
Unlearn
The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.
Latest episodes

Jul 3, 2024 • 36min
Leading with Servant Leadership and Gratitude ft. John Marcante, Vanguard’s former CIO
Leadership is about embracing the process of unlearning outdated practices, fostering a culture of continuous improvement, and aligning your team with visionary goals. Today's guest, with his esteemed 29-year tenure at one of the largest asset managers in the world, Vanguard, shares how he successfully navigated this journey.John T. Marcante is a renowned technology and business executive with expertise in digital transformation, business strategy, financial planning, and cybersecurity. He is the US CIO in Residence at Deloitte, providing strategic guidance to clients and leadership.Previously, John was the Global CIO at Vanguard, where he led digital transformation and drove growth to $9 trillion. He modernized Vanguard's technology and promoted an inclusive workplace. He also developed Vanguard’s global advice platform, making financial planning accessible to millions.John has contributed to the WSJ CIO Journal and Harvard Business Review. His awards include Business Insider Top 50 CIOs and ORBIE CIO of the Year. He holds degrees from The Pennsylvania State University and Saint Joseph’s University.Host Barry O'Reilly invites John to share his journey at Vanguard and beyond in leadership, culture transformation, and gratitude. Inspired by his father's legacy in technology, John discusses how he aligned tech with business goals at Vanguard. Barry highlights John’s approach to direct client engagement and open feedback. They also explore John’s commitment to servant leadership, maintaining company values, and his future goals of mentoring new leaders and giving back to the community. This episode offers personal insights into what drives effective leadership with gratitude.Key Takeaways:Leadership and Transformation: Transformations should align technology initiatives with business goals, led by C-suite executives.Servant Leadership: Building a culture of servant leadership is crucial for successful transformations.Client Engagement: Direct client feedback, really listening and a take-action approach are essential for quick and effective improvements.Maintaining Values: Sticking to core values and supporting clients and employees ensures long-term success and engagement.Future Aspirations: Coaching future leaders, staying engaged in technology, and giving back to the community are key aspects of making a positive impact.Additional Insights:Personal Influences on Leadership: John’s father played a crucial role in sparking his interest in technology and instilling values of gratitude and support.Handling Client and Employee Relations: Prioritizing core values and employee well-being, even when making tough decisions like firing abusive high-net-worth clients, ensures long-term success.Learning from Mistakes and Building Trust: Creating an environment of trust and open communication allows employees to voice opinions and make mistakes, fostering innovation and continuous improvement.Episode Highlights:00.00 - Introduction to the episode02:58- John's reflections on recent thoughts and his father's influence on his career"I think the last thing that popped in my head since we just went through Father's Day, as I was kind of reflecting on my own father…"05:29- Cultural transformation and leadership at Vanguard"So I think I go back to a point you just made, which is, if this transformation is a technology transformation, if it's a technology initiative, then it's already lost, right? Because nothing's a technology initiative. Everything is, a business, a client transformation and that alignment..."05:53- Leadership and servant leadership in transformation"I always felt like that the transformation was a C-suite and CEO-led transformation. You know, technology, lean, agile. They'll roll out across the company, not just in technology, but across the company really took that level of focus and alignment."15:00-Engaging and aligning with clients"if you want to drive engagement and give a group of people an outcome that's meaningful to clients and give them access to clients, and you said, yes, it's a wonderful when they when they could do something, they see the impact."15:21- Feedback on improving processes and client satisfaction"And if you have a nimble, very, very nimble foundation that allows you to very quickly take that feedback and turn it."18:38- Dealing with high-stakes decisions and maintaining company values"Not every business is good business. Stick to your mission and purpose, and always have your clients' and employees' backs."20:47 Discussing the importance of mission alignment in leadership"It's also you feel connected to the mission of the organization. Like what I do every day has to be connected. But the mission, I have to sleep well at night knowing that the company has my back, but more importantly, that I'm actually doing good for society."21:45- Personal anecdotes on handling client interactions and maintaining values"this is one of the things I think that, uh, again, it shines about the company. Like sticking to the values, leaning into your principles, I know, and making tough decisions around that.."23:52- Building Trust Through Commitment to Solutions"And even if you don't know the answer that you know you're committed to getting the answer, I think you then build trust in the organization."25.45- Servant leadership and employee engagement"If your intention isn't good and you make a mistake, well, then we'll deal with that later, right? But if you're doing work for a client and your intention is good that you have nothing to worry about, even if it goes south..."32:34- Embracing Grace as a Core Mission in Leadership"I think as a father, that's our mission as a leader. That's our mission. Like, be gracious, you know, be gracious even when someone doesn't hit the record button"35:09- Transitioning into a new chapter and future plans"I want to be part of, uh, coaching and developing the next generation of leaders that I want to be part of that team, whatever team that is. Count me in, because that was the best part of my job. Second technology. I mean, like, come on, like, I mean technology, AI, generative AI."FOLLOW OUR GUEST:◦ Profile- https://www.linkedin.com/in/john-t-marcante/◦ Deloitte- https://www2.deloitte.com/us/en.html◦ Website- https://marcantejohn.wixsite.com/technologyleadershipFOLLOW THE HOST:LinkedIn: https://www.linkedin.com/in/barryoreillyPersonal site: https://barryoreilly.comFacebook: https://www.facebook.com/barryoreillyauthor/Twitter: https://x.com/barryoreillyInstagram: https://www.instagram.com/barryoreilly/Email: hello@barryoreilly.com

Jun 19, 2024 • 35min
How AI is Transforming Startup Investment Decisions with William Carbone, CEO & co-founder of Evalify
AI is transforming the world, and William is working on how IP is impacted in an AI world… William Carbone is an AI expert, former IBMer, and now a seasoned entrepreneur with over a decade of experience in aerospace, quantum computing, and AI.At IBM, William’s main focus was to identify opportunities, driving business & technology strategies and roadmap for the industries worldwide. He led the Business Development for IBM's Global Automotive, Aerospace & Defense industries. Currently, William is the CEO and co-founder of Evalify, a flagship venture under Nobody Studios, and the CEO and co-founder of The Adjacent Possible. He also serves as the Program Director for the Master in AI at the Rome Business School (RBS) and advises the European Commission as a senior consultant. From creating an innovation studio to developing cutting-edge tools for intellectual property assessment, His work spans Quantum, Spacetech, AI, and various domains.In this episode hosted by Barry O’Reilly, William discusses his journey, including his transition from corporate life and the transformative experiences that shaped his entrepreneurial path. He delves into the practical aspects of innovation and intellectual property, offering advice on navigating these complex areas. This episode is packed with insights for anyone looking to improve their approach to entrepreneurship and understand the value of mental health in the process.Key Takeaways from the episode include:Entrepreneurial Journey: The transition from corporate life to entrepreneurship involves significant rewiring of the brain and requires navigating uncharted territories with curiosity and resilience.Parallels with Music: William's self-taught journey as a pianist highlights the importance of playfulness and self-expression, which he parallels with the creative process in entrepreneurship.Innovation and IP Assessment: William discusses the development of a tool that evaluates the patentability and intellectual property risks of startup ideas, providing investors with quick and affordable insights.Unlearning Traditional Methods: The necessity of unlearning conventional approaches to intellectual property and embracing new technologies and methodologies to stay competitive.Mental Health for Founders: The critical importance of mental health for entrepreneurs, with William sharing his experience of attending a silent meditation retreat to find clarity and balance.Future of Intellectual Property: The potential of AI and advanced tools to democratize access to intellectual property insights, helping entrepreneurs and investors make better-informed decisions.Additional Insights:Leadership and Innovation: This episode emphasizes the role of leadership in fostering a culture of innovation and collaboration within startups.Role of AI in IP: The discussion involves the advancements in AI that have made tools like E-Verify possible, highlighting the transformative potential of these technologies in the intellectual property space.Practical Applications: This episode provides insights about real-world examples of how the IP assessment tool has helped investors make quicker and more informed decisions, reducing the risk and enhancing the potential for successful investments.Episode Highlights:(00:00) Introduction to the episode (01:25) Importance of rewiring the brain and transformative journey of entrepreneurship [01:43] “There is no one making things for you… You have to take the tools on the way and find the way.”(02:23) William shares parallels between learning music and his entrepreneurial journey[3:53] “Music has always been there for me in the journey, even in difficult times or more challenging situations.”(05:14) Barry discusses the importance of following curiosity in entrepreneurship[7:39] “There was a lot of untapped potential in that space, like in billions of dollars that have been spent on patents that have been just never commercialized…”(08:35) Introduction of E-Verify and its capabilities in de-risking investments(11:43) The evolution of AI and its impact on intellectual property assessment[13:22] “But the biggest unlearning there was how to make the industry, to unlearn how they approach LLP. That was the biggest challenge, right.”(13:23) The challenges and benefits of helping the VC industry unlearn traditional approaches to IP [14:27] “I would say the biggest challenge for us and for the investors is to understand that the IP can be a valued friend and partner…”(15:17) Barry shares his experiences with continuous delivery and automation in software development[17:34] It's not that we're taking the humans out of the process, it's we're allowing them to focus on high-value tasks…”(19:10) The concept of patent viability assessment and its impact on investment decisions [21:13] “So these are all great indicators that are simply not available, or maybe no one has the intuition to look for them and find competitors for a startup.”[22:03] “Some investors will tell you.. revenue speaks louder than IP. Others say, okay, IP is so fundamental.”(24:13) William's vision for the future of IP and entrepreneurship[25:29] “There is already a populated market in the direction that you haven't seen before with your business analyst.”(26:27) The democratization of patent information and its impact on founders and investors (30:39) William's entrepreneurial journey and the importance of mental health retreats[30:48] “Actually what is not so much covered is mental health or founders - I would say that's the number one priority.”(33:29) The importance of balance and intention in life and work[34:48] “We live in the attention economy, like everything, trying to grab our attention.”(35:35) Conclusion and final thoughts from Barry and WilliamFOLLOW THE HOST:LinkedIn: https://www.linkedin.com/in/barryoreillyPersonal site: https://barryoreilly.comFacebook: https://www.facebook.com/barryoreillyauthor/Twitter: https://x.com/barryoreillyInstagram: https://www.instagram.com/barryoreilly/Email: hello@barryoreilly.comFOLLOW OUR GUEST:William Carbone: https://www.linkedin.com/in/williamcarbonePersonal Site: www.williamcarbone.com

Jun 5, 2024 • 38min
Who Does What By How Much with Josh Seiden
The definition of success can change everything. Properly defined, you have an agile organization where each team member can contribute fully. Poorly defined, you have stagnant teams and users that don’t like the products. In this episode of the Unlearn Podcast, host Barry O'Reilly sits down with Josh Seiden, a sought-after designer, strategy consultant, and coach. Together, they explore the importance of understanding user behavior, how that behavior can be translated into goals, and how company alignment on Outcomes and Key Results can drive business outcomes. Josh Seiden has collaborated with top-tier brands such as PayPal, Johnson & Johnson, and 3M. His expertise lies in launching and building innovative products and services, as well as fostering agile and entrepreneurial mindsets within organizations. He is the author of “Outcomes Over Output” and co-author of “Who Does What By How Much,” "Sense and Respond," and "Lean UX," all cementing his reputation as a thought leader in the field of user-centered design and business strategy.When User Experience Became DesignWe know now that understanding how users will experience a product is a critical part of designing a new product, but back in the 90’s when Josh began his career in the industry, it was a radical idea. "A friend told me, 'We’re hiring designers here,' and I laughed, 'Why are you telling me this? I’m not a designer.' But that thing you’re doing here, we call that design," Seiden recalls. This unconventional designation became an entire industry, and his unconventional path to it meant he brought a unique perspective to the field of user experience design. Barry notes that this is a story that gets told again and again on the Unlearn podcast; that the conventional wisdom on how to find or become an expert is often wrong.Don't Forget Why You’re Building What You’re Building Barry points out that companies often measure things like the speed of production, but forget to measure the consumer behavior change that would really demonstrate the value of the project. Josh explains that measurability is important over the life of a project, but keeping the focus on outcomes for actual people is the most important thing to track. This is the key premise of Outcomes over Output that answers the question: what is an outcome? Josh’s definition, “An Outcome is a measurable change in user behavior that creates value.” If you need to identify the outcome you should be measuring for your company, answer three questions: Who?, Does What?, and By How Much?The Evolution of OKRs in Large OrganizationsDesign thinking works at the team level very easily, and as the industry developed the question became how to do it at scale? Objectives and Key Results (OKRs) have emerged as a tool for helping large organizations work in agile ways. Josh explains how OKRs can be used to manage outcomes at scale: “The O is an objective. What's the big audacious goal? And then the KR is the result. How do you measure it? The key result. For most people who look at the system, they understand that [...] you want those Key Results to be outcomes." This way of thinking helps large enterprises maintain focus and drive impactful results by clearly defining and measuring success as it matters to the people using the product.Read full show notes at BarryO'Reilly.comResourcesJosh Seiden on the Web, LinkedIn, X, Medium

May 22, 2024 • 40min
How to Build a Venture Studio with Ben Yoskovitz, Founding Partner at Highline Beta
Ben Yoskovitz, founding partner at Highline Beta and author of Lean Analytics, dives into the dynamic world of venture studios. He shares his journey from early failures to building successful startups, emphasizing the importance of community and learning from mistakes. The conversation highlights Lean Startup principles and the significance of solving real user problems. Ben also discusses team management and scaling strategies, revealing how recognizing individual strengths is crucial for success in the startup landscape.

May 8, 2024 • 39min
Overcoming the Illusion of Innovation with Elliott Parker, CEO of High Alpha Innovation
Join host Barry O'Reilly and guest Elliott Parker, CEO of High Alpha Innovation, as they discuss unlearning traditional practices to drive growth in corporations, the importance of embracing new ways of thinking, and the value of exploring alternative paths to foster innovation. Parker shares insights on challenging metrics, evolving creativity, and achieving significant objectives through randomness to spark breakthrough innovations in both personal and professional settings.

Apr 24, 2024 • 37min
The Power of Fractional Leadership with Renee Hawkins
What problem are you trying to solve? Is it even the right one? In this episode of Unlearn, host Barry O’Reilly is joined by Renee Hawkins, a skilled technology and transformation practitioner. Together, they discuss problem solving, aligning business strategies with purpose, and how to pivot your organization successfully. With practical tips on networking, market research, and seeking advice, Renee offers a roadmap for anyone looking to make a meaningful impact in the business world.Renee Hawkins, a technology and transformational practitioner with over 25 years of experience, brings a wealth of knowledge from her time at Thoughtworks and her current role as a fractional COO. Renee's approach of asking for help, networking, and continuous learning serves as an inspiration for aspiring fractional leaders.The Influence of Thoughtworks and Roy SinghamDuring his time at Thoughtworks, Roy Singham was a visionary leader who influenced Renee’s entire approach to business. Roy led with purpose and kept social justice and inclusivity top of mind, which made Thoughtworks an incredible organization, internally and externally. When you take time to study the impact of influential leaders like Roy, you can gain insights into creating a culture that drives innovation and fosters a sense of purpose among your team.Transforming Business ModelsTo deal with the challenges and leverage the opportunities of changing a business model, you need to ensure that your team, operations, and value stream are consistent with the new goals of your business. When you divide the transformation process into achievable steps and concentrate on urgent needs, you can manage complicated changes and prepare your company for success.Building Effective Communication StrategiesCommunication is essential for keeping teams on the same page and achieving business outcomes. Renee values storytelling, honesty, and frequent updates as ways to keep everyone updated and involved. By using effective communication methods, such as weekly reports or town hall meetings, you can make sure that your team remains in sync, inspired, and oriented towards common objectives.Embracing Fractional Work and Portfolio CareersWorking fractionally and having a portfolio career can be very advantageous in the changing world of business today. Renee tells us how she went from conventional roles to providing fractional assistance to various companies. By being flexible, learning constantly, and exploring different opportunities, you can use your skills in different projects and sectors while keeping a good balance between work and life.ResourcesRenee Hawkins on LinkedIn

Apr 10, 2024 • 45min
The Thriving Team Playbook with Dom Price, Work Futurist at Atlassian
They say those who don’t learn from the past are doomed to repeat it. As true a statement as it is, it’s missing one crucial element. If you never confront the reality of the present and get to the heart of why you are where you are, you won’t be able to unlearn the habits that got you there in the first place. In this episode of Unlearn, Barry O’Reilly talks with Dom Price, Work Futurist at Atlassian, who shares insights on facing the reality of the present, unlearning outdated practices, and embracing new ways of working to drive meaningful change and growth in organizations. Dom's early work experience started in London at Deloitte, where he spent three years as an accountant. His job left him unfulfilled and passionless, but that all changed over sushi. Don’s boss at Deloitte offered him the opportunity to work in either New York or Sydney. Despite the allure of New York's size and boldness, Dom chose Sydney for its smaller team environment, where he could have a more hands-on, full-stack experience. This decision marked the beginning of a diverse and interesting career journey that eventually led him to Atlassian.Embracing Reality and Unlearning Past PracticesDom highlights the importance of facing the honest reality of the current situation in organizations. When leaders truly acknowledge where they are today, they can pay homage to the past while also identifying areas that need to be unlearned or improved. Not only will this allow those leaders to eliminate what is holding an organization back, it will also shine the light on what is exceptional and should be elevated. Taking this approach will help break away from average practices and strive for continuous improvement.Collaboration Over SilosBarry and Dom discuss the significance of breaking down silos within organizations to foster better collaboration and communication. This begins with recognizing that the entire company runs day to day on the hundreds of small tasks that require input from every team member and department. When collaboration and breaking down silos becomes a priority, a company can enhance its efficiency, productivity, and overall effectiveness. Equally as important, this type of culture honors the diverse perspectives they bring.Seeking Growth and Avoiding PlateausOver time, companies trend toward mediocrity and status quo, but Dom stands firmly against the plateaus that seem inevitable. There is always a place for growth and improvement, and it requires each person involved to challenge themselves, step out of comfort zones, and actively seek new opportunities. Instead of complacency, a mindset of continuous learning, adaptation, and growth will ensure excellence and innovation.Practical Change Initiatives Over Theoretical TransformationsDom discusses the pitfalls of theoretical transformations, such as Agile transformations, that lack a clear understanding of the underlying goals and realities of the organization. Instead, he advocates for practical, action-oriented change initiatives that address specific needs and challenges within the organization. By focusing on tangible outcomes and being honest about real issues, companies can drive sustainable change and meaningful progress.Balancing Heritage and InnovationNot all of a company’s past should be unlearned, nor should its achievements be forgotten. There is a balance to strike between an organization’s rich heritage and the need for innovation and adaptation. Dom shares how companies can find a balance between honoring the past and embracing innovation, and companies can leverage their heritage while staying relevant and competitive in a rapidly changing environment.ResourcesDominic Price on LinkedIn | Atlassian

Mar 27, 2024 • 35min
Blockchain and the Future of Decentralized Societies with Anne Connelly, Blockchain and Cryptocurrency Expert
Anne Connelly, blockchain expert, discusses transitioning from nonprofit to blockchain, embracing risk for innovation. She highlights the transformative power of blockchain in redesigning society, encouraging risk-taking for personal growth. Topics include decentralized governance, DAOs, and starting small in cryptocurrencies.

Mar 13, 2024 • 35min
Tech Nuggets with Daniel Henry, former Global CTO at McDonald's
Would you be willing to take on mission critical, make or break projects as your career? How would you handle the challenges that arise from situations like bankruptcies and mergers while managing the extreme pressure that comes from such high stakes?Daniel Henry doesn’t just take on high stakes projects as they arise. He actively seeks them out. Daniel’s fascinating career has spanned EDS, American Airlines, and most recently, CIO at McDonald’s. He has gained invaluable insight in building teams, developing leadership, and taking on hard things to help you grow. And one of the best insights he offers is how to make big problems small.Embracing Simplicity in Problem-Solving at Large CompaniesIn the realm of large corporations, the ability to simplify complex problems is a crucial skill. Daniel emphasizes the significance of breaking down overwhelming challenges into smaller, more manageable tasks, so that teams can navigate the complexities of technology and business transformation. His advice to "make the problems really small" serves as a valuable strategy for initiating progress and innovation within large organizations.The Importance of Working on Mission-Critical ProjectsEngaging with mission-critical projects can be a defining factor in one's career growth and development. Daniel reflects tackling projects that have the potential to make or break a company, which helped him resilience and leadership skills. His advice to focus on the most critical tasks resonates with the idea of continuous learning and self-improvement.Building and Leading High-Performance TeamsHigh-performance teams are a cornerstone of success in any organization. Daniel highlights the importance of aligning team members with a clear purpose to drive collaboration and goal achievement, and the type of leadership that will get them there. When you embrace the critical role of purpose-driven leadership and foster a shared understanding of objectives and strategies, you’re able to develop strong, innovative teams within any organization.The Role of Storytelling in Attracting Top TalentStorytelling plays a pivotal role in attracting top talent to organizations, especially in the technology sector. A powerful narrative that includes the journey of technological transformation and the challenges that were overcome, companies can more easily attract top talent who are seeking meaningful and impactful work. Daniel also underscores the importance of transparency in the narrative and the workplace culture it builds.Scaling Technology Innovations GloballyDaniel discusses the importance of starting small and learning fast when expanding technology solutions across global, diverse markets. Sweeping changes, especially with technology, require a strategic and iterative approach. Daniel’s approach begins with running ‘experiments’ in smaller regions, analyzing the data, and basing the wider implementation on those data-driven insights to ensure smoother transitions for companies and their customers.Resources:Daniel Henry on LinkedIn | X(Twitter)

Feb 28, 2024 • 42min
Leadership Transformation Mindset Advice with Sabrina Braham
What was your biggest personal transformation? More importantly, who helped you achieve it? Read this blog and episode of the Unlearn Podcast for top leadership transformation mindset advice from a world-class leadership coach.Sabrina Braham is an executive coach, mastermind group leader, author, and leadership and career development expert with almost three decades of experience, but she nearly walked away from that journey before it ever began. What kept her going? A teacher who was more like a coach. He encouraged and believed in her, which helped her completely transform what she thought about herself and her future. And now, Sabrina does that for others.There’s a reason that 97% of all CEOs in the United States have coaches for leadership transformation mindset advice. Asking for feedback is a powerful tool for personal growth and development. Embracing the discomfort of asking questions can lead to valuable insights, accelerated learning, and improved decision-making.Embracing Growth Mindset and Overcoming Self-DoubtWe all have moments that transform us. For Sabrina, it was when her psychology teacher refused to let her quit and had her enroll in the most difficult classes. "He totally believed in me," she reflects. This experience sparked a shift from self-doubt to a growth mindset, and the encouragement helped her see and embrace her full potential. Often, a big part of transformation is identifying the self-imposed limitations we have created, and Sabrina’s journey from uncertainty to academic excellence is an inspiring example of how a single act of faith from another can catalyze our growth and help us transcend our perceived barriers.The Power of Asking for FeedbackMany of us live in a precarious balancing act every day: personal turmoil, parenthood, entrepreneurship, partnership. Sometimes we need the voice of clarity to help us make sense of it all. But first, we need to ask that voice to speak. Asking for feedback is not a sign of weakness, but a brave step towards self-betterment, and it’s not about uncovering flaws alone. It’s all about acknowledging and harnessing our inherent strengths. When we embrace vulnerability, we can actively seek out the insights that will propel us forward.Building Relationships and Political SavvyWorkplace dynamics are an intricate dance, and it’s critical to nurture relationships and develop political acumen. Sabrina challenges the notion that career advancements are merely the result of nepotism, suggesting that the key lies in "deepening your relationships with people." The subtleties of professional success include both genuine connection and strategic navigation of organizational landscapes, which lead to recognition and advancement. In other words, how we interact with others will significantly influence our career trajectory. The Role of Mastermind Groups in Accelerating GrowthSabrina is passionate about leading executive mastermind groups, describing them as a collective committed to mutual growth, where "everybody in the group helping the person that's talking." These groups act as a powerful catalyst for personal and professional development, offering a space where shared experiences and diverse viewpoints can lead to unexpected insights and breakthroughs. A well-run mastermind group is the ideal community for leadership transformation mindset advice. They become your own personal “board of directors”. Mastermind groups harness collaborative intelligence, allowing each member to contribute to and benefit from the collective wisdom. It's a testament to the idea that by coming together, we can amplify our learning and accelerate our journey towards our goals.ResourcesFor full show notes, go to BarryO'Reilly.comSabrina Braham MA MFT PCC on the web | LinkedIn | Leadership Podcast
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