Inside the fundraising playbook of the serial entrepreneur who’s done 3,000 pitches, raised $3 billion, and sold his startups to Amazon and Walmart in monster acquisitions 

Marc Lore is many things, as I wrote in this deep and revealing profile of him for Fortune’s latest print issue. He’s a serial entrepreneur – having co-founded Diapers.com, Jet.com and Wonder – who channeled a traumatic childhood into insatiable ambition.

He’s a founder who has sold two of those startups to Amazon and Walmart for nearly $4 billion combined, but still believes he has so much left to prove.

And he’s a big thinker with a knack for pursuing low-probability ideas with high-speed zeal no matter the haters. Oh, he’s a co-owner of the Minnesota Timberwolves NBA franchise too.

But among his supporters and detractors alike, he might be best known as a world-class fundraiser. In several cases, when his startups have seemingly hit dead-ends, he’s miraculously found a path to another cash infusion when it shouldn’t have been possible. 

Lore has raised more than $3 billion in venture funding across 15 fundraising rounds during his career, despite being rejected approximately 2,800 out of 3,000 times, by his own calculation—or 93% of the time. 

Liza Landsman, who worked for Lore as a top executive at Jet.com, described her former boss’ startup pitching prowess this way in my 2023 book Winner Sells All.

“My grandmother had a saying, roughly translated from Yiddish: ‘People who could talk clouds out of the sky,’” she had said. “And I always thought this about Marc.”

So what’s Lore’s fundraising strategy? He unpacked it in one of my recent sit-downs with him. 

His playbook starts by filling the pipeline – taking every possible investor meeting. Everyone’s money is green.

When the answer is no, Lore probes for the specific reason, accepts the feedback, tweaks the presentation accordingly, and persuades the investor to sit for another, more targeted pitch. 

Five of 25 investors for his current venture Wonder initially declined, then ended up investing anyway, Lore told me proudly. “Twenty percent of our investors had literally passed,” he said, emphasizing the final word. “I don’t mean on a previous round; I mean on that round.”

As for the content of the actual pitches, Lore believes less is often more.

“I try to always narrow it down to, ‘What’s the one thing that if we accomplish it, the idea works?’ ” Lore said. “The thing that, if it works and you believe in this, then it’s gonna be a monster.” 

“It’s limiting the number of things that [investors] have to believe,” he added.
This playbook has worked literal wonders so far. You can read more about it, as well as the pain and glory of Lore’s unrelenting drive, in the full Fortune profile. Happy pitching.

Jason Del Rey
X: @DelRey
Email: jason.delrey@fortune.com
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This story was originally featured on Fortune.com