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 $250K 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?
The Sales Cycle: A typical enterprise deal can take 6-18 months. It involves multiple demos, stakeholder alignment, and legal back-and-forth. Your cash flow plan needs to reflect this reality. · Contracting: Enterprise contracts are complex. They include terms on liability, data security, service level agreements (SLAs), and payment schedules. You need a lawyer who specializes in B2B SaaS. · Pricing and Packaging: How do you price your product? Per seat, per usage, or a flat platform fee? Getting this wrong can leave millions on the table or make you seem too cheap to be credible.
Instead of burning through the rest of their investors’ money, Ben and his co-founder made a mature decision: they shut the company down. This act of humility preserved their reputation and relationships far more than "failing forward" would have.
The Strategic Detour: Your "Internal MBA"
For many founders, the next step after a failure is to jump right into another startup. Ben did the opposite. He took a detour that most of Silicon Valley would consider unconventional: he joined Deloitte Consulting.
He treated the corporate world as a paid MBA in how massive companies actually operate. He spent years deep in the trenches of finance, insurance, and payments, learning the internal language, politics, and technology stacks of the Fortune 500. This wasn’t a retreat; it was a deliberate strategy to fill the knowledge gaps his first startup had so painfully exposed.
When a "Real Job" is the Right Move
The standard advice is to never go back to a 9-to-5. But that advice is for founders who already know their industry cold. Consider a corporate "tour of duty" if you:
Need to Understand Enterprise Sales: If you want to sell to large companies, there is no better training than working inside one. You’ll learn the procurement process, how budgets are set, and what language resonates with VPs and C-level execs. · Are Entering a Regulated Industry: For ambitious ideas in fintech, health tech, or insurance, a deep understanding of the regulatory landscape isn't optional. Ben’s time at Deloitte gave him a front-row seat to the challenges in financial services. · Lack a High-Level Network: Startups often solve problems for users, not buyers. A consulting or strategy role gives you direct access to the executives who control seven-figure budgets.
Learning to "Think Big" at a Venture Fund
After Deloitte, Ben joined Team8, an Israeli venture fund known for tackling massive, complex challenges, particularly in cybersecurity. There, he learned a second critical lesson: the difference between startup iteration and enterprise system-building.
"You can’t iterate on a Fortune 500’s infrastructure,” Ben states. The "move fast and break things" mantra of consumer apps is poison when you’re dealing with a bank’s core systems. Large enterprises don’t buy MVPs; they buy de-risked solutions from credible partners.
At Team8, he saw a different model: bringing large corporations (like Microsoft, Cisco, and Citibank) in as investors in the fund itself. This "design partner" approach allowed entrepreneurs to get early feedback, de-risk their roadmap, and build for a multi-year horizon, not just the next 18 months of runway.
How to De-Risk Your Enterprise Startup
Stage the Risk: Break your grand vision into smaller, fundable components. Your seed round isn't for building the whole platform; it's for proving you can solve the first, most critical technical or market challenge. · Recruit Design Partners: Before your Series A, identify 3-5 ideal enterprise customers who feel the pain you're solving. Offer them early access and significant input on your roadmap in exchange for their commitment (even if it’s not a paid contract initially). · Build a "Why Me" Founder Narrative: Raising $80M for april wasn’t just about the idea. It was about Ben’s story. He could walk into a VC meeting and say: "My first startup failed because I didn’t understand enterprise GTM. So I spent a decade inside Deloitte learning how Fortune 500s buy software. Then I spent four years at a deep-tech VC learning how to de-risk massive infrastructure projects. I am the right founder to solve this problem because I’ve lived it from every angle."
How to Apply This This Week
You don’t need to spend a decade in the wilderness to apply these lessons. Here are three actions you can take right now:
Map Your "Known Unknowns": Make a list of the biggest GTM risks for your startup. Is it enterprise procurement? Navigating a specific regulation? Getting budget from a conservative buyer? Be brutally honest about what you don’t know. · Conduct a "Pain Audit": Talk to five potential customers, but forbid yourself from mentioning your product. Instead, ask them to walk you through their workflow, their biggest frustrations, and what they wish they could do. Listen for the "hair on fire" problem. · Re-frame Your Failure Story: If you have a past startup that didn’t work out, write down the three most important lessons you learned. Practice articulating them in a way that demonstrates maturity and de-risks your current venture for a potential investor. Turn your scars into a superpower.
Frequently asked questions
- How do you explain a failed startup to new investors?
- Frame it as a source of crucial, hard-won experience. Be specific about the lessons you learned in go-to-market, team building, or technology, and explain how you've applied those lessons to de-risk your new venture.
- Is it a good idea to work at a big company like Deloitte after a startup?
- It can be a brilliant strategic move if you have specific knowledge gaps. Use it as a paid 'internal MBA' to learn enterprise sales, navigate regulation, or build a network in a complex industry like finance or healthcare.
- What's the biggest mistake first-time B2B founders make?
- They dramatically underestimate the complexities of enterprise sales. They build an MVP without understanding procurement, legal reviews, multi-year contracts, or how to get budget allocated, which can kill an otherwise great product.
- What does it mean to 'de-risk' an enterprise startup?
- It means breaking your massive vision into smaller, manageable stages. Instead of trying to build the entire platform at once, you identify the biggest technical and market risks and tackle them in phases, often with early-adopter 'design partners'.
