Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up.

Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B.

Harish says it wasn't about finding product-market fit. It was about finding product-PRICE-market fit. The product was fine. The pricing model was killing them.

This episode breaks down why pricing often isn't just a business decision—it's part of your product, how to build self-serve systems that scale to thousands of customers without talking to anyone, and why you must obsess about end users AND economic buyers if you actually want adoption.

Harish is now building Augment, an AI company for logistics that just raised an $85M Series A. He shares what he learned shadow-sitting operators for 60 days and why demos mean nothing in the AI era.

Why You Should Listen:

• Why PMF is often not enough—you need product-price-market fit
• Why subtle changes can have huge results
• Why you need both users AND buyers to love your product
• How to master self-serve

Keywords:

startup podcast, startup podcast for founders, product market fit, pricing strategy, $2B exit, Shopify acquisition, product-price fit, logistics startup, self-serve systems, Amazon fulfillment

00:00:00 Intro
00:07:06 Starting Deliver in 2017
00:14:24 Struggling with only 10 customers after 9 months
00:19:53 The two changes that changed everything
00:23:43 Zero to $100M in 2 years and product-price-market fit
00:29:32 How the $2B+ Shopify acquisition happened
00:32:07 Starting Augment AI for logistics
00:47:35 PMF moments and top advice

Send me a message to let me know what you think!

Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A.

This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why the biggest opportunities come from bundling and why you need to hit 130%+ NRR to scale in B2B.

Dheeraj also shares the two near-death experiences at Nutanix in the first 5 years, how they survived, and what he's building differently at DevRev in the AI-native world.

If you're wondering whether you have real PMF, how to think about platforms vs features, or why your existing customers matter more than new ones—this is mandatory listening from someone who's done it twice at massive scale.

Why You Should Listen:

• Learn why PMF at $1M doesn't mean PMF at $10M—and why you have to find it again at every milestone
• Why "sell and run" kills startups—the real work starts after you close the deal
• See how platform thinking (not feature thinking) took Nutanix to $1B ARR
• Understand why 30-40% of revenue from existing customers is real PMF

Keywords:

startup podcast, startup podcast for founders, product market fit, platform thinking, Nutanix founder, enterprise SaaS, net dollar retention, PMF milestones, fastest to $1B, second-time founder

00:00:00 Intro
00:01:58 Starting Nutanix
00:14:24 Why he left a $20B company
00:18:53 The DevRev thesis
00:27:39 Pre-AI vs post-AI product strategy and the agent shift
00:40:57 Platform vs features
00:46:25 PMF is not a destination
00:48:10 #1 Advice

Send me a message to let me know what you think!

Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it.

When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting their bill by 95%. Then came Notion. Justin pulled 24-hour coding marathons during their POC, fixing 300 milliseconds of latency in three hours. They signed on July 25th—the same day Simon's daughter was born.

Now TurboPuffer powers Cursor, Notion, and Linear while staying profitable with just 17 people. Simon shares why he turned down easy Series A money and his framework of exactly 6 legitimate reasons to ever raise capital.

Why You Should Listen:

• The power of making something 10-100x cheaper
• Why you need to be willing to fly to early customers (how that landed Cursor)
• The 6 reasons to raise money (and why you often shouldn't)
• How working 24-hour sprints during POCs converted enterprise customers
• Why staying profitable with 17 people beats raising $30M you don't need

Keywords:

startup podcast, startup podcast for founders, TurboPuffer, Simon Eskildsen, vector database, Cursor, Notion, bootstrapping, database startup, AI infrastructure

00:00:00 Intro

00:07:52 Finding the problem

00:12:25 Building alone

00:22:27 Going viral on X

00:26:18 Closing Cursor

00:40:17 Closing Notion

00:45:26 Why he didn't raise $30M when everyone expected him to

Send me a message to let me know what you think!