Pat Gray, Founder of Risky Business, Joins Decibel as Founder Advisor

We are excited to announce that Pat Gray, founder of Risky Business, is joining Decibel as a Founder Advisor. Pat is well known in the cybersecurity industry as an influential analyst whose podcasts are downloaded >200k times a month. The Risky Business podcast is the #1 show for founders, security researchers, and technical CISOs who want an unfiltered perspective of the most important trends in our rapidly changing industry. Through the years he has helped many successful startups, and shares our passion for helping founders at the earliest stage challenge the status quo in cyber.

In his role at Decibel, Pat will be advising our founders on how to message and position their products and will also be working with our team to incubate and seed new opportunities at the intersection of AI, Cyber, and Defense. We were excited to share his perspectives in our Founder Q&A:

Why did you start Risky Business? What was your original vision?

I'd been a cybersecurity journalist for six years before I started the podcast, and I found writing about security for a mainstream audience frustrating. I wanted to go deeper on security topics than I could writing for mainstream tech publications, and the only way I was going to be able to do that was to spin up my own thing. I wanted to actually express an opinion, which you can't really do in print journalism. I'd done some radio work and always enjoyed it, so I launched a podcast. I wound up publishing my first episode in the same month that Apple launched the iPhone, so the timing turned out to be fortuitous.

The media ecosystem was changing back then, too. I could see the writing on the wall for traditional media business models as far back as the early 2000s and realised it was going to struggle as an industry. I saw an opportunity to do things differently and to work closely with sponsors whose technical approaches I respected instead of accepting advertising dollars from companies I didn't believe in. It's been a more authentic partnership model and it's worked out really well.

You have one of the largest and most loyal followings in cyber - how have you curated your content and audience through the years?  

You have to respect your audience's attention. Don't waste their time, don't flap your gums about what you did on the weekend, and do your best to convey accurate information and informed perspectives as efficiently and entertainingly as possible. A lot of work goes into every podcast we publish. We don't phone it in, and I think that's why we've been successful. We have the highest impact audience in the cybersecurity discipline. We have a crazy amount of CISOs listening, in addition to people doing every kind of meaningful job in cyber.

You have advised many startups through the years - what do you enjoy most about working with founders?

It's great to be around people who want to just do their own thing and create real change. If they see an area where they can do something better, they actually set about doing something and don’t just complain about it. I've worked with a wide range of startups. Some of them needed advice because they were sinking, others because they were soaring. I am also a founder so I know what it’s like to have the highs and lows.

The work is never boring and varies a lot. I've done everything from helping Dmitri Alperovitch (Co-founder of Crowdstrike) build his Geopolitics Decanted podcast to helping HD Moore (founder of Metasploit and RunZero) and his team tune their messaging. I'm working with half a dozen companies at the moment. Now I've partnered with Decibel I'm looking forward to working with founders at an even earlier stage. “Pre Powerpoint”, as they say!

What is your vision for what Risky Biz can become? How will you grow the platform going forward?

One thing we definitely want to do is invest more time in working with emerging startups, practitioners who want to try new things, and founders who are trying to get new ideas off the ground. I will be dedicating more time to that and I'm already working on some terrific new projects that we’ll be announcing soon.

As for the media side of things, we may scale the number of podcasts in our network, run some events, or start offering different types of services to startups. But ultimately Risky Business is an institution and its influence stems from the trust people have in it. So any changes we make there really need to be thought about carefully.

You have been covering cyber deeply for nearly 25 years. How do you think the cyber industry will evolve? Any advice for founders?

It's already changed an awful lot, but the tech that security practitioners have available to them in 2025 is so much better than it was 20 years ago. These days so many startups are being founded by practitioners who actually understand security. This is a very healthy change.  

The types of startups I like serve immediate needs. I always tell Risky Business sponsors: Nobody buys something because it's cool, they buy things that fulfill an immediate need. A new product in security needs to be essential and enduring. Customers want building blocks, not incredibly complicated and mysterious solutions.

I'm also interested in working with startups who are building open and configurable tech that users need and actually understand. As an industry we've pumped way too much money into products that don't meet that definition. There are too many black boxes that aren’t really living up to their promises.  

The venture capital industry is changing rapidly - how do you think you can help the industry evolve?

I've been a cybersecurity reporter since 2001, so I've been pitched every solution under the sun by a never-ending conga line of executives and founders. I've also worked with countless startups through Risky Business over the last two decades, so I've developed strong opinions on what works, what sucks, and what I think will really make a difference. That's where I think I can be useful. You can trust that I will always speak my mind.

Why are you partnering with Decibel?

We always have 10x more vendors that want to advertise on Risky Business than we have space for. A number of Decibel portfolio companies were sponsors well before I even met anyone who worked for the fund. There are some amazing people attached to Decibel and I think it’s because they are specializing in something hard at a very early stage. They have built a track record of investing in the kinds of startups I believe are going to make a difference. We have a lot of ideas for how we can do even more together and will be launching our partnership at the RSA Conference next month - see you all there!