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In this episode of Startup Spotlight, hosts Shirish Nadkarni and Gowri Shankar speak with Anuj Gosalia, former Head of Inference at OpenAI and a veteran engineering leader at Microsoft, Meta, and Google. Drawing on his experience at the forefront of GPUs, virtual reality, and AI, Anuj explores how large language models are reshaping entrepreneurship—and why solving real customer problems remains the foundation of a successful startup.

Key topics covered include:

• Frontier vs. open-weight models: How the capability gap is narrowing and why benchmark scores don’t always reflect real-world performance.
• Choosing the right AI model: Why Anuj recommends using the best available models for coding, then selecting models for your product through evaluations tailored to customer needs.
• Product-market fit before cost optimization: Why founders should first build something customers value, then optimize inference costs as usage grows.
• Distillation and enterprise knowledge: How learning from AI interactions can help companies build institutional knowledge and improve their systems.
• Chinese models and customer trust: The distinct considerations around model origins, inference providers, hosting locations, and data governance.
• AI regulation and societal impact: Anuj’s perspective on accountability, geopolitical competition, inequality, and the challenges of rapid technological change.
• Coding tools, agents, and engineering culture: How integrated AI tools and customer usage create competitive advantages, and why faster coding and agent swarms still leave complex engineering problems to solve.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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Serial entrepreneur Nikesh (Niki) Parekh joins us to share lessons from building Suplari, an AI-powered procurement intelligence company acquired by Microsoft in 2021, and his newest venture, Provn.

Niki takes us behind the scenes of Suplari—from validating the idea with customers and finding product-market fit to scaling enterprise sales, navigating setbacks, and ultimately selling the company to Microsoft. He also shares what he would do differently and offers practical lessons for founders building enterprise software.

We then explore Provn, which Niki describes as the “NFL Draft for AI talent.” Instead of relying on resumes, prestigious universities, or previous employers, Provn asks candidates to demonstrate what they can actually build with AI. The goal: help exceptional talent anywhere in the world prove their abilities and get discovered by great employers.

In this episode, we discuss:
* How Suplari validated its idea and found product-market fit
* Lessons from scaling—and having to reboot—an enterprise sales organization
* How Suplari went from trying to partner with Microsoft to being acquired by it
* Why founders should build relationships with potential strategic acquirers early
* Why AI could make the traditional resume increasingly obsolete
* How Provn evaluates candidates through real-world AI challenges
* Why great talent can come from anywhere—not just elite universities and companies
* Niki’s advice on fundraising, purpose, and building a company you truly care about

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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What does it take for a team of high school students to build an AI startup that wins the TYE Global Competition?

In this episode of Startup Spotlight, we sit down with the founders of DuggAI, the team behind this year's TYE (TiE Young Entrepreneur Global competition. The team shares the fascinating journey of transforming a series of startup ideas into Dugg OS—an AI operating system that helps companies orchestrate and manage multiple AI agents and workflows.

The conversation goes far beyond the technology. The team discusses how they learned to iterate quickly, abandon ideas that weren't working, validate products with real customers, and think like experienced founders. They also share the lessons they learned from TYE mentors, their ambitions for Y Combinator, and how they're balancing startup dreams with college plans.

Can high school students tackle two of the world's biggest environmental challenges with a single business idea?

In this episode of Startup Spotlight, we speak with Team HydroBin, the third-place winners of the TYE Global Competition, about their innovative startup that transforms ocean-bound plastic into durable, reusable shipping containers. The team shares how they identified a massive opportunity at the intersection of sustainability and logistics, developed a working prototype, secured manufacturing partners, and began conversations with major retailers and logistics companies.

The discussion explores how they validated customer demand, built a compelling business model, and leveraged mentorship through the TYE program to turn an idea into a real company. It's an inspiring look at what young entrepreneurs can accomplish when they combine passion, persistence, and customer-driven innovation.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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In this episode of From Startup to Exit, we sit down with Ezhilarasan (Ez) Natarajan, CEO and co-founder of CoreStack, to explore the company's remarkable journey from startup to global leader in multi-cloud and AI governance. Ez shares how his years building Microsoft Azure inspired him to tackle one of the biggest challenges facing enterprises: simplifying cloud adoption. He discusses how the team validated an idea that investors initially dismissed, built an enterprise platform from the ground up, secured early design partners, and scaled CoreStack into a company serving thousands of customers worldwide. The conversation then turns to the AI revolution, where Ez offers a compelling vision for the future of AI governance, enterprise adoption, and the transformative impact AI will have across every industry over the coming decade.

In this episode, you'll hear about:
- How Ez Natarajan founded CoreStack after recognizing the growing complexity of multi-cloud adoption and why the market initially failed to see the opportunity.
- The startup journey—from self-funding and building the first product with design partners to securing product-market fit and raising venture capital.
- The lessons learned in building an enterprise software company by listening to customers instead of following conventional investor wisdom.
- How CoreStack evolved into a leading platform for cloud governance, helping enterprises reduce costs, improve operations, and strengthen security.
- Why today's AI revolution is fundamentally different from previous technology waves and what it means for businesses over the next decade.
- The emerging importance of AI governance—including managing AI costs, securing enterprise data, governing AI models, and controlling AI agents.
- Leadership insights on building culture, attracting exceptional talent, integrating acquisitions, and scaling a mission-driven technology company.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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 What does it really take to build multiple successful startups—and recover from failure along the way?

In this episode of Startup Spotlight, hosts Shirish Nadkarni and Gowri Shankar sit down with Sonu Aggarwal, serial entrepreneur, former Microsoft executive, founder of Flash Communications, Cordon, and UnifiedSquare, and current President of TiE Seattle.

Sonu shares an honest and insightful account of his entrepreneurial journey—from building one of the world's first enterprise instant messaging platforms and selling it to Microsoft, to experiencing the hard lessons of startup failure, and ultimately building UnifiedSquare into a global leader acquired by Unisys. Along the way, he offers practical advice on fundraising, product-market timing, enterprise sales, founder transitions, and the importance of perseverance.

The conversation also explores Sonu's vision for strengthening Seattle's startup ecosystem through TiE Seattle and why he believes the region is poised to become one of the world's premier entrepreneurial hubs.

Whether you're a first-time founder, an experienced entrepreneur, investor, or simply fascinated by startup stories, this episode is packed with hard-earned wisdom from someone who has lived every stage of the entrepreneurial journey.

In this episode, you'll hear:

• How an MIT brainstorming session led to the creation of one of the first enterprise instant messaging platforms.
• The remarkable cold call that resulted in Microsoft acquiring Flash Communications.
• Why Sonu's second startup failed—and the invaluable lessons it taught him about enterprise sales, revenue, and founding teams.
• How recognizing an unmet customer need inspired the creation of UnifiedSquare.
• The realities of leading a high-growth startup through years of ups and downs before achieving a successful exit.
• The difficult experience of stepping down as CEO—and why founders should view leadership transitions through the lens of what's best for the company.
• How UnifiedSquare's acquisition by Unisys unfolded through a structured M&A process.
• His vision for making Seattle one of the world's leading startup ecosystems through TiE Seattle.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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In this special tribute episode of From Startup to Exit, hosts Shirish Nadkarni and Gowri Shankar reflect on the life, legacy, and enduring impact of their dear friend, S. Somasegar—known to so many simply as “Soma.” A pioneering Microsoft executive, respected venture capitalist at Madrona, mentor, investor, and community builder, Soma touched countless lives across the technology and startup ecosystems.

Joining the conversation are two people who knew him exceptionally well: Tim Porter, Managing Director at Madrona, and Vetri Vellore, serial entrepreneur and founder whose career was shaped by Soma’s guidance over decades. Through personal stories and heartfelt reflections, they paint a portrait of a leader whose greatest gift was not his accomplishments, but his humanity. 

Listeners will hear how Soma’s quiet wisdom, humility, and generosity influenced entrepreneurs, colleagues, founders, and investors alike. Whether mentoring a young engineer, advising a startup founder, or helping shape one of the Pacific Northwest’s most successful venture firms, he approached every interaction with empathy, curiosity, and an unwavering desire to help others succeed. 

Tim Porter shares insights into Soma’s transition from Microsoft to Madrona, his remarkable ability to listen, lead, and bring people together, and the profound role he played in building companies and supporting founders. Vetri Vellore recounts a mentorship that began with a Microsoft interview and evolved into a decades-long friendship that influenced some of the most important decisions of his entrepreneurial journey.   

Above all, this episode is a celebration of a life lived in service to others. Soma’s legacy extends far beyond the companies he helped build or the investments he made. It lives on in the people he encouraged, the founders he believed in, the communities he strengthened, and the example he set through kindness, humility, and generosity. 

Though his passing leaves an immeasurable void, the stories shared in this episode remind us of a simple question that many who knew him now ask themselves: “What would Soma do?” It is a fitting tribute to a man whose influence will continue to be felt for generations to come.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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What does it take to build infrastructure for a world that didn't fully exist yet? In this episode, Kumar Senthil, CEO and Co-Founder of Firmly, shares how he spent five years quietly building the plumbing that lets AI agents discover products and complete purchases on behalf of consumers, all while keeping the merchant in control of their data and customer relationship.
Kumar recounts the long, often painful journey of solving a two-sided marketplace cold start problem, being laughed out of VC meetings, operating under NDA for years, and finally breaking through with the just-signed lead for their Series A.

In This Episode, You'll Learn:
- Why Kumar left Samsung to solve what he saw as an inevitable and global merchant integration problem
- How Firmly built a universal API abstraction layer that connects to 11 million merchants with zero code changes required from the merchant
- Why keeping the merchant as the merchant of record and preserving first-party data is the core differentiator over Instagram Shop and TikTok Shop
- How AI agents infer and auto-generate native API connections to merchants who don't publish public APIs
- The brutal two-sided marketplace chicken-and-egg problem and how a breakthrough with a major social platform (under NDA) was the first sign of product-market fit
- Why agentic commerce creates a flywheel for merchants, payment gateways, and AI platforms alike
- Kumar's raw, honest advice for entrepreneurs, including why you should expect the journey to be harder than you imagined, and why resilience, family support, and financial runway matter as much as the idea

Kumar Senthil is the CEO and Co-Founder of Firmly, where he is building agentic commerce infrastructure that enables autonomous AI agents to discover, transact, and complete purchases seamlessly. Prior to that, he held leadership positions at Samsung.com, Groupon, Microsoft, and others, where he launched many products and built successful businesses.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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In this episode, we sit down with Praveen Seshadri, former Microsoft executive and co-founder and CEO of Thunk.AI. He previously co-founded AppSheet, which was acquired by Google. 

Praveen shares his journey from leaving Microsoft at age 40 to navigating five pivots over two years before discovering product-market fit with AppSheet. He discusses how the company pioneered no-code and product-led growth, the importance of customer-led development, and the lessons learned from building and scaling a startup.

The conversation also explores his latest venture, Thunk.ai, where he is focused on using generative AI to automate business workflows. He shares insights on the current state of AI, the challenges of reliability, and why AI has the potential to fundamentally reshape how work gets done.

In this episode, Praveen talks about:

- His transition from Microsoft to entrepreneurship
- The journey from multiple failed ideas to building AppSheet
- The rise of no-code and product-led growth
- Key lessons on fundraising, team building, and customer focus
- The opportunities and limitations of AI in business today

Whether you’re an entrepreneur, technologist, or builder, this episode offers a candid look at what it really takes to build, pivot, and succeed in a rapidly changing technology landscape.

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Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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In this heartfelt episode, Monish Darda remembers Samir Bodas not just as the CEO and co-founder of Icertis (https://www.icertis.com/), but as a close friend, co-founder, and extraordinary human being. He shares the origin story of Icertis, the trust that defined their partnership, and the values that shaped the company’s culture. Icertis is the market leader in Contract Lifecycle Management.

This is a moving conversation about entrepreneurship, friendship, resilience, and the legacy Samir leaves behind.

In this episode:
- Samir Bodas’s legacy as a founder, leader, and mentor
- The origin story of Icertis and an unexpected path to product-market fit
- What makes a great co-founder relationship
- The meaning behind Icertis’ “FORTE” culture
- Navigating leadership through personal and health challenges
- Lessons on resilience, purpose, and building a lasting impact

Monish Darda is a cloud-technology pioneer and serial entrepreneur with a 30-year track record in the enterprise software space. As CTO and Co-founder of Icertis, Monish has overseen development of the Icertis Contract Intelligence (ICI) platform, the leading contract management solution in the cloud. Monish has also led Icertis’ successful deployment of cutting-edge AI and blockchain technologies, which have earned Icertis numerous industry accolades including recognition on Forbes’ prestigious AI 50 List for two years in a row. Monish has a BE in Mechanical Engineering and a Master’s degree from Florida Atlantic University.

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast

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What happens when a former investment banker turns a life-changing personal experience into a startup? In this episode, Preeti Suri, founder of Adventure Tripper, shares how she built a curated marketplace for multi-day adventure travel—connecting travelers with vetted local guides around the world.

Preeti Suri is the Founder and CEO of AdventureTripr, a global adventure and wellness travel marketplace offering curated experiences across 50+ countries. A Chartered Accountant, CPA, and INSEAD MBA, she previously built a career in Big Four firms and investment banking before pivoting to entrepreneurship. Inspired by her own healing journey through the outdoors, she founded AdventureTripr to help people improve their physical, mental, and emotional well-being through movement, nature, and community.

Preeti discusses the challenges of launching during COVID, the role of AI in travel planning, and why curation and human expertise still matter in an AI-driven world. She also shares the deeply personal story behind her entrepreneurial journey and the mindset required to build a mission-driven company.

In This Episode, You’ll Learn
- How Preeti Suri transitioned from consulting and investment banking to founding Adventure Tripper
- The gap in the travel industry around curated multi-day adventure experiences
- Why curation and vetted local guides matter more than endless search results
- How the company pivoted during COVID and expanded from 5 destinations to nearly 50 countries
- How AI is changing travel planning—and why human expertise still provides an edge
- Adventure Tripper’s marketplace model and why fulfillment and post-trip support are key differentiators
- Why the company focuses on a B2B-led growth strategy rather than traditional consumer marketing
- Lessons from building a startup as a woman founder—and the mindset needed to overcome obstacles

Brought to you by TiE Seattle
Hosts: Shirish Nadkarni and Gowri Shankar
Producers: Minee Verma and Eesha Jain
YouTube Channel: https://www.youtube.com/@fromstartuptoexitpodcast