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  1. This Week in Startups
  2. Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204
Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups · Nov 6, 2025

VCs dissect Sequoia's leadership change, the AI boom's impact on valuations, and why the bar for pre-seed startup funding is higher than ever.

Menlo Ventures Hires Ex-CTOs and CPOs to Marry Operator Experience with Financial Acumen

Menlo Ventures is rebuilding by hiring former operators from companies like Splunk and Atlassian. The goal is to combine their "in the weeds" experience of running a company with the long-term vision and financial expertise of traditional investors.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

SaaS Adoption Created a "Willingness to Pay" Tailwind for New AI Tools

The rapid growth of AI startups is partially fueled by a pre-existing business culture accustomed to paying for software. Decades of SaaS adoption have removed the friction, making companies eager to pay for new AI tools that boost productivity for existing high-performers.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Venture Capitalists Must Now Be Former Operators, Not Just Finance Experts

The expectation for venture capitalists has shifted. Founders no longer just want finance professionals; they demand investors who have direct operational experience and have been "in the trenches" of building a company. This change reflects a move towards more hands-on, value-add investing.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

VCs Prioritize Hypergrowth, Believing Retention and Margins Can Be Fixed Later

In today's market, achieving massive growth is seen as the hardest problem to solve. Investors are comfortable backing companies with initially poor retention or margins, like early ChatGPT, as long as they demonstrate hypergrowth. The belief is that growth is paramount, and other metrics can be optimized over time.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Companies Spam Reddit with AI Content to Manipulate LLM Search Results

A new marketing tactic involves creating high-quality, AI-generated content on platforms like Reddit to promote a product. The goal is to have this seemingly authentic user content indexed and then surfaced by LLMs like ChatGPT in their summaries, creating an insidious and hard-to-detect marketing channel.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

AI Startup Lyser Used Its Own Chatbot to Automate Its Fundraising Process

AI chatbot company Lyser demonstrated its product's value by using it to run its entire fundraising process. The tool found investors, created the pitch deck, and answered due diligence questions via a chatbot on their website, effectively automating their own fundraise.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Sequoia Capital Uses Decade-Long Transitions to Ensure Smooth Leadership Handoffs

Instead of abrupt changes, Sequoia employs a gradual, multi-year transition process for its leadership stewards. Past leaders like Michael Moritz and Doug Leone remained involved for years after handing over the reins, ensuring stability and continuity for the firm and its LPs.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Startups with $100M+ ARR Increasingly Prefer Private Markets Over Going Public

For high-growth companies, reaching a $100M ARR milestone no longer automatically triggers IPO plans. With abundant private capital, many founders now see going public as an unnecessary burden, preferring to avoid SEC reporting and gain liquidity through private growth rounds.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

A "Smile Curve" in Retention Is the Clearest Signal of Product-Market Fit

The ultimate proof of product-market fit isn't just low churn; it's a "smile curve" on a cohort retention chart. This occurs when users who previously canceled later return to the product. This "just kidding, I'm back" behavior is a powerful signal that the product is indispensable.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Creator-Focused "Prosumer" Startups Exhibit Enterprise-Like Stickiness and Hypergrowth

Companies targeting prosumers (e.g., creators like MrBeast) are not traditional B2C. This segment behaves like a collection of small enterprises, demonstrating high loyalty and stickiness. This allows startups like Higgsfield to achieve explosive, enterprise-like growth (60x in 6 months) within a seemingly consumer market.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Top Founders Receive Term Sheets Before Their Data Rooms Are Even Complete

The current fundraising environment for top AI founders is so frenzied that some are receiving term sheets before their data rooms are even built. In one case, a founder secured offers without financials in their data room, showing how speed and competition are causing some VCs to skip fundamental diligence.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Micro-VCs From the 2021 Bubble Suffer from a Lack of Time Diversification

Many micro-VC funds raised during the 2021 peak are struggling because they deployed all capital in a short 18-month window at peak valuations. This lack of "time diversification"—spreading investments across market cycles—means their entire portfolio is underwater, leading to poor returns and difficulty raising new funds.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Pre-Seed Fundraising Now Demands Revenue Due to a VC "Flight to Quality"

The bar for pre-seed funding has risen dramatically. With an abundance of startups already generating revenue (e.g., $1M ARR), VCs are choosing these de-risked opportunities over pure idea-stage companies. This "flight to quality" has bifurcated the market, making it extremely difficult for pre-revenue founders to raise.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago

Niche AI Tools Win by Achieving Perfect Fidelity in a Single Vertical

Startups like NextVisit AI, a note-taker for psychiatry, win by focusing on a narrow vertical and achieving near-perfect accuracy. Unlike general-purpose AI where errors are tolerated, high-stakes fields demand flawless execution. This laser focus on one small, profound idea allows them to build an indispensable product before expanding.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204 thumbnail

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

This Week in Startups·6 months ago