20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital
Mar 10, 2025
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Jake Saper, General Partner at Emergence Capital, discusses his firm's impressive track record of investing $2BN and returning $8BN. He shares insights about their early investment in Zoom and the critical importance of market dynamics over mere traction. Saper also delves into the changing landscape of SaaS metrics and the significance of retaining customers. He highlights the existential concerns around AI and encourages companies to aim for becoming board discussion topics, all while revealing lessons learned from their early sale of Salesforce.
Jake Saper emphasizes the importance of aligning investment strategies with genuine market needs and operational realities to ensure startup success.
The podcast discusses the necessity of supporting founders with a robust enterprise sales model to foster long-term growth and operational stability.
Market demand remains a crucial component, especially for startups in AI and tech, ensuring relevance through immediate and pressing solutions.
The conversation highlights that nimble startups can outperform larger incumbents by focusing on specific market segments with tailored innovations.
Deep dives
Investment Returns and DPI Performance
The venture firm discussed deploying nearly $2 billion in capital, which has returned over $8 billion in cash, translating to a staggering 16 times DPI (distributions to paid-in). This fund, often referred to as fund three, includes notable successes such as Zoom. The analysis on the firm's investments reveals that 90% of the deals have raised subsequent financing rounds successfully, indicating a strong performance against market benchmarks. Furthermore, one out of every five investments has surpassed billion-dollar rounds, showcasing significant growth potential within their portfolio.
Zoom's Unique Proposition
Zoom was identified as an early investment opportunity based on the realization of replacing WebEx, which was considered outdated. The investment team was drawn to Zoom not only because of its rapid revenue growth but also due to its technological superiority, with the founder having prior experience at WebEx. Leading due diligence on Zoom presented challenges, notably due to the high check size and early stage of the company, requiring careful financial modeling. Despite the risks, the team believed in Zoom's long-term potential based on these differentiating factors.
The Importance of Founder Insight
A crucial takeaway from discussions is that founder insight is vital in identifying successful investments. The podcast stressed the necessity of finding founders who both understand their market and possess the capability to pivot and implement enterprise-grade solutions effectively. The example of Zoom illustrates how the VC's readiness to support the founder in establishing a robust enterprise sales model was instrumental to its success. This highlights the need for venture firms to not only back great ideas but also provide valuable operational support to founders.
Challenges in the Investment Landscape
The conversation revealed a constant struggle for many startups, especially those that become reliant on early-stage hype without real product-market fit. Specifically, a case was noted where significant bookings did not translate into deployed ARR because the implementing parties had no motivation to prioritize the software. Such issues, often referred to as mirage product market fit, underscore the risks associated with assessing success based solely on sales figures. This serves as a cautionary tale for VCs regarding the importance of aligning investment with genuine market needs and operational realities.
Market Pull and Growth Dynamics
There exists a sentiment that market pull will continue to greatly influence the trajectory of startups, particularly in the AI and tech sectors. Companies that respond to immediate market demands with relevant solutions—especially in critical areas such as drug discovery or customer engagement—are likely to thrive. Notably, the discussions highlighted that even amid fluctuations in the industry, it's the focus on solving pressing problems that attracts users and drives growth. Overall, startups with a clear product vision that resonates with the current consumer and enterprise needs will have an advantage going forward.
Navigating the AI Wave and Defensibility
As AI technologies evolve, the challenge remains for businesses to establish a competitive edge while delivering on customer demands. Plenty of firms are capitalizing on AI trends, but distinguishing themselves while maintaining wise business models is critical for longevity. Lessons from previous SaaS models suggest that true success lies in seeking defensible positions that leverage AI, but companies must also remain agile and ready to pivot their business strategies accordingly. The focus shifts from merely being trendy to sustainably integrating AI within existing workflows for truly effective solutions.
Impact of Distribution and Incumbency
The discussion around incumbents highlighted their potential to capture outsized value through existing data and distribution channels. Yet, the stark realization occurred that nimble startups can equally succeed by honing in on specific market segments with tailored solutions. It was underscored that emphasizing a narrow focus could profoundly outpace the innovation efforts of larger entities that may lack the specificity in addressing distinct customer pain points. This realization turns the narrative towards the significance of start-up agility in competitive landscapes dominated by well-established companies.
Jake Saper is a General Partner @ Emergence Capital, one of the leading venture firms of the last 20 years. Their many wins include being early investors in Salesforce, Zoom, Veeva and more. In total, the firm has invested $2BN and returned an astonishing $8BN in cash with much more to come.
In Today’s Episode We Discuss:
04:45 The Zoom Investment Story
10:21 Founder, Market, Traction: Rank Them
26:37 Why Market Pull is the Most Important Thing and How to Know
27:23 Are the Best Deals Always Expensive?
28:25 What is the One Framework Emergence Use for Every Investment
29:08 Lessons from the 16x DPI Zoom Fund
30:44 Why Does Every Partner Do Reference Calls on Every Deal?
35:16 We Have Lied to SaaS Founders: The Revenue Rules Changed
37:53 Where Will Value Accrue in a World of AI?
41:37 Three Reasons Why AI Will Not Replace Vertical SaaS
46:38 Who Wins in AI: Startups or Incumbents?
50:09 Why Should Every Company Aim to Be a “Board Discussion”
55:12 Why is Jake Worried About AI’s FTX Moment?
56:00 What Losing Billions on Salesforce Taught Us About Selling
01:00:07 Why Most VC Partnerships are Broken
01:03:07 Grok vs Anthropic vs OpenAI: Buy and Sell?
01:14:25 Quickfire Round: Insights and Reflections
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