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Join Darren Gallop as he shares his unique perspective on entrepreneurship, cybersecurity, and the intersection of work, life, and travel. A linguist, musician, and world traveler, Darren brings a diverse background to his experiences building a startup. Tune in as he delves into the challenges and triumphs of being an entrepreneur, offers insights on the field of cybersecurity, and reflects on the ways in which his love of language and music have shaped his journey. Whether you're an entrep ...
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Caffeinated Risk

McCreight & Leece

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The monthly podcast for security professionals, by security professionals.Two self proclaimed grumpy security professionals talk security risk, how they’ve managed it in the past and forward looking discussions with guests working in information security and risk management.
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Welcome to the AJ Osborne Podcast. Twice a month, I’ll sit down with guests or fly solo to share incredible stories, give my take on today’s economy, and show you how to build wealth the right way. We bring high-value guests - solely for the purpose of long-form, high-impact discussions. By working together, we can build a better future for ourselves and our families. Find our video podcast on YouTube: https://www.youtube.com/playlist?list=PLoaCszL7eN9T7EixaJgL49WTLsT-CWLD1
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In this episode, I’m opening up about my political views for the first time and discussing how U.S. policies shape wealth building, personal finance, and investment strategy. I’ll cover everything from the effects of inflation on generational wealth to the economic divides between states like California and Texas. My goal is to give you a clear loo…
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Disclaimer: This video contains discussions about hunting and the hunting industry, we understand this may not be suitable for all viewers. In this episode, I dive into how I acquired a struggling business in the hunting industry and managed to triple its sales within weeks. With decades of entrepreneurial experience, I share why I believed this ac…
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Technological change is inevitable and often one of the aspects that attracts people toward careers in information and operational technology. Although risk management is a part of navigating advancement in any area, the fundamental flaw in any management system is our human tendencies. This episode explores how organizations can make slow, steady …
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Real estate investors and entrepreneurs: if you pay attention to what today’s guest explains, your wealth, revenue, and successful decision-making will explode. This is something I’ve personally found evidence of while running multiple businesses, and even though it seems simple, it can have profound effects on everything you do. If you get this ri…
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For years, I thought every American should be investing. After all, it’s the American dream to work hard, build wealth, own property, and lead your family to financial prosperity. But I’ve changed my tune after recent events, probably for good. I no longer think most Americans can handle the pressure of owning businesses, real estate, or an extensi…
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Whether it's the NIST CSF, 8276 or the new European Cyber Resilience Act there is no denying the expectation that supply chain management (SCM) is a risk management area no organization can ignore. While SolarWinds is recent common reference in many SCM discussions, this episode's guest takes us back to Target's major data breach that resulted in s…
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After another 80-hour workweek and realizing his kids’ lives were passing him by, Spencer Hilligoss knew he needed to start making passive income. The problem? His time was chained to his tech job’s high pay and long hours. Spencer loved what he did, but the job took away more than he was comfortable with. He hadn’t seen his young son in weeks, and…
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Long before the Matrix captured peoples imaginations, Winn Schwartau was steadily offering red pills for those reading his many books on information warfare. A scholastic level researcher without the pretense, Mr. Schwartau has been recognized internationally as one of the leading security thinkers of our time and has a special capability for disti…
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Will the US dollar be replaced? Could we be on the cusp of de-dollarization as more and more countries search for reserve currency alternatives? Is America’s spot as the number one economy in the world up for grabs? Emmanuel Daniel, entrepreneur, advisor, founder of The Asian Banker, and author of The Great Transition, is on the show to discuss the…
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Nick Lavery, Green Beret and Army Special Forces member, has been shot, blown up, and beaten down. After an insider attack in Afghanistan left him without a leg, Nick wasn’t supposed to return to the Army. He’s had over thirty surgeries, lived with excruciating pain, and had his physical power taken from him. But now, he’s back, and he’s had to ada…
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We’re on the cusp of the biggest investment opportunity since the 2008 crash. Investors are fleeing from real estate, scared of its apparent risk, but in a couple of years, they’ll be the same investors wishing they had bought NOW. And this isn’t just theory. We’ve been buying deals at MASSIVE discounts that could make us unprecedented returns over…
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Almost all incident response plans include a "lessons learned" step, and in the post adrenalin phase that follows many breaches, reviewing what worked and what needs improving doesn't excite a lot of people. Adam McMath is clearly the exception, leading incident response activities in both the cyber realm and physical. How do resilience and inciden…
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Amongst the industry verticals classified as critical infrastructure, few would argue that telecommunications belongs in the top that list, placing even more weight on a risk management program due to cascading impacts. Consequently, safe reliable operations are essential for success while continuing to grow in a highly competitive marketplace. A s…
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Real estate is a touchy subject: tenants and landlords don't like each other. Tenants believe they are subservient to them, and landlords believe they SHOULD be. Or are the perceptions of each side drastically different than the reality? In addition, why is our school system so flawed, that most people aren't taught about the best way to make a liv…
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Regulatory frameworks from PCI-DSS to NERC-CIP to the newly minted NIST CSF 2.0 each require organizations of all sizes to have cyber incident response plans. Most of us who have spent any time in cubicle filled office towers are familiar with fire drills to clear the building and gather staff at muster points, and that is as close as we get to the…
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Cybersecurity is highly technical. You and I probably would not be able to understand a lot of the terms or systems or coding behind it. But revolutionary improvements come from the practical application of technology. So, how do we leverage the tech available to us in our own personal and professional lives? Is it truly the next step for modern bu…
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Avery and her husband had a great idea one day to purchase a home and to rent it out, in hopes that one day, they will be able to help fund their kids' education with the income. They didn't even know this was known as "Real Estate Investing." At the time, there was no such thing as podcasts or courses to talk about this. This idea then morphed int…
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Real estate investing has two forms: active and passive. Passive is what most people think of when you say real estate investing, where you buy an asset, and it generates some sort of cashflow for you. Active investing takes this and applies the principles of business, including scale, value-add, management, and more. Today's guest, John Klingelhoe…
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Those running a business today who have not experienced disruption due to cyber issues or attacks know it is only a matter of time. Even if their organization is not directly targeted, the modern marketplace comprised of multiple, interconnected supply chains, means impact is unavoidable but this episode's guest, Steven J Ross contends planning, de…
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Can luck dictate one's success in business? Absolutely. But looking at another's success or luck does not mean that you lose something in exchange. Luck is something I fully believe can be CREATED. For example, when I was paralyzed and stuck in a hospital bed, many may say - how is that lucky? That seems like terrible luck. But looking back today, …
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2024 is yet another pivotal election year for the United States. But if we've learned anything from the last few elections, there is a tremendous amount of fearmongering, noise, and propaganda that can result from a journalistic system incentivized by money and clicks. This is why I'm HYPER-aware of anything that intends to change or influence my p…
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The U.S. Security Exchange Commission defined new rules for cyber risk matters facing publicly traded corporations in July of 2023. Although the SEC's mandate is limited to publicly traded companies in the United States, where one regulator goes others are apt to follow. Brian Allen is the co-author of a brand new book putting form, structure and t…
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My dad, Ron, lived in a time where mortgage interest rates were 18% - the highest in US history. He assumed he would never be able to own a home, and he would be renting forever. He had friends going down to the bank to get 12% interest on a Certificate of Deposit (CD). It was absolutely bonkers. He was just trying to get started, as a young man. T…
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The US had a huge role in shaping the world the way we know it today. It's role in international wars, politics, and economics has been astounding, particularly for a country so young. It's done a lot of bad, it's done a lot of good. But with the way the world is today...is the era of "good" over? Let's talk about the assumption that the way we per…
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Capitalism is a function of money - the economy. It’s all about serving other people. What you can trade, what you can offer or sell, what problem you can solve for a certain price. As a society, we put a lot of focus on the consumer side - or “consumerism” - of capitalism. The never ending cycle of making money and spending money. And it impacts u…
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After multiple, back-to-back surgeries, Mauricio was in the hospital for 5 weeks. But he had a law firm to run, and was working out of his laptop in his hospital bed. This proved to be unsustainable and unhealthy. But far too often, entrepreneurs think of their own abilities as the only way to get something done. When it comes to business, that's a…
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The Fed announced several rate drops that could possibly happen in 2024, quite the surprise since they hiked rates dramatically to fight inflation not so long ago. What does this mean for the American Economy? In this episode, we will discuss the ramifications of these interest rate changes, updates to the monetary policy, the aftermath of the year…
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Selling health insurance is not glamourous by any means. But that' what my dad and I did for years and years. It felt great for a while. My success and income was based on how much I sold. It felt like I was my own boss. But I got stuck on this treadmill. Eventually, I wanted to grow faster, and faster. I got greedy and prideful. Wanting more isn't…
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The ISA 99 standards body is one of the most recognized authorities on cyber physical security covering many aspects of a cyber security management system for industrial control systems including risk management. This episode features John Cusimano, former chairman of the ISA subcommittee responsible for authoring the risk management portion of the…
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Housing prices are up. Food prices are up. Everything is up, and life can seem bleak. But just how bad is the American economy doing, really? As we know, news headlines about recessions and high interest rates can cause a lot of stress and worry. But the mainstream news reports don't always reflect reality. In today's episode, we cover the hard tru…
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Companies are hurting right now. The market is TERRIBLE for investors and business sharks alike. But the truth is, "you don't know who's swimming naked until the tide goes out" - Warren Buffett. But the United States remains a top choice for investors even during tumultuous times. It's legal structures and consumer laws still are lucrative for many…
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Security and crime are often in close proximity but not always studied together. This month's episode features Martin Gill a criminologist who made the study of crime and security his life's work. After a decade as a lecturing professor at the University of Leichester, Mr. Gill started Perpetuity Research in 2002 and continues to provide very high …
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Financial freedom is a matter of creating an income that can support your lifestyle without consuming all of your time. For most people, financial freedom seems unattainable because of how jobs are set up. The 9 to 5. Research suggests that over 85% of all entrepreneurs (the successful ones) would be paid MORE if they took a 9 to 5 job versus doing…
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News flash: you won't get financial freedom by buying a house. There, I said it. It's the harsh truth. You might be able to with 20 or 30 properties, but then who's going to manage it for you? Are you making enough to hire a property manager? Can you keep up if you don't? I learned this truth the hard way. The job I wanted to quit, the business I w…
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Real estate is more expensive than ever, and the Fed's efforts to bring down inflation are hurting the very people they said they would help: the middle class. Your average home sale price has been astronomical for the past few years, with the new interest rate hikes creating even more of an affordability crisis. It's only a matter of time before i…
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Want to take advantage of todays market conditions with us? Invest in our opportunistic Fund 2 Here: https://cedar.cc/invest In this episode, we're discussing the myth of being "self-made." Are there any successful people that got there completely on their own? We're diving into the behind-the-scenes of the business world, using my portfolio and co…
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Chris Voss is a former Lead FBI Negotiator and dynamic speaker who debunks the biggest myths of negotiation. And he has been seen on Forbes, Time, CNN, Fox News, and more, and is author of Never Split The Difference©. One of his golden rules for negotiation is: "Thou shalt not envision only one outcome." This is true for your personal life, career,…
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Within any organization, leadership is essential to a functioning team. Sometimes, changing how a leader leads their team is required to achieve success. But change hurts. Change is uncomfortable. Change is subjective. Politicians are a prime example of what NOT to do. They make promises that they don't follow through with. They enact policies that…
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China is one of only major world powers that has somehow integrated communism and capitalism - two ideas traditionally thought to be incompatible, even the antithesis of each other. Their economy can truly be considered a modern marvel, having grown exponentially over the course of just 50 years. But it's not all good: their economy has fluctuation…
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Post GSX conference, which included an in-depth review of ESRM and an interview with former U.S. president George W Bush, this episode considers how enterprise security risk management has stood the test of time as well as how risk analysis will need to evolve . Financial receptors can be found in almost every organizational risk matrix but how do …
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On Wednesday, 9/20/23, the Federal Reserve decided to hold rates steady while indicating expectations of one more hike before the end of the year. Although we are seeing a steadying of inflation, it still continues to grow. I invited my friend, J Scott, who is a fellow podcaster, author, and real estate investor, to join us and explain what this me…
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Risk is one of the fundamental factors in creating a successful business. I change a lot and I'm willing to lose money to move my industry forward. What happens if you create something that is not accepted by the market? When investing, I look for proven and measurable assets, not risking for the sake of change. What are some of the unique factors …
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Devon Kennard's successful NFL career have him an unique perspective about money: he was now the stereotypical athlete that made a lot of money and had the ability to spend it in an instant. But he refused to take part in this stereotype. He was determined to invest his money, and then use the passive income on the things he wanted. He wanted to KE…
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In this week's episode of "Why I am Still Awake," host Darren Gallop delves into the critical domains of Human Resource Security and Identity and Access Management (IAM). Learn how these areas are essential for securing not just your business environment but also your personal life. Darren unpacks various controls and best practices within Human Re…
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Starting out in real estate can be daunting. One of the first steps is to choose a market you want to invest in. There are many Midwestern, midsized markets that are being affected by higher interest rates. How will it react? Date the rate, marry the house - this is Craig Curelop's strategy, which he has used to acquire over 100 deals in his first …
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The convergence buzzword has come and gone and some organizations have struggled to reap the benefits of physical and cyber security departments working in tandem toward common goals. Michael Lashlee, deputy Chief Security Officer at Mastercard, shares security insights from the US Marines, secret service and financial services tech giant Mastercar…
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Investing opportunities are everywhere in the US. There is so much access to monetary and other support systems - and the opportunity might not be here for long. Today we're talking with Alfonso Cuadra, who is an immigrant, international investor and asset owner. We're outlining some of the different challenges and differences between North America…
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In this episode of "Why I am Still Awake," we delve into the essential realms of Privacy (PRV) and Data Management (DM), two core aspects of information security and data privacy tailored for small and medium-sized businesses. Join us as we explore the domain of data privacy, unpacking several common controls and key elements such as consent, accur…
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Entrepreneurs made the world what it is today, will they take us to the next stage? Just one generation ago, being an entrepreneur was laughable. You had to buy a brick and mortar building, buy inventory, and spend hours in a library researching. Now, all of that has changed. You can start a website, sell online services, and find answers in a matt…
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The market will either make you or break you. We can't predict when it will or what it'll do, but we can look at the patterns and be prepared. In this episode, I dive into my investing thesis - what do I look for in an industry that spurs me to invest? What are the indicators that tell me, is this a good investment or not? Also, we discuss protecti…
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