The Venture Variety Show

Cherae Robinson, Head of Platform & Marketing at Flybridge, is a former travel startup founder turned VC expert. She discusses the evolving role of platform teams in venture capital, emphasizing their importance beyond just financial support. Cherae shares insights on building trust with founders, the critical role of go-to-market specialists, and how her background informs her approach. Plus, she lightens the mood by talking about her passion for DJing at events, blending creativity with venture capital!

Episode SummaryIn this episode of The Venture Variety Show, I talk with Tony Stubblebine, CEO of Medium, about the power of writing in a noisy, AI-driven world.Tony shares why storytelling is still the most underrated skill in entrepreneurship—and how Medium is helping real voices rise above the noise. We dive into writing as a strategic edge, how platforms shape behavior, and why user-generated content still matters more than ever.“You are an expert in your own life.”“Writing gives you an opportunity to clarify your thoughts, to research something, and then to demonstrate that you're really smart.”Whether you're a founder, investor, platform specialist, or just trying to cut through the content clutter, this one’s for you.Key Takeaways🔶 Why writing remains a founder superpower🔶 How Medium supports real voices—not clickbait🔶 What AI can’t replace in storytelling and context🔶 Why lived experience > performance content🔶 How to stand out without being an internet hustlerChapters00:00 – Welcome + Meet Tony01:11 – Bootstrapping vs. VC: What founders learn02:53 – The emotional power of writing05:36 – Writing as a founder’s strategic edge09:02 – Why AI summaries fall short12:09 – Medium’s mission: Make amateur writing cool again14:45 – Finding your niche & owning your voice18:04 – The future of blogging and lived experience20:48 – How to get started on Medium21:34 – Wrap-up and final thoughtsKeywordsstorytelling, entrepreneurship, writing, Medium, AI, blogging, platforms, user-generated content, startup strategy, content creation, differentiation Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Multi-Sapiens Teams: Managing AI Agents in the Real World with Tatyana MamutKeywordsAI agents, Wayfound, multi-sapiens teams, future of work, human-AI collaboration, team structure, trust in AI, workplace culture, AI leadership, anthropology, AI operationsSummaryIn this episode, I talk with Tatyana Mamut, co-founder and CEO of Wayfound, about how AI agents are already reshaping teams, operations, and leadership. With a background in anthropology and product leadership, Tatyana brings a unique perspective to managing AI agents in the workplace.We explore how AI agents interact with each other, how they’re embedded into real company workflows, and why building a “multi-sapiens” workplace — where humans and AI agents work side by side — is essential for the future of work.Key Takeaways🔶 Wayfound helps businesses manage AI agents alongside human teams🔶 AI agents are handling operational tasks like investor updates and customer research🔶 Agents interact — and sometimes argue — much like human teammates🔶 Managing AI agents requires trust, oversight, and clear role definitions🔶 Fear of AI can hold companies back, but adaptability unlocks new opportunities🔶 AI agents free up humans to focus on relationships, leadership, and creative work🔶 The future of work is “multi-sapiens” — humans and AI agents collaborating as part of the same teamSound Bites“We’re building a multi-sapiens workplace — humans and AI agents side by side.”“AI agents can argue, correct themselves, and interact — just like humans.”“We should not enslave AI. That never ends well.”“The future belongs to those who move forward with adaptability, optimism, and imagination.”Chapters00:00 — Intro: AI’s impact on work and leadership01:05 — Managing AI agents: Wayfound’s approach03:00 — Real-world examples of AI agents in operations05:30 — Agent-to-agent interactions and surprising dialogue08:45 — Why Wayfound avoids anthropomorphizing AI10:00 — Building trust between humans and AI agents13:30 — AI agents free humans to focus on relationships and strategy16:00 — Fear, job displacement, and lessons from history19:15 — Cultural evolution and the rise of multi-sapiens teams22:40 — The future of AI agents — and the choices ahead Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Alternative Titles:— Entrepreneur-Led Funds Are Changing the Future of Venture— How VC, PE, and Corporate Investors Are Converging — And What It Means for StartupsKeywords:emerging managers, venture capital, private equity, fund administration, corporate venture, diversity in venture, liquidity, founder-led funds, fundraising trends, investment landscapeEpisode Summary:In this episode of The Venture Variety Show, Braughm Ricke, founder and CEO of Aduro Advisors, joins the conversation to share insights from over two decades in venture capital and private equity.With his firm supporting more than 600 funds managing $140 billion in assets, Braughm offers a unique view of how the investment world is evolving — from the rise of entrepreneur-led funds to the growing overlap between venture capital, private equity, and corporate investors.Key Takeaways:— Why more founders and investors are launching funds like startup— How venture capital and private equity are blending, reshaping funding and liquidity options— The evolving role of corporate venture arms and their strategic value-add beyond capital— Diversity trends in fund management and emerging managers— What founders, fund managers, and startups should know about today's market dynamicsNotable Quotes:"Building a firm is very much a startup in and of itself." — Braughm Ricke"The lines between VC and PE are blurring.""CVCs are stepping up with real strategic value, not just capital."Chapters:00:00 — Intro to Braughm Ricke and Aduro Advisors02:15 — The rise of emerging managers and founder-led funds05:22 — Corporate venture arms evolving beyond just capital08:20 — Diversity in fund management and venture leadership10:18 — How VC and PE are blending together13:51 — Market outlook, fundraising trends, and new capital sources18:30 — Challenges and opportunities for emerging managers Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Episode Title: From Deep Tech to Ikigai to Yoga – A VC’s Purposeful Path with Kira NoodlemanSummary:In this episode of The Venture Variety Show, host Alastair Goldfisher sits down with Kira Noodleman, partner at Bee Partners, to explore what it means to invest at the edge of innovation and humanity. Kira shares her nontraditional path into venture capital, her thesis on deep tech and “machines will win,” and how Bee Partners supports early-stage founders with more than just capital. From discussing AlphaFold and AI's impact on R&D to reflecting on yoga, founder psychology, and building with intention, this conversation spans strategy, soul, and science.Topics Covered:Deep tech, AI, and the "super cycle" of innovationKira’s product background and path into ventureHow Bee Partners supports early-stage foundersThe importance of founder psychology and human connectionWhy yoga, storytelling, and personal journey matter in ventureDEI in startups and modifying term sheets for equityHow regional ecosystems (SF, Denver, NYC) shape the startup experienceWhat the future of lean, AI-powered startups looks likeChapters:00:00 – Intro01:13 – Kira's Path Into Venture03:51 – Machines Will Win05:47 – Deep Tech Deltas Defined08:32 – AI Converging with Deep Tech09:50 – AlphaFold10:25 – Supporting Entrepreneurs12:55 – Pathfinders Podcast15:11 – Looking for Ikigai and Pathfinders17:56 – Getting to Know Founders via Yoga18:39 – SF vs. Denver vs. NYC23:16 – Supporting the Underrepresented25:19 – Importance of DEI26:16 – Outlook in Venture27:39 – Connect with Kira28:27 – OutroKey Takeaways:Kira’s venture path began in global product management.Deep tech investing requires patience, partnership, and technical risk mitigation.AI is accelerating innovation cycles and changing how early-stage companies operate.Bee Partners values collaboration, founder well-being, and long-term support.Kira’s Pathfinders podcast highlights the personal side of the founder journey.DEI isn’t just a talking point — it’s built into Bee’s team, term sheets, and community work.NYC’s density of customers offers a different kind of opportunity than SF or Denver.The next unicorn may be built by 5 people and 100 AI agents.Sound Bites:"We believe machines will win.""It’s about timing and execution.""We’re calling it a super cycle.""Sometimes digitizing is innovation."Connect with Kira:Find her on LinkedIn or visit https://beepartners.vc/ Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Episode Title:How Overlap Helps Frontier Tech Founders Scale SmarterWith Justin Stevens, Founder & CEO of Overlap HoldingsKeywordsFrontier Tech, Debt Financing, Venture Capital, Capital-Intensive Startups, Fundraising Strategy, Equity vs Debt, Startup Advice, Relay Race Funding, Financial StructuringEpisode SummaryWhat if your cap table isn’t your only tool for growth?In this episode, Justin Stevens — founder of Overlap Holdings — explains why founders in capital-intensive sectors like climate, robotics, and life sciences need more than just equity to scale.With nearly 20 years of experience on Wall Street (including 18 years at Apollo), Justin shares how Overlap combines traditional venture investing with a capital solutions business that helps startups raise smart, non-dilutive capital from a network of over 200 lenders.If you're raising a Seed, Series A, or B — or just planning what's next — this episode offers a tactical breakdown on how to think more strategically about capital.Top TakeawaysFounders often over-rely on equity — even when debt may be cheaper and more flexibleOverlap’s hybrid model combines VC checks with hands-on capital strategy supportThere are four key types of startup debt — and understanding them is a competitive edgeLenders are pattern matchers — and Overlap helps you find the right fitFundraising is a relay race — founders need to plan ahead for who takes the next legSound Bites“We think of capital the way most founders think of product: deliberately, strategically, and iteratively.”“Every lender has a tiny underwriting box — line up 200 of them and you cover the whole waterfront.”“Venture equity is often the most expensive capital you’ll ever take.”Chapters00:00 — Intro01:16 — What is frontier tech — and why it needs a different capital model07:59 — The four types of debt startup founders should understand13:21 — Capital solutions: Overlap’s second line of business20:45 — Advice for founders navigating capital-intensive growth24:00 — The relay race metaphor for funding strategy25:00 — Why Overlap blends Wall Street structure with startup energy Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Episode SummaryIn this episode of The AI Cognitive Shift, host Alastair Goldfisher interviews Andy Mowat, founder of Whispered, a platform reinventing how executives find their next role. They discuss the hidden job market, the growing role of AI in recruitment, and why personal relationships still carry more weight than résumés. Andy explains how Whispered blends AI with a human-first approach to help leaders navigate their career journeys.KeywordsAI recruiting, executive search, Whispered, unposted jobs, networking, job market trends, hiring tech, career strategy, future of work, VC talentKey TakeawaysMost executive roles are never posted publicly—they're shared through personal networks.AI is helping screen and organize applicants but can’t replace human decision-making.Whispered uses AI to scale executive coaching and unposted role discovery.Networking remains one of the most effective ways to land a new opportunity.Many résumés are now AI-generated, making it harder for candidates to stand out.AI can assist with interview prep and targeting, but not with authentic connection.Recruiters are overwhelmed by application volume and often avoid posting senior roles.The future of hiring lies in a hybrid model—AI-powered efficiency with human intuition.Suggested TitlesYour Next Job Won’t Be Posted — It’ll Be WhisperedAI, Hidden Roles, and the Human Side of HiringThe Unposted Job Market: Andy Mowat on the Future of Executive RecruitingSound Bites“Companies are overloaded with AI applications.”“Your next role won’t be posted — it’ll be whispered.”“AI is changing recruiting, but relationships still drive outcomes.”Chapters00:00 — Introduction: AI and the future of hiring02:00 — What Whispered is and how it works06:00 — Running lean with AI instead of full-time staff08:30 — The flood of AI-generated applications10:45 — Why most VP and C-level roles are unlisted14:00 — Advice for standing out in the age of AI20:00 — What VC talent teams are missing24:43 — Final thoughts on AI, recruiting, and the road ahead Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Beyond the Honeymoon: How Honeyfund Is Growing Up and Gearing Up with AI🎙️ Sara Margulis on staying scrappy, building a $10M business, and why AI is the next leap for love techEpisode Summary:Sara Margulis founded Honeyfund nearly 20 years ago—before the iPhone, before “crowdfunding” was a thing, and long before AI was on every startup’s roadmap. In this episode, we talk about what it takes to not just launch, but last. From a DIY registry idea to a $10M business, Sara walks us through how Honeyfund stayed relevant, adapted through crisis, and is now integrating AI to serve couples planning their next adventure.We discuss bootstrapping through the early years, the company’s pandemic pivot, lessons in remote leadership, and why Sara calls AI a “competitive necessity”—not a luxury. She also shares what elevator operators can teach us about AI adoption, and what it really means to support couples beyond the honeymoon.Topics Covered:The founding story: From Noe Valley to Fiji to the webThe power of community-funded growth (including a Shark Tank moment)Why mission clarity came after growthHow Honeyfund is training an LLM on two decades of honeymoon dataCompany culture in a fully remote, Gen Z-inclusive teamWhat’s next: anniversaries, baby registries, and beyondKey Quotes:“Honeyfund didn’t even have a mission statement until about three years ago.”“We outlasted Twitter.”“AI isn’t just a competitive advantage. It’s a necessity.”Chapters:00:00 – Introduction and Honeyfund’s early days06:19 – Growth, community, and crowdfunding11:04 – Surviving the pandemic and rethinking the mission17:10 – How AI will shape the next phase of Honeyfund22:05 – Managing a modern team and the future of work26:59 – What’s next for Honeyfund (and why it matters) Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Podcast Title:Venture in the Age of AI: Don Butler on Jobs, Tools, and the Future of VCRefined Description:Don Butler has seen a few cycles. He joined Thomvest Ventures in February 2000—just as the dot-com bubble was about to burst. Now, 25 years later, he’s watching another massive shift take hold: AI.In this episode of The Venture Variety Show, Don and I dive into how artificial intelligence is changing the way venture capital firms operate—from sourcing and diligence to hiring decisions and team structure. We explore the tools Thomvest is using today, how they're thinking about staffing in an AI-first world, and why solo GPs backed by AI assistants might be the new normal.We also talk about the human side of this transformation: what jobs are at risk, where new roles are emerging, and how behavior is already shifting in response to AI-powered systems.If you’re a founder, investor, or just curious how AI is rewiring the VC industry from the inside out, this episode is for you.Key Topics:Why Thomvest no longer hires analystsThe rise of AI agents and what they’re replacingHow generational wealth transfer is transforming wealth managementWhat “AI Associates” mean for firm structure and solo GPsWhy understanding model drift matters in agentic systemsBehavioral surprises from voice agents and what they reveal Get full access to The Venture Lens at theventurelens.substack.com/subscribe

Show Notes – The AI Cognitive Shift: Xiaoyin Qu, heyBossAIGuest: Xiaoyin Qu, founder of heyBossAIHost: Alastair GoldfisherLength: ~30 minutesOriginally recorded for The AI Cognitive Shift (in collaboration with AiNews.com)In this episode:Xiaoyin Qu made headlines by stepping down as CEO of heyBossAI and handing the role to an AI agent named Astra. In this conversation, she shares the thinking behind that bold decision—and what it means for the future of leadership, automation, and trust.We discuss:Why Astra was outperforming human execs on key tasksWhat it’s like to lead a team of AI “employees”How heyBossAI serves customers in 30+ languages—at lightning speedWhy some clients still want the human touch, even in an AI-first companyThe legal and ethical limits of AI in leadership rolesKey Takeaways:Astra builds full websites in minutes—design, backend, copy, SEO, and hostingAI can simplify entrepreneurship by lowering the barrier to launchHuman oversight remains essential for compliance, contracts, and nuanceTransparency tools (like a Slack simulation) help build customer trustThe model raises big questions about the future of work and what leadership looks like in an AI-led orgSound Bites:“AI is the new CEO.”“We are 10x cheaper, 100x faster.”“AI can replace entire teams.” Get full access to The Venture Lens at theventurelens.substack.com/subscribe