25 Lessons from Jeremy Giffon (Managing Partner @ Tiny)

Jeremy Giffon (@jeremygiffon) is the managing partner at Tiny


Like many other investors we have studied, he is reserved with his words, but when he speaks we listen. If you’re looking for regurgitated investor lessons, you won’t find them from him.


Here are 25 takeaways from studying Jeremy, his career, and his investment philosophy.

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Jeremy Giffon (Tiny)


  • Read less, but better. Study the great books. Ignore basically everything else.


  • Good ideas are easy to justify. The best deals smack you in the face. His best deals got everybody excited in a few sentences while the worst ones came from multi-week debates and “rigorous” thinking.


  • Discover God’s calling for you. We tell kids they be anybody and do anything if only they set their minds to it. There are multiple problems with this. It’s not true and the possibility of doing anything can lead to paralysis. What if you did the opposite, and listened to God’s calling for you? Assume you don’t have agency. A master planner has designed you for a specific purpose at a specific time.


  • Twitter followings are under-rated. The more attention shifts from mainstream media to social media, the more leverage goes to people with distribution.


  • One big Idea is all you need. Great entrepreneurs repeat themselves without losing intensity or passion. How many thousands of times has Jeff Bezos told his team to focus on the customer?


  • The best business is one where you’re getting paid for your thoughts. Getting paid for your thoughts has the added benefits of getting to meet super interesting people, gaining exposure through investments, and your learnings and experience compound quickly. Success in this arena is mostly brand/reputation building.


  • Look for opportunities where the incentives are in your favor. All diligence should center around understanding the stakeholder incentives and why the deal fell in your lap.


  • Understand your edge. If you don’t know what you bring that makes you better than the next guy, how can you compete with the guys that do know?


  • Keep it simple (but not simplistic). Napkin math > spreadsheet math.


  • Spend more time thinking about how to spend your time. Most of us go through life putting up with the things we do. We do this because we don’t really know what it is we want, and we haven’t taken the time to seriously think about it. Six months really trying to understand how you want to spend the rest of your life is six months well spent.


  • Quarterbacks envy nobody. The ability to witness other’s success and feel joy (or nothing) rather than envy, is a good indication that you’re in a healthy space. Undermining others accomplishments comes from a place of insecurity.


"After hiring tons of CEOs there’s only one question that really matters. 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."

"Long periods of low effort work w/ nebulous goals and no defined end -> much progress, little results -> dissatisfaction -> more low effort work -> repeat vs Short periods of intense work w/ bounded & defined outcomes -> results -> satisfaction -> rest -> inspiration -> repeat"

"Nothing hurts ambition more than fear of conflict. Ambition must be lowered until we can arrive at a vision we “all can agree on” which isn’t a vision at all. Any organization driven on common agreement will be unable to act on the highest ambitious vision. Must be rule of one."

"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, eg Deep Springs, St John’s, etc (to actually become erudite). Highly suspicious of everything else."

"If you want to do something well, do it everyday. And if you don’t want to do it everyday, you won’t be able to do it well."

"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. These are pretty divergent but they get lumped together."

"The greatest good of capitalism comes from redirecting the energy of the ambitious away from zero-sum games."

"If you’re at all money oriented, you can more than easily outrun the first decade of stock market compounding by using your capital to build something. Time in the market is a dangerous idea for high agency individuals."

"The Romans had the right idea that there ought to be distinct stages for distinct ages. Young men go to Gaul to prove themselves and get rich, then serve their people in public life, and finally serve the youth via writing, oration and elder statesmanship broadly. Accumulating dignitas in each stage, but never getting caught in gluttonous obsession with any one notion of power, influence or wealth. To be focused on money in old age was gauche and to try and teach before you had earned your station lacked integrity. It provides a purpose and value for every stage of life and matches up with the natural rhythms of aging. Adolescent vitality funneled into conquest and bravery, the weight of fatherhood and family to shepherding the well-being for the people, and the experience of old age to sharing the wisdom that shapes and refines the way younger men go about the first two pursuits."

"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. No one is a lazy procrastinator in all areas of life. Everyone has something they can do effortlessly for hours. And they tend to do that effortless thing better than they do the thing they are lazy about."

"Sage advice I got in a boxing gym once: there are guys in here who’s survival hinges on wining the fight and there’s everyone else. It’s prudent to know which one you’re competing with. The older I get the more I think this applies to everything."

"A pretty much constant paradox is that we expect outlier outcomes from people that we demand act in normal, average ways. We love geniuses after they do the great thing, but we basically loath and harass them if they act in uncouth ways before hand."

"It’s an acute symptom of modernity (late-marriages, no kids, city living, secularization, materialist metaphysics) that we foolishly look to our jobs for meaning."

"Competition proceeds scarcity. Not the other way around. Things are scarce because first we desire them."

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