Madrona Partner Vivek Ramaswami hosts May Habib, co-founder and CEO of Writer, a 2023 IA40 winner. Writer is a full-stack generative AI platform for the enterprise. In this episode, May shares her perspective on founding a GenAI company before the ChatGPT craze, building an enterprise-grade product and go-to-market motion with 200% NRR, whether RAG and vector DBs even have a role in the enterprise, the essential attributes she looks for when hiring, and some valuable lessons she learned from past experiences. It's a must listen for anyone building in AI.

Transcript: https://www.madrona.com/writer-ceo-may-habib-generative-ai-platform

(00:00) Introduction

(01:00) The founding story of Writer

(01:19) Understanding Writer's product and value proposition

(02:58) The importance of building your own AI models

(07:10) The role of vector databases and RAG in enterprise

(12:41) Navigating the challenges of enterprise sales in AI

(16:43) The essential attributes May looks for when hiring

(19:13) The journey of building a high-growth AI company

(29:27) Final thoughts and hiring at Writer

Hear from Madrona Managing Director Soma Somasegar as he discusses his path to venture capital by way of 27 years at Microsoft. He shares invaluable insights about what he looks for in a founder, the importance of passion in founders, the state of cloud technology, and the future of AI and Startups. Tim also shares Madrona's core principles, his favorite books for entrepreneurs, and his personal interests outside of work, including his passion for outdoor sports and the nonprofit Global Partnerships. This chat is a must-watch for aspiring entrepreneurs looking for insights into the venture capital world or strategies to capture an investor's eye.

(00:00) Introduction

(01:18) Soma's Journey from Microsoft to Madrona

(02:08) Choosing the Venture Capital Path

(03:31) Why Seattle and Madrona?

(05:33) Soma's Investment Focus: AI and Cloud Infrastructure

(08:00) Evaluating Founders and Teams

(11:17) Recommended Books for Founders

(12:20) Soma's Passion for Cricket

Madrona Partner Jon Turow hosts Gabriel Hubert and Stan Polu, the co-founders of a 2023 IA40 winner, Dust, which enables information workers to create LLM-based agents that help them do their own work more efficiently. They discuss the broader AI/LLM ecosystem, the merits and potential of horizontal vs vertical solutions, limitations of AI assistants, and the influence of Stripe on their business. The founders dive into the future use cases and adoption of AI in businesses and also touch on keeping humans in the loop of AI and software development.

Transcript: https://www.madrona.com/dust-bets-foundation-models-change-how-companies-work/

(00:00) Introduction and Overview

(01:31) The Trade-off Between Vertical and Horizontal

(02:48) The Power of Horizontal Approach

(08:26) The Influence of Stripe on Dust's Strategy

(10:45) The Future of AI and LLM Deployment

(18:23) The Role of Dust in Organizations

(21:37) The Potential of Dust as a Company OS

(28:32) The Future of Work with Dust

(33:30) The Success and Challenges of Dust

(36:08) The Potential of Dust and AI

In this episode of Founded & Funded, Madrona Managing Director Tim Porter talks to Craig McLuckie, who's most known as one of the creators of Kubernetes at Google. Madrona previously backed Craig's company, Heptio, and was excited to back his latest company — Stacklok. Stacklok is a software supply chain security company that helps developers and open-source communities build more secure software and keep that software safe. Tim and Craig discuss Stacklok's developer-centric approach to security, the role of open source in startups, the importance of open source and security, and they also hit on some important lessons in company building — like camels vs. unicorns – and where Craig sees opportunities for founders. It's a must-listen for entrepreneurs.

Transcript: https://www.madrona.com/founded-funded-stacklok-craig-mcluckie/

(00:00) Introduction (01:48) Stacklok and securing open source (05:35) Knowing where open-source tech comes from (08:45) What is Supply Chain Security (10:04) The Role of Developers in Security (13:50) The Power of Open Source in for Startups (18:22) The Importance of Culture in a Startup (camel v. unicorn) (22:37) The Three Jobs of a Founder (27:59) The Future of Stacklok and the Cloud Native Ecosystem (31:00) Opportunities for Founders

Madrona Investor Palak Goel talks with Arvind Jain, founder and CEO of Glean, which has raised about $155M since launching in 2019 and was named a 2023 IA40 winner. It should be no surprise that Glean is touted as the search engine for the enterprise because Arvind spent over a decade at Google as a distinguished engineer, where he led teams in Google Search. Palak and Arvind dive into Glean's vision to be the AI-powered personal assistants in the workplace, how AI should not be thought of as a product but rather as a building block to create a great product, the need for better AI models and tooling, and advice for founders in the AI space, including the importance of customer collaboration in product development, the need for entrepreneurs to be persistent – and so much more! Transcript: https://www.madrona.com/ia40-glean-arvind-jain-ai-in-the-enterprise/

(00:00) Introduction

(01:32) The Challenges/Opportunities of Building AI Products

(03:20) The Role of Glean in AI Applications

(04:55) Impact of AI on Different Industries

(06:17) From Prototype to Production

(08:46) Importance of Persistence and Customer Centricity

(10:32) Future of AI and Its Impact on Enterprises (13:07) AI is a Wave You Have to Ride

(14:48) AI is Bigger than Cloud

(16:35) Glean's Role in the Future of Work

(17:52) Advice for Founders and Builders

(20:44) The Impact of the Internet

(23:07) Glean's Product Evolution

(28:31) What Intelligent App Arvind's Excited About

(28:50) AI Trends Arvind is Excited About

Hear from Madrona Managing Director Tim Porter as he discusses his path to venture capital by way of mechanical engineering and Microsoft. He shares invaluable insights about what he looks for in a founder, the importance of customer focus, and the high priority he places on integrity. Tim also shares Madrona's core principles, his favorite books for entrepreneurs, and his personal interests outside of work, including his passion for outdoor sports and the nonprofit Global Partnerships. This chat is a must-watch for aspiring entrepreneurs looking for insights into the venture capital world or strategies to capture an investor's eye.

(00:00) Introduction (01:25) Tim's path to Venture Capital (02:55) Current Focus and Interests (06:36) Working with Founders (08:36) Attributes of a Successful Founder (12:08) Lessons Learned (12:48) Sticking to Madrona's Culture Amidst Changes (14:42) Book Recommendations for Founders (15:36) Personal Life and Hobbies

In this episode, Madrona Managing Director S. Somasegar and General Counsel Joanna Black discuss the fundamental role of a board in a startup's growth and development. They touch upon the importance of aligning strategic views with board members, managing disagreements, and effective governance to ensure that the organization is run efficiently. The duo offers numerous insights into the intricacies of board structure at different stages of a startup lifecycle, drawing parallels from recent events at OpenAI. The conversation covers the need for transparency, both in sharing good and bad news, and the necessity for a functional board reflecting a functional culture.

(00:00) Introduction

(02:12) Differences between Nonprofit and For-profit Boards

(03:03 Defining Governance and its Importance

(04:20) The Role of a Board in Early-Stage Companies

(06:33) Board Evolution with Company Growth

(09:09) Choosing the Right Board Members

(10:38) Navigating Disagreements and Conflicts within the Board

(13:00) The Importance of Transparency and Communication in Board Governance

(15:08) Conclusion and Final Thoughts

This week, Madrona Managing Director Karan Mehandru hosts Madrona Operating Partner Anna Baird. The operating partner role is a new one for Madrona, and we're excited to have her on the team to advise our founders. Before transitioning to board positions in the last couple of years, Anna was most recently the CRO at Outreach. Before that, she was the COO at Outreach, and before that, she was the CFO at several companies. That trifecta of C-Suite experience gives Anna a unique perspective to help founders navigate any blind spots they may have.

Anna and Karan, who is on the board of Outreach, dive into how the sales profession has changed, how the role of the CRO has changed since COVID, how to talk to customers, how to build high-performance sales teams, go-to-market strategy, AI's role in sales, and so much more. These two tackle it all, and it's a must-listen. Transcript: https://www.madrona.com/karan-mehandru-anna-baird-go-to-market-strategy/

Madrona Partner Aseem Datar hosts Tigera CEO Ratan Tipirneni. Tigera is in the business of preventing and detecting security breaches in cloud-native applications, and its open-source offering Calico is one of the most widely adopted container networking and security solutions out there. Aseem and Ratan dive into whether or not you should open source, the three business models founders should evaluate when thinking about commercializing an open-source project, how to compete with free, how product-led growth can really kickstart your business compared to traditional go-to-market, and so much more.

Words of wisdom from Ratan Tipirneni:

• You need to be thinking about commercialization even as you're launching the open-source offering.
• Wait to launch a commercial product until you reach a minimum critical mass in your community.
• Don't put everything in the open-source bucket. It leaves you no other option but to monetize through commercial support, which is not a very defensible business.
• Trying to compete with free by offering more free stuff is a losing battle.
• It is a fallacy to assume that just because you're offering free software a user will adopt it.
• Stick to fundamentals – be clear about who your end users are and what their pain points are. Everything else will take care of itself.
• Stars are a vanity metric that can be gamed. Signs of daily usage, the growth rate, and user feedback are better places to start.

Get to know Madrona Investor Maria Gilfoyle. Learn how she pivoted from wanting to become an artist into venture capital, her design-first mindset focus, what she looks for in founders, and what she enjoys doing outside the office.