Episodios

  • Product-Market Fit: How Tito Goldstein Found It After 2 Years of Near-Zero Revenue

    Product-Market Fit: How Tito Goldstein Found It After 2 Years of Near-Zero Revenue
    Jan 29 2026
    Two years. Almost no revenue. Tito Goldstein and his co-founder Arjun raised $3 million to build a scheduling tool for hourly workers. But when they took it to market, customers kept telling them the same thing: we need to stand out, not use cookie-cutter software. So they made a call that most founders would never risk - throw it all out and start over. The rebuild took a year. But when they launched the new version built on composable Legos instead of fixed features, it outsold the previous two years in the first month. Then it 3x'd, and 3x'd again. That's when Tito knew they'd finally found product-market fit. TeamBridge is now doing multiple seven figures with over 200 enterprise customers, including the San Francisco 49ers' Levi's Stadium and medical staffing agencies scaling to multimillion-dollar businesses with almost no admin staff. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Listen to what customers don't say about product-market fit: Buyers kept asking for features, but the real pain was "I need to stand out." Reading between the lines unlocked their product-market fit breakthrough. 📉 Throw out sunk cost when finding product-market fit: Two years of work became irrelevant when they realized connective tissue (automations, workflows) mattered more than scheduling. 🛠️ Composability wins in competitive markets: Off-the-shelf tools make you a commodity. Customizable workflows make you a differentiator in the race for product-market fit. 💰 Stay lean until product-market fit: TeamBridge kept a team of 5-6 with multiple years of runway, giving them freedom to pivot without investor pressure. 🚀 First products validate problems, not solutions: The scheduling tool failed but uncovered the real pain. Use early products to learn, not scale, on the path to product-market fit. Chapters Introduction and favorite quotes What TeamBridge does and who it serves Why composability matters for workforce software Size of the business: revenue, customers, team Origin story: interviewing Uber drivers Going door-to-door to understand hourly worker pain Raising $3M seed with just a prototype Why it took 2 years to find product-market fit The pivot: from scheduling to composable Legos First significant sale during COVID Biggest objections: explaining composability Finding the right messaging and storytelling Downsides of casting too wide a net Moving upmarket to enterprise customers How COVID forced TeamBridge to mature go-to-market Cold email lessons: honesty and relationship building Discovery-first selling: hold the pitch until you know the pain Learning the nuances of each vertical Lightning round: grit, curiosity, and fitness 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/468 Subscribe to the podcast: https://saasclub.io/subscribe
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    45 m
  • First Customer: Living in His Customer's Basement to $100M | Qualia

    First Customer: Living in His Customer's Basement to $100M | Qualia
    Jan 22 2026
    He lived in his first customer's basement for a year. Nate Baker found Qualia's first customer by wearing a Stanford sweatshirt to a conference. That customer, Barry Feingold, didn't just sign up—he taught them the industry, made intros to competitors, and let the team live in his basement. In this episode, founders will learn how to find their first customers through network-based selling and multi-year upfront contracts. Nate shares the brutal early days: building for months without talking to customers, getting their first customer's software shut off overnight, and plateauing at $45K ARR because they didn't respect sales as a skill. Their VP of Sales told them: "I've never seen such a gap between great product and incompetent sales execution." Within 12 months, they went from $45K to $3.5M ARR. Today, Qualia generates over $100 million in ARR with 600 employees and has raised more than $200 million to transform the home buying process. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 First Customers Must Come From Your Network: Nate says your first 10 customers must come from in-network sales—cold outreach rarely closes when you're asking someone to trust an unproven system of record. 💰 Multi-Year Upfront Contracts Bring Cash Forward: Qualia offered 5-year contracts paid upfront at 80% discounts, aligning incentives and generating meaningful early revenue. 🏠 Embed Yourself With Your First Customer: The first 25 Qualia employees rotated through Barry's basement learning the industry—"you have to be so in it" to build great software. 🗺️ Geographic Focus Beats National Expansion Early: Qualia stayed focused on Massachusetts for the first year, building deep relationships before expanding state by state. ⚡ Crisis Creates Your Most Productive Moments: When Barry's vendor shut him off overnight, Qualia had to deliver—it became their most productive month ever. 🔧 Engineers Must Respect Sales as a Skill: At $45K ARR, the founders thought product would speak for itself. Hiring a VP of Sales unlocked $3.5M ARR in 12 months. Chapters Introduction and what Qualia does How Nate picked the title software market at 21 with no experience The academic approach to market selection (and why it was a mistake) The real problem: coordination across multiple stakeholders Finding first customer Barry Feingold at a conference Living in Barry's basement for a year When Barry's vendor shut him off overnight How long it took to ship the first version Why narrow geographic focus beats national expansion early Early customer conversations and what they actually needed How to get customers to pay before you've built the product The multi-year upfront contract strategy Network-based selling vs cold outreach for first customers The wake-up call: "Great product, incompetent sales execution" Moving upmarket and the "you don't understand Texas" objection Strategy for geographic expansion state by state When Nate realized they had real traction How the opportunity looks today with AI Lightning round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/467 Subscribe to the podcast: https://saasclub.io/subscribe
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    52 m
  • Enterprise Sales: How Blings Landed McDonald's in 9 Months | Blings

    Enterprise Sales: How Blings Landed McDonald's in 9 Months | Blings
    Jan 15 2026
    Nine months. Zero revenue. One cold text to a CMO. Yosef Peterseil landed McDonald's as Blings' first enterprise sales customer while bootstrapping—and learned why charging for POCs changes everything. In this episode, founders will learn how to close enterprise sales deals without a playbook, why free POCs kill your priority, and when you're actually ready to hire salespeople. Yosef shares how he validated the wrong ICP for months before discovering customer success managers had no budget, why a 13-month contract structure eliminates double negotiations, and the $30,000 event mistake that taught him to build follow-up systems first. Blings now serves McDonald's, Mercedes, Meta, and Rocket Mortgage—hitting $1M ARR in 2023 with just 19 people. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Always Charge for Enterprise Sales POCs: Even $3,000-$5,000 forces customers to prioritize you and starts vendor onboarding—free trials put you at the bottom of the list. 💰 Use 13-Month Contracts: Yosef lost months negotiating POC terms then negotiating again for commercial deals—a first-month exit clause eliminates double negotiations. 🚀 Validate ICP Budget First: Dozens of customer success interviews revealed they had no budget—pivot to where the money actually is before building. 🤝 Build Follow-Up Systems Before Events: 70 leads from a $30K event went cold because they had no HubSpot sequences or lead scoring in place. 🧠 Don't Hire Salespeople Without a Playbook: A great rep closing deals proves their skill, not your product—wait until a mediocre rep can follow your process. 📈 Scale Enterprise Sales with Channel Partners: Recruiting industry veterans to open doors for commission scaled Blings faster than direct sales. Chapters Introduction and Favorite Quote What Blings Does - The MP5 Video Format Company Metrics and Enterprise Customers The Origin Story and Co-Founder Relationship Validating the ICP Through Customer Interviews Pivoting from Customer Success to Marketing Landing McDonald's Through a Cold Text Closing the First Enterprise Sales POC Lessons from POC Agreements Why You Should Always Charge for POCs Event Marketing Mistakes - 70 Lost Leads Building a Lead Follow-Up System Hiring Salespeople Too Early Building Channel Partner Relationships Scaling with 19 People Launching PLG Motion Lightning Round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/466 Subscribe to the podcast: https://saasclub.io/subscribe
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    45 m
  • Enterprise Sales: Closing Deals in 9 Days, Not 9 Months | Briq

    Enterprise Sales: Closing Deals in 9 Days, Not 9 Months | Briq
    Dec 11 2025
    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. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Sell Vision and Value, Not Features: Bassem closes enterprise sales in 9 days by confirming vision alignment and ROI before ever demoing the product. 💰 Never Do Free POCs: Free work attracts time-wasters from innovation teams. Even a dollar creates commitment and filters for real buyers. 🤝 Land and Expand for Enterprise Sales: Start with a small paid implementation that proves ROI, then expand across departments. 🏢 Target the Economic Buyer: CFOs write checks; innovation VPs waste your time. Always qualify whether your contact controls budget. 📉 Fire Bad Enterprise Clients: Large companies can drag you into dark alleys with endless requests. Cut them loose to protect your resources. 🛠️ Partner for Early Credibility: Before you have enterprise logos, partner with trade associations to earn the social proof CFOs need. Chapters Why SaaS Founders Should Ignore Feature Requests Introduction & Welcome Is AI "Human Replacement" Software? The "Construction Data Cloud" Idea (And Why It Failed) Finding the Wrong ICP The "Agile" Trap: Why Most Product Teams Are Waterfall The Investor-Forced Pivot to Forecasting How to Close Enterprise Sales Deals in 9 Days Selling on "Vision & Value" vs. Features SaaS Pricing: Moving to Tokenization & Consumption First Price Was $15K—And It Was Too Cheap CFO Sales: Overcoming Risk Aversion Building Trust with Industry Associations Firing Bad Enterprise Clients Land and Expand Strategy Lightning Round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/465 Subscribe to the podcast: https://saasclub.io/subscribe
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    50 m
  • Founder-Led Sales: How He Closed Instacart and LinkedIn | Nexla

    Founder-Led Sales: How He Closed Instacart and LinkedIn | Nexla
    Dec 4 2025
    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. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🎯 Founder-Led Sales Connects the Dots: Unless founders sell deals themselves, they can't fully understand how product, market, and customer needs intersect. 🪄 Create "Magical Moments" in Demos: Saket's co-founder live-coded a fix during the Instacart pitch—solving problems on the spot closes enterprise deals. 🏢 Go Enterprise First: Architecting for SMBs first prevents you from understanding enterprise-grade complexity. Nexla went straight to Fortune 500. 🤝 Consultative Founder-Led Sales Builds Trust: Don't pitch—listen. Saket's first goal in meetings was to understand if the prospect saw the same problem. 📉 The "Zero Salary" Pivot: Saket and his co-founders cut salaries to zero to reach cash flow positivity before their Series A. 💰 Price Against Internal Cost: Calculate what it costs the prospect to solve the problem internally, then price at a fraction. Chapters Introduction & The "Profit" Quote What is Nexla? (Solving the Data Fragmentation Problem) The Origin: From Ad Tech to Data Infrastructure The Contrarian Strategy: Why "Enterprise First"? Landing the First Customer (Instacart) The "Live Code" Founder-Led Sales Demo Strategy Figuring Out Enterprise Pricing & POs Founder-Led Sales: Closing the First 15 Customers Overcoming the "We Can Build It Ourselves" Objection The Pivot: Going "Zero Salary" to Hit Cash Flow Positive The Impact of AI on Data Engineering Lightning Round: Best Advice & Productivity Tools 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/464 Subscribe to the podcast: https://saasclub.io/subscribe
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    42 m
  • AI SaaS Pivot: From Consulting Trap to $1M ARR | Cotera

    AI SaaS Pivot: From Consulting Trap to $1M ARR | Cotera
    Nov 27 2025
    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. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🚨 Early AI SaaS Revenue Can Be a Trap: Ibby hit $150K ARR but customers weren't logging in. The business looked like software but operated like an agency—a dangerous signal he almost ignored. 🔄 The Consulting Trap Kills AI SaaS Scalability: When every customer needs custom work, you're not building a product. If customers call for answers instead of logging in, you've built a services business. 💡 Let API Breakthroughs Trigger Your Pivot: Ibby's co-founder solved a customer problem with 100 lines of OpenAI code that outperformed a complex data science solution. That contrast made the AI SaaS opportunity obvious. 🎯 Deliver Value Upfront in Outbound: Instead of pitching, Ibby sends actual leads from a Reddit monitoring agent. "If you actually show value, people go crazy for it." 📉 Analytics Products Lack Stickiness: Dashboards answer questions, but once answered, there's no reason to return. AI SaaS products need ongoing utility, not one-time insights. 🛠️ Teach Customers to Build, Don't Build for Them: After the pivot, Cotera stopped doing custom implementations. They showed customers how to build their own AI agents—that's what made the AI SaaS business scale. Chapters Introduction Favorite Quote & Mindset What is Cotera? Ideal Customer & Revenue Snapshot Founding Story & YC Entry Early Product & Customer Interviews Outbound Strategies on LinkedIn Effective Outbound Today Common Mistakes with AI Outreach Realizing the Need to Pivot OpenAI API "Wake Up" Moment Transitioning to AI SaaS Agent Builder Product Differentiation & Competition Prompt-Based Workflow Approach Traction Before & After Pivot Evolving Pricing Model How to Contact Ibby 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/463 Subscribe to the podcast: https://saasclub.io/subscribe
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    57 m
  • Freemium SaaS: From $8/Month to 7-Figure ARR | Polly

    Freemium SaaS: From $8/Month to 7-Figure ARR | Polly
    Nov 20 2025
    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. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 📡 Signal House → Learn more and get a demo 🔑 Key Lessons 🚀 Pain tolerance signals demand: 80% of users completed a 5-step manual install—proving massive demand before Slack even had an app store. 💰 Freemium SaaS conversion requires separating users from buyers: Most free users picking lunch spots will never pay. The buyers are running company all-hands and sales kickoffs. 🔄 Surviving platform risk means diversifying: When Slack built Workflow Builder, Polly expanded to Teams, Zoom, Google Slides, and PowerPoint. 🎯 Hook conversations into the product: Every signup triggers an email asking for feedback—these conversations reveal which use cases convert to paid. 💡 Creator pricing works for horizontal freemium SaaS: Charge poll creators, not every user. Enterprise tiers shift to monthly active users. Chapters The "Punch in the Face" Reality of Startups What Polly Does and Who It Serves Scaling to Millions of Monthly Active Users The Origin: Messaging Platforms Meet Enterprise Launching on Slack Before the App Store Existed The First Product: Polls in Slack The 5-Step Onboarding Nightmare (That Worked) Product Hunt Viral Moment Transitioning from Viral Bot to Real Company The Freemium SaaS Strategy The Fantasy Football Customer: First $8/Month Finding Buyers in a Sea of Free Users Free-to-Paid Conversion Challenges What Goes Behind the Paywall Horizontal vs. Vertical Approach Building Polly Workflows When Slack Built a Competing Feature Managing Platform Risk Why Technical Founders Must Learn Sales Building on Multiple Platforms Today Would You Start Horizontal Again? Lightning Round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/462 Subscribe to the podcast: https://saasclub.io/subscribe
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    57 m
  • Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem) | GoProposal

    Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem) | GoProposal
    Nov 13 2025
    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. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 📡 Signal House → Learn more and get a demo 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🚀 Small tech, big exit: James built an 8-figure bootstrapped SaaS on a £4,000 WordPress plugin MVP—proving you don't need massive funding. 📚 Market like a celebrity chef: Give away your methodology for free. People still buy because they want it done faster. 🎯 Built to sell from day one: Before his first customer, James calculated his exit number and printed acquirer logos on his wall. 💡 Bootstrapped SaaS forces creativity: When conferences cost £25K, he hired a videographer instead and dominated online. 📋 Playbooks enable premium exits: Every process documented. Acquirers pay more when they see exactly how the business runs. Chapters The "Don't Wish It Were Easier" Philosophy What GoProposal Does for Accountants Characteristics of the Solution: Close in 15 Minutes From Business Consultant to SaaS Founder The £4,000 WordPress MVP That Scaled Why Not Knowing Tech Was an Advantage Trading Equity for Credibility Writing a Bestselling Book in 2 Weeks Getting the First 100 Customers The Bootstrapped SaaS Marketing Playbook Outpacing Competitors with Speed Creating Content Without Being an Expert The Power of Proximity to Customers The PATH Method: Pain, Aspirations, Traps, How Onboarding: The Shock and Awe Approach Growing to 1,100+ Customers Why He Skipped Conferences for a Videographer Preparing for Exit from Day One The M&A Process and Due Diligence Why He Never Raised Money Life After Exit: The Crash and Recovery Small Tech, Big Exit: The New Project Lightning Round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/461 Subscribe to the podcast: https://saasclub.io/subscribe
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    1 h y 17 m