Bassem Hamdy closes enterprise sales deals in 9 days—not 6 months. After scaling Procore from $10M to $100M as EVP of Marketing, he built Briq to an 8-figure ARR by selling AI automation to CFOs in construction. In this episode, early-stage B2B SaaS founders will learn the enterprise sales playbook that bypasses long procurement cycles.

Bassem breaks down exactly how to close enterprise sales fast by focusing on "vision and value" instead of product demos. You will learn why you should never do free POCs, how to identify when you're wasting time with "Innovation Teams," and the land-and-expand strategy that grew Briq from $15K deals to $100K+ contracts.

In this episode, Bassem also shares why he made the controversial call to fire bad enterprise clients, and how partnering with industry associations gave Briq the social proof to earn trust with risk-averse CFOs before they had logos.

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Saket Saurabh closed Instacart by live-coding a fix during the pitch—and that "magical moment" became the foundation of his founder-led sales playbook. In this episode, early-stage B2B SaaS founders will learn how Saket closed the first 15 enterprise customers himself using a consultative founder-led sales approach.

Saket breaks down exactly how to navigate complex corporate buy-cycles without a sales background. You will learn why he went "enterprise first" instead of starting with SMBs, how to overcome the "we can build it ourselves" objection by creating magical demo moments, and why founder-led sales is essential for connecting product, market, and customer needs.

In this episode, Saket also shares the "zero salary" pivot that made Nexla cash flow positive before their Series A—and why founders must do sales themselves before hiring a team.

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Ibby Syed built his AI SaaS to $150K ARR—then realized he'd accidentally built a consulting business. Customers weren't logging in. They'd call with questions, get answers, and disappear. In this episode, early-stage B2B SaaS founders will learn how Cotera escaped the services trap and pivoted to an AI SaaS agent platform to hit $1M ARR.

Ibby breaks down exactly how to recognize you're stuck in a consulting trap and escape it. You will learn why his co-founder's 100-line OpenAI experiment outperformed months of data science work, and the painful decision to fire legacy customers to focus on building a real AI SaaS product.

In this episode, Ibby also reveals his "value-first" LinkedIn outbound strategy that books 25+ meetings a week, why AI SaaS products need ongoing utility (not one-time insights), and how teaching customers to build their own AI agents made the business scale.

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Bilal Aijazi built a freemium SaaS to millions of monthly active users—but struggled to convert free users to paid. Then he discovered that most users would never pay, and the real buyers were hiding in plain sight. In this episode, early-stage B2B SaaS founders will learn the freemium SaaS playbook that took Polly from $8/month to 7-figure ARR.

Bilal breaks down exactly how to identify buyers in a sea of free users. You will learn the "Pain Tolerance" metric that proved demand (80% completion on a 5-step install), how to separate "pollinators" from paying customers, and why attaching to expensive company rituals drives sticky freemium SaaS conversion.

In this episode, Bilal also shares how Slack building a competing feature forced him to diversify to Teams, Zoom, and Google Slides—and why creator-based pricing works better than workspace pricing for horizontal products.

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James Ashford built a bootstrapped SaaS for £4,000 on WordPress and sold it to Sage for 8 figures—without raising a single dollar of outside funding. In this episode, early-stage B2B SaaS founders will learn the bootstrapped SaaS playbook that beat competitors with $75M in funding.

James breaks down exactly how to build a sellable asset from day one. You will learn why he printed logos of potential acquirers on his wall before getting his first customer, the "market like a celebrity chef" strategy that made his content go viral, and the "shock and awe" onboarding that impressed acquirers during due diligence.

In this episode, James also shares how trading 10% of his software for 10% of an accounting firm gave him instant credibility as an outsider, and why skipping conferences to hire a videographer was the smartest bootstrapped SaaS marketing decision he made.

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Ryan Wang made a SaaS pricing mistake that nearly killed his company. As CEO of Assembled—a workforce management platform for support teams—he chose usage-based pricing with no minimums. The result? Eight months without a single dollar of revenue while burning through runway. In this episode, early-stage B2B SaaS founders will learn the brutal reality of SaaS pricing mistakes and how to fix them.

Ryan breaks down exactly how he fixed his SaaS pricing model after the initial failure. You will learn why usage-based pricing needs guardrails, how he convinced Stripe to become his first paying customer, and the "shadow org chart" approach to enterprise sales.

In this episode, Ryan also shares why Assembled hired senior leaders earlier than most startups recommend, and how his background at Stripe shaped his approach to building enterprise software.

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Sam Darawish sold his first company for $50 million—then bootstrapped his next SaaS to $30M ARR without a dollar of outside funding. In this episode, bootstrapped SaaS founders will learn why capital constraints actually force better decisions.

Sam breaks down exactly how scarcity of capital forced Everflow to focus on what mattered. You will learn how he landed his first customers at Affiliate Summit with nothing but screenshots, why he only invested $400K after a $50M exit, and how Everflow hit profitability at just $1M ARR with 10 people.

In this episode, Sam also shares the bootstrapped SaaS mindset that led him to not pay himself for two years, and why moderate 25-30% growth beats aggressive VC-fueled expansion.

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David Shim sold his first startup for $200M, but when he started Read AI in 2021, he built something that failed spectacularly — 5% retention after 30 days. In this episode, early-stage B2B SaaS founders will learn the Product-Led Growth playbook that turned that failure into 8-figure ARR.

David breaks down how he increased retention from 5% to 81% by focusing obsessively on "Day-One ROI" instead of chasing revenue. You will learn the $0 ad spend strategy behind acquiring 1 million new accounts monthly, and why building "bridges" between platforms like Zoom and Microsoft is the secret to competing with tech giants.

In this episode, David also reveals how to design viral loops into your product (like auto-shared meeting notes), why analyzing body language gave them the edge over generic AI wrappers, and the "Multiplayer Mode" tactic that turns every user into a salesperson.

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Kevin Wagstaff and his brother Michael turned a $5,000 investment into a $27 million ARR home inspection software business—without raising venture capital for the first six years. In this episode, early-stage B2B SaaS founders will learn the "Serve Before Selling" strategy that beat well-funded incumbents.

Kevin breaks down how he spent 12 months building an SEO moat before launching, creating an "unfair advantage" in a skeptical market. You will learn his "Agency Wedge" tactic (building websites manually to sell software), the specific pricing psychology needed to move an old-school industry to SaaS subscriptions, and why he stepped down as CEO at the peak of growth.

In this episode, Kevin also reveals the "6 AM Sunday Demo" that unlocked their biggest growth wave, how to use community engagement to sell without pitching, and the "Secondary Offering" exit path that lets founders take money off the table while staying in the game.

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Back in 2011, Sergiy Korolov's team accidentally sent 20,000 test billing emails to real customers—a complete disaster. They built a simple internal tool to prevent it from happening again, shared it with the Ruby on Rails community, and it exploded. Fast forward to today: Mailtrap generates seven-figure ARR with 100,000+ monthly active users.

In this episode, Sergiy Korolov (Co-founder of Mailtrap) reveals the SaaS Pricing Strategy behind converting a massive free user base into paid customers. Learn his controversial "Mandatory Survey" tactic that unlocked deep customer insights without hurting conversion, how he used a "Fake Door" test to validate a massive product pivot before writing code, and the specific challenges of expanding from a simple testing sandbox into a full-scale Email API platform.

In this episode, Sergiy also explains why simplifying onboarding didn't increase conversions (and what that revealed about developers), the "Eat Your Own Dog Food" strategy that fueled their initial growth, and how to compete with giants like SendGrid by focusing on developer experience.

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