Startup Project: Build the future

Nataraj interviewed veteran VC Matt McIlwain of Madrona Venture Group on Startup Project podcast. Matt shared his insights into the state of venture capital and the impacts of AI, drawn from his 20+ years of experience. Some key takeaways: 1. Venture is a "tale of two cities" now - later stage startups are struggling, earlier stage companies embracing AI are thriving 2. Seattle has unmatched talent but lacks local capital - still over-reliant on Silicon Valley VCs 3. Incumbents have the edge currently in leveraging AI due to data, customers, ability to integrate via APIs - but long term, AI-native startups will win out 4. Partnerships forming between big tech and AI startups provide startups with computing resources while allowing tech giants to take an open, marketplace approach to AI I highly recommend tuning in to hear Matt's take on venture capital, AI, and building an enduring company. Available on all major podcast platforms - link in comments!

In this episode, Nataraj spoke with John Staenberg, a veteran of the tech and venture capital world. John took Nataraj through his early days growing up in Omaha and attending Stanford University, where he was inspired by the culture of creativity and trying new things. After graduating, John worked in real estate and then got his MBA, also at Stanford. He became fascinated by the nascent world of venture capital and startups in Silicon Valley. John landed a job at Microsoft in the late 1980s, when the company was still small and growing fast. He described the exciting “change the world” energy there, where people worked tirelessly to spread personal computers. After Microsoft, John started his own venture funds focused on bridging Seattle and Silicon Valley. He's been involved with around 200 startups over his venture career. John reflected on missing out early on companies like Google and Amazon that became huge wins. But he's also had some big successes, like Seagate. He emphasized that surprise and timing are always at play in VC investing. Nataraj and John also discussed how venture capital has matured and become overcrowded, making it hard to generate outsized returns. So John has pulled back on direct startup investing. Pivoting gears, they talked about John's passion project - starting a wine business in Argentina 17 years ago. He saw it as a way to pursue his interests and bring people together. John then explained his latest venture to Nataraj - launching a search fund to invest in other funds that acquire small businesses for entrepreneurs. He believes this model can provide great returns and opportunities. Throughout his wide-ranging career, John has stayed focused on connecting people and giving back, including through the many events he has hosted. Follow Jon at https://www.linkedin.com/in/jonstaenberg/ Follow Nataraj at https://www.linkedin.com/in/natarajsindam/

In this episode of the podcast, we feature Ashmeet Sidana, the founder and Chief Engineer of Engineering Capital. Ashmeet has an extensive background in engineering and venture capital, with experience as the Director of Product Management at VMWare and as a venture capitalist. During the conversation, Ashmeet discusses various topics, including his experience developing the ESx Server at VMWare and leading seed rounds of companies like Azure Power and Tubi. He also shares insights into why venture capitalists prefer startups to stay private and the importance of investing in technical insights. Ashmeet also talks about his approach to getting in front of future founders and explains why he chooses not to invest in blockchain. He discusses the significance of large funding rounds in the AI seed stage and the value of investing in open-source companies. To learn more about Ashmeet Sidana and his perspectives on investing in startups with technical risks, you can listen to the full episode on platforms like YouTube, Spotify & Apple. Full conversation includes: - Being Director of PM at VMware & Venture Capitalist - Developing ESx Server at VMWare - Leading seed rounds of azure power (public & valued at $2B) - Leading seed investment at Tubi - Starting Engineering capital - Why vcs want startups to stay private - What it means to invest in technical insights - Getting infront of future founders - Not investing in blockchain? - Large funding rounds in AI seed stage - Investing in opensource companies

To stay up to date checkout ⁠⁠⁠⁠⁠⁠thestartupproject.io⁠⁠⁠⁠⁠⁠ & follow Nataraj on twitter: ⁠⁠⁠⁠@natarajsindam⁠ and on LinkedIn at ⁠https://www.linkedin.com/in/natarajsindam⁠ Join us in this captivating episode as we sit down with Joe Heitzeberg, a multifaceted entrepreneur who has navigated the world of technology and business with remarkable success. From his early days in the tech industry to founding his acclaimed venture Crowd Cow, Joe shares his incredible journey and valuable insights on various topics. 1. Joe's Entry to Technology 2. Working for Paul Allen 3. Import Furniture Business 4. Opportunity Cost of MBA 5. Building Viral VoIP App for MySpace 6. Selling Media Piston to Upwork 7. Starting Crowd Cow 8. Problems with Chicken in the U.S 9. Fundamental Shifts from AI 10. AI Tinkerers Follow Joe on LinkedIn at https://www.linkedin.com/in/joeheitzeberg To stay up to date checkout ⁠⁠⁠⁠⁠thestartupproject.io⁠⁠⁠⁠⁠ & follow Nataraj on twitter ⁠⁠⁠@natarajsindam and on LinkedIn at https://www.linkedin.com/in/natarajsindam

Tim Chen is the Managing Partner at Essence VC, an early-stage fund focused on data infrastructure and developer tool companies. He has over a decade of experience leading engineering in enterprise infrastructure and open source communities and companies. Prior to Essence, Tim was the SVP of Engineering at Cosmos, a popular open source blockchain SDK. Prior to Cosmos, Tim co-founded Hyperpilot with Stanford Professor Christos Kozyrakis, leveraging decades of research to disrupt the enterprise infrastructure space, which later exited to Cloudera. Prior to Hyperpilot, Tim was an early employee at Mesosphere and CloudFoundry. He is also active in the open source space as an Apache Software Foundation core member, maintainer of Apache Drill and Apache Mesos, and CNCF TOC contributor.

Aseem joined Madrona in 2021 after spending almost twenty years as an operating executive. He works alongside founders building the future of next-generation infrastructure (core, security, DevOps), intelligent applications, robotics, and automation. Full conversation includes: From Intern at Windows to GM at Microsoft Azure GM at Azure to Investing at Madrona Investing at Madrona Startups vs Big Tech in AI Commoditization of LLMs Difference between LLMs & Human Brains Follow Aseem on LinkedIn at https://www.linkedin.com/in/aseemdatar/ To stay up to date checkout ⁠⁠⁠⁠⁠thestartupproject.io⁠⁠⁠⁠⁠ & follow Nataraj on twitter: ⁠⁠⁠@natarajsindam

To stay up to date checkout ⁠⁠⁠⁠⁠thestartupproject.io⁠⁠⁠⁠⁠ & follow Nataraj on twitter: ⁠⁠⁠@natarajsindam⁠⁠ T.A. McCann is a serial entrepreneur with an impressive track record. He has founded and served as CEO of several successful companies. Some notable ventures include Senosis (acquired by Google), Gist (acquired by Blackberry), and Rival IQ, a leading company in marketing analytics. McCann's expertise extends beyond founding companies. He has also held senior roles at Microsoft, where he led divisions such as Exchange and the Mobile Services divisions. Additionally, he has worked as an EIR (Entrepreneur in Residence) at Polaris Venture Partners and Vulcan Capital. Full conversation includes: Becoming a professional sailor Working at microsoft exchange Starting 5+ companies (3 exits) Working for Paul Allen & building Startup Studio Vulcan Labs Selling Gist to Blackberry Rival IQ Synosis (acq by Google) Pioneer Square Labs Systematic customer discovery & customer development process Advice to entrepreneurs raising capital Is AI a step change? Who will capture value in AI? Big tech or startups? Follow TA on LinkedIn at https://www.linkedin.com/in/tamccann/

To stay up to date checkout ⁠⁠⁠⁠thestartupproject.io⁠⁠⁠⁠ & follow Nataraj on twitter: ⁠⁠@natarajsindam⁠⁠ In this episode Nataraj spoke to Taylor Black who co-founded Fizzy Inc. Post Fizzy Taylor worked at Innovation Science Fund & currently works as a Principal Product Manager at the Office of the CTO Incubator at Microsoft. Transcript: [00:00:00] Nataraj: I looked at the portfolio there then it's completely deep tech, uh, and sort of like invention based, uh, ideas. [00:00:08] Nataraj: Uh, so what was the process of like capturing and invention and taking and productizing it and, you know, making a return out of it? Like what was the thinking process there? [00:00:20] Taylor: So the, uh, and you can read Malcolm Gladwell's take on this in a, in an article where he described our invention sessions. Um, a and the invention sessions are a bit of a riff on like an innovation session or an envisioning session or things along those lines where you, you come up with wild ideas within a particular problem space, um, in a very unfettered sort of, Um, and the whole goal of this session is to generate as many ideas as possible. [00:00:52] Taylor: That's the sole ROI you're looking for in those sessions. Um, but there's certain conditions you set for success in those [00:01:00] sessions. And so the way that we ran those sessions, and I, and I, I ran, uh, a number of them, um, is that we would prepare for months ahead of time in gathering all of the materials that related to the problem. [00:01:14] Taylor: and by materials I mean the scientific research in a particular problem space, the, uh, market, uh, and startup landscapes of that particular problem space. Um, uh, things that people had written about it. Books, articles, um, you know, YouTube videos, everything, uh, along those lines. And the goal was to, um, inform. [00:01:43] Taylor: Kind of the fermentation moment of when you're thinking about a problem, all of these things w wouldn't themselves, um, not be a solution necessarily, but there are all the things that someone who wanted to be completely informed or as, as, as informed and possible as possible about a set of [00:02:00] problems. Um, Had all of the raw material there. [00:02:03] Taylor: We'd also do customer discovery, we'd do customer interviews to understand those pain points. We'd bring people in, um, uh, and run sessions with them where they would, you know, get deep into their own, um, the problems they were encountering so that everybody who is, and everybody who's part of the sessions had to. [00:02:22] Taylor: Understand those materials, uh, deeply. We'd even quiz them on occasion. Um, it also helped that, uh, bill Gates, um, uh, whenever he came to those sessions, he would have all of those materials like completely groced. And so you, you know, you needed to have them groced too so that you didn't, you know, uh, lose face in front of Bill. [00:02:44] Taylor: But, um, Uh, but the key, so we'd, we'd get everybody, all of those materials and have them go through them, uh, a good month or so before the actual sessions happened. Um, that gave everybody an, an even playing [00:03:00] field in terms of, you know, I may be a physicist, I may be a biz dev person, I may be, um, an attorney. [00:03:06] Taylor: I may be, uh, you know, a program manager, but I have all of the same raw material. Uh, and my own perspective on it that I can bring to these sessions. The sessions themselves, them, um, were set around particular problem spaces and we'd start, we'd start each, um, session and then there's a variety of different kinds of sessions that we ram. [00:03:28] Taylor: Um, Uh, with a lot of provocations, a lot of conversation, a lot of like wild thinking and post-it notes and whiteboards of just dumping ideas out, uh, that had occurred to people or occurred in conversation or happened in the, in the hallway outside. Um, and we get all those ideas down, documenting everything.

#56: Why Wordpress dominates internet?

To stay up to date checkout ⁠⁠⁠thestartupproject.io⁠⁠⁠ & follow Nataraj on twitter: ⁠@natarajsindam⁠ In this episode Nataraj spoke to Taylor Black who co-founded Fizzy Inc. Post Fizzy Taylor worked at Innovation Science Fund & currently works as a Principal Product Manager at the Office of the CTO Incubator at Microsoft. Transcript: [00:00:00] Nataraj: To me it always made sense for large companies to have some kind of incubator or accelerator model because one of the reasons I think we are seeing in this bear cycle, sort of like when the wave sort of, you know, falls down, you see who's naked scenario. [00:00:17] Nataraj: Um, I think any company which survives multi decades has to have multiple large businesses. Mm-hmm. . I think in a lot of ways, I mean, looking back, a lot of companies didn't, uh, look for long-term opportunities as much as they should. Like we can talk about like, uh, Amazon, you know, putting billion dollars into their phone, but I would argue the potential on the upside of suckers was so high they should have put in, you know, one more billion and tried the next version. [00:00:50] Nataraj: Mm-hmm. . Mm-hmm. , uh, and I. , like argue the same with Facebook in a sense. Like now they're doing this metaverse thing. [00:01:00] Um, and sort of again retreating that back now. But I feel like even Facebook with all its cash flow, uh, didn't really think, um, because they always self constrained themselves to be a social company. [00:01:14] Nataraj: Um, like I think that's sort of like a self-imposed mental model on themselves. Mm-hmm. , like, uh, I would not impose themselves like a social company. Yeah. You work good at Facebook and WhatsApp, but I mean, look at how many great technologies that came out from Facebook, open source community and like putting that social as a blanket on your company. [00:01:34] Nataraj: I think. Set a backstage for all these technologies, which could be, you know, productionized and, you know, capitalized. Mm-hmm. . Right. Uh, that's, I feel like a lot of companies, especially the large companies, are with very good cash flow sort of mixed out on business opportunities because of that reason. [00:01:50] Nataraj: That's my personal view on like, , a lot of companies could have it if it is well run. Mm-hmm. . Um, and should have it because of this reason. Right? Mm-hmm. , it's sort of [00:02:00] like you are the innovation dilemma that you'll encounter at some point as a large company, and you have to have a sort of a backup backstopping mechanism to that innovation dilemma, which every company will eventually face. [00:02:12] Nataraj: Mm-hmm. , um, So I feel like the innovation, uh, accelerator or the incubator would sort of act as that, uh, you know, that part of small investment, it's sort of like an insurance to the, uh, to innovation dyna that you would eventually encounter anyways, uh, [00:02:28] Taylor: , I think you're right. [00:02:28] Taylor: There's a, there's an inherent problem there too, though, is that, um, uh, innovation is inherently a yo low yield. . Um, and so within, and it's my kind of rule of thumb, that within two or three years of any program like ours existence, um, finance is gonna come and say, where's the revenue? Where's the roi? And if you don't have a data driven way of showing your, your anticipated revenue, your anticipated ROI on the basis of your activities, then uh, [00:03:00] it's entirely legitimate that you get. [00:03:02] Taylor: There's a, there's a, there's data driven ways of showing that the whole venture ecosystem depends on the fact that you're able to show future revenue on the basis of what you're doing now. Uh, that's how you raise funds, right? Um, and so every, uh, innovation program inside an enterprise has to have that same data-driven hygiene. For full conversation check out Episode 53.