Can investors stay ahead of evolving cyber threats—and what does it take to spot the next big cybersecurity startup before the market catches on?
In this episode of Driving Alpha, host Sam Silvershein sits down with Bob Ackerman, founder of AllegisCyber Capital and co-founder of DataTribe, to explore the shifting cybersecurity landscape. Bob explains how his early insights led him to bet entirely on cybersecurity before it was mainstream and shares why deep domain mastery is a must for both founders and investors in this complex, rapidly evolving sector.
With 20+ years at the forefront of cyber investing, Bob offers rare visibility into the dual-use nature of AI in cybersecurity—how artificial intelligence is reshaping both offense and defense. He also breaks down the biggest risks on the horizon, including vulnerabilities in critical infrastructure, the rise of deepfakes, and the race to map the next generation of networks. Whether you’re a VC, founder, or just someone fascinated by the intersection of technology, security, and innovation, this episode delivers invaluable insights.
Transcript
Sam Silvershein:
Welcome to Driving Alpha, the podcast where we dive deep into venture capital, entrepreneurship, and the forces shaping the future of technology investing. I’m your host, Sam Silvershein, and today we’re tackling one of the most critical sectors in tech—cybersecurity.
Joining us is someone who saw the future before the rest of the market did. Bob Ackerman founded AllegisCyber Capital in 1996 with a vision to create an entrepreneur-centric, early-stage venture firm. In 2012, he doubled down on cybersecurity, making AllegisCyber the first VC firm focused entirely on this essential sector.
Bob has been called one of “cyber’s money men,” and in 2015, he raised the world’s first dedicated cyber fund. He didn’t stop there—he co-founded DataTribe, a cybersecurity foundry near Washington D.C., helping launch high-impact companies with deep technical expertise.
So Bob, welcome to Driving Alpha!
Bob Ackerman:
Hey Sam, it’s great to be here. Thanks for having me.
Sam Silvershein:
Let’s start at the beginning. You launched AllegisCyber before venture capital really focused on cybersecurity. What was the insight that originally led you there? And why the full pivot to cyber?
Bob Ackerman:
My background is in computer science, and I was a classic Silicon Valley entrepreneur. I built two companies, backed first by Sequoia and then by NEA. That exposure gave me insight into venture capital.
Gordy Russell at Sequoia nudged me toward VC, and after building my second company out of cash flow—working with strategic corporate investors—I saw firsthand the value those relationships bring.
When I started AllegisCapital, all our capital was strategic. That gave us market insights and customer access, which de-risked our investments.
As the digital economy grew, I saw privacy and security emerging as serious risks. We made our first privacy investment in 2000, our first cyber investment in 2002. Then we realized: with the entire economy digitizing, cyber would become the existential threat. You can’t do cybersecurity part-time—you need deep domain mastery. That’s why we went all-in on cyber.
Sam Silvershein:
That led to DataTribe—how does it work with AllegisCyber?
Bob Ackerman:
It’s all one platform. Allegis focuses on Series A and B, while DataTribe focuses on seed—working with technical founders, often from NSA and national intelligence.
For example, we worked with the founders of Dragos—industrial cybersecurity—right from the seed stage at DataTribe, and Allegis led their Series A.
Sam Silvershein:
What makes the ideal cybersecurity founder?
Bob Ackerman:
Domain mastery. Cyber moves too fast and is too complex to learn on the job. In Silicon Valley, hot sectors attract generalists—cyber can’t afford that. Both founders and investors need deep expertise to anticipate where the threats and opportunities are.
Sam Silvershein:
Let’s talk about AI. How is AI transforming cybersecurity—both offensively and defensively?
Bob Ackerman:
We’re in the hype-and-hope phase of AI. Capital is flooding in, often without discipline. But real innovation is happening.
On the defensive side, AI will dramatically enhance analysts’ productivity—automating data collection, correlation, and analysis.
But attackers are also using AI, which means attacks will be faster and more sophisticated. What took nine months will soon take nine hours. This is machine vs. machine warfare.
Sam Silvershein:
So what risks—and opportunities—are you tracking?
Bob Ackerman:
One huge opportunity is using AI to boost productivity in security operations centers (SOCs). Another is deepfake detection—companies like Reality Defender are key players here.
Network mapping is also critical. With IPv6 expanding address spaces, real-time network mapping becomes essential. A startup called SixMap, built from NSA technology, is leading the charge.
Sam Silvershein:
Which industries are most unprepared for these threats?
Bob Ackerman:
We segment the market into three tiers:
- Fortune 200: Highly targeted, well-resourced.
- Middle market: Exposed but less sophisticated.
- Small businesses: They think they’re too small to be targets—but aggregated, they are.
Critical infrastructure, especially small operators like water treatment plants, is particularly vulnerable. They lack resources, but they’re essential targets.
Sam Silvershein:
Are there specific investment areas you’re most excited about right now?
Bob Ackerman:
Cyber is like life sciences—it never stops evolving. The offense constantly innovates, forcing defense to follow.
We look for what the offense is working on now—because that’s where the threats will emerge in 4-6 years. That’s the innovation cycle.
Weaponized data is a huge emerging concern. How do we validate the provenance of data? Who touched it? Who altered it?
Another big focus is identity—how do you trust a device in a fully connected, autonomous world?
Sam Silvershein:
How do you find non-consensus bets like Dragos?
Bob Ackerman:
Deep domain expertise. You need proprietary insights to see value where others don’t. DataTribe helps us do that.
Sam Silvershein:
Finally, what advice would you give to founders building the next great cybersecurity company?
Bob Ackerman:
Find specialized investors who understand cyber as deeply as you do—partners who bring operational expertise, customer introductions, and a real understanding of the entrepreneurial journey. Capital is a commodity; real partnership is the differentiator.
Sam Silvershein:
Bob, thanks for your time and insights today. Really appreciate you joining Driving Alpha!
Bob Ackerman:
Pleasure to be here—happy to continue the conversation anytime.