Early-stage fundraising often feels like a black box especially when you’re not a repeat founder with a “pedigree” VCs expect. That’s exactly why we launched Inside the Round: to surface the real stories from real founders raising right now.
Our first episode features David Dellapelle, co-founder of Dune Security, a cybersecurity company tackling the #1 cause of breaches: human error. David recently raised $8M in seed funding, backed by Toba Capital, Craft Ventures, and others. But getting there took 200+ VC conversations, sharp pivots, and a few brutal lessons.
Here’s what stood out most from the conversation.
The Problem Nobody Was Solving
Cybersecurity startups are everywhere. But while most focus on securing infrastructure, Dune is tackling the weak spot that’s still responsible for up to 95% of breaches: human error. Think over-permissioned employees, phishing emails, or poor role configuration. It’s not a sexy problem, but it’s the one that keeps CISOs up at night.
David saw that most companies rely on outdated, ineffective training modules to manage human risk. These tools weren’t working, they were barely being used. Dune’s product goes beyond check-the-box training and reimagines how companies manage human-layer security at scale. That’s the wedge that got them in the door.
Too Many VC, Not Enough Customers
In the early days, David made the same mistake a lot of founders make: talking to too many investors, too soon. They had over 200 VC conversations, and walked away with 196 no’s.
Why? They didn’t have the traditional founder background. No Stanford CS degrees. No Stripe on their resumes. One VC even told them, flat out, that they didn’t fit the profile of the kind of founders they usually back.
The breakthrough didn’t come from refining the pitch. It came from refocusing their energy.
David stopped pitching VCs and started talking to CISOs. Within three weeks, he had 76 enterprise security leaders on the phone. That feedback shaped their product and validated the real demand. Once traction kicked in, the investor conversations shifted, and so did the outcome.
Rejection as a Data Point
Getting told “no” nearly 200 times would shake most founders. But David learned to treat each rejection as data. Not everyone’s opinion matters equally, and feedback from someone who’s never built a company often says more about them than your business.
Instead of trying to fit a mold, David leaned into what made them different: customer obsession, a unique insight into the problem, and a product-first mindset. That shift gave them leverage, and confidence, when the right VCs finally showed up.
Closing the Round, On Their Terms
By the time the seed round came together, Dune wasn’t scrambling for capital. They had customers, revenue, and leverage. They also knew what they wanted in a partner.
The team chose Toba Capital not just for the check, but for the long-term alignment. They wanted someone who could sit on the board, understand the space, and offer product strategy, not just push for growth at any cost.
They also turned down more money than they raised. Why? Because they didn’t want a bloated round or misaligned expectations. They raised what they needed to get to the next level - nothing more, nothing less.
Post-Fundraise: More Pressure, More Clarity
Closing a big round isn’t the finish line. If anything, it’s when the real pressure starts. With new capital comes accountability. David and the team didn’t throw a party. They tightened up execution.
They rebuilt onboarding flows in a weekend. They added Sunday sprints to stay ahead. They brought in key hires who could scale product and revenue fast. Every dollar had a purpose.
Founders Need an Outlet, Too
Building a company at this pace takes a toll. David talked openly about the pressure—financial, emotional, and personal.
He finds clarity by working out daily, checking in with his co-founder, and staying close to other early-stage founders who are in the same grind. That support network matters.
Reminder to founders: You don’t have to go full robot mode. Having honest conversations with the right people keeps you in the game longer, and stronger.
Why We Started Inside the Round
Go to enough NYC startup events and you’ll hear great insights from early-stage founders. But here’s the problem: those insights usually stay in the room. And when you look at podcasts, most fundraising stories come from late-stage CEOs. The context is different. The advice doesn’t translate.
We started Inside the Round to change that. Every guest on the podcast is a founder who raised in the past six months. They’re in it now - navigating hiring, product, investor pressure, and growth. We want to surface their real experiences, not the polished versions. So if you’re a founder trying to close your round or get to product-market fit, you’re going to find this useful.
🎧 Listen to the full episode here.
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