Marketing to Machines: Truth, Trust & AI Shopping

How do you build long-term trust between founders and investors—and what happens when that trust meets the chaos of AI-driven commerce? In this episode, Peter Harris and Jon Bradshaw sit down with Kimberly Shenk, founder & CEO of Novi, and Brian Rothenberg, partner at DeFi VC, to explore:How past working relationships shape investor–founder dynamicsThe art of saying “no” without burning bridgesWhy small brands can outrank giants in AI-powered shoppingThe death (and rebirth) of SEO in the LLM eraReal frameworks for finding product-market fit “Machines care more about truth; humans are easily persuaded.” A high-signal, no-fluff conversation on the future of trust, data, and growth in the age of AI.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

Venture capital isn’t dead — it’s evolving. Carta’s Head of Insights, Peter Walker, joins Jon Bradshaw and Peter Harris to unpack what the data really says about the 2025 market. From the AI-fueled bifurcation to shrinking equity packages and a wave of secondaries, this episode breaks down how founders, VCs, and LPs are adapting in real time.Peter shares Carta’s inside view on:The comeback of deal flow and valuationsWhy down rounds are easing but hiring hasn’t reboundedHow founder dilution and equity norms have shiftedThe rise of liquidity via secondaries and fund-to-fund capitalWhat signals matter most heading into 2026If you care about where venture is heading next — this is the episode.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris are joined by Alex Sen, CEO of Meridian, and Nnamdi Okike, an investor associated with Meridian, to discuss the transformative role of AI and software in private equity and venture capital investing. Alex shares his journey from nearly a decade in private equity, battling with outdated CRM tools, to founding a next-generation AI-powered CRM and deal sourcing platform that streamlines workflows, surfaces proprietary deal opportunities, and enhances decision-making for some of the world's largest firms.Nnamdi provides the investor’s perspective, highlighting their decade-long commitment to leveraging software and data analytics to revolutionize venture operations. They discuss how AI is expanding the total addressable market by automating manual tasks, improving deal sourcing efficiency, and enabling investors to better track, prioritize, and engage with evolving companies. Both guests reflect on the challenges of AI adoption, the changing nature of junior analyst roles, and the importance of human intuition alongside advanced technology.Listeners will gain valuable insights into the evolution of investing software, the competitive shifts AI is catalyzing in the finance industry, and how firms must continuously elevate their capabilities to succeed. The conversation touches on the broader impact of AI on workflow, learning acceleration, and founder-investor relationships, making this episode a must-listen for investors, founders, and anyone curious about the future of AI-enabled investing.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris sit down with Grace Gong, acclaimed VC podcaster, investor, and founder of the Smart AI Conference. Grace shares her inspiring journey from international student to a premier voice in tech and venture, hosting top shows like "Venture with Grace" and "Smart Venture Podcast." She details her mission to unlock access to venture and tech wisdom for those outside the usual networks, highlighting the importance of both online and in-person connections through her rapidly launched San Francisco AI conference.The conversation dives deep into the changing landscape of AI and startup building, from the GPT-driven chatbot era to today's surge in customizable agent tools and "vibe coding." Grace discusses why strong distribution and go-to-market strategy are the real bottlenecks, even as technical barriers fall, and explains the rapid rise of highly specific, domain-focused AI applications. She brings candid, contrarian insights from leading operators and executives, addressing trends in voice AI, workflow automation, the impact of AI on junior talent, and the evolving user experience centered on chat and conversational interfaces.Grace also addresses the risks of overrelying on automation, the future of AI hardware beyond today's wearables, and the vital role of hands-on learning. Her perspective is laced with real stories from her network and her own investments, making this episode a goldmine for founders, operators, and anyone eager to understand how community, execution, and adaptability will shape the next generation of tech companies.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

Join hosts Jon Bradshaw and Peter Harris in a deep dive into the evolving world of AI, autonomy, and the future of transportation with Gabe Klein, former leader of the U.S. Joint Office of Energy and Transportation, and Alexei Andreev, co-founder and managing director at AutoTech Ventures. Gabe brings a wealth of experience from public policy and urban mobility design, while Alexei offers a sharp lens on deep tech investments in autonomous vehicle technology and infrastructure.This episode untangles the complex challenges of achieving full vehicle autonomy, exploring why true self-driving cars remain an elusive goal over a decade after initial excitement. Gabe and Alexei discuss the intricacies of safety definitions, the need for technology that surpasses human driving, and the mathematical challenges posed by unpredictable real-world driving environments.Listeners will gain insights into the current state of autonomous vehicle deployment, including the technological debates over sensor suites like LiDAR versus vision-only systems, and the critical role of liability, insurance, and public perception in shaping adoption. The conversation also highlights promising investment opportunities beyond passenger vehicles—such as off-road agricultural autonomy, logistics automation, and critical supporting infrastructure like vehicle servicing, recharging, and fleet management.With a thoughtful look at cultural differences in safety expectations and the interplay of technology and public policy, this episode is essential for investors, policymakers, entrepreneurs, and anyone interested in the future landscape of mobility and the challenges and opportunities it presents.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this thought-provoking episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris take listeners deep inside the complex financial structures that define modern venture capital. The conversation centers around a critical observation in today’s industry: most VC funds can now be classified as either "2% funds", large, brand-name firms prioritizing substantial management fees, or "20% funds", smaller, more performance-driven firms focused on carry and outsized returns.Peter breaks down the economic incentives behind each type, explaining how mega-funds like Andreessen Horowitz and Sequoia generate enormous management fees just by virtue of their size, while smaller funds must make riskier bets and actively chase exceptional outcomes to realize significant profits. The hosts explore the growing divide between these two models and discuss the challenges founders face in choosing the right VC partner.Jon and Peter debate the strategic trade-offs from a founder's perspective, including:The real benefits (and drawbacks) of working with large, brand-name funds versus smaller, scrappier onesHow the structure of a fund influences VC motivation, founder support, and board involvementThe evolving role of secondary markets, liquidity, and exit strategies for early-stage investorsHow asset manager dynamics and the influx of institutional capital driven by endowments and sovereign wealth funds are reshaping the VC landscapeThey also touch on trends like later-stage company scaling, the boom in private market investments, and the rise of secondary sales as an alternative to waiting for an IPO. Throughout the discussion, Jon and Peter offer candid insights and personal anecdotes, revealing the sometimes unseen incentives that drive behavior in venture capital.This episode is essential listening for founders weighing their funding options, as well as anyone curious about the changing face of the venture capital ecosystem.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this compelling episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris engage with Stephanie Palmeri, partner at NextView Ventures, and Caleb Hicks, founder and CEO of School AI, to explore the transformative power of AI in education. Caleb, a former middle school teacher and educational innovator, shares his vision for using AI to create personalized, empathetic learning experiences that address the unique needs of every student, while restoring meaningful human connections in classrooms.Stephanie brings over a decade of experience investing in edtech startups, highlighting the evolution of education technology from the early mobile and tablet era to today's AI-driven wave. She discusses the opportunity for AI to revolutionize both K-12 and higher education, especially in areas like personalized learning, student engagement, and workforce upskilling.Together, they unpack the challenges schools face today, from managing large classrooms and diverse student needs to addressing AI-related concerns like cheating, student privacy, and equity in access. The conversation delves into how AI can be an empowering tool rather than a disruptive force, serving as a tutor, coach, and assistant that enhances critical thinking and individualized instruction.Listeners will gain unique perspectives on why now is the pivotal moment for AI in education, the significant market opportunity in a trillion-dollar industry, and the future of edtech innovation that balances technology with the essential human element of teaching and learning. This episode is essential for educators, founders, investors, and anyone passionate about the future of education.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this insightful episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris are joined by Tiya Gordon, co-founder and CEO of It’s Electric, and Olaf Sakkers, managing partner at Red Blue Capital. Together, they explore the rapidly evolving electric vehicle (EV) landscape, shedding light on market dynamics, industry challenges, and transformative opportunities shaping the future of mobility and energy.Tiya shares her experience leading a Brooklyn-based startup that delivers curbside EV chargers, providing innovative solutions to overcome infrastructure barriers and enable wider EV adoption, especially in urban environments. She highlights the critical need for accessible charging infrastructure, urban-centric solutions, and the potential for bidirectional energy flows that turn EVs into mobile energy storage units supporting city grids.Olaf, a seasoned investor with deep expertise in mobility, logistics, and energy transition, offers a global perspective on EV market shifts. He discusses China’s dominance in EV manufacturing, the complex political and economic factors impacting U.S. EV adoption, and the broader vision of transforming transportation beyond passenger vehicles, emphasizing heavy-duty EV trucks and micromobility solutions as key areas of innovation.The conversation delves into the cultural, regulatory, and infrastructural hurdles slowing EV adoption in the U.S., including tariff impacts, urban planning challenges, and entrenched interests favoring traditional car ownership. Tiya and Olaf discuss promising opportunities for founders and investors, from scalable last-mile delivery electrification to innovative micromobility and multi-modal electric transit solutions.Listeners will gain a nuanced understanding of the intersection between technology, policy, infrastructure, and consumer behavior in the EV ecosystem, along with actionable insights on where meaningful innovation and impact can happen next. Whether you’re an entrepreneur, investor, or EV enthusiast, this episode offers a candid, comprehensive look at powering the future of sustainable transportation.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this compelling episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris welcome Matt Curtolo, an experienced private markets investor and advisor, and Joseph Alalou, co-founder and general partner of Daring Ventures. Together, they dive into the evolving landscape of emerging managers and micro venture funds, offering firsthand perspectives on how smaller funds are carving a niche in today’s competitive venture ecosystem.Matt shares his journey through two decades of managing billions across venture, private equity, and real estate, and discusses how emerging managers can sharpen their strategy, positioning, and fundraising efforts to succeed in a crowded market. Joseph brings a unique and inspiring story from washing cars and community college to leading a VC fund focused on diverse, underdog founders with domain expertise and conviction bias.The conversation explores the definition and dynamics of micro VCs, the importance of authenticity and understanding one’s “right to win,” and how these smaller funds differentiate themselves by moving beyond consensus deals to uncover unique alpha-generating opportunities. They discuss the challenges of fundraising in today’s environment, including the long timelines, the critical role of operational rigor, and how early closings can build momentum and market credibility.Matt and Joseph also tackle how AI is reshaping fundraising and fund operations, emphasizing that technology is a critical tool but human intuition, relationships, and expertise remain irreplaceable. They reflect on the maturation of the venture ecosystem, the growing interest from large funds in emerging managers, and the fundamentally relational nature of VC investing.Listeners will gain practical advice and encouragement on navigating the complexities of emerging fund management, fundraising strategy, and embracing the future of venture capital amid rapid technological change. This episode is essential for aspiring fund managers, limited partners, and anyone interested in the future of micro VC and emerging manager innovation.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of the Venture Capital Podcast, host Peter Harris sits down with Rex Salisbury, solo GP of Cambrian and former fintech partner at Andreessen Horowitz, for an in-depth conversation about the ongoing transformation of financial services. Rex shares his unique journey from investment banking to leading one of fintech’s most dynamic pre-seed and seed funds, explaining how decades of inefficiency in banking have finally given way to a wave of disruptive innovation.The discussion explores recent shifts in the fintech landscape, highlighting how new fintech companies, once dismissed as serving only niche or low-value customers, are now directly competing with and winning market share from the largest legacy banks. Rex points to the rise of digital-first platforms like Robinhood and Wealthfront, which started by serving overlooked users but have evolved into sophisticated competitors for the millennial and Gen Z wealth transfer.Peter and Rex examine why B2B fintech is an especially powerful force, with vertical software companies like Toast integrating lending, payroll, and banking into a single platform that businesses can’t imagine leaving for traditional banks. Rex also tackles the myth of banks’ cost-of-capital advantage, arguing that technology and changing consumer expectations are steadily eroding long-held bank moats.Beyond consumer trends, the episode ventures into the investment landscape, with Rex sharing lessons from recent Cambrian investments, such as companies revolutionizing transfer agents and simplifying business shutdowns. The conversation also addresses the role of crypto and stablecoins in reshaping payment and banking infrastructure, where Rex differentiates between international and U.S. use cases but remains optimistic about crypto’s role as a catalyst for industry change.Rex closes with actionable advice for aspiring founders and operators: seek out dense talent networks, work in growth-stage companies, and always surround yourself with people who teach you. The episode captures the underlying message that, as technology, business models, and capital flows shift, fintech is only just beginning to threaten incumbents and capture its share of the financial future.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812