Enterprise Customer

topic on 20 shows · 93 statements across 89 episodes

Acquired the Y Combinator Startup Podcast Founder's Journal In Depth the Pitch Another Podcast Startups For the Rest of Us We Live to Build Latent Space Lenny's Podcast the Neon Show the Official SaaStr Podcast A Product Market Fit Show Top Founders the MAD Podcast the a16z Podcast Big Technology TBPN 20VC David Senra

The latest 60 statements about Enterprise Customer, every show

NEON SHOW Assertion Not checkable as stated
Jain: No Observe AI enterprise customers have reduced human headcount yet
“I've not seen reduction in customer service reps by any of our customers. And we have customers who have tens of thousands of agents. So we would be the first one to see the impact and the reality is nothing yet.”
Swapnil Jain Aug 14, 2026 ▶ 42:40 ChatGPT Killed My $50M ARR Business Overnight | Swapnil Jain Observe Al
WE LIVE TO BUILD Assertion Not checkable as stated
Meiring: Most enterprise customers only understand AI as an email drafting tool
“Many of our customers, they're still using AI to help them write a better email, right? That's the full extent of their understanding around what artificial intelligence can do.”
Ray Meiring Jul 21, 2026 ▶ 4:32 80% of the Workload Done Before a Human Touches It
20VC Prediction Not checkable as stated
Jain: Enterprise AI adoption hurdle is Chinese model origin, not open source
“From a point of view of open source and using the model, everybody's going to be fine. The question is going to be, are they okay with the Chinese model or not? That's the only question here. It's not open source versus closed source.”
Arvind Jain Jul 11, 2026 ▶ 13:53 ⁠Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
O'Driscoll: Enterprise Clients Will Pay Double for Higher AI Resolution Rates
“This is a category where everyone can articulate the 30% where it is there. And then to your point, they can go, ooh, the next 10% is going to cost more. That's a high class problem. Maybe what you're saying is you get, you go from 30% resolution to 65% resolu…”
Rory O'Driscoll Jul 9, 2026 ▶ 1:06:03 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
NEON SHOW Prediction Not checkable as stated
Saxena: Enterprises will demand autonomous AI resolution within two years
“At some point, I bet you, 12 months, 18 months, two years from now, the customer will come and say, Shashank, this is very dumb. I'm unhappy. Why? Because you've already done the whole resolution plan. Why do I have to come in and manually hit approve? Just do…”
Shashank Saxena Jun 11, 2026 ▶ 38:59 Questions Every Founder Must Answer Before Taking an Acquisition Offer | Shashank, VNDLY & Pantomath
McCarthy: BackOps wins enterprise deals by building customer-branded board ROI decks
“What we started doing was just building the use cases for the customer and giving them the entire use case and the ROI analysis that they could present to their board with their branding and all of the information that we've gathered to try to make it as light…”
Sean McCarthy May 4, 2026 ▶ 7:31 How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean... · PMF Show
PRODUCT MARKET FIT Assertion Not checkable as stated
McCarthy: Most enterprise customers reject always-on AI screen recording for now
“We found that most customers have asked that we started this way and eventually would be okay with more of like a screen watching type scenario. But for right now, Have felt the vast majority think it's a little too much too soon.”
Sean McCarthy May 4, 2026 ▶ 27:41 How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean... · PMF Show
McCarthy: Pitching generic AI efficiency to enterprises almost never works
“Going to these customers as an AI company and saying, hey, we're going to make you more efficient. What are your problems? Works almost never because they have so many problems and they usually don't know where to begin.”
Sean McCarthy May 4, 2026 ▶ 37:20 How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean... · PMF Show
a16z Prediction Not checkable as stated
Sinofsky: Enterprise AI security fears will let startups outpace big companies
“Part of what's going to happen is you're, we're going to go through this phase where like the enterprise customers are just going to like close everything off. Until there's some sense of sanity in all of this, and then, but in the meantime, the individual, an…”
Steven Sinofsky Apr 8, 2026 ▶ 25:41 Box CEO on the AI Adoption Gap | The a16z Show
NEON SHOW Insight
Jindal: Signing giant enterprise customers early forces them to dictate product roadmaps
“Other challenge you could also happen is if you go bring a very large customer very early on, then that customer is going to force you product in a direction you may not want to go, right? I mean, if you bring in, I don't know, Apple as a customer, more than l…”
Manish Jindal Apr 2, 2026 ▶ 29:43 Why "Boring" Infrastructure is the Best Path to a $60B Company | Manish Jindal, Cloudflare & Arize
DAVID SENRA Disclosure
Fried: 37signals Intentionally Avoids Enterprise Customers to Focus Exclusively on SMBs
“Our customers are small business owners, and I just, I don't care about enterprise customers. I don't want them. I like small, medium-sized businesses. They're more like me.”
Jason Fried Feb 15, 2026 ▶ 31:48 Jason Fried: Your Only Competition Is Your Costs
MAD Insight
LeCroix: Enterprise AI customers reject deploying multiple models for tasks
“Customers aren't happy if you require them to deploy five different models to get their job done.”
Timothée LeCroix Feb 12, 2026 ▶ 44:10 Mistral AI vs. Silicon Valley: The Rise of Sovereign AI
LENNY'S PODCAST Assertion Not checkable as stated
DeWitt Grosser: Procurement is enterprise customers' biggest AI deployment bottleneck
“Their biggest issue in deploying AI is actually just getting through procurement.”
Jeanne DeWitt Grosser Nov 30, 2025 ▶ 43:38 What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
MCP is the primary method enterprise customers use to add agent context
“The MCP is huge, it seems like. It is the way that a lot of the, especially when it comes to, like, digital transformation or some of our enterprise customers, it's where they're going to be able to be at, or where they are able to add context.”
Jared Palmer Nov 10, 2025 ▶ 22:16 ⚡ Inside GitHub’s AI Revolution: Jared Palmer Reveals Agent HQ & The Future of Coding Agents
20VC Insight
Customizing Product Roadmaps for Single Enterprise Deals Kills Startups
“You've just taken the company and diverted all resources to go build a list of things for a company that may or may not buy, but even if they buy, you've killed the company. Right, because you've taken all the resources to focus on one account, even if you get…”
Chad Peets Nov 7, 2025 ▶ 21:35 20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
NEON SHOW Insight
Bajaria: Enterprise Contracts Prevent AI First-Party Data Network Effects
“And I also warn founders saying that, hey, just because you sync first party data, you know, many people will tell you like, hey, I have the network effect because all my customers give me data and I have the network effect. That's not more because every enter…”
Viral Bajaria Oct 24, 2025 ▶ 53:24 6sense Did What Google Couldn’t : Targeting Companies, Not People | Viral Bajaria
20VC Insight
O'Driscoll: Enterprise AI buyers use startup balance sheet size as key qualification
“I know in some of these wars, having looked at some of these deals and kind of the ERP space and some of the other spaces where you're dealing with enterprise customers, the balance sheet becomes a criteria for qualification.”
Rory O'Driscoll Oct 9, 2025 ▶ 1:16:02 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Scale AI's enterprise and government work primarily consists of model evaluations
“A lot of it's evals and within enterprise customers and government customers, it's mostly evals because somebody has got to establish the benchmark for like what good looks like.”
Jason Droege Oct 9, 2025 ▶ 31:40 Scale AI CEO on Meta’s $14B deal, scaling Uber Eats to $80B, & what frontier labs are building next
Sherman: Always fly out to meet enterprise customers in person
“My number one piece of advice is just get on the plane. Always get on the plane, go meet with your customers. It never makes sense. No one wants to get on the plane. It's always like, well, this is an informational meeting. Why do I need to be there in person?…”
Alex Sherman Oct 6, 2025 ▶ 43:31 He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex S... · PMF Show
Dwivedi: Enterprise AI conviction requires production testing, not staging demos
“Everybody, the reason nobody gets convinced on staging environment is that everybody thinks that their environment is unique, right? Like it's the most complex thing on earth. So they're like, can your AI actually figure out the complexities of my system? Alth…”
Raaz Dwivedi Oct 5, 2025 ▶ 43:51 ⚡️Traversal: Causal ML and Reinforcement Learning
IN DEPTH Insight
Sekar: Enterprise Sales Require Selling Change Management and Peace of Mind
“Actually being able to make change management part of our pitch was super helpful, right? Especially in the enterprise, being able to say, we have the technology, but we will also help you be successful with it. You can get this done end to end in X months, ri…”
Kiren Sekar Sep 11, 2025 ▶ 57:57 Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)
a16z Disclosure
Scharfstein: Scale AI allows large enterprise clients to retain their IP
“Oftentimes the big customers want to retain the IP. We're very happy to allow them to retain that IP because, you know, it's core to their business.”
Ben Scharfstein Aug 26, 2025 ▶ 23:35 How Scale AI is Pioneering the Future of Work
Lloyd: Centralized admin controls are the primary demand from enterprise buyers
“Having the team concept also makes it easier for us to do enterprise-wide sort of like admin controls, which is honestly the, probably the biggest thing that they want is they want, like, they want to enforce that everyone's on a team, that they sign in with S…”
Zach Lloyd Jun 25, 2025 ▶ 42:45 ⚡️Warp 2.0: the Agentic Development Environment - Zach Lloyd and Ben Holmes
SAASTR Insight
Nithrakashyap: Ignore startup advice to say no; say yes to everything
“I know there's this advice that say no to a 95%. I don't believe in that. I think you have to say yes to yes to everything, right? Because if you lose, if you miss a large fortune, 500 customer, it may be a hundred K deal down the road. That's a 20, 30 X lifet…”
Arvind Nithrakashyap Jun 25, 2025 ▶ 8:24 AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO
IN DEPTH Insight
Song: Rigid quarterly roadmapping prevents startups from becoming trusted customer confidants
“That I think is why it becomes difficult for them to become this trusted confidant, because you're never going to move fast enough to actually seize on an opportunity they have. Like, If a customer has a burning problem, they're not going to wait a quarter for…”
Rick Song May 8, 2025 ▶ 46:25 From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
MAD Assertion Not checkable as stated
Internal study: Enterprise clients touch only 0.1% of warehouse data tables
“So we looked at all of our enterprise customers Table utilization over a 60 day period, and .1% of the tables in their warehouses were ever touched.”
Mike Palmer May 1, 2025 ▶ 26:51 Dashboards Are Dead: Sigma’s BI Revolution for Trillion-Row Data
IN DEPTH Assertion Not checkable as stated
Early corporate customers bought 1Password as employee gifts before securing business assets
“Earlier on in the first couple of years, you'd have some companies that would buy copies of one password for all of their employees for Christmas to keep their employees safe. And then it started to change for some of the companies, not many, but some of the c…”
Jeff Shiner Apr 24, 2025 ▶ 17:46 1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
TBPN Opinion
Crivello: High-revenue enterprise AI startups are becoming modern shelfware
“There are some very hot AI startups out there in the enterprise that are basically shelfware. Like, their revenue is skyrocketing, and they're meeting very little adoption internally.”
Flo Crivello Apr 10, 2025 ▶ 15:18 What AI and LEGO Have in Common | Flo Crivello on TBPN April 7th
a16z Insight
Jain: Showing AI agents' step-by-step execution builds customer trust
“It's like here's step by step everything it's doing. And the design for that was really interesting, right? Because if you run that agent again, it might do slightly different things, right? But really taking the user along for that journey to be like, hey, th…”
Prabhav Jain Mar 20, 2025 ▶ 21:54 The Future of Digital Workers
THE PITCH Assertion Not checkable as stated
FolioWorks just signed three enterprise clients with over $1B in revenue
“So we just closed our first three very, very large companies. So like companies that have revenue of a billion plus.”
Kathy Wong Mar 12, 2025 ▶ 31:53 The $1.2 Billion EdTech Opportunity Nobody Saw
Lieberman: Agencies face strong incentives to move upmarket to enterprise clients
“I've generally found that every agency feels a general incentive to move up market, because as you move up market, your deal sizes with larger customers are bigger. Larger customers also generally have more budget and more resources. They're more responsive. T…”
Alex Lieberman Mar 12, 2025 ▶ 19:01 7 tactics for non-cringy sales
SAASTR Assertion Not checkable as stated
Stripe's enterprise customers buy at least two products on average
“So our enterprise customers on average buy at least two products for Stripe.”
Jeanne DeWitt Grosser Feb 12, 2025 ▶ 20:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO
PRODUCT MARKET FIT Assertion Not checkable as stated
Enterprises pay up to seven figures for cloud-cost optimization software
“Like we talked to dozens of customers and evaluated the big enterprise will pay high six figures for a solution like that. And even seven figures for the bigger enterprises.”
Alon Arvatz Feb 10, 2025 ▶ 33:20 He exited for $335M—& felt "emptiness". So he quit, gave up millions in earnout, & grew to $1M AR... · PMF Show
20VC Insight
Dines: Enterprise clients prefer automation workflows to fail rather than be 'too smart'
“Look, one story that I keep hearing from our customers is they prefer our workflows to fail than to be too smart. Because their risk appetite for this type of workloads, it's low.”
Daniel Dines Dec 18, 2024 ▶ 17:06 Daniel Dines, UiPath CEO & Founder: Why Agents Do Not Mean RPA is F*** | E1240 · 20VC with Harry Stebbings
SAASTR Assertion Not checkable as stated
Boehmig: Ironclad Customers See Tens of Millions in AI Business Value
“We're working with customers who are seeing tens of millions of dollars in attributable business value to speeding up attorney workflow, doing things in house that they used to have to send out out house.”
Jason Boehmig Dec 11, 2024 ▶ 12:21 5 Things That Are Working and 5 Things That Aren’t in B2B SaaS AI with Ironclad's CEO and a16z
a16z Insight
Amble: Enterprise AI agent adoption lags due to higher quality standards
“As you get to more enterprise customers, a level of quality matters a lot more. And so I think they're probably a little more hesitant. And they've got, you know, organizationally, they have big, big teams. They're relying on certain processes. It's a change i…”
Seema Amble Nov 21, 2024 ▶ 7:16 How GenAI-Based Software Is Advancing Marketing and Sales
20VC Assertion Not checkable as stated
No enterprise has fully figured out its AI strategy yet
“Absolutely. I think, like, no, any company that's gonna say, oh, we figured out what we're doing with AI, I don't think they're, I don't think they figured it out.”
AJ Tennant Oct 23, 2024 ▶ 19:14 AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
MAD Assertion Not checkable as stated
Hitchcock: Enterprises adopt SurrealDB for isolated problems, not to replace systems
“They're not coming to us and saying, I'm going to replace four different databases that I've spent the last 10 years implementing. It's usually being able to solve one problem to begin with, and that problem is usually that they're having to work with many dif…”
Tobie Morgan Hitchcock Oct 3, 2024 ▶ 33:25 Building The Database That Can Do It All | Tobie Morgan Hitchcock, CEO of SurrealDB
SAASTR Insight
Riparbelli: AI video value comes from replacing text, not studio production
“I would say the two big aha moments was, the first one was like, people are not replacing video production, they're replacing text. That's very fundamental to our understanding of like, why this product is valuable.”
Victor Riparbelli Sep 18, 2024 ▶ 32:23 From 0-50,000 Customers: How to Build a GenAI Company for the Enterprise with Synthesia's CEO
Corporate venture money cannot guarantee startup longevity to enterprise buyers
“Investment has a limited liability, meaning that you just put in money, and the worst case scenario, you lose the money. So from the customer's perspective, okay, you have an investor, large investor, that's good for you if you are a startup, but that doesn't …”
Sokwoo Rhee Sep 17, 2024 ▶ 15:37 Sparking Net New Innovation At Massive Scale — With LG's Sokwoo Rhee
BIG TECHNOLOGY Disclosure
LG Nova packages startups into co-created LG entities for enterprise buyers
“We jointly create the business. LG creates our own business, which we call ourselves a NewCo or CMBU, and startups become part of it, becomes the integral part of the business. So when it go to the big customers, we don't just go to go there as a startup. We g…”
Sokwoo Rhee Sep 17, 2024 ▶ 16:04 Sparking Net New Innovation At Massive Scale — With LG's Sokwoo Rhee
Selling General-Purpose AI to Enterprises Causes Customer Indecision and Paralysis
“And I think that actually has a big downside when you're actually trying to sell something packaged like that to businesses, which is that you're giving them this Swiss army knife of a tool that has all these general capabilities, and the risk is that your end…”
Parmy Olson Sep 13, 2024 ▶ 9:02 Is OpenAI’s New “o1” Model The Big Step Forward We’ve Been Waiting For?
LATENT SPACE Assertion Not checkable as stated
Pullen: Enterprise customers are growing more willing to share proprietary codebases
“Mostly we've actually seen, I'd say people becoming more amenable to the idea over time, actually rather than more skeptical, because I think they can see the upside.”
Alistair Pullen Aug 22, 2024 ▶ 20:43 Is finetuning GPT4o worth it?
Blomfield: Enterprise Buyers Are Typically Wary of Uncapped Usage Pricing
“People typically are wary of totally uncapped usage-based pricing, so you might want to put a cap on that.”
Tom Blomfield Jul 25, 2024 ▶ 8:28 How To Price For B2B | Startup School · Y Combinator
Weinstein: Demand upfront money before building custom enterprise features
“If we're super serious about this, send us a million dollars. Like wire us a million dollars. We'll happily wire it back anytime you need it, but let's actually Put some stake in the ground about the value. And I find that in the cases in which they're like, w…”
Jeff Weinstein Jul 11, 2024 ▶ 41:40 Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)
BIG TECHNOLOGY Prediction Held up
Wood: Most enterprises will fine-tune existing models rather than build foundation models
“There isn't one model to kind of rule them all. Each different model has, you know, different sweet spots, and it's my expectation that most customers will invest in not building the foundation models, but will invest in fine tuning and improving those individ…”
Matt Wood Jul 10, 2024 ▶ 20:35 Amazon's Longterm AI Vision — With AWS VP Matt Wood
Koomen: Quoting Too High Rarely Scares Off Genuinely Interested Customers
“One of the most surprising things I learned was that when a customer really wants your product, it's hard to scare them away by quoting a price that's too high.”
Pete Koomen Jul 8, 2024 ▶ 16:37 Enterprise Sales | Startup School · Y Combinator
20VC Insight
Bialecki: Going public gives larger enterprise customers confidence in long-term stability
“As we were working with larger businesses, larger customers we knew there was some value in folks knowing that like, Hey, we were in it for the long run.”
Andrew Bialecki Jun 26, 2024 ▶ 38:05 Andrew Bialecki: Is Klaviyo the Most Under-Priced Public Company? | E1170 · 20VC with Harry Stebbings
20VC Insight
Arora: Enterprise customers will not tolerate experimental products long-term
“The enterprise customers have slightly different standards and expectations because they're highly unlikely to last too long on an experimental set of products.”
Nikesh Arora May 20, 2024 ▶ 14:20 Nikesh Arora: Lessons from $102BN Market Cap & How to Create & Sustain Competitive Advantage | E1155 · 20VC with Harry Stebbings
Kumar: Enterprise tire-kickers will not spend time testing free software
“These folks, at least in the space we play in, they won't give you the time. They don't have the time to give you. You're asking for real time, right? Maybe one hour a week, You know, installing the software in their environment, asking for feedback and all of…”
Poojan Kumar May 6, 2024 ▶ 23:29 He raised $11M off a deck. Here's how he launched Clumio & grew 4x to over 8-figures in ARR. | Po... · PMF Show
20VC Insight
Enterprise SaaS customers require systems integrator partners for implementation
“When you're building for the enterprise customer, they are not going to do it themselves. You need an SI partner who will be trained to use it.”
Girish Mathrubootham Apr 19, 2024 ▶ 23:57 Girish Mathrubootham: Biggest Product and Pricing Lessons from Scaling to $597M in ARR | E1142 · 20VC with Harry Stebbings
Lemkin: Business customers can process at most two major releases yearly
“The maximum a customer can process is two big releases a year and maybe quarterly.”
Jason Lemkin Feb 18, 2024 ▶ 1:13:37 Building a world-class sales org | Jason Lemkin (SaaStr)
Evans: Customers should not be expected to figure out AI's utility
“It's not the customer's job to know what the technology is for. It's not the customer's job to have be given a ChatGPT account and told, there you are, go off and reimagine how your company does its backup of its processes.”
Benedict Evans Jan 29, 2024 ▶ 8:50 What's your AI strategy?
20VC Insight
Trade Contract Discounts for Written Customer Reference Agreements With Early Clients
“Think very carefully on when you're negotiating these terms with your first 25, say, enterprise customers, give and gets. You're going to need their help to get this going. So give them the concessions that they need. Make it worth their while and get it in wr…”
Sean Murray Jan 24, 2024 ▶ 39:48 Sean Murray: Why Discovery Today is F***** & How to Scale Into Enterprise Effectively | E1107 · 20VC with Harry Stebbings
MAD Insight
Goshen: Enterprise customers heavily prioritize LLM portability across multi-cloud environments
“I was surprised how much customers care about having the portability and capability of working with a single vendor that can run under different cloud, but not only cloud, other environments as well.”
Ori Goshen Sep 20, 2023 ▶ 24:51 Beyond ChatGPT: Ori Goshen’s Playbook for Building Neuro-Symbolic LLMs
True enterprise product-market fit is when early customers advocate your vision
“Having our first enterprise customers not only be happy, but willing to be advocates to our future customers and talk about the vision as if it was, yeah, it's not just our vision, it's their vision and that's how they talk about it.”
Nabeil Alazzam Jul 17, 2023 ▶ 44:23 Nabeil Alazzam, Founder of Forma.ai | How the First Enterprise Sale Leads to Product Market Fit · PMF Show
20VC Assertion Not publicly verifiable
Weiss: Over 85% of Slack enterprise customers originate through self-service
“Over 85% of our enterprise customers, so, you know, customers of over a thousand users, started in self-service. So they didn't call up our sales team didn't call them. They started by signing up on slack.com, like, just like an SMB, sharing it with some co-wo…”
Noah Weiss Jun 16, 2023 ▶ 38:42 Noah Weiss: How to Master Product-Led Growth; Scaling PLG to Enterprise at Google & Slack | E1026 · 20VC with Harry Stebbings
Walling: Enterprise software should be priced at minimum $25K-$35K annually
“My rule of thumb is charge a lot because enterprise customers are a pain to deal with in terms of procurement and all that. So I think minimum 25 K 35 K on the bottom end for these types of deals.”
Rob Walling Apr 4, 2023 ▶ 17:28 Episode 655 | Seat-Based Pricing, Can Churn Be Too Low? and More...
TOP FOUNDERS Assertion Not checkable as stated
M-Files contract sizes range from $5,000 to over $1 million annually
“And in that kind of partner business segment, the typical annual prices would be a few, few thousand dollars, let's say five K. And then we go up to our enterprise customers who pay well over a million per year.”
Antti Nivala Dec 18, 2022 ▶ 5:13 This founder hit $90m ARR last week, took $30m secondary in last round for Document Management SaaS
Epstein: Underpricing B2B software signals low value and untrustworthiness
“The low price was signaling to their customers that maybe their product wasn't valuable, or it couldn't be trusted in the long term.”
Aaron Epstein Dec 15, 2022 ▶ 30:08 Startup Business Models and Pricing | Startup School · Y Combinator

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