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Home/The SaaS Podcast/Episode 171
Startup Lessons from a First Time SaaS Founder
PLG & Growth

Startup Lessons from a First Time SaaS Founder

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Kelsey Recht the founder and CEO of VenueBook, a booking platform that connects event planners with venue managers.

VenueBook helps venues to manage their leads and bookings, and market their space. And it helps event planners to easily find and book the right venue for their event.

VenueBook was founded in 2010 and is based in New York. The company has raised over $9 million in funding.

Kelsey is a first time SaaS founder who came up with the idea for this business after experiencing the pain of finding venues and booking events herself. And one of the smart things that she did in the early days wasn't to start building a software product right away, but going and talking to prospective customers and talking about their pains. In fact, that's how she found her first few customers and her first developer.

We also talk about SaaS fundraising. Although Kelsey's raised over $9 million, it hasn't been as easy as it may sound. She started with a small family and friends round to get the business started, but raising a seed round was seriously hard work. In fact, she had to go out and talk to over 100 investors before she was able to get her seed round. So we talk about the lessons she's learned there, as a SaaS entrepreneur, as a first-time founder, and as a female entrepreneur.

So I hope you enjoy the interview…

This episode is part of our PLG & Growth series.

Links

  • Omer Khan: LinkedIn | X

More on PLG & Growth

Freemium SaaS: From $8/Month to 7-Figure ARR - Bilal Aijazi

Bilal Aijazi, Polly

Freemium SaaS: From $8/Month to 7-Figure ARR

Bilal Aijazi is the co-founder of Polly, an engagement platform that brings polls, surveys, and feedback workflows into the tools teams already use like Slack, Teams, and Zoom. In 2015, Bilal was working at a consumer messaging company, watching apps like WeChat evolve from simple chat tools into full-blown platforms. He figured the same shift would happen at work. So he and his co-founder Samir started experimenting with simple solutions to collect feedback. Their first attempt was an email-based tool, but engagement was terrible. People just treated it like another survey to avoid. Then Slack opened their API. And Bilal noticed people on Twitter asking for Slack polls. So the founders quickly ported their product over, becoming one of the very first Slack apps ever built. But the installation process was clunky. Five manual steps that required copying and pasting tokens between different screens. Yet 80% of people still completed the setup. So they were clearly providing something people wanted. Then one day someone posted Polly on Product Hunt and they went viral overnight. They were getting thousands of new signups every month and struggling to keep the servers running. Yet they had zero revenue. Their first paying customer spent $8 a month for a fantasy football league. Then came the real challenge of building a freemium SaaS: figuring out who would actually pay. Most users just wanted to do something casual with polls like pick lunch spots. But through hundreds of conversations, they found where the real money was. They focused on company all-hands, sales kickoffs, and other high-stakes meetings where feedback actually mattered. Just when things clicked, Slack threw a spanner in the works. Polly had built a workflow feature for automating feedback. They were signing five-figure deals. Six months later, Slack launched their own solution. The founders had to make a choice. Stay on Slack and hope for the best, or take a massive risk and rebuild everything for multiple platforms. They expanded to Teams, Zoom, Google Meet, and embedded directly into presentations. Rebuilding their entire infrastructure was a huge undertaking, but they had no choice. Today, Polly serves millions of monthly active users and generates multiple seven figures in ARR with just 20 people.

SaaS Pricing Trap: Usage-Based Models Need Minimums to Survive - Ryan Wang

Ryan Wang, Assembled

SaaS Pricing Trap: Usage-Based Models Need Minimums to Survive

Ryan Wang is the co-founder and CEO of Assembled, an AI platform for customer support that helps companies manage both human and AI agents more efficiently. In 2016, Ryan was a machine learning engineer at Stripe. He and his co-founders spent two years building before launching in 2020—the same day WHO declared COVID a global pandemic. Their momentum vanished. About a quarter of demos didn't show up. Their SaaS pricing model—usage-based with no minimums—meant customers could scale to zero without leaving. It took 8 months to earn their first dollar of revenue. In 2016, Ryan was a machine learning engineer at Stripe. He and his future co-founder Brian built ML tools to automate support tickets, but they realized the real problem wasn't automation—it was workforce management. That became the spark for Assembled. The three co-founders spent two years building before they launched in 2020. They lined up a TechCrunch story, hit the front page of Hacker News, and then their launch landed the same day the World Health Organization declared COVID a global pandemic. Momentum vanished. About a quarter of demos didn't show up. It took them eight months to earn their first dollar of revenue. The SaaS pricing trap: When they finally got customers, they had usage-based pricing with no minimums. Customers could scale usage to zero. When usage flatlined during the pandemic, the team blamed themselves before realizing customers weren't leaving because of the product—they were just cutting costs. How Ryan fixed the SaaS pricing problem: 1. Shifted focus from chasing growth to serving customers who were getting value 2. Met customers in person, sat with support leaders, and built what actually mattered 3. Added pricing minimums to prevent revenue from dropping to zero 4. Built sticky features that justified the investment That hands-on approach worked for about 10 customers. Then it broke at 50. Onboarding took weeks. Some features worked in demos but failed in production. So they rebuilt onboarding to get it down to days and cleaned up the product so it could scale. Eventually they grew from their early customers to dozens more and reached 8-figure ARR.

Product-Led Growth to 8-Figure ARR with $0 Ad Spend - David Shim

David Shim, Read AI

Product-Led Growth to 8-Figure ARR with $0 Ad Spend

David Shim is the co-founder and CEO of Read AI, a meeting intelligence platform that helps teams capture, analyze, and act on insights from their meetings. David Shim had already built and sold a company for $200 million to Snapchat when he spotted his next opportunity: a reflection in someone's glasses during a Zoom call. During the pandemic, David noticed a fellow meeting participant's glasses reflecting ESPN.com - they were both distracted on the same call. That moment sparked a question: could AI measure meeting engagement in real-time? After cold-emailing Zoom founder Eric Yuan to validate the idea (Eric confirmed Zoom wasn't building it), David raised $10 million and launched Read AI on the Zoom App Store. The initial product showed engagement analytics - sentiment scores, attention metrics, who was distracted. Users thought it was cool. But cool doesn't pay the bills. Monthly retention sat at just 5%. Users would try the product, see their meeting scores, and never come back. David had built a dashboard when he should have built a decision-making tool. The breakthrough came when OpenAI released ChatGPT. David's team combined their proprietary engagement analytics with LLM-powered summaries, creating what they call the "narration layer" - capturing not just what was said, but how people reacted. Tone, emotions, head nods, who looked away. The transcript tells you the words; the narration layer tells you the truth. Retention climbed: 5% to 10%, then 30%, 40%, 50%, and finally 81%. Today Read AI adds 12 million accounts per year with zero ad spend. Every meeting report shared is a viral loop - all participants receive the notes, non-users see the value, and accounts multiply. Product-led growth at its purest.

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