Jun 20, 2022, 12:06 PM ETInterview, Fireside Chat

Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899

Gary Vaynerchuk began investing at age 32 in 2007, initially unaware of angel investing despite working in his father's liquor store with limited personal capital.
His first equity acquisition was a purchase of Twitter shares from founding CTO Blaine Cook for an undisclosed sum after Blaine sought to exit the company.
He subsequently invested in Facebook with a six-figure check that nearly depleted his savings, facilitated by Randy Zuckerberg following his connection to Mark Yudkin (his lawyer and current COO/GC).
Vaynerchuk's third major early investment was in Tumblr by David Karp; he notes that Facebook remains his sole holding from that era, while he retains the majority of his Twitter equity.
He describes the strategy as a calculated deployment of accumulated savings from his 20s rather than a result of luck, emphasizing 10 years of diligence in identifying high-potential Web 2.0 companies.

Vaynerchuk attributes his presence in the United States to "luck," citing the geopolitical shift in 1978 that allowed Jewish families to emigrate from the Soviet Union to Israel and eventually the US.
He argues that while birth circumstances are luck, his ability to recognize and act on opportunities (such as attending SXSW and meeting Facebook/Twitter founders) resulted from deliberate effort and curiosity.
He defines luck as a binary concept where success is a mix of "deciding what you want to say and do" combined with the external gifts one is given.

A defining hardship occurred between ages 22 and 29 when Vaynerchuk grew his father's liquor store revenue from $3.8 million to $60 million without receiving equity or commensurate compensation.
His father refused to grant him equity, stating he would "get it when I die," which led to friction regarding the business's future and the father's delayed retirement.
Vaynerchuk observed his father suffering from a loss of identity, described by the Russian term "senator with an empty briefcase," where the father was no longer the decision-maker despite being the legal owner.
The lesson learned from this conflict was that "business doesn't mean shit; family, life, and happiness" take precedence, leading him to build his own infrastructure to move forward independently.
In 2009, at age 34, he founded VaynerMedia with no capital, starting in a coworking space at Buddy Media's conference room.

Vaynerchuk admits to having deep-seated insecurities in non-business contexts, specifically stating a "fear of reading out loud" despite being comfortable giving keynotes to billions of viewers.
He asserts that his public persona of absolute confidence in business is accurate because he lacks self-doubt in that arena, comparing his 17-year-old self to Kobe Bryant's mindset of having "no doubt."
He rejects the notion of a "chasm" between public and private selves, claiming he is consistent, though his energy levels and specific interests shift between professional leadership and family life.
He views fame and wealth as accelerants that expose an individual's true character, noting that his college friends confirmed he remains the same person despite his success.

Vaynerchuk's approach to online hate involves starting with humility and assessing if the criticism holds 2% of truth, followed by compassion for the critic's unhappiness.
He rejects the idea that wealth caused his mindset, arguing instead that his confidence and "practical optimistic" framework were established before he had money, specifically when he was content earning $48,000 a year at age 25.
He identifies as a "practical optimist," avoiding delusion while maintaining the conviction that problems can be solved through action rather than despair.
He advises listeners to consume positivity, noting that "what one consumes is who they become," and emphasizes that 86% of people are positive toward him.

Vaynerchuk maintains high performance without burnout by judging success over a "99-year life" horizon rather than weekly or yearly short-term metrics.
He does not feel he "gave up" time with family or leisure because he views those activities as integral to a long-term life strategy, not as sacrifices of career progress.
He states he will continue working as long as it brings him joy, explicitly rejecting a scenario where he would receive $100 billion in exchange for complete retirement, citing a belief that work is essential to his identity.
He compares his potential loss of identity without work to an elderly person dying of a broken heart after a spouse passes, framing entrepreneurship as a "great hobby" and essential life force.

Vaynerchuk recently changed his mind regarding Facebook's content strategy, re-engaging with the platform following the iOS 14 update which shifted supply and demand of attention back toward native video.
He cites "being exceedingly liked by the vast majority of people he has ever interacted with" as his greatest accomplishment in life.
His five-year forward-looking goal is to remain in his current position: healthy, free from anxiety regarding family well-being, and fully engaged in daily professional activities of his choice.
He defines his ideal future state as being the "captain of the ship," capable of navigating storms and enjoying sunny days on his own terms.