3 Ways I’ve Changed Venture Investing at SaaStr Fund

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So I’m mostly made good investing decisions.  My first VC investments were Pipedrive ($1.5B cash exit to Vista), Algolia (IPO candidate), Talkdesk ($10B last round, IPO candidate), Salesloft ($2.3B cash exit to Vista).  And I have a few rocketships in the next batch, from Gorgias to RevenueCat to $1B+ Owner and more.A huge congrats...

Looking back, every single time I had any misgivings about a deal, I lost 50%-100% of my money in the end.  This is different than taking risks on where the company will go, what the competitive landscape is, etc.8⃣Ask what CEO investments they're a… pic.twitter.— Jason ✨👾SaaStr.

AI has changed the competitive landscape in almost every cases.— Jason ✨👾SaaStr.3.

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Article Details

Author / Journalist: Jason Lemkin

Category: StartupsTechnology

Markets: United States

Topics: Exit Vista) Candidate) Cash Investments Made ✨👾saastr Time Jason

Source Website Secure: Yes (HTTPS)

News Sentiment: Neutral

Fact Checked: Legitimate

Article Type: News Report

Published On: 2025-05-25 @ 14:10:25 (16 hours ago)

News Timezone: GMT +8:00

News Source URL: saastr.com

Language: English

Article Length: 398 words

Reading Time: 3 minutes read

Sentences: 8 lines

Sentence Length: 50 words per sentence (average)

Platforms: Desktop Web, Mobile Web, iOS App, Android App

Copyright Owner: © SaaStr

News ID: 28958609

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About SaaStr

Main Topics: StartupsTechnology

Official Website: saastr.com

Update Frequency: 3 posts per day

Year Established: 2012

Headquarters: United States

News Last Updated: 14 hours ago

Coverage Areas: United States

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Publication Timezone: GMT +8:00

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