Betting on product to win in fantasy sports, with Underdog’s Jeremy Levine
As the NFL season kicks off this week, host Jeff Berman talks with a serial entrepreneur known for innovating in fantasy sports. Jeremy Levine is the founder and CEO of Underdog, a rapidly scaling unicorn. Levine reveals how a relentless focus on product helps his company break through entrenched competition.
Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
EP 100: Jeremy Levine (Partner, Bessemer) Reflects on His Best and Worst Investments
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
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
Follow on Socials
📸 Instagram - https://www.instagram.com/theloganbartlettshow
📱 X - https://twitter.com/loganbartshow
🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow
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 of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
Tap follow and enable notifications to stay ahead of the game.
Bessemer Venture Partners - Building a VC Firm that Lasts Centuries - [Invest Like the Best, EP.327]
My guests this week are Jeremy Levine, Kent Bennett, and Brian Feinstein. They are partners at one of the oldest and most storied venture firms in the world, Bessemer Venture Partners. Our conversation is split into two parts. First, we explore Bessemer itself. It’s over 100 years old and has a unique operating model with lessons for every investment firm in the market. We then discuss Jeremy, Kent, and Brian’s investing styles and outlook. What they look for in businesses, their thoughts on various sectors like vertical market software, and we close with a discussion about AI and defensibility. Please enjoy this great conversation.
Listen to Founders Podcast
Founders Episode 136 - Estee Lauder
Founders Episode 288 - Ralph Lauren
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
-----
This episode is brought to you by Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 55,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
(00:03:14) - (First question) - The unique history of Bessemer and how the firm stays current
(00:08:55) - The role of heritage and cooperative partnership in Bessemer’s model
(00:14:36) - How giving each partner autonomy and commissions can lead to better personal and company outcomes
(00:17:18) - The extent of freedom a partner has in terms of the style of investments made
(00:20:38) - Retro-analyzing the effectiveness of their investment roadmaps and core insights
(00:25:10) - What conflict typically looks like in partners’ conversations and how they resolve it
(00:27:06) - How they enable their junior staff using apprenticeship and open dialogue
(00:31:31) - Their different taste in investment targets
(00:35:11) - How they each evaluate companies based on their unique interests
(00:42:32) - Their thoughts on valuations and how they have dealt with with run-ups in the tech market
(00:45:46) - What they anticipate in the future of early-stage investing
(00:49:43) - The significance of Centaur companies that have hit $100-million in revenue
(00:52:38) - The success of Bessemer’s writing and online content
(00:55:13) - Where the vertical market software industry is in its life cycle
(00:59:12) - How the next wave of innovation may revolutionize software or even depart from it
(01:02:33) - Advice they give to companies looking to prepare for future shifts in tech and AI
(01:04:46) - What excites them and what scares them within the development of LLMs
(01:08:18) - Defensibility of an LLM-based company, given the high level of competition
(01:10:39) - How their firm deals with terminating partners if and when they aren’t a good fit
(01:14:53) - The kindest thing anyone has ever done for each of them
20VC: The Pinterest Memo: Bessemer's Jeremy Levine on The Secret To Success within User Generated Content Plays, Where Most Investors Make Mistakes When Analysing Consumer Social and How The Pinterest Deal Wouldn't Have Happened without a Diverse Partners
Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the leading venture firms of the last 2 decades with a portfolio including the likes of Pinterest, Shopify, LinkedIn, Yelp, Twilio and many more. As for Jeremy, five of his early-stage investments—LinkedIn, MindBody, Pinterest, Shopify and Yelp—grew into billion-dollar publicly traded companies. As a result of his incredible portfolio, he has featured on the Forbes Midas List for several years running.
In Today's Episode with Jeremy Levine You Will Learn:
1.) How Jeremy came to make one great decision and make one big mistake all in one rainy afternoon in Palo Alto? What was the story behind meeting the Pinterest team for the first time? Who was there? How did it go down?
2.) Market: How did Jeremy analyse the market at the time of the investment? What had been some core lessons Jeremy had learned on what made successful user-generated content plays? Where was Jeremy wrong in how he analysed the market? In what way is Jeremy surprised with how the market evolved? How does Jeremy analyse market timing today?
3.) Team: Jeremy has previously called Ben Silberman a "product visionary", what made Jeremy say this about Ben? How did Jeremy get over the concern of many VCs that Pinterest did not have a technical co-founder? Having seen Ben change over the last decade, what have been the biggest changes in Ben's leadership style over the last 10 years?
4.) Traction: When evaluating traction, where does Jeremy think so many investors make mistakes today? How should founders determine what is their core North Star metric? What gave Jeremy the confidence Pinterest could "cross the chasm"? How did the early Pinterest cohorts look both from usage and retention? What elements surprised and impressed?
5.) Pre + Post Mortem: What did Jeremy see as the likely reasons why Pinterest would not work? How did Jeremy think through what it took for UGC platforms to monetise at the time? Where was he wrong here? What did Jeremy see as the upside? What did he believe Pinterest could be if all the stars aligned?
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
20VC: Bessemer's Jeremy Levine on Why We Are In A Fallow Period For Consumer, Why It Is Bogus That Operational VCs Can Add More Value & 2 Golden Rules To Always Tell Entrepreneurs Pre-Investment
Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the world's leading venture funds with prior investments in the likes of Skype, Shopify, LinkedIn and Twitch, just to name a few. As for Jeremy, 4 of the companies he has invested in with Bessemer have become $Bn companies with 2 of the above; LinkedIn and Shopify, in addition to Yelp and MindBody. If that was not enough, Jeremy is also on the boards of some phenomenal companies in the likes of Pinterest, Yelp and Shopify to name a few.
In Today's Episode You Will Learn:
1.) How Jeremy made his entrance into the world of venture and came to be a partner @ Bessemer?
2.) What are the 2 rules Jeremy has with every founder he invests in, prior to making the investment? Why does Jeremy have these rules? At what stage of the pre-investment process are they illustrated?
3.) What are the 2 main reasons that Jeremy believes we are entering a fallow period for the world of consumer? What elements of the incumbency advantages of Facebook, Apple and Google concern Jeremy most? Where does he also see great opportunity?
4.) How has Jeremy seen his style of board member change over the last 16 years? How does Jeremy believe founders can optimize their board through strategic positioning of the VCs they have and where they are placed?
5.) Why does Jeremy believe that it is bogus that operational VCs can provide more value than non-operational VCs? What is the thesis behind this? Where are the core strengths of operational VCs? Where founders must be wary of operational VCs?
Items Mentioned In Today's Show:
Jeremy's Fave Book: The Outsiders
Jeremy's Fave Blog: Dan Primack
Jeremy's Most Recent Investment: Toss
As always you can follow Harry, The Twenty Minute VC and Jeremy on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.
Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co