Focus on understanding human nature and psychology, as it accounts for the majority of successes and problems in ventures, requiring an ‘armchair psychologist’ approach to diagnose team effectiveness and leadership issues.
Cultivate a Stoic mindset by focusing your energy and attention only on the things that truly matter and are within your control, rather than worrying about external factors.
Combat optimism bias by proactively imagining every possible way a venture could fail, then allocate time, talent, and money to prevent those anticipated negative outcomes.
When making arguments or negotiating, strive to identify the objective truth and present logic that is so clear and irrefutable that others cannot disagree, leading to more effective outcomes.
Cultivate a ‘Hall of Heroes’ – a pantheon of individuals whose decision-making you admire – and invoke their perspective by asking ‘What would X do?’ in challenging situations, also inverting for ‘bad actors.’
Actively question what everyone ‘knows for sure’ and linear predictions, looking for ‘informational surprise’ where widely accepted trends might suddenly reverse, leading to significant shocks.
First, understand what everyone else is focusing on, then actively seek out the ‘white space’ – areas or ideas that others are not looking at – to find unique opportunities.
Identify ‘directional arrows of progress’ – undeniable, universal principles or trends that indicate a clear direction of technological or societal advancement, as these trends are likely to continue regardless of individual actors.
Be humble about the amount of luck in your pursuits to open yourself to randomness and optionality, then maximize these opportunities as cheaply as possible.
Actively seek out and leverage chance meetings and unexpected circumstances, as many significant life and business opportunities arise from unpredictable events.
To master a new domain, combine voracious reading of scientific papers and journals with extensive networking, talking to 20-30 experts weekly, triangulating information, and iteratively refining your understanding and narrative to build credibility and recruit talent.
Consistently ask ‘What sucks?’ about existing products, processes, or situations, as identifying pain points and inefficiencies is a powerful way to uncover opportunities for innovation and improvement.
Look for individuals who possess irreverence and a slight arrogance, holding a strong vision of how the world ought to look and disagreeing with consensus, then support them.
When evaluating a technology or company, always ask the fundamental question: ‘Does it work?’ to ensure the core offering is functional and not based on unsupported claims.
View risk and value as interchangeable; actively identify and ‘kill’ risks in a project or venture, as each risk eliminated creates subsequent value and reduces the required return for future investors.
Build a culture that is internally collaborative, emphasizing information sharing among team members, while maintaining an externally competitive stance against rivals.
Adopt a blunt and direct communication style for difficult conversations, ensuring feedback is focused on improving the situation or firm, not on personal attacks, and expect the same in return.
Proactively ask for bad news from partners and team members, emphasizing that this is where you can truly help and collaborate, rather than just celebrating successes.
Be cautious when there is 100% consensus on a decision, as high confidence and complete agreement can be a signal that something important has been overlooked.
For critical decisions, intentionally designate a ‘red corner’ or devil’s advocate to proactively identify all potential reasons why a plan might fail and what could go wrong.
Systematically record individual judgments, perceptions, and observations for each decision to combat selective memory, refine future judgment, and encourage more nuanced rather than absolute viewpoints.
When evaluating dissenting opinions, focus on identifying what information is ‘knowable’ and verifiable through diligence, then actively seek out that information to reduce uncertainty or confirm biases.
Prioritize long-term financial discipline over chasing every opportunity, being willing to forgo a deal if the price is too high, to protect capital and maintain a consistent investment philosophy.
Practice distilling complex issues to their most critical 10%, absorbing all information, taking notes, and then identifying the single most important point or insight.
Cultivate the ability to hold two opposing ideas in your head simultaneously without losing the capacity to function, as this is a mark of a first-rate intellect and helps navigate complex, uncertain situations.
Strive to identify ‘unseen targets’ or technological secrets that nobody else has discovered, as this represents genius-level insight and is where the highest value opportunities lie.
Read a wide variety of news sources, including mainstream and less ‘sophisticated’ ones like USA Today, and look beyond front-page headlines to find ‘meta insights’ in less prominent sections, which may hold undervalued information.
Start the day by checking emails, then Twitter, followed by skimming scientific papers and blogs for headlines, patterns, and trends, taking screenshots, and assembling collages of interesting phenomena to share with your team.
Seek out topics or areas that nobody else is talking about or thinking about, as these often represent overlooked opportunities where significant value can be found.
Identify individuals or groups who are inventing the future and possess unique, asymmetrically distributed knowledge, then build relationships and persuade them to partner with you before everybody else discovers them.
Look for scientists who are highly prolific, publishing many cutting-edge papers, driven by both discovery and the desire for reputation, as these individuals often lead to significant innovation.
Seek out and develop relationships with aggressive, commercially-minded postdocs in the labs of famous, successful scientists, as these individuals often form a ‘fountain of opportunity and innovation.’
Cultivate strong storytelling ability to effectively recruit talent and attract investors, as it creates a powerful emotional connection and persuades people to join or invest in your vision.
During presentations, observe if a leader dominates the conversation or if they delegate and laud their team members, as the latter indicates a positive, trusting leadership style.
Carefully vet the advisory board members of a company, as the presence of ‘BS scientists’ or promoters can be a ‘red flag’ signaling poor judgment from the CEO in discerning credible experts.
Continuously reduce ignorance and evolve your narrative through learning, as increased credibility makes it easier to recruit serious people and build an advisory board for new ventures.
Actively prioritize how to help your portfolio companies by tracking their key metrics and immediate needs (e.g., specific hires), then leverage your network to provide targeted support.
Systematically collect and share information across your team to create collective intelligence, allowing you to connect dots, identify competitive advantages (e.g., better lending terms), and apply insights across your portfolio.
Ensure all team members consistently recap meetings, conversations, and board meeting tidbits, as this institutionalizes knowledge, creates an internal network effect, and prevents information silos.
When investing, quantify how much capital is needed to achieve specific milestones within a defined timeframe, funding incrementally to de-risk the venture and adjust future investments based on progress.
Before a presentation, provide the presenter with the key questions the team will ask, allowing them to prepare thoroughly and address critical concerns effectively.
Implement a ‘one per fund’ rule where partners can push through a highly convicted investment despite team skepticism, to prevent errors of omission and foster long-term camaraderie.
To encourage interaction among people, design physical spaces with narrower halls and tighter structures, as constraining space can lead to more engagement than large, open atriums.
Design office environments with open spaces and glass offices to encourage natural information flow, increase optionality for spontaneous interactions, and allow people to observe who is coming and going.
When evaluating scientific claims, rely on established filtering processes like peer review and publications to determine if a hypothesis is supported by observed, tested evidence and conclusions.
Continuously balance exploration (ingesting new information and ideas) with exploitation (applying existing knowledge), recognizing this is a constant trade-off that can lead to information anxiety but is crucial for growth.
If your schedule allows, dedicate late-night hours (e.g., 11:30 PM - 1 AM) for personal reading, focused work, and consuming audiobooks at high speed to maximize learning and productivity.
Recognize that attention is the most valuable currency with children; reward positive behavior with fully engaged, eye-contact attention to provide the best positive feedback and encourage desired actions.
Teach children the principle ‘it’s better to have it and not need it than need it and not have it’ to encourage thinking about hedging, preparedness, and potential long-term consequences in various situations.
Indoctrinate children with skepticism by encouraging them to question everything and reason through beliefs, rather than simply accepting dogma, by asking ‘What do you think?’ when they inquire about things like Santa Claus.
Actively review examples of people making poor decisions (e.g., from news stories) with your children, discussing the chain of events and motivations, to teach them to learn from others’ mistakes and avoid similar pitfalls.
Guide children to understand the balance between fitting in and standing out, recognizing when it’s appropriate to conform and when it’s crucial to assert their individuality, especially in situations like standing up for others.
Consistently reinforce the value of persistence by asking ‘Does our family give up? Never,’ to instill a mindset of not giving up when facing frustration or challenges.
Be wary of leaders who are control freaks, as this can signal a lack of trust in their team, poor hiring decisions, or an attempt to hide information by controlling every decision.
When evaluating older CEOs, consider that those who chose not to have children may lack the humility gained from parenting, which can influence their management style and ability to handle irrational behavior.