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  1. A Product Market Fit Show | Startup Podcast for Founders
  2. He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails
He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders · Feb 26, 2026

After 5 years of failure, Datarails found PMF by pivoting to FP&A, rocketing from <$100k to $20M ARR with a 100% outbound sales motion.

Datarails Beat Incumbents by Connecting *Existing* Spreadsheets, Not Forcing Rebuilds

Even against other "Excel-based" FP&A tools, Datarails won deals by letting customers connect their existing spreadsheets without rebuilding them. This dramatically lowered the adoption barrier and made the learning curve immediate for finance teams with complex legacy models, creating a powerful competitive edge.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

Datarails' 5-Year Search for PMF Accidentally Built Its Unbeatable Tech Moat

Didi Gurfinkel explains that the long, pre-PMF period was spent building a deep, robust platform connecting Excel to databases. When they finally pivoted to FP&A, this over-engineered platform became a massive competitive advantage that newer, niche-focused competitors couldn't replicate.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

Datarails Unlocked PMF Signal with an $800/Month Product and No Annual Commitment

To get the fastest possible signal on their FP&A pivot, Datarails removed all sales friction. They priced their tool at just $790/month with no long-term contract, allowing customers to just swipe a credit card. This accelerated learning and validated their direction by prioritizing feedback speed over immediate revenue.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

Datarails Succeeded By Realizing Finance Teams Want to Augment Excel, Not Replace It

While most business users view Excel as a necessary evil, Datarails found finance professionals are different. They see Excel proficiency as a core skill and part of their professional identity. By offering a solution that supercharges their existing Excel workflows instead of replacing them, Datarails found its product-market fit.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

Datarails Found PMF by Hiring a Retail Salesman, Not the Founder, for Early Sales

Due to a language barrier, Datarails' founder couldn't lead initial sales calls. Instead, he trained a former retail employee to be the first account executive. This person closed four deals in one week, validating product-market fit, while founders listened in and provided real-time feedback.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

Datarails Scaled to $15M ARR with 100% Outbound Driven by Manual LinkedIn Prospecting

Instead of using data providers like ZoomInfo, Datarails built its early GTM engine on manual LinkedIn outreach. The founders personally identified and contacted target CFOs, scaling this "unscalable" motion to generate enough high-quality leads to fuel growth to over $15M ARR before adding inbound marketing.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago

A Mid-Career Founder's "No Option to Fail" Mindset Fuels Startup Perseverance

Starting his company at 42, Datarails' founder felt he couldn't afford to fail like a younger founder might. This belief that he "cannot fail" created the deep conviction needed to persevere through a 5-year search for product-market fit and repeatedly convince investors to provide more funding.

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails thumbnail

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

A Product Market Fit Show | Startup Podcast for Founders·7 hours ago