Key insights

• Fundraising Advice and Objectives Alignment

  • 💸 Sell between twenty and thirty percent of your company over time through fundraising rounds
  • 🤝 Importance of warm intros to VCs, but cold intros also considered by some seed firms
  • ♀️ Gender bias in funding; women-founded companies tend to be underestimated by investors
  • 📈 Advice on aligning objectives with investors for companies in price-sensitive markets

• Startup Characteristics and Investor Selection

  • 🚀 Successful startups often had co-founders and were founded by individuals in their 30s with prior work experience
  • 💡 Non-traditional founders can showcase their hustle, insight, and problem-solving skills at the seed stage
  • 💼 Venture capital industry has been heavily concentrated in certain pools, but it's a great time to be a non-traditional founder
  • 🔍 Choosing investors involves reference checks and rational assessment of the market and dilution
  • 🦄 The term 'unicorn' to describe companies worth over a billion dollars, emphasizing the rarity and magic of such success

• Inclusion, Diversity, and Pitching

  • 🌐 Change.org offers a founder commitment to inclusion and diversity
  • ⏰ Office hours and matching services for female founders and people of color in venture business
  • 📊 Fundamental elements of a pitch include team, problem, product, competitive landscape, financial plan, and summary slide
  • 🦄 Origin of the term “hated unicorn” and analysis of venture capital fund data

• Challenges in Venture Fundraising

  • 📉 The challenges of fundraising for a venture fund, including gender bias and the need for lead qualification
  • ❤️ The importance of empathy in investor-founder relationships
  • 🎯 Efforts to address gender bias and promote diversity in the tech ecosystem through organizations like All Raise

• Fundraising and Investor Dynamics

  • 📈 Fundraising is a skill that requires practice and feedback
  • 💰 Professional investors have specific return expectations and founders need to understand their math
  • 👼 Angels may not provide the guidance needed for scaling a company
  • 🔑 Being prepared and having choices is crucial in fundraising

• Venture Investor Insights

  • 🤝 Venture investors need to be empathetic and optimistic
  • 🔄 Moving to earlier stages of investment means working with raw, less figured out situations
  • 🌱 Believing in people's potential for growth and second chances is essential
  • ⚖️ There's a balance between being a mercenary and a missionary in tech
  • 🔍 Choosing the right investor depends on the kind of support the startup needs
  • 📖 Storytelling is crucial for emotionally engaging investors during fundraising

• CEO Experience and Challenges

  • 👥 Challenges faced as a CEO including managing people and hiring
  • 🌱 Significance of long-term thinking and attracting the right people as a leader
  • 💰 Sales lead qualification and sustainable customer relationships
  • 📈 The role of investors in evaluating short-term and long-term potential
  • ❤️ Importance of empathy and support for founders

• Aileen Lee's Journey

  • ⭐ Aileen Lee's background as a first-generation immigrant and her journey to becoming the founder of Cowboy Ventures
  • 🌍 Her interest in consumer brands and the impact of her traditional upbringing on her career choices
  • 📚 Her experiences working at Gap and Kleiner Perkins, including reading and evaluating business plans at the latter
  • 💼 The significance of gaining operating experience as a venture capital advisor, including becoming a CEO to better understand and advise startup CEOs

Q&A

• What advice was provided for fundraising and aligning objectives with investors?

  Advice was given on fundraising, warm intros to VCs, gender bias, and aligning objectives with investors, emphasizing the importance of the VC and founder relationship for successful fundraising.

• What are the components of a successful pitch, and what is the term 'hated unicorn' about?

  The components of a pitch include team, problem, product, competitive landscape, financial plan, and a summary slide. The term 'hated unicorn' was introduced, along with the analysis of venture capital fund data.

• How does the venture capital industry address gender bias and promote diversity?

  The challenges of fundraising for a venture fund, including gender bias and the importance of empathy in investor-founder relationships, are being addressed by organizations like All Raise, which works to accelerate success for women in the tech ecosystem.

• What skills are required for successful fundraising, and what challenges exist for non-traditional founders?

  Fundraising requires skills like practice, feedback, understanding investor expectations, and being prepared. Challenges for non-traditional founders include biases, but it's a great time to be one, supported by initiatives for inclusion and diversity in entrepreneurship.

• What is the significance of empathy and storytelling for venture investors?

  Venture investors need to be empathetic, optimistic, and utilize storytelling for emotionally engaging fundraising. Believing in people's potential for growth, choosing the right investor, and addressing raw, less figured out situations are also essential.

• What are the key characteristics of successful startups?

  Successful startups often had co-founders, were founded by individuals in their 30s with prior work experience, and were based on personal relationships. Non-traditional founders can showcase their hustle, insight, and problem-solving skills at the seed stage.

• What are the challenges faced as a CEO, and what important aspects were emphasized?

  Challenges as a CEO included managing people, hiring, sales, and dealing with investors. The speaker emphasized the significance of empathy, long-term thinking, employee management, sales lead qualification, and sustainable customer relationships.

• What were Aileen Lee's experiences at Gap and Kleiner Perkins?

  At Kleiner Perkins, Aileen Lee read and evaluated business plans, and later gained operating experience, including becoming a CEO, which helped her understand and advise startup CEOs. At Gap, she had varied career experiences.

• What is Aileen Lee's background and journey to founding Cowboy Ventures?

  Aileen Lee is a first-generation immigrant who later founded Cowboy Ventures. Her traditional upbringing influenced her interest in consumer brands and her career choices, which led to her working at Gap and Kleiner Perkins before founding Cowboy Ventures.

• 00:00 Aileen Lee shares her journey from being a first-generation immigrant to founding Cowboy Ventures, her varied career experiences, including working at Gap and Kleiner Perkins, and the importance of gaining operating experience as a venture capital advisor.
• 07:45 The speaker discusses their experience as a startup CEO, addressing challenges such as managing people, hiring, sales, dealing with investors, and the importance of empathy. They emphasize the significance of long-term thinking, employee management, sales lead qualification, sustainable customer relationships, and the role of investors in evaluating not just short-term but long-term potential.
• 14:37 Venture investors need to be empathetic and optimistic, and storytelling is crucial for fundraising.
• 21:52 Fundraising is a skill that requires practice and feedback. Professional investors have specific return expectations and founders need to understand their math. Angels may not provide the guidance needed for scaling a company. Being prepared and having choices is crucial in fundraising.
• 29:13 The challenges of fundraising for a venture fund, including gender bias, the need for lead qualification, and the importance of empathy in investor-founder relationships. All Raise is a non-profit working to accelerate success for women in the tech ecosystem.
• 35:58 The speaker discusses initiatives for inclusion and diversity in entrepreneurship, the components of a pitch, the term “hated unicorn”, and the analysis of venture capital fund performance.
• 42:38 The speaker analyzed the characteristics of successful startups and found that many had co-founders, were founded by individuals in their 30s, and were based on personal relationships or previous work experience. They also discussed the challenges faced by non-traditional founders and the process of choosing investors.
• 51:10 Advice on fundraising, warm intros to VCs, gender bias in funding, and aligning objectives with investors. VC and founder relationship is crucial for successful fundraising.