Creators, AI, and the Future of Content: A Conversation with Tim Holladay and Peter Hollens

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris reflect on key lessons from recent interviews with entrepreneurs, medical innovators, and content creators, turning their focus inward for a wide-ranging discussion on the evolving role of influencers, authenticity, and attention in today’s business world.Jon and Peter kick off by revisiting the intersection of health technology and consumer empowerment, discussing the surge in wearables, at-home diagnostics, and consumer-led health journeys. They probe why younger generations are more invested in their health, attributing this trend to social visibility, the desire for authenticity in a digital age, and the rapid acceptance of medical advances, such as GLP-1 treatments for weight loss.The conversation shifts dynamically to the creator economy, exploring how the most effective marketing and brand-building today often comes from content creators and influencers with passionate, loyal audiences. Peter highlights the unique value these creators bring, citing the example of a tech startup that attributes much of its rapid growth to a co-founder’s expertise in cultivating online engagement, rather than traditional marketing.Jon and Peter debate whether every CEO now needs to be a content creator and ponder the future of influencer-led businesses. They analyze the success of influencer-driven brands like Hailey Bieber’s, dissecting how authentic involvement can drive enormous margins and corporate valuation, while also questioning the long-term challenges when founders sell to larger corporations.They conclude with practical insights for founders: thoughtfully consider influencer involvement as part of founding teams, seek authenticity over mere endorsements, and recognize that in a noisy digital world, capturing and sustaining attention may be the single most valuable asset for any business.This episode offers a forward-looking perspective on how authenticity, strategic influencer partnerships, and the ability to cut through digital noise are reshaping not just marketing but the very foundations of building and scaling a modern brand.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 forward-thinking episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris are joined by two leaders shaping the future of healthcare: Ryan Morley, Partner at Springside, and Dr. Jon Lensing, co-founder and CEO of Open Loop. Together, they dive deep into the rapidly evolving landscape of telehealth and digital health, exploring how technology, AI, and new business models are transforming care delivery.Dr. Lensing shares his journey from rural medicine to building Open Loop, a telehealth infrastructure company designed to bring healthcare directly to where people live, work, and play. He explains how Open Loop is enabling non-traditional platforms—like gyms, dating apps, and retail stores—to offer convenient, on-demand healthcare services, fundamentally shifting care from hospitals and clinics to everyday environments.Ryan Morley and Peter Harris discuss the investment opportunities emerging from this shift, highlighting how the COVID-19 pandemic accelerated telehealth adoption and how the next wave of innovation will focus on infrastructure, personalization, and value-based care. The conversation explores the power of AI in healthcare, from automating clinical documentation and patient intake to improving diagnoses and care coordination. Dr. Lensing details how Open Loop leverages AI to drastically reduce clinician workload and enhance patient engagement, while Ryan emphasizes the need for regulatory evolution to unlock the full potential of autonomous and AI-driven care.The group also examines the broader determinants of health, noting that 85% of health outcomes are tied to lifestyle and environment rather than traditional medical care. They discuss how digital health can proactively address chronic disease, expand access, and empower consumers to take charge of their well-being.Packed with insights on infrastructure, investment trends, regulatory hurdles, and the promise of AI, this episode is a must-listen for founders, investors, and anyone interested in the future of healthcare.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://x.com/VCPodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/YouTube: https://www.youtube.com/@VentureCapitalfmSpotify: 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 dynamic episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris are joined by Tim Holladay, investor and co-founder of Space Station Investments, and Peter Hollens, renowned vocalist and innovative content creator. Together, they explore the evolving intersection of content creation, AI, and investment in the digital age.The conversation kicks off with Peter Hollens sharing his unique perspective as both a world-class musician and a forward-thinking entrepreneur deeply engaged with AI’s impact on creativity. Tim Holladay highlights their collaborative investment approach, focusing on early-stage consumer companies and the growing role of creators in startup ecosystems.Jon and Peter dive into the challenges and opportunities AI presents for content creators, from accelerating production to the flood of AI-generated content saturating digital platforms. Peter Hollens discusses how authentic human connection and parasocial relationships remain invaluable even as AI blurs the lines between human and machine-generated content. He shares fascinating examples of using AI tools to enhance creativity and even assist his autistic child, illustrating AI’s potential beyond entertainment.The episode also tackles the evolving landscape of influencer marketing, the value creators bring as low-cost, high-ROI partners, and the shifting dynamics between brands and digital creators versus traditional influencers. The hosts and guests debate how AI-driven content might reshape attention economies, audience engagement, and the future of long-form versus short-form content.Throughout the lively discussion, Peter Hollens recounts his challenging experience addressing AI skepticism at a recent commencement speech, underscoring the cultural divide around AI adoption. Tim and the hosts reflect on how investors and creators alike must embrace AI tools to stay ahead in a rapidly changing environment.This episode offers a rich, nuanced exploration of how AI is transforming content creation, investment, and the creator economy, providing valuable insights for founders, investors, creators, and anyone curious about the future of digital media.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 Max Marchione, CEO and co-founder of Superpower.com, and Dr. John Dayton, MD, MBA, a healthcare innovator and venture partner. Together, they explore the evolving landscape of health technology and data intelligence, focusing on how cutting-edge biomarker analysis and AI-driven insights are reshaping disease prevention and personalized care.Max shares his vision of building a healthcare system centered on enhancing human capability and longevity, emphasizing the shift from reactive treatment to proactive prevention. Dr. Dayton brings his frontline experience as an emergency physician and Stanford faculty member to discuss the current challenges in healthcare, including fragmented data systems and the need for interoperability to enable comprehensive, predictive care.The conversation dives deep into the limitations of traditional single biomarker approaches and the promise of aggregating multiple data points into comprehensive health scores, like the Superpower Score. They discuss the critical role of omics data, continuous wearable monitoring, and multimodal AI in advancing personalized medicine. Dr. Dayton highlights the importance of integrating clinical data with remote patient monitoring to improve patient outcomes and reduce hospitalizations.Throughout the episode, the guests and hosts examine the barriers to adopting these innovations within existing healthcare reimbursement models and the potential for value-based care to drive systemic change. This episode offers a forward-thinking perspective on how technology, data, and innovation converge to create a more effective, patient-centered healthcare 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

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris analyze how recent government policy shifts and economic changes are influencing the venture capital landscape and broader economy. They discuss the effects of tariffs, government spending, and regulatory uncertainty on startups and investors, highlighting concerns from founders and VCs alike about how these factors impact funding availability and business operations.Jon and Peter explore the challenges faced by companies reliant on government contracts and grants, noting how freezes and delays can threaten runway and survival. They also examine the broader fiscal picture, including rising national debt, the potential consequences of inflation and tax hikes, and the complex balancing act governments face in cutting spending without triggering recession.The conversation touches on real-world examples, such as illustrating how radical change can sometimes be necessary to drive growth amid adversity. The hosts debate the need for significant budget cuts versus gradual reductions and discuss the antiquated state of government technology and defense spending, considering opportunities for modernization and efficiency.Finally, Jon and Peter share their predictions for the year ahead, weighing the short-term impacts of tariffs and the likelihood of economic downturns against the resilience of the market and potential for innovation. This episode offers a nuanced perspective on how government actions ripple through the venture capital ecosystem and what founders and investors can expect in a shifting economic environment.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 dive into one of the most critical yet often overlooked topics for startup founders: the questions you should be asking venture capitalists before taking their money. Drawing on their extensive experience, Jon and Peter discuss common pitfalls that founders face when negotiating deals, including the hidden terms in contracts that can come back to haunt a company years later.The hosts stress the importance of doing deep due diligence on potential investors—not just their financial terms, but their character and how they handle failure. They emphasize asking tough questions about how a VC firm supports struggling portfolio companies and their philosophy on valuation and terms. Jon and Peter also reflect on the delicate balance founders must strike in pushing back while maintaining a constructive relationship.Listeners will gain valuable insight into the realities of venture capital beyond the pitch room—the importance of understanding who is investing in your company, how VCs behave when things go wrong, and how to spot red flags early. This episode is an essential guide for founders preparing to raise capital and aiming to build a strong, lasting partnership with investors.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 delve into the complex world of valuations, exploring both the theoretical foundations and the practical realities faced by entrepreneurs and venture capitalists. Peter begins by discussing the fundamental principles of valuation, using the metaphor of a "Golden Goose" to illustrate how discounted cash flow models are used to estimate a company's worth based on future cash flows.The conversation shifts to the venture capital landscape, where Peter notes that traditional valuation methods often don't apply due to the high-risk nature of early-stage startups. He emphasizes that while these models provide a theoretical framework, the actual process of valuation in venture capital is heavily influenced by negotiation and market dynamics.Jon counters with a more pragmatic view, suggesting that valuations are often inflated and less relevant than other terms in a deal. He shares examples of companies being valued at significantly higher amounts than their true worth, highlighting how VCs may use these valuations to secure favorable terms.Throughout the episode, the hosts discuss how the market has evolved, with valuations increasing dramatically over the past decade. They reflect on past deals, noting that what was once considered acceptable is now viewed as predatory, illustrating the shift in market norms and expectations.The conversation concludes with insights into the challenges of raising capital, emphasizing that sophisticated entrepreneurs are better equipped to navigate complex deals and avoid unfavorable terms. Overall, this episode provides a nuanced exploration of valuations from both the VC and founder's perspective, offering valuable insights into the art and science of negotiating value in the venture capital world.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 tackle a crucial transition point for early-stage startups: making those first key hires. The discussion is sparked by a founder seeking advice on how to shift from simply building a product with a small team to building a structured company with employees.Peter recounts his conversation with the founder and the resources he recommended: the books "Buy Back Your Time" and "Who Not How." The conversation emphasizes the importance of valuing a founder's time and creating mechanisms for delegation and self-management as the team grows. Jon and Peter then debate the founder's sentiment that "hiring is evil," considering the financial strain and potential pitfalls of premature scaling.The hosts delve into actionable strategies for making smart hiring decisions. Jon shares his philosophy of hiring only when absolutely necessary and prioritizing individuals with whom you've previously worked. He also describes a method for quantifying the potential value of new hires by assessing the opportunity cost of current challenges. Peter discusses balancing founder-led efforts with building a functional team, including strategies for incentivizing tactical execution over strategic planning.The episode covers tactics for identifying generalists versus specialists, the importance of clear communication and expectations, and alternative approaches like "hiring twice" to create a competitive environment. It also addresses the challenges of transitioning from founder-led sales to a structured sales organization, emphasizing the importance of finding individuals who can perform at 70% of the founder's level.Overall, this episode provides founders with valuable insights and practical advice on navigating the complexities of early-stage hiring, offering guidance on building a strong team while avoiding common pitfalls.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 make their predictions for the venture capital landscape in 2025. The conversation kicks off with a discussion about the current wave of AI-focused startups, with both hosts agreeing that many of these companies, particularly those building "AI wrappers" without unique data sets, will face challenges as larger players and incumbents integrate AI into their existing products and services. Jon predicts a "burned over land" scenario for many of these startups.The hosts then shift to a discussion about the potential impact of political changes on the M&A market. Jon predicts that Lina Khan will leave the FTC, leading to a more open M&A environment and increased liquidity. Peter expresses cautious optimism, suggesting that while a change in administration could ease antitrust scrutiny, other factors may still play a role. They explore the potential for large tech companies like Meta and those aligned with AWS and Google Cloud to make significant acquisitions.The conversation also touches on the IPO market, with both hosts anticipating increased activity in the coming years. Jon believes it will take longer for the IPO market to warm up, influenced by the upcoming election and the time required for companies to prepare for an IPO. Peter anticipates a faster turnaround, expecting increased liquidity and confidence to drive more deals.They also discuss the trend of VCs striving to add value beyond simply writing a check, with Jon skeptical of VCs offering outdated advice. Peter acknowledges this pitfall but defends the value of guidance from VCs in areas such as valuation and fundraising strategy. The episode concludes with an assessment of the challenges startups will face in raising capital and the potential for differentiation through specialization and strategic alliances.Overall, this episode provides a thought-provoking glimpse into the future of venture capital, offering insights for both founders and investors navigating a rapidly evolving market.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 engage in a lively debate about the current state of AI investments and the implications for startups in the tech space. They kick off the discussion by analyzing recent statistics indicating that 31% of all assets are now categorized as AI investments, prompting Jon to express skepticism about the sustainability of many AI-focused startups.Jon argues that many companies labeled "AI companies" may struggle to differentiate themselves in a crowded market, suggesting that AI is often seen as an add-on feature rather than a standalone product. He contrasts this perspective with Peter's view that AI represents a transformative wave similar to past technological advancements, such as mobile technology. Peter asserts that companies built with an AI-first approach may have a competitive advantage over traditional firms that merely integrate AI into their existing products.The hosts explore various examples, discussing how incumbents like Zendesk could leverage their established customer bases to implement AI solutions more effectively than new entrants can gain market share. They also consider the broader implications of AI on product development costs and customer acquisition strategies, highlighting the evolving landscape where discoverability becomes increasingly challenging as more applications emerge.Throughout the episode, Jon and Peter provide valuable insights into the opportunities and challenges facing founders in the AI space, encouraging listeners to think critically about their business models and the potential for disruption in a rapidly changing environment. This episode serves as a thought-provoking exploration of the future of AI investments and what it means for entrepreneurs navigating this dynamic market.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