What Questions Should Founders Ask VCs? Insights from Jon Bradshaw and Peter Harris

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

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris engage in a thought-provoking discussion about the complexities of founder motivation and the impact of success on entrepreneurial drive. They explore the dynamics between venture capitalists and successful founders, particularly how wealth and achievement can influence a founder's work ethic and commitment to their company.Jon shares insights from conversations with various VCs who express concerns about founders becoming complacent after achieving significant financial success. He questions whether a founder's newfound wealth might lead to distractions, such as excessive travel or lavish spending, which could affect their focus on growing the business. Peter counters this perspective by emphasizing that experienced founders often leverage their networks and knowledge to be more productive, even if they aren't putting in traditional long hours.The hosts delve into real-life examples, including the story of Josh Coats, who returned to leadership after realizing he wanted to set a better example for his children. They discuss how personal motivations can reignite a founder's passion for their company, regardless of their financial status.Throughout the episode, Jon and Peter highlight the importance of maintaining a balance between personal success and professional responsibility. They stress that while it's essential for founders to enjoy their achievements, they must also remain committed to their company's vision and goals. The conversation also touches on the optics of founder behavior in the public eye, discussing how social media presence can influence investor perceptions.Overall, this episode provides valuable insights for both founders and investors on navigating the challenges of motivation and expectations in the venture capital landscape, encouraging a deeper understanding of what drives successful entrepreneurs beyond financial gain.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 the critical question: "Should you raise venture capital funding?" They draw from recent discussions in the entrepreneurial community, where founders often seek advice on fundraising strategies and common pitfalls.Peter shares his perspective on the frequent mistakes founders make when fundraising, particularly focusing on ownership percentage and valuation rather than securing the right amount of capital to reach their next milestones. He emphasizes that many companies raised inflated valuations during the boom years and now struggle to meet expectations, leading to difficult situations like down rounds or flat rounds.Jon adds to the conversation by discussing the psychological aspects of fundraising, including how founders can become overly focused on securing higher valuations rather than considering the long-term health of their business. He highlights the importance of understanding market conditions and being realistic about what is achievable.The hosts explore the implications of raising too much money, which can lead to overspending and a lack of discipline in managing resources. They stress that founders should prioritize finding the right partners who will support their growth journey rather than simply chasing larger checks.Throughout the episode, Jon and Peter provide actionable insights for founders contemplating venture capital, encouraging them to evaluate their business model, market potential, and personal readiness for the demands of rapid growth. They conclude by discussing how not every business is suited for venture backing and that sometimes alternative funding methods may be more appropriate.Overall, this episode offers valuable guidance for entrepreneurs navigating the complex world of venture capital, helping them make informed decisions about pursuing VC funding or exploring other avenues for growth.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 discussion about OpenAI and the implications of its recent $6.6 billion funding round—the largest ever raised by a startup. The hosts explore both the bullish and bearish perspectives surrounding OpenAI’s future, dissecting the competitive landscape and the strategic advantages held by established tech giants like Microsoft.Jon expresses a bearish outlook, arguing that while OpenAI has captured the attention of younger generations, it faces significant challenges from entrenched players with extensive resources and established customer bases. He raises concerns about whether OpenAI can maintain its momentum and become a dominant force akin to Google, suggesting that AI may ultimately become just another feature expected in software products.Conversely, Peter presents a bullish case for OpenAI, highlighting its rapid revenue growth and strong enterprise sales. He points out that the company has successfully positioned itself as synonymous with AI technology, becoming a verb in popular culture. Peter emphasizes that OpenAI's ability to generate substantial revenue quickly is indicative of its potential to thrive in the competitive landscape.Throughout the episode, the hosts engage in a spirited debate about the future of AI, discussing the importance of brand recognition, market positioning, and the challenges of discoverability in an increasingly crowded space. They reflect on how incumbents may leverage their existing customer relationships to dominate the market while considering how OpenAI can navigate these complexities.Overall, this episode provides listeners with an insightful analysis of OpenAI’s current standing and future prospects, offering valuable perspectives for entrepreneurs, investors, and anyone interested in the evolving world of artificial intelligence.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 kick off Season Two with an engaging discussion about their recent activities and reflections on the venture capital landscape. They share insights from their participation in the Founder 100 event in Utah, which celebrated the top 100 founders as voted by their peers. This unique approach fostered a vibrant networking atmosphere, allowing attendees to connect with like-minded entrepreneurs.Jon and Peter discuss the challenges of balancing their busy schedules while organizing impactful events and exploring ideas for future gatherings, including potential activities like racing events to engage the entrepreneurial community. They also touch on the importance of communication and feedback between founders and investors, sharing personal anecdotes about navigating these conversations.The hosts emphasize the significance of graciously receiving feedback as a founder, highlighting that constructive criticism can be invaluable for growth. They also reflect on the complexities of providing actionable feedback to entrepreneurs, discussing how it can influence future interactions and funding opportunities.Throughout the episode, Jon and Peter provide listeners with personal stories, industry insights, and practical advice for founders and investors. This lively conversation sets the tone for an exciting season, promising more valuable discussions on venture capital trends and entrepreneurship.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 "Who are Accredited Investors?" The hosts provide a detailed masterclass on common terminology essential for individuals seeking funding or pursuing a career in venture capital. They begin by defining an accredited investor as someone with a net worth exceeding $1 million, excluding their primary residence, or an individual with an income of over $200,000 individually or $300,000 with a spouse for the past two years.The discussion further explores the criteria for accredited investors, including financial and professional qualifications. The hosts explain that knowledgeable investors in venture capital, private equity, or those holding specific licenses like Series 7 or Series 65 can also qualify. They emphasize the importance of these qualifications in protecting investors and companies from high-risk investments and potential legal issues.Moreover, the episode sheds light on the significance of accredited investor status for companies raising funds, venture capital firms, and private equity funds. It is highlighted that requiring accredited investors provides legal protections for both the companies and the investors, ensuring transparency and safeguarding against potential disputes in the future.The hosts also touch on the practical implications of being an accredited investor, such as the ability to absorb potential losses without significant financial strain. They stress the importance of educating investors on the risks involved in high-risk investments and the need for founders to work with legal counsel to ensure compliance and protection for all parties involved.Overall, this podcast episode offers a comprehensive exploration of accredited investors, their qualifications, and the legal and financial implications for both investors and companies in the venture capital landscape.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