Jonathan Kazarian built Accelevents to $10 million ARR working nights and weekends for five years while keeping his hedge fund day job. But when COVID hit just as he went full-time, every event worldwide got canceled and revenue dropped to zero – forcing him to borrow $75,000 from his father's retirement to survive.

In this episode, Jonathan reveals the reality of bootstrapping a global platform without quitting your day job. He shares the brutal truth about hiring remote developers (firing 21 Upwork contractors to find one good one), the "19-Second Support" strategy that wins enterprise deals, and how they survived their entire revenue stream vanishing overnight during COVID by pivoting to virtual events.

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Richard Hollingsworth bootstrapped an executive assistant agency to $5M ARR before pivoting to an AI SaaS. In this episode, early-stage B2B SaaS founders will learn the "Agency to SaaS" playbook that drove Fyxer from $1M to $18M ARR in just 9 months.

Richard breaks down their "Data Moat"—how they used six years of manual agency logs to train GPT-3, creating a product far superior to generic wrappers. You will learn how a single Facebook ad led to a $1.2M enterprise deal closed in just 7 days, and why targeting "Professional Services" instead of tech companies unlocked massive growth.

In this episode, Richard also shares the brutal reality of hypergrowth (like when support response times collapsed), the "Unreasonable Effort" mantra that aligns his team, and how living in a hacker house in San Francisco shifted their ambition from "What if Google builds this?" to "This will be huge."

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Bernard Aceituno went from PhD research at MIT to founding Stack AI, a no-code AI platform that's now generating 7-figures in ARR with over 100 enterprise customers and $16M raised. In this episode, early-stage B2B SaaS founders will learn the enterprise AI strategy that turned a scrappy MVP into a market leader.

Bernard shares how a perfectly-timed launch on Hacker News generated 20 enterprise meetings in 48 hours. You will learn why chasing too many customer segments (SMBs vs. Enterprise) nearly derailed the company, and the data-driven framework he used to fire small customers and double down on IT teams.

In this episode, Bernard also explains the "Monte Carlo" approach to testing sales channels without wasting time, why early reseller partnerships failed, and the "Maker vs. Manager" schedule that allows founders to code and sell simultaneously.

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Pat Kinsel went from years of painful struggle at Notarize to building Proof, a SaaS platform approaching $100M ARR with 230 employees and $260M raised. In this episode, early-stage B2B SaaS founders will learn the growth strategy that turned a notary error into a market-defining company.

Pat explains how he validated demand with a simple landing page before writing a line of code, how he endured years of negative margins, and the specific "Regulatory Moat" strategy of lobbying to change state laws. You will also learn why the 100x COVID demand spike was actually a "false signal" that nearly killed the company, and how he pivoted from a point solution to a full transaction security platform.

In this episode, Pat also shares the "Sunday Night" habit that keeps him connected to the product, why he rebranded to expand his TAM, and the reality of firing non-strategic customers to save the business.

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Todd Olson went from two failed startups to building Pendo, a SaaS platform now generating $200M ARR with 880 employees and nearly $500M raised. In this episode, early-stage B2B SaaS founders will learn how an obsession with product-market fit turned past failures into a unicorn.

Todd reveals why he refused to hire salespeople until he validated the sales motion himself (at $500k ARR), how he used manual outreach instead of inbound to create a new category, and the controversial pricing decision—raising the minimum from $99 to $1,000 overnight—that changed the company's trajectory forever.

In this episode, Todd also explains how building "Auto-Track" gave them an unfair advantage over competitors like Segment, why "Product-Led Growth" failed them early on, and the specific metrics he used to validate fit before scaling.

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Flo Crivello built one of the fastest-growing AI SaaS companies after a brutal startup pivot. His previous company, TeamFlow, raised $50 million—but when people returned to offices, growth flatlined overnight. He had to fire two-thirds of his team. In this episode, early-stage B2B SaaS founders will learn how Flo turned that failure into Lindy, an AI SaaS platform now generating high seven figures with just 25 employees.

Flo reveals why he rebuilt his AI SaaS product from scratch at $100K MRR, how tweeting 20 times a day for years led to 70,000 waitlist signups from a single video, and the "Zapier for AI" positioning breakthrough that made customers finally understand what an AI agent platform was.

In this episode, Flo also shares why Lindy's first product literally sent nonsense emails to job candidates (and why early adopters were surprisingly forgiving), the YouTuber discovery that triggered explosive growth five days after launch, and his advice for founders building AI SaaS products today.

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Richard White had 100,000 signups in his first month—and only 100 people actually using the product. His SaaS retention rate was effectively 0.1%. In this episode, early-stage B2B SaaS founders will learn how to fix broken SaaS retention before worrying about monetization.

Richard breaks down exactly how he turned a catastrophic retention crisis into an 8-figure business. You will learn why 99% of his signups had zero meetings on their calendars, how a "fake meeting" feature solved the trust problem killing activation, and the 60-day ultimatum that forced his team to monetize.

In this episode, Richard also shares how he sold a team plan before it was built—with just two features and a slide deck—and why that approach hit $100K ARR in month one.

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Rob Woollen spent seven brutal years with almost zero revenue before finding product-market fit. Then, after finally hitting $1M ARR, he made the gutsy call to rebuild the entire product from scratch. In this episode, early-stage B2B SaaS founders will learn the reality of the long search for product-market fit.

Rob breaks down exactly how a single lunch with Snowflake's CEO changed everything. You will learn why founders must be "entirely irrational," how to recognize real product-market fit signals vs. polite feedback, and why he rebuilt at $1M ARR when most founders would celebrate.

In this episode, Rob also shares how losing two founding engineers after 10 months nearly killed the company, and why the quarter after they thought they had product-market fit resulted in zero sales.

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Jared Siegal got his first customers by giving his product away for free—then converted every single one of them to paying subscribers in four months. In this episode, early-stage B2B SaaS founders will learn how to acquire first customers without spending on sales or marketing.

Jared breaks down exactly how he turned 30 consulting clients into his first customers using a "Trojan Horse" strategy. You will learn how to borrow resources from clients to build your MVP, why giving your SaaS away for free creates unbreakable stickiness, and the negotiation leverage that comes from being profitable before raising capital.

In this episode, Jared also shares the "Disney World strategy" that creates client loyalty beyond contracts—some of his first customers have literally written him into their wills.

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David Zitoun bootstrapped Submagic from zero to $1M ARR in just 90 days—then scaled to $8M ARR with a 14-person remote team. No VC money. No sales team. Just TikTok videos and an army of affiliates. In this episode, bootstrapped SaaS founders will learn how to go viral with zero followers and build a scalable affiliate program.

David breaks down exactly how he recruited 50+ affiliates paying 30% lifetime commissions, why he went viral on TikTok from day one with zero followers, and the bootstrap-friendly growth playbook that took Submagic from idea to $8M ARR in two years.

In this episode, David also shares why lowering prices—not raising them—broke through a $5M plateau that stalled growth for seven months, and how WhatsApp groups with early customers turned them into free product managers.

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