20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc...
The Twenty Minute VC (20VC)Full Title
20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
Summary
This episode features an interview with Harry Stebbings by Simon Squibb, where Stebbings shares his journey in building 20VC, including fundraising for a $400 million fund and strategies for cold outreach.
Key takeaways focus on lessons learned from successful entrepreneurs regarding persistence, sales, personal branding, and overcoming failure, emphasizing the importance of taking the first step and continuous effort.
Key Points
- Early fundraising success was achieved by a 19-year-old Stebbings by creating a sense of FOMO and directly appealing to the procurement budgets of CEOs, demonstrating the effectiveness of understanding buyer psychology.
- Effective cold outreach relies on personalization, attention to detail, and leveraging social proof, such as mentioning previous high-profile interviews to build credibility and encourage engagement.
- Building genuine relationships, particularly moving conversations off email to platforms like WhatsApp, is crucial for fostering trust and personal connection, which often facilitates business outcomes.
- The importance of persistence is highlighted by Stebbings' 53 cold emails to Marc Benioff, underscoring that continuous effort, combined with personalization, can eventually lead to desired outcomes.
- Starting young is advantageous for entrepreneurs due to the ability to take more risks and the development of stamina and naivete, which can be leveraged for ambitious pursuits.
- A positive mindset and visualization are critical for success, especially in overcoming the inherent negativity and skepticism that can hinder progress in some cultures, like the UK.
- Embracing failure as a learning opportunity is essential, as perceived failures can often lead to unforeseen successes and valuable life lessons, emphasizing the individual's agency in turning setbacks into progress.
- Content creation is a powerful tool for building relationships and distribution, enabling individuals to establish a personal brand and pre-sell to potential collaborators or clients.
- The most challenging and impactful million to make is the first one, as it unlocks further financial opportunities and highlights the world's tendency to favor those who already have wealth.
- The ultimate barrier to business success is shifting from technology to communication, sales, and distribution, as these skills enable one to reach and influence a wider audience.
- Focusing on iterating and improving existing models, rather than solely seeking novel ideas, can lead to significant business success, as exemplified by reinventing the VC model with a media-centric approach.
- Breaking down ambitious visions into smaller, achievable milestones is key to maintaining momentum and avoiding overwhelm, turning daunting long-term goals into a series of manageable steps.
- The most effective way to influence others is by gaining the approval of their close connections, such as best friends or partners, as their opinions can significantly sway decision-making.
- Treating everyone with politeness and respect, regardless of their perceived status, is crucial, as you never know who might hold significant influence or connections.
- The core of happiness can be found in simple, meaningful moments and relationships, rather than solely in accumulating wealth, reinforcing the importance of a balanced perspective.
- To achieve success, one must be willing to work relentlessly and consistently, understanding that true commitment goes beyond mere desire and involves embracing the demanding nature of the pursuit.
Conclusion
Persistence, personalized outreach, and relationship-building are critical for success in sales and networking.
Embrace failure as a learning opportunity and maintain a positive mindset to overcome challenges and achieve ambitious goals.
Focus on creating genuine connections, leveraging distribution, and continuously iterating on ideas to build a sustainable and impactful business.
Discussion Topics
- What is the most effective strategy for cold outreach in today's crowded digital landscape?
- How can individuals cultivate a more positive and proactive mindset to overcome personal and professional challenges?
- Beyond traditional metrics, what are the most important indicators of true success in entrepreneurship and life?
Key Terms
- Cold Emails
- Unsolicited emails sent to potential clients or contacts with the goal of initiating a business relationship or sale.
- FOMO (Fear Of Missing Out)
- A feeling of anxiety that an exciting or interesting event may currently be happening elsewhere, often aroused by posts seen on social media.
- Social Validity
- The concept that people are more likely to accept a belief or behavior if they see that many other people also accept it.
- Flywheel
- A concept in business where continuous effort builds momentum, leading to accelerating growth and success over time.
- Agentic Finance
- A type of financial management that leverages artificial intelligence to automate and optimize financial processes, giving businesses more agency.
- Procurement Budget
- The amount of money allocated by an organization for purchasing goods or services.
- Shadow Work
- Unpaid, invisible labor that is essential for the functioning of society but is not recognized as work or compensated.
Timeline
Harry Stebbings details how, at 19, he secured $1 million in sponsorships by creating a sense of scarcity and targeting CEO procurement budgets.
Stebbings explains the importance of personalization and relationship-building in cold outreach, citing his use of P.S. notes about favorite whiskeys.
Stebbings discusses his strategy for interviewing 107 billionaires, emphasizing short, concise, and personalized cold emails, using social validity as a key tool.
Stebbings recounts raising $70 million through WhatsApp by building relationships and moving conversations off email.
Simon Squibb reflects on his early days, noting that success takes years of hard work and encouraging listeners to take the first step.
Stebbings explains how he leveraged ego and insecurity to make money at a young age.
Stebbings emphasizes the difficulty of making the first million and how it unlocks further opportunities due to the inherent unfairness of the world.
Stebbings advises chasing the first million due to its power and highlights the advantage of starting young to take more risks.
Stebbings criticizes the UK's negative outlook and advocates for positive visualization.
Stebbings discusses Project Europe, a fund aimed at enabling young people to pursue ambitious goals, and criticizes UK's snootiness towards unconventional career paths.
Stebbings shares how his biggest failures, like being kicked out of boarding school, led to his biggest successes.
Stebbings attributes his ability to turn negatives into positives to having a mentor and the "ability to end the day."
Stebbings reflects on the 19-year-old story, emphasizing the importance of starting young and taking the first step, as activity drives outcomes.
Stebbings admits he was a terrible interviewer at the start, but emphasizes that improvement comes from repeated practice.
Stebbings highlights that failure often stems from a lack of care, and if no one cares, your failure remains unknown.
Stebbings identifies communication, sales, and marketing/distribution as the most critical skills in the modern business landscape.
Stebbings shares an example of a company, Fixer, generating $4 million in revenue from a single LinkedIn post, showcasing the power of distribution.
Stebbings discusses the shift towards creators becoming platforms and the logic of promoting one's own brand over others.
Stebbings outlines the first lesson from billionaires: never accept "no" for an answer.
Stebbings shares the second lesson: continuously beat down the door, illustrated by his 53 emails to Mark Benioff.
The discussion touches upon advanced sales strategies like influencing personal trainers or assistants.
Stebbings emphasizes the importance of thinking about the next step in content strategy, using viral Twitter posts as an example of leveraging social proof.
Stebbings reiterates that starting is crucial, even if you're not charismatic or skilled initially, as 99% of people never begin.
Stebbings discusses how people often use their ability to predict the future to foresee failure, hindering action.
Stebbings reflects on the evolution of his content strategy, from typical business advice to street interviews asking "What's Your Dream Now?".
Stebbings advises hiring someone quickly to create accountability and emphasizes the need to "burn the boats" to force action.
Stebbings shares a framework for tough decisions: asking "What would [respected person] do?".
Stebbings contrasts the desire for money with the happiness it brings, sharing a personal anecdote about feeling lonely despite being a millionaire.
Stebbings emphasizes identifying what truly makes you happy, citing simple moments like walking with his mother.
Stebbings highlights the importance of having a central "happy place" or core value to ground oneself during the challenges of building a business.
Stebbings discusses how mentorship can be found by following the content of admired individuals, rather than requiring direct one-on-one interaction.
Stebbings draws a parallel between mentorship and dating, suggesting that working on oneself makes one a more desirable mentee.
Stebbings proposes a "hack" for balancing life's demands by integrating activities, such as working out with friends or having family members on the team.
Stebbings advocates for reinventing existing concepts rather than solely seeking entirely new ideas, citing his own approach to the VC model.
Stebbings stresses the need for creative content hooks and continuous iteration, rather than just copying existing successful formats.
Stebbings advises breaking down overly ambitious visions into smaller, achievable goals to maintain motivation.
Stebbings discusses the seventh lesson: making the best friend like you, referencing the movie "Hitch" and the power of influential third parties.
Stebbings shares an anecdote about treating everyone with kindness, leading to unexpected connections and opportunities.
Stebbings suggests that increasing personal happiness involves learning the names of people you interact with frequently.
The episode concludes with discussions of sponsors like Perk, Daily Body Coach, and Airwallets.
Episode Details
- Podcast
- The Twenty Minute VC (20VC)
- Episode
- 20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
- Official Link
- https://www.thetwentyminutevc.com/
- Published
- January 24, 2026