What happens when an investor gets tired of guessing, and decides to rebuild the guessing machine itself?

Ali Dastjerdi didn’t stumble into AI for investing, he escaped into it. After years inside Insight Partners, swimming in deal flow, pattern matching companies, and watching great decisions hinge on incomplete information, he walked away to fix the system from the inside out.

Ali is the co-founder and CEO of Raylu, an AI-native platform helping private market investors move from thesis to conviction faster, with less noise and more signal. Before Raylu, he backed category-defining companies at Insight and lived the daily reality of sourcing, diligence, and missed timing. Today, he’s building AI agents that think like investors, not spreadsheets.

In Todays Episode We Discuss:

00:01 – Ali’s background, machine learning roots, and joining Insight Partners

03:40 – Why investing felt broken from the inside

06:15 – Early startup attempts and the pull back to company building

09:10 – The original Raylu idea and why it failed

12:30 – ChatGPT as a forcing function and the reset moment

15:20 – From infrastructure to vertical SaaS for investors

18:45 – Private markets as a sales and timing problem

22:10 – Why proprietary deal flow matters less than investors think

25:30 – Teaching AI agents what “good” actually means

29:40 – Replacing databases with adaptive investor workflows

33:15 – AI as conviction acceleration, not decision-making

36:50 – What investor work should never be automated

40:20 – How better context changes investment outcomes

44:30 – The future of venture in an agentic AI world

Along the way, Ali reframes venture capital as a sales problem, explains why most founders are pitching the wrong investors, and shares why being 5 percent better in a hyper-competitive market is often the difference between missing and winning generational companies.

We close where it gets personal. An investor who became a founder, now building tools for investors, wrestling with the same question from the other side of the table. If capital is the least differentiated product in the world, maybe the future belongs to those who combine judgment with intelligence, and know which parts should never be automated.

Quotes:

“Investors aren’t convinced by founders, they’re pattern-matching for believers.”

“AI shouldn’t make the decision. It should make you dangerous enough to make a better one.”

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