10+1 Lessons from Serial Entrepreneur Justin Kan | Summary and Q&A

TL;DR

Justin Kahn, a repeat entrepreneur, shares his experiences and lessons learned from building multiple companies.

Key Insights

• 🔁 Repeat entrepreneurs have the advantage of learning from previous company experiences and applying those lessons to future ventures.
• ✳️ The distinction between market risk and execution risk plays a crucial role in deciding the strategy and funding approach for a startup.
• 💪 Building a strong company culture and prioritizing organizational health can have a significant impact on long-term success.
• 🥹 Managing stress and personal growth are essential for sustainable entrepreneurship, and practices like gratitude journaling and mindfulness can be beneficial.
• ❓ Mentorship and learning from experienced entrepreneurs, peers, and executive coaches contribute to personal and professional development.

Transcript

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Questions & Answers

Q: What were some of the challenges Justin Kahn faced with his first company, Kiko?

Kiko, a Google Calendar-like platform, failed to gain traction and was eventually sold on eBay after failed acquisition attempts. This experience taught Kahn the importance of product-market fit and the need for continuous learning.

Q: How did Justin Kahn transition from streaming live video to starting a law firm for startups?

After running Justin.tv and Twitch, Kahn incubated various ideas and started companies in different industries. He ultimately realized the potential and need for a technology-enabled law firm for startups, which led to the creation of Atrium.

Q: How does Justin Kahn manage stress and personal growth as an entrepreneur?

Kahn practices daily gratitude journaling, follows a high-fat diet to maintain energy, exercises regularly, and meditates using the Transcendental Meditation technique. He also focuses on removing attachment to outcomes and prioritizes personal well-being.

Q: How does Justin Kahn approach mentorship and learning from others?

Kahn has received mentorship from experienced entrepreneurs, such as Paul Graham, and values peer mentorship from his successful founder friends. He also emphasizes the importance of having an executive coach and continuous learning, which includes reading books like "The Untethered Soul" and "Leadership and Self-Deception."

Summary

In this video, Justin Kahn, a repeat entrepreneur and founder of companies like Kiko, Justin.tv (which later became Twitch), and Atrium, shares his experiences and insights on being a repeat entrepreneur. He discusses the challenges and advantages of starting multiple companies, the importance of focusing on execution risk, his strategies for managing stress and personal growth, the role of mentorship in his journey, and the significance of company culture.

Questions & Answers

Q: Can you share some details about the companies you've been involved in?

Justin mentions his first company, Kiko, which was a calendar app that launched before Google Calendar but didn't succeed. He then started Justin.tv, a live video reality TV show that eventually evolved into a live video platform. The company went through various pivots and eventually became Twitch, which was later sold to Amazon. Justin also started other companies like Socialcam and Exact, and his current project is Atrium, a technology-enabled law firm for startups.

Q: How did you decide to shift from being an investor to starting a new company with Atrium?

Justin explains that while he enjoyed being an investor and helping early-stage founders, he realized that the feedback cycle was not fast enough and he wasn't continuing to learn and grow. He wanted to experience personal growth as a founder, and starting a new company like Atrium presented the opportunity for that. He also saw the potential to solve the problems he faced as an entrepreneur dealing with legal matters, making legal faster, more transparent, and predictable for business owners.

Q: Can you explain the concept of market risk and execution risk in startups?

Justin distinguishes between market risk and execution risk. Market risk refers to starting a company in a new or uncertain market where the demand and business viability are uncertain. In such cases, there is a higher chance to win because there is often little competition from experienced entrepreneurs. On the other hand, execution risk relates to improving existing markets or industries by doing things better or differently. In execution risk startups, the advantage lies in the skills and abilities acquired over time, making it more difficult for less experienced entrepreneurs to compete.

Q: How do you manage stress as an entrepreneur, and how has your approach changed over time?

Justin admits that in the early days, he didn't handle stress well and resorted to unhealthy coping mechanisms like avoiding problems or using alcohol. However, he has since explored various techniques to manage stress effectively. These include practicing daily gratitude through journaling, adopting a ketogenic diet to increase energy levels, exercising regularly, and incorporating meditation into his routine. These practices have helped him become more present, emotionally stable, and satisfied with life.

Q: Who are some of your mentors, and how do you curate your mentorship as you progress in your career?

Justin mentions several mentors, including Paul Graham, the founder of Y Combinator, and Paul Buchheit, the creator of Gmail. He emphasizes the importance of mentorship in his entrepreneurial journey, both from early-stage mentors who supported him in the early years and peers who have achieved success. These peers, such as his cofounder Emmett Shear (Twitch), his brother Kyle Vogt (Cruise), and Drew Houston (Dropbox), provide invaluable insights and lessons from their own experiences. Justin also mentions the value of an executive coach who has been instrumental in his personal and professional growth.

Q: How has your focus on company culture evolved over time, and what principles do you aim to implement?

Justin acknowledges that in the early days, his focus was primarily on hitting milestones and metrics rather than shaping the company's culture. However, he realized the importance of a strong culture and has since become intentional about it. He believes that execution will flow from a culture that encourages empathy, collaboration, and a sense of personal responsibility. To build this culture, Justin is implementing the principles of conscious leadership, which emphasize radical responsibility and empowering team members to take control of their own experiences within the company.

Q: How do you differentiate between market risk and execution risk when determining business strategies?

Justin explains that market risk involves starting a company in a new or uncertain market, where the demand and viability of the business are uncertain. In these cases, the goal is to be the first in the category and take advantage of the lack of competition. On the other hand, execution risk involves improving existing markets or industries by doing things better or differently. Here, the aim is to execute effectively and efficiently to outperform competitors. The choice between the two strategies depends on the entrepreneur's skills and the stage of their entrepreneurial journey.

Q: Is raising a lot of money upfront always the best strategy for a startup?

Justin believes that raising a lot of money upfront is not always the best strategy. While it may provide resources and support, it can also lead to reckless spending and increased pressure to meet higher expectations. It can be more beneficial for startups focused on execution risk to have a capital-efficient approach and raise money strategically based on the specific needs and growth plans of the company.

Q: How do you approach building a company that aligns with your personal values and beliefs?

Justin shares that he has recently started thinking about the kind of company he wants to build and the cultural aspects he values. He believes that aligning personal values with the company's values and culture is crucial. By prioritizing empathy, collaboration, and personal empowerment, he aims to build a company he would want to work at and that encourages the same values in its employees.

Q: How has your perception of success and happiness changed over time as an entrepreneur?

Justin reflects on how his attachment to the outcomes of his companies and external factors had affected his happiness in the past. He realized that relying on external success or achievements to determine his happiness was unsustainable and could lead to disappointment. His perspective now is that sustainable happiness comes from within, regardless of the external circumstances. He has learned to detach his identity and happiness from the outcomes of his company and focus on the journey and personal growth.

Q: How important is personal growth and continuous learning in your career?

Personal growth and continuous learning are paramount in Justin's career as an entrepreneur. He believes that startups are a catalyst for personal growth, as they force individuals to learn and adapt under pressure. Even after multiple successful startups, he felt the need for personal growth, leading him to start Atrium. He acknowledges that without growth and challenging oneself, stagnation can occur, and the learning curve flattens. Personal growth helps him stay engaged, adaptable, and motivated to tackle new challenges.

Takeaways

Justin Kahn, a seasoned entrepreneur, shares valuable insights into the world of startups and entrepreneurship. He highlights the importance of differentiating between market risk and execution risk when determining business strategies. Justin also emphasizes the significance of personal growth, stress management, and the role of culture and mentorship in entrepreneurial journeys. He suggests that building a company aligned with personal values and beliefs, and cultivating an intentional company culture, can drive successful execution and attract the right talent. Additionally, he reminds entrepreneurs to detach their happiness from external outcomes and focus on the learning and growth that comes from the startup journey.

Summary & Key Takeaways

• Justin Kahn's first company, Kiko, was unsuccessful and was eventually sold on eBay. He then started Justin.tv, a live video streaming platform, which eventually became Twitch and was sold to Amazon for $970 million.

• Kahn has also started other companies, including Exact (in the home cleaning space) and Whale (a video Q&A app). He is now focused on his latest venture, Atrium, a technology-enabled law firm for startups.

• Throughout his entrepreneurial journey, Kahn has learned the importance of market risk vs execution risk, the significance of company culture, and the need to manage stress and personal growth.