20VC Cruise's Daniel Kan on Lessons From Scaling The Team From 40 To 1,500 People, How Daniel Thinks About Continuous Learning & SelfDevelopment and Why CEOs Hiring Themselves Out Of Roles Is Wrong

Harry Stebbings interviews Daniel Kahn, co-founder and Chief Product Officer at Cruise, a self-driving car company acquired by GM for $1 billion and has since raised over $7.25 billion. Daniel reflects on his journey from a startup newbie to a celebrated entrepreneur, sharing insights on the importance of clear communication, trust, and delegation within a rapidly scaling team. He emphasizes the need for consistent alignment around common goals and the cultivation of a learning culture underpinned by Cruise's core value of humility. Daniel also stresses the pitfalls of micromanagement and the significance of understanding roles before hiring to solve problems. The conversation also touches on the role of celebration in acknowledging team successes while maintaining focus on future objectives.

• Daniel Kahn is the co-founder and Chief Product Officer at Cruise.
• Cruise specializes in advanced hardware and software for transportation.
• Acquired by GM in 2016 for around $1 billion.
• Raised over $7.25 billion post-acquisition.
• Backed by investors like SoftBank, Honda, and T. Rowe Price.
• Daniel began his career at User Voice, founded Exec, and sold it to Handy.
• Featured as number 7 on Fortune's 2016 "40 under 40" list.

"Now Daniel is the cofounder and chief product officer at Cruise, the company building cutting edge hardware and software that work seamlessly together to transform the way we all experience transportation."

This quote introduces Daniel Kahn's current role and the mission of Cruise, emphasizing the integration of hardware and software in transportation.

• Harry Stebbings promotes his Instagram and behind-the-scenes content.
• Acknowledges Justin Kahn's role in introducing Daniel Kahn for the podcast.
• Shout-outs to ActiveCampaign and Atom for their services.
• Mentions Intercom's impact on customer engagement and business growth.

"I always love to show you our work behind the scenes there, however, to our guest today and I've wanted to have this guest on the show for a very, very long time."

Harry Stebbings expresses enthusiasm for sharing behind-the-scenes content and his anticipation for interviewing Daniel Kahn.

• Daniel Kahn did not originally intend to work in startups.
• Applied to banking jobs in 2009 but due to the financial crisis, ended up joining a startup.
• Influenced by his brother's advice and his environment in the Bay Area.
• Founded Exec after a few years in the startup ecosystem.
• Joined Cruise, which was co-founder Kyle's idea.

"You know what's funny is I actually never intended to be in startups, really."

Daniel Kahn shares his unintentional path into the startup world, highlighting the impact of external circumstances and social influence.

• Daniel Kahn and Kyle Vogt have a successful partnership due to trust and delegation.
• Kyle handles the technology side, while Daniel focuses on operations like HR, finance, and product.
• Their partnership is built on each person's strengths and trust in decision-making.

"I think the biggest thing is we have a lot of trust in each other, and we delegate different aspects of the company to the other person, and we trust that that person is going to make the right decisions to get things done."

The quote emphasizes the importance of trust and delegation in Daniel's partnership with Kyle, which contributes to their effective collaboration at Cruise.

• Daniel Kahn believes that being as good as your team is crucial.
• He advocates for creating self-sufficient teams as a leader's top priority.
• The goal is to scale oneself and achieve more through a trustworthy team.

"Well, I think it's really because as a leader, it's about scaling yourself. You have to scale yourself. You have to be able to do more things, and the only way to do that is to trust."

This quote underlines Daniel Kahn's philosophy on leadership and the significance of team empowerment to extend a leader's capabilities.

• Recognizing the limitation of a 24-hour day, successful leaders must delegate tasks to grow beyond a small business.
• Delegation requires hiring trustworthy individuals and providing them with clear direction and autonomy.
• Growth is unattainable without trusting employees to take on responsibilities.

"You have to be able to hire people who you can delegate and give them direction to say, hey, this is how we work. This is how you should do things here, and then you have to trust them to do so."

This quote emphasizes the necessity of delegation in business growth and the importance of trust in the delegation process.

• Trust can be viewed optimistically (glass half full) or pessimistically (glass half empty).
• Trust is built over time and adjusted based on employee performance.
• Clear hiring practices and criteria are essential for starting relationships with a high level of trust.

"But I think that it is something that is built over time. But if you inherently believe that in yourself and your hiring practices, you should be willing to give people a lot of trust in the beginning."

The quote suggests that while trust develops over time, a foundational level of trust should be granted initially, based on reliable hiring practices.

• KPIs are tools for accountability and motivation.
• Setting appropriate goals is crucial; they should be challenging but achievable.
• Leadership must ensure that goals are collectively understood and that the team is committed to them.
• Adaptability in goal-setting is important, but goals should not be changed at the first sign of difficulty.

"KPIs are just a way to hold yourself accountable and keep the team motivated to do the work that they need to do."

This quote highlights the role of KPIs in maintaining focus and motivation within a team, while also stressing the balance needed in goal-setting.

• Micromanagement can lead to dissatisfaction and is often a sign of unclear expectations or inadequate employee training.
• Leaders should either provide clearer guidance or reassess the employee's role and capabilities.
• Experiencing and learning from failure is critical for employee growth.
• Micromanagement is counterproductive and should be avoided by setting clear expectations or offering guidance without over-control.

"Micromanagement is the easiest way to make everyone miserable, and I've done it before."

This quote conveys the negative consequences of micromanagement and the speaker's personal resolve to avoid it based on past experiences.

• Stretch roles offer personal growth opportunities for employees at startups.
• Micromanagement may indicate that an employee is struggling, necessitating additional support or role adjustment.
• Leaders should balance the potential for growth with the risk of overstretching an employee's capabilities.

"If you hire someone who's already done the job, then they're not necessarily growing in the role."

The quote reflects the philosophy that hiring for potential growth can be more beneficial than hiring based on past experience alone.

• Constant improvement is necessary for personal and company success.
• Stagnation equates to missed opportunities and can lead to competitive disadvantages.
• The speaker advocates for continual learning and development as a means to stay ahead.

"If you're not growing, you're missing out on an opportunity because no one in the world is perfect, right? No company is perfect."

This quote underscores the perpetual need for growth and improvement in both personal and professional contexts to maintain a competitive edge.

• Emphasizing the importance of an organization's culture in learning and adapting.
• The value of humility in acknowledging there's always room for improvement.
• The significance of focusing on solutions rather than dwelling on problems or assigning blame.
• The role of retrospectives in learning from past experiences to enhance future performance.
• The necessity of a forward-thinking mindset in startups for growth and adaptation.

"At cruise, one of our core values is be humble and humility for us is that there's always something to learn out of every experience."

This quote highlights the cultural emphasis on humility at Cruise, which fosters a learning environment where every experience is seen as an opportunity to learn and improve.

"It's not to say that you shouldn't think about the problem so that you don't repeat it, but there's a time and place for retros and kind of understanding, okay, this is what we need to do better in the future."

This quote underscores the balance between learning from past mistakes and not getting stuck on them, indicating the importance of retrospectives at the right time to inform future actions.

• The dilemma of celebrating achievements versus the risk of becoming apathetic.
• The human need for recognition and the importance of praise.
• The balance between acknowledging success and maintaining a focus on ongoing work and future goals.
• The story of Cruise's acquisition by General Motors as an example of celebrating success while staying committed to work.

"And so you do have to balance that. I think you want to take time to congratulate people, call people out on the job that they've been doing, and celebrate as a team on the wins."

This quote emphasizes the importance of celebrating achievements while maintaining a balance with ongoing work, reflecting the human need for recognition and the motivational impact of celebration.

"And I think that was a nice balance of, hey, we're not done because we've been acquired. We still have a long ways to go, and we want to do this right, and we will take the time to celebrate as a team when the time is right."

This quote illustrates the balance Cruise struck between celebrating their acquisition by General Motors and the recognition that there was still much work to be done, showcasing a disciplined approach to success.

• The evolution of a leader's role from execution to providing clear communication as the team grows.
• The significance of aligning the team around common goals and empowering them with the information needed to succeed.
• The importance of consistent and transparent communication, especially in rapidly growing companies.
• The challenges of maintaining culture and ensuring all team members understand and act in accordance with the company's values.

"The biggest learnings? I think the thing that I've learned the most is that as you grow, I think as a leader, your role is basically to provide clear communication to the team."

This quote reflects the shift in a leader's responsibilities as a company scales, highlighting the importance of clear communication in guiding a larger team.

"You have to have a constant stream of clear, consistent communication. And that starts from the moment you walk in the door in our on voter importing programs to we have equally all hands and consistent emails sent out by the leaders of the company around their product areas or some of their areas."

The quote emphasizes the necessity of continuous and consistent communication to keep a growing team informed and aligned, mentioning specific practices such as onboarding programs and regular all-hands meetings.

• The challenge of hiring people to solve problems without fully understanding the problems oneself.
• The potential pitfalls of expecting new hires to solve problems that the hiring team cannot articulate or understand.

"I think hiring people to solve a problem that you don't know how to solve yourself is a little bit of a red herring."

This quote points out the misconception that hiring someone can be a solution to a problem that the existing team doesn't understand, suggesting that a deeper understanding of the issue is necessary before bringing in new talent.

• Founders often seek to hire for skills they lack, such as coding or growth expertise.
• It's vital to first understand the requirements and specifics of the role before hiring.
• Learning the basics of the needed skill can set better criteria for hiring the right person.

Well, if you don't know how to code, how do you know if that code or that person will be good at coding.

This quote emphasizes the importance of having a basic understanding of the skills you are hiring for to ensure you can evaluate candidates effectively.

But we should have spent more time, in my opinion, learning what we needed, figuring out how to make it work, then finding the right person who could take it to the next level.

This quote underscores the lesson that spending time learning about the role and its requirements can lead to more informed hiring decisions and better outcomes.

• Interview questions can reveal much about a candidate's character and communication skills.
• Asking candidates to summarize their work experience is a favored approach.
• The response to this question shows how candidates prioritize information and their ability to communicate clearly.

I always ask people to summarize their work experience.

This quote highlights the interview technique of asking candidates to summarize their work experience to gauge their communication skills and what they consider important.

• Quick fire questions reveal personal preferences and philosophies of the interviewee.
• Topics range from favorite books to desired changes in Silicon Valley.
• Responses to quick fire questions can provide a snapshot of the interviewee's personality and values.

Probably Shogun, because it's all about patience, buildup.

This quote reveals a personal preference for literature that emphasizes patience and buildup, hinting at personal values.

entitlement culture

This quote reflects the interviewee's desire to change the entitlement culture in Silicon Valley, showing appreciation for the opportunities in the tech industry.

I wanted to live a life with as little drama as possible

This quote indicates a personal inflection point that has influenced the interviewee's approach to life and work.

really getting people aligned with the right information

This quote identifies a challenging aspect of the interviewee's role, which is aligning team members with the correct information.

That maybe Harry Potter was a great book.

This quote shows a belief that may differ from those around the interviewee, suggesting a personal opinion about popular literature.

• The focus is on launching autonomous vehicles (AVs) and making them available for public use.
• There is an emphasis on staying focused and not thinking too far beyond the immediate goals.

So we're really focused on getting the launch, putting our avs out there, and making it available for people to ride in.

This quote outlines the immediate goals for Cruise, which involve launching and distributing their AVs to the public.

• Acknowledgments for the support and participation in the podcast.
• Partnerships with platforms like Activecampaign and Atom finance are highlighted.
• The importance of customer experience and investment decisions is underscored.

With their platform, you can create unique customer experiences that attract, nurture, and convert leads into customers into repeat customers.

This quote stresses the role of Activecampaign in enhancing customer experiences and the significance of nurturing customer relationships.

Atom is the financial knowledge platform, democratizing access to institutional quality resources in a really intuitive platform that works anywhere.

This quote highlights Atom finance's mission to provide accessible, high-quality financial information and tools to a broad audience.

Intercom makes that little chat bubble in the corner of a website, opening your business up to customers in quick and friendly ways.

This quote illustrates how Intercom's services can improve customer interaction and support on websites, enhancing the overall user experience.