20VC Top Three Lessons from Working with Jeff Bezos for 23 Years at Amazon, How the Best Leader Hire, Fire, Prioritise and Make Decisions & How to Be Responsible for 1M Employees and Be a Rockstar Husband and Father with Dave Clark @ Flexport



In this episode of 20 VC, host Harry Stebbings interviews Dave Clark, CEO of Flexport and former CEO of Amazon's worldwide consumer business. Dave shares insights into his leadership philosophy, emphasizing the importance of stretching employees beyond their perceived limits and the value of progression over perfection in goal setting. He discusses the traits of successful hires, including the ability to simplify, determination, and intelligence. Dave also reflects on his tenure at Amazon, highlighting the lessons learned about customer-centricity and the challenges of transitioning from an operator to a bureaucrat. Additionally, he touches on personal topics, such as the impact of parenting on patience and presence, and balancing professional ambition with family life. The conversation also covers Flexport's strategic acquisitions, such as Shopify Logistics, and Dave's approach to integrating new teams and fostering a culture of mutual trust and accountability.

Summary Notes

Jeff's Simplification and Context Shifting

  • Jeff is recognized for his exceptional ability to simplify complex issues and context shift.
  • He excels in identifying the essential elements of a problem, disregarding the non-critical aspects, and focusing on the most challenging parts that require high-level intellectual engagement.
  • This skill allows him to efficiently allocate his time and intellectual resources to where they are most needed.

"He can context shift incredibly well. He can quickly sort out the 90% that isn't hard. He doesn't need to worry about because somebody will figure out, and he can very quickly narrow down to the 10% that requires sort of his level of intellect or a senior level intellect to figure out how to solve and what's most important."

The quote emphasizes Jeff's ability to differentiate between tasks that are trivial and those that necessitate his unique intellectual capabilities, allowing him to focus on the latter for problem-solving.

Dave Clark's Career and Contributions at Amazon

  • Dave Clark started at Amazon in 1999 and rose to CEO of the worldwide consumer business by 2021.
  • He was instrumental in the development of Amazon Robotics and the expansion of Amazon's logistics, including the introduction of Amazon's own planes, trailers, and last-mile delivery network.
  • His leadership was significant in managing over 1 million people.

"When this guest left his last position, he was responsible for over 1 million people."

The quote highlights the scale of Dave Clark's leadership responsibilities and his impact on Amazon's operations.

Encouraging Stretch Goals and Employee Potential

  • Dave values providing employees with opportunities to exceed their perceived limitations.
  • He believes in enabling employees to undertake challenging tasks, which can lead to significant personal and professional growth.
  • The approach involves discerning which projects are suitable for experimentation and which require consistent execution.

"I think people too often put limits on what they think their people are capable of out of fear of overstretching them in some way."

This quote reflects Dave's philosophy on leadership and talent development, where he criticizes the tendency to underestimate employees' capabilities.

Handling Failure and Setting Ambitious Targets

  • Dave measures success based on progress rather than strictly on goal attainment.
  • He advocates for setting ambitious goals, understanding that even if not fully met, they can lead to greater overall progress.
  • Dave emphasizes the importance of not penalizing employees for failing to meet stretch goals, as long as substantial progress is made.

"You may miss the 150 yards by 30% of the time or even 40% of the time, but you're far more likely to have 100% over 100 yards."

The quote illustrates Dave's strategy of setting stretch goals that, even when not fully achieved, result in significant advancements.

Traits of Successful Hires

  • Dave identifies simplification, grit, and intelligence as the three key traits of successful hires.
  • He finds that the best hires often challenge him and push him to work harder.
  • The ideal candidate is someone who is not only capable of fulfilling the current role but can also grow into and excel in future positions.

"My favorite hires, I'm a little afraid that they're going to be way better than me."

This quote signifies Dave's approach to hiring, where he looks for individuals who are not just competent but have the potential to excel and drive him to improve.

Lessons from Working with Jeff Bezos

  • Jeff Bezos is portrayed as a visionary leader, but his approach is practical and focused on simplification.
  • He is adept at shifting contexts and prioritizing the most intellectually demanding aspects of a problem.
  • Jeff's efficiency is attributed to his ability to quickly identify and disregard the trivial, focusing his attention on the critical issues.

"He's hyper efficient with the time that he spends because he doesn't waste time on the stuff. That's easy."

The quote captures Jeff's strategic approach to problem-solving and time management by concentrating on the most challenging elements.

Decision Making Framework

  • Dave's decision-making framework involves prioritizing actions that prevent negative outcomes before focusing on those that could lead to promotions.
  • He acknowledges making wrong decisions but maintains a good overall decision-making record.
  • Learning from mistakes and adjusting strategies is a part of his decision-making process.

"First, I do the things that will get me fired, and second, I do the things that get me promoted."

This quote outlines Dave's pragmatic approach to decision-making by emphasizing risk management and then advancement.## Errors of Omission vs. Commission

  • Jeff reflects on his past decisions, emphasizing that errors of omission, where he didn't act on his instincts, are more regrettable than errors of commission.
  • He believes that failing to act on certain opportunities has a more significant impact than making mistakes while taking action.
  • Jeff mentions Amazon's delay in adopting ultra-fast shipping as an error of omission influenced by his conservative approach.

"I personally don't mind any of the mistakes I've made, the ones where we did something and screwed it up, the ones that linger with me are the ones where we didn't do it, where my gut was we should have done this thing and overthought it, or I was too cautious and I didn't do it."

Jeff is expressing that he is more affected by the missed opportunities (errors of omission) than by the mistakes made while attempting something (errors of commission).

Perception of Speed in Business

  • Jeff discusses the importance of marketing efforts in shaping customer perceptions of a company's speed and innovation.
  • He regrets Amazon being late to the game in ultra-fast shipping, which allowed competitors to appear more cutting-edge.
  • The conversation highlights how customer expectations evolve with the market, and companies need to adapt to maintain their competitive edge.

"Sometimes there are a lot of people who say they do things really, really fast, but that's really a small subset of what gets done. But it's a marketing message and customers start to believe have a perception of speed about you as a company."

Jeff is explaining that the perception of speed can be largely influenced by marketing, even if the actual speed only applies to a small subset of services.

Last Mile Delivery Economics

  • Jeff shares his opinion that many venture capitalists have lost money on last-mile delivery companies.
  • He explains the economic challenges of delivery services, such as the need for high delivery density to achieve profitability.
  • Jeff's personal view is that only companies with substantial scale and customers willing to absorb fees will survive in the long term.

"In my personal opinion, yes. The closest I think it gets to working as a model is if you can get to subscription and ad."

Jeff is expressing skepticism about the financial viability of last-mile delivery companies, suggesting that additional revenue streams like subscriptions and ads are necessary for success.

Decision to Leave Amazon

  • Jeff describes his decision to leave Amazon after 23 years to become the CEO of Flexport.
  • His wife's supportive reaction and his desire for a role focused on building and creativity were significant factors in his decision.
  • The transition from an operational role to a bureaucratic one at Amazon was a key motivator for his career change.

"Well, she said it's about time. In all honesty, I considered a sign I married the right woman, which is probably the most important decision I've ever made."

Jeff is sharing his wife's positive response to his decision to leave Amazon, which he takes as affirmation of her being the right partner for him.

Cultural and Operational Lessons

  • Jeff discusses the importance of customer-centricity and how it's tested during challenging financial decisions.
  • He plans to instill the same customer-focused culture at Flexport that he experienced at Amazon.
  • Jeff also touches on the cultural differences between Amazon and Flexport, aiming for an intense yet more empathetic and collaborative environment at Flexport.

"If you're customer centric in a very, very hard moment where you're faced with doing something that the customer would like, but it's going to cost you a lot of money that you really, really don't want to spend."

Jeff is highlighting the true test of customer-centricity, which occurs when a company must decide whether to incur costs to satisfy customer needs.

Trust and Promises in Business

  • Making and keeping tough promises is a mantra Jeff believes in to build trust with people and customers.
  • He emphasizes the significance of delivering on aggressive product roadmaps to gain customer trust.
  • Jeff also discusses the concept of trust with new employees, advocating for giving trust upfront and supporting their success.

"You earn trust in people and you earn trust in customers, and it's easy to say something or to make a promise and not live up to it sometimes."

Jeff is explaining that trust is earned by making commitments and consistently fulfilling them, which is crucial in business relationships.

Hiring Senior Leaders

  • Jeff shares insights on hiring senior leaders, emphasizing mutual trust and accountability.
  • He believes that hiring at the C-suite level is akin to a marriage, requiring long-term commitment and support.
  • Jeff also reflects on past experiences where he may have failed to support new hires adequately.

"I think of it as especially at big C suite jobs or big executive jobs. I think there's a lot of mutual trust and mutual accountability in that hiring decision."

Jeff is discussing the reciprocal nature of trust and responsibility when hiring senior executives, likening it to a partnership.

Company Culture: Teams vs. Families

  • Jeff agrees with the sentiment that companies are teams, not families, highlighting the performance-based nature of professional roles.
  • He distinguishes between personal relationships and job permanence, reinforcing the idea that employment is conditional on performance.

"Yeah, we're not a family because we're all here to do a job and we have a set of roles and responsibilities."

Jeff is agreeing with the view that while personal relationships may exist in a company, the primary objective is to fulfill professional roles and responsibilities.## Internal Promotion vs. External Talent

  • Jeff prefers to hire internally if the right talent matches the need.
  • In fast-growth environments, it's often necessary to hire external senior talent.
  • Internal employees may lack exposure to the future direction of the business.
  • External hires can model behavior and provide guidance to internal talent.
  • The goal is to teach internal employees about leading in new ways for the company's future.

"My preference is to hire internally if the talent is available and matches the need. But in fast growth environments, you often have to intersperse more senior external talent."

This quote emphasizes Jeff's preference for internal promotions but acknowledges the need for external hires in certain growth situations to provide necessary experience and leadership.

Benefits of Naivety and Learning Playbooks

  • Jeff sees value in hiring people early in their careers due to their lack of "bad behavior" from other companies.
  • Entry-level hires can grow with the company and become cultural evangelists.
  • There is a risk of higher attrition with younger employees as they are still discovering their career paths.
  • Hiring fresh talent avoids importing a different company's culture.

"I really like hiring people who are like day one in their career because you have more attrition in that because people are still discovering themselves and discovering what they want to do."

Jeff explains the benefits of hiring individuals at the start of their careers, as they haven't developed bad habits from other workplaces and can fully integrate into the company's culture.

Strategic Acquisitions

  • Acquisitions are seen as opportunities for growth and strategic advantage.
  • Jeff describes the acquisition of Shopify logistics and Deliver as an opportunistic moment.
  • The acquisition was not initially planned for the year but presented a strategic advantage.
  • Acquisitions can accelerate company plans and provide access to new resources.

"It made a ton of sense for us to acquire. We viewed it as would be a pretty effective acquisition and accelerant to our overall plan."

Jeff discusses the rationale behind the acquisition of Shopify logistics and Deliver, viewing it as an effective way to accelerate Flexport's plans and strategy.

Mistakes in Acquisitions

  • The biggest mistake according to Jeff is delaying integration after an acquisition.
  • It's important to quickly become one team and avoid dragging out the transition.
  • Employees from acquired companies are considered part of the new company immediately.
  • There is a willingness to let go of employees who do not fit into the new company culture.

"The thing that is waiting too long to hit the ground running and to just make the moves to integrate."

Jeff highlights the importance of swift action in integrating an acquired company to avoid the common pitfall of delayed integration.

Work-Life Balance

  • Jeff admits to having struggled with work-life balance in the past.
  • He emphasizes the importance of aligning with his partner on their shared journey.
  • Time management and being protective of one's time are crucial for balance.
  • Jeff reserves time for family and work to ensure he can have the maximum impact in both areas.

"The key I found is just becoming more and more aware of what I'm doing with my time, more and more realizing."

Jeff reflects on the significance of being conscious of how he spends his time to maintain a balance between work and family life.

Dealing with Imbalance

  • During COVID-19, Jeff faced significant challenges in balancing work and family life.
  • Communication with his partner and acknowledging mistakes were key to navigating this period.
  • Jeff believes in striving to improve and maintain open communication with his family.

"For me, it's just always been try to be as open in communication as we can be, accept that I screw up a lot and we're heading the same journey."

Jeff shares his approach to managing periods of imbalance, emphasizing the importance of open communication and mutual support with his partner.

The Impact of Relationships on Work

  • Jeff argues that a balanced home life contributes to being a better leader and partner at work.
  • He believes that being happy and balanced personally enables him to perform better professionally.
  • The decision to balance work and personal life is framed as what's best for both the company and the individual.

"I'm a better leader and partner to my teams when I'm at full patience and where I have clarity of thought and I am in that condition best when my home life is also in balance."

Jeff explains how a balanced personal life positively affects his leadership and decision-making abilities at work.

Changes After Having Kids

  • Having children made Jeff more patient and self-aware.
  • Parenthood is humbling and keeps one connected to the real world.
  • Children reflect their parents' behaviors, prompting personal growth and patience.

"I think mostly it just made me more patient. One, I think you see yourself in your kids, you see your behaviors in your children."

Jeff discusses the impact of parenthood on his patience and self-awareness, noting how children mirror their parents' behaviors.

Hardest Part of Parenting

  • Jeff can only speak to parenting children up to the ages of eleven and eight.
  • The hardest part for him is feeling protective and anxious when his children are hurt.
  • Parenthood brings a unique level of concern for one's children's well-being.

"There's never anybody in your life that you're more willing to go crush somebody into a million bits for hurting someone than when they hurt your child in some way."

Jeff shares his feelings about the protective instincts that arise as a parent when his children face harm or distress.## Parenting and Personal Growth

  • Jeff reflects on how having children changed his perspective, making him more empathetic and considerate of others.
  • He emphasizes the importance of being as happy as your happiest child, indicating that a child's well-being significantly impacts a parent's happiness.

"Because when something goes bad, you're only as happy as your happiest child is a pretty common phrase that I hear a lot and it's pretty darn true."

This quote suggests that a parent's sense of well-being is closely tied to their children's happiness, highlighting the deep emotional connection between parents and their children.

Being Present

  • Jeff wishes he had learned to be more present in every moment, whether at work or with family.
  • He acknowledges that children are perceptive and can tell when someone is not fully engaged, which taught him the importance of presence.

"I would be more present wherever I was, whenever I was there." "Kids become good truth tellers at that."

Jeff expresses regret for not being fully present in the past and recognizes the value of undivided attention in all relationships, especially with children who can easily notice when someone is distracted.

Managing Distractions

  • Jeff discusses the challenge of staying present in the moment, particularly due to the distractions of devices like phones and smartwatches.
  • He shares personal experiences of how technology interfered with his ability to be present and the steps he took to mitigate this, such as discontinuing the use of an Apple Watch.

"Like the phone was like the worst. So largely it's like trying to be very conscious of what am I doing with my phone at this moment while I'm engaging with this person."

The quote highlights the pervasive nature of technology in modern life and the conscious effort required to minimize its impact on personal interactions and presence.

Raising Children in Affluence

  • Jeff addresses the challenge of instilling hunger and ambition in children raised in financially secure environments.
  • He and his wife enforce two household rules: do your best and don't be an asshole, aiming to raise well-rounded, empathetic, and likable children.
  • Jeff values curiosity and kindness over academic prestige, indicating that personal qualities are more important than attending prestigious institutions.

"And so we want to like our kids when they're 30. I don't want my kids to be assholes."

Jeff expresses his parenting philosophy, focusing on character development and personal values rather than academic or financial success as the primary goals for his children.

Societal Responsibility

  • Jeff believes in teaching children to respect others regardless of their social status and to understand their societal responsibilities.
  • He discusses the importance of children learning to treat everyone with dignity and respect, from service workers to CEOs, and to contribute to their communities.

"If you teach them to be good people and respect others, whether it's the person at the bank teller or the drugstore or the grocery store, the person who is doing whatever, the waiter at the restaurant, and whether or not it's a CEO who's coming over the house for dinner, they've got to learn that all those people are phenomenal people and they got to treat them all with dignity and respect and that they have responsibility to the communities they live."

This quote emphasizes the significance of instilling a sense of respect and responsibility in children, ensuring they understand the importance of treating all individuals with kindness and contributing positively to society.

Impactful Content

  • Jeff recalls a leadership exercise from high school that left a lasting impression on him, teaching him the importance of treating others well and the lasting impact of one's actions.
  • The exercise involved a visual representation of how hurtful words can damage a person and that apologies cannot fully repair the damage.

"He had this pink heart... He folded in half... He pulls off all these pieces of it, and then he starts apologizing and taping it all back together... it's still never the same. So you best not do it in the first place."

Jeff shares a powerful lesson from his past that influenced his understanding of leadership and the importance of kindness, illustrating that actions have consequences that cannot always be undone.

Personal and Professional Bets

  • Jeff considers his educational choices, moving to Delaware, and leaving Amazon as some of the biggest bets he has taken in his life.
  • These decisions were pivotal points that shaped his career and personal life.

"Single biggest bet is probably where I went to school because I didn't know where Auburn was when I went there. Moving to Delaware with my later to be wife and then maybe leaving Amazon."

The quote outlines key life decisions that Jeff identifies as significant risks, each of which has contributed to his current success and life trajectory.

Gratitude for Team Loyalty

  • Jeff expresses deep appreciation for his team members choosing to work with him, viewing their commitment as a gift and a responsibility.
  • He recognizes the talent of his team and the opportunity cost of their decision to join his venture.

"Honestly, I think coming to work for me, I view it as gift."

Jeff shows gratitude for his team's loyalty and dedication, acknowledging the value of their choice to work with him and the trust they have placed in his leadership.

Painful Lessons and Transformation

  • Jeff shares the painful experience of losing his parents early in life, which was a significant factor in shaping his independence and drive for success.
  • He sees this hardship as a transformative experience that contributed to his resilience and ambition.

"But it was very painful but transformative in a way that I think shaped my independence and self reliance and desire to succeed in a very powerful way early in life."

This quote reflects on the impact of personal loss and the way it can profoundly influence a person's character and motivation, turning a painful event into a catalyst for personal growth.

Hypothetical CEO Role

  • When asked which company he would like to be CEO of for a day, Jeff expresses interest in leading a defense contractor to gain access to secret government files and experience a different industry.

"Lockheed Martin or like some weird defense. I want to go to a defense contractor where I can get into all the deep, most secret government files and access and just go crazy for a little while."

Jeff's response indicates a curiosity for experiencing leadership in a vastly different context from his current role, with a particular interest in the defense sector's secretive and complex nature.

Future Vision for Flexport

  • Jeff envisions a future where Flexport's technology stack facilitates a significant portion of global goods movement, reducing environmental waste and enabling small business growth.

"Well, I think we're going to be sitting down in 2028 saying a massive portion of the world's goods move on Flexport's technology stack."

This quote outlines Jeff's ambitious goals for Flexport, highlighting his vision for the company's impact on global trade and sustainability in the coming years.

Gratitude and Openness

  • Jeff and Harry Stebbings conclude the conversation with appreciation for the wide-ranging discussion, touching on personal, professional, leadership, and logistical topics.

"Happy to do it. If you need some follow up on your relationship advice, I'm happy to have follow up sessions with you for nominal price."

Jeff offers a lighthearted conclusion, signaling his openness to further discussions and his willingness to engage in various topics, including offering relationship advice.

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