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?

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In less than 12 months, Shahar went from an idea to a $30M Series A and a team of 40. He didn't sell another AI tool—he built an AI-first service that replaced expensive human consultants in the massive pen-testing market.

In this episode, Shahar breaks down the "Service-as-Software" playbook that allowed him to hit $1M ARR in just three months. He reveals how to convert design partners into paying customers before the product is finished, why he refuses to sell to service providers, and how to achieve a 40% SQL-to-Close rate in the enterprise.

Why You Should Listen

• How to hit $1M ARR in a single quarter with zero marketing spend.
• Why asking "Would you use this?" is useless and the one question that actually validates demand.
• Why "Service-as-Software" is the single best business model for AI startups
• How to maintain a 100% win rate against competitors in live bake-offs.
• The ultimate litmus test for knowing if you have true Product-Market Fit.

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, agentic AI, cybersecurity startup, B2B sales strategy, service as software, rapid scaling, Felicis

00:00:00 Intro
00:04:06 Why Manual Pen Testing is Broken
00:15:42 Ideation and The Wallet Test
00:22:38 How to Convert Design Partners to Paid
00:28:05 40 Percent SQL to Close Rate
00:33:14 The Service as Software Business Model
00:46:06 Hitting 1M ARR in One Quarter
00:48:50 Raising a 30M Series A from Felicis
00:50:01 The Turn It Off PMF Test

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Ashwin built a $1.5B company in two years. He didn't do it with a massive team or a complex 5-year roadmap. He did it by ignoring "strategy" and talking to 100+ buyers until he found a problem so painful they would pay six figures for a solution that didn't fully exist yet.

In this episode, Ashwin breaks down the exact playbook Decagon used to go from zero to unicorn. He reveals why he refused to hire anyone until $1M ARR, how to differentiate in a crowded AI market, and why your customers are the only roadmap you’ll ever need.

Why You Should Listen

• How to hit $1M ARR in 6 months with just two founders and zero employees.
• The "Willingness to Pay" test: How to know if a customer will sign a $150k check.
• Why "over-thinking" your strategy is the fastest way to kill your startup.
• How to close massive enterprise deals before you have a full product.
• Why going vertical is often the wrong move for AI startups.

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, B2B sales, enterprise sales, AI startup, customer discovery, pricing strategy, early stage growth

00:00:00 Intro
00:02:56 Selling His First AI Startup to Scale
00:09:11 Why Founders Over Intellectualize Strategy
00:13:48 How to Get 100 Customer Interviews
00:15:10 The 150k Willingness to Pay Test
00:21:05 Hitting 1M ARR with Zero Employees
00:25:09 Ignoring Scalability to Win Early Customers
00:31:43 Defensibility in the Gen AI Era
00:39:42 Mocking APIs to Close Enterprise Deals
00:42:58 The Moment of True Product Market Fit

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