20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation...
The Twenty Minute VC (20VC)Full Title
20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne
Summary
This episode features Chris Olsen of Drive Capital discussing the decentralization of entrepreneurship away from Silicon Valley and the lessons learned from his VC career.
He emphasizes the Midwest as a significant opportunity for venture investment, highlighting its growing ecosystem and the potential for unique competitive advantages outside traditional tech hubs.
Key Points
- Chris Olsen's journey into VC began with a proactive approach of cold-calling firms after graduating with a political science degree, eventually leading him to roles at TCV and UBS before Sequoia Capital.
- His early fascination with VC was sparked by the story of Sequoia returning $100 million to not disclose portfolio companies, indicating a lucrative business model.
- A key learning from Sequoia was the importance of an apprenticeship model and learning by doing, as well as understanding the value of founders who are entrepreneurs and often immigrants.
- Olsen's thesis for Drive Capital is rooted in the observation that cloud computing commoditized infrastructure, shifting value to the enablement of technology across all industries, and the need for VCs to be close to their customers.
- Drive Capital was founded on the conviction that the Midwest, with its large customer base, abundant engineering talent from universities, and a significant number of Fortune 500 companies, represented a substantial, untapped investment opportunity.
- Initial LP reactions to Drive Capital's Midwest focus were largely skeptical, often preferring to invest in traditional Silicon Valley geographies, but on-the-ground visits to the region proved persuasive to some LPs.
- The firm actively showcases the Midwest's entrepreneurial talent by taking LPs to meet founders and visit promising companies, demonstrating that the raw ingredients for success are present.
- Valuations for top-tier companies in the Midwest, despite less capital competition, are competitive with Silicon Valley, indicating that A-plus companies command similar market prices.
- Drive Capital reserves more capital for early-stage investments than is typical in California, acknowledging the current lack of established follow-on investors in the region, but still allocates reserves based on company performance.
- The firm identifies a capital trough between $3 million and $40 million in fundraising rounds for Midwest companies, with external growth capital from coastal firms often entering once companies reach around $1 million in monthly revenue.
- Olsen predicts the decentralization of VC and entrepreneurship as a major trend over the next two decades, extending beyond the Midwest to other global regions, driven by deep domain expertise combined with technology.
- He believes the biggest misnomer is that smart people and opportunities are exclusive to Silicon Valley, stating that talent and innovation exist everywhere.
- The investment in Duolingo exemplifies Drive Capital's focus on world-class founders in industries ripe for technological disruption, specifically in education and language learning.
Conclusion
The decentralization of entrepreneurship and venture capital away from traditional hubs like Silicon Valley is a significant and growing trend.
The Midwest presents a compelling investment opportunity with a strong foundation of talent, customers, and industrial expertise that is often underestimated.
Future success in venture capital will increasingly depend on recognizing and capitalizing on talent and innovation wherever it exists, rather than adhering to geographical biases.
Discussion Topics
- How can aspiring entrepreneurs outside of traditional tech hubs build successful companies and attract venture capital?
- What are the biggest advantages and disadvantages of investing in regions with less established venture capital ecosystems?
- How is the increasing decentralization of entrepreneurship reshaping the global investment landscape and the role of VCs?
Key Terms
- VC
- Venture Capital; investment from firms that provide capital to startups and small businesses with long-term growth potential.
- LPs
- Limited Partners; investors who commit capital to a fund managed by a general partner.
- M&A
- Mergers and Acquisitions; corporate finance transactions involving the consolidation of companies or their assets.
- IPO
- Initial Public Offering; the first sale of stock by a private company to the public.
- FOIA
- Freedom of Information Act; a U.S. law that provides the public the right to request access to records from any federal agency.
- Cloud Computing
- The delivery of computing services—including servers, storage, databases, networking, software, analytics, and intelligence—over the Internet (“the cloud”) to offer faster innovation, flexible resources, and economies of scale.
- Run Rate Revenue
- A projection of a company's annualized revenue based on its current performance.
Timeline
Chris Olsen details his unconventional path into venture capital, starting with cold calls and eventually securing roles at TCV, UBS, and Sequoia Capital.
Olsen recounts his initial inspiration for venture capital stemming from an article about Sequoia Capital's significant return of funds.
Olsen shares his key lessons from his time at Sequoia Capital, emphasizing the firm's unique partnership model and the value of an apprenticeship approach.
Olsen explains how a past Sequoia investment decision, turning down a company due to its proximity to Silicon Valley, highlighted a shift in investment philosophy driven by cloud computing and the commoditization of infrastructure.
Olsen describes how his partner Mark Kwame's experience with Jobs Ohio revealed the overlooked potential in the Midwest, including a large customer base and engineering talent, which inspired the creation of Drive Capital.
Olsen details the data-driven process of validating the Midwest investment thesis, noting that each piece of diligence reinforced the opportunity.
Olsen discusses the initial skepticism from friends and LPs regarding his decision to focus on the Midwest, contrasting it with their preference for established Silicon Valley investments.
Olsen explains how personally showing LPs the Midwest's burgeoning startup scene and talented founders convinced them of the investment opportunity.
Olsen addresses the economic dynamics of the Midwest market, explaining that while capital is scarcer, leading companies still achieve valuations comparable to those in Silicon Valley.
Olsen outlines Drive Capital's strategy for reserve allocation, highlighting the need for greater reserves due to the nascent follow-on capital market in the Midwest.
Olsen describes the capital landscape in the Midwest, noting a robust seed-stage market but a trough for Series A/B rounds, and the benchmarks required to attract growth capital.
Olsen discusses his outlook on the decentralization of VC and entrepreneurship, emphasizing its global reach and the increasing importance of domain expertise coupled with technology.
Olsen provides an example of Drive Capital's investment focus in the robotics space, targeting small and mid-scale manufacturers in the Midwest.
Olsen participates in a quick-fire round, sharing his thoughts on his favorite book, a transformational personal experience, the biggest trend he believes in, and a common misnomer about Silicon Valley.
Olsen explains the rationale behind Drive Capital's investment in Duolingo, citing the founder's caliber and the market's need for technological innovation in education.
Episode Details
- Podcast
- The Twenty Minute VC (20VC)
- Episode
- 20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne
- Official Link
- https://www.thetwentyminutevc.com/
- Published
- October 28, 2025