The Silicon Valley Podcast

Shawn Flynn
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We open a window into the minds of the most successful leaders, investors, creators, and inventors — sharing Silicon Valley business acumen with entrepreneurs around the world. Silicon Valley ”Podcast Must Follow” - Feedspot

  1. 1 DAY AGO

    Ep 275 Measuring & Managing Value with Tim Koller, Co-Author of McKinsey’s Valuation

    Guest: Tim Koller, Partner at McKinsey & Company and Co-Author of Valuation: Measuring and Managing the Value of Companies For over three decades, Valuation has been the definitive guide to corporate value creation. Called “the best practitioners’ guide to valuation” by the Financial Times and one of “the most influential contemporary books about the world economy” by The Economist, the book has sold over one million copies worldwide. Now in its 8th edition, Tim Koller and his co-authors bring fresh insights on AI, sustainability, digital transformation, and geopolitics—helping business leaders sharpen their decision-making and balance long-term value creation with the pressures of today’s markets. In this episode, Tim shares: Why short-term earnings obsession remains the biggest misconception in corporate strategy How AI can help identify groupthink and bias in real time The real impact of tariffs and geopolitics on company valuations How leaders can balance shareholder value with stakeholder needs Why sustainability priorities should be tailored to the unique risks of each industry Lessons from Warren Buffett and contrarian thinkers who resisted market hype What has—and hasn’t—changed about being a great CEO since 1990 Tim also reflects on 35 years of writing Valuation, explaining why timeless principles of growth, innovation, and long-term orientation matter more than ever in both stable and volatile times. About the Guest Tim Koller is a partner at McKinsey’s Denver office and founder of McKinsey’s Strategy and Corporate Finance Insights team. With more than 40 years of consulting experience, he has helped countless executives, boards, and investors navigate complex financial and strategic decisions. Resources & Links 📖 Valuation: Measuring and Managing the Value of Companies (8th Edition) – Available May 20, 2025 from Wiley 🔗 Connect with Tim Koller via his PR contact: Rebecca Proulx, rebecca@fortierpr.com Disclaimer: The views expressed in this podcast are for informational purposes only and do not constitute financial or legal advice. They do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    45 min

  2. 2 NOV

    Ep 274 What Makes Entrepreneurs Unstoppable? With Lori Rosenkopf

    Guest: Lori Rosenkopf – Vice Dean of Entrepreneurship, Wharton School Bio Lori Rosenkopf is the Vice Dean of Entrepreneurship and the Simon and Midge Palley Professor at the Wharton School of the University of Pennsylvania. As Wharton’s Faculty Director for Venture Lab, she supports student entrepreneurs across the university. She previously served as Vice Dean and Director of Wharton’s 2,500-student Undergraduate Division from 2013 to 2019, where she introduced a new curriculum, expanded career pathways, and created more opportunities for students. Her research and teaching draw from her background in systems engineering and social science, with a focus on networks and learning in knowledge industries. With deep connections to Wharton alumni and a sharp understanding of millennial and Gen Z aspirations, Lori brings a unique perspective on the future of entrepreneurship. What You’ll Learn in This Episode The most transformative changes in entrepreneurship education at Wharton What makes Wharton’s approach effective in producing world-class leaders How students are expanding their definition of entrepreneurship beyond Silicon Valley stereotypes The role of mentors and role models in shaping entrepreneurial careers Traits Lori has seen consistently in students who go on to build impactful ventures Insights from her book Unstoppable Entrepreneurs and the stories that inspired it How Wharton alumni networks create opportunities for the next generation of founders Lessons from organizations like Harlem Capital on the future of venture funding How Gen Z founders are rethinking impact, purpose, and business models Disclaimer The views expressed in this podcast are Lori’s own and are for informational purposes only. They do not constitute financial or legal advice, nor do they necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    47 min

  3. 27 OCT

    Ep 273 How AI is Changing Deals & Global Development with Jeff Kafka and Brian Rogers

    How AI is Changing Deals & Global Development with Jeff Kafka and Brian Rogers     Jeff Kafka Bay Area entrepreneur, cybersecurity startup founder, and medical device/supply chain import partner. Internationally renowned professional kiteboarder and big wave safety expert. Brian Rogers Design and business thinker, expert in AI/ML, IoT, big data, fintech, and platform development. Author of patents, guest lecturer, and industry leader in blockchain. Episode Summary In this episode, we dive deep into how technology, infrastructure, and strong personal networks converge to drive capital and growth in sectors from medical devices to public works. We speak with Jeff Kafka, the founder behind the famous Silicon Valley kite surfing pitch events, about the value of relationships in business growth, and with Brian Rogers, an expert in AI, IoT, and digital transformation, about the future of finance and government partnerships. We explore how their new venture, Storyboard Capital, focuses on opportunities in areas typically ignored by traditional tech investors. Key Discussion Points & Topics I. The Power of Relationships and Networking (Jeff Kafka) Kite Surfing Pitch Events: The origin story of the famous Silicon Valley kite surfing pitch events and the key lessons learned while observing early-stage companies raising capital. Missed Opportunities: Jeff shares his list of companies he met early on but passed on investing in, and the reasons why those opportunities were missed at the time. The Role of People: How Jeff's diverse career—from cybersecurity to big wave safety to medical supply chain—has consistently revolved around people and relationships. Business Growth: The crucial importance of relationships when scaling a business. II. Technology, Government, and Global Development (Brian Rogers & Jeff Kafka) Public/Private Partnerships (P3s): A detailed explanation of what Public/Private Partnerships are and how companies currently go about identifying these government opportunities. AI in Government Financing: How Artificial Intelligence can help streamline the process for companies to find and obtain government contracts. Technology for Development: How technology, public/private partnerships, and infrastructure development are creating opportunities in remote or "off the grid" areas globally. III. The Future of Finance and Investment Banking AI and Financing: How Jeff and Brian see AI changing the landscape for companies obtaining financing, particularly in how deals are sourced and structured. Investment Banker's Role: The evolving role of the investment banker in the future and how they will integrate AI into transaction processes. The Future of Outreach: How customized, AI-driven outreach will change the success or failure rates for projects and deal sourcing. Beyond the Interview: Key concepts related to AI that the audience should be thinking about moving forward. Learn More Storyboard Capital Website: https://storyboardcapital.com/ Jeff Kafka's Contact: Jeffkafka8@gmail.com Jeff Kafka's LinkedIn: https://www.linkedin.com/in/jeffkafka/ Brian Rogers' LinkedIn: https://www.linkedin.com/in/brogers/ Affiliate Companies: https://grapheene.com http://www.strongwatertech.com Disclaimer The views expressed on this podcast are for informational purposes only and not financial or legal advice. Consult with a professional for your specific situation and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    47 min

  4. 7 OCT

    Ep 272 Startup Founder Pay, AI’s Impact, and Bootstrapping Trends with Pilot CEO Waseem Daher

    Guest: Waseem Daher – Founder & Executive Chairman of Pilot LinkedIn: Waseem Daher Pilot: pilot.com | Founder Salary Report 2025   Bio Waseem Daher is the Founder and Executive Chairman of Pilot, a modern finance team offering bookkeeping, tax, and CFO services for startups, e-commerce businesses, and professional services firms. Backed by Sequoia Capital and Bezos Expeditions, Pilot has become the go-to back office solution for growing companies. An engineer by training and a serial entrepreneur, Waseem previously co-founded Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox). He now combines his experience as a three-time founder with insights into startup finance, scaling, and leadership. Beyond Pilot, Waseem writes regularly about building startups on LinkedIn and in his newsletter, Startup Real Talk. What You’ll Learn in This Episode Why founder salaries dropped 43% in 2025 and what this means for early-stage companies How founders should think about compensation when talking to investors Risks startups face when founders underpay themselves How company stage, funding, and geography influence salary decisions The role of boards and investors in shaping compensation What lessons Waseem carried from Ksplice and Zulip into Pilot Insights into bootstrapping vs. venture-backed founder pay How founders can use Pilot’s salary data to benchmark and negotiate effectively Why the number of AI startups surged by 287%, yet founder salaries declined What the rise in bootstrapped startups (up 77%) says about today’s funding environment Disclaimer: The views expressed in this podcast are my own and are for informational purposes only. They do not constitute financial or legal advice, nor do they necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    38 min

  5. 22 SEPT

    Ep 271 Reimagining Work and Storytelling in the Age of AI with Shawn Villaron

    Guest: Shawn Villaron, Vice President of Customer and Strategic Initiatives, Office Product Group at Microsoft | Former VP & GM of PowerPoint | Bay Area Site Leader | Executive Sponsor of HOLA   Episode Overview In this episode, we sit down with Shawn Villaron, a 29-year veteran at Microsoft who has helped shape some of the company’s most widely used products and strategies. Now serving as Vice President of Customer and Strategic Initiatives in the Office Product Group, Shawn partners with Microsoft’s most important customers to better understand their needs around AI, workplace modernization, and productivity—insights that directly shape the future of Microsoft Office. Previously, Shawn was Vice President & General Manager for PowerPoint, where he led teams across multiple platforms—Windows, Mac, Web, iPad, Android, and iOS—reimagining how billions of people create and deliver stories. He also serves as Engineering Site Leader for Microsoft Bay Area, working across commercial, consumer, hardware, and AI platforms, while championing diversity and inclusion as executive sponsor of HOLA (Hispanic & Latinx Organization of Leaders in Action). Shawn brings a rare perspective: spending nearly three decades at a single company, driving innovation from the inside, and now exploring how AI and agents are reshaping the way we work, create, and build businesses. What You’ll Learn in This Episode The positives and challenges of building an entire career at one company in the fast-moving tech world. How PowerPoint and Office are being reimagined for the AI storytelling era. Practical ways companies can encourage employees to use AI responsibly and effectively. How leaders can use AI to boost both creativity and productivity within teams. When employees might be using too much AI—or not enough. What it means to become an “AI Agent Boss” and how agents can give startups enterprise-level capabilities. Whether the concept of the one-person unicorn is realistic, and what’s still missing. How recent graduates can stand out in an AI-driven job market. The emerging technologies Microsoft’s Bay Area teams are most excited about right now. One piece of advice Shawn would give to founders and technologists building the next generation of workplace tools. Key Questions We Discuss What are the upsides and downsides of staying at one company for nearly three decades? How is Microsoft rethinking storytelling with AI in PowerPoint and Office? How can leaders balance productivity and creativity when adopting AI tools? What role will AI Agents play in empowering both startups and enterprises? Are we truly heading toward the era of the one-person unicorn? What advice would you give to graduates entering an AI-powered job market? Which emerging technologies are your Bay Area teams most focused on right now? About Shawn Villaron Shawn Villaron is Vice President of Customer and Strategic Initiatives in the Microsoft Office Product Group, where he drives strategy by working closely with top customers to shape the future of AI and productivity. Previously, he served as Vice President & GM of PowerPoint, guiding the product across every platform and ensuring seamless experiences for millions of users. He also serves as Engineering Site Leader for Microsoft Bay Area and as executive sponsor of HOLA, advancing diversity and inclusion at Microsoft. Resources & Links LinkedIn: Shawn Villaron | LinkedIn Microsoft Bay Area Blog: Microsoft Bay Area Blog Microsoft Work Trend Index: The 2025 Annual Work Trend Index: The Frontier Firm is Born   The views expressed on this podcast are for informational purposes only and do not constitute financial or legal advice. Please consult with a professional for guidance on your specific situation. The opinions shared are my own and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    42 min

  6. 17 SEPT

    Ep 270 Redefining Networking and Security in the Age of AI with Pankaj Patel

    Podcast Show Notes: Pankaj Patel – Redefining Networking and Security in the Age of AI Guest: Pankaj Patel, Founder and CEO of Nile | Former EVP and Chief Development Officer at Cisco | Partner at JC2 Ventures | Senior Advisor at March Capital Episode Overview In this episode, we sit down with Pankaj Patel, one of the most influential leaders in enterprise technology. As the former engineering head of Cisco’s $38 billion portfolio with a $6 billion R&D budget, and now the founder and CEO of Nile, Pankaj brings unparalleled insight into the future of networking, AI, and enterprise security. Pankaj shares lessons from building and leading global engineering organizations, the principles he applied to acquisitions and innovation at scale, and why he believes simplicity and security must define the next era of enterprise technology. We also explore how Nile is disrupting the status quo, delivering secure and simple networking as a service, and why Pankaj considers this company the fulfillment of an “unfulfilled mission” in his career. Whether you’re a technology executive, founder, or investor, this conversation offers invaluable perspective on how to navigate complexity, embrace AI, and prepare for the enterprise networks of the future. What You’ll Learn in This Episode Leadership at scale: What it was like managing 29,000 engineers and a $6 billion R&D budget at Cisco. Acquisition strategy: How Pankaj evaluated companies for acquisition and integration. The AI reality check: Why many legacy companies are calling themselves AI-first, and whether the claims hold up. Simplicity in enterprise tech: Why products have historically been built around complexity, and why simplifying networks is both challenging and essential. Security reimagined: What truly makes a system secure, why humans are often the weakest link, and how AI will transform security. The “unfulfilled mission”: Why Pankaj launched Nile and how the company is disrupting the networking industry. Future of enterprise tech: How networking, AI, and security are converging to reshape the next decade. Investor perspective: What Pankaj looks for in founders and startups as a board member, advisor, and venture partner. Key Questions We Discuss What principles guided your allocation of Cisco’s $6 billion R&D budget? What criteria did you use when acquiring companies, and how did you evaluate integration risk? Why has enterprise tech often thrived on complexity, and how is Nile changing that? How do you see AI shaping the future of networking and security? What advice would you give to enterprises overwhelmed by legacy systems? What was the “unfulfilled mission” that led you to launch Nile? How has your leadership style evolved from managing tens of thousands at Cisco to leading a focused startup team? What do you look for in founders when joining boards or investing? How will the convergence of networking, AI, and security define the next 5–10 years? About Pankaj Patel Pankaj Patel is the Founder and CEO of Nile, where he is reimagining the future of networking by delivering secure, simple, and customer-obsessed services. Previously, he served as Executive Vice President and Chief Development Officer at Cisco, overseeing the company’s $38 billion product portfolio. He is also a Partner and Chief Strategy Officer at JC2 Ventures, a Senior Advisor at March Capital, and serves on the boards of several leading technology startups. Connect with Pankaj Patel LinkedIn: Pankaj Patel Nile: https://nilesecure.com Disclaimer The views expressed in this podcast are for informational purposes only and do not constitute financial, legal, or investment advice. Please consult with a qualified professional regarding your specific situation. The views expressed are those of the guest and host and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC. #ai #cybersecurity #nilesecure #siliconvalley #podcast

    41 min

  7. 8 SEPT

    Ep 269 How to Break into Venture Capital with Taylor Brandt

    Join us for an insightful conversation with Taylor Brandt, a Partner at Headline, where we dive into the world of venture capital and B2B software. Taylor specializes in vertical SaaS, B2B marketplaces, and commerce infrastructure as a Partner in Headline’s In this episode, we explore Taylor's unique perspective, shaped by her background in marketing and analytics engineering: We cover key topics for founders and aspiring VCs, including: Fundraising Misconceptions: What is a common mistake founders make when pitching to VCs, especially regarding their focus on senior partners? Founder Traits: What underrated qualities does Taylor look for in strong founders of B2B companies? Breaking into VC: Taylor shares her advice for those without a “traditional” resume and reveals her own path into the industry. Assessing Risk: How does she evaluate the adoption risk of investing in infrastructure and logistics companies? The Future of Tech: We get Taylor's take on the next big opportunities in vertical SaaS and B2B marketplaces, and what signals she's tracking. AI Adoption: A discussion on how AI is being adopted in businesses, particularly when it doesn't require a change in existing processes. Athlete & Founder Mindset: Exploring the correlation Taylor sees between being an athlete and a successful founder or VC. Disclaimer: The views expressed on this podcast are for informational purposes only and not financial or legal advice. Consult with a professional for your specific situation. The views expressed are my own and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC. Connect with Taylor Brandt: LinkedIn: https://www.linkedin.com/in/taylor-brandt-89415250/ Headline Website: https://headline.com/ #VentureCapital #FounderAdvice #TechInvesting #SaaSTech #StartupFunding #VC

    41 min

  8. 2 SEPT

    Ep 268 The Mindset of a Top-Tier VC with Mercedes Bent

    Mercedes Bent, formerly a Partner at Lightspeed, and a leading investor in fintech, AI, and consumer companies. Guest Bio: Mercedes Bent is a seasoned investor with a background that spans venture capital, startups, and institutional finance. As a former Partner at Lightspeed, she spent over five years leading investments in companies like Stori, Mexico's first tech unicorn co-founded by a woman. Before her time in VC, she served as a General Manager, scaling a startup from $2M to $100M in revenue, and worked at Goldman Sachs managing $1.75B in assets. Mercedes holds degrees from Harvard and Stanford. Episode Summary: Join us for a deep dive with Mercedes Bent, a top investor with a unique perspective on technology, finance, and building a successful career. We'll discuss her journey from managing institutional assets at Goldman to becoming a partner at a major venture fund. Mercedes will share her insights on how to identify market trends, evaluate founders, and the critical role of timing in a fund’s performance. Key Discussion Points: The Hierarchy of Metrics: We explore Mercedes's framework for evaluating a company's health and why founders should pay close attention to it. Building a Fund: What it's like, both logistically and emotionally, for a partner to launch their own fund while managing an existing portfolio. Risk and Timing: The parallels between high-stakes games like poker and the world of venture capital. How to think about risk, probability, and when to go "all in." Evaluating the Market: Mercedes's mental models for assessing new trends, founders, and the future of consumer technology and AI. The VC Crossover: Advice for aspiring investors and operators looking to break into the venture capital space. The Rise of the RIA: A look into why some larger venture funds are shifting their business models and how that could reshape the industry. Connect with the Guest: Mercedes Bent's LinkedIn: https://www.linkedin.com/in/mercedesbent/ Disclaimer: The views expressed are for informational purposes only and not financial or legal advice. Opinions are my own and do not reflect those of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC. Consult a professional for your specific situation.

    43 min
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We open a window into the minds of the most successful leaders, investors, creators, and inventors — sharing Silicon Valley business acumen with entrepreneurs around the world. Silicon Valley ”Podcast Must Follow” - Feedspot

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  • Creator
    Shawn Flynn
  • Years Active
    2020 - 2025
  • Episodes
    276
  • Rating
    Clean
  • Copyright
    © Copyright 2021 All rights reserved.
  • Show Website
    The Silicon Valley Podcast

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