What experience led you to identify your company's problem?

Sam Altman

Chief Executive Officer · OpenAI

Work Tracking Problem

Sam Altman says he and Justin were reluctant entrepreneurs at Asana because they thought the problem of work tracking was really important and others working on it would develop incremental solutions, leaving value on the table.

The answer starts at 14:03.

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Alex Blackwood

Co-Founder, Quality Fractional Real Estate Investing · Mogul

Buying My First Single‑Family Rental

Alex Blackwood says buying his first single-family rental in 2020-2021 was the worst process he had ever been part of, which led him to build Mogul's fractional ownership platform.

The answer starts at 4:42.

Jett McCandless

Founder and CEO · project44

Consulting for 3PLs

Jett McCandless says that starting his consulting firm Carrier Direct, where he consulted for third-party logistics companies and LSPs, is what planted the seed for Project44.

Jonathan Awad

Co-Founder, CEO · Baselayer

Selling Identity/Fraud Solutions

Jonathan Awad says his firsthand experience came from working in identity and fraud, where he signed about 95 deals in eight months and juggled hundreds of deals, which surfaced many ideas.

Caitlin Leksana

Co-Founder & CEO · Fazeshift (YC S24)

Seeing teams with no software

Caitlin Leksana says she identified the problem from seeing teams of 20 or 30 people that have no software, which she calls the perfect place to see.

The answer starts at 9:39.

Reid Hoffman

Co-Founder, Executive Board Chair · Manas Ai

Leaving his job

Reid Hoffman says he left his job because he could see staying there wouldn't turn him into the entrepreneur he wanted to become, so he started LinkedIn.

The answer starts at 6:30.

Colin Zima

Co-Founder, CEO · Omni

Losing Five Deals

Colin Zima says he had done about a hundred demos and had five unaffiliated customers who verbally committed, but then lost all five deals.