Venture with Grace

Jack Raines is a Forward Deployed Personality Hire at Slow Ventures, where he scouts the bold, the obsessive, and the slightly unhinged founders building the next wave of breakout companies. Before VC, Jack built a 65,000-subscriber Substack that landed him a Penguin book deal, wrote 50,000 words in 14 days, and worked across Robinhood’s Sherwood News, Litquidity, and UPS. A creator turned investor, he blends storytelling with venture to back founders and influential creators who want to build real businesses—not just audiences. His first book, a guide to navigating your 20s, comes out in 2026.Topics: Creator → Investor: Why Audiences Became the New Due DiligenceHow Slow Ventures Finds “Moderately Unhinged Founders”Investing in the Creator-Led Startup#VC #Startups #Creators #FounderLife #SlowVentures #JackRaines

Denise Teng is a Partner at Gradient. Prior to joining Gradient, Denise spent six years as a product manager. Most recently, she was a PM on the Meta AI platform team where she built infrastructure tools for ML workflows. Denise previously spent time at Twitter as a senior PM where she launched products ranging from ad tech and social commerce to real-time data analytics. After grad school, she joined the Walmart e-commerce APM program where she scaled merchant-facing products for Walmart marketplace and supported the post-acquisition integration of Jet.com. Denise obtained an M.S. in software management from Carnegie Mellon University. Topics: Building AI infra and ML workflows from big tech to startupsHow a product manager’s mindset shapes AI and infra investingTactical fundraising and GTM advice for AI/infra founders#AIVC #GradientVentures #MLInfra #AIStartups #VCPodcast #ProductToVC

Rob Ferguson is the CTO and Head of AI at Microsoft for Startups, where he helps high‑growth founders access GPUs, frontier models, and strategic partnerships to scale AI products. A veteran engineering leader with more than two decades in AI and infrastructure, he previously served as Global Head of AI/ML for Startups and VC at AWS and has been a three‑time startup CTO/VPE with over $100M in exits, including Automatic Labs’ acquisition by SiriusXM. He has scaled engineering teams from early seed stages to hundreds of people at companies like Automatic Labs and Standard Cognition, and is known for making early, market‑shaping bets on platforms such as Databricks, Weights & Biases, and Ray. As a global AI keynote speaker, he focuses on turning cutting‑edge AI—LLM ops, RAG, and distributed training—into pragmatic playbooks for founders, enterprises, and investors navigating hyperscale cloud and modern AI infrastructure.Topics: How Hyperscalers Actually Evaluate AI StartupsLessons From Being a Three-Time Startup CTOThe 2026 AI Infrastructure Landscape#AIInfrastructure #StartupFounders #VentureCapital #CloudComputing #AIEngineering

Chappy Asel serves as Co-Founder and Executive Director of The AI Collective, the largest grassroots AI community in the US with over 25,000 members across major tech hubs, fostering in-person events and online forums for founders, researchers, operators, and investors to shape AI's future. A self-taught coder from age 12, he built and sold the world's #1 homework app with 338k installs before roles at Apple—contributing to Vision Pro prototypes, Apple Intelligence, App Intents, and AI/ML eye-tracking—and brief stints at Meta and Xevo. He also founded a top-rated weightlifting app (70k+ installs), Cofactory, and a stealth project on social capital allocation, while pursuing competitive natural bodybuilding, reading 50-100 books yearly, and scouting for ventures like Madrona.AJ Green is the Founding Director of Growth at The AI Collective, where he leads the expansion of the world’s largest AI nonprofit community. He views AI as the most disruptive force humanity has ever discovered and is dedicated to building systems that provide asymmetric leverage, transforming compounding intelligence into exponential opportunities. AJ aims to create defining cultural moments in AI history through his work, driving impactful growth and engagement within the AI ecosystem.Topics: Building the Largest Grassroots AI CommunityPatterns among the top early-stage AI teamsWhat the AI Talent Stack Looks Like in 2026#AI2026 #FutureOfAI #AIAgents #AICommunity #AgenticWorkflows

Madison is a Partner at NEA investing in early-stage data, infrastructure, developer tools, data science, and AI and she also leads the data and AI initiative internally for data-driven investment decision-making. She has invested in and works with companies including Factory, Datafold, Metabase, Foresight Data, Delphina, Fixify, World Labs, Sakana and more. Prior to investing, Madison was Head of Data Science and Machine Learning at growth startup Thrasio, Head of Data Science at Greycroft, and led a data science team at Facebook focused on the ad auction and deep learning with FAIR. Madison received a BS in Engineering from Stanford and grew up in Colorado performing in rodeos. She spends free time advising entrepreneurship organizations at Columbia, UWashington and Stanford. Topics: How AI and data tools are changing the way every company builds softwareWhat makes a technical founder stand out todayWhere AI infra is headed next #VentureCapital #AIInfrastructure #DeveloperTools #DataScience #MachineLearning

Alex Lee is the Co-Founder and CEO at Truewind, a venture-backed technology startup building AI for Accountants. Trusted by 200+ businesses and accounting firms, including EisnerAmper and Frank Rimerman, Truewind raised $17 million from Thomson Reuters Ventures, Rho Capital, Pathlight Ventures, and Y Combinator. Previously, Alex was a venture capital investor at Alliance Ventures and Schematic Ventures, where he invested in early stage startups and provided finance support to the portfolio companies. Alex received his MBA from Columbia University and BS in Aerospace Engineering from USC. Topics: – The future of AI-powered accounting and why bookkeeping is being rebuilt from scratch– Lessons from switching sides: how VC experience shaped the way he builds Truewind– Scaling an AI startup serving accountants — trust, accuracy, and workflow replacement#AI #AccountingTech #StartupLeadership #Automation #VentureCapital

Harry Qi is the co-founder and CEO of Motion, an AI-native productivity company building an “agentic work suite” that uses autonomous agents to manage calendars, tasks, and workflows for knowledge workers and SMBs. A former hedge fund analyst, he left a seven‑figure finance career in his early 20s to found Motion in 2019 with friends Omid Rooholfada and Ethan Yu, taking the company through Y Combinator’s Winter 2020 batch and scaling it to over 100,000 customers worldwide. Under his leadership, Motion has raised tens of millions in venture funding and is positioning itself as an AI-first alternative to traditional productivity suites by deeply integrating multiple specialized agents—like executive assistant, sales, and marketing agents—into one cohesive platform.Topics: Why the future of productivity is agent-first, not app-firstHow Motion reached 100k customers by solving “calendar chaos”Leaving hedge funds for YC: what Harry learned switching from finance to AI#AI #FutureOfWork #Productivity #SaaS #StartupLessons

Robert LoCascio Founded a new company in 2023 called Eternos.life which became Uare.ai and is providing a platform for prosumers and consumers to create their own individual AIs for both work and personal use. Previously, Rob was the Founder of LivePerson, Inc. (LPSN: NASDAQ ), and was its Chief Executive Officer from 1995 to 2023. He was the guiding force behind the company’s vision of creating meaningful connections between brands and consumers and was the original inventor of web chat. Rob’s interests extend beyond his business and reflect his close ties to New York City. He is a founding member of Equal AI and NYC Entrepreneurs Council of the Partnership for New York City. In 2001, he started the Dream Big Foundation with its first program FeedingNYC, which gives families in need a Thanksgiving dinner. To date, FeedingNYC has donated more than 40,000 meals. Its second program, the Dream Big Entrepreneurship Initiative, launched in 2014 to fund, mentor, coach, and empower local entrepreneurs in underserved communities.Topics: The Future of Personal AIBuilding Consumer AI ProductsFounder Psychology & Longevity#AI #PersonalAI #Founders #FutureOfWork #TechInnovation #Leadership #VentureWithGrace

Gabriel Jarrosson is the Founder and Managing Partner of Lobster Capital, an early-stage fund that invests exclusively in the top-performing Y Combinator startups. After bootstrapping a prior company to $1M ARR with no employees and investing tens of millions of dollars across 100+ YC companies, he built Lobster Capital around a traction- and data-driven thesis, backing the top 2% of YC teams and coaching them through the messy realities of product-market fit, founder psychology, and scaling. Topics: Inside the YC Power Curve: How Lobster Capital Identifies the Top 2% of FoundersFounder Psychology: Lessons From Backing 100+ YC Teams Through Chaos and BreakthroughsA Bootstrapped Operator’s Playbook: From $1M ARR Solo to a Data-Driven VC Fund#VentureCapital #YCombinator #StartupGrowth #FounderJourney #EarlyStageVC

Benjamin Orthlieb is the Co-Founder & GP at Blue Moon, a seed fund backing B2B founders across North America. Ben is building a modern venture model — human focused, powered by data and AI. Founders consistently tell him they love the approach because it feels like working with a tech startup as much as a VC. Before Blue Moon, Benjamin spent nearly two decades leading strategy, M&A, and venture investing teams. At LinkedIn, he led the Corporate Development & Strategy team, partnering with executives to drive growth through acquisitions, investments, and strategic planning. Earlier, he worked with founders and Fortune 500 leaders as a Principal at BCG and held roles in banking at Barclays Capital and BNP Paribas. He holds an MBA from Wharton, a CFA charter, and an MS in CS & EE Engineering from Télécom SudParis / Institut Polytechnique de Paris.TopicsBuilding a Modern VC Model: Human-Focused, Data-Driven, AI-PoweredLessons From 20 Years in Strategy, M&A, and Corporate Development at LinkedIn & BCGBacking B2B Founders Across North America: What Ben Looks for in Seed Investments#VentureCapital #SeedInvesting #B2BStartups #AIandData #Entrepreneurship

Gil Rosen is the President of the Stanford Blockchain Accelerator, and co-teacher of CEE246A Web3 Entrepreneurship in the Stanford School of Engineering. Gil aims to nurture the future of Blockchain and Web3 as a sustainable force for good - building infrastructure, organizational models, and technology, that serve humanity and our ecosystem rather than extract. Gil is the founder of HeadandHeart.capital, an angel fund aligning social impact with venture returns investing in blockchain, fintech, healthtech, and sustainability in the US and LatAm. A former serial entrepreneur and data guru, Gil leverages his experience and network to support authentic entrepreneurs building transformative companies. In 2022 Gil returned to Stanford to research healthcare, economic development, and opportunities for data science and web3 to tackle their intransigence.Topics: Building Blockchain for Good: Creating Human-Centered, Sustainable Blockchain Infrastructure The Future of Impact-Driven Venture: Aligning Returns with Societal and Environmental OutcomesLessons from Stanford’s Blockchain Accelerator: What Authentic Founders Are Building in 2026#BlockchainInnovation #ImpactInvesting #FutureOfTech #Entrepreneurship

Ville Tuulos is the Co-founder & CEO of Outerbounds. Outerbounds is a company developing modern human-centric ML. Ville has been developing infrastructure for machine learning for over two decades. He has worked as an ML researcher in academia and as a leader at a number of companies, including Netflix where he led the ML infrastructure team that created Metaflow, a popular open-source framework for ML infrastructure.He is also the author of an upcoming book, Effective Data Science Infrastructure, published by Manning.Topics: Building Metaflow at Netflix: Lessons in Scalable, Human-Centric ML InfrastructureWhy the Future of ML Platforms Is Human-First, Not Tool-FirstOuterbounds: From Open Source to a Full-Stack Platform for Production-Grade ML#MachineLearning #MLOps #AIInfrastructure #OpenSource #DataScience

Jason Saltzman, Head of Insights at CB Insights. Jason leads the insights function at CB Insights, delivering predictive intelligence on the companies and technologies defining the future. Prior to CB Insights, Jason led marketing and insights at Live Data Technologies and built GTM functions for 25+ startups at Verbatim. He is also a former professional cyclist.Topics: The future of AI, enterprise software, and emerging techThe industries primed for hyper-growth in 2026How CB Insights predicts the next breakout startups & technologies#futureoftech #2026trends #cbinsights #startups #AIinnovation

Vivek Ladsariya is a Managing Director at PSL and general partner of PSL's venture capital firm, PSL Ventures. Vivek will play a pivotal role in leading external pre-seed and seed investments out of PSL Ventures’ $100 million Fund II, actively investing in new Pacific Northwest technology companies. The majority of the fund’s portfolio consists of companies where PSL Ventures led an initial round within weeks of company formation, and roughly half of all PSL investments are AI-enabled software companies.Vivek focuses on investing across deeply technical investment themes including AI, cybersecurity, infrastructure, industrial tech, and devops. As a recovering founder, Vivek is deeply passionate about partnering with founders as they build category defining companies.Topics: How PSL Writes the First Check Into Category-Defining StartupsInvesting in AI-Enabled Software Before Product ExistsWhat PSL Looks For in Deeply Technical Founders#AI #DeepTech #VentureCapital #Startups #Cybersecurity #Infrastructure

Aditya Naganath joined Kleiner Perkins’ investment team in 2022 with a focus on artificial intelligence, enterprise software applications, infrastructure and security. Prior to joining Kleiner Perkins, Aditya was a product manager at Google focusing on growth initiatives for the next billion users team. He previously was a technical lead at Palantir Technologies and formerly held software engineering roles at Twitter and Nextdoor, where he was a Kleiner Perkins fellow. Aditya earned a patent during his time at Twitter for a technical analytics product he co-created.Originally from Mumbai India, Aditya graduated magna cum laude from Columbia University with a bachelor’s degree in Computer Science, and an MBA from Stanford University. Outside of work, you can find him playing guitar with a hard rock band, competing in chess or on the squash courts, and fostering puppies. He is also an avid poker player.Topics: From Palantir to KP: What Real Technical Rigor Looks Like in AI StartupsHow AI Infrastructure Is Being Rewritten — and What Founders Keep Getting WrongLessons from Google’s Next Billion Users Team: Building for Massive, Global Scale#VentureCapital #AI #EnterpriseSoftware #TechInfrastructure #StartupFounders