On this episode of Tank Talks, we welcome back Villi Iltchev, founder and managing partner of Category Ventures, for an unfiltered deep dive into the evolving venture capital landscape. From his early days at Salesforce Ventures to launching his solo $160M fund, Villi unpacks the seismic shifts happening in enterprise software, how AI is reshaping startup economics, and what today’s founders need most from their investors.

We get tactical about startup pricing models, founder-investor trust, and what it takes to build truly category-defining companies. Villi also shares what he learned from backing GitLab, why transparency builds long-term trust, and how he thinks about firm design as a solo GP.

Whether you're an aspiring founder, current operator, or an emerging VC, this episode is a masterclass in strategic thinking and building with purpose.

Inside the Mind of a Modern VC (00:01:00)

* Villi’s journey from tech banking to Salesforce Ventures

* Why Salesforce’s transformation into a platform company changed everything

* The parallels between Salesforce and NVIDIA’s ecosystem dominance

* How being early at Salesforce shaped Villi’s thesis around go-to-market and platform strategy

Scaling GitLab: Lessons from the Frontlines (00:15:00)

* The inside story of GitLab’s infamous database failure—and why live-streaming the crisis built trust

* Why Villi pushed GitLab to sunset unscalable SKUs and simplify pricing

* The power of bundling and setting an “aspirational” price point from day one

Going Solo: Building Category Ventures (00:25:00)

* Why Villi finally felt ready to start his own fund—and what changed

* The biggest surprises (and reliefs) in raising as a solo GP

* How LPs are getting more sophisticated and what they want from fund managers

* Why venture needs a reset and what legacy firms are getting wrong

The New Rules of Early-Stage Investing (00:32:00)

* Why founder/firm misalignment leads to orphaned startups

* The real impact of mega-funds dabbling at seed and pre-seed

* Why Category Ventures is built to be flexible—and fiercely focused on enterprise software

AI, Startups & the Future of Enterprise (00:38:00)

* Villi’s hot take on AI-powered lean startups: “It’s not the norm—and won’t be.”

* Why AI is a second-order unlock for vertical SaaS and back-office automation

* The coming wave of software replacing the BPO industry

Life, Adrenaline, and VC Energy (00:45:00)

* What gets Villi’s adrenaline pumping as a VC

* Why endless internal meetings kill his vibe—and founder calls fuel him

* How skiing and extreme adventure balance the chaos of venture

As the venture landscape shifts under our feet, Villi Iltchev is proving that thoughtful investing, deep expertise, and founder-first empathy are more vital than ever. From GitLab board rooms to building Category VC, his journey is a blueprint for those looking to lead with clarity—and conviction.

About Villi Iltchev:

Villi Iltchev is the founder and managing partner of Category Ventures, a $160M early-stage venture firm focused exclusively on enterprise software. With a career spanning both operating and investing, Villi brings a rare blend of empathy and edge to the startups he backs—having sat on both sides of the table.

He began his career in tech investment banking before transitioning into operating roles at companies like Hewlett-Packard, LifeLock, and Box. He later joined Salesforce Ventures at its inception, helping to build one of the most influential corporate venture arms in the world. During his time there, he led investments in category-defining companies like GitLab and HubSpot.

Prior to launching Category Ventures, Villi was a partner at August Capital and Two Sigma Ventures, where he built a strong track record backing developer tools, infrastructure, and vertical SaaS startups. His investments are grounded in deep enterprise domain expertise, a keen sense for go-to-market strategy, and a relentless focus on founder empathy.

A lifelong learner and backcountry skiing enthusiast, Villi draws creative energy from the outdoors and adrenaline-fueled adventures. He holds degrees in finance and philosophy and is driven by a singular belief: the best founders don’t just build products—they redefine categories.

Follow Villi Iltchev on LinkedIn: https://www.linkedin.com/in/villi04

Visit the Category Ventures website: https://www.categoryvc.com/

Follow Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.com/

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