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Jun 20, 2022 · 32m · news

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

Gary Vaynerchuk · 24m spoken Harry Stebbings · 3m spoken
0:00 / 0:00
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of 20VC, Harry Stebbings interviews entrepreneur Gary Vaynerchuk about his early angel investments, his immigrant roots, and his philosophies on managing family dynamics, online criticism, and long-term ambition.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 11.2% of the talking time here. How this is scored →

Harry as informed peer 3.0 Guest teaching 6.2 Guest disagreement 2.6 Harry pushing back 2.8
05100:0010:0020:0030:000:08–4:02 · Harry as informed peer 1/10 Gary Vee's First Three Angel Investments The host asks a simple open-ended question to kick off the interview about Gary's entry into tech investing. Gary monologues at length, detailing his early deals in Twitter, Facebook, and Tumblr without host interruption.4:02–7:42 · Harry as informed peer 3/10 The Role of Luck in Success Harry introduces a quote from previous guest Chris Sacca to prompt Gary on the role of luck versus strategy. Gary reframes luck through his Soviet immigrant origin story and educates the host on the historical context of Soviet Jewish emigration.7:42–19:01 · Harry as informed peer 4/10 Family Friction, Self-Doubt, and Authenticity Harry demonstrates strong background preparation by noting he listened to prior interviews, prompting Gary to share unprecedented details about his family business conflict. Harry gently probes Gary's lack of self-doubt and tests whether his unshakeable confidence ever caused trouble.19:01–24:21 · Harry as informed peer 3/10 Ego, Self-Esteem, and Handling Online Hate Harry challenges Gary on identity chasm and ego, opening up about receiving hurtful DMs and death threats. Gary takes on an educational, almost therapeutic role, instructing Harry on how to process hate through humility and empathy.24:21–30:27 · Harry as informed peer 4/10 Long-Term Ambition and a Passion for Work Harry pushes back on Gary's long-term patience, asking if it is merely a privilege enabled by current financial success. Gary passionately rejects the premise, explaining that his mindset was present when he made low wages in his twenties.0:08–4:02 · Guest teaching 5/10 Gary Vee's First Three Angel Investments The host asks a simple open-ended question to kick off the interview about Gary's entry into tech investing. Gary monologues at length, detailing his early deals in Twitter, Facebook, and Tumblr without host interruption.4:02–7:42 · Guest teaching 6/10 The Role of Luck in Success Harry introduces a quote from previous guest Chris Sacca to prompt Gary on the role of luck versus strategy. Gary reframes luck through his Soviet immigrant origin story and educates the host on the historical context of Soviet Jewish emigration.7:42–19:01 · Guest teaching 6/10 Family Friction, Self-Doubt, and Authenticity Harry demonstrates strong background preparation by noting he listened to prior interviews, prompting Gary to share unprecedented details about his family business conflict. Harry gently probes Gary's lack of self-doubt and tests whether his unshakeable confidence ever caused trouble.19:01–24:21 · Guest teaching 7/10 Ego, Self-Esteem, and Handling Online Hate Harry challenges Gary on identity chasm and ego, opening up about receiving hurtful DMs and death threats. Gary takes on an educational, almost therapeutic role, instructing Harry on how to process hate through humility and empathy.24:21–30:27 · Guest teaching 7/10 Long-Term Ambition and a Passion for Work Harry pushes back on Gary's long-term patience, asking if it is merely a privilege enabled by current financial success. Gary passionately rejects the premise, explaining that his mindset was present when he made low wages in his twenties.0:08–4:02 · Guest disagreement 1/10 Gary Vee's First Three Angel Investments The host asks a simple open-ended question to kick off the interview about Gary's entry into tech investing. Gary monologues at length, detailing his early deals in Twitter, Facebook, and Tumblr without host interruption.4:02–7:42 · Guest disagreement 2/10 The Role of Luck in Success Harry introduces a quote from previous guest Chris Sacca to prompt Gary on the role of luck versus strategy. Gary reframes luck through his Soviet immigrant origin story and educates the host on the historical context of Soviet Jewish emigration.7:42–19:01 · Guest disagreement 2/10 Family Friction, Self-Doubt, and Authenticity Harry demonstrates strong background preparation by noting he listened to prior interviews, prompting Gary to share unprecedented details about his family business conflict. Harry gently probes Gary's lack of self-doubt and tests whether his unshakeable confidence ever caused trouble.19:01–24:21 · Guest disagreement 3/10 Ego, Self-Esteem, and Handling Online Hate Harry challenges Gary on identity chasm and ego, opening up about receiving hurtful DMs and death threats. Gary takes on an educational, almost therapeutic role, instructing Harry on how to process hate through humility and empathy.24:21–30:27 · Guest disagreement 5/10 Long-Term Ambition and a Passion for Work Harry pushes back on Gary's long-term patience, asking if it is merely a privilege enabled by current financial success. Gary passionately rejects the premise, explaining that his mindset was present when he made low wages in his twenties.0:08–4:02 · Harry pushing back 0/10 Gary Vee's First Three Angel Investments The host asks a simple open-ended question to kick off the interview about Gary's entry into tech investing. Gary monologues at length, detailing his early deals in Twitter, Facebook, and Tumblr without host interruption.4:02–7:42 · Harry pushing back 2/10 The Role of Luck in Success Harry introduces a quote from previous guest Chris Sacca to prompt Gary on the role of luck versus strategy. Gary reframes luck through his Soviet immigrant origin story and educates the host on the historical context of Soviet Jewish emigration.7:42–19:01 · Harry pushing back 3/10 Family Friction, Self-Doubt, and Authenticity Harry demonstrates strong background preparation by noting he listened to prior interviews, prompting Gary to share unprecedented details about his family business conflict. Harry gently probes Gary's lack of self-doubt and tests whether his unshakeable confidence ever caused trouble.19:01–24:21 · Harry pushing back 4/10 Ego, Self-Esteem, and Handling Online Hate Harry challenges Gary on identity chasm and ego, opening up about receiving hurtful DMs and death threats. Gary takes on an educational, almost therapeutic role, instructing Harry on how to process hate through humility and empathy.24:21–30:27 · Harry pushing back 5/10 Long-Term Ambition and a Passion for Work Harry pushes back on Gary's long-term patience, asking if it is merely a privilege enabled by current financial success. Gary passionately rejects the premise, explaining that his mindset was present when he made low wages in his twenties.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 11.9% · guest 88.1%0:00 · Harry 11.9% · guest 88.1%3:00 · Harry 8.6% · guest 91.4%3:00 · Harry 8.6% · guest 91.4%6:00 · Harry 13.2% · guest 86.8%6:00 · Harry 13.2% · guest 86.8%9:00 · Harry 0% · guest 100%9:00 · Harry 0% · guest 100%12:00 · Harry 15.2% · guest 84.8%12:00 · Harry 15.2% · guest 84.8%15:00 · Harry 12.4% · guest 87.6%15:00 · Harry 12.4% · guest 87.6%18:00 · Harry 8.2% · guest 91.8%18:00 · Harry 8.2% · guest 91.8%21:00 · Harry 14.2% · guest 85.8%21:00 · Harry 14.2% · guest 85.8%24:00 · Harry 14.7% · guest 85.3%24:00 · Harry 14.7% · guest 85.3%27:00 · Harry 8.4% · guest 91.6%27:00 · Harry 8.4% · guest 91.6%30:00 · Harry 19% · guest 81%30:00 · Harry 19% · guest 81%
Sharpest disagreement ▶ 26:00 Gary forcefully rejects Harry's premise on financial privilege

When Harry suggests Gary's long-term patience is a product of existing wealth, Gary firmly interrupts with 'No, it's the reverse! Listen back to the interview,' aggressively defending his origin story.

 Hardest push from Harry ▶ 25:55 Harry questions if Gary's philosophy is enabled by accumulated wealth

Harry refuses to accept Gary's smooth framing of long-term patience without challenging whether financial security makes that mindset vastly easier to hold.

 Biggest teaching moment ▶ 22:22 Gary reframes online hate and teaches emotional management

Gary breaks down Harry's emotional reaction to DMs, teaching him to filter hate through self-auditing for truth and expressing pity for online trolls.

 Harry holds his own ▶ 25:55 Harry calls out the potential survivorship bias in Gary's mindset

Harry shows sharp analytical expertise by probing whether Gary's macro patience is only feasible after achieving immense wealth and financial freedom.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Gary Vee's First Three Angel Investments 1510 The host asks a simple open-ended question to kick off the interview about Gary's entry into tech investing. Gary monologues at length, detailing his early deals in Twitter, Facebook, and Tumblr without host interruption.
The Role of Luck in Success 3622 Harry introduces a quote from previous guest Chris Sacca to prompt Gary on the role of luck versus strategy. Gary reframes luck through his Soviet immigrant origin story and educates the host on the historical context of Soviet Jewish emigration.
Family Friction, Self-Doubt, and Authenticity 4623 Harry demonstrates strong background preparation by noting he listened to prior interviews, prompting Gary to share unprecedented details about his family business conflict. Harry gently probes Gary's lack of self-doubt and tests whether his unshakeable confidence ever caused trouble.
Ego, Self-Esteem, and Handling Online Hate 3734 Harry challenges Gary on identity chasm and ego, opening up about receiving hurtful DMs and death threats. Gary takes on an educational, almost therapeutic role, instructing Harry on how to process hate through humility and empathy.
Long-Term Ambition and a Passion for Work 4755 Harry pushes back on Gary's long-term patience, asking if it is merely a privilege enabled by current financial success. Gary passionately rejects the premise, explaining that his mindset was present when he made low wages in his twenties.

Statements from this episode (10)

Disclosure
Gary Vee's first three angel investments were Facebook, Twitter, and Tumblr
“The first three companies I invested in, in my entire life as an investor were Facebook, Twitter, and Tumblr.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:22
Disclosure
Gary Vee has never sold a single share of his Facebook stock
“I've never sold a share of Facebook since the day I invested almost 15 years ago.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:35
Disclosure
Gary Vee still holds the majority of his original Twitter investment
“I sold some Twitter, but still hold the majority of that holdings from then.”
Gary Vaynerchuk Jun 20, 2022 ▶ 3:41
Assertion Not checkable as stated
Gary Vee invested his entire 20s savings into Facebook, Twitter, and Tumblr
“Saving my money in my twenties And then deciding to spend all of it in a one year period on Facebook, Twitter, and Tumblr based on at that .10 years of very hard work, diligence of saving and not wasting my money and looking for the opportunity to strike.”
Gary Vaynerchuk Jun 20, 2022 ▶ 6:42
Assertion Not publicly verifiable
Gary Vee scaled his father's wine business to $60M on under $100k
“My dad had a business doing 3.8 million in revenue. And in a seven year window, I took it to sixty million. And I changed the course of my father's financial life and my mother's financial life. Yet I was never getting paid a 100,000 dollars a year and owned n…”
Gary Vaynerchuk Jun 20, 2022 ▶ 8:02
Assertion Not checkable as stated
Gary Vee started VaynerMedia at 34 with zero cash in a boardroom
“At 34 years old, I started VaynerMedia with no money. We started the company in Buddy Media's conference room, which I'm sure you know, because you've listened to another interviews, and I'm very proud of what we've built from zero and scratch with no cash”
Gary Vaynerchuk Jun 20, 2022 ▶ 12:23
Insight
Gary Vee argues money and fame expose character rather than change it
“All that money and fame do, Harry, is exposes who you actually are. It just accelerates your truth.”
Gary Vaynerchuk Jun 20, 2022 ▶ 20:48
Insight
Gary Vee admits his content is more therapy than traditional business advice
“My content is far more therapy than it is business HBS.”
Gary Vaynerchuk Jun 20, 2022 ▶ 21:08
Disclosure
Gary Vee would refuse $100 billion if forced to permanently retire
“If somebody came to me and said, I will give you one hundred billion dollars in cash, but you can never work again. You must fully retire, meaning the cliche thing, must go on a beach, In a very nice place and actually do nothing besides drink beers, walk on t…”
Gary Vaynerchuk Jun 20, 2022 ▶ 28:47
Assertion Partly supported
Gary Vee says post-iOS 14 ad pullbacks created organic arbitrage on Facebook
“I changed my mind on how big of a platform Facebook is. One of the coolest things for me right now is that I'm back into being obsessed with content on Facebook because the map of supply and demand of attention on it has flipped aggressively with iOS, 14 updat…”
Gary Vaynerchuk Jun 20, 2022 ▶ 30:39

Shorts cut from this episode

▶ Gary Vee's mindset advice for you 🗣️ · 20VC with Harry Steb (@21:33) ▶ Gary Vee: Don’t sleep on this social network · 20VC with Har (@30:34) ▶ Gary Vee is bullish on Facebook 😲 · 20VC with Harry Stebbin (@30:34) ▶ Gary Vee: Why I think Facebook is underrated · 20VC with Har (@30:34) ▶ Gary Vee keeps it real · 20VC with Harry Stebbings (@28:47) ▶ Stop telling yourself you suck · 20VC with Harry Stebbings (@21:33) ▶ Gary Vee: The ONE THING I love the most · 20VC with Harry St (@30:06) ▶ Gary Vee reveals his secret to success · 20VC with Harry Ste (@27:28) ▶ Gary Vee's biggest fear · 20VC with Harry Stebbings (@15:26) ▶ How has MONEY and FAME changed Gary Vee · 20VC with Harry St (@19:41)
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