The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship

Omer Khan
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Oct 30, 2025 • 46min

459: Everflow: From Selling Just Screenshots to $30M ARR SaaS - with Sam Darawish

Sam Darawish, Founder and CEO of Everflow, shares insights on bootstrapping his partner marketing platform to nearly $30M ARR without external funding. He recounts the unconventional method of showcasing screenshots at a trade show, which secured early customers. Sam highlights the importance of capital efficiency, having spent only $400K to start, and discusses pivoting from targeting networks to brands, navigating the associated challenges. His journey emphasizes the balance of sustainable growth and profitability in the SaaS landscape.
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10 snips
Oct 23, 2025 • 57min

458: Read AI: The 8-Figure Playbook for Product-Led Growth - with David Shim

David Shim, the innovative Founder and CEO of Read.ai, shares insights from his remarkable journey, including successfully selling his previous startup for $200M. He discusses the initial struggles with Read.ai's retention rates and his pivotal shift to focus on day-one ROI. Discover how he built a viral product-led growth strategy that generates eight figures in ARR without traditional marketing. With fascinating anecdotes about validating ideas with industry leaders and automating meeting intelligence, David emphasizes the importance of solving real problems for sustainable growth.
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Oct 16, 2025 • 57min

457: Spectora: Bootstrapping to $27M ARR by Serving vs Selling - with Kevin Wagstaff

Kevin Wagstaff, co-founder of Spectora, transformed a $5,000 investment into a $27 million ARR home inspection software platform. He shares insights on conducting extensive customer research for nine months and how serving customers genuinely led to success. Discover the power of early SEO efforts, building 200+ websites for credibility, and the pivotal 6AM demo that unlocked growth. Now stepping back as CEO, Kevin reflects on the importance of knowing when to pass the torch and how to balance business with personal passions like golf.
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Oct 9, 2025 • 59min

456: Mailtrap: From 20,000 Email Disaster to 7-Figure SaaS - with Sergiy Korolov

Sergiy Korolov, Co-CEO of Railsware and co-founder of Mailtrap, shares a riveting journey from a 20,000-test-email fiasco to crafting a seven-figure SaaS success. He explains how releasing an internal tool to the Rails community sparked viral growth and the slow pivot from blocking to sending emails. Discover his insights on using customer interviews for pricing strategies, the surprising role of signup surveys, and validating features with a fake menu item. Sergiy also delves into the challenges of scaling and competing in the email delivery space.
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Oct 2, 2025 • 43min

455: Accelevents: How 5 Years of Nights & Weekends Built a $10M ARR SaaS - with Jonathan Kazarian

Jonathan Kazarian, the Founder and CEO of Accelevents, turned a hedge fund side project into a $10 million ARR event management platform. He candidly shares his journey through the pandemic, pivoting from in-person to virtual events and pre-selling features to survive a zero-revenue crisis. Kazarian reveals the importance of lightning-fast customer support, how hosting dinner events generated leads more effectively than cold outreach, and the tough lessons learned from layoffs during the tech downturn.
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Sep 25, 2025 • 50min

454: Fyxer: From Executive Assistant Agency to $18M ARR AI SaaS - with Richard Hollingsworth

Richard Hollingsworth, Co-founder and CEO of Fixer, transformed a bootstrapped executive assistant agency into a thriving AI SaaS business that skyrocketed from $1M to $18M ARR in just 8 months. He discusses leveraging customer data for AI development and the pivotal role of GPT-3 in automating services. Richard highlights targeting professional services for growth, details a rapid $1.2M enterprise deal, and shares insights on scaling a team from 4 to 40 while maintaining company culture. Personal stories showcase Fixer's positive impact on work-life balance.
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27 snips
Sep 18, 2025 • 44min

453: StackAI: From MIT PhD to 7-Figure Enterprise AI Platform - with Bernard Aceituno

Bernard Aceituno, Co-founder and CEO of StackAI, is a former MIT PhD who transformed his research into a no-code enterprise AI platform with over 100 customers and $16M raised. He discusses his pivot from academia to entrepreneurship and the crucial signals that led to a shift from dataset management to workflow automation. A scrappy MVP launch on Hacker News generated instant interest, while focusing on enterprise IT proved vital for growth. Bernard shares the hard lessons learned about scaling sales and navigating customer segments.
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10 snips
Sep 11, 2025 • 47min

452: Proof: SaaS Growth Lessons from $0 to $100M ARR - with Pat Kinsel

Pat Kinsel, founder and CEO of Proof, shares his journey from a notary service to a robust transaction security platform. He discusses how COVID-19 reshaped demand and pushed innovation for enterprise clients. The conversation highlights the importance of consumer engagement and strategic growth, navigating regulatory challenges, and adapting business models. Kinsel also offers quick insights on productivity, finishing tasks, and the essence of successful entrepreneurship, all while emphasizing the balance between technology and market needs.
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4 snips
Sep 4, 2025 • 48min

451: Pendo: From Two Failed Startups to $200M ARR SaaS Success - with Todd Olson

Todd Olson, founder and CEO of Pendo, shares his remarkable journey from two failed startups to a $200M ARR success. He discusses crucial lessons on overcoming challenges and achieving product-market fit. Insights into the analytics behind improving user experiences highlight Pendo's innovative approach in the SaaS space. Todd emphasizes the importance of bold design choices, the evolution of sales strategies, and defining an ideal customer profile. This engaging conversation offers valuable advice for aspiring entrepreneurs in navigating the startup world.
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44 snips
Jul 17, 2025 • 45min

450: Lindy: Pivoting a $50M Startup to Build AI Agents - with Flo Crivello

Flo Crivello, founder and CEO of Lindy, shares her journey from creating TeamFlow to launching a no-code platform for AI agents that automate workflows. She discusses the challenges of product positioning and the importance of user forgiveness in early failures. Explore how Lindy navigates the competitive AI market and achieves product-market fit through customer feedback. Flo also offers insights on leveraging Twitter for engagement and the traits that define unstoppable founders, all while highlighting the chaos and excitement of startup growth.

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