Benchmark's Chetan breaks down why the path from $0 to $100M has collapsed from five years to under two, and the one thing that is actually getting harder in the AI era: reaching your first million in revenue. In this VC bonus edition of the GTM Now Podcast, he sits down with Sophie Buonassisi to unpack how AI native companies are compressing 180 day sales cycles into 30 days, why direct sales is here to stay, and how value is shifting away from code toward the last mile of customer service.

Using Legora (legal AI) and Manus as case studies, Chetan explains how Benchmark builds conviction fast, why the marginal cost of code trending to zero changes everything, and what separates the founders who win this window from the ones who miss it.

What you'll learn:
- Why the first $1M now takes longer than the next $99M in the AI era
- How top AI startups compress a 180 day sales cycle into 30 days
- The "trusted vendor" playbook for breaking incumbent distribution advantages
- Why Legora embedded inside a law firm for a year before launching
- How a magical demo plus a tightly scoped pilot collapses six month deals
- Why value is moving from the product build to the service and outcome
- What Benchmark actually looks for: technical insight that creates demand pull
- Why direct sales and forward deployed engineers are exploding in AI
- How buying one AI app triggers an enterprise to buy 100 more

Chapters:
00:00 Intro
01:13 Why Max + Paul were furious taking notes on this one
02:10 Benchmark's $2B growth fund and the changing strategy
04:57 POC to trial and the power of direct sales in AI
11:33 Meeting Max early: $0 to $100M in 18 months
15:05 Manus: 0 to $100M in eight months through PLG
17:10 Will the AI native window close?
19:09 Sizing the window: $40B software vs $1T services in legal
21:50 How Benchmark picks the winners
25:31 Turning a 180 day sales cycle into 30 days
30:45 The Legora deep dive: research, pilots, legal engineers
41:46 Why $0 to $100M keeps getting faster
42:29 The harder problem: getting to your first $1M
44:04 When code goes to zero, what do customers pay for?
48:46 Sales led vs PLG in the AI era
51:49 How to spot the right founder
55:18 What company Chetan wishes someone would build
56:48 Investors founders should follow
57:40 Working with Jack Altman at Benchmark

Connect with Chetan Puttagunta:
General Partner at Benchmark
Twitter/X: https://x.com/chetanp
LinkedIn: https://www.linkedin.com/in/chetanputtagunta/

Host: Sophie Buonassisi, SVP at GTMnow
Follow Sophie: https://x.com/sophiebuona
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

About the GTMnow Podcast:
GTMnow is the media brand of GTMfund, sharing the tactics and strategies behind how the best companies go to market. The VC series brings on top investors to break down what is actually working in go to market today.

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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

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