Strive to be an “A CEO” by anticipating significant changes 6-12 months ahead of others and possessing the decisiveness to alter course, even when facing opposition from those content with the status quo.
Develop coachability by being introspective and willing to respect feedback from all sources—market, employees, customers, and investors—as dismissing it often leads to failure.
Develop a clear vision of the future that doesn’t exist today and be able to articulate it effectively to convince co-founders, employees, investors, and customers to join and see that vision with you.
To achieve significant success, cultivate the ability to diverge from conventional wisdom with a strong, correct opinion, going against the grain when necessary.
Avoid failure by checking ego at the door, ensuring open communication with employees and investing partners, and actively building a culture of success and winning within the company.
In high-risk environments like venture capital, cultivate comfort with failure, understanding that a significant portion of ventures will not succeed, and this acceptance is necessary for the role.
In times of crisis, make drastic and decisive decisions early, even if they seem extreme, as these “no regret moves” can prove correct and beneficial in the long run.
Strive to be an optimistic entrepreneur who clearly sees a different future and actively works to eliminate all barriers to achieving that vision, rather than feeling oppressed by society.
Embrace entrepreneurship as the hardest job you’ll love, recognizing it as the unique opportunity to create significant impact in the world as an individual in business.
Avoid the mistake of relying solely on superior technology; instead, prioritize extensive customer exploration to identify real market pain points and customize your product to solve those specific problems.
Always engage with customers first to understand their needs and problems, and only then proceed to build solutions that directly address those identified issues.
Recognize that effective marketing and sales are more critical for success than just having great ideas or superior technology.
Create a clear, intellectually honest pro forma financial model that details spending, revenue expectations, and a realistic plan for customer acquisition and communication, as this structural plan is fundamental to avoiding failure.
For a CEO, recognize the COO as a critical operations person who fulfills vision and acts as a level-headed, practical counterbalance to enthusiasm and drive.
Avoid the common mistake of equally splitting equity among co-founders without vesting, as this often leads to issues when some co-founders leave but retain significant unearned ownership.
Be cautious of husband-wife or other close familial teams in key leadership roles, as it can create agency issues, insulate leadership from critical information, and hinder effective communication and feedback from direct reports.
When structuring early-stage equity, forward-look the capitalization table to ensure that after future dilution from multiple funding rounds, founders will still retain enough equity to remain highly motivated for the long haul.
When determining valuation and equity splits, ensure the investor syndicate owns enough, the founding team retains sufficient equity for motivation, and the employee option pool is attractive enough to secure talent for long-term success.
Consider investing a small amount of capital and a large amount of time early on to build rapport and assess a founder and market, then significantly increase investment only after proving worthiness and product-market fit.
When evaluating potential partners or team members, focus on meeting them, getting to know them personally, and deciding if they are people you genuinely want to work with.
Recognize that integrity, trust, and rapport are integral to successful relationships, as talented and trustworthy people are at the core of all successes.
When evaluating an entrepreneur, ask about the inception of their idea and their deep motivation, looking for a personal problem they’re compelled to solve rather than just a job or desire to exploit technology.
Maintain humility and acknowledge the impossibility of consistently picking “unicorns” or guaranteed winners, especially at early stages.
As an investor or collaborator, understand that you must be a good partner and actively earn the right to participate and influence, rather than assuming it.
Recognize that venture capitalists bring valuable experience in pattern matching and broad exposure to industry trends, customer behavior, and talent, which can give an edge to venture-backed companies.
When considering an investment or major project, assess three core components: the quality and fit of the team, the viability and innovation of the technology, and the size and growth potential of the market.
For due diligence, actively talk to customers and personal references, deeply understand and challenge the business model, and get to know the team even better to establish all necessary check marks.
Clearly communicate upfront with founders about investment expectations, such as not providing bridge notes or follow-on funding unless specific market-validated milestones are met.
Commit to being a partner with entrepreneurs through all challenges, working hard even with companies that may not achieve massive success, to preserve capital and leverage experience.
When investments go sideways, actively advise companies to sell early to recover capital, or consider leadership changes, to try and right the ship.
Implement a phased investment strategy, deploying minimal capital initially, to create a structural gate for thorough diligence at later stages, allowing you to walk away from early bets with minimal loss if they don’t track.
As an entrepreneur, consider it prudent to take some cash off the table at the Series B stage (or later) to alleviate personal and family stress, but avoid expecting a secondary at the seed stage.
At the seed stage, prioritize extensive customer exploration, talking to potential users, and conducting early trials to gather indications of product utility and market need, rather than assuming product-market fit.
For Series A funding, demonstrate sufficient momentum and early economic ratios (e.g., LTV to CAC) to prove a viable market for your product, validating its potential to scale with more customer conversations.
At the Series B stage, the focus shifts entirely to scaling a proven business model by investing in growth, assuming the “machine” is working and ready for accelerated expansion.
When facing significant change or restructuring, prioritize retaining and hiring individuals who demonstrate a strong ability to adapt quickly to new realities and challenges.
Recognize that individuals from diverse backgrounds, especially those who have experienced tougher lives or relocated to new countries, often possess greater flexibility and adaptability, which are strong indicators of entrepreneurial success.
For early-stage companies, view board meetings as opportunities to step out of day-to-day tactical decisions and engage in strategic brainstorming with aligned partners, focusing on core strategic questions rather than just formal governance.
As a board member, approach meetings with humility and empathy for the intense daily challenges and pressures faced by entrepreneurs.
Recognize that the true value of board meetings lies in the preparation process, which forces CEOs into quiet contemplation, reflection, and accountability, moving them out of day-to-day weeds into strategic thinking.
When challenged, respond contemplatively by taking in the feedback, consuming it, and then dictating your own path, rather than reacting defensively.
To assess coachability, directly challenge assumptions and approaches in initial meetings and observe how individuals react, looking for contemplative responses rather than defensiveness.
Strive to be the “dumbest person in the room” by surrounding yourself with people smarter than you, as this provides a privilege to learn from and work alongside innovators and change agents.
Embrace failure as a natural and acceptable feedback mechanism that provides opportunities for improvement and learning.
Practice listening more and talking less to discover what others know, thereby doubling your knowledge base without giving anything up, and learn from everyone around you.
Adopt a “detective” mindset, assuming everyone knows something you don’t, and make it your mission to uncover and learn that unique knowledge from them.
For professional development, actively consume information (e.g., podcasts, books) that focuses on startup failures to identify mechanisms to avoid, rather than solely looking for success indicators.
Dedicate part of your information consumption to exploring fundamental questions about the meaning of life, happiness, and truth, often by reading a wide range of biographies for insight.
When consuming information, aim for volume and speed (e.g., listening at high speeds) to quickly extract the few key “nuggets” or insights from each source, rather than focusing on every detail.
Recognize three levels of happiness: physical pleasures, the endorphin rush of learning new things, and the ultimate joy derived from philanthropy, giving back, and enriching others’ lives. Focus energy on the latter for ultimate fulfillment.
Understand that the most rewarding experiences in life are often reserved for those who actively help other people succeed.
If you face academic or personal setbacks, take time to reflect, understand the value of your goals, and then renew your commitment to success to turn the situation around.
Recognize that life can be hard on your own and that an academic degree or schooling can be a significant help, reinforcing the commitment to personal success and moving forward.
Look for investment opportunities at the intersection of disparate areas of technology and knowledge, where the “collision” of disciplines (e.g., AI with case law, behavioral psychology with debt relief) creates powerful solutions.
Consider leveraging distributed ledger technologies like blockchain to establish “liquid trust” in business transactions, especially as the world becomes more interconnected and trust becomes increasingly vital.