Chaz has founded 3 companies. The first sold for over $40M. The second sold to GoPuff for even more. Now, he’s on his third act with Model ML, having just raised $75M Series A <2 years in.

In this episode, Chaz breaks down the playbook behind his successes. He reveals how he raised his first million by pitching strangers on LinkedIn, why his delivery startup was just a text message system on the backend, and why speed is the only defensive moat left.

Why You Should Listen

• How to pitch strangers on LinkedIn for angel checks.
• Why you should always say you're raising "a bit more" than you actually are.
• Why "Product Market Fit" is no longer static in the age of AI.
• How to launch a massive consumer business.
• Why getting a paid design partner isn't enough.

Keywords

startup podcast, startup podcast for founders, serial entrepreneur, fundraising strategy, product market fit, rapid scaling, AI startup, exit strategy, MVP, fintech

00:00:00 Intro
00:04:46 Pitching Strangers for Angel Checks
00:07:51 The "Fake" Fundraising Strategy
00:23:28 Why MVPs are Dead in the AI Era
00:25:01 Selling to GoPuff While Running Out of Cash
00:32:25 The Origin of ModelML
00:38:30 The Design Partner Playbook
00:46:13 From $5k to $100k MRR in 3 Months

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Jay was running a respectable AI startup with $3M ARR. But he knew it wasn't a venture-scale rocket ship. So, he decided to fire all his customers, pivot the entire company, and bet everything on a new vertical: legal AI for plaintiff attorneys.

Eve went from zero to unicorn status in under two years, raising $100M at a $1B valuation.

In this episode, Jay breaks down the brutal reality of pivoting a revenue-generating company, how to achieve "demo shock" in an antiquated industry, and why 4-hour user sessions were the first sign that he had struck gold.

Why You Should Listen

• How threatening to shut down your product can reveal PMF.
• Why firing all your existing customers might be the only way to scale.
• How to achieve a 40% conversion rate from cold outreach to demo.
• Why you should target mid market instead of enterprise if you want to deploy AI fast.

Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, legal tech, AI startup, B2B sales, unicorn startup, Jay Madheswaran, Eve

00:00:00 Intro
00:02:27 From VC to Founder
00:08:42 The First Idea: RPA for NLP
00:16:52 The Hard Decision to Pivot at 3M ARR
00:24:26 Product Discovery While Still Supporting Old Customers
00:33:56 40 Percent Conversion from Cold Outreach
00:39:56 Firing Customers to Find True PMF
00:41:06 The 4-Hour User Session Signal
00:46:05 From 1M to 10M ARR in One Year
00:49:11 The Moment of True Product Market Fit

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Bassem took Briq from a failed data idea to a Series B leader in construction financial automation.But the path wasn't linear.

In this episode, Bassem reveals how he pivoted to RPA bots, why he killed a high-growth fintech product to survive the 2023 cash crunch, and how he uses a relentless "Go-to-Market" strategy. He breaks down his exact ABM playbook, why he hates trade shows, and why he believes AI orchestration is a bigger shift than the cloud.

Why You Should Listen

• How to identify the "Challenger" who will kill your deal.
• Why trade shows are a waste of money (and what to do instead).
• The "1-Person Webinar" hack to close high-value accounts.
• The brutal reality of cutting 50% of staff to survive.
• Why selling "risk reduction" beats selling "time saved."

Keywords

startup podcast, startup podcast for founders, product market fit, account based marketing, construction tech, go to market strategy, enterprise sales, finding pmf, robotic process automation, ai orchestration

00:00:00 Intro
00:06:23 The RPA "Aha" Moment with a Tech Giant
00:11:52 Selling Risk vs. Selling Time Saved
00:13:27 The "New CFO" Signal in Account Based Marketing
00:17:06 Identifying the "Challenger" in Enterprise Sales
00:23:22 The 1-Person Webinar Strategy
00:29:19 Killing the Fintech Product to Survive 2023
00:36:20 Why You Never Truly Have Product Market Fit

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Max went from a YC rejection to building a $1.8B company in less than two years. His company, Legora, is the fastest YC-backed company to become a unicorn in history.

His path to insane growth was not standard: after raising a massive Series A, Max told his board he was pausing all new sales for six months to rebuild the product infrastructure.

In this episode, Max breaks down the "burn the boats" mentality that drove their growth, the specific demo tactics that convert 55% of prospects, and how to build an engineering culture that ships fast enough to beat incumbents like Thomson Reuters.

Why You Should Listen

• Why he shut down sales for 6 months immediately after raising $35M.
• How a single live demo stunt at a conference generated 150 qualified leads.
• The aggressive pitch strategy that turned a YC rejection into an acceptance.
• How to close a $10M round with Benchmark after a single meeting.
• Why you should encourage your enterprise clients to run bake-offs.

Keywords

startup podcast, startup podcast for founders, product market fit, AI legal tech, Y Combinator, hypergrowth, enterprise sales, Benchmark Capital, fundraising strategy, rapid scaling

00:00:00 Intro
00:06:51 Getting Rejected by Y Combinator
00:15:37 Living on 50k Euros with Design Partners
00:30:19 The Live Demo That Booked 150 Meetings
00:34:06 Raising $10M from Benchmark in 30 Minutes
00:35:13 Shutting Down Sales After Raising Series A
00:46:36 How to Win 85 Percent of Competitive Deals
00:50:05 The Moment of True Product Market Fit

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Russell went from working in private equity to hand-delivering dog food on the NYC subway at 5 a.m. He didn't start with a VC check; he started with a studio apartment kitchen and a belief that dog food was broken.

In this episode, Russell breaks down how he turned a side hustle into Spot & Tango, a direct-to-consumer giant doing over $100M in revenue.

He reveals the gritty reality of early-stage CPG, why he vertically integrated his own factory when everyone else outsourced, and how a simple "fresh dry" product innovation called UnKibble unlocked massive scale.

Why You Should Listen

• How to scale from a studio apartment kitchen to $100M+ revenue.
• How a simple packaging choice created a premium brand identity.
• Why your second product might become your biggest winner.
• Why the best performing ad creative is often the cheapest.

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, DTC startup, CPG brand, direct to consumer, scaling a startup, founder stories, Spot and Tango

00:00:00 Intro
00:02:30 From Private Equity to Dog Food
00:07:36 Hand-Delivering to the First Customer
00:11:57 The Dark Ages: Cooking in a Shared Kitchen
00:19:17 Pricing Strategy Without Sales Data
00:22:50 The Pink Butcher Paper Brand Identity
00:26:26 Launching UnKibble: The 9-Figure Product
00:31:52 Why Vertical Integration is a Moat
00:40:54 The Best Ad Creative is a Sticky Note
00:47:09 Selling Out Inventory in 4 Days

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Harman went from cold-calling hotels 100 times a day to building the category-defining guest management platform for the hospitality industry. Canary built a $600M company by first solving one tiny, annoying problem: paper credit card authorization forms.

In this episode, Harman breaks down how a simple digital form became the wedge into thousands of hotels. He reveals why they stuck with outbound sales long after hitting millions in revenue, the terror of collecting physical checks during the first week of COVID, and the exact moment he knew they had hit product-market fit.

Why You Should Listen

• The "Activated Hair on Fire" framework: How to turn a latent problem into a must-have purchase.
• Why outbound sales (and cold calling) is often your top early growth channel.
• How to use a simple, "unscalable" wedge to unlock a massive market.
• Why you should celebrate the lows: A counterintuitive take on managing founder psychology.
• The story of signing 200+ customers in a single day (and finding true PMF).

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, vertical saas, outbound sales, cold calling strategies, early stage growth, b2b sales, hospitality tech

00:00:00 Intro
00:02:13 From Management Consulting to Hotel Tech
00:11:32 The Paper Form that Launched a Company
00:17:35 The Activated Hair on Fire Framework
00:24:26 Landing the First Customer via Cold Call
00:28:21 Applying to YC
00:32:35 Making 100 Cold Calls a Day
00:43:42 The COVID Cash Flow Panic
00:48:27 Signing 200 Customers in One Day

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In this episode, Rich breaks down the wild story of Fathom's launch. He reveals how they secured a prime spot on the Zoom Marketplace and generated 100,000 signups in 30 days—only to realize 99.9% of them were useless.

He discusses the pivot to monetization when the market crashed, how to design a product for viral loops, and why staying in private beta for 10 months was the best decision he ever made.

Why You Should Listen

• Why getting 100,000 signups in a single month nearly killed the company.
• How to use the "Iceberg Strategy" to build a defensible moat.
• Why you should attack the "800-pound gorilla" incumbent.
• How to hit $100k ARR by selling a roadmap that doesn't exist yet.
• The "Visible Feature" mechanic that drives zero-cost viral growth in B2B.

Keywords

startup podcast, startup podcast for founders, viral growth, product market fit, AI startup, freemium strategy, Zoom marketplace, PLG, B2B sales, Fathom

00:00:00 Intro
00:03:14 Why Sales Reps Hated Gong
00:07:54 Betting on Transcription Costs Going to Zero
00:11:52 The 10 Month Private Beta Strategy
00:17:46 The Zoom Marketplace Launch
00:19:52 100k Signups and Zero Growth
00:26:39 Selling a Roadmap to Hit 100k ARR
00:33:53 The Viral Loop of Visible Bots
00:36:12 Why Enterprise Sales Was a Trap
00:39:51 The Moment of True Product Market Fit

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Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security.

In this episode, Bob breaks down the distinct difference between finding Product-Market Fit and finding Go-To-Market Fit—and why confusing the two can kill your company.

He shares the exact questions he asked early customers to pivot from a generic mobile idea to a billion-dollar enterprise solution, the painful transition from founder-led sales to a repeatable playbook, and why he believes agentic AI is the "mobile wave" all over again.

Why You Should Listen

• Why asking "what else is bothering you?" can uncover real pain points.
• Why finding Product-Market Fit might actually increase your burn rate.
• Why founder-led sales often fail to scale and what to do about it.
• How to use a "Deal Grind" session to turn anecdotal sales wins into a scientific Go-To-Market machine.
• Why identifying the right tech wave matters more than your initial idea.

Keywords

startup podcast, startup podcast for founders, product market fit, go to market fit, enterprise sales, founder led sales, mobileiron, agentic AI, cybersecurity startup, bob tinker

00:00:00 Intro
00:03:17 Talk to Customers Before Writing Code
00:15:28 Why Finding PMF Can Increase Burn Without Growth
00:17:51 The Founder "Magic Pixie Dust" Trap
00:25:34 The Deal Grind Exercise
00:31:43 From 1M to 80M ARR in 4 Years
00:32:54 Why Agentic AI is the Next Mobile Wave
00:38:30 The Famous Sequoia Tombstone Meeting
00:40:17 The Magic Question: What Else is Bothering You?

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