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/ Chapters: (00:00:40) Introduction(00:02:14) How Anna Baird got into tech with an accounting major?(00:06:13) Changes in the sales profession since COVID.(00:09:56) Creating a go-to-market strategy.(00:12:38) Balancing growth and profitability.(00:15:05) Building a high-performance sales team.(00:18:31) Why Madrona?(00:22:21) Don't try to make failure look pretty.(00:24:27) Is AI going to take all the sales jobs away? (00:25:43) Book recommendation.

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 Maria Gilfoyle, a venture capitalist with a design-first mindset focus. She shares her journey from wanting to become an artist to her career in venture capital. Highlights include the importance of user needs, user-focused investment decisions, analyzing companies' industry focus and go-to-market strategies, essential books for founders, and exercising as a form of relaxation.

Troop Travel founders Dennis Vilovic and Leonard Cremer discuss the startup journey, including finding the right problem to solve, when to bring on experts, identifying the right investors, and the importance of working closely with customers. They also touch on strategic meeting location selection, the benefits of cloud native technologies in the travel industry, integrating data providers, building a global team, and their vision for the future of Troop Travel.

Get to know Madrona Managing Director Karan Mehandru. Learn what drew him to venture capital and working with founders, what he looks for in founders, what he thinks founders should look for in VC partners, and what he enjoys doing outside the office.       (00:00:00) Introduction (00:01:00) Madrona Managing Partner Karan Mehandru's background (00:01:33) Why venture capital (00:02:50) Founders: Become the best version of yourself (00:04:58) Understand the person behind titles and roles (00:05:44) What Karan looks for in founders (00:06:52) Visionary founders (00:07:34) The role of grit and intellectual honesty (00:08:50) How Founders should select partners/investors (00:11:36) Biggest changes Karan's seen over his career (00:13:56) What has stayed the same (00:14:52) Cats or dogs (00:15:46) Karan's book recommendation (00:17:07) What Karan does outside of the office

Today, Madrona Managing Director S. Somasegar talks with Statsig founder and CEO Vijaye Raji, who spent 20 years at Microsoft and Facebook before launching Statsig as a way to bring the powerful tools he was used to using inside Facebook to all builders. Statsig experimentation platform and automated AB testing helps companies make product decisions in a data-driven way at scale, which means shipping the right products faster. Vijaye and Soma go way back and take a little trip down memory lane, talking about Microsoft’s Small Basic. But then they dive into what it’s like transitioning from big tech to a founder, the importance of data-driven decision-making, integrating AI into those decisions, identifying the ideal customer profile, and learning how to sell your product. Something that did not come naturally to Vijaye. He and Soma talk about all of this and so much more.   You can read a transcript of this conversation here: https://www.madrona.com/statsig-founder-vijaye-raji-product-building-launching-a-startup-ai/