He Raised $80M For His Second Startup. Here’s What He Learned From The First Failure.
Many founders learn from success. Ben Borodach’s journey with his AI tax platform, april, was forged by the painful, invaluable lessons of his first failed startup. Here’s the playbook.
TL;DR: After his first venture-backed startup failed, Ben Borodach spent a decade in corporate consulting and venture capital to master enterprise systems. He then applied those lessons to found april, an AI-driven tax platform, raising $80M. This is a story about turning failure into a strategic advantage.
Key takeaways
- Treat your early career like an MBA; get paid to learn inside a large company.
- Shutting down a failing startup early is a mature move that saves investor relationships.
- Enterprise GTM is a different sport. Learn contracting, procurement, and multi-year roadmaps.
- Frame your past failures as a strength; it shows resilience and hard-won wisdom.
- To de-risk a massive idea, break it into smaller, fundable milestones.
- Think in years, not months, when building critical infrastructure for large enterprises.
Your First Startup Will Probably Fail. Your Second Doesn’t Have To.
Most founder stories focus on the highlight reel. This isn’t one of them. Ben Borodach, CEO of AI tax platform april, raised an impressive $80 million. But the foundation for that success wasn’t a prior win—it was a painful, strategically valuable failure.
His first company, Publish, a marketing automation platform co-founded while he was still a sophomore at NYU, raised a 50K seed round and then shut down. The lessons he learned from that experience—about what he didn’t know—became the playbook for his next, far more ambitious venture.
This is a tactical guide to turning a failed startup into your most valuable asset. It’s about leveraging failure to build something much bigger the second time around.
Mistake #1: Building a Product Without a Go-to-Market Playbook
Like many first-time founders, Ben and his co-founder started with technology. The idea for Publish was to dynamically serve personalized content for B2B companies, a novel concept in 2010. They built an MVP and even got investor backing from FirstMark Capital and New York Angels.
Then, reality hit. A large corporate client expressed interest and asked for a contract. As Ben recalls, “we didn’t even know what that meant.”
This is a classic first-time founder trap: being laser-focused on the product while completely naive about the sales process. You haven’t just built a product; you’ve built a B2B product, and that means entering the world of procurement, legal reviews, and security audits.
How to Avoid This Mistake
Before writing a line of code, pressure-test your go-to-market (GTM) assumptions. Who is the exact buyer? Not the company size, but the job title. Who holds the budget? What does their procurement process look like? Who else needs to sign off?
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