#790: Chris Sacca — How to Succeed by Living on Your Own Terms and Getting Into Good Trouble

Chris Sacca, a prominent investor and entrepreneur, has shared detailed accounts of his upbringing in upstate New York and early business endeavors that contributed to his current success.

Chris Sacca Witnessed Manufacturing Decline and Community Impact in Upstate New York

Growing up in Lockport, New York, Sacca witnessed firsthand the devastating impacts of manufacturing decline. The closure of a GM plant, which once produced radiators and air conditioners, led to widespread job loss. Former workers were relegated to low-paying positions, such as Walmart greeters, and Sacca notes the resulting economic downturn contributed to the town becoming home to the largest trailer park in the Northeast, escalating drug issues, and increased MAGA sentiment.

As a Child, Sacca's Entrepreneurial Hustles, Such as Trading Commodities, Running a Card Room, and Selling Blow Pops and Sports Bets, Shaped His Perspective on Real-World Experience and Resourcefulness

From a young age, Sacca engaged in a variety of entrepreneurial activities. He sold everyday items like walnuts and rocks as air fresheners and collectibles in his neighborhood. Alongside these smaller endeavors, Sacca had a knack for running businesses on the side, illustrating a persistent entrepreneurial spirit.

Sacca's Early Experiences Built Work Ethic, Risk-Taking, and Negotiation Skills Essential for Success Today

Sacca’s work ethic and willingness to take risks were honed early. By the age of 13 or 14, he traded commodities like live hogs and frozen orange juice concentrate. Using a pager connected to the Chicago Board of Trade, he utilized technical analysis, seasonality, and chart pattern anomalies to inform his trades. His father's friend gave him an account to trade these commodities, agreeing to split profits while covering losses, giving Sacca an early taste of venture capital.

Sacca also ran a card room during his school years, which provided him with additional income and experience in business operations. ...

Chris Sacca, reflecting on changing childhood experiences, notes that today's youth may be missing out on critical life lessons due to overprotection and surveillance.

Sacca Believes Today's Youth Are Shielded From Mistakes, Adversity, and Learning

Sacca attributes the inability of a generation of young people to detect deceit to overprotective parenting that often prevents young people from encountering situations where they have to discern lies or confront adversity. He expresses concern that kids these days haven't been given the chance to make mistakes, partially due to technologies like Ring cameras that constantly surveil environments.

Flaws and Mistakes Build Character and Resilience

Sacca comments that young people today do not seem to have many experiences that help them build character and resilience through regrettable actions or by having to bluff their way in or out of circumstances. He suggests that these types of experiences are what help individuals develop resourcefulness and survival skills. He laments the lack of opportunities youth have today to engage in the kind of deviant or risky activities that contribute to personal growth.

Sacca Laments Limited Opportunities For Youth to Engage In Deviant or Risky Activities

Sacca points out that formative experiences, such as engaging in minor transgressions, can teach valuable life skills that are beneficial later in life.

Key Experiences For Developing Modern Skills

He observes that his daughters were innocently playing beer pong with soda at a tailgate party and notes the skill-building aspect of such games, which he suggests are lessons not often taug ...

Chris Sacca delves into the profound impact of artificial intelligence (AI) and automation on the workforce, challenging traditional concepts of work, and the future of societal structures.

Sacca on AI and Automation Displacing Workforce

Sacca raises alarms that AI's rapid advancements are outstripping the capacity for human adaptation.

Technologies Outpace Adaptation, Causing Job Insecurity and Social Unrest

Sacca explains that traditional jobs are disappearing at an alarming rate. He cites that his firm requires significantly fewer lawyers due to AI's efficiency in drafting legal documents. Further, he describes AI's capabilities in coding that have rendered nearly all coding jobs, except for high-level computer science, obsolete. Sacca also warns that the outsourcing of jobs, weakening of unions, and the impact of large corporations have disrupted the social contract for the blue-collar working class. He cautions that white-collar workers are now experiencing a similar fate as AI rapidly takes over their roles, leading to job insecurity.

Sacca criticizes the tech industry's myopic perspective on the conflict between job displacement and the optimistic promise of AI. Recalling Vinod Khosla's TED talk, Sacca notes that while Khosla acknowledges the job-displacing potential of AI, his quick pivot to suggest wealth redistribution overlooks the complexities of such a solution. Sacca remarks that no society has ever successfully redistributed wealth and implies that this does not address the crisis fully.

Addressing the human element, Sacca wonders what exceptional human abilities are left that machines can't replicate and predicts massive job losses due to automation and AI, such as massage robots performing more massages than humans without health drawbacks. He worries about the social safety net's inadequacy and whether institutions are ready for the displacement caused by AI and automation. Reflecting on a personal encounter with a Waymo self-driving car, Sacca ponders its existential threat to the professional drivers who have built their own businesses.

Sacca also questions what children should be taught when tools like ChatGPT can complete assignments more efficiently than a sixth-grader.

Sacca Thinks AI and Automation May Reduce the Relevance of Traditional Career Pathways Like Education and Training

Sacca expresses doubt about the relevance of traditional education and training in light of advancements in AI and automation. He questions the value of teaching skills such as accounting or writing marketing copy when AI can ...

In a digital world that increasingly prioritizes connectivity through screens, Chris Sacca emphasizes the singular value of in-person community interactions and immersive analog experiences.

Sacca Values In-person Interactions, Community, and Analog Experiences, Rare in a Digital World

Chris Sacca champions the restorative power of community by sharing personal stories that underscore the impact of tangible, in-person experiences. He speaks passionately about the value his daughter derived from attending a forest preschool, which prioritizes play-based learning and interaction with nature over a traditional academic setting. Sacca believes in engaging with the physical world, as demonstrated by his preference for facilitating challenging conversations in "dirty bars" or visiting a cattle ranch to interact with people outside of one's usual circle.

Sacca's Vision: Developing Spaces For Connection, Collaboration, and Appreciation of Analog Imperfections

Sacca is determined to create and invest in spaces that encourage connection and collaboration. He imagines ventures like a landlocked yacht club and a mini-golf country club as community-centric spaces that invite social interaction. Furthermore, he envisions multipurpose warehouse spaces that might function as offices, art spaces, or community hubs—places inherently designed for in-person experiences and communal engagement.

Investing In Community Initiatives Mitigates Societal Impacts of Tech Advancement and Loss of Shared Experiences

Sacca emphasizes the significance of analog experiences, appreciating the meticulous craftsmanship of Japanese pottery, the personal touch in exploring a city through its locals, and the camaraderie felt at Montana State University football games. Digital interactions can be exhaus ...

Chris Sacca is working on a new project titled "No Permanent Record," which seeks to delve into the messy and unpredictable nature of human experience, emphasizing resilience, resourcefulness, and the importance of learning from missteps.

Sacca's "No Permanent Record" Project Celebrates Entrepreneurs' Formative Experiences and Missteps

The project is about having conversations with successful individuals where they discuss smaller offenses they've committed, parties they've thrown, lies they've told, and challenges they've overcome. Sacca is keen on recording these adventurous and sometimes risky autobiographical snippets. He wants to memorialize the stories of people's experiences, their hijinks, and their craftiness, for the benefit of humanity before societal structures potentially become obsolete.

Inspiring Stories of Resilience and Resourcefulness for the Next Generation

Sacca recalls how past experiences, such as navigating situations without adult guidance or conveniences, taught resilience and resourcefulness. He critiques the current generation's lack of such experiences, suggesting their significance for handling an uncertain future. Sacca's anecdotes reveal an aim of teaching skills beyond traditional academics, such as card tricks or the art of negotiation—skills that he deems important in fostering adaptability.

Goal: Celebrate the Messiness and Unpredictability of Human Experience, Contrasting Societal Pressure For Perfection and Fear of Mistakes

Sacca believes that it's necessary to fill a "massive cultural hole" that has been created by societal pressures for perfection and stigmas around having a record of mistakes. He argues for a shift that values learning from adversity, risk-taking, and overcoming challenges. By discussing how past generations managed without constant oversight and by presenting stories of formative, imperfect experiences, Sacca's project aims to inspire a culture that appreciates the rough and tumble aspects of life.

Sacca Aims to Inspire Appreciation For Adversity, Risk-Taking, and Learning From Mistakes to Navigate an Uncertain ...