Two Questions You Should Ask Yourself
Criticizing other people comes easily to us all.
Looking inward is more difficult with much bigger rewards, if executed properly.
Since your time investments become your destiny, here are two questions you should ask yourself at least once per year:
What's my most powerful habit?
Which habit drains my power the most?
By conducting this self-assessment you can reprogram your days, weeks and months. You can lean-in to your power habits and find ways to mitigate or eliminate the power draining habits.
Now, what do I mean by power? It breaks down into a few key facets:
Power as Agency and Autonomy: This is perhaps the most fundamental aspect. It's the freedom to pursue a vision without excessive external constraints. It means controlling your own time, focus, and destiny. It’s the ability to say "yes" to an idea others dismiss, to pivot strategy based on your insights, and to build an organization according to your values. This autonomy is often the primary driver for leaving stable jobs – the power to choose the problem you want to solve and how you want to solve it, rather than executing someone else's agenda.
Power as Creation and Manifestation: Entrepreneurial people see power in the ability to bring something new into existence. It’s the capacity to translate a vision, an idea, or an insight from the realm of thought into tangible reality – a product, a service, a company, a community. Seeing people use something you built, solving a problem you identified – that's a profound sense of power. It's not just having ideas; it's the demonstrated capability to execute and build.
Power as Impact and Influence: Ambition often extends beyond personal success to wanting to make a tangible difference. Power, in this sense, is the ability to effect change, shape markets, influence user behavior, or solve significant problems at scale. It’s seeing your product become an industry standard, your company creating jobs and value, or your ideas shifting the conversation. It's about having leverage – where your actions create disproportionately large outcomes in the world.
Power as Resource Command: This is about the ability to attract and effectively deploy resources – critically, capital and talent – towards achieving the vision. It's not just having money, but the power to raise it based on the strength of your idea and team. It's not just hiring people, but the power to attract A-players who believe in the mission and amplify the company's capabilities. This command over resources is essential fuel for growth and execution.
Power as Resilience and Optionality: The entrepreneurial journey is fraught with uncertainty and setbacks. Power also means having the capacity to navigate challenges, withstand shocks, and adapt. This often comes from achieving a certain level of success, building a strong team, cultivating a valuable network, or securing a robust financial position. It translates into having options – the power to pivot, to weather downturns, to pursue new opportunities, or even to walk away on your own terms.
Ultimately, for many entrepreneurial and ambitious individuals, power isn't an end in itself, nor is it about dominating others. Power is capacity – the capacity to act on one's vision, to create value, to attract resources, to influence outcomes, and to shape one's own path and, potentially, a piece of the future. It's fundamentally about agency and impact.
Now, go do your own self-assessment on the 2 questions above!
Here are my answers to get your brain flowing:
My 5 Most Powerful Habits:
Voracious, Synthesized Learning & Trend Anticipation: My most crucial habit is an insatiable appetite for information, but critically, it's paired with constant synthesis. It’s not just about reading tech news, research papers, or market reports; it's about connecting disparate dots. I dedicate significant time each morning and throughout the week – often early hours before the city truly wakes up – to absorb information not just from mainstream tech media, but from academic journals (like arXiv for AI breakthroughs), patent filings, niche industry blogs, earnings call transcripts of public tech companies (great for understanding sector headwinds/tailwinds), and deep conversations with technical experts and founders outside my immediate portfolio.
The power isn't just in consumption, it's in actively mapping these inputs onto my existing mental models of technology adoption curves, market dynamics, and potential disruption vectors. This allows me to anticipate, rather than just react to, emerging trends – seeing the potential convergence of, say, decentralized identity verification with advancements in edge computing before it becomes a buzzy investment thesis. This proactive synthesis fuels conviction, helps me ask sharper questions during pitches, and allows me to identify non-obvious opportunities or risks others might miss. It’s the bedrock of developing a differentiated investment thesis.
Cultivating Deep, Asymmetrical Relationships: Unfortunately standard networking is transactional; this habit is about building genuine, long-term, high-trust relationships where value exchange is often asymmetrical, at least in the short term. This isn't about collecting LinkedIn connections or attending every industry mixer. It’s about identifying truly brilliant, ethical, and forward-thinking individuals – founders (even those I don't invest in yet), engineers, academics, domain experts, other VCs with different expertise – and investing real time in understanding their perspectives, helping them where I can without an immediate quid pro quo expectation, and building genuine rapport. This might mean making introductions, offering strategic advice based on patterns I'm seeing, or simply being a sounding board.
The power comes from the trust dividends: access to proprietary insights, early looks at promising deals before they hit the broader market, candid backchannel references on potential investments or hires, and a network that proactively surfaces opportunities aligned with my interests. It turns the firehose of potential deals into a curated stream of higher-quality opportunities and provides invaluable perspectives that challenge my own thinking. Slow, patient work, but the compounded returns are immense.
Unflinching Pattern Recognition & Thesis-Driven Filtering: Experience in this business is valuable only if you rigorously analyze successes and failures to codify patterns. My habit is to constantly refine a set of heuristics and apply them mercilessly, driven by my core investment thesis. After every deal (won or lost) and every significant portfolio event, I conduct a mental "post-mortem":
What signals did I read correctly?
What did I miss?
How does this outcome refine my understanding of winning team dynamics, market timing, sustainable differentiation, or go-to-market strategies in this specific vertical?
This process feeds into a dynamic investment thesis – a clear articulation of the types of problems, markets, technologies, and founder profiles I believe have the highest potential for outsized returns right now. The power lies in using this thesis not just as a guideline, but as a strict filter. It forces discipline, helps me say "no" quickly (often the most valuable use of time), and prevents me from getting distracted by FOMO (Fear Of Missing Out) or chasing deals outside my circle of competence just because they seem hot. It’s about knowing precisely what I’m looking for and having the conviction to pass on everything else, no matter how superficially attractive.
Scheduled Deep Work Blocks for Strategic Thinking: The default state in VC can be highly reactive – emails, calls, pitches, partner meetings, portfolio fires. My powerful counter-habit is aggressively blocking out significant chunks of time (at least 2-3 hours, several times a week) for proactive, deep strategic thinking, completely disconnected from immediate communication channels. This is time dedicated to activities like: analyzing portfolio construction and identifying gaps, stress-testing my core investment theses against new data, diving deep into a new technological domain, mapping competitive landscapes, or thinking through second-order effects of macro trends. It’s during these sessions that the synthesis mentioned earlier often crystallizes into actionable insights. The power comes from creating the mental space necessary for non-linear thinking and complex problem-solving, which is impossible when constantly context-switching. It ensures I'm steering the ship based on a considered course, rather than just reacting to the waves.
It’s often during these quiet blocks that the most valuable investment ideas or crucial portfolio interventions emerge.
Practicing Constructive Pessimism & Rigorous Risk Assessment: I am a naturally happy guy and I have to fight that when I do my work. While optimism about the future is essential in venture, my powerful habit is to complement it with a structured form of pessimism during due diligence. I actively force myself to ask: "Assuming this team is smart and the idea is good, what are all the ways this could still fail?" I run pre-mortems, deliberately brainstorming potential failure points – market shifts, competitive responses, technical hurdles, team implosion, regulatory changes, flawed unit economics, etc. This isn't about being negative; it's about identifying potential landmines before investing, assessing their likelihood and impact, and determining if there are credible mitigation strategies. The power lies in moving beyond the founder's optimistic narrative to stress-test the business from every angle. It helps differentiate genuine, defensible moats from wishful thinking, surfaces critical assumptions that need further validation, and often leads to identifying key risks that need to be addressed post-investment.
This habit grounds decision-making in reality, improves the quality of diligence, and ultimately, helps protect capital by avoiding predictable failures, allowing the inevitable unforeseen risks to be managed more effectively.
Now let’s get to the negative points.. and how to address them. That’s vital too.
My 5 Most Draining Habits:
Reactive Firefighting & Constant Context Switching: The single biggest energy drain is allowing the urgent to constantly crowd out the important. This manifests as living in my inbox, responding instantly to every notification, jumping between calls on wildly different topics without mental breaks, and getting pulled into minor operational issues within portfolio companies that the founders should be handling. While responsiveness is valued, excessive reactivity fragments attention, prevents deep thinking (see powerful habit #4), and leads to a feeling of being perpetually busy but not necessarily productive on high-leverage activities. It drains cognitive resources, increases stress, and makes it harder to maintain strategic perspective. The constant switching cost is enormous. Overcoming this requires ruthless prioritization, delegation (to my team, and empowering founders), setting communication boundaries, and consciously batching similar tasks. It's a constant battle in this industry, and letting reactivity win is incredibly draining.
Succumbing to FOMO & Chasing Competitive Deals: The fear of missing out on the "next big thing" is a potent psychological force in VC, and it's incredibly draining when acted upon impulsively. This habit involves getting caught up in the hype cycle, feeling pressured to invest in a hot sector or company simply because other reputable firms are, even if it falls outside my core thesis or circle of competence. It leads to rushed diligence, potentially overpaying based on competitive tension rather than fundamental value, and diversifying into areas where I can't add significant value beyond capital. The energy drain comes from the anxiety of potentially missing out, the stress of competing in auctions, the cognitive load of trying to quickly get smart on unfamiliar territory, and the subsequent drag on returns and focus if these FOMO-driven investments underperform or require disproportionate attention later. Sticking to thesis (powerful habit #3) is the antidote, but the temptation is a constant power drain.
Analysis Paralysis: While rigorous diligence is crucial (see powerful habit #5), there's a point of diminishing returns that drains significant energy and can kill deals. This habit is the tendency to get stuck seeking perfect information in an inherently uncertain environment. It involves endless data requests, commissioning unnecessary expert reports, debating minor points excessively, and delaying decisions while searching for absolute certainty that simply doesn't exist in early-stage investing. The power drain comes from the sheer time and mental effort expended on low-value investigation, the frustration it causes for founders (potentially souring relationships or causing them to choose other investors), and the risk of missing the investment window altogether. It often stems from a fear of being wrong rather than a genuine need for more critical information. Recognizing when diligence is "good enough" to make a conviction-based, albeit imperfect, decision is key to avoiding this drain.
Shallow Networking & Maintaining Too Many Weak Ties: The counterpoint to cultivating deep relationships (powerful habit #2) is the draining habit of superficial networking. This involves attending countless industry events without clear goals, collecting business cards that lead nowhere, maintaining hundreds or thousands of low-context connections on platforms like LinkedIn, and having numerous brief "catch-up" calls that lack substance. While broad awareness has some value, excessive shallow networking drains enormous amounts of time and social energy without yielding proportionate returns in terms of high-quality deal flow, deep insights, or meaningful support. It creates an illusion of being well-connected while lacking the depth required for real leverage. The power drain is the opportunity cost of that time and energy, which could have been invested in building fewer, stronger, more trust-based relationships or engaging in deep work. Prioritizing quality over quantity in networking is essential to conserve energy for impactful interactions.
Confirmation Bias & Echo Chamber Reinforcement: A particularly insidious draining habit is unconsciously seeking out information and opinions that confirm pre-existing beliefs or investment theses, while dismissing or downplaying contradictory evidence. This often involves spending too much time talking only with people who share the same worldview (other investors with similar backgrounds, friendly portfolio founders), overly weighting positive feedback on a company, or explaining away negative signals. It feels comfortable, but it's dangerous and ultimately draining because it prevents learning and leads to blind spots. Breaking out of this requires actively seeking diverse perspectives, cultivating relationships with people who disagree constructively, rigorously questioning my own assumptions, and giving disproportionate weight to disconfirming evidence during diligence. The energy drain comes later, when reality collides with a biased assessment, forcing painful re-evaluations or dealing with the fallout of a poor decision that could have been avoided with more open-mindedness. Fighting this bias requires constant vigilance and intellectual honesty.
See how honest you need to be with yourself?
Remember, ask these two questions:
What's my most powerful habit?
Which habit drains my power the most?
Then ACT on those insights. You can constantly improve your life this way.
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