• Enterprise Sales: How Egnyte Competed Against Box and Dropbox
    Feb 26 2026
    Hundreds of competitors. Billions in funding. All giving product away for free. Vineet Jain ignored the playbook. No freemium. Enterprise sales only. A hybrid cloud approach nobody believed in. In this episode, founders will learn how Egnyte grew from $0 to $300M+ while raising just $137.5M - and why charging from day one beat free. Egnyte now has 23,000 customers, 1,400 employees, and has raised no additional funding since 2018. It took 12 years to hit $100M - then just 3 more to reach $200M and 1.5 to hit $300M. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🏢 Enterprise sales can outperform freemium in a crowded market: Egnyte refused free tiers while Box and Dropbox gave products away. Charging from day one built a sustainable business on just $137.5M raised. 💰 Start your enterprise sales pipeline with SEM before building a sales team: Vineet spent $6,000 on SEM in month one. That approach scaled to millions per quarter and still drives 60% of pipeline today. 🎯 Lead with compliance and security to win deals as a tiny startup: Egnyte landed a Fortune 86 customer within its first 25 deals by focusing on certifications and content governance. 📉 Use failure to build defensible differentiation: Vineet's first startup got crushed by Oracle and SAP. That taught him to build capabilities giants cannot easily replicate, like hybrid cloud. 🧠 Replace consensus with small teams of 3 for faster decisions: Critical decisions at Egnyte are owned by teams of 3 with full accountability, not committees. 🛠️ Build hybrid when the market says go cloud-only: About 30% of Egnyte customers use hybrid deployment for use cases where pure cloud fails. 🚀 Scale inside sales in low-cost cities to keep CAC low: Egnyte built offices in Spokane, Raleigh, and Salt Lake City instead of expensive tech hubs. Chapters Introduction What Egnyte does and company overview Revenue milestones and funding history Arriving in the US with $100 and no connections First startup Valdero - raised $7.5M and failed Starting Egnyte with 4 co-founders and no funding Going enterprise-only when everyone said do freemium The hybrid cloud bet Landing the first enterprise customers with $6K in SEM A Fortune 86 company visiting a 12-person startup Why employees come first, not customers Consensus is the shortest path to mediocrity AI strategy and the Egnyte Copilot launch 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/471 Subscribe to the podcast: https://saasclub.io/subscribe
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    51 mins
  • Product-Market Fit: From Edtech Vitamin to $100M Painkiller
    Feb 19 2026
    Seven years selling a nice-to-have. Then 1,000 customers in year one. Adam Markowitz spent nearly a decade grinding in edtech before finding product-market fit at Drata. In this episode, founders will learn how to tell the difference between a vitamin and a painkiller - and why that distinction changes everything. Adam shares how experiencing a compliance pain at his first startup became the foundation for Drata, why he refused to sell until his team used their own product to get SOC 2 compliant, and how a "give before you take" approach to AWS made Drata a top 5 ISV on Marketplace in under two years. Drata has over 8,000 customers across 60 countries, more than 600 employees, and crossed $100 million in ARR before its fourth birthday. The company has raised over $300 million. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Product-market fit shows in buyer urgency, not just signups: Drata signed 100 customers in 6 weeks and 1,000 in year one - a stark contrast to Adam's edtech company where the first 5 university customers took years to close. 🛠️ Dogfood your product before selling it: Drata refused to accept customers until they used their own tool to get SOC 2 compliant, giving them instant credibility and proving the product worked under real conditions. 🔍 Validate by talking to every stakeholder, not just buyers: Adam spoke with dozens of companies and auditors before writing code, discovering identical pain patterns that made the initial product scope obvious. 🤝 Give before you take with strategic partners: Drata brought thousands of first-time customers to AWS Marketplace before asking for anything in return, becoming a top 5 global ISV in under two years. 📉 Selling a vitamin versus a painkiller changes everything: Seven years in edtech taught Adam what product-market fit feels like when you don't have it. At Drata, customers lined up because compliance wasn't optional. 🚀 Reassemble a proven team to compress execution time: Adam brought back the same co-founders, engineers, and go-to-market team from Portfolium. The muscle memory from working together for 7 years accelerated every phase of Drata's launch. 🏢 Keep partners independent to build a distribution moat: Drata's Auditor Alliance kept audit firms independent rather than competing with them. Two-thirds of Drata's pipeline is now sourced or influenced through partner channels. Chapters Introduction What Drata does and the trust problem it solves Revenue, customers, and team size From astronaut dreams to NASA's Space Shuttle program Building Portfolium after NASA retired the shuttle Teaching himself to code and finding a CTO Selling Portfolium for $43 million The long road to product-market fit in edtech The university sales cycle that changed everything How the Portfolium pain led to founding Drata Validating the problem before writing code Getting the band back together Using Drata to get their own SOC 2 before selling Signing 100 customers in six weeks How Drata differentiated in a crowded market What broke at 1,000 customers Building the Auditor Alliance partner program The AWS Marketplace strategy and give-before-you-take Why aggressive sales culture was intentional AI tailwinds for compliance and trust Lightning round Closing thoughts 💌 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/471 Subscribe to the podcast: https://saasclub.io/subscribe
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    1 hr and 2 mins
  • Product-Market Fit: From a School Project to $20M ARR
    Feb 12 2026
    $2M to $9M ARR in one year. Then it nearly fell apart. Gilles Bertaux expanded Livestorm into meetings and sales demos after COVID, turning it into a smaller Zoom with no clear differentiator. In this episode, founders will learn how he rebuilt product-market fit by narrowing to a niche most would run from. Gilles shares why 85% of customers on monthly plans was a ticking time bomb, how a failed Series C forced the right strategic shift, and why targeting marketers instead of IT buyers let Livestorm avoid competing with Zoom on budget. Livestorm generates nearly $20 million in ARR with 3,500 customers and has raised $35 million. Gilles co-founded the company in 2016 as a university project and has led it through explosive COVID growth, a near-collapse in positioning, and a rebuild to product-market fit with enterprise buyers. 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 🎯 Product-market fit can be lost by expanding too broadly: Livestorm added meetings and sales demos after COVID, turning into a smaller Zoom with no clear differentiator. The longer the sales conversation, the lower the conversion rate. 📉 Explosive growth can mask a fragile customer base: Going from $2M to $9M ARR in one year felt like traction, but 85% of customers were on monthly self-serve plans. One button click and that revenue disappears overnight. 🏢 Narrow positioning wins against giants: Livestorm stopped competing feature-for-feature with Zoom and differentiated on three dimensions - European company for security-conscious buyers, marketers only to avoid IT budgets, and specific industries like banking and pharma. 🔄 Selling to enterprise requires rebuilding the sales team, not retraining it: Reps who closed inbound leads from a CRM could not cold-call 10,000-person companies. Gilles had to replace almost the entire original sales team with people experienced in enterprise outbound. 💰 A failed fundraise can force the right strategic shift: When Series C investors said no in 2022, Livestorm had to become profitable. That constraint pushed them toward enterprise customers on annual contracts who pay more and stick longer. 🛠️ Target the buyer with a separate budget: By positioning Livestorm as a marketing tool instead of an IT tool, Gilles avoided budget wars with Zoom and Teams. Marketers control their own spend and do not need IT approval to buy. Chapters Introduction What Livestorm does and who it serves Revenue, customers, and funding Building Livestorm as a university project The disastrous first webinar launch Why a product launch is a timeline, not a day Finding the first 10 customers through inbound SEO, Quora, and co-marketing as early growth engines Competing with GoToWebinar and Zoom How product-market fit shifted after COVID Going from $2M to $9M ARR in one year Support tickets from 200 to 20,000 and servers crashing Post-COVID churn and the virtual event collapse Why webinars survived but virtual events died Losing product-market fit by becoming a smaller Zoom Rebuilding positioning around Europe, marketers, and industries Why video is a commodity and experience is the differentiator How Livestorm processes 4,000+ feedback items per quarter The painful shift from PLG to enterprise sales Rebuilding the sales team for outbound From tech nerd to startup CEO 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/470 Subscribe to the podcast: https://saasclub.io/subscribe
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    1 hr and 2 mins
  • Bootstrapped SaaS: From Agency to $5M ARR in 2 Years
    Feb 5 2026
    Adam Fard bootstrapped UX Pilot from a UX agency side project to $5 million ARR in under two years—growing from $3M to $5.3M in just five months—without VC funding, with 15,000 paying subscribers and a 30-person team. In this episode, early-stage bootstrapped SaaS founders will learn how Adam discovered a wireframing opportunity by testing competitors and realizing they were all faking AI generation with templates. You'll hear why he spent 6-7 months solving the genuinely hard technical problem of AI wireframe generation, and how focusing exclusively on design (not no-code, not backend) became UX Pilot's biggest competitive advantage. Adam also shares his biggest bootstrapped SaaS mistake: hiring too slowly. At $30K MRR, he questioned whether revenue might disappear and hired 1-2 people at a time, waiting months between hires. Looking back, he should have hired 5 people at once to gain velocity faster instead of prolonging the bootstrapped SaaS hiring process for months. 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 🎯 Test Competitor Claims Before Building Your Bootstrapped SaaS: Adam discovered other wireframing tools were faking AI generation by swapping templates, revealing a genuine technical opportunity. 💰 Bootstrap with Existing Revenue Streams: Adam used his UX agency income to fund UX Pilot development, removing pressure to raise VC funding or hit arbitrary bootstrapped SaaS revenue milestones. 🚀 Focus Beats Feature Bloat in Bootstrapped SaaS: While competitors built no-code tools that did everything, Adam focused exclusively on AI wireframe generation—no backend, no drag-and-drop, just design. 📈 SEO Still Works for Bootstrapped SaaS in 2024: Despite advice that "SEO is dead," Adam got significant traffic from high-intent keywords around "design, UX and AI generation" by being first to target them. 🧠 Hire Faster Than Feels Safe When Bootstrapping: Adam's biggest bootstrapped SaaS regret was hiring 1-2 people at $30K MRR instead of 5 at once—slow hiring cost months of velocity. 🛠️ Talk About Your Bootstrapped SaaS Product, Not Just Education: Adam got more newsletter engagement sharing UX Pilot updates than sending generic UX education—people want to know what you're building. Chapters Running a UX agency when ChatGPT launched The user question that sparked the bootstrapped SaaS product idea Testing competitors and discovering they were faking AI Why creating wireframes with AI was technically hard Exploring fine-tuning LLMs and component-based approaches Building a 600K subscriber newsletter from product signups Getting to the first million in ARR with LinkedIn, newsletter, and SEO The bootstrapped SaaS mistake of hiring too slowly The inflection point from $3M to $5.3M ARR in 5 months Focusing on enterprise teams vs trying to target everyone 💌 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/469 Subscribe to the podcast: https://saasclub.io/subscribe
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    51 mins
  • 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 mins
  • 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 mins
  • 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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    46 mins
  • 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 mins