Jimmy Douglas is the solo founder and CEO of Plug, a marketplace for used EVs that just raised a $20M Series A led by Lightspeed. Before Plug, he spent five years at Tesla, where he ran the used-car business. At the time, it was the largest used-EV operation in the world.

When the Inflation Reduction Act hit in 2023 and EV leasing skyrocketed, Jimmy gave himself three years to be in the right place at the right time. He'd watched the secondary EV market up close from inside Tesla, and the infrastructure was woefully inefficient. A dealership will sit on a used Honda Accord for 60 days. Sit on a used Tesla Model S for 60 days during that era, and you'd lose $10,000 to volatility. Most dealers were opting out. A handful were arbitraging. Meanwhile, the volume coming was massive. He left to build for the wave.

Two years into Plug, the business was generating revenue but nowhere near venture scale. The model was right; the go-to-market wasn't. He recently asked Claude to dig through his emails, board decks, and investor updates and count how many go-to-market pivots they tried before one started growing like a hockey stick. The answer was 14. Ten of them grew. Only one grew fast enough.

His regret from those early days isn't the pivots. It's how long he waited to do the very first transaction. Plug's first deal was a Tesla Model 3, ten dealers bidding, over 100 bids. They lost $3,000 on the sale, but it was worth it to see how real users would transact.

Solo, together.

Julian

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