GitHub Start Up Wednesday with Jason Shen

Introduction to GitHub Startup Wednesdays and Jason Shen

• GitHub Startup Wednesdays is a show that highlights innovative startups and provides opportunities for entrepreneurs to build their businesses using GitHub's platform. The program offers full access to GitHub Enterprise for up to 20 seats for 12 months, along with tailored product guidance, personalized onboarding, and office hours. (1m24s)
• The GitHub for Startups program is free to join and provides a network of founders and entrepreneurs, sharing technical best practices and insights into the GitHub ecosystem. (2m32s)
• Jason Shen, a guest on the show, is a three-time venture-backed founder with experience in Y Combinator and the Alexa Accelerator. He has held product leadership roles at companies like Meta and Atlassian and is the author of "The Path to Pivot," a playbook for business transformation. (3m4s)
• Jason Shen is a two-time Stanford graduate and former NCAA National Champion, with insights featured in major publications and a TED talk on the future of talent that has reached over 5 million viewers. (3m37s)

The Concept of the Outlier Founder

• The discussion highlights the concept of being an "outlier" and its relevance to startups, emphasizing that most founders are outliers due to their willingness to leave conventional jobs and pursue entrepreneurship, which involves going against the grain. (5m11s)
• Outliers are described as individuals with exceptional talents and strengths, such as technical skills or effective communication, but they also face significant challenges, like difficulties in public speaking or adhering to corporate structures. (6m36s)
• These individuals often have unique perspectives due to their skills and challenges, which can lead to resistance from others who may feel threatened by their ideas and the changes they propose. (7m24s)
• The term "outlier coach" is used to describe working with ambitious individuals, including venture-backed founders, bootstrap business owners, and leaders who see the world as full of possibilities for improvement. (7m43s)
• The conversation also touches on the idea that being a founder, especially if one is neurodivergent or an immigrant, offers a distinct experience and perspective within the startup ecosystem. (8m15s)
• A connection is made to a TED Talk that discusses demonstrating readiness for a job despite not appearing qualified on paper, focusing on skills over experience, which ties back to the concept of outliers. (8m33s)
• The concept of being an outlier is crucial, as it involves supporting people who aren't necessarily being seen, and this pattern is still relevant today (8m53s).

The Founder's Mindset: Delusion vs. Reality

• To be a successful founder, one needs to have a delicate balance between being delusional and being too fact-based and reality-based, riding the fine line between madness and genius (10m1s).
• Founders need to be a little bit delusional to have the confidence to believe in their ideas, even if they seem wild and crazy, and this confidence can be a double-edged sword (11m12s).
• Successful founders, such as Elon Musk, have a mix of genius and insanity, and this combination can be both beneficial and challenging (10m32s).

Founder Mode and Domain Expertise

• The concept of "founder mode" was introduced by Paul Graham, and it involves taking control of one's business, rather than just letting professional managers run the show (11m51s).
• Founder mode is not fully defined by Graham, but it can be interpreted as an exercise for founders to take ownership of their businesses and work towards making their vision a reality (12m35s).
• Founders can use resources such as Paul Graham's essays and other founder-focused materials to help them get into "founder mode" and achieve success (11m42s).
• The current business landscape is highly competitive, with many startups emerging, and founders need to have the right qualities and mindset to stand out and succeed (9m36s).
• Founders tend to have domain expertise in their problem area, solution area, or market, which gives them the ability to start a company and make informed decisions, but they may not know everything and can be impressed by others' credentials, losing sight of their own unique spark and intuition (13m1s).
• Founders are often spiritually connected to their company, allowing them to make decisions and take actions that a professional manager cannot, such as renaming the company or taking bigger risks, and they can get more buy-in from their organization and the world (13m59s).
• This connection gives founders a special superpower, but it can also be a double-edged sword, as they may be seen as tyrants or dictators if they don't care about people and are only focused on achieving their goals (14m52s).
• Founders need to be aware of their limitations and recognize when they are moving into an area where they don't have domain expertise, as "founder mode" may not work in those situations, and they should surround themselves with experts and listen to their advice (15m47s).
• It's essential for founders to operate from a place of strength and take a different approach when they are not in their area of expertise, and there are times when they can engage in "founder mode" and take control of the company, but also times when they need to step back and let others lead (16m3s).
• Examples of founders who have successfully utilized their domain expertise include Elon Musk with electric cars and rockets, but he has struggled with Twitter, demonstrating that expertise still matters (15m18s).
• Founders should rise above themselves with experts and still be in "founder mode" while having people advise them for the best, and it's crucial to recognize when to engage in "founder mode" and when to take a different approach (15m57s).

The Founder's Journey: Personal Experiences and Refactor Labs

• Founders need to balance intense focus on solving problems with a tolerance for uncertainty and ambiguity. (16m40s)
• Many founders have a personal and spiritual connection to their projects, which becomes more significant when they start employing people who depend on them. (17m11s)
• Recognizing personal gaps is important for founders, and they should seek help in areas like speaking to investors and approaching certain conversations. (17m33s)
• Refactor Labs is a venture aimed at helping founders grow, and it was created to address specific needs in the entrepreneurial journey. (18m12s)
• The speaker shares a personal journey of immigrating from China, dealing with ADHD, and finding a path through gymnastics, which led to an athletic scholarship at Stanford and exposure to entrepreneurship. (18m38s)
• The individual had parents who worked in education and were unfamiliar with technology and entrepreneurship, but they entered the tech industry during the resurgence of the dot-com boom, when companies like Facebook were emerging. (19m53s)
• They worked at a startup after school and later founded a company called RideJoy with Y Combinator, which was a long-distance ride-sharing platform. The company faced challenges and eventually failed after unsuccessful attempts to pivot. (20m10s)
• After the failure of RideJoy, they moved to New York, worked at a Series B enterprise software company, and then at Etsy. They eventually gained the confidence to start another company focused on tech hiring and talent evaluation, which led to a successful pivot into developing a voice AI assistant for gamers. (20m59s)
• The voice AI company collaborated with the Alexa accelerator and Amazon, but faced technological limitations and the impact of the pandemic, leading to a small exit opportunity to join Meta. (21m33s)
• At Meta, they experienced the workings of a large corporation but felt restricted despite the company's fast-moving ethos. They contemplated starting another venture-backed company but reconsidered due to personal life changes and the desire to start a family. (22m4s)
• Reflecting on the support received from an executive coach during previous startups, they decided to pursue coaching, starting part-time and eventually committing to it full-time, leveraging their past experiences. (22m33s)
• Many clients in their mid to late 20s, often first-time founders with limited work and life experience, seek more support than what is typically available, such as brief interactions with Y Combinator partners. (23m10s)
• Refactor Labs was established about a year and a half ago after leaving Meta, with the aim of providing coaching, workshops, and content to help founders upgrade their systems and become more resilient. (23m35s)

The Pivot: Grip, Pivot, or Quit

• The concept of resilience and the ability to pivot is emphasized, with a reference to a decision-making tool called the "grip, pivot, or quit Matrix," which helps evaluate whether to continue or change direction. (24m58s)
• The "grip, pivot, or quit Matrix" and the subsequent "align, explore, commit" framework are derived from a book titled "The Path to Pivot," written in the fall of 2023, which reflects on past pivots and the willingness to pursue better opportunities. (25m56s)
• Before considering a pivot, it is important to assess whether maximum effort has been given to the current venture and whether it has been given enough time to succeed, as new ideas often take time to develop. (26m44s)
• Quitting is an option when the situation is dire, but many people tend to quit too late, often when resources are nearly depleted. (27m30s)
• Pivoting is a middle ground where one can retain some successful elements of the current venture while moving in a new, significantly different direction, avoiding starting from scratch. (27m47s)
• The process of pivoting involves aligning with co-founders to acknowledge the need for change, mapping out a plan, and conducting a "pivot pilot," which is a test to explore new directions without completely abandoning the current project. (28m47s)
• During the exploration phase, it is crucial to communicate with the team and investors about the new direction, extend the financial runway by cutting costs, and thoroughly investigate the new area over a set period. (30m8s)
• An entrepreneur successfully navigated the pandemic by getting his entire company to agree to a 30% salary reduction, allowing them to retain all employees and eventually grow faster (30m35s).
• Another client, who comes from a finance and trading background, initially had multiple crypto-related ideas but ultimately found himself passionate about meme coins, leading to a pivot in his business (31m7s).
• When considering a pivot, it's essential to spend six to eight weeks investigating, prototyping, and testing before deciding whether to go back to the old idea, lean into the new one, quit, or start a new exploration period (31m35s).
• Setting a deadline for oneself ahead of time allows for honesty and forces a decision, making it necessary to sit down with the team and make a call (31m55s).
• Owning the story and being able to explain the reasoning behind a pivot is crucial, as it can create confidence and help win new supporters while bringing old ones along (32m18s).
• Founder expertise is often harder to express and less legible, making it essential to learn how to tell the story and communicate pivots effectively using frameworks (32m48s).
• Having a clear story and getting everyone on the same page can make a significant difference in making a pivot successful and gaining support (33m40s).

Evolution, Pivots, and Success Stories

• A natural evolution of a business can occur, and it's essential to communicate this change effectively to stakeholders, as seen in the evolution of companies like Twitter, Slack, and Instagram (34m4s).
• Helping founders have conversations about their business and pitch is crucial, especially when raising new money, and this is one of the things done at Refactor Labs (34m16s).
• Some investors like it when a company pivots because it means they learned something in the real world and adapted to it (34m40s).
• Owning the story from the beginning and understanding how to communicate it is key, and a pivot can be a success story for many companies (35m6s).
• Companies like Slack and Discord started as game companies but eventually became successful communication tool companies (35m27s).
• The founder of Slack, Stewart Butterfield, also started Flickr, which began as a game and turned into a photo-sharing platform (35m54s).
• One of the co-founders of GitHub now has an indie game studio, showing that people can pivot and try new things even after achieving success (36m12s).

Experience at Meta and Large Companies

• The experience of working at a big company like Meta can provide security and funding for personal dreams, and Jason Shen's last company, Midgame, was acquired by Meta (36m59s).
• Midgame was a small team of three people when it was acquired, and Jason Shen stayed on as a product manager for several years after the acquisition (37m22s).
• A team was acquired by Meta to work on internal productivity tools, focusing on knowledge retrieval and discovery to manage the vast amount of information within the company's gigantic code base and documentation (37m31s).
• The team's goal was to support Meta employees, allowing for a deep look into how large companies operate, with a significant difference in scale compared to smaller companies like Etsy (38m11s).
• Large companies like Meta have incredibly smart, thoughtful, kind, and ambitious people, but working at such a company requires being very good at one's job due to the limited time available for actual work (38m35s).
• At Meta, employees have to spend a significant amount of time on tasks outside of their core job, such as attending meetings, reading reports, and understanding various tools, leaving only a short time for focused work (38m54s).
• As a result, the work done during this focused time must be of high quality, with limited opportunities for iteration, especially in senior roles (39m23s).
• The opportunity to work at a giant scale can be exciting for many, but it may not be the best fit for everyone, as it requires a specific way of working (39m40s).
• Perfect execution is crucial in evaluating a strategy, as poor execution can make it impossible to determine whether a strategy is flawed or if it was just poorly implemented (39m57s).
• This concept applies to startups as well, where most things don't work, and it's essential to be able to distinguish between a bad strategy and poor execution (40m34s).
• Even at large companies like Meta, not all projects are successful, and some engineers may work on projects that never ship externally, despite potentially reaching millions of people (40m43s).
• In large companies, projects often get passed between individuals, leading to a lack of ownership and investment in the work. This can result in projects being deprioritized and ultimately failing, which is demoralizing for the team involved. (41m22s)
• Startups can learn from the operations of large companies like Meta by understanding the importance of focus and commitment to a project, even when initial signals are not promising. This involves being somewhat "delusional" in believing in the potential of a project despite challenges. (42m13s)
• Large companies, including OpenAI, face challenges in prioritizing projects due to their size and multiple priorities. Startups can compete by caring more deeply about the problem, customer, and market, which can be an advantage over larger, more diffused companies. (43m18s)
• It is crucial for individuals in startups to champion their projects and execute them strongly, regardless of whether they are ultimately incorporated. This sense of ownership and effort is important for personal and professional fulfillment. (44m8s)
• Most new projects, whether at large companies or startups, do not succeed. This is a common reality that both environments face, highlighting the importance of persistence and dedication in the face of frequent failure. (44m33s)

The Startup vs. Big Company Dilemma

• Starting a company can be a significant difference from working at a big company like Facebook, as it provides a sense of ownership and personal satisfaction when shipping something made with one's own hands (44m47s).
• However, it's essential to consider the importance of a paycheck and financial stability, and one should only start a company when they feel fired up about it and willing to take the heat (45m11s).
• Being an entrepreneur requires finding one's own way to acquire the next customer, and it's not just going to happen automatically (45m30s).
• While doing what makes one happy is crucial, having a place to live and food to eat are also essential, and sometimes getting a paycheck is necessary (45m52s).
• The question of when to give up on a startup or idea is a personal one, and it's essential to know oneself and not compare to others (47m28s).
• Some people hold on to their ideas for too long, while others give up too quickly, and most people who succeed in life tend to stick to it too long rather than not long enough (48m7s).
• It's common for entrepreneurs to face rejection multiple times before achieving success, and it's essential to persevere and not give up too quickly (48m21s).
• Many people give up easily when their initial attempts at something don't work, but those who are successful often make numerous attempts before achieving their goals (48m33s).
• It's essential to understand what drives you to start something, whether it's to prove someone wrong or because you genuinely believe it's something that needs to exist in the world (49m6s).
• Having self-awareness and knowing what you really want is crucial in making big decisions and persevering through challenges (49m46s).

Perseverance, Resilience, and Self-Awareness

• The "align, explore, commit" framework is a powerful tool for making decisions and giving yourself deadlines (49m51s).
• Comparison can be the thief of joy, and people often only share their big moments, not their failures, which can create unrealistic expectations of overnight success (50m11s).
• Behind many big successes, there are often numerous failures that are not discussed publicly (50m50s).
• Resilience is key, and it's essential to learn from failures and keep moving forward (51m2s).
• Even successful individuals may face setbacks and rejections, such as not receiving direct promotions or facing disappointment from others (51m5s).
• It's essential to focus on what you can control and keep working towards your goals, even in the face of adversity (51m39s).
• The importance of acknowledging failures and learning from them is emphasized, as it is a crucial part of growth and development (52m41s).
• The path to success is often not straightforward, and it's essential to be open about failures and setbacks to help others learn and grow (52m54s).

The Future of Talent and Work

• The future of talent acquisition and entrepreneurship is discussed, with a focus on the changing landscape and the need for adaptability (53m5s).
• A trend in talent acquisition is the use of paid consulting work as a way for companies to evaluate potential hires before making a job offer (54m6s).
• This approach can also be beneficial for individuals looking to transition into a new role, as it allows them to demonstrate their skills and build relationships with potential employers (54m19s).
• One example of this approach is a client who used their time between jobs to network with CEOs and senior leaders, and eventually landed consulting work with several companies, which led to a strong job offer (54m21s).
• This approach requires individuals to bet on themselves and their abilities, much like a founder would, but can lead to a strong fit and alignment with the company (55m26s).
• This trend is particularly relevant for senior leadership roles, where the stakes are higher, and the need for a strong fit is more critical (55m31s).
• One of the investors mentioned was the former head of Cortana at Microsoft, who invested during a transition period between leaving Microsoft and joining Google Workspace. This highlights the importance of creating space and finding the right opportunities. (55m33s)
• The use of AI in job applications is discussed, with a recommendation for using platforms like applyall.com to leverage AI in applying for multiple roles. This approach can be strategic and effective, though not necessarily fair or egalitarian. (56m7s)
• There is a growing competition between human workers and AI, with the possibility of AI taking over certain jobs in the future. This creates a greater urgency for human workers to differentiate themselves. (56m51s)
• The importance of personal branding and taking a methodical approach to job searching is emphasized. Building relationships with potential employers can lead to more satisfying and successful job placements. (57m51s)
• The discussion touches on the future of work and the potential for AI to replace many jobs, with a focus on how workforce reduction should ideally improve human experiences. (59m8s)
• The goal is to apply AI in a responsible and ethical way to tackle important questions and problems, such as finding cancer at early stages, rather than just creating art that a designer could have created (59m24s).
• There are enough people in tech who see the upside of applying technologies in a responsible way and are working to grow humanity, create more jobs, and use AI for the betterment of all (59m40s).
• A company like GitHub is working on announcements that can have an impact and improve people's lives, focusing on quality of life and making a positive difference (1h0m21s).
• The approach to technology is shifting from cost reduction and making money to actually impacting humanity by applying technologies in a way that makes sense (1h0m47s).
• The accessibility of technology is increasing, with devices and computers becoming more available to people, especially the youth, which is a positive trend (1h0m56s).
• New generations coming into tech are valuing their mental health and well-being, thinking about their families, and moving away from the "grind and die" stage that plagued previous generations (1h1m28s).
• There is a growing understanding that technology does not automatically lead to positive change, and that thoughtful and ethical people need to follow up and address potential harm caused by new technologies (1h2m11s).
• The importance of being aware of the potential consequences of building the future and making sure it is a safe one is emphasized (1h2m49s).

Encouragement, Future of Tech, and Jason Shen's Work

• A shout-out is given to future entrepreneurs with amazing ideas that can benefit humanity, encouraging them to go for it and make a positive impact (1h2m56s).
• The discussion highlights the current era as an interesting and transformative time in the tech industry, suggesting that in 20 years, the changes being experienced now will be seen as commonplace. (1h3m9s)
• Jason Shen is actively engaged in writing and coaching, transforming his coaching sessions into valuable content for his newsletter, which targets entrepreneurs and outliers. (1h4m40s)
• The newsletter covers topics such as finding conviction, facing doubt, attending conferences, writing books, and dealing with ADHD. (1h5m3s)
• The conversation emphasizes the importance of sharing knowledge and providing access to those who may not have the means to hire a coach, thus acting as a multiplier of information. (1h5m25s)

Conclusion and Call to Action

• The session concludes with appreciation for the engaging conversation and a note on the importance of having a comprehensive skill set in today's world, beyond just technical abilities. (1h6m12s)
• Appreciation is expressed to the audience for their engagement and to Jennifer, Baram, Tiffany, Isaac, and Jason for their participation in the event (1h6m38s).
• It is recommended that anyone building something should build it on GitHub, utilizing the link shared on the screen, which offers opportunities such as credits and developer tools to scale and grow a company (1h7m0s).
• The GitHub program is completely free to join and offers a network of founders and entrepreneurs who have been successful in the past (1h7m36s).
• An upcoming event, GitHub Universe, is mentioned, which will feature keynotes, sessions, and announcements, and attendees are encouraged to join either in person or virtually (1h7m50s).
• The host expresses their excitement for the event and invites attendees to say hello if they see them in person (1h8m24s).
• Congratulations are given to Brian from Nextera Energy, who won the Swip stick giveaway ticket (1h8m35s).
• A personal anecdote is shared about attending GitHub Universe for the first time in person and being invited to speak on a panel discussion, describing the event as having a casual and welcoming feel (1h9m15s).
• The speaker expresses gratitude for the opportunity to speak at the event and is looking forward to exploring new sessions and learning from other speakers (1h9m47s).
• The speaker praises the coaching and organization of the event, noting that it is more community-driven and less corporate compared to other conferences they have spoken at (1h10m6s).
• The experience has been approachable, and the person feels approachable too (1h10m28s)
• The person has really enjoyed the experience so far (1h10m32s)