Six years of logging every task. Thousands of hours of executive assistant data. Richard Hollingsworth turned proprietary agency logs into an AI-powered SaaS that went from $1M to $18M ARR in nine months. Fyxer's models outperformed generic LLM wrappers from day one because they were trained on real workflows. Richard reveals why targeting professional services instead of tech workers was the AI-powered SaaS breakthrough, how a single Facebook ad signup became a $1.2M enterprise deal closed in 7...
Sep 25, 2025•50 min•Ep. 454
SMBs were 70% of revenue but churning fast with misaligned feature requests. Bernard Aceituno fired them all and focused on B2B SaaS sales in the mid-market. The result was an 8x revenue multiplier in one year, with deals closing in 2-6 weeks instead of months. Bernard reveals why the mid-market sweet spot of 100-1,000 employees moves faster than Fortune 500 for B2B SaaS sales, how Stack AI's Hacker News launch generated 20 meetings in 48 hours with zero B2B selling effort, and the "Monte Carlo"...
Sep 18, 2025•44 min•Ep. 453
Negative 110% gross margins. Then COVID demand spiked 100x overnight - and nearly killed the company anyway. Pat Kinsel spent years chasing product-market fit while losing money on every transaction. When the pandemic brought 100x growth, most of those customers were urgency buyers who churned when COVID ended. Pat reveals the product-market fit journey behind Proof's rise to nearly $100M ARR - how he used a $0 landing page for market validation before writing code, why 10 years of lobbying acro...
Sep 11, 2025•47 min•Ep. 452
Two failed startups. Zero product-market fit. Then an obsession that built a $200M ARR company. Todd Olson spent a year doing founder-led sales, refused to hire salespeople until $500K ARR, and would not scale until he saw real signs of product-market fit. That obsession paid off - Pendo now generates over $200 million in annual recurring revenue. Todd reveals how he validated product-market fit by tracking installs instead of revenue for an entire year, why raising prices 10x overnight proved P...
Sep 04, 2025•48 min•Ep. 451
He raised over $50M for TeamFlow, then fired two-thirds of his team when COVID ended. Flo Crivello pivoted to building AI products with Lindy, an agent platform that lets anyone automate workflows without code. The first version was so broken it sent emails saying "the user wants me to send an email to 50 software engineers." Flo reveals the AI product development lessons that took Lindy from a broken V1 to high 7-figure ARR, including the "Notion head fake" positioning strategy that made buildi...
Jul 17, 2025•45 min•Ep. 450
100,000 signups in the first month. A SaaS churn rate of 99.9%. Richard White had only 100 people actually using Fathom daily after Zoom featured them in their marketplace. Instead of panicking, he used those low-quality signups as the perfect testing ground to fix broken onboarding. Richard reveals how he attacked SaaS churn as the "riskiest metric" before acquisition or monetization, why 99% of signups had zero meetings on their calendars creating catastrophic customer churn, and how reducing ...
Jul 10, 2025•57 min•Ep. 449
Seven years. Near-zero revenue. Multiple failed prototypes. Rob Woollen's SaaS product validation journey at Sigma Computing is one of the longest in SaaS history. He raised $8M, built prototype after prototype, and received nothing but "polite feedback" until one lunch with Snowflake's CEO changed everything. Rob reveals the SaaS product validation signals that separate polite interest from real demand, why he rebuilt the entire product at $1M ARR because the interface "still wasn't quite right...
Jul 03, 2025•53 min•Ep. 448
He got his first SaaS customers without spending a dollar on sales or marketing - and converted every single one to paid. Jared Siegal built a consulting business with 30 clients at $2M revenue, then deployed a strategy that made his first SaaS customers completely dependent on his technology before charging them a cent. Jared reveals how getting first SaaS customers meant giving the product away free for six months while billing for consulting, why 100% of early customers converted to first pay...
Jun 12, 2025•58 min•Ep. 447
Zero followers. Zero ad budget. $1M ARR in 90 days. David Zitoun built an AI startup from nothing by recruiting 50+ TikTok affiliates who posted daily videos for 30% lifetime commissions. Two years later, Submagic hit $8M ARR with just 14 people. David reveals how he launched his AI startup with a single viral TikTok video from a brand new account, why building with AI means timing matters more than tactics, and how lowering prices - not raising them - broke through a 7-month plateau at $5M ARR....
Jun 05, 2025•55 min•Ep. 446
"This is not a product," one of his first SaaS customers told him. They were right. Cello had no dashboard, no login portal, and no analytics - just shared Notion pages and Python scripts. But those first paying users still paid because the referral program actually worked. Stefan Bader reveals how he landed his first SaaS customers by turning pre-seed investors into design partners, why success-based pricing removed all early adopter friction, and how a "powered by Cello" casual contact loop no...
May 29, 2025•52 min•Ep. 445
Two years building an enterprise product nobody wanted to buy. Jonathan Festejo spent years on a SaaS go-to-market strategy that targeted the wrong buyers. Sales cycles dragged to three months, and enterprise teams kept choosing to "do nothing" rather than switch. Jonathan reveals how fixing his SaaS go-to-market by pivoting down-market to founders doing $500K-$2M ARR cut sales cycles from 3 months to 5 days. You will learn the go-to-market strategy of targeting buyers who feel the pain personal...
May 22, 2025•45 min•Ep. 444
Cold outreach failed. Product-led growth stalled. Joseph Lee turned to a SaaS content strategy that was anything but conventional - creating free demos for strangers on Reddit, responding to product update emails with personalized demos, and building ungated tools that now drive 50%+ of traffic. Joseph shares the SaaS content strategy that took Supademo from $100K to $1M ARR in 12 months with double-digit growth every month. You will learn how programmatic SEO modeled after Zapier drives content...
May 15, 2025•59 min•Ep. 443
Everyone assumed Prodoscore was just another surveillance tool. Sam Naficy had to find SaaS product-market fit for a product category nobody asked for - while employees and buyers assumed his company was spying on them. He flipped the narrative, narrowed the TAM ruthlessly, and grew to high 7-figure ARR. Sam reveals how achieving SaaS product-market fit meant repositioning from surveillance to employee empowerment, why narrowing from "anyone with Salesforce" to 100+ seat companies unlocked real ...
May 08, 2025•42 min•Ep. 442
Egidijus Pilypas spent 18 months burning cash on outreach and didn't close a single deal. Every cold call, cold email, and RFP response failed because by the time Exacaster entered the buying process, competitors had already built trust. Founders will hear how he transformed a dead sales pipeline into 35 booked meetings at a single conference. Egidijus reveals how a niche podcast for just 1,300 potential customers became his most powerful tool for building a pipeline, why co-authoring an industr...
May 01, 2025•58 min•Ep. 441
A prospective customer wanted to hug Rami Tamir after his pitch. Six months later, she rejected the product. That early lesson in misleading enterprise SaaS validation shaped how Salto grew from a self-funded idea to 8-figure ARR with $69M in funding. Founders will hear why building enterprise software in a new category is harder than it looks. Rami reveals why he refuses design partners after a previous startup overfitted to one customer's $500K use case, how targeting discretionary budgets let...
Apr 24, 2025•54 min•Ep. 440
A buried CTA deep in the admin panel generated close to six figures in ARR - with zero salespeople, no support, and no marketing. Sameer Al-Sakran spent four years building Metabase without charging a dollar. When he finally monetized through self-serve SaaS, strangers started paying $300/month just to remove a logo. Then he followed expert advice, built enterprise sales, and nearly stalled the business. Sameer reveals why the self-serve SaaS signal was hiding in plain sight, how expert advice t...
Apr 17, 2025•55 min•Ep. 439
Callum Mckeefery was broke in 2012 when he pitched a mobile phone company two startup ideas. Both got rejected. But one last question on the way out the door sparked a bootstrapped exit worth $82 million. Founders will hear how Reviews.io grew from a scrappy MVP to 8-figure ARR using guerrilla marketing and a logo flywheel - all without raising a cent. Callum reveals how positioning as the friendly alternative to Trustpilot drove the bootstrapped exit, why he hired his best salespeople from rest...
Apr 10, 2025•1 hr•Ep. 438
Intel found his open-source code on SourceForge and asked to buy an enterprise version - before one even existed. Onur Alp Soner built Countly as a weekend side project with no validation and no customers. Yet through competitive differentiation rooted in open-source SaaS principles, he grew it to 7-figure ARR serving BMW, Coca-Cola, and AWS without a single outbound sales call. Onur reveals why his first SaaS product failed because it lacked competitive differentiation against Mixpanel, how rel...
Apr 03, 2025•1 hr 1 min•Ep. 437
850 meetings. Sleeping in his car. Flying from Spain to knock on doors without appointments. Oscar Rubio's founder selling journey proves that extreme persistence can validate demand that digital outreach completely misses. Founders will hear how Lodgerin grew from zero to 1.2 million euros in annual revenue through startup sales grit. Oscar reveals why 8 years of manual service delivery was the best validation for his SaaS product, how his first customer came back asking for something completel...
Mar 27, 2025•48 min•Ep. 436
Andrew Gazdecki bootstrapped his first SaaS to $10M ARR, then discovered that selling a SaaS business was harder than building it. That painful exit inspired Acquire.com, which has now helped over 2,000 startups get acquired with deal volume exceeding $500 million. Founders will hear the exact process for buying and selling SaaS businesses. Andrew reveals how a SaaS acquisition deal schedule brought three dozen competing buyers to the table and doubled one founder's sale price, why overvaluing y...
Mar 20, 2025•45 min•Ep. 435
Two non-technical co-founders taught themselves Bubble, built a prototype that barely worked, and convinced 15 companies to pay for it. Paul Holder's journey building customer onboarding software shows that you don't need engineers to prove demand. Founders will hear how OnRamp went from a no-code MVP to nearly 100 customers and 7-figure ARR. Paul reveals how customer onboarding software validated demand before any custom code was written, why Google Ads attracted wrong-fit leads while LinkedIn ...
Mar 13, 2025•51 min•Ep. 434
Tom Dunlop spent 18 months chasing the wrong SaaS go-to-market strategy. He sold to law firms, in-house teams, companies of every size - riding the dopamine hit of "happy ears" instead of tracking which customer type actually converted. Founders will hear how Summize reached late 7-figure ARR with 100%+ yearly growth after fixing a broken go-to-market strategy. Tom reveals how an unfocused ICP corrupted his product roadmap with conflicting feature requests, why product-led growth failed for cont...
Mar 06, 2025•51 min•Ep. 433
N.Rich spent a year landing their first 10 customers - then watched most of them churn. Enterprise sales buyers expected instant leads from a product designed for 6-18 months of account-based relationship building. After raising $4M and burning it on 150 unmanaged SDRs, Markus Stahlberg's co-founder was diagnosed with cancer and died a year later. Markus rebuilt alone and invented a 220% commission model that finally cracked enterprise sales alignment. Markus reveals how "dark attributes" like L...
Feb 27, 2025•1 hr 5 min•Ep. 432
Sameer Narkar pitched enterprise customers for two years and failed more than 50 times. When he finally broke through, it wasn't through ads or cold outreach - it was through partner-led growth that turned other companies' distribution into his own. Founders will hear how Konnect Insights reached $7M ARR across 30 countries without raising a dollar of outside funding. Sameer reveals how partner-led growth through agency channels landed his first 25-30 customers in India, why ISV partnerships wit...
Feb 20, 2025•55 min•Ep. 431
She had never run a sales cycle in her life. Alexa Grabell's background was sales ops - adjacent, but not the real thing. Yet through startup sales persistence and sheer brute force, she took Pocus from a $6,000 first deal to $1 million in ARR in less than a year. Alexa reveals how she learned startup sales on the fly by recording calls and sending them to advisors for feedback, why she abandoned product demos for deep discovery first, and how a Slack community that started with 10 people became...
Feb 13, 2025•50 min•Ep. 430
He spent two and a half years without a paycheck, nearly sold for $30M, and got to $5M ARR without a single ad. Kyle Hanslovan's SaaS growth strategy at Huntress defied every startup playbook. Founders will hear how education-led marketing, MSP channel partnerships, and a radically minimal MVP built a cybersecurity platform now generating $120M in ARR. Kyle reveals his SaaS growth strategy for scaling through "watering holes" where IT outsourcers gather, why talking to strangers gave better mark...
Feb 06, 2025•1 hr 4 min•Ep. 429
Hiren Hasmukh invested $400,000 of his own savings into a hardware company that COVID killed. He pivoted the backend software into a vertical SaaS that now generates 7-figure ARR with 22 people. In this episode, you'll learn how Teqtivity competes against heavily funded IT asset management competitors on just $2,500/month in ad spend, and why separate code bases per customer became a niche SaaS competitive advantage. Hiren reveals how long-tail Google keywords cost a fraction of the $60-70/click...
Jan 30, 2025•52 min•Ep. 428
Nathan Gilmore could only work four hours every Saturday morning on his side project. Those four hours a week turned into a 7-figure organic growth SaaS business with 6,000 customers across 180 countries. In this episode, you'll learn how TeamGantt grew almost entirely through SaaS SEO, why focusing on a single feature beat building a full project management suite, and what happened when they finally narrowed their ICP after 14 years. Nathan reveals how a $100 Google Ads coupon validated demand,...
Jan 23, 2025•59 min•Ep. 427
Jenn Knight and her co-founder had zero insurance experience and a $5K first customer. Three years and multiple rounds of startup funding later, AgentSync hit unicorn status with 8-figure revenue and 250+ customers. In this episode, you'll learn how outsiders broke into a conservative industry, secured SaaS fundraising from seed to Series B, and scaled from 5 to 200+ employees. Jenn reveals how building evenings and weekends on Salesforce enabled rapid iteration, why switching from fear-based co...
Jan 16, 2025•55 min•Ep. 426
Barb Hyman walked into a startup expecting to scale it - then discovered the product didn't work and she had six weeks of runway. She fired the entire team, rebuilt from scratch, and grew Sapia.ai to near 8-figure ARR. In this episode, you'll learn the B2B SaaS sales approach that relies on referrals over marketing, anchor logos over volume, and published research over pitch decks. Barb reveals how she ran 15 pilots with Qantas Airlines before converting to an enterprise SaaS deal, why the US ex...
Jan 09, 2025•51 min•Ep. 425
