Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months.

His secret? Insane distribution. His formula is to ignore quality—and engineer quantity instead. While everyone obsesses over viral content, Matt posts 1,000 videos across 333 accounts daily, guaranteeing a million views through pure math. No luck required.

He applies the same "volume negates luck" philosophy to everything: 15,000 cold emails daily, thousands of Reddit posts to dominate SEO rankings.

Matt reveals the exact Reddit hack to guarantee #1 Google rankings, how AI agents automate everything from account creation to content generation, and why he purposely changes video metadata to trick algorithms at scale. At 23, he's cracked distribution so thoroughly that he can now incubate any business and guarantee its growth.

Why You Should Listen:

• How posting 1,000 videos daily GUARANTEES 1M views
• The Reddit hack that guarantees #1 Google rankings in 7 days
• Why referral revenue is the only true sign of product-market fit
• The "volume negates luck" framework that beats any growth strategy

Keywords:

startup podcast, startup podcast for founders, Matt Everett, Clover, growth hacking, viral marketing, SEO hacking, distribution strategy, AI automation, bootstrapping

Chapters:

00:00:00 Intro

00:01:31 Selling first company at 20

00:03:54 Selling second company for $800K in 3 months

00:06:37 The 1000 videos per day distribution hack

00:24:39 How to guarantee #1 on Google with Reddit posts

00:30:52 15,000 cold emails daily—the outbound machine

00:47:27 Why 30% referral revenue is true product-market fit

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

Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software.

Then Russ told investors to pretend the $5M didn't exist and bet on a $200K pipeline instead. That pivot led to 600 Fortune 2000 customers and an exit at $50M ARR.

Now building his AI measurement startup Larridin, Russ shares why being a repeat founder creates a different problem—everyone tells you your idea is great even when it's not. His solution? Don't believe anything until someone writes a check.

Why You Should Listen:

• Why he walked away from $5M ARR to pursue a $200K pipeline.
• How emergent user behavior revealed a $50M business.
• Why "everyone loving your idea" means nothing.
• Why finding product-market fit is only step 1.

Keywords:

startup podcast, startup podcast for founders, Dynamic Signal, Russ Glass, product-market fit, enterprise sales, employee advocacy, pivot strategy, B2B SaaS, influencer marketing

00:00:00 Intro

00:01:36 30 years of Silicon Valley startups

00:03:05 Dynamic Signal's original idea

00:07:29 The emergent behavior that changed everything

00:15:38 Walking away from $5M ARR to pursue a $200K opportunity

00:18:23 Why product-market fit is never final

00:22:14 Selling Dynamic Signal

00:24:30 Starting Laridin

00:36:34 Raising $17M as a repeat founder—why everyone says yes

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

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!

Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay.

Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him.

So Guy spent a year building governance features, reporting, and enterprise capabilities—all the stuff developers didn't care about but security teams needed to write checks.

Four months later, Snyk hit $650K ARR.

A year after that, $4.5M.

Then $19M.

Today it's over $300M ARR.

This episode breaks down the brutal reality of PLG when your user isn't your buyer, why Guy thinks the worst outcome for a founder is getting stuck (not failing), and how he's now raising $125M for his next company Tessl.

If you're building PLG, selling to enterprise, or wondering why your users love you but won't pay—this is required listening.

Why You Should Listen:

• Learn why thousands of users loving your product means nothing if they won't pay
• Discover the difference between product-user fit and product-buyer fit
• Understand why the worst outcome isn't failure—it's getting stuck in the grey zone
• Master the art of anchoring in the future instead of just filling today's gaps

Keywords:

startup podcast, startup podcast for founders, product market fit, PLG strategy, product-user fit vs product-buyer fit, developer tools, security startup, enterprise sales, bottoms-up GTM, Snyk founder

Chapters:

(00:00:00) Intro
(00:01:37) The first start up :Blaze.io"
(00:06:16) The Beginning & Concept of Skyk
(00:15:27) Why use Snyk
(00:23:41) The Product Led Growth for Snyk
(00:33:08) Raising for Snyk
(00:38:58) The Beginning & Concept of TESL
(00:46:39) Raising for TESL
(00:48:52) Finding PMF
(00:49:26) One Piece of Advice

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

Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make.

But the wildest part? He got Ford to commit in under a year by doing something most founders would never do: he asked for SO MUCH money that only the CEO could approve it. That one move made him "part of the transformational change" instead of a vendor they could ignore.

In this episode, Amar breaks down the exact pricing strategy he used to land an 8-figure deal, why founders who sell discounted pricing are sabotaging themselves, and what it actually takes to compete against billion-dollar incumbents like Carta (his current company, Mantle, is doing exactly that).

If you're trying to sell to enterprise, wondering if you should bootstrap or raise, or questioning whether your market even exists—this episode will reset how you think about all of it. Amar's built companies in mobile, vehicles, security, and fintech. He knows what works.

Why You Should Listen:

• Learn the pricing trick that got a CEO to sign off to an 8-figure deal.
• Discover why asking for MORE money (not less) is how you win enterprise deals
• Why getting told "you're nuts" might mean you're dead right
• Master the one metric that matters more than ARR in the early days
  
  Keywords:
  startup podcast, startup podcast for founders, enterprise sales, 5x founder, product market fit, pricing strategy, Tinder origin story, competing with incumbents, bootstrapping vs raising, SaaS pricing
  
  Chapters:
  (00:00:00) Intro
  (00:03:56) The Start & Finding PMF for Tinder
  (00:09:04) Xtreme Labs
  (00:12:18) Autonomic
  (00:17:03) The Contract Turned Acquisition
  (00:22:04) The origin of Mantle
  (00:28:56) Going into a Dominated Category
  (00:32:39) Raising & Pitching for Mantle
  (00:40:01) One Piece of Advice
  
  

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

Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked.

Two years later, Blue J went from $2M to $25M in ARR. They're adding 10 new customers every single day. NPS went from 20 to 84.

This isn't a story about getting lucky. It's about a founder who knew—with absolute conviction—that the market would eventually arrive, and made sure he was ready when it did. But it's also about the danger of fooling yourself into thinking you have PMF when you only "kind of have PMF."

Why You Should Listen:

• Learn the brutal difference between fake and real PMF
• Discover when to abandon millions in existing ARR to go all-in on something else
• Why "time to value" might be the single most important metric for word-of-mouth.
• See what it takes to survive until the market is ready.

Keywords:

startup podcast, startup podcast for founders, product market fit, founder journey, early stage startup, startup pivot, AI startup, SaaS growth, founder advice, hypergrowth startup

Chapters:

(00:02:00) Starting BlueJ
(00:9:26) Introducing AI to Tax Research
(00:12:44) Starting to Build
(00:17:03) Not Having True PMF
(00:19:44) Believing in Retrieval Augmented Generation
(00:25:34) Updating to V2 of BlueJ
(00:30:58) The Necessity of Time to Value
(00:33:47) When You Knew You Have PMF
(00:38:19) One Piece of Advice

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