Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years."

So they did something else—they bought the parking operators and implemented the AI themselves. VCs called them delusional. But today, Metropolis has 20 million members adding 60-80,000 new users daily. Every 1-2 seconds someone signs up.

Alex's biggest lesson? When enterprise customers won't adopt your tech, don't convince them—buy them. Sometimes the only way to disrupt an industry is to become the industry.

Why You Should Listen:

• The "growth buyout" playbook—buy old companies to force your tech
• Why adding friction made their product better
• The counter-intuitive metric: success = less time users spend in your product
• Why VCs said "absolutely not" to their best strategic move

Keywords:

startup podcast, startup podcast for founders, Metropolis, Alex Israel, computer vision, growth buyout, parking technology, M&A strategy, enterprise sales, B2B SaaS

00:00:00 Intro

00:03:05 Seeing the parking opportunity

00:06:37 The original vision

00:12:33 Raising $7.5M and leasing the first two parking lots

00:16:04 First customer transaction

00:22:58 The growth buyout strategy

00:27:54 Acquiring SP Plus with 23,000 employees

00:34:32 Building beyond parking

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Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing.

He started Instalily in Spring 2023 when everyone said AI agents were impossible. Instead of replacing workers, he built AI that finds signals in noise—telling each salesperson exactly which deal to focus on right now. The results are insane: $1M ARR within months, tripling revenue year two, delivering $150M+ value to single customers.

His secret? While competitors pitched flashy demos, Amit's team attended 100+ trade shows to understand actual operator pain. They hired fresh AI grads who "shipped fearlessly" instead of senior talent stuck in old paradigms.

Why You Should Listen:

• How "operator market fit" beats product market fit for enterprise sales
• The GTM playbook that hit $1M ARR in months by attending 100+ trade shows
• Why hiring AI-native grads crushed hiring senior talent for AI products
• How focusing on time-to-value unlocked enterprise deals
• The counterintuitive approach: augment the best parts of jobs, not the worst

Keywords:

startup podcast, startup podcast for founders, Instalily, Amit Shah, AI agents, enterprise sales, operator market fit, B2B SaaS, AI automation, vertical SaaS

00:00:00 Intro

00:04:42 Leaving 1-800-Flowers

00:09:55 Starting when everyone said AI agents were impossible

00:11:51 The vision—amplify the best parts of work, not replace the worst

00:16:59 Operator market fit over product market fit

00:20:48 Landing first $2B enterprise customers

00:29:00 The 100+ trade show GTM strategy that actually worked

00:33:02 Why they hired AI-native grads instead of senior talent

00:34:51 Hitting $1M ARR in months

Retry

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Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard.

But the journey was brutal. Wayne worked solo for a year, burning through savings in San Francisco. Flew to South Africa for 7 weeks to land his first insurance partner.

The real breakthrough came 4 years later, in 2019, when Elon tweeted about Tesla insurance—instant rocket ship growth. Today Sure is the rails for embedded insurance, like Visa for credit cards.

They raised $120M but haven't needed money since 2021 because they've been profitable since their Series B.

Why You Should Listen:

• How to validate an entire business in a weekend.
• Why he worked solo for a year before raising money or hiring anyone.
• The exact playbook for pivoting while keeping your old product alive.
• How one Elon Musk tweet created instant product-market fit.

Keywords:

startup podcast, startup podcast for founders, Sure, Wayne Slavin, embedded insurance, InsurTech, product validation, bootstrap to profitable, Tesla insurance, B2B pivot

00:00:00 Intro

00:01:48 The flight to Vegas that sparked a $120M insurance company

00:03:03 Building a fake insurance product in one weekend to test demand

00:11:00 Working solo for a year while burning through savings

00:14:43 Flying to South Africa for 7 weeks to land first insurance partner

00:19:58 Convincing 5 friends to quit their jobs

00:27:56 Pivoting from mobile app to embedded insurance

00:46:03 Elon's tweet creates rocket ship growth overnight

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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

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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

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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

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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

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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

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