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The Penumbra Podcast

Harley Takagi Kaner and Kevin Vibert

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At the Penumbra, you might follow Juno Steel, a brooding, sharp-witted private eye on Mars, as he tangles with an elusive homme fatale, tracks dangerous artifacts of an ancient alien civilization, and faces his three greatest fears: heights, blood, and relationships. Or you might enter the world of the Second Citadel, where the merciless Sir Caroline must corral a team of emotionally distraught all-male knights to defend their city against mind-manipulating monsters...even the ones they’ve f ...
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The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show note ...
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The City of Steel Podcast

City of Steel Podcasting Team

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City of Steel follows the story of five supernaturally-savvy investigators in Sheffield as they discover secrets, solve mysteries and combat vampires, demons and rogue wizards to bring peace to the Steel City. We tell this story as an actual-play podcast using the Dresden Files RPG system.
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Alexis Ohanian is the Founder and General Partner of Seven Seven Six, an early-stage venture capital firm with $970M AUM. Prior to 776, Alexis was the Co-Founder of Initialized, one of the most successful early-stage firms in history with their first fund returning 56x DPI. Before Initialized, Alexis was a Partner at the world-famous Y Combinator a…
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Joe is back with more news and notes from around the National Football League. The hot and heavy rumors of the Pittsburgh Steelers trying to acquire San Francisco 49ers wide receiver Brandon Aiyuk heated up again this week, with several other teams reportedly interested in trading for the player. Will Steelers GM Omar Khan pull the trigger? Or woul…
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Well, Juno Steel. Time's up. It's time to answer the question: Who will you be next? Welcome to the Penumbra, dear Traveler. We hope you enjoy your stay. (Trigger warnings can be found at the bottom of this episode description and at the end of the transcript.) ------- You can find all of our transcripts here: https://drive.google.com/drive/folders…
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David Cahn is a Partner @ Sequoia Capital, one of the great venture firms of the last 5 decades. Before joining the Sequoia partnership, David led Coatue's venture business as a General Partner and COO where he led investments in Hugging Face, Runway and Supabase. David also joined the boards of Weights & Biases and Replit. In Today's Episode with …
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Ben Fiechtner is Chief Revenue Officer at Clari, where he drives global go-to market & revenue operations. Ben previously served as SVP at UiPath, growing their key accounts and regulated industry verticals from $150m to $450m. Before UiPath, Ben was at Salesforce where he held multiple senior roles, achieving significant year-over-year growth and …
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Joe shares firsthand accounts from Pittsburgh Steelers training camp in Latrobe, Pennsylvania as the team put on the pads this week. There’s been a lot of chatter about the Steelers starting quarterback job. Russell Wilson returned to practice while Justin Fields continues to take the bulk of first-team reps. But is there a competition? Also, which…
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Ethan Mollick is the Co-Director of the Generative AI Lab at Wharton, which builds prototypes and conducts research to discover how AI can help humans thrive while mitigating risks. Ethan is also an Associate Professor at the Wharton School of the University of Pennsylvania, where he studies and teaches innovation and entrepreneurship, and also exa…
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Delian Asparouhov is a Partner at Founders Fund and Co-Founder and President of Varda Space Industries, which is building the world's first space factories. At Founders Fund Delian has led deals in the likes of Ramp ($7BN) and Sword Health ($3BN) among others. Before joining Founders Fund, he was a Principal at Khosla Ventures, Head of Growth at Te…
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Nilan Peiris is Chief Product Officer at Wise, where he leads on growth across channels including product and platform. Prior to Wise, Nilan was VP Growth at HouseTrip, in charge of scaling the company’s growth in the European market. He’s also worked as Chief Marketing Technology Officer at Holiday Extras, where he was responsible for all areas of…
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Zac is back just in time for the Pittsburgh Steelers to report to training camp. He joins Joe, as the two drill through the team roster and highlight who and what they’re most excited to see in Latrobe. Questions or Comments? Call the Steel City Underground Fan Line and have your question played on our podcast! The best questions will be answered i…
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Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com. In Our Second Episode of This Week in SaaS: …
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Kevin Hartz is a Co-Founder and General Partner at A*, an early-stage venture capital firm. Prior to founding A*, Kevin co-founded Eventbrite, a publicly traded company, and served as the CEO for the first 11 years of the company. Before Eventbrite, Kevin co-founded Xoom, a money remittance company that was acquired by PayPal in 2015 for over $1BN.…
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Cameron Adams is Chief Product Officer and co-founder of Canva where he is responsible for heading up the design and product teams. Since launching in 2013, Canva’s global community has grown to over 185 million monthly users in over 190 countries. In 2021, Canva was valued at $40 billion, following a $200m funding round. This saw it become one of …
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Joe and Brian discuss the possibility of the Pittsburgh Steelers making a trade with the San Francisco 49ers for wide receiver Brandon Aiyuk. Hear why the hosts think the trade might not happen and why the Steelers may be wise to steer clear of a deal for Aiyuk instead of other options. Also, what are the deepest position groups on the Steelers dep…
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Pedro Franceschi is the Co-Founder and CEO @ Brex, the AI-powered spend platform with tens of thousands of customers, including DoorDash, Coinbase, Robinhood and Roblox. Pedro has raised over $1.2BN for the company from the likes of Greenoaks, Ribbit, DST, Bond and YC. The latest reported valuation was $12.3BN. Before Brex, Pedro was the first pers…
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Given but one short and precious life, what world will you bring to bear? Welcome to the Penumbra, dear Traveler. We hope you enjoy your stay. (Trigger warnings can be found at the bottom of this episode description and at the end of the transcript.) ------- You can find all of our transcripts here: https://drive.google.com/drive/folders/1OLddnnYam…
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Saam Motamedi is a General Partner at Greylock, where he has led investments in Abnormal Security (incubated at Greylock), Apiiro Security and Opal Security, as well as AI companies like Adept, Braintrst, Cresta, Predibase, Snorkel, and more. Before Greylock, Saam founded Guru Labs, a machine learning-driven fintech startup, and worked in product m…
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Mark Roberge is a Co-Founder and Managing Director at Stage 2 Capital and a Senior Lecturer at the Harvard Business School. Prior to these roles, Mark was the founding CRO at HubSpot, where he scaled ARR from $0 to $100 million and expanded his team from 1 to 450 employees. Mark was ranked #19 in Forbes' Top 30 Social Sellers in the World. He was a…
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Ara Mahdessian is the Co-Founder and CEO @ ServiceTitan, one of the great vertical SaaS business of the last decade. Today the company powers over 11,800 trade customers and has raised over $1.4BN from some of the best including Bessemer, Battery, Index, ICONIQ and more. Their latest valuation pegged the business at a reported $7.3BN. In Today's Ep…
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Joe and Brian return for their yearly tradition of guiding fans in the right direction for their next jersey purchase. However, the discussion is more in-depth than it would appear on the surface, as many key factors decide whether a player’s jersey is a wise investment. Join the hosts as they dig into these elements and some side stories on some p…
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Pat Grady is one of the most successful growth investors of the last decade. As the Head of Sequoia's growth investing practice, Pat has invested in companies with a combined market cap exceeding $250BN. Among Pat's immense portfolio is Hubspot, Snowflake, ServiceNow, Okta, Amplitude, Zoom and Qualtrics. Pat is also one of the best acquirers of tal…
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Joe and Brian continue their deep dive into the Steelers position groups by briefly looking at the quarterbacks and asking if the offensive line changes are enough to improve the offense in 2024. The hosts pontificate how starting two rookies and shifting a second-year tackle to the left side could impact the team. Will it be better? Could it be wo…
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Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you m…
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Above, a cataclysmic war to determine the fate of the Universe; below, an adventure deep into the bowels beneath an undersea palace; all while a traitor leads the enemy onward... and forces our heroes to make a terrible choice. Welcome to the Penumbra, dear Traveler. We hope you enjoy your stay. (Trigger warnings can be found at the bottom of this …
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Matt Clifford is the Co-Founder of Entrepreneur First (EF), the leading global talent investor and incubator. EF has incubated startups worth over $10bn, including Cleo, Tractable and Aztec Protocol. Matt is also Chair of ARIA, the UK’s Advanced Research and Invention Agency, and advises the UK government on AI and in 2023 served as the Prime Minis…
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Samir Vasavada is the Co-Founder & CEO of Vise, a technology-powered asset manager. Samir and his co-founder, Runik founded Vise from the Midwest at 16 years old. They bootstrapped the company before dropping out of high school and raising $128M in just 6 months from some of the best including Sequoia Capital and Founders Fund. The company achieved…
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Joe and Brian return to make pre-camp roster predictions for the Pittsburgh Steelers. Which position groups are the weakest? Which players are on the borderline of making the team? And who are our “locks” and sleeper picks to make the 53-man roster? Please tune in for this talk and more in our latest episode celebrating ten years of Steel City Unde…
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Andrew Bialecki is the Co-Founder and CEO of Klaviyo, the platform that powers smarter digital relationships for businesses and their data. To date, Klaviyo has raised over $778M from the likes of Accel, Summit Partners, Sands Capital, and Shopify, and raised an additional $700M after its IPO in September 2023. In Today’s Episode with Andrew Bialec…
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David Luan is the CEO and Co-Founder at Adept, a company building AI agents for knowledge workers. To date, David has raised over $400M for the company from Greylock, Andrej Karpathy, Scott Belsky, Nvidia, ServiceNow and WorkDay. Previously, he was VP of Engineering at OpenAI, overseeing research on language, supercomputing, RL, safety, and policy …
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Val Scholz is the former Head of Growth @ Revolut, where he led the company to their first 10M users. Post Revolut, Val played a crucial role in scaling several high-growth companies including VEED, Simple & Busuu (exited for $400M). Today, Val is the Head of Growth at Kittl, an intuitive design platform empowering graphic designers. In Today’s Epi…
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Last week the Pittsburgh Steelers signed head coach Mike Tomlin to a new three-year extension. There was mixed reaction from the media, including those who were negative over the move stating Tomlin’s lack of recent playoff victories. However, is Mike Tomlin to blame for all of those losses? Joe digs deeper than the surface to ask if Tomlin gets th…
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Michael Eisenberg is a Co-Founder and General Partner @ Aleph, one of Israel's leading venture firms with a portfolio including the likes of Wix, Lemonade, Empathy, Honeybook and more. Before leading Aleph, Michael was a General Partner @ Benchmark. In Today's Show with Michael Eisenberg We Discuss: 1. The State of AI Investing: Why does Michael be…
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The center of the Universe, mere hours before the battle that will determine its final fate. This is a war that not all will survive. Welcome to the Penumbra, dear Traveler. We hope you enjoy your stay. (Trigger warnings can be found at the bottom of this episode description and at the end of the transcript.) ------- You can find all of our transcr…
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Danny Rimer is a Partner @ Index Ventures and one of the most prominent VCs of the last two decades. Danny has led Index to be one of the top global firms on both sides of the Atlantic. Among Danny's incredible portfolio, he has led or been involved with Figma, Discord, Dream Games, Etsy, Glossier and Patreon. In Today's Discussion with Danny Rimer…
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Janie Lee is the Head of Product and the owner of the Self-Serve business at Loom. Janie previously worked at Rippling, leading the Identity Management and Hardware teams. Prior to that, she worked at Opendoor launching markets and developing pricing algorithms. During this time, Opendoor scaled from 2 to 20+ markets, $5B+ revenue, and 1500+ employ…
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Joe returns to discuss the new three-year extension for Pittsburgh Steelers head coach Mike Tomlin. The positives of Mike Tomlin as the Steelers head coach far outweigh the negatives, no matter what some fans might say. Joe also digs into the myths of “inheriting Cowher’s players” and how playoff success, or failure, should not be the only benchmar…
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Alex Wang is the Founder and CEO @ Scale.ai, the company that allows you to make the best models with the best data. To date, Alex has raised $1.6BN for the company with a last reported valuation of $14BN earlier this year. Scale tripled their ARR in 2023 and is expected to hit $1.4BN in ARR by the end of 2024. Their investors include Accel, Index,…
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