Building software is easier than ever. Growing it into a profitable business is the hard part. Every week, a founder gets specific about what actually moved the needle: finding product-market fit, landing customers, pricing, defensibility, and durable growth. Host Omer Khan has interviewed nearly 500 software founders, from their first customers to real scale. You get what actually worked, not theory. Lately that includes the honest take on AI: what it changed about building and selling software, and what it didn't. New episodes every week.
GroundCover, an AI-era observability platform, leverages eBPF technology to provide high-fidelity telemetry without traditional SDK instrumentation. Co-founder and CEO Shahar Azulay explains how the company differentiates itself by utilizing a "bring-your-own-cloud" architecture, which shifts the cost model from usage-...
Bootstrapping a SaaS company to $50 million in annual recurring revenue requires intense founder involvement, particularly in sales and customer service. Ross Andrew Paquette, founder and CEO of Maropost, details the decade-long struggle to transition from a one-person operation to a structured organization. Key insigh...
TabaPay CEO Rodney Robinson scaled his fintech company to $100 million in ARR using a lean $2.5 million seed investment by prioritizing inbound growth over expensive outbound sales. By focusing on the "push" and "pull" needs of regulated businesses—specifically lenders and fintechs—the company established a unique mark...
7Learnings provides enterprise decision automation for retailers, optimizing pricing, marketing, and inventory decisions through predictive modeling. The company originated as a consulting project, allowing the founders to secure the massive data sets required to build an accurate forecasting engine before launching th...
Workshop CEO Rick Knudtson details the journey of building an internal communications platform, highlighting the critical transition from an initial intranet focus to a successful email-based product. After nine months of struggling with low traction, the team pivoted by finally listening to customer feedback regarding...
Uplane co-founder Julius Kurfgaard details the strategy behind scaling his AI-driven marketing automation platform to seven-figure ARR within six months. The core philosophy centers on "selling before coding," where founders conduct discovery calls to identify specific pain points and deliver rapid, scrappy prototypes ...
Enterprise software success relies on strategic positioning rather than merely selling a product. Christian Lund, co-founder of Templafy, emphasizes that startups should avoid the "POC trap" by establishing clear, non-negotiable criteria for success before engaging in pilot programs. Instead of chasing small, increment...
Featherless.ai founder Eugene Cheah details the evolution of his startup from a niche research project into a high-growth AI inference platform. By developing proprietary GPU hot-swapping technology, the company overcame the industry standard of one-model-per-GPU, enabling instant access to over 40,000 open-source AI m...
Happier Leads founder George Georgiadis scaled his SaaS business from a five-year plateau at $50K ARR to $1.5M ARR by leveraging AI-driven automation and cold email outreach. After failing to raise venture capital, he bootstrapped the company by building a proprietary, self-healing system that integrates CRM, chatbot, ...
Skimmer founder Ron Hash built a successful SaaS business for pool service professionals by identifying a critical pain point: the industry's reliance on inefficient paper-based record-keeping. By cold-calling potential users, Hash validated that the market needed a mobile-first solution capable of functioning offline....
Respona co-founder Farzad Rashidi details how transitioning from a pure SaaS model to a "service-as-software" approach enabled his company to break a multi-year growth plateau and quadruple revenue in one year. By shifting focus from selling a DIY tool to delivering specific outcomes—specifically brand visibility in AI...
ThreatLocker founder Danny Jenkins transformed a struggling cybersecurity startup into a $200 million ARR enterprise by shifting from traditional detection-based security to a "zero trust" model that blocks all unauthorized software by default. This transition required ignoring conventional startup advice to pivot towa...
Mission-driven founders face significant risks of losing control over their organizations due to "financial gravity," an unconscious pressure from the financial system that prioritizes short-term shareholder value over long-term vision. Eric Ries, author of The Lean Startup and Incorruptible, argues that standard legal...
Building a successful SaaS platform requires deep domain expertise and a long-term strategic vision rather than just rapid, agile development. Mark Abbott, founder of Ninety, demonstrates this by spending years as a certified EOS coach before writing code, eventually scaling the business to $44 million in ARR and 18,50...
Paperflite, a B2B sales enablement platform, achieved seven-figure ARR by focusing on a "Netflix-like" content experience that simplifies how sales teams access and distribute collateral. Co-founder Yega Kumarappan explains that the company’s growth relied entirely on inbound leads, initially generated by actively answ...
Tibo Louis-Lucas, founder of the holding company TMAKER, shares his transition from failed, debt-ridden startups to building a million-dollar-a-month business. He advocates for a "ship fast" methodology, emphasizing the necessity of validating ideas through revenue rather than vanity metrics. By building multiple produ...
Peec AI, a platform for Generative Engine Optimization (GEO), helps companies track and improve their visibility within AI search tools like ChatGPT and Perplexity. Founder Marius Meiners scaled the business from zero to $8.6 million in annual recurring revenue within 14 months by prioritizing market demand over produc...
Building and scaling successful SaaS ventures requires deep alignment between product capabilities and a specific, well-defined buyer persona. Ev Kontsevoy, founder of Teleport and Mailgun, demonstrates that identifying the right customer—specifically the VP of platform engineering—is more critical than broad market ap...
Product Fruits founder Karel Papik details the evolution of his digital adoption platform, which now serves over 1,300 customers, including major enterprises. After facing stagnant growth and the emergence of AI-powered competitors, the company pivoted to an AI-first architecture, successfully integrating features like...
Girish Redekar, founder of Sprinto, discusses building and selling his first SaaS company, RecruiterBox, and growing Sprinto to eight figures in ARR. Before finding success with RecruiterBox, Girish and his co-founder spent years on unsuccessful ideas, eventually teaching themselves to code. He emphasizes the importanc...
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