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

The Logan Bartlett Show

The Evolution of Successful Investment Ideas

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One successful investment idea stemmed from a deep dive into e-commerce companies that were not relying on venture capital but were still able to spend money on online ads, leading to the realization that profitability was key. This understanding paved the way for investing in e-commerce companies like diapers.com and eventually in Shopify. Another profitable investment was in MindBody, a software company for Yoga Studios, that expanded its market by leveraging its software for various industries and integrating payment processing, setting a new trend in the software industry. This insight also influenced Shopify's business model. These examples highlight the importance of patience in venture capital, waiting for differentiated and compelling ideas to generate significant returns over the long term.

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.