehiiv.com/p/jgiffon?ref=antoinebuteau.com)
- **Jeremy Giffon's Substack:** [jeremygiffon.com](https://jeremygiffon.com/?ref=antoinebuteau.com) [\[13\]](https://jeremygiffon.com/?ref=antoinebuteau.com)

---

Learn more:

1. [25 Lessons From Jeremy Giffon (Managing Partner @ Tiny) - Confluence.VC](https://confluence.vc/jeremy-giffon-tiny/?ref=antoinebuteau.com)
2. [The Most Interesting Thinker You've Never Heard Of - Beehiiv](https://themarketbyte.beehiiv.com/p/jgiffon?ref=antoinebuteau.com)
3. [One of the Most Underrated Investors Shared the Best Ideas (Perhaps) That I've Ever Come Across | Tim Denning](https://timdenning.com/jeremy-giffon/?ref=antoinebuteau.com)
4. [30+ Acquisitions And Counting – The Hidden Genius of Jeremy Giffon - YouTube](https://www.youtube.com/watch?v=Kv9545KP5q4&ref=antoinebuteau.com)
5. [Jeremy Giffon - Special Situations in Private Markets - Invest Like the Best with Patrick O'Shaughnessy notes and takeaways - PodPulse](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-replay?ref=antoinebuteau.com)
6. [Jeremy Giffon Special Situations in Private Markets Invest Like the Best, EP 336 - YouTube](https://www.youtube.com/watch?v=2XtkpSdl6Z4&ref=antoinebuteau.com)
7. [Jeremy Giffon on Holding Companies, Incomplete Theses, Philosophy & Advice Ep.4Ep. 4Ep.4](https://www.youtube.com/watch?v=kSzmlQ01QFA&ref=antoinebuteau.com)
8. [Jeremy Giffon Special Situations in Private Markets Invest Like the Best, EP 336 - YouTube](https://m.youtube.com/watch?v=2XtkpSdl6Z4&t=1844s&ref=antoinebuteau.com)
9. [Jeremy Giffon - Special Situat… - Invest Like the Best with Patrick O'Shaughnessy](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000663067868&ref=antoinebuteau.com)
10. [25 Lessons from Jeremy Giffon (Managing Partner @ Tiny) - Confluence.VC Weekly](https://confluencevcweekly.beehiiv.com/p/jeremy-giffon-tiny?ref=antoinebuteau.com)
11. [Jeremy Giffon - Special Situations in Private Markets - EP.336 - Invest Like the Best with Patrick O'Shaughnessy notes and takeaways - PodPulse](https://podpulse.ai/podcast-notes-and-takeaways/invest-like-the-best-with-patrick-oshaughnessy-jeremy-giffon-special-situations-in-private-markets-invest-like-the-best-ep336?ref=antoinebuteau.com)
12. [Jeremy Giffon - Special Situat… - Invest Like the Best with Patrick O'Shaughnessy - Apple Podcasts](https://podcasts.apple.com/us/podcast/jeremy-giffon-special-situations-in-private-markets/id1154105909?i=1000620745533&ref=antoinebuteau.com)
13. [Jeremy Giffon | Substack](https://jeremygiffon.com/?ref=antoinebuteau.com)