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. 2D AGO

    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

  2. SEP 22

    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

  3. SEP 17

    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

  4. SEP 8

    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

  5. SEP 2

    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

  6. AUG 20

    Ep 267 Scaling Seismic Ventures with Ross Fubini

    Bio: Ross is a founder, engineer, and early-stage technology investor who focuses on helping significant ideas scale up. He believes in working with "amazing people who build products indistinguishable from magic." His unique strength lies in connecting people. Episode Summary: In this episode, we sit down with Ross Fubini to discuss his journey from building companies to investing in them. Ross shares how he developed the thesis for XYZ, a fund that invests in founders tackling big problems across sectors like public policy, fintech, and climate. We'll explore what it means to make "seismic shifts in society" and what sets founders who "make doing the work their unfair advantage" apart from the rest. Key Discussion Points: From Builder to Investor: What inspired Ross to transition from engineering to venture capital. The XYZ Thesis: A deep dive into the fund's investment strategy and how it differs from other early-stage firms. The "2nd Derivative of Investments": Ross explains this unique investment concept and how he applies it to his decision-making. Public Sector Impact: How the public sector ecosystem influences private sector investment decisions. LP Reporting: Ross shares insights on how to structure effective quarterly reports and what Limited Partners truly value. The Deal Review Process: A look at the critical factors Ross evaluates when deciding to invest in a founder. Founder Mindset: The non-negotiable behaviors and traits Ross looks for in an early-stage founder. Investing in Volatility: A discussion on how funds can pivot and refine their strategies in a challenging macro environment. Learn More About Ross and XYZ: Ross Fubini's LinkedIn: https://www.linkedin.com/in/fubini/ XYZ Venture Capital Website: http://www.xyz.vc 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.

    32 min

  7. AUG 10

    Ep 266 Building AI at the Edge of Innovation with Ben Van Roo

    Episode Summary: In this episode, we sit down with Ben Van Roo, CEO and Co-Founder of Legion Intelligence and a seasoned leader whose career spans building cutting-edge AI solutions for both the public and private sectors. From working with the Department of Defense at RAND to leading data science at Chegg, serving as EVP of National Security at Primer AI, and now driving innovation at Yurts, Ben brings a rare perspective on AI, leadership, and scaling technology for mission-critical environments. We dive into his journey of building strong company cultures, navigating brand transformations, and understanding the differences between public and private sector AI adoption. Ben also shares valuable lessons on choosing the right investors, balancing family life with startup leadership, and why timing can be as important as talent in the entrepreneurial journey. If you’re a founder, operator, or AI enthusiast—especially one interested in government tech, venture capital relationships, or building trust in enterprise AI—this is an episode you won’t want to miss. Key Topics Discussed: How public and private sector experiences shaped Ben’s leadership style. Lessons learned from winding down a company as CEO. Balancing startup life with family responsibilities. Building team culture and alignment at Legions. Insights from rebranding and redefining a company’s identity. Navigating the complexities of working with the Department of Defense. Differences in AI adoption between public and private sectors. Finding and working with “nice” VCs and spotting red/green flags early. Advice for veterans and government professionals starting companies. The advantages of being a founder later in life. How timing and opportunity intersect in entrepreneurial success. What’s next for Yurts over the next 12–18 months. Resources & Links: Ben Van Roo on LinkedIn: https://www.linkedin.com/in/vanroo/ Legion Interl: LEGION | Secure AI for Mission-Critical Teams 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 do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.”

    44 min

  8. AUG 3

    Ep 265 A Global Perspective of Venture Capital: with George Panagiotakopoulo

    Guest: George Panagiotakopoulos, Innovation Ecosystem Development -Advisor, Berkeley SkyDeck Episode Summary: Join us as we sit down with George Panagiotakopoulos, who works with UC Berkeley who has a unique vantage point from his work in Europe, Asia, and beyond, George shares his insights on building global innovation ecosystems and the nuances of cross-border collaboration. We'll explore how Berkeley is expanding its accelerator model internationally, the differences in venture capital ecosystems and risk tolerances worldwide, and the common misconceptions that investors and founders face when navigating new markets. This episode is a must-listen for anyone interested in the future of startups, venture capital, and global innovation. Key Discussion Points: Berkeley SkyDeck's Global Mission: George explains his primary mandate and the challenges of building innovation ecosystems beyond Silicon Valley. The Global VC Landscape: A deep dive into how the venture capital ecosystem in Europe and Asia differs from that of Silicon Valley, including core belief systems and risk tolerances. Tailoring Accelerator Programs: We discuss how Berkeley customizes its programs to meet the unique needs of different regions. Investor and Founder Misconceptions: George sheds light on common misunderstandings that international investors and founders have when evaluating startups or entering the U.S. market. Cross-Border Synergy: A success story about a time when expanding SkyDeck's presence led to unexpected synergies and outcomes. Looking Ahead to Africa: George shares his thoughts on the opportunities and roadblocks for replicating the model in South East Asia and other parts of the world. Advice for International Founders: Practical advice on when and how international startups should approach U.S. investors and enter the U.S. market. Learn More: Connect with George Panagiotakopoulos on LinkedIn. George Panagiotakopoulos | LinkedIn Visit the Berkeley SkyDeck website to learn more about their programs. http://skydeck.berkeley.edu/ 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 the people of this show and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

    50 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

Information

  • Creator
    Shawn Flynn
  • Years Active
    2020 - 2025
  • Episodes
    273
  • Rating
    Clean
  • Copyright
    © Copyright 2021 All rights reserved.
  • Show Website
    The Silicon Valley Podcast

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