Ron Conway is the Founder and a Managing Partner of SV Angel. He has been an active angel investor since the mid-90s and has received wide recognition for his role in the tech ecosystem. He has been included on Vanity Fair’s 100 most influential people in the Information Age, awarded Best Angel at the TechCrunch Crunchies Awards, and has been named on Forbes Magazine's Midas list of top “deal-makers” since 2011. Prior to founding SV Angel, Ron was with National Semiconductor Corporation in marketing positions (1973-1979), Altos Computer Systems as a co-founder, President, and CEO (1979-1990), taking the company public on Nasdaq in 1982.

Ron reflects on decades of investing, from semiconductors to AI, and what it really means to be an “all in” partner to founders. He shares how relationships compound into an unfair advantage, why the best investors show up at inflection points, and how being willing to fight, whether in boardrooms or Washington, can change outcomes.

---

Timestamps:

(0:00) Intro

(1:50) From semiconductors to AI

(8:39) Two investments that changed everything

(11:46) Nonpassive angel investing

(14:57) Becoming a relationship broker

(18:00) Building authentic relationships

(24:48) Going deep with OpenAI and Airbnb

(29:19) Fighting for founders

(31:39) Remarkable returns at seed

(33:20) The state wealth tax

(37:17) Tech and politics

---

Links:

https://x.com/RonConway

https://x.com/jaltma

https://svangel.com/

https://uncappedpod.com/

---

[email protected]

At 23, with no legal background, Max Junestrand co-founded Legora to transform how lawyers work.

Legora recently (March 2026) raised $550 million at a $5.55 billion valuation in a Series D funding round to accelerate its expansion across the United States. Over the past year, Legora has grown from 40 to 400 team members across the globe and the platform supports tens of thousands of lawyers each day across 800 customers in more than 50 markets.

Max shares the story of building Legora, what it really means to build AI-native software from day one, why legal work is uniquely suited for AI, and how a small team from Stockholm convinced some of the world’s largest law firms to change how they work.

---

Timestamps:

(0:00) Intro

(0:31) Legora's origin story

(9:05) Building an AI-native company

(18:16) No sacred cows, the models will be amazing

(27:36) Winning pilots and global expansion

(36:43) Starting in Europe

(47:15) Stockholm culture and "blodsmak"

---

Links:

https://x.com/MaxJunestrand

https://x.com/chetanp

https://x.com/jaltma

https://legora.com/

---

https://uncappedpod.com/

[email protected]

In this episode, the team behind Y Combinator reflects on what has — and hasn’t — changed since the early days of YC, and how AI is reshaping what it means to be a founder. They discuss how they evaluate builders now, why execution still matters more than competition, and what YC is prioritizing as the startup landscape evolves. At its core, the mission remains the same: increase the number of great startups in the world.

Garry Tan is president and CEO of Y Combinator and a group partner. He was a partner at Y Combinator from 2011 to 2015, where he built key parts of the YC experience for founders including Bookface and the Demo Day website. Garry is the co-founder of Initialized Capital and Posterous (YC S08), a blog platform acquired by Twitter, and prior to that, he was an early designer and engineering manager at Palantir.

Harj Taggar is a Managing Partner at YC. Of the 1,000+ companies Harj has advised while at YC, 5 have gone public. He was previously founder and CEO of Triplebyte (YC S15) and Auctomatic (YC W07), which was acquired by Live Current Media in 2008. He first joined YC as a partner in 2010, leaving in 2014 to start Triplebyte and rejoining in 2020.

Jared Friedman is a Managing Partner at YC. Jared has advised more than 20 YC unicorns while at YC. He was co-founder of Scribd, which was funded by Y Combinator in 2006 and grew to be one of the top 100 sites on the web. Jared previously worked at a pioneering AI company.

---

Timestamps:

(0:00) Intro

(0:18) The YC product

(5:05) AI and the new builder

(13:01) Pivots and upcoming trends

(22:26) Making something people want

(24:50) What’s in store for SaaS

(33:02) Capital in the age of AI

(36:28) The human capacity for desire

(42:18) Building in America

(44:29) Fixing San Francisco

(47:58) Scaling YC

---

Links:

https://x.com/snowmaker

https://x.com/harjtaggar

https://x.com/garrytan

https://x.com/jaltma

https://www.ycombinator.com/

https://uncappedpod.com/

---

[email protected]

Bret Taylor is the founder and CEO of Sierra, an AI agent company transforming customer service. Bret’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI, co-creating both Google Maps and the Like button, and founding three companies.

We unpacked the so-called “SaaS-pocalypse” and what AI agents mean for the future of enterprise software. We talked through the shift from systems of record to autonomous agents, outcome-based pricing, platform transitions, Codex and the transformation of software engineering, and who is structurally positioned to win in the next era of AI.

---

Timestamps:

(0:00) Intro

(0:20) The SaaS-pocalypse and systems of record

(12:34) Sierra's competitive landscape

(17:05) Outcomes-based pricing

(24:22) The rapid evolution of AI support technology

(28:21) Young founders vs. experienced founders

(34:12) Beyond support: The full customer lifecycle

(38:47) Codex and the future of software engineering

(51:49) OpenAI and advertising

(54:59) How to run a board

---

Links:

https://x.com/btaylor

https://x.com/jaltma

https://uncappedpod.com/

---

Email: [email protected]

In this episode, the Benchmark partnership explains why they’ve resisted scale, eliminated residual economics, and built an equal partnership designed to endure. We talk about what that choice enables – for founders, for decision-making, and for practicing venture as a craft rather than a factory.

Peter Fenton is the longest-serving full-time general partner at Benchmark. Over the last two decades, Peter led investments in Twitter, Yelp, Elastic, Docker, Zuora, and many others. More recent investments include Sierra, Ollama, ClickHouse, and Airtable. Peter has been on the Forbes Midas list 18 years in a row.

Eric Vishria is a general partner at Benchmark. Eric led investments in Confluent and Amplitude, both of which IPO’ed in 2021. He is also an investor and board member at Cerebras Systems, Benchling, Contentful, among others. Most recent investments include Fireworks, Quilter, and Greptile. Before joining Benchmark, Eric was the co-founder and CEO of a social web browser company called Rockmelt, which was sold to Yahoo.

Chetan Puttagunta is a general partner at Benchmark. Eric is an investor and actively involved with Elastic (which IPO’ed in 2018), Legora, Manus, LangChain, Airbyte, Cursor, Reducto, Numeral, and the list of great companies goes on. Noteworthy exits include MuleSoft, which was acquired for $6.5B by Salesforce and Acquia, which was acquired for $1B in 2019. Prior to Benchmark, Chetan was a general partner at NEA for seven years.

Ev Randle is the newest general partner at Benchmark. Prior to joining the firm, Ev invested in Anthropic, Chainguard, Databricks, Flock Safety, and SpaceX, among others as a partner at Kleiner Perkins. Through his experience at Founders Fund and with personal capital, Ev also has invested in Rippling, Ramp, Wave, Faire, Figma, among others.

---

Timestamps:

(0:00) Intro

(0:18) Becoming more rare to stay small

(4:58) Activities that degrade with scale

(9:08) The principles of Benchmark

(14:07) Contributing as much as you take out

(18:37) Doing the right, hard-to-sell things

(23:31) Benchmark’s relationship with founders

(31:29) What makes a quality investor

(36:15) Cultivating different tastes in founders

(39:56) Spotting special people

(46:06) Consensus vs non-consensus bets

(47:50) Investing in founders, then AI

(53:06) Founder centricity matters more than ever

---

Links:

https://x.com/peterfenton

https://x.com/ericvishria

https://x.com/chetanp

https://x.com/EverettRandle

https://x.com/jaltma

---

https://uncappedpod.substack.com/

Email: [email protected]

Vinod Khosla and Keith Rabois are Managing Directors at Khosla Ventures.

Vinod 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. Vinod previously 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 incubated the idea for Juniper Networks to take on Cisco System’s dominance of the router market.

Keith is also currently the CEO of OpenStore and 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.

---

Timestamps:

(0:00) Intro

(0:58) The working relationship

(4:26) Pie chart on what’s discussed

(7:11) Ethos of investors today vs yesterday

(10:42) Comparing FF and KV

(12:46) What makes a great founder

(22:56) Alpha in today’s market

(30:05) Themes within AI

(38:23) AI companies built differently

(46:23) Excitement outside of AI

(53:12) Politically active on X

(58:24) Evolution of political leanings

---

More on Vinod:

https://x.com/vkhosla

https://www.khoslaventures.com/team/vinod-khosla

More on Keith:

https://x.com/rabois

https://www.khoslaventures.com/team/keith-rabois

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Daniele Perito is Co-founder and Executive Chairman of depthfirst, an AI-native security platform that understands your code, business logic, and infrastructure to find real vulnerabilities, slash false positives, and give developers actionable fixes in their workflow.

Daniele is also Co-founder and Board Member of Faire, where he previously served as Chief Data Officer and helped build the company’s data, risk, and analytics foundations from the early days to a multi-billion dollar valuation. Before co-founding Faire, Daniele worked at Square and was on the founding team of Cash App, where he focused on security, fraud, and risk systems supporting products used by millions of merchants and consumers.

We covered:

---

Timestamps:

(0:00) Intro

(0:40) The founding Faire insight

(4:34) Operational rigor of marketplace businesses

(10:39) Starting a company now vs in 2017

(12:01) The inception story of Cash App

(16:22) depthfirst’s mission

(18:08) AI security landscape

(26:10) Security is a fantasy world

(31:15) Building superhuman attackers for defense

(38:27) Roles of humans and AI in security

(39:14) Platform vs pipeline businesses

---

More on Daniele:

https://depthfirst.com/

https://www.linkedin.com/in/danieleperito/

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Ben Horowitz is a cofounder and general partner at the venture capital firm Andreessen Horowitz, a venture capital firm that manages $60 billion in assets under management. He is also the author of the New York Times bestsellers, The Hard Thing About Hard Things and What You Do Is Who You Are.

Prior to a16z, Ben was cofounder and CEO of Opsware (formerly Loudcloud), which was acquired by Hewlett-Packard for $1.6 billion in 2007. Earlier, he was vice president and general manager of America Online’s E-commerce Platform division, where he oversaw development of the company’s flagship Shop@AOL service. Ben also ran several product divisions at Netscape.

Ben serves on the board of Anyscale, Databricks, Mayvenn, NationBuilder, Navan, and UnitedMasters.

We covered:

---

Timestamps:

(0:00) Intro

(0:30) Marc and Ben’s relationship

(6:10) Structuring the firm to attract great talent

(10:28) Difference between execs and GPs

(14:51) Firm-wide guiding principles

(16:43) Scaling GPs vs small teams who concentrate

(20:11) Why scale is so important in venture

(23:45) What platform services work and don’t work

(26:58) Ben’s view on board seats

(34:56) The evolution of media

(44:44) Laws of physics for fund sizes

(48:28) Winning is more impactful than picking

(52:15) Defending why venture doesn’t scale

(55:00) Hiring ex founders and CEOs

---

More on Ben:

https://a16z.com/

https://a16z.simplecast.com/

https://x.com/bhorowitz

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Saam Motamedi is a General Partner at Greylock Partners working with enterprise software entrepreneurs at the seed and early stages who are focused on new opportunities in intelligent applications, cybersecurity, AI, and data infrastructure. In 2019 at just 26 years old, Saam became the Greylock’s youngest General Partner in its 54-year history – a remarkable achievement at an institution that had backed Airbnb, AppDynamics, Coinbase, Discord, Figma, Instagram, LinkedIn, among others.

Saam’s portfolio spans 14+ companies with collective valuations exceeding $10 billion. Abnormal Security, which Greylock incubated in its offices in 2018 with Saam as founding investor, grew into a multi-billion-dollar email security powerhouse. Cresta, where he led the Series A in 2019, became the leading generative AI platform for contact centers. Snorkel AI, Braintrust, Orb, and a portfolio of other infrastructure companies position Saam at the center of AI's business model transformation.

We covered:

---

Timestamps:

(0:00) Intro

(1:32) Greylock turning 60 this year

(4:11) What’s persisted since 1965

(8:59) Apprenticeship

(11:34) What's durable in venture

(16:29) Greylock’s ethos

(19:33) Incentive misalignments

(24:44) Breadth vs depth in venture

(29:28) Managing the team on inputs

(34:00) Why incubations are so hard

(43:22) Finding alpha

(52:38) Greylock’s approach to portfolio services

(59:18) Assessing wild revenue ramps

(1:08:10) Horizontal vs vertical SaaS

(1:11:34) Friendships and work

(1:16:26) Saam's biological age

---

More on Saam:

https://greylock.com/

https://x.com/saammotamedi

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]

Pat Grady and Alfred Lin are partners at Sequoia and were recently named as the storied firm’s new co-stewards. Alfred joined the firm in 2010, where he has led major investments into category-defining companies like Airbnb, DoorDash, and Kalshi. Pat has been a partner at the firm for nearly 19 years and has led Sequoia’s growth-stage investing since 2015, backing companies like Snowflake, OpenAI, and Harvey. In this episode, we unpack how Sequoia actually works: their partnership model, how they pick outliers, and what stewardship means inside one of the most respected firms in venture capital.

Some highlights:

---

Timestamps:

(0:00) Intro

(1:01) Initial mindset as stewards

(4:30) The business of outliers

(6:27) Managing the inputs in venture

(12:11) Sourcing coverage goals

(17:57) Seeing the right companies

(22:36) Proprietary map of talent

(24:39) The impact of great engineers

(29:06) Picking winners with conviction

(36:26) Coaching asymmetry into picking

(43:16) Mentoring younger investors

(46:45) Frameworks on picking

(53:20) What it takes to win

(58:32) How to onboard with a founder

(1:02:59) Proudest board seats

(1:06:12) 2026 in the new roles

---

More on Pat & Alfred:

https://sequoiacap.com/

https://x.com/gradypb

https://x.com/Alfred_Lin

More on Jack:

https://www.altcap.com/

https://x.com/jaltma

---

https://linktr.ee/uncappedpod

Email: [email protected]