Scale Like a CEO

Scaling & Privacy Compliance Insights with Rich Ruddie

• Justin Reinert • Season 1 • Episode 19

Share episode

Privacy regulations are exploding across the globe, and most businesses are dangerously unprepared. What started as a single state privacy framework in California has mushroomed into twenty different state frameworks in just three years, with new international regulations constantly emerging. Meanwhile, companies are getting blindsided by litigation from laws never designed for the internet age.

Rich Ruddie, founder of Captain Compliance and serial entrepreneur, joins us to unpack this complex landscape with startling clarity. "The lack of knowledge from business owners is almost incomprehensible from a privacy professional's perspective," Rich reveals, describing how companies operate with outdated policies copied from other websites years ago. The consequences? Regulatory bodies are no longer taking a lenient approach, with fines reaching $85,000 for companies that ignore compliance requests.

Beyond the regulatory landscape, Rich shares his entrepreneurial journey from digital marketing to privacy tech, offering a masterclass in building high-performing teams. His "hire slow, fire fast" philosophy ensures only those who thrive in startup culture make the cut. "We like to hire winners because we want that winning mentality," he explains, seeking people who've built successful products and demonstrated achievement throughout their lives.

The conversation shifts to scaling strategies that have helped Rich grow Captain Compliance from a website and an idea to serving major brands in under three years. His secret? Relentless work ethic, strategic networking, and building a community of A-players who can outwork the competition. As Rich puts it: "There's no point in doing anything unless you plan to be a winner and at least top two in any industry you enter."

Whether you're navigating privacy compliance challenges or building a startup, this episode delivers actionable insights from someone who's mastered both. Connect with Rich on LinkedIn to learn more about protecting your business in this rapidly evolving privacy landscape.

Speaker 1:

Welcome to Scale Like a CEO, the show where we dive deep into the strategies and insights of successful entrepreneurs. I'm excited to bring you today's episode featuring Rich Ruddie as the founder of Captain Compliance and a serial entrepreneur, rich brings valuable expertise in scaling businesses and navigating the complex world of privacy compliance. Join host Justin as he explores Rich's entrepreneurial journey, discussing everything from building successful companies to addressing modern privacy challenges. Whether you're a business owner, entrepreneur or simply interested in the intersection of technology and privacy, you're in for an insightful conversation. Let's get started.

Justin Reinert:

Richart, thank you for joining me on Scale Like a CEO. Just to get us started, if you wouldn't mind give us a 90-second intro of you and your business.

Richart Ruddie:

Richart Rudy. I'm based out of Fort Lauderdale, florida. I was born and raised in Baltimore, maryland, came down here for college and never left. Started my career at a boutique hedge fund, ended up learning on the side digital marketing skills, which I've now translated into numerous businesses that I have founded and sold. And my latest and most passionate one my big one here, is Captain Compliance, which is a data privacy and compliance software. So, with all the emerging trends in privacy regulations, with new frameworks and laws, as well as privacy litigation heating up, we are the protector and solution that automates all of the privacy requirements through the use of Captain Compliance and software.

Justin Reinert:

Nice very succinct, so I'm curious what's the biggest challenge in your industry and how are you solving that?

Richart Ruddie:

It's amazing how many companies that we come across and that we talk to or work with that have just no background or understanding of privacy but they're doing things that are breaking their requirements and sometimes it's so blatant.

Richart Ruddie:

And sometimes it's a privacy policy that is from seven years ago that was copy and pasted from another website and they're like is this bad, having something that's not even relevant to our website and giving out false information to our users and not respecting their privacy and what their data rights are?

Richart Ruddie:

That's really the biggest challenge and interesting thing that I've come across in my fairly short time in this industry now is that the lack of knowledge from the business owners and from the staff is really it's almost incomprehensible from a privacy person's and a privacy professional's perspective.

Richart Ruddie:

From a privacy professional to another privacy professional, typically they tend to be very knowledgeable, but the average SME, smb and a lot of the businesses we talk with, and even on some of the enterprise clients we talk with, their lack of knowledge can really be outstanding because they had a marketing person or somebody who came in there who just didn't care. And it's evident now that it's a common trend because the regulators are coming down and early, throwing the hammer down on a lot of the companies that are just not caring or blatantly misrepresenting. There was a Connecticut fine the other day for $85,000. And they said what happened was they made several requests to fix it and then when they told them they fixed it, they blatantly didn't, they just lied about it. So seeing things like that are things that we're seeing as well firsthand, and that's probably one of the biggest surprises in the way.

Justin Reinert:

Yeah, I would imagine it's hard to keep up with it Because I know for a number of years now we've been kind of dealing with GDPR and then we've got the California privacy and different privacy laws popping up, and so, especially if you're doing international business, being able to keep up with all of that has got to be challenging.

Richart Ruddie:

It is incredibly challenging and it also makes it fun and unique, for me at least. I like a good challenge. So we like to say it'd be really hard, if not nearly impossible, for any individual to follow and keep up with every single international and domestic law. Just here in America, we have California as the first state and there was one state privacy framework. If you go back about three years ago, now we have 20. So Minnesota and Tennessee are the newest states that just came online with the frameworks that we have to now follow.

Richart Ruddie:

And then every single week there's news about somewhere new, whether it's a Bermuda or it's Uganda who just recently had its first fine and action against somebody.

Richart Ruddie:

So I follow, I get all the different newsletters and because my background in digital marketing, I love creating content and just going through and reading through what other news headlines are, which there's a lot every single day, and that's been one of the ways that I've been able to kind of keep track. And then our chief privacy officer has been really amazing about making great YouTube videos and educational pieces as well about when there's new laws or things that are really important. I mean we'll give you an idea that there's a law called the californ invasion of privacy act, which goes back 30 plus years ago, and this is a law that was not intended to be written in the law of the internet, but it's being used today to file litigation and what's called private right of action claims against businesses. We had one just yesterday pop up and say, hey, we got hit with one of these claims. We need your help.

Richart Ruddie:

We've done videos and educational pieces about that as well to try and warn and just let people know. Like here's what's happening. It's not just the country frameworks like GDPR or the state privacy frameworks, but it's also these old laws that are being reinterpreted. In this case it's called pen trap and trace, so think wiretapping and devices, and that's being used to file claims. So there's so many landmines every which way you go and it's a lot of work, but that's part of the fun and challenge is being able to figure out the ways to protect clients against every one of these potential claims that could pop up and having a good defense by using our software and our tools.

Justin Reinert:

Yeah, if you like taking on challenges. It sounds like you've got your work cut out for you. I'd love to hear you know so. You have built and scaled a number of businesses, sold some businesses. I'd love to transition and talk a little bit about you know when you, and maybe even we, can start in some of your earlier businesses. You know what are some challenges that you faced as you started to scale that business and grow through people.

Richart Ruddie:

Yeah, absolutely. So we'll go back to when my last businesses was in the digital marketing agency that specialized in reputation repair and was actually the catalyst that led me to finding out and discovering the data privacy software business. So one of the services we offered was data privacy removal. So if we were to google anybody's name plus the city they live in and their home address appeared online, people would ask, hey, can I have my personal information removed from here? And that was one of the services that we offered. So when I saw the emergence of new privacy laws and the data privacy as a business to business opportunity, that's what was the catalyst to say, okay, here's a really good, scalable opportunity of a growing and emerging market. I was looking to actually sell going back to 2017, 2018. I was looking at either a sale or an investment opportunity to see what I could do with the business and ended up having a private equity group out of Provo, Utah. They introduced me to the whole Silicon Slopes area and I said, well, I didn't realize that Utah had such a growing and emerging startup scene, so I was really impressed by that. They ended up having a few different people that they were looking to bring into the company to help run, grow and scale Ended up being that the deal fell apart because the terms didn't make sense. But one of the team members they had brought forward I said you know, if this deal doesn't work, I was really appreciative of all the work and effort you put up front and building out models and things. I'd be interested in moving forward if you would like to. So we ended up hiring that way. So it wasn't from a job board or anything, it just happened to be from a private equity contact. And then we ended up growing and scaling the business more for the next five and a half years from there before I decided to exit and move into this current industry. That's how that one happened.

Richart Ruddie:

And then, after I had the exit, I had a five month transition period. So worked on the transition period was starting to kind of undo my relationships that I'd built for the last 12 years in the marketing agency, and one of the hiring ideas was LinkedIn, right. But then I also had DICE, which is a technical and programming engineering job board. So I made a list of all the different places. The last month of my transition period was May and I'd planned to take my family on a trip to Asia for the month of June, just kind of as a celebration of finally having a little bit of time off. Unfortunately for me. I posted jobs to Indeed, LinkedIn, Dice, the International Association of Privacy Professionals job board, and I just got inundated with job applicants. So pretty much my whole time traveling overseas.

Richart Ruddie:

I'm trying to balance time to interview people and I ended up interviewing about 180 plus people and made a list and highlighted the ones that I thought were the best qualified. A handful of them I ended up working with in some capacity or another between then and now. Some of them just we weren't able to come to the right terms or it just wasn't the right fit. But that was a really fun exercise and it was great because through that hiring process and interviewing process I got to make relationships with people from all over the world that could be good contacts that we've used sometimes, Like, for example, we've had a client who needed Brazil privacy policy language and needed it in Portuguese. So we were able to go to one of the Brazilian attorneys that specialize in Brazil's privacy law and speak with them and have them help with the privacy notice. So from that operation process that worked really well Now I will say we've.

Richart Ruddie:

We've hired some people that were not good fits and we've changed our motto and we now have a higher slow fire, fast mentality. So it should be a long time for us to onboard somebody, because we want to make sure that they're the right fit for the job and if they don't cut it, they're not making it in the first month. We no longer have a let's wait it out and see if they can adapt and get to it. It's let's just cut the bait and let's move forward to somebody who has that startup mentality. We like to move very audaciously in this venture.

Richart Ruddie:

I will say that there have been culture things that I have in my work ethic.

Richart Ruddie:

I always expect more and want to do better.

Richart Ruddie:

That I drive into the rest of the team and I work really hard.

Richart Ruddie:

I'm working on weekends, I'm working on nights, I'm working all the time, I'm working on vacation or what should be a vacation. So not that I expect every single employee to come and give up their vacation time or anything like that, but I want to drive, that we work really hard and if we can outwork any of the competition, that's just one of the many ways that we're going to get ahead and we're going to win, and I instill that now in my interview process whenever I'm speaking with potential hires. And some some love it and they understand the startup grind in the culture, and others say it's not a good fit. I'd rather be at a Fortune 1000 type of company and enjoy my nine to five and that's that and that's totally okay. So it's just good that we have those clear boundaries and we explain that in our culture. We're going to outwork and we work really hard. And some, like I said, vibe with it and love it, and others it's just not a good fit and that's totally okay.

Justin Reinert:

Yeah, it's definitely, you know, in in that kind of startup growth mode it's not for everybody, and so you know definitely being able to filter out the people who who don't want to be in that type of environment. I'm curious, what else as you're hiring, what are some of the other qualities that you're looking for while you're interviewing?

Richart Ruddie:

Yeah. So I was in Las Vegas years ago eight years ago and was sitting with a guy who had a beautiful villa there. He had a very successful commercial insurance business and we talked about what questions you ask when you hire and he said I'd like to know what achievements they've had and what they've won in life. Because we like to hire winners, because we want to have that winning mentality. So that's been something that we implement into our hiring process and asking what have you done, what have you built, what wins do you have? Because it's always good to know that they're going to have wins internally and it's been really cool.

Richart Ruddie:

For example, one of our partners here has built something called a global privacy control plugin and just on the side, unprompted, said this is something that would be really valuable, it's helpful. I'm going to build this on the side for us because it's good for marketing, it's good to have and it's good for our own testing purposes, because I don't like the other software out there. So I wasn't isn't a super technical person, but just went above and beyond to do stuff like that. So I love people who are creators and builders and have created great products and have that winning mentality. So that's that's. That's one of the one of the things that I love to see and that we'd love to ask and then find out what are you an owner at?

Justin Reinert:

That's a great one. So how big is the team now?

Richart Ruddie:

So we're still boutique. We're at about 12 of us total, mostly full-time, a couple people that are part-time and ramping up. Just yesterday we actually had three new clients on board. We're hoping just to keep doing that every day and ramping up.

Richart Ruddie:

I come from a digital marketing background. I started just with a website and an idea two years ago and said, all right, let's start building up a website, let's build some relevant content, let's start building a team and then let's build a product. So the first month was really just architecture building and building out what it would look like. What's the best way to scale, what are certain things that we can build into our product and into our tech stack that will be not only scalable but more feasible. And now what's happening is we're finding that especially some big tech companies are seeing our tech and they're like, okay, this is really good, this is something that we could use and we can run with. We had a company that we're in talks with now that wants to build onto this and has some pretty big name clients, and they were so impressed by the tech and they said, okay, this is the solution we want to go with. They were actually using a consent management solution currently and they said we're going to drop this, not only because we like your tech better, but also we want to partner with you and figure out ways to scale. So that's been really, really fun. As we grow with this, we'll continue scaling up and hiring more.

Richart Ruddie:

I like to be involved still in all the hiring process. It was at Steve Jobs at Pixar said that for the first 600 employees that he was involved in everybody's hiring process and was able to hire all A players for the first 600. He said beyond that, it became really hard to continue with the A player hiring process. So my goal as we scale up I don't know if we'll get to 600. With the use of AI and everything that's been really driving efficiencies here we may not have to get anywhere near 600.

Richart Ruddie:

But at the very least, I like being involved in the hiring process and getting to know everybody and, like I said, making sure that we're hiring winners across the board, because if we can make sure that we don't have dead weight, it doesn't bring other people down. So that's one of the most important things that I always say is make sure that you have a players and that you're not hiring, especially in a tech startup. Obviously, it might be different if it's a retail business or something or food business, but hiring a players with the mentality of winning is a really great recipe that we're seeing in our early stage for success and that I would recommend to others.

Justin Reinert:

Yeah, yeah, hiring those a players definitely key, I'm sure, key in your growth and you know, just have started, you know, less than two and a half years ago, with just starting to build a website and now you've got this team of 12 folks and you're continuing to grow and land clients. I'm curious, a, it's really impressive what you've done and I'm curious what there's the A players component. But what else would you attribute to like if you had to pick another or the number one thing that was critical to your success so far? What, what is?

Richart Ruddie:

that I would say the grind, the hard work. So everybody loves an overnight success and I'd love to say, oh, we just you know, all of a sudden we grew from $0 to $20 million overnight in one year. But it comes not from luck, but just a lot, and there is luck involved, but there is a lot of hard work, grinding, making a lot of contacts, taking a lot of chances, reaching out to your networks. I have a decent network that I'm always connecting with and just brainstorming and throwing ideas out and as they see our success internally, they're saying hey, how can we get involved? How can we refer you clients? How can we help businesses that were investors in? So so that's starting to happen.

Richart Ruddie:

So I will say it just comes from a lot of hard work, a lot of long hours, and doing that in the startup life, which is different from my last business, was kind of. I felt like everything was kind of handed to me in the beginning and because of my strong SEO skills, we were able to track a ton of inbound right from the get-go. But it wasn't nearly as scalable. The business and the way these tech companies are valued versus a more tech-enabled services business are very different. So I get like a dopamine hit every time I see one of these Stripe payments come in. So that's just one of my many motivations that I'm going through every day. It's very exciting. And then, when we have big national names or global names, come to our website and say hey.

Richart Ruddie:

I'm interested in learning more, or we want to do a scan and see all the different cookies and tracking pixels we have on the website. All that just continues to motivate me and excite me, and that's happening every single week now.

Justin Reinert:

That's great. So what's the future? Look like at Katz Compliance.

Richart Ruddie:

Yeah, so I mean we. The late Sam Zell said there's no point in doing anything unless you plan to be a winner and at least the top two in any industry that you enter. So that's the goal just continue growing. We have a kind of attack to continue just growing and scaling in certain verticals. We have a lot of different niches, whether it's CPG companies that have come to us and are really loving our product. So we have a lot of channel partners that we're either talking to or we're starting to grow and scale with. So the idea is to grow it and scale it to have hundreds of thousands of businesses that are using us.

Richart Ruddie:

I was in California the other day and just walking in the lobby of a hotel and somebody left a bottle of water out and it ended up being a company that's a client of ours and I said, oh so cool, just seeing this random bottle of water, which I would never know otherwise because it's growing on the West Coast, isn't as big yet here in Florida and I was like, oh so cool. So I took a picture and I shared it and said you know, I love just seeing seeing this our clients in the wild. And there's another client of ours and he's become a good friend. Yanni Huffington from Lemon Perfect would be a great person interview. He's the Steve Jobs of the water industry is what I say. He is so passionate about his business and he and I were having breakfast one morning in Fort Lauderdale when he was in town and there was a marathon going on in Fort Lauderdale and in the background there's a marathoner and they're walking with a bottle of Lemon Perfect and he goes hey, you see that. He said they're walking with the Lemon Perfect right there.

Richart Ruddie:

And I said that is so cool just to be out here breakfast outside and seeing somebody walking by with your product. That so cool, just to be out here breakfast outside and seeing somebody walking by with your product. That's got to be so fulfilling. So our goal is eventually, when you go to the whole whole foods or you get on the road and you're driving, you see signs. It's for us to point out and say, oh, that's a client. So we want to be ubiquitous in the privacy world and eventually have hundreds of thousands, if not millions, of websites using our software, protecting themselves against the both privacy litigation and privacy regulations in the world and just being the known name as the compliance superhero that everybody can rely and depend on that goes above and beyond for their clients. We're doing that right now, one website at a time.

Justin Reinert:

That's great. I actually I just I had a bottle of Lemon Perfect like a month ago, so I'm familiar with the brand. I love it.

Richart Ruddie:

Yeah, great product, great founder. And I was in New York City a couple months ago catching up with Yanni and I introduced some other entrepreneurs to him and just having a nice roundtable dinner, just talking, shop, talking ideas and business. And they came away so motivated after that and said that was great and I said I should organize and set up some more of these like founders dinners. Another podcast I'd love to recommend is called Founders by David Senra and I've talked to somebody who is who's friendly with him. I said we should set up a founders dinner, kind of like what I did in New York with the Lemon Perfect team and the other guys were in telecom and I think that's something really just networking right and bouncing ideas off people. Having the sense of community is really important. So that's a good thing. And as we grow and scale, I want to eventually have like conferences and weeks where we can bring team both team members and clients together and just brainstorm.

Richart Ruddie:

And we find listening to our clients. We've had some clients who have come forward with literally no commentary. They just want to, they just need to check the box and focus on their business. But we've had others who have given us really good, valuable feedback and we take all that into consideration. And that's one of the other things that we're doing to just accelerate our product. And then it's.

Richart Ruddie:

It's showing when we go and showcase it to another potential client in that niche or vertical and they're saying oh, this is really incredible that you can automate removals. For example, when people create this data subject request and we're like, okay, well, that was the request from a client we built in the end-to-end application and now we're seeing the fruits of that labor and that listening is all coming together. So that's really cool too in our building and growth. And that's how I expect to see all those different signage and companies and say, oh, that's a client, that's a client, that's a client, so it's in the works. And hopefully in five years, when we're connecting again, you'll say, wow, you've accomplished it. I love that one.

Justin Reinert:

I love the community that you're focused on building. It's great If folks want to get in touch with you. What is the best way to do so?

Richart Ruddie:

Yeah, definitely recommend LinkedIn. It's a great way to connect. We're on there, we're connecting with other privacy professionals and non-privacy professionals, entrepreneurs all the time, and we have a YouTube channel which I can share, and we're always sharing great videos about different privacy laws, privacy regulations and just information that really helps the average person learn about privacy, and Alex, our chief privacy officer, loves sharing this content and is active with it, so it's really great, and we also have a couple of webinars that we're working on rolling out, so, if the timing fits, we can always email you and update you with any sort of webinars that we're doing.

Richart Ruddie:

Just we're working on one right now about privacy litigation that's happening in a couple of weeks.

Justin Reinert:

That's great, Richart. Thank you so much for joining me today.

Richart Ruddie:

Yeah, this was great. Thank you for having me, and I'm glad I could join.