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Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. Additionally, he has led sizable early-stage venture capital investments in dozens of companies including Upstart (NASDAQ: UPST), Tilray (NASDAQ: TLRY), Leafly (NASDAQ: LFLY), Wish (NASDAQ: WISH), Workrise, and Rippling. Prior to founding Bedrock, Geoff served as a partner at Founders Fund for several years. ------------------------------------------ Timestamps: 0:00 Intro 0:40 How did you meet Parker Conrad 4:10 Why is Parker Conrad a narrative violation? 6:41 Do you have vengeance? 10:04 What does a “compound startup” mean? 12:07 What are strengths and weaknesses of Rippling? 16:15 Do you engage in outcome scenario planning? 20:08 What have you learned from losing money? 22:08 Uncapped notes 25:20 How did you miss out on Series B? 29:11 What was the unique view to invest in Series D? 33:15 How do you engage with Growth? 35:26 When to return money to LPs 37:19 How does the current market affect Rippling’s customer base? 39:24 Do VCs need to be optimistic? 40:30 How will you advise Rippling? 41:59 How much of Bedrock’s capital is allocated to Rippling? 42:54 Rippling’s 10x case 44:30 A team of founders at Rippling 46:03 Most under-appreciated aspect of Rippling ------------------------------------------ In Today’s Episode with Geoff Lewis: 1.) Meeting Parker Conrad: A Generational Defining Entrepreneur: How did Geoff first come to meet Parker Conrad, over a decade prior to making the first Rippling investment? What was it about Parker that compelled Geoff so much in the early days? How did Geoff analyze the chip on Parker’s shoulder from Zenefits? How does he believe it has driven him with Rippling? 2.) Searching for Narrative Violations in Rippling: Why does Geoff believe Parker himself is a “narrative violation”? What does Geoff believe is the foundational narrative violation in the way Parker is building Rippling? Rippling has a large portion of its team as former founders, how does Geoff believe this impacts the culture of Rippling? What does Geoff believe are the single biggest barriers to Rippling being the “App Store for Business”? On the upside case, if Rippling goes right, how big could this be? 3.) Rippling: The Financing: What has been Geoff’s biggest lesson on price and price sensitivity that he has learned through Rippling? Why does Geoff never do uncapped notes? Why did Geoff break that rule with Rippling? What gave Geoff the conviction to write Bedrock’s largest ever check in Rippling’s Series D? What was the massive mistake that both Geoff and Bedrock made in not financing their Series C? 4.) Geoff Lewis: The Investor What single trait does Geoff believe all generational defining founders share? How does he test for it? Does Geoff believe he has a chip on his shoulder today? How has his relationship to the chip on his shoulder changed over time? To what extent does Geoff engage in outcome scenario planning when making investments? What upside scenario plan does Geoff need to be able to see for him to make an investment? Has Geoff ever lost money in an investment? What were his takeaways from this experience? ------------------------------------------ Subscribe to the Podcast: https://www.thetwentyminutevc.com/geoff-lewis-2/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Geoff Lewis on Twitter: https://twitter.com/GeoffLewisOrg ------------------------------------------ #Rippling #venturecapital #venturecapitalist #GeoffLewise #BedrockCapital #HarryStebbings #20VC

Harry StebbingshostGeoff Lewisguest
Oct 4, 202247mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Inside Bedrock’s $200M Bet on Rippling and Compound Startups

  1. Geoff Lewis of Bedrock Capital explains why his firm has invested roughly $200M into Rippling across multiple rounds, making it a highly concentrated position in their first three funds.
  2. He frames CEO Parker Conrad as a ‘life’s work’ founder and “ultimate narrative violation,” driven by a mix of ambition, vengeance, and resilience that Bedrock believes is key to building generational companies.
  3. Lewis unpacks Rippling’s “compound startup” model: starting from payroll, expanding into a broad workforce management suite, owning the employee graph, and potentially becoming an “AdWords for SaaS” distribution layer.
  4. The conversation also covers Bedrock’s philosophy on uncapped notes, capital concentration, reserves vs distributions, macro timing, and how they think about growth-stage investing and risk in a volatile market.

IDEAS WORTH REMEMBERING

5 ideas

Back ‘life’s work’ founders with an extra motivator like vengeance.

Lewis argues that many great entrepreneurs (e.g., Rockefeller, Jobs) are driven not only by a big vision but also by a sense of being wronged, which fuels irrational perseverance; Parker Conrad fits this pattern and self-identifies as a “narrative violation.”

Use capital concentration to maximize returns in truly exceptional companies.

Bedrock has concentrated roughly 20% of three funds into Rippling (plus more into a few other winners), rejecting traditional diversification limits and aligning with the view that position-sizing, not deal count, is often the real driver of venture returns.

Avoid competitive formal fundraises; catalyze rounds and move pre-emptively.

After losing the Series A and over-analyzing the Series B, Bedrock concluded that once a process memo goes to a dozen firms, the round is effectively ‘dead’ to them; instead, they now focus on originating or catalyzing rounds directly with founders.

Favor businesses where the preferred stack grows linearly or sublinearly with revenue.

Lewis emphasizes that many big-outcome companies require massive dilutive capital; he prefers models like Rippling’s, where strong unit economics and product-led expansion mean the amount of preferred capital needed scales modestly relative to revenue growth.

Exploit macro dislocations by moving up-market when others retreat to early stage.

In anticipating a growth and then crypto crash, Bedrock sold Bitcoin/Ethereum, recycled proceeds, and deliberately sought the “best growth-stage asset on the planet” where they believed they wouldn’t lose money and still had a credible 10x path—landing on Rippling.

WORDS WORTH SAVING

5 quotes

When you find a transcendent life’s work entrepreneur with vengeance, you ought to invest.

— Geoff Lewis

I don’t like companies where the people don’t wear their shoes in the office.

— Geoff Lewis

It can become the AdWords for SaaS… the way that business software is sold.

— Geoff Lewis

By the time a company’s in a formal financing process, it’s kind of dead to us.

— Geoff Lewis

This is a rare human who, to wholly self-actualize, has to build one of the largest companies on the planet.

— Geoff Lewis

Geoff Lewis’s long-term relationship and assessment of Parker ConradThe concept of “narrative violations” and vengeance-driven foundersRippling as a “compound startup” and owner of the employee graphRippling’s business model, upgrade dynamics, and potential to become ‘AdWords for SaaS’Bedrock’s investment strategy: capital concentration, uncapped notes, and growth-stage entriesMacro environment, repricing of growth, and reserves vs LP distributionsCulture at Rippling: ex-founders, chips on shoulders, and execution risk

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