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Opinion
Rajaram: Moritz's Instacart investment was the top VC bet ever
“I think the best venture capital, I, someone asked me what's the best venture capital bets. I talk about a paradoxical one. I think it's Mike Moritz betting on Instacart. Why? Because he lost three hundred and seventy million on web van less than a decade ago.…”
Gokul Rajaram Mar 16, 2026 ▶ 47:11 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Insight
James: Major capabilities beat A/B testing at $30B-$40B transaction scale
“As much as A-B testing and like high velocity optimizations feel like progress, and to some extent they will be, when you're at a business of that scale where we're talking like 30 to forty billion in gross transaction volume, the only thing that really moves …”
Jason James Aug 29, 2025 ▶ 2:08 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi
Opinion
James: Instacart had a neglected culture while Thumbtack was an incredible workplace
“Thumbtack, amazing culture, incredible workplace. I would love to have worked there forever, and Instacart, incredible business, but neglected culture, not a pleasant place to work.”
Jason James Aug 29, 2025 ▶ 42:24 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi
Opinion
Jason James: DoorDash beat Instacart by capturing suburbs and expanding faster
“So yes, DoorDash did beat Instacart. I mean, why did that happen? I think the main thing is they expanded faster, went, you know, beyond restaurant sooner. I think also their key insight was when the suburbs, they got there first, beat, you know, Uber Eats to …”
Jason James Aug 29, 2025 ▶ 44:11 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi
Insight
Paik: DoorDash and Instacart succeed by price-discriminating consumer laziness
“The genius behind Instacart and DoorDash and other companies like that is that they, Perfectly price discriminate laziness and the value of like a leisure hour.”
Chris Paik May 9, 2023 ▶ 31:00 Chris Paik: How I Raised $400M; Substack's Broken Business Model; Music on TikTok vs IG | E1011 · 20VC with Harry Stebbings
Assertion Supported
Jordan: Instacart lost $20-$25 per order when a16z first invested
“From recollection, they were billing something like 10 or 12 dollars per order when we invested, and they were losing 20, 25 dollars per order on each one”
Jeff Jordan Jan 16, 2023 ▶ 33:32 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Jordan: Instacart Lost 75% of Early Users but Held 100% Revenue Retention
“A year out, you know, the number of users declined something like three quarters But the users that stayed spent you know, three or four times more money. So their cohorts were actually on revenue basis were, you know, close to staying at 100%.”
Jeff Jordan Jan 24, 2023 ▶ 25:00 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Disclosure
Jordan: Instacart Lost $20 to $25 Per Order When a16z Invested
“When I, from recollection, they were billing something like 10 or 12 dollars per order when we invested and they were losing 20, 25 dollars per order on each one.”
Jeff Jordan Jan 24, 2023 ▶ 27:33 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Prediction Held up
Jordan: Instacart Avoids Owning Grocery Inventory to Preserve Partner Trust
“That channel conflict is something that Instacart has no desire to do. They want to be the go to partner for the for the gross, the physical grocer.”
Jeff Jordan Jan 24, 2023 ▶ 5:42 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Disclosure
Jordan: Instacart avoids dark warehouses to prevent channel conflict with grocers
“But at that point you're competing with your customer and, you know, that channel conflict is something that Instacart has no desire to do. They want to be the go to partner for the for the gross, the physical grocer.”
Jeff Jordan Jan 16, 2023 ▶ 11:39 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
Assertion Supported
Jordan: Instacart reached significant profitability through process optimizations
“Each of those took, you know, many minutes off of each order, and, you know, time is money, and so, you know, that's just the example of the kind of continuous optimizations they were making, trying to get, take minutes and seconds out of the process, and in d…”
Jeff Jordan Jan 16, 2023 ▶ 35:19 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
Assertion Supported
Jordan: Instacart lost 75% of users yearly, but remaining users spent 3-4x
“In the case of Instacart the number of users declined pretty precipitously from, you know, first purchase to, you know, 10 purchase a year out, you know, they, the number of users declined something like three quarters. But the users that stayed spent you know…”
Jeff Jordan Jan 16, 2023 ▶ 30:48 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Simo: Instacart will lead food relationship evolution over next decade
“And I really believe that it's a company that's going to be at the center of, as a relationship between people and food. Evolves over the next decade, whether it's through personalization, convenience, nutrition, and there's going to be just so many interestin…”
Fidji Simo Oct 18, 2021 ▶ 25:14 20VC: Instacart CEO Fidji Simo on Why You Need Sponsors Not Mentors, Where Management Skills Align with Good Parenting & The First 100 Days as CEO at Instacart; The Challenges, The Surprises and The Next Chapter
Prediction Not checkable as stated
Simo: Instacart will empower local grocers to compete with Amazon
“And I think it means that we will have helped our retail partners really compete against Amazon and we'll have Given them all of the technology tools so that they remain at the center of local communities and allow local communities to thrive.”
Fidji Simo Oct 18, 2021 ▶ 34:52 20VC: Instacart CEO Fidji Simo on Why You Need Sponsors Not Mentors, Where Management Skills Align with Good Parenting & The First 100 Days as CEO at Instacart; The Challenges, The Surprises and The Next Chapter
Assertion Supported
Taggar: Gary Tan Saved Instacart and Wired Money to Coinbase
“I think it was he who accepted Instacart into Y Combinator after the deadline had passed for applications, and similarly with Coinbase early on, I think this is public, but there was a moment where they were having a bit of a liquidity crunch, and Gary just wi…”
Kulveer Taggar May 31, 2019 ▶ 11:20 20VC: Why You Must Have A Customer Acquisition Strategy From Day 1, How To Test and Validate Ideas At Speed & Why You Should Speak To Investors Before Starting Work On Your Idea with Kulveer Taggar, Founder @ CEO @ Zeus Living
Insight
Garg: D2C food sector will yield multiple multi-billion dollar companies
“An analogy would be like if you were to judge Instacart a thousand percent on web fan, and some VCs do, but I find that it's important to specialize at least in some areas so that you can look under the hood because people eat in many different ways, and it's …”
Ooshma Garg Nov 9, 2018 ▶ 14:18 20VC: Being A Wartime Leader in a Time of Peace, Why Marketing Channel Diversification Is Like The Life of A Scientist and Why Small and Mighty Beats Loud and Weak with Ooshma Garg, Founder & CEO @ Gobble
Opinion
Offline retailers will prefer Instacart over Amazon as a partner
“Offline retailers need Instacart to work. Amazon is too much of a threat. Instacart is closer to a partner.”
Ryan Caldbeck Nov 2, 2018 ▶ 30:08 20VC: Ryan Caldbeck on Why The Business Model of VC is Broken, Who is To Blame, How The Best Funds Will Use Data Intelligently Moving Forward & Whether We Are In A Consumer Bubble Or Not?
Insight
Nelson: Grouping all AI products together is as flawed as web apps
“I think the problem is largely with thinking about those things as synonymous to each other. It's kind of like saying that everybody who builds a web app is competing in the same category, right? It's kind of like saying that just a software app like MyFitness…”
Maren Nelson Jan 13, 2017 ▶ 12:31 20VC: Building An AI Company For The Long Term? How Humans & Machine Learning Can Work Together? What Applications Are The Conversational Interface Best Suited To with Maran Nelson, Founder & CEO @ Clara Labs
Prediction Not checkable as stated
Kyle Hill: Homogeneous marketplace workers will eventually be replaced by robots
“I look at those and no offense to any of those companies, but you could probably replace those workers with robots.”
Kyle Hill Jul 15, 2016 ▶ 7:09 20VC: Why Every Employee Should Re-Apply For Their Job Every Year & The Strategies To Prepare For A Successful Fundraise with Kyle Hill, Founder & CEO @ HomeHero
Assertion Supported
James: Instacart's Snap EBT integration reached $1B within a year
“When we launched Snap EBT, which is like food stamps to be able to pay with those on Instacart. It became a billion dollar business line in less than a year and then grew up to be four billion.”
Jason James Aug 29, 2025 ▶ 2:50 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi
Disclosure
Nayak: Scale AI labeled e-commerce data for Meta, Instacart, and DoorDash
“Like I started the e-commerce team at scale where we were labeling e-commerce data, like from Meta, from Instacart, from DoorDash.”
Aatish Nayak Apr 11, 2025 ▶ 15:21 20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak
Opinion
Uber-Instacart partnership strengthens their position against DoorDash
“I was reading about the deal that they made with, between Uber and Instacart, and I think that's brilliant, like, both of them, right? Like, it positioned them much better in restaurant delivery against players like, you know DoorDash.”
Maria Angelidou Oct 4, 2024 ▶ 52:13 Maria Angelidou:Product Lessons Leading Facebook App Monetisation Team to Billions in Revenue |E1210 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lerner: Middle zone for marketplace network effect startups is empty
“You've got your Instacart, your Uber, your Lyft. They've kind of, like, gotten to where they need to be. There isn't actually very many people in that middle zone in terms of Marketplace network effects today.”
Ely Lerner Oct 25, 2023 ▶ 1:00:05 Ely Lerner: Should Startups Hire Advisors & How much should they be paid? | E1075 · 20VC with Harry Stebbings
Insight
Sri Batchu: The best executives reject distracting initiatives regardless of impact
“Simplification is a superpower, and it's actually very difficult and a lot of executives, you know, when they're faced with two potentially high-impact initiatives, are often tempted to say, let's do both. Let's figure out how we can do both. The good ones can…”
Sri Batchu Jul 26, 2023 ▶ 4:44 Sri Batchu: Biggest Growth Lesson from Instacart & Opendoor; 70% of Experiments Should Fail | E1040 · 20VC with Harry Stebbings
Insight
Kaba: North Star metrics should be derived from qualitative product magic
“Metrics are always a representation of your strategy, right? And so you shouldn't just choose a metric. I talked to founders about is like, let's talk qualitatively about what is the magic of the product? What makes this product really tick? And how do we know…”
Bangaly Kaba Mar 25, 2022 ▶ 15:55 20VC The Memo: Inside the Growth Engines of Facebook, Twitter, Instagram and Instacart with the Growth Leaders Who Built Them; How Instagram Went from 440M to 1BN, How Twitter Changing Their Signup Flow was a Needlemover and How Removing Card Payment Requ
Assertion Partly supported
Gupta: Instacart lost $20 on every order during its early operations
“When we were losing 20 dollars on every order at Instacart, which we were at the beginning”
Ravi Gupta Sep 14, 2020 ▶ 31:44 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts
Prediction Not checkable as stated
Elad Gil: Instacart will retain massive growth post-pandemic
“Instacart, I think even if it snaps back to half of Where it is today, it's still going to be massive acceleration of the business.”
Elad Gil May 26, 2020 ▶ 10:09 20VC: Elad Gil on Startup Offense and Defence in a Recession, How The Venture Landscape Has Shifted & All Things Valuations, Secondaries and Layoffs
Assertion Not checkable as stated
Galston: Chicago is Uber and Instacart's second or third largest market
“If you ask Uber or Instacart, what, you know, their second or third most important market is, it's almost inevitably Chicago.”
Ezra Galston Aug 17, 2015 ▶ 8:15 20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures
Disclosure
David Wu passed on investing in Stitch Fix, Instacart, and Dollar Shave Club
“But from an investor perspective, I would probably say that, you know, the biggest mistakes have to be, you know, my personal portfolio to date. Or anti-portfolio. And three that come to mind are all for different reasons where companies that I passed on that …”
David Wu Jul 29, 2015 ▶ 19:04 20 VC 058: 10 Key Traits To Be A Successful Founder with David Wu, General Partner @ Maveron
Assertion Supported
Sri Batchu: Instacart was more complex than Opendoor as a four-sided marketplace
“Instacart was in some ways an even more complicated business than Opendoor because it's a four sided marketplace. We have shoppers, we have buyers, we have advertisers, and we have the retailers that are on the platform as well with various different incentive…”
Sri Batchu Jul 26, 2023 ▶ 4:23 Sri Batchu: Biggest Growth Lesson from Instacart & Opendoor; 70% of Experiments Should Fail | E1040 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Batchu: Instacart's growth and consumer team was over 300 people
“Instacart, the growth and consumer team was over 300 people, right?”
Sri Batchu Jul 26, 2023 ▶ 27:28 Sri Batchu: Biggest Growth Lesson from Instacart & Opendoor; 70% of Experiments Should Fail | E1040 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Simo Applied Her Core Management Frameworks to Parenting Her Daughter
“I built a lot of my management tools before I got pregnant. And so, in fact, I feel like I have applied a lot of my management tools on my daughter rather than the other way around.”
Fidji Simo Oct 18, 2021 ▶ 6:28 20VC: Instacart CEO Fidji Simo on Why You Need Sponsors Not Mentors, Where Management Skills Align with Good Parenting & The First 100 Days as CEO at Instacart; The Challenges, The Surprises and The Next Chapter
Assertion Not checkable as stated
Gupta: Instacart's execution stalled when attempting six priorities in one quarter
“And so I remember this time at Instacart where we had six company priorities in a quarter and a month into the quarter or halfway into the quarter, we weren't moving nearly as fast as we wanted on any of them.”
Ravi Gupta Sep 14, 2020 ▶ 18:07 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts
Assertion Not checkable as stated
Simo: Instacart CEO role requires far more external focus than Facebook
“That's actually a kind of a big difference from my prior role, which was a lot more internally focused. This role is a lot more externally focused”
Fidji Simo Oct 18, 2021 ▶ 27:47 20VC: Instacart CEO Fidji Simo on Why You Need Sponsors Not Mentors, Where Management Skills Align with Good Parenting & The First 100 Days as CEO at Instacart; The Challenges, The Surprises and The Next Chapter
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