EP 100: Jeremy Levine (Partner, Bessemer) Reflects on His Best and Worst Investments

The Logan Bartlett Show

Exploring Competitive Evaluation and Joy in Avoiding Wasted Opportunities in Investments

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The speaker highlights their competitive nature in evaluating investment opportunities, emphasizing the importance of actively participating in evaluating deals to gain insights, even if not all deals result in success. They express the desire to thoroughly understand missed opportunities to inform future decisions. Despite acknowledging the presence of FOMO (fear of missing out), the speaker embraces JOMO (joy of missing out) as a mental model of self-preservation, finding satisfaction in avoiding wasted time on unlikely prospects. This approach protects them from feeling excluded from potential opportunities and prevents the frustration of pursuing futile endeavors.

After 23+ years in venture capital, Jeremy Levine has thrived in many eras, taking risks on now-iconic companies like LinkedIn, Shopify, Yelp, Pinterest, and more. In our discussion, Jeremy shared stories behind these investments and the mindsets he’s developed along the way. We also explored how the VC landscape has evolved over the last 20 years and where the industry may head next. Plus, Jeremy shares insights from his journey into VC, along with foundational advice and principles that anyone aspiring to succeed in the industry may find valuable. Overall, an in-depth discussion for anyone who wants to nerd out on venture capital with us.

(00:00) Intro

(01:03) Exploring the Personal Motivations Behind Venture Capital

(01:41) The Impact of Technology on Venture Capital

(03:11) The Reality of Venture Capital Impact

(06:45) The Ideal Venture Investment: The Donut Company Metaphor

(07:30) Operator vs. Career Investor: The Best Venture Capitalists

(09:57) The Dynamics of Choosing a Venture Investor

(14:03) The Unique Paths to Success in Venture Capital

(17:04) Authenticity and Adaptability in Venture Capital

(26:33) Navigating the Complexities of Venture Capital Careers

(34:11) Jeremy Levine's Journey to Bessemer Venture Partners

(40:00) Navigating the Venture Capital Landscape: Insights and Strategies

(40:30) The Competitive Edge in Early 2000s Venture Capital

(43:26) Reflections on Career Paths and the Role of Serendipity

(47:04) The Intricacies of Decision Making in Venture Capital

(52:37) Evaluating Investment Opportunities: The Price Sensitivity Debate

(55:22) Learning from Success and Failure: The Jet.com Story

(01:08:26) The Evolution of Successful Entrepreneurs: Insights from Shopify and Yelp

(01:16:22) The Strategic Advantage of Repeat Entrepreneurs in the Startup Ecosystem

(01:19:38) Navigating Market Dynamics: Insights and Analogies

(01:20:09) The Evolution of a Venture Capitalist: From Ideas to Impact

(01:21:22) Pioneering User-Generated Content: A Venture Success Story

(01:23:36) Exploring E-Commerce and the Power of Advertising

(01:24:59) Innovative Investment Strategies: SaaS and Payment Processing

(01:34:53) Bessemer's Legacy and Venture Capital Evolution

(01:39:57) Expanding Horizons: Bessemer's Global and Diverse Investment Approach

(01:52:35) Cultivating Talent and Embracing Industry Dynamics

(02:02:36) Navigating Budgets and Investment Strategies in Venture Capital

(02:03:55) The Importance of Accountability and Decision-Making Records

(02:05:46) Investment Memo Strategies: Beyond Templates

(02:08:43) The Dynamics of Voting and Decision Making in VC Firms

(02:16:19) The Evolution of Venture Capital: Trends and Predictions

(02:21:13) Building a Successful Venture Capital Firm: Culture and Operations

(02:29:57) Mentorship and Individual Growth in Venture Capital

(02:39:40) Navigating the AI Investment Landscape

(02:41:36) The Debate on Announcing Funding Rounds

(02:44:20) Closing Remarks

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.