Bitcoin Boom Exposes Chamath’s $4B Mistake

• Bitcoin continues riding high on the Trump Pump.
• Chamath Palihapitiya reveals multi-billion dollar regret.
• Retail investors are back.

Bitcoin has been on a tear since Donald Trump’s November 6 election win, soaring 35% to hit a record $93,300 last week. Now steady near $90,000, the rally has reignited mainstream interest, fueling speculation that the momentum is far from over.

Amid the market euphoria, Social Capital co-founder Chamath Palihapitiya admitted to a costly mistake. He revealed he sold his Bitcoin far too early, a decision he now estimates cost him billions.

Bitcoin Regrets

Bitcoin sentiment is riding high, fueled by Trump’s pledge to make the US the global crypto capital . The resulting tailwind has propelled BTC to successive all-time highs since his election win earlier this month, with prices now eyeing a $93,300 retest.

With market confidence soaring, Palihapitiya reflected on his costly decision to sell early. Speaking on the latest All In One podcast, the venture capitalist shared how his partners’ unease with Bitcoin led him to offload the company’s holdings “to be a good team member.”

While Palihapitiya acknowledged that the sale was profitable then, he now estimates the missed upside at today’s soaring prices to be a staggering $3–$4 billion.

Palihapitiya disclosed that part of the proceeds went toward purchasing land in Lake Tahoe. A 2021 tweet about the purchase revealed his lingering regret over exiting Bitcoin, even at 2021 prices. The tweet also confirmed that the sell-off occurred in 2014.

In 2014, Bitcoin traded between $260 and $1,000, starting the year at its peak before entering a prolonged downtrend.

Retail Investors Return

Fast forward to now, and Bitcoin has been in a macro bull phase since Q4 2023. But despite that, casual retail investors had largely stayed on the sidelines , until now.

Signs of a retail resurgence were already emerging in October, even before Trump’s election victory. On-chain data showed a rise in Bitcoin transactions under $10,000 , hinting at smaller investors reentering the market.

With BTC now at record levels, Google searches for Bitcoin are projected to hit 43 by the end of November, surpassing March’s peak of 40 during the $74,000 rally, fueled by ETF mania.

In line with the Trump Pump, all signs point to a resurgence of mainstream interest, which will draw retail traders back into the market.

On the Flipside

• Mt. Gox filed for bankruptcy in 2014, prompting doubts about BTC and cryptocurrency in general.
• Downside volatility risk remains, even during macro bull moves.
• Social Capital co-founders Mamoon Hamid and Ted Maidenberg left the firm in 2017 amid hostile conditions.

Why This Matters

Palihapitiya’s $4 billion Bitcoin regret is a humbling reminder that even sophisticated investors can misread history-making innovations.

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