"Lessons from a Startup Life"

Carta, originally known as eShares, was founded in 2012 by entrepreneur Henry Ward and serial investor Manu Kumar. Henry Ward assumed the role of CEO, while Manu Kumar became the company's Chairman. The company was founded on the idea that venture-backed firms needed a way to digitally manage equity, issue securities, and maintain accurate cap tables. Carta, headquartered in San Francisco, is renowned for its role as the industry's largest provider of SaaS software that manages cap tables and valuations, offering significant benefits to startup CEOs, CFOs, and board members. Its services include the digitization of paper stock certificates, stock options, warrants, and derivatives, enabling efficient equity management and ownership tracking for companies, investors, and employees. Furthermore, Carta operates Carta Liquidity Solutions (originally called CartaX) a private stock exchange. Peter Walker runs the insights team at Carta, focused on discovering key narratives across the private market ecosystem. Prior to Carta, he was the Head of Marketing for the media analytics company PublicRelay. He also led the data visualization team at the Covid Tracking Project at The Atlantic Magazine during the peak of the pandemic. In a recent podcast discussion with Peter, the conversation revolved around the transformative role of data science in understanding the dynamics of startups, later-stage companies, VCs and PE firms, and strategic investors. He shed light on the valuable insights he has gleaned through data analysis, offering a deeper understanding of the intricate relationships and challenges within the entrepreneurial ecosystem. His expertise provided crucial takeaways on how startups can navigate the complexities of equity management, capital allocation, and investor engagement. By leveraging data science, Walker has uncovered trends and patterns that not only enhance Carta's offerings but also empower companies and investors to make informed decisions, ultimately contributing to the growth and success of the broader startup landscape. I strongly recommend listening to this podcast for a deep dive into the world of startup finance and ownership and other the invaluable insights that Peter Walker of Carta has to offer. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

With extensive experience across entrepreneurship, operations, advising, and investing, Ron Levin (not related to this blogger and podcaster) brings invaluable insight to examining venture capital trends. As Managing Partner of Alumni Ventures' prolific Seed Fund, he oversees one of the most active VC funds in the US. Ron co-founded TravelPerk, a travel management platform now valued over $1 billion with thousands of global employees and customers. He also led Booking.com's B2B division, advised multiple startups, and invested in numerous high-growth companies after starting his career at McKinsey. This diverse background spanning founding, operating, and funding startups gives Ron a multifaceted perspective on the VC landscape. His proven success across roles offers credibility regarding how investors can drive impact alongside financial returns. Ron’s just published book entitled "Higher Purpose Venture Capital" explores how VC can drive both growth companies and social impact when backing purpose-driven founders. In this book, Ron emphasizes that entrepreneurs and investors play a crucial role in advancing solutions to societal challenges like "poverty and inequality." The book profiles fifty ventures showing how VC can enable innovation that generates returns and makes a difference. Ron advocates for "socially-conscious entrepreneurship", arguing profit and purpose can go hand-in-hand. He provides guidance to make "purpose-driven profits" a reality, supporting individuals interested in driving change. The book inspires a vision of VC as a “force for good” while delivering practical insights. While the mission of VC firms is to back world-changing companies, investors should also evaluate social impact alongside financials and a compelling mission in order to attract top talent. Ron demonstrates that ambitious founders tackling pressing problems represent promising investment opportunities. With responsible stewardship, VC can transform lives while producing competitive returns. Ron offers an insightful perspective on aligning VC with social responsibility. "Higher Purpose Venture Capital" makes the case for VC's unique role in scaling solutions and provides a valuable playbook for purpose-driven profits. It highlights the tremendous good possible when investors fund innovation that changes people's lives for the better. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Francesca Lazzeri is an accomplished scientist who works with machine learning, artificial intelligence, and applied econometrics. Today she works at Microsoft as Director of AI and Data Science where she leads 8 teams of 50 data scientists and machine learning scientists to develop a portfolio of machine learning and AI services that serves other internal teams. She also teaches "Introduction to Artificial Intelligence with Python" at Columbia University. Before joining Microsoft, she was a research fellow at Harvard University in the Technology and Operations Management Unit. We covered a wide range of topics related to artificial intelligence, data science, and emerging technologies. We discussed how AI, econometrics, and data are intersecting in new ways to drive insights and innovation. The evolution of data science and data scientist roles was examined, along with techniques for quantifying phenomena like hallucinations. For enterprises, we talked about best practices for responsibly leveraging AI while avoiding pitfalls like hallucinated content from large language models. Throughout the podcast, we touched on the distinction between concepts like machine learning, neural networks, generative learning, and more. Other applications like image generation were covered, along with methods for validating AI model outputs. Overall, it was a thought-provoking look at how AI and data analytics are rapidly evolving and being applied across industries. Overall, the podcast was a captivating exploration of how AI and data science are shaping industries and transforming businesses. Francesca's contributions and expertise have undoubtedly inspired many, and her work continues to drive advancements in AI. As the world continues to embrace the potential of AI and data-driven technologies, Francesca's influence will undoubtedly remain a guiding light for AI researchers, data scientists, and innovators. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

This episode of "Lessons from Startup Life" podcast features Jeffrey Rayport, Senior Lecturer of Business Administration at the Harvard Business School. Jeffrey specializes in teaching and researching growth-stage technology ventures and their scalability. Prior to HBS, Rayport was as an operating partner at Castanea Partners, a private equity firm specializing in retail and consumer brands. He was founder and CEO of Marketspace LLC, a digital advisory firm, and co-founder of Monitor Executive Development, a custom executive education business. He was a Senior Partner at Monitor Deloitte. Rayport was also a co-founder of several corporate universities, including at Omnicom Group, Bertelsmann AG, and Amgen. Jeffrey makes some really compelling points about the extrapolation phase of startups, and the importance of having product market fit (PMF). He sees PMF as a process that is not a “singular existential event” in the life of a startup but more so a process that must be repeated, especially when new versions and products are introduced. PMF is distinctly different from “profit market fit” – an overlooked but critical distinction and stage – which many companies “grow their way into” and therefore play down. One outstanding observation that Jeffrey makes is the “whiplash” effect many startup founders and CEOs have experienced recently as they shifted from growth-at-all-costs to path-to-profitability, or perish. I especially liked his point about organizations which are able to manage strategic experimentation and disciplined execution simultaneously. This is a critical skill for startups, as they need to be able to adapt quickly to changing market conditions while also perfecting their business model. I also found his discussion of the reasons why some startups fail to scale to be very informative. These are all common challenges that startups face, and it's important to be aware of them so that you can take steps to mitigate them. Jeffrey shares with us the most scaling strategies for successful exits. He also explains how a company can achieve diversity, equity, and inclusion (DEI) while scaling. Finally, we discuss how B2B and B2C startups should improve their all-important service interface with customers in order to grow and scale. Overall, I thought this was an excellent discussion because it was very insightful – diving deep into concepts in startup life which have had surface explorations. I would recommend this podcast to anyone who is interested in learning more about the challenges and opportunities of establishing, growing and scaling a startup. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Note: Here’s a brief recap of a recent discussion I had with noted VC, Eric Paley. He and the other partners at Founder Collective pursue a “First Check-in” approach to investments that’ll be interesting and perhaps valuable to listeners. The “Lessons from a Startup Life” Podcast is available on Amazon Music, Apple Podcasts, Deezer, Spotify, Turn-In + Alexa and other leading podcast streaming services. Eric is a general partner at Founder Collective, a seed-stage VC firm. He led Founder Collective's seed investments in several successful startups, including Uber (NYSE: UBER), The TradeDesk (Nasdaq: TTD), Airtable, Whoop, Cruise Automation, HotelTonight, Formlabs, and Omada Health. Previously, Eric was twice an operator before becoming a VC. He co-founded Brontes Technologies – a 3D imaging company spun out of MIT – which was acquired by 3M. At Founder Collective, the firm’s overall approach is to be the ‘first check-in’ prior to or in Series A. Eric describes it as a “software driven” fund and sees AI as the next step of software eating the world. In terms of investment decisions, they are of course underpinned by a solid understanding the business. Ultimately, investment decisions are heavily influenced by the partners’ assessments of their prospective portfolio companies’ founder or founders. It’s an interesting, purposely “person driven” decision process. During the course of the podcast Eric observed: Eric divides his days between: Tune-in and hear more. Enjoy! If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

In this episode, we dive into Artificial Intelligence (AI) investing with Rudina Seseri, founder and managing partner of Glasswing Ventures. Rudina’s career started twenty years ago as an investment banker in the technology group at Credit Suisse. In that role she was responsible for multibillion-dollar acquisitions. Her acquisition work continued in the corporate development office at Microsoft. She has served four years as Entrepreneur-In-Residence at Harvard Business School where she was recently appointed as an Executive Fellow and was recently named to the Board of Directors of the New England Venture Capital Association (NVCA). Highlights from this Episode Steve Jobs once said, “Overnight success stories take a long time.” While it may seem like the hype around AI emerged overnight, according to Rudina it has really been more than a decade in the making. That’s how long she has been investing in AI technology. Having that perspective is essential at a moment like the one we are living through right now. For example, on their most recent earnings calls, Alphabet, Amazon, Apple, Meta, and Microsoft mentioned “AI” 5X more than they did a year ago. Hype cycles always bring with them tremendous hope and optimism about the future. They also make it difficult for investors to discern hype from reality. Rudina’s advice for entrepreneurs, executives, and investors is to recognize the essential role the underlying technologies play in driving advancement, enterprise adoption, and opportunities for innovation. This is crucial. She sees a major wave of investment opportunities across the AI landscape, from industry-specific applications to advancements in machine learning frameworks, hardware, semiconductors, and more. In her view, the application layer represents the best opportunities for investors and builders in generative AI. Rudina also believes the investment and innovation to come are likely to mitigate job losses, one of the major concerns about AI. Other issues will be harder to solve, like ensuring that AI algos are free from bias. AI applications are only as good as their data, so it is critical to ensure that humans remain in the testing loop. Rudina sees data governance and compliance as major issues right now. That’s because the technology is far ahead of the regulations, which has enterprises looking to governments for direction. They’re going to get it. For investors, that will be important to watch. This is an exciting time for investors in AI. Look no further than Nvidia crossing $400/ share and $1B in market cap this morning. This is a timely conversation. I hope you enjoy it as much as I did. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Chris Miller is the author of Chip War: The Fight for the World's Most Critical Technology — essential reading for anyone in the tech industry. Episode Summary and Chris’ Bio Chris serves as Associate Professor of International History at the Fletcher School at Tufts University, where his research focuses on technology, geopolitics, economics, international affairs, and Russia. He received his PhD and MA from Yale University and his BA in history from Harvard University. For more information about Professor Miller, see www.christophermiller.net. In Chip War, Chris explains how the semiconductor came to play a critical role in military, consumer and business technology and how the US became dominant in chip design, manufacturing and in various markets. He also details how the US lost its leadership position, lost it in some arena, and regained it and the new market challenges. Background In the 1980s, semiconductors were the equivalent of crude oil in terms of their importance because of the growing significance of semiconductor technology in various industries and the US’ market control. In the period that followed the advent of the PC and Macintosh, the US lost its leadership in microchips. Japan, Taiwan and other countries had caught up and challenged the U.S.'s dominant position in the global technology landscape. Over the past 50-60 years, U.S. trade policy can be characterized by a variety of approaches and strategies. The United States has pursued policies aimed at protecting domestic industries, promoting free trade, and negotiating trade agreements with other countries. The specifics of U.S. trade policy have evolved over time, reflecting changing economic and geopolitical circumstances. In the chip industry, companies place significant importance on their intellectual property (IP) portfolios. Having a strong IP portfolio allows companies to protect their innovations and technologies from unauthorized use or competition. Additionally, companies in the chip industry often adopt a patent defensive approach, using patents as a means to defend against potential legal challenges or infringement claims. The future of 5G technology holds great potential. 5G networks are expected to revolutionize communication by offering faster speeds, lower latency, and increased capacity. This technology is anticipated to enable advancements in various sectors, including autonomous vehicles, Internet of Things (IoT), augmented reality (AR), and more. China has emerged as a major player in the global technology market. Companies like Huawei and Foxconn have gained prominence for their manufacturing capabilities and innovations. Huawei, in particular, has made significant strides in the telecommunications industry and has become a major player in the development and implementation of 5G technology. Overall, these topics touch upon the evolving landscape of technology, trade policies, and the role of key players in the chip industry, such as China and the United States. If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Rob May is the CEO and Founder of Nova Cloud. That makes him a four-time entrepreneur. He’s also made angel and VC investments in over 100 startups. He’s worked in the past as an electrical engineer designing various hardware devices. As an industry analyst, Rob writes the newsletter “Investing In AI” and hosts the “AI Innovator's Podcast”. Rob May is the co-founder of the AI Operators Fund along with Rana el Kaliouby. Rob tries to be the first check in. He likes to take "syndicate risk" -- there is a risk waiting for the deal to close and a VC invests and takes out good deals. Valuations have come down and they are getting into really good deals. His reading of this moment: ChatGPT will unlock new businesses and vertically targeted startups. LLMs get better as they get bigger. Scaling is different and it has emergent properties. SaaS early stage investments take $4-5m; AI deals need $6-8m. There are other differences. But this space will have heavy over-investment. AI companies: There's a lot of defendability. Data is the moat. Beyond product market fit, today there's "model market fit". We discussed "The ChatGPT Stampede" and many other interesting topics. Recommended reading: Investing in AI (Rob's blog) Subscribe now Leave a comment Share If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

ABOUT THIS EPISODE In this episode, we take a deep dive into the subject of CEO leadership with Scott Keller, a partner in McKinsey & Company’s LA office. We discuss Scott’s latest book: CEO Excellence: The Six Mindsets That Distinguish the Best Leaders from the Rest. We delve into what sets the best CEOs apart; CEO excellence and their mindset; the importance of a “enterprise leader” attitude, great board members, micromanaging as a CEO, and the humble CEO among other topics. ABOUT SCOTT Scott Keller, a senior partner in McKinsey’s Southern California office, is a coauthor of CEO Excellence: The Six Mindsets That Distinguish the Best Leaders from the Rest. Available on Amazon. (Here) He is the New York Times Bestselling Author of seven books. He is also a heavy-metal guitarist and songwriter who has recorded original music with members of Whitesnake, Testament, and Stone Sour. For more background about Scott check out his LinkedIn profile: https://www.linkedin.com/in/keller-scott/ If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

"Why Start-ups Fail" is requiring reading for entrepreneurs. Professor Thomas Eisenmann, the author of this seminal book, chats about systemic macroeconomic problems for startups; finding sounding boards; first jobs after business school; keys to scaling companies; the state of business school education, and other topics. Professor Eisenmann talks about the requisite combination of a basic education, simulation of the startup environment in B-school, genetic predisposition and the right psychological profile for entrepreneurship. He also provides a sneak peak into the next book he is writing. Tom Eisenmann is the Howard H. Stevenson Professor of Business Administration at the Harvard Business School, Peter O. Crisp Chair at the Harvard Innovation Labs (aka the “iLabs”), and Faculty Co-Chair of the HBS Rock Center for Entrepreneurship, the Harvard MS/MBA Program, and the Harvard College Technology Fellows Program. He is the author of the bestselling book Why Startups Fail, teaches the MS/MBA core courses Technology Venture Immersion and Designing Technology Ventures. In recent years, he has chaired HBS’ MBA Elective Curriculum (the 2nd year of the MBA Program) and launched or headed courses including The Entrepreneurial Manager, Making Markets, Entrepreneurial Sales & Marketing, Product Management 101, the January Term Startup Bootcamp for first-year MBAs and the MBA electives Entrepreneurial Failure, Launching Technology Ventures and Managing Networked Business. RECOMMENDATIONS Why Startups FailWhy Start-ups Fail If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: Lessons from a Startup Life Timely insights and practical advice for anyone working on a startup, from investors to executives and anyone in-between. This blog draws on the writer's decades of experience and provides a rare insider's perspective on the process. By Doug Levin If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Scott Kirsner explains how he views journalism today, the impact and use of ChatGPT, innovation and the state of the Boston tech ecosystem and his hot takes on other topics. Some of the questions posed and topics discussed include: Scott’s latest book is “Innovation Economy: True Stories of Start-Ups, Flame-Outs, and Inventing the Future in New England”. It’s available on Amazon. (Here) ABOUT SCOTT Today, Scott is running InnoLead – a network of people working on innovation and R&D in established companies. (Members include companies like USAA, Johnson & Johnson, Bose, Shell, 3M, and Netflix.) Scott writes the Innovation Economy column on Mondays in the Boston Globe. He was a member of the team that launched Boston.com in 1995. He has been writing a column for the Globe since 2000. His work has also appeared in Wired, Fast Company, The New York Times, BusinessWeek, Newsweek, and Variety. He has also authored several books, including “Inventing the Movies,” about the technological history of the movie industry, and “Innovation Economy,” a collection of his best Boston Globe columns about the New England startup ecosystem. He was the editor of “The Convergence Guide: Life Sciences in New England” and was a contributor to “The Good City: Writers Explore 21st Century Boston.” Scott also helps organize Nantucket Conference and Future Forward He tweets often as @ScottKirsner For more background about Scott: https://www.bostonglobe.com/about/staff-list/correspondent/scott-kirsner/ If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/

Marily has many strong beliefs regarding product management today and its evolution. For example, she thinks that one day all PMs will be “AI PMs”. Marily offers advice on when to hire a PM in your startup. She believes that ChatGPT is not an extinction event for PMs but more of a new technology that represents an evolutionary change. She thinks product management will be enhanced by ChatGPT and Generative AI. There are many more questions that Marily addresses in this podcast. Today, Marily is the Product Lead for Avatars & Identity at Meta. She’s an Executive Fellow at Harvard Business School. Marily teaches one of the most popular courses on Maven: Building AI Products - For Current & Aspiring Product Managers. Prior to Meta, she spent 8 years at Google as a product manager, working on Google Glass, machine learning around speech recognition. She is a three-time TEDx speaker. Marily earned a PhD in Computing Science and her Masters from Imperial College London. She is degreed from Stanford’s Graduate School of Business and ETH Zurich. Marily's Substack can be found here: http://marily.substack.com Please listen and enjoy! If you liked this podcast, prior Lessons from a Startup Life blog posts are available here: https://douglevin.substack.com/