From Startup to Exit

Send us a text We’re excited to feature Yifan Zhang, Managing Director at AI2 Incubator, one of the most successful AI incubators in the world, born out of the Allen Institute for AI and backed by a newly announced $80M Fund III. Yifan is a 2x founder and CEO, Entrepreneur “50 Most Daring Entrepreneurs” honoree, and Forbes 30 Under 30 alum. Her journey spans building and exiting venture-backed startups, navigating extreme founder adversity, and now helping the next generation of AI founders go from idea to impact. In this episode of From Startup to Exit, Yifan shares: How AI2 Incubator works differently from studios, accelerators, and traditional VCs What they look for in founders, and why ideas matter less than resilience and execution Why vertical, agentic AI applications are winning right now How AI startups are shifting from per-seat SaaS pricing to per-task, outcome-based models What it really takes to survive the founder “trough of adversity” and come out stronger Why Seattle may be the most underappreciated AI startup hub in the world This conversation is a must-listen for AI founders, operators, investors, and anyone building in the agentic AI era. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Send us a text Join us for a dynamic highlight reel featuring short segments from the 2025 season of From Startup to Exit, TiE Seattle’s flagship podcast showcasing world-class entrepreneurs, innovators, and industry leaders sharing candid insights from their journeys. Each mini-segment brings you the essence of these remarkable conversations — from foundational lessons in product and leadership to reflections on how technology shapes markets and culture.  We kick things off with Paul Maritz, discussing his pivotal role in Microsoft’s product strategy during the Windows and server era and how a deep commitment to innovation shaped a career spanning multiple iconic tech companies. Next, Jeff Raikes reflects on building transformative software platforms like Microsoft Office and his later work in global philanthropy focused on equity and systems-level impact. Robbie Bach takes you inside the historic launch of Xbox, offering a rare behind-the-scenes look at driving innovation within a legacy tech giant. Meanwhile Steve Wood shares foundational memories from Microsoft’s early days as the sixth employee, emphasizing the importance of grit and experimentation in startup culture.  We also spotlight Brad Chase on the launch of Windows 95 and the strategic decisions that made it a defining moment in personal computing; Laura Jennings on shaping MSN into a major internet portal; and modern voices like Sabrina Wu, who breaks down the future of intelligent applications and the role of AI in venture investing. Yash Wagh delivers insights from his startup journey with Gone.com and building sustainable commerce models. Ece Kamar closes with a forward-looking conversation on responsible AI, sharing how human-centered frameworks will guide the next phase of technological growth. Whether you’re an entrepreneur, technologist, or curious learner, this highlights compilation is packed with actionable wisdom from leaders who’ve navigated the path from startup to exit. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Send us a text Join us as Team Kymavi, the TYE Global winner, discusses their groundbreaking solution addressing environmental challenges through biodegradable bags, and Team Key Beauty, creators of an AI-driven makeup matching platform for women of color, shares their journey in redefining inclusivity in beauty. The teams dive into their experiences with market research, customer validation, and developing sustainable business models, highlighting how mentorship and the TYE program helped them refine their ideas, build essential entrepreneurial skills, and prepare for global success. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Send us a text In this episode, we sit down with Dr. Ece (AJ) Kamar, Director of the AI Frontiers Lab at Microsoft Research, and one of the leading voices in Responsible AI. With over 15 years at Microsoft, Ece has played a pivotal role in shaping how AI systems are designed to collaborate with humans safely and effectively. She shares her journey from earning a PhD at Harvard University, where she researched how AI agents can become human partners, to leading responsible AI efforts at Microsoft and tackling challenges like fairness, reliability, safety, and hallucinations in large-scale models such as GPT-4. In this insightful conversation, Ece talks about: - How early research in human-AI collaboration laid the foundation for today’s AI agents - The evolution of AI through scalable data, deep learning, and generative models - Her pioneering work on Responsible AI frameworks at Microsoft - The emerging challenges and opportunities in the era of generative AI Whether you’re an entrepreneur, technologist, or researcher, this episode offers an inspiring look into how responsible innovation will define the next generation of AI systems. Tune in to learn how human-centered AI is shaping the future - responsibly. To ensure you don't miss other episodes like this, subscribe to our podcast! Linkedin: https://www.linkedin.com/in/ecekamar/ Sponsored by: JPMC Private Banking Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Send us a text Yashovardhan Wagh is the co-founder & CEO of Gone.com, a Seattle-based circular commerce company giving quality goods a second life through local supply chains. He previously built supply chains for Amazon and other Fortune 100 companies. His mission: to build a national circular economy so future generations can thrive on a healthy planet. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Send us a text In this episode, we talk to Sabrina Wu who is an Investor at the famed VC firm Madrona Ventures. Sabrina shares her thoughts about closed source vs open source, agentic applications and the emergence of multi modal applications.  Sabrina joined Madrona’s investment team in 2021 and focuses on sourcing and evaluating new investment opportunities from Seed through Series C across Madrona’s core investment themes. She also supports the growth and strategy of current portfolio companies. Sabrina is particularly interested in intelligent applications, enterprise software, and data/AI products. Sabrina and Madrona Partner Vivek Ramaswami author the biweekly newsletter Aspiring for Intelligence where they share thoughts about the future of intelligent applications. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

In the 5th installment of the Microsoft@50 series, we interview Brad Chase, who was the SVP in charge of the launch of Windows 95. Later on, he took over the reins for MSN. Brad joined Microsoft in 1987 and was the first product manager responsible for the launch of the Microsoft Office on the Mac. Later he became the Group Product Manager for MS D0S 5.0. Brad negotiated the licensing of the famous Start Me Up song by the Rolling Stones that was used in Microsoft ads for Windows 95. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

In this 4th installment of the Microsoft@50 series we bring you Steve Wood who was the sixth employee at Microsoft. He was recruited out of Stanford where he completed his Masters in Electrical Engineering. He went on to work at Microsoft's Albuquerque office in 1976 where he had the opportunity to work closely with Bill Gates and Paul Allen. He worked on the FORTRAN compiler before becoming a General Manager. He left Microsoft in 1980 and later joined Asymetrix and found Starwave with Paul Allen. He became a serial entrepreneur starting companies such as Wireless Services Corporation. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

This is the 3rd installment of the Microsoft@50 series. We interview Robbie Bach, who was the Chief Xbox Officer at Microsoft and the founder of Xbox at Microsoft. Before founding Xbox, he ran Microsoft Office and made it into the standard it is today. After 22 years at Microsoft, Robbie announced his retirement from Microsoft effective in the fall of 2010. Robbie has spoken to corporate, academic, and civic groups across the country and in 2015 completed his first book, Xbox Revisited: A Game Plan for Corporate and Civic Renewal, followed by the Wikes Insurrection. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

This is the 2nd installment of the Microsoft@50 series. We interview Jeff Raikes, who was President of the Business Systems Division at Microsoft. Jeff was the one of the senior most executives at Microsoft after Bill Gates and Steve Ballmer. Jeff served as a member of the company’s senior leadership team that set the overall strategy and direction for the firm. He began his career with Microsoft in 1981 and was instrumental in creating the Microsoft Office suite of productivity applications. Jeff Raikes is a co-founder of the Raikes Foundation with his wife, Tricia. The Foundation works toward a just and inclusive society where all young people have the support they need to achieve their full potential. Key areas of focus include reimagining an educational system that creates conditions for all students to succeed; ensuring housing stability for youth; building a fair and representative democracy; and supporting donors and philanthropic organizations in moving resources toward justice. Jeff is the former CEO of the Bill and Melinda Gates Foundation, where he led the foundation’s efforts to promote equity for people around the world. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

In this first installment of the Microsoft@50 series, we interview Paul Maritz who was the third most senior executive at Microsoft. From 1986 to 2000, he worked at Microsoft and was on its executive committee. He became executive vice president of the Platforms Strategy and Developer Group and part of the 5-person executive management team. He was often said to be the third-ranking executive, behind Bill Gates and Steve Ballmer. He was responsible for essentially all of Microsoft's desktop and server software, including such major initiatives as the development of Windows 95, Windows NT, and Internet Explorer. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Learn about Simbian,  an AI security company. Simbian is the first security company to accelerate security by empowering every member of a security team, from the C-Suite to frontline practitioners, to craft tailored insights and workflows for their unique security needs - ranging from complex investigation and response to governance and reporting. Learn how they pivoted from providing security for Gen Ai to leveraging Gen AI to creating agents that speed up security workflows and investigations. Sumedh is the Chief Product Officer at Simbian, a cybersecurity startup that builds AI Agents to autonomously handle security operations such as investigating security alerts, hunting for threats, and filling questionnaires. Previously Sumedh was Director of Security programs at Meta, where his favorite project was to measure business outcomes of security. Earlier he was Partner GPM at Microsoft, where he led the product teams for data security products for cloud customers. Sumedh did his B.Tech in Computer Science from IIT Bombay and MS in Computer Science at University of North Carolina. Sumedh lives near Seattle and enjoys the beautiful Pacific Northwest outdoors. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Listen to our 2025 Annual Investment Outlook Panel with four top VCs based in Seattle and the Bay area. Get their perspective on the investment climate in 2025 and their plans to invest specifically in AI-based startups. See how they did with their 2024 forecast and what their big predictions are for 2025. Tim Porter, Managing Director, Madrona Ventures Tim joined Madrona in 2006 and invests in B2B software companies in the Pacific Northwest. He is currently interested in intelligent applications and SaaS, cloud-native software infrastructure, the modern data stack, machine learning, DevOps, and cybersecurity. He is also a board member of numerous Madrona portfolio companies. Sudip Chakrabarti, Partner, Pruven Capital Sudip is a partner at Pruven Capital where he works with companies that are transforming the enterprise, cloud and infrastructure markets.  Sudip's past investments include Exabeam, Heptio, Serverless.com, Datacoral, Spotnana, Temporal, Tesorio and Polly. He had also been a board observer at Databricks, Digital Ocean, Actifio, Mesosphere and Samsara. Kellan Carter, Founding Partner, FUSE Ventures Kellan Carter is a founding partner of FUSE where he focuses on early-stage investments in intelligent software in both horizontal and vertical categories.  He currently sits on the Boards of Zuper, Pictory, Avante, Owl, Xemelgo and PDM Automotive. Suman Natarajan, Senior Principal, B Capital Suman Natarajan is a Senior Principal at B Capital’s San Francisco office, where she invests in startups powering the enterprise, across domains such as cybersecurity, cloud infrastructure, DevOps, data and ML/AI, and B2B SaaS. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Learn about the founding of Otto from Mike Fridgen, the Managing Director of Madrona Venture Labs where this concept was incubated. Otto is your personal AI travel agent that seeks to be as valuable and insightful as a dedicated personal assistant. Otto offers enterprise-grade travel booking and servicing capabilities through an easy-to-use AI travel agent that autonomously plans, books, and manages your travel, even during your trip. As Managing Director of Madrona Venture Labs (MVL), Mike Fridgen leads the studio's mission to partner with founders from day one to create extraordinary companies. Mike co-founded multiple MVL studio funds that have created and invested in 30+ companies with aggregate funding of $270m+ and a total valuation of $700m+. Before MVL, Mike was the founding CEO of Decide, which was acquired by eBay in 2013. At eBay, Mike was the General Manager of the Seattle-area office and the global product leader for professional selling experiences. Prior to that, he was the founding head of product at Farecast, which was acquired by Microsoft in 2008. Since the late 90s, he has been a founding member of three venture-backed consumer technology companies. Mike is an active advisor and board member of dozens of startups. He is on the LPAC of Pack VC and has served on the University of Washington's Buerk Center for Entrepreneurship board since 2014. He is a graduate of the University of Washington and Harvard Business School. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

2024 has been an incredible year for TiE Seattle’s From Startup to Exit podcast – featuring inspiring conversations with entrepreneurial leaders, innovators, and changemakers. As the year ends, we’re excited to share the Top 4 Episodes of 2024 that you don’t want to miss! The Founding of OfferUp - Nick Huzar: https://www.buzzsprout.com/2234096/episodes/13413716 The Founding of Rover & the Vision Behind Pioneer Square Labs - Greg Gottesman: https://www.buzzsprout.com/2234096/episodes/13615903 Mega-Successful Exits: Chronus & Ally.io - Vetri Vellore: https://www.buzzsprout.com/2234096/episodes/13899931 Developer Joy Through Generative AI - Rajeev Rajan: https://www.buzzsprout.com/2234096/episodes/15463924 Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Smartsheet is a major success story for the Seattle Tech ecosystem. Smartsheet was founded in 2005 as a workplace management system based on a spreadsheet style architecture. In this episode, Praerit Garg (PG) talks about the early product vision for Smartsheet. How, unlike dedicated product management tools like Asana, Smartsheet is very flexible and adapts to a number of workplace management scenarios. PG discusses the new product innovations that Smartsheet has introduced based on AI. As a startup founder himself, PG shares some of the key lessons that he learned in starting a startup. Praerit Garg is President of Product & Innovation at Smartsheet. He is passionate about building a product and engineering culture of innovation that scales, finding simpler solutions to hard problems, and delivering great experiences for our customers. PG has more than 25 years’ experience building large-scale distributed systems and internet services. Prior to Smartsheet, Praerit was a general manager at AWS for identity, access, and directory services. Previously, he co-founded Symform, a distributed internet storage startup which was acquired by Quantum. PG was also at Microsoft for 12 years, where he was responsible for many of the user identity, access, and encryption features in Windows. While there, he led the delivery of distributed systems management capabilities across multiple Microsoft products and was part of the team that built Active Directory. PG is also co-inventor on more than 25 patents.  PG holds a master’s degree in computer science from Purdue University. He loves to travel with his family, experiencing different cultures and their food, art, architecture, and history. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

Many of the large language model providers have built their LLM models by scraping data from websites and open source sites. Some have licensed the content like Open AI has done with Reddit. Nonetheless, many of these LLM providers have been sued for illegally copying data for which they have no permission. In this podcast, Adam shares his thoughts on the Fair Use doctrine and whether that protects the LLM providers' ability to use publicly available web content to build their models. Here's also an interesting article that Adam has written for developing, extending and using Generative AI models. Adam Shevell is a partner in Wilson Sonsini’s San Francisco office, where he co-leads the firm’s technology transactions practice in the city. Adam advises technology companies and their investors at all stages of company development, from pioneering start-ups to leading global enterprises, angel investors, venture capital firms, and other institutions in the start-up ecosystem.  Adam represents leading Silicon Valley companies on complex and strategic transactions involving cutting-edge innovations and the launch of new products. By understanding his clients’ products, markets, and business priorities, and by building deep and lasting relationships, Adam provides creative and pragmatic advice focused on delivering effective results. Adam also works closely with Canadian start-ups on their U.S. expansion, fundraising, strategic partnerships, and exit transactions, and with Canadian venture funds investing in U.S.-based companies. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

You may not think of the State of Louisiana as a software innovation hub but it is doing a lot to attract startups to its state. It has a $100 million seed capital fund to match VC investment dollar for dollar. It is willing to rebate 25% of your software development dollars for software development done in its state. It is also providing sales tax rebates to attract large data centers to its state. Josh Fleig is responsible for fostering innovation and entrepreneurship across the state, while assisting small businesses with access to award-winning programs and services designed to accelerate growth and elevate Louisiana’s standing as a hub for innovation and high-value jobs. He is an experienced senior executive with over 20 years at the intersections of technology, economic development and education. Most recently, Fleig served as the Senior Vice President of Business Development at Greater New Orleans, Inc., where he led his team to developing a project pipeline of over $20 billion. Under his guidance, the team engineered strategies to develop key industries across Louisiana’s Southeast Region, with initiatives ranging from entrepreneurship and innovation to future energy and entertainment. Before his tenure at GNO, Inc., Josh was a trailblazer in the growth of Louisiana’s technology industry. Starting with the Jindal administration in 2012, he was the architect of a recruitment strategy that sparked dozens of software and digital media project wins at Louisiana Economic Development. His contributions included the co-creation of the state’s Entertainment Development Fund. Earlier in his career, Josh established a track record of innovation as the Director of Media and Brands at SinglePoint (now Bally’s Corporation). There, he managed publisher relationships for the SaaS business, driving interactive TV engagements that captivated audiences across major broadcasters like CBS, Disney, Viacom and Discovery. His journey into the media industry began at NBCUniversal, where he thrived as a technical producer in interactive media product design, creating hundreds of groundbreaking fan engagements for NBC Sports, Bravo, Syfy, MSNBC, CNBC and more. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

These days you will often call into customer service for a company whose product you are using and will be connected to an agent with a foreign accent. For many Americans, this can be a challenging experience as they cannot understand what the agent is saying because of their accent. Foreign agents have also complained that it can be a dehumanizing experience. This can result in a low Net Promoter Score for the foreign call center which reduces the revenues they can charge for their services. Soundwave is an AI application that moderates the accents of foreign call center agents. It works as the agent talks into their microphone. Then, their voice goes through an AI model in real-time and returns with a moderated accent. The caller hears the response in the moderated accent.  The Soundwave product was conceived of by young high schoolers under the auspices of the TiE Young Entrepreneur (TYE) program. They won the TYE Globals finals in 2024. TYE is a fantastic year-around program to guide high school students to create and launch their first real business. Students are guided through each step of starting an enterprise, from brainstorming the idea to developing a product prototype to pitching to investors. Classroom learning is blended with real-world experimentation and validation, to obtain product-market fit. This program culminates in the regional finals event being held this year and a global competition. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567

On our one year anniversary, we are releasing this terrific episode with Jay Bartot, partner at Madrona Venture Labs (MVL). Jay talks about the model that MVL uses to work with startup founders and whet startup ideas. Like many technology entrepreneurs, over the last 18 months, Jay has been deeply immersed in Generative AI technology, building experimental products, and testing the capabilities as well as limitations of the new AI frontier. Having seen and worked with slowly evolving AI and machine learning technologies over 25 years, his early experimentation with LLMs (large language models) quickly led to the realization and excitement that difficult problems he grappled with for many years (e.g., robust natural language understanding) are now virtually solved. The essence of his enthusiasm for the advances in capabilities Generative AI technology brings to entrepreneurs and startups was captured when he was recently overheard saying, “I mean, holy shit - these things are fucking awesome!” Jay Bartot joined MVL in 2016. At MVL, Jay leverages his extensive experience in software engineering and machine learning to develop innovative, AI-driven software solutions. His expertise extends beyond technical execution, encompassing a spectrum of strategic elements of company creation and building. Journey to MVL Jay's immersion into computing began in the late '80s when he was swept up in the personal computer revolution, learning to compose and play music on his Apple Macintosh in college. This ultimately sparked his interest in software development, signal processing, and computer graphics. He quickly discovered the joy and power of building and distributing his own software to his friends and family, not to mention being paid to do what he loved. During the internet boom of the mid-90s, Jay joined his first startup, where he was introduced to the value of data, machine learning, and venture capital. Over the next 15 years, Jay co-founded several data-centric machine-learning startups in various verticals, such as e-commerce, online advertising, travel, medical informatics, and consumer video applications. These startups were later acquired by major companies such as Nielsen/NetRatings, Microsoft, Alliance Health Networks, and Hulu. Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Producers: Minee Verma and Eesha Jain YouTube Channel: https://www.youtube.com/@tieseattle567