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.
"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.
"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.
"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.
"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.
"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.
"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.
"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
"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).
"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.
"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.
"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.
"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.
"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.
"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.
"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
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.