In this episode, Vaibhav Nadgauda, Chief Executive Officer (CEO) of App Orchid, Inc., shares an operator to venture capital journey, how they built a founder friendly investing approach, and what changed when they stepped in as CEO after a founder’s passing. You will learn how VC fundraising works at the fund level, how to think about pivots and team quality, and why the enterprise AI wave is forcing a rethink of the data stack.

Episode Description What does founder friendly venture capital actually look like in practice, especially when the investor has lived the operator journey?

In this conversation, we break down the shift from building and exiting companies to raising a first fund, evolving the LP base over time, and learning the mental model change from operator problem solving to investor portfolio focus.

We also go deep on enterprise AI and data strategy, including why semantic layers, ontologies, and knowledge graphs are becoming critical for interacting with siloed enterprise data. If you are navigating venture capital fundraising, B2B software, product market fit, or go to market focus, this episode offers concrete lessons that translate.

We cover • Why teams beat the original pitch, and why pivots are normal • How LP trust is built, and what changes from fund one to fund three • The investor mindset shift, backing winners and allocating attention • Conviction vs delusion, and how to process customer feedback • Enterprise AI readiness, semantic layers, ontologies, and knowledge graphs • Seeing around the corner, why experience changes pattern recognition

Who this is for Founders, operators, and investors who want a sharper framework for VC fundraising, B2B investing, and the enterprise AI data shift.

Links and Resources Spotify: https://bit.ly/spotify-itsm Apple Podcasts: https://bit.ly/apple-itsm Amazon Music: https://bit.ly/amazon-itsm Website: https://insidethesiliconmind.com/ Follow on LinkedIn: https://www.linkedin.com/company/inside-the-silicon-mind/ Instagram: https://www.instagram.com/insidethesiliconmind/ TikTok: https://www.tiktok.com/@insidethesiliconmind X: https://x.com/InSiliconMind

Mentioned in This Episode • Until the End of Time, Brian Greene • Our Mathematical Universe, Max Tegmark • Only the Paranoid Survive • The Innovator’s Dilemma • ChatGPT • Knowledge graphs • Ontologies and semantic layers • Salesforce • SAP • Snowflake

About the Show Inside the Silicon Mind is your masterclass in high stakes innovation, business strategy, and the Silicon Valley mindset. Hosted by Firas Sozan, we interview Founders, CEOs, and Venture Capitalists shaping the future of technology.

Hassan Khajeh-Hosseini, the founder of Infracost, joins Firas Sozan to break down shift left FinOps, cloud cost prevention, and how engineers can understand cloud spend before code reaches production.

Episode Description Cloud cost optimization is still a mess, not because teams do not care, but because most tools start from the bill. By the time you see spend in a dashboard, the code is already in production and the waste is already happening.

In this episode, Hassan Khajeh-Hosseini, the founder of Infracost, explains shift left FinOps, a practical approach that runs cost simulations inside engineering workflows so teams can predict cloud costs before shipping. You will hear why cloud pricing exploded into millions of price points across AWS, Azure, and Google Cloud, how enterprise cloud spend can reach hundreds of millions per year, and where cost waste hides in day to day infrastructure decisions.

We also cover the founder side, fundraising signals, why inbound distribution matters, how a failed startup taught a hard lesson about hiring rare talent, and why product market fit is a moving target that can feel scary when it hits.

We cover • Why traditional FinOps starts too late, after spend is incurred • How to simulate cloud costs from infrastructure as code before deploys • The $550,000 per month change that got stopped in review • ICP personas, engineers, platform teams, FinOps, and engineering leadership • Distribution pull vs push, and why it changes GTM economics • Fundraising, story, network, and early usage metrics that matter

Who this is for: Founders, operators, and tech leaders who want practical ways to prevent cloud waste and build stronger FinOps and platform engineering practices.

Links and Resources Spotify: https://bit.ly/spotify-itsm Apple Podcasts: https://bit.ly/apple-itsm Amazon Music: https://bit.ly/amazon-itsm Website: https://insidethesiliconmind.com/ Follow on LinkedIn: https://www.linkedin.com/company/inside-the-silicon-mind/ Instagram: https://www.instagram.com/insidethesiliconmind/ TikTok: https://www.tiktok.com/@insidethesiliconmind X: https://x.com/InSiliconMind

Book Recommendations from this episode: • Steve Jobs, by Walter Isaacson • The Count of Monte Cristo, by Alexandre Dumas • Acquired podcast • Heavyweight podcast • Secrets of Sand Hill Road, by Scott Kupor

About the Show Inside the Silicon Mind is your masterclass in high-stakes innovation, business strategy, and the Silicon Valley mindset. Hosted by Firas Sozan, we interview Founders, CEOs, and Venture Capitalists shaping the future of technology.

Jonathan Claybaugh, Former Principal Infrastructure Engineer at Snowflake, shares how to evaluate a startup before joining, including equity math, market size, and the mindset required to stay through the grind.

Episode Description: What does it actually take to join the right startup early, and build enough upside to work by choice, not necessity?

In this episode, Jonathan walks through his journey as an early employee at Snowflake, joining as the 13th hire before any customers existed. He explains the signals that made the opportunity feel real, including repeatable revenue growth, retention, and a team culture built on responsibility, humility, and customer obsession.

You will also get a practical framework for evaluating startup risk, how to think about TAM, why doing the equity dilution math matters, and why derivative ideas usually lose. If you are a founder, operator, or engineer deciding between Big Tech comfort and startup adventure, this conversation gives you a clear lens to make the call.

We cover: • How to evaluate a startup using market size, originality, and culture • What to look for in leadership transitions as a company scales • Why retention and customer feedback loops drive compounding growth • How early employees should think about equity, dilution, and taxes • The difference between wanting startup life and enduring it

Who this is for: Founders, operators, and engineers who want a real framework for choosing an early stage startup with conviction.

Links and Resources: Spotify: https://bit.ly/spotify-itsm Apple Podcasts: https://bit.ly/apple-itsm Amazon Music: https://bit.ly/amazon-itsm Website: https://insidethesiliconmind.com/ Follow on LinkedIn: https://www.linkedin.com/company/inside-the-silicon-mind/ Instagram: https://www.instagram.com/insidethesiliconmind/ TikTok: https://www.tiktok.com/@insidethesiliconmind X: https://x.com/InSiliconMind

Mentioned in This Episode: • Extreme Ownership, Jocko Willink

About the Show: Inside the Silicon Mind is your masterclass in high-stakes innovation, business strategy, and the Silicon Valley mindset. Hosted by Firas Sozan, we interview Founders, CEOs, and Venture Capitalists shaping the future of technology.