Christina Cacioppo is cofounder and CEO of Vanta, which is on a mission to secure the internet and protect consumer data. The trust management platform was valued at $2.5 billion in 2024 after a Series C investment led by Sequoia. Vanta went from $10M in annual recurring revenue in 2021 to $100M in 2024, while also giving us one of the best tech billboards of all time, “Compliance that doesn’t SOC 2 much.” Before founding Vanta in 2018, Christina was an investor at Union Square Ventures and helped bring Dropbox Paper to market as a product manager. We covered: Operating in a competitive market Fundraising frameworks Recruiting as you scale What should be AI-ified internally The inner game of being a founder --- Timestamps: (0:00) Intro (0:25) Staying under the radar (3:29) No referees in capitalism (5:20) Shipping velocity (6:43) Mindset on competition (8:09) Structuring a GTM approach (10:25) Fundraising strategies (16:36) VCs being “helpful” (21:57) Recruiting as you scale (28:33) Adapting to the AI era (32:09) What should be AI-ified (38:18) Mental game of being a founder --- More on Vanta and Christina: https://www.vanta.com/ https://x.com/christinacaci More on Alt Capital and Jack: https://www.altcap.com/ https://x.com/jaltma --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

Mamoon Hamid is a Partner at Kleiner Perkins. He has been an early investor in and served on the boards of some of the most innovative software companies of recent times including Slack, Figma, Rippling, Glean and Box. Prior to joining Kleiner Perkins, Mamoon was a Co-founder and General Partner at Social Capital. He started his venture career in 2005 at U.S. Venture Partners (USVP) where he eventually became Partner. Mamoon came to Silicon Valley in 1997 to join Xilinx, a Kleiner Perkins company, where he spent six years, initially as an engineer and later in product and marketing roles. We covered: Comparing innovation cycles AI’s $60 trillion opportunity The future of robotics Reigniting a storied firm Investing in Box, Slack, and Figma --- Timestamps: (0:00) Intro (0:29) The dot-com bubble (7:12) Web 2.0 and cloud (16:03) Early days of mobile (17:51) AI’s $60 trillion opportunity (21:48) Where to invest in AI (28:39) The future of robotics (32:35) Reigniting a storied firm (41:36) Growing vs recruiting talent (46:42) Win rate aspirations (49:16) Investing in Box, Slack, and Figma (54:36) Assessing founders (57:14) Kleiner Perkins’ strategy (1:00:52) Family and faith --- More on Kleiner Perkins and Mamoon: https://www.kleinerperkins.com/ https://x.com/mamoonha More on Alt Capital and Jack: https://www.altcap.com/ https://x.com/jaltma --- https://linktr.ee/uncappedpod Email: friends@uncappedpod.com

Vinod Khosla is an entrepreneur, investor and technologist. In 2004, Vinod formed Khosla Ventures to focus on both for-profit and social impact investments that have included OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. After graduating college, Vinod co-founded Daisy Systems, the first significant computer-aided design system for electrical engineers, which led to an IPO. He later went on to co-found Sun Microsystems in 1982, serving as its first chairman and CEO. After joining Kleiner Perkins Caulfield and Byers (KPCB), Vinod intubated the idea for Juniper Networks to take on Cisco System’s dominance of the router market, a company that would give KPCB a 2,500x return on its early investment. Vinod is driven by the belief that technology is a positive force multiplier to accelerate societal reinvention in food, health, climate, energy transportation, education, housing finance, media, retail and entertainment for billions around the globe. His greatest passion lies in being a mentor to entrepreneurs who are building companies to tackle society’s largest challenges. We covered: Uncanny ability to predict the future AI generating a new era of abundance Future of energy, transportation and medicine Increasing the consequence of success Khosla’s approach to venture Instigating change --- Timestamps: (0:00) Intro (0:26) Craziness of the current cycle (5:54) Predictions of the future (9:35) Role of humans with AI (16:20) Potential AI dystopia (23:18) Investing in OpenAI (33:21) Robotics being next (39:53) Incumbents not innovating (42:29) Mindset around risk (44:14) Bull case for energy (50:22) New transportation (54:18) Future of medicine (1:03:00) A different type of enjoyment (1:05:40) Approaches to venture (1:12:13) Khosla’s operating principles (1:16:17) Staying energized --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

It was a pleasure to sit down with Dan Feder, Senior Managing Director with the University of Michigan Investment Office who leads the endowment’s investments in venture capital and private equity. Prior to joining the University of Michigan, Dan was the Managing Director of Private Markets at the Washington University Investment Management Company. Dan’s career in endowment management began at the Princeton University Investment Company where he led the development of Princeton’s global private equity and venture capital portfolio. Dan has also served as the Managing Director of Private Markets for the Sequoia Capital Heritage Fund (an endowment-style investment fund sponsored by Sequoia Capital) and as a Senior Investment Manager in the endowment services area at TIAA-CREF. We covered: Endowment portfolio construction Incentive structures in LP land Backing conflicting strategies UMich’s framework to investing Picking individuals vs firms --- Timestamps: (0:00) Intro (0:40) Becoming an endowment manager (2:59) Constructing an endowment’s portfolio (9:10) Risk-based investing vs uncertainty (13:07) Incentive structures in LP land (16:28) Team construction (22:26) Backing strategies that are at odds (26:06) Why LPs invest in venture (27:38) UMich framework to investing (32:29) Picking individuals vs firms (36:40) Big vs small funds (40:48) How to pick fund managers (45:41) Herd mentality in LP land --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

This was a fun one! Sam is my brother and the CEO of a small company in SF called OpenAI. I’m glad he was able to take time out of his busy schedule to give me a hard time and share his thoughts on the future of AI. We covered: AI discovering new science The risk of superintelligence What’s after reasoning Humans needing humans The latest with OpenAI Meta / Scale AI news Plenty of brotherly banter --- Timestamps: (0:00) Intro (0:48) AI discovering new science (5:40) Humanoids are the future (8:27) A world with superintelligence (11:20) Medium-term predictions (15:37) Potential OpenAI apparatus (19:01) Supply chain implications (21:51) Meta / Scale AI news (29:04) Personal reflections --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

Marc Andreessen is a cofounder and general partner at the venture capital firm Andreessen Horowitz, a venture capital firm that manages $45 billion in assets under management. He is an innovator and creator, one of the few to pioneer a software category used by more than a billion people and one of the few to establish multiple billion-dollar companies. Marc co-created the highly influential Mosaic internet browser and co-founded Netscape, which later sold to AOL for $4.2 billion. He also co-founded Loudcloud, which as Opsware, sold to Hewlett-Packard for $1.6 billion. He later served on the board of Hewlett-Packard from 2008 to 2018. Marc serves on the board of the following Andreessen Horowitz portfolio companies: Applied Intuition, Carta, Coinbase, Dialpad, Flow, Golden, Honor, OpenGov, Samsara, Simple Things, and TipTop Labs. He is also on the board of Meta. We covered: Evolution of the venture playbook Small vs large funds Current AI landscape Politics and Silicon Valley Tech and the media A few highlights: Optimizing for the maximum amount of power Conflicts being the reason a16z isn’t even larger The middle is dead; you’re either Gucci or Walmart Only 8 companies in the S&P 500 are innovating We’ve lived in an era of intense preference falsification AI and machines making the ultimate decision --- Timestamps: (0:00) Intro (0:27) Evolution of the venture playbook (15:54) Small vs large funds (29:10) Becoming a top tier firm (35:33) Limiting factors to building big companies (40:11) Investing in AI (50:02) Developing investors (59:06) AI going wrong (1:09:20) Politics and Silicon Valley (1:11:39) Tech and the media (1:23:22) Preference falsification (1:31:10) Career advice  (1:34:07) Huberman “beef” (1:38:21) Question from X --- More on Marc: https://x.com/pmarca https://pmarca.substack.com/ https://a16z.simplecast.com/ More on Uncapped https://linktr.ee/uncappedpod https://x.com/jaltma --- Email: friends@uncappedpod.com

Jordan Bramble is the CEO of Antares, a nuclear energy company that has raised over $50M to become America’s industrial base partner for special-purpose microreactors. Antares focuses on high-value use cases in power-constrained environments that wouldn’t be possible without nuclear power. They are developing resilient fission-based power systems for critical assets for the Department of Defense on earth and in space. Unlike grid-scale reactors, these use cases primarily favor kilowatt-scale systems. This focus on non-commodity energy applications with smaller scale reactors will enable Antares to develop its first deployments on faster timelines with less research and development and capitalization risk. Antares also partners with commercial companies in extractive industries, edge computing, and space power, in turn bringing the benefits of commercial scale back to the DOD. We covered: History of nuclear Demand for nuclear Small modular reactors Government collaboration Building in hard tech Scaling nuclear reactors A few highlights: First nuclear reactor built under UChicago’s football field A nuclear powered airplane that could fly indefinitely Net zero not being possible without nuclear Powering the AI demand for data centers The Golden Dome and lasers in space Working back from the mission effect Interdisciplinary problems attracting talent --- Timestamps: (0:00) Intro (0:22) History of nuclear (6:50) Radical decline in development  (10:51) Current appetite for funding (20:53) Small modular reactors (30:11) Selling to defense (34:30) LA becoming a hard tech hub (37:13) Fostering a culture in hard tech (43:42) How to scale nuclear reactors --- More on Antares: https://antaresindustries.com/ https://x.com/jordanbramble More on Uncapped: https://linktr.ee/uncappedpod https://x.com/jaltma --- Email: friends@uncappedpod.com

This week I enjoyed riffing with David Tisch, Managing Partner of BoxGroup. BoxGroup is an NYC-based seed stage venture capital firm that has invested in over 500 seed-stage startups over the last 15 years, including Plaid, Ro, Ramp, Clay, Scopely, Warp, Cursor, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David is the Chairman of GoodDog, a marketplace to find pets online. He is the co-founder of TechStars NYC and serves on the board of Friends of Hudson River Park. We covered: Scaling something deemed unscalable Art of being collaborative Taste not being teachable VC help being overrated Building a NYC brand --- Timestamps: (0:00) Intro (0:27) Scaling a collaborative fund (8:23) Stack ranking portfolios (11:29) Investing at seed (17:29) Hiring for taste (22:30) The art of being collaborative (29:03) VC help is overrated (41:38) Why VCs pass on companies (48:11) Building a brand in NYC (55:02) North Stars in early-stage investing --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

I had a blast sitting down with Qasar Younis, Co-Founder and CEO of Applied Intuition, a company that’s on a mission to accelerate the world’s adoption of safe and intelligent machines. The company builds software that makes it faster, safer, and easier to bring autonomous systems to market. Last valued at $6B, Applied Intuition has raised a total of $602M since its inception in 2017 and plays a critical role in both the commercial and defense sectors.  Previously, Qasar was a Partner and COO of Y Combinator, the renowned startup accelerator that has invested in companies like Airbnb, Coinbase, Cruise, DoorDash, Stripe, among others. Prior to Y Combinator, Qasar founded a technology firm, which was later acquired by Google, and worked as an automotive engineer at General Motors and Bosch. Younis has a bachelor’s degree in mechanical engineering from Kettering University (formerly known as General Motors Institute) and an MBA from Harvard Business School. We covered: Radical pragmatism Roots of the automotive industry Complexities of being dual use Fostering an intrinsically contrarian culture Evolving with your work --- Timestamps: (0:00) Intro (0:31) Psychology of starting a company (17:04) Love for the automotive industry (22:54) Autonomous vehicle landscape (25:45) Deep partnership with customers (28:49) Complexities of being dual use (34:44) Culture being intrinsically contrarian (40:01) Gen AI and humanoid robotics (42:28) More noise than signal in investing (44:14) Evolving with your work (47:43) Companies working is a state in time  --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

It was a pleasure to sit down this week with Josh Kopelman, one of the original architects of seed stage investing who continues to re-invent what it means to operate within venture. Josh co-founded First Round Capital, which has invested at the earliest stages in companies like Square, Uber, and Roblox. Some of Josh’s more recent investments include Notion, Pomelo Care, Loyal, and Perpay. Since First Round’s inception in 2004, Josh has invested in 500+ startups and has frequently made the Forbes “Midas List” which ranks the top 100 tech investors. Josh has been a founder three times (four if you include founding First Round). In 1992, while in college, he co-founded Infonautics Corporation – and took it public on NASDAQ in 1996. Josh co-founded Half.com in 1999 and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in 2000, where Josh remained for three years. In late 2003, Josh helped to found TurnTide, an anti-spam company that created the world’s first anti-spam router. TurnTide was acquired by Symantec just six months later. We covered: His “Venture Arrogance Score” The role of relevance in venture Making money in disequilibrium Overlooking margin superiority Decision-making as a product --- Timestamps: (0:00) Intro (0:25) Current landscape (4:39) Venture Arrogance Score (10:49) Comparing fund models (14:24) The role of relevance in venture (21:03) Small funds vs large funds (26:36) Making money in disequilibrium (33:57) Overlooking margin superiority (43:17) First Round’s strategy (49:02) Operating like a company (56:49) Future of First Round --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

This week I sat down with Garry Tan, President & CEO of Y Combinator. YC has funded 5,000+ startups including Airbnb, Stripe, DoorDash, Rippling, and Reddit, among others that have totaled $600B in combined valuation. Garry is a designer, engineer, and investor in early stage startups. Previously Founder & Managing Partner of Initialized Capital, an early stage venture capital fund that was earliest in Coinbase and Instacart. Before that, Garry was a partner at Y Combinator where he invested in and directly worked with over 700 companies at the earliest stage. He previously co-founded Posterous and helped build it to a world-class website used by millions (acquired by Twitter). Garry is a builder at heart. We covered: Running YC like a founder Advice for founders Picking winners What changes because of AI YC being the “YC of hard tech” Public service --- Timestamps: (0:00) Intro (0:25) Running YC like a founder (6:25) Focusing on growth and prosperity (12:40) Incredible pick rate (14:34) Role of the Group Partner (19:21) Lean vs fat startups (20:53) Archetypes of special founders (25:18) Rule changes because of AI (33:00) YC being the “YC of hard tech” (37:40) Community and political involvement --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

It’s always a pleasure to jam with Elad Gil, a serial entrepreneur and a startup investor. As an early leader at Google, Elad helped build the initial mobile team, before founding MixerLabs, which was acquired by Twitter. Later, he co-founded Color Health, a genetic testing company specializing in cancer detection. Over the past decade, he's backed nearly 40+ companies valued north of $1B each, including Airbnb, Coinbase, Figma, Instacart, and Stripe. He's also invested in Harvey, Mistral, Perplexity, Pika, and other leading AI startups. Elad is also author of the High Growth Handbook and is excited to be working on his next book focused on how to scale during the zero to one phase of a startup’s journey.  We covered: Optimizing for market need and optionality Recipes for long career arcs Getting more leverage on time Investing outside of AI Value in getting the theme right --- Timestamps: (0:00) Intro (0:50) Shamelessness mindset (4:16) Optimizing for market need (5:55) Cultivating optionality (8:29) Characteristics of people with long career arcs (9:54) What to optimize for early in a career (22:20) Different phases of your life (25:20) Aspiring to do things that are useful (26:33) Pivot points in careers (31:16) Becoming great investors (33:28) Getting more leverage on time (36:57) Investing outside of AI (40:58) Getting the theme right means more (47:01) Elad’s new book --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

I was pumped to chat this week with Sarah Guo. Sarah is a startup investor and the founder of Conviction, an investment firm purpose-built to serve intelligent software, or "Software 3.0" companies. Some of her investments include Harvey, Mistral AI, Sierra, Cognition, HeyGen, and Cartesia, among others. Prior to 2022, she spent nearly a decade incubating and investing as a General Partner at Greylock Partners. Sarah co-hosts a podcast with Elad Gil called No Priors where they discuss the AI revolution. We covered:  Compounding qualities of enduring firms Brand building in the current market Taking risk by having an opinion Learnings from her time at Greylock AI discourse compared to previous cycles --- Timestamps: (0:00) Intro (0:11) What a VC firm is at its core (2:27) Compounding qualities of enduring firms (6:44) Intentionality behind building Conviction’s brand (13:01) Correlation or causation between brands and returns (16:33) Shape of the current VC market (27:15) Learnings from experience at Greylock (32:06) Market vs founder driven (33:55) AI conversation shifting from inputs to outputs (36:28) More billion dollar companies than ever before (42:44) Agency being the last human resource (44:40) Important skills for kids to learn --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

Adam Guild is the CEO of Owner, a business he started when he was only 17. It now has tens of millions of revenue, hundreds of employees, and thousands of customers. I’ve had the pleasure of working on his board for a few years now, and he is one of the most impressive people I’ve ever gotten to know. Working with him was a big part of what made me realize I want to do venture for the rest of my career. He tracks his nutrition, exercise, time, and sleep to an extreme degree so he can show up to work every day as strong as possible. He goes to extreme lengths to recruit the best talent. He is equal parts hungry to learn from everyone around him, but courageous in making his own unconventional decisions. I think he’s one of the most under-known founders right now, but I think that will soon change.  Hope you enjoy watching this. --- Timestamps: (0:00) Intro (0:07) Inside the mind of a young founder (6:36) Boldly purchasing Owner’s domain (9:34) Listening to others vs being instinctual (14:12) Decision making as a CEO (16:43) Fostering a culture while scaling (18:34) High impact interview questions (21:29) Recruiting the best talent (29:50) Never missing an investor update (34:16) Getting canceled on Twitter (42:41) Startups are the Olympics of business --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

This week I sat down with Aaron Levie, Co-Founder and CEO of Box. Aaron came up with the idea behind the cloud computing company as a 19 year old college student and has led the company since its inception in 2005. Today, Box does over $1B in revenue with a market cap of $4.4B, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Meritech Capital. --- Timestamps: (0:00) Intro (0:10) Excitement in AI (6:50) Startups vs incumbents (15:04) Pricing agents (17:42) AI over or under hyped (19:17) Being first to cloud (24:55) Staying motivated (28:29) Shifting political landscape --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

This week I enjoyed speaking quickly with Keith Rabois, a Managing Director at Khosla Ventures and the CEO of OpenStore. At Khosla, Keith led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. While a General Partner at Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and before that made early personal investments in YouTube, Airbnb, Palantir, Lyft, Udemy, and Eventbrite. Keith started his career in leadership roles at PayPal and LinkedIn before becoming COO of Square. --- We covered: (0:00) Competing where there isn’t competition (2:29) Traits of top decile founders (7:16) Picking people (9:57) Being a consigliere (13:54) Decision making (21:51) Acting when confident (26:43) Advantages of a large fund (31:06) Raising in a frothy market (35:47) Tech and the government (43:21) Being vocal on politics (46:47) Valuing board members (52:24) Former operators vs career investors --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

This week I spoke with Shaun Maguire, a Partner at Sequoia Capital. He led their investments into SpaceX, The Boring Co, and X among others. Prior to Sequoia Shaun co-founded a cybersecurity company which was acquired for $1B and worked at DARPA. I could have happily spoken with Shaun for four hours. --- We covered: (0:00) Speaking his mind in public (13:38) Trust and the media (24:27) Tech’s political flip (29:27) Investing in hard tech vs. software (45:27) Thinking with a beginner's mind (52:30) Fulfillment in investing (59:33) Investing in outlier people --- Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com