Tesla, Uber Could Triple In 5 Years? Elon Musk Ally Jason Calacanis Says Both Stocks Are ‘50% Undervalued’

• He expects ride-sharing’s share of rides to grow from about 1% to 30% within his lifetime, benefiting both companies.
• Uber reported $59.8 billion in quarterly gross bookings and $2.54 billion in free cash flow, although fuel costs and driver shortages weighed on Mobility growth.
• Uber targets more than 2,000 driverless vehicles by the end of 2027, while Tesla reported nearly 2 million cumulative unsupervised robotaxi miles through September.

Early Uber investor and Elon Musk ally Jason Calacanis said Tesla (TSLA) and Uber Technologies (UBER) are 50% undervalued and predicted both stocks would triple in under five years as ride-sharing expands.

TSLA, UBER Lead Calacanis’ Bets On Ride-Sharing Boom

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Calacanis, who is also an All-In podcast co-host, praised Uber’s latest quarterly results and named it a top pick alongside Tesla. The call follows his $1 million in purchases of each stock last month.

“Demand, growth, free cash flow and a strong position in the emerging AVs market make this my number one pick alongside $tsla right now,” he said on X. He expects ride-sharing’s share of rides to rise from about 1% to 30% within his lifetime, creating opportunities for both companies. Calacanis predicted both stocks would triple in under five years, calling them as “50% undervalued.” 

His latest forecast follows a separate bet on autonomous vehicle takeovers. In September, Calacanis disclosed small positions in WeRide (WRD), Pony.ai (PONY), Lucid (LCID) and Rivian (RIVN), predicting that all four would be acquired within 24 months.

“Consolidation is coming to the autonomous space based on the massive progress that Tesla, Waymo, and Uber are making,” he said at the time. “I believe these four companies are going to be bought in the next 24 months and I expect, as a group, that I will 2x my investment in under two years.”

He called those smaller positions as investments with a one-to-four-year horizon, compared with his usual intention to hold equities for more than a decade. 

Calacanis Puts His Money Behind Forecast

Calacanis backed his bullish bet with sizable purchases. Late last month, he disclosed buying 15,000 Uber shares at $65 for $975,000 and 3,000 Tesla shares at $357 for about $1.07 million.

His 12-month targets favored Uber: $120 implied 85% upside from his entry price, while Tesla’s $500 target pointed to about 40%. A $189,000 Netflix (NFLX) purchase brought the three trades to $2.24 million. 

Calacanis also sees room for both Uber and Tesla in autonomous driving. When asked whether Tesla’s robotaxi push threatened Uber, he predicted Tesla would capture 40% of the market, Uber and its partners 35%, and Alphabet’s Waymo 15%. Still, his enthusiasm depends on the price. “If Uber was at $100, I wouldn’t make this trade,” he said.

Uber And Tesla Accelerate Robotaxi Plans

Uber’s latest results showed strong demand and cash generation. Third-quarter gross bookings rose 20% year over year to $59.8 billion, while revenue climbed 10% to $14.77 billion. Free cash flow reached $2.54 billion for the quarter and a record $10.4 billion over the preceding 12 months.

Growth still faced hurdles. Higher fuel prices and driver shortages left Mobility growth one to two percentage points below the company’s expectations.

Uber is also expanding its driverless fleet, targeting about 700 vehicles on its platform by year-end and more than 2,000 by the end of 2027. It plans to launch a driverless Nuro-Lucid service in the Bay Area in early 2027, followed by supervised Rivian deployments in 2028 before moving to fully driverless operations.

Meanwhile, Tesla is advancing its own service. The company said Cybercab rides began in Austin on September 3, with its robotaxi fleet reaching nearly 2 million cumulative unsupervised miles by the end of the third quarter.

Calacanis Backs A Decade Of Tech Gains

Beyond Tesla and Uber, Calacanis said he currently holds Netflix (NFLX), Amazon (AMZN), Alphabet (GOOG), Meta Platforms (META), Robinhood (HOOD), Nvidia (NVDA), Microsoft (MSFT), Apple (AAPL), Shopify (SHOP) and SpaceX (SPCX).

“I will keep adding to these franchises and (mostly) consistent compounders due to their investments in the future, exceptional products and strong leadership,” he said. He expects these core holdings to deliver returns several times those of the index over the next decade. He also holds about 10 smaller speculative positions, which he would cut if their products and business fundamentals stopped improving.

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