Podcast
The Silicon Valley Podcast
Hosted by Shawn Flynn · EN
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.
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22episodes
Episodes
Newest firstAll episodes
Ep 273 How AI is Changing Deals & Global Development with Jeff Kafka and Brian Rogers
Oct 2700:46:44Tap to summarizeHow 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.
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Ep 272 Startup Founder Pay, AI’s Impact, and Bootstrapping Trends with Pilot CEO Waseem Daher
Oct 700:37:47Tap to summarizeGuest: 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.
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