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.

Akhtar Badshah is an expert on social impact, philanthropy, CSR and international development, an author and artist. He is the co-founder of Purpose Mindset, founder and Chief Catalyst of Catalytic Innovators Group a consulting practice focused on accelerating social impact through catalytic innovation. He a Distinguished Practitioner and at the University of Washington, School of Business (Bothell Campus) and Evans School of Public Policy and Governance. He also is a faculty lead at START Center at the Department of Public Health. 

Brad Chase 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.

Greg Gottesman is a Managing Director and Co-Founder of PSL. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona Venture Group, where he worked for almost 20 years.  He also co-founded and led Madrona Venture Labs.

Greg represents PSL on the boards of Boundless, Ever.green, Joon, and Kevala. He is also the founder, current board member, and former CEO of Rover.com.

 Sunny Gurpreet Singh is an entrepreneur and philanthropist based in Seattle, US. He is the founder of Roundglass, a global Wholistic Wellbeing organization established in 2014. Through his experience in the US healthcare system, Sunny realized the importance of a proactive wellness approach. Roundglass offers the Roundglass Living app, which provides technology-driven solutions, expert-led content, and access to renowned wellbeing coaches and mental health experts. It serves as a tool to assist people in making positive, long-term changes and enhancing their lives.

Jai Jaishima is a Seattle-based technology entrepreneur with expertise in AI enabled product development and data science. Jai has a Ph.D. in Electrical Engineering with a focus on AI/Image Processing/Information Retrieval from the University of Washington. Over a nearly 30 year career, Jai has founded or held leadership roles at four start-ups that leveraged AI/Machine Learning to build software applications. He was CTO at Hitch Works Inc., acquired by Service Now in 2022, which deployed AI/Large Language Models (LLMs) to help employees and their employers take a skills-based approach to work and career progression. Jai was also CEO and Founder at Appnique which developed privacy preserving advertising technology solutions using AI/LLMs. At Microsoft, AOL and RealNetworks, Jai led pioneering initiatives in the digital distribution of music and video content that also ensured that user privacy was respected and the rights of creators and copyright holders were protected.

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. 

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.

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.

Joseph is currently CEO of CreatorsAGI Inc, an AI startup dedicated to empowering creators with Artificial Generative Interaction capabilities. He has been an AI leader all of his career, and served as the Vice President of Alexa Shopping at Amazon.com, the Chief Technology Officer of Compass Inc, and as Microsoft’s Corporate Vice President of AI. During his tenure at Microsoft, he held product and engineering responsibility for all Azure AI, enterprise database, and big data products. He built Azure ML, the first Machine Learning as a Service platform in the cloud. Prior to Microsoft, Joseph spent nine years as a VP at Amazon where he managed the Global Inventory Platform for Amazon’s Consumer Business, and built the machine learning, data warehouse and Transaction Risk Management teams. Joseph holds a PhD in Neural Networks from the University of Texas at Austin. You can follow him on Twitter and read about what he finds exciting in AI on his substack, Generative AI substack.

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.

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.

Laura Jennings was the Vice President in charge of MSN and one of the senior most female executives at Microsoft in her time. Laura was the Microsoft executive who shifted MSN's strategy as a proprietary online service to becoming one of the top portal's on the internet. I worked for Laura and together we bought Hotmail and got into the search business in partnership with Inktomi. In 1999, Laura Jennings launched a new version of MSN with personalization, integrated web email and search.

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.

Nick Huzar is the co-founder and former CEO of OfferUp for more than a decade. He is currently operating as a board director, brand evangelist, and advising the CEO on strategic projects. Nick's experience lies in building two-sided marketplaces from the ground up. Through this, he has raised over $380M in financing from leading investors including A16Z, TRowe, Tiger, Allen.co, GGV, Coatue, and more. He is currently focused on simplifying the complexity around climate change via my weekly video podcast @ www.stufftv.org. Additionally, he will ride anything with a board (wake surf, skate, wing foil, snowboard..).

1 in 5 people over the age of 14 used OfferUp in 2021. OfferUp now facilitates billions of dollars in transactions every single month. They most recently branched out from shopping and now have a marketplace for local jobs as well.

From 1986 to 2000, Paul Maritz 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.

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. 

Raj has a common theme with his startups Snapfish and Fitmob. Both of them needed to be pivoted and focus on survival. He found buyers for both and his mantra to founders is to dissolve the ego and make sure your company sees another day to battle. He spent several years at Mayfield and invested early in Lyft and led the autonomous driving strategy for Lyft.

Raj is a co-founder and managing partner at Climactic, a venture capital fund focused on climate tech. He was also a strategic advisor at Lyft, former CEO/co-founder of Snapfish and Fitmob (now ClassPass), and a former managing director at Mayfield Fund.

Rajeev embarked on his career at Microsoft as a developer after a sabbatical from his Ph.D. to build upon his internship experience in Seattle the previous summer. In this episode, he delves into how his journey and interactions with various leaders have influenced his own leadership style as the CTO of Atlassian.

Rajeev Rajan is the Chief Technology Officer at Atlassian where he oversees Atlassian Engineering, IT, Security and Trust, and the Engineering Operations teams. As CTO, he is focused on our Cloud transformation and continuing to grow Atlassian into a world-class engineering organization.

Rajeev previously acted as the Vice President and Head of Engineering for Meta and spent over two decades at Microsoft, where he held a number of roles, including building and leading the team responsible for Office 365's Cloud Infrastructure.

Rob Eleveld hails from Grand Rapids, Michigan. After college, he spent 5 years on active duty as a submarine officer in the United States Navy, serving aboard the fast attack submarine USS Batfish. Across a 25-year career in tech software and data companies, Rob is a 4-time CEO of early-to-mid stage companies in software and data beginning in 2000 with Vykor Inc., which he co-founded and led. Over the past 10 years at Whitepages Inc., he served in executive roles and eventually became CEO in 2016. Rob led the spinoff of the enterprise unit, rebranded Ekata Inc. in 2019, which Mastercard acquired in 2021. Rob has a BA in Engineering Sciences from Dartmouth College and an MBA as well as an MS in Manufacturing Systems Engineering from Stanford University.

Robbie Bach 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.

Steve Wood 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.

Sudarshan Chitre brings over 25 years of experience in developing Data & AI products, having worked with leading technology firms including Microsoft, Amazon, and Oracle, as well as several innovative startups. Throughout his career, Sudarshan has transitioned from roles in software development to executive leadership, including that of CEO. He remains deeply engaged in the evolving landscape of technology as an avid learner and an advocate for its practical applications. He holds co-inventorship of more than 10 patents in the fields of databases, data synchronization, and IoT.

Currently, he leads the AI Product and Engineering team at Icertis. Sudarshan is academically credentialed with a BS and MS in Computer Science and an MBA from the Haas School of Business, UC Berkeley, and Columbia Business School.

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.

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.

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.

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.

When Vetri Vellore was given the responsibility to turn around the Systems Management Server business at Microsoft, it was a failing business. In fact, at a business review, Bill Gates famously threw his deck back to him telling him to shut down the business. But Vetri persisted and completely turned it around. Soon Vetri embarked on a remarkable entrepreneurial journey where he successfully started and exited two businesses - Chronus which was a mentoring platform and Ally.io which was a platform for managing OKRs (Obejectives and Key Results). Vetri bootstrapped his first business but raised substantial funding for his second. Listen in to hear the inspiration he got to start both businesses and his thought process behind raising VC funding.

Follow the journey of Vikram Chalana, a Seattle based entrepreneur who started his entrepreneurial journey with an enterprise product called Win Shuttle that allowed MS Excel users to exchange data with SAP. He grew the company to significant revenues and ultimately sold the company to a Private Equity firm. More recently, he has started a Gen AI company Pictory. AI that allows creators to convert text into video that is the leader in the space.

Vikram is an engineer turned serial entrepreneur.  He is currently building Pictory to enable anyone to turn their message into engaging videos quickly & easily. He previously created and scaled Winshuttle, an enterprise software in the data management space, to over 300 global employees. He holds engineering degrees from Indian Institute of Technology and from University of Washington.

Vivek has spent his career investing in high-growth companies across software and fintech. Prior to Madrona, Vivek helped launch the venture capital arm of Steadfast Capital, where he led investments in Zapier, Klaviyo, Lucid, Forethought, Sendbird, Jumpcloud, Algolia, Wealthsimple, and other high-growth companies.

Prior to Steadfast, Vivek was a Principal at Redpoint for five years, where he helped source or work on investments in SentinelOne, Nubank, Bright Health, Cockroach Labs, Hashicorp, and others. Vivek started his career in technology investment banking at Goldman Sachs, advising clients on M&A and IPO opportunities in the software and consumer internet sectors.

As part of the Madrona investment team based in California, Vivek partners with ambitious founders across enterprise software, cloud infrastructure, data tools, intelligent applications, and fintech. He focuses on helping founders who have achieved product-market fit scale to the next level.