Shadowing Practice: 24 Hours Inside a YC AI Startup - Learn English Speaking with Video
Creating lesson...
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We have a thing that is extremely useful and is used by a lot of companies, a lot of enterprises, and it's growing quickly.
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The question is, there's this window where AI is taking over the world of research
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and we are kind of at the forefront.
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We need to take advantage of that and grow extraordinarily quickly.
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We are not happy with little amount of growth in this stage.
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We need to be having massive growth.
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In the world of startups, most people think raising venture capital is the hardest part, but in reality, it's not.
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The hardest part is what happens after.
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When the money is in the bank, the headcount doubles overnight and every investor is watching to see if you can actually scale.
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How do you actually talk to enough people to get a compelling answer to your question?
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And there is just no way to do that.
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And so this ability for AI to actually run these interviews, talk to users for you, connect those dots for you, across thousands of people, is just infinitely more powerful.
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With pre-seed and seed investing, VCs are betting on the founder, the idea, and their conviction.
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But by Series A+, they're betting on a machine.
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It's a little frantic.
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It's a big design question, design problem that we don't have yet a solution for.
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Kind of the core point of this is that this feedback has been coming up over and over and over again.
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This is the defining moment of a company like
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that where VCs are determining whether there's enough conviction in the market for their product.
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They've raised the capital, but now the hardest part comes to light.
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And the real question is, can they scale fast enough?
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Today, we're actually catching up with Michael Hess and his co-founder Aaron from Outset AI.
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They are an AI moderated research platform.
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They actually just raised a $30 million Series B.
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They've gone from roughly seven people to 45 in the last 12 months, which is an absolutely insane headcount change.
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And they're currently dealing with the aftermath of that, which is finding new office space and moving into that new office.
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So I'm gonna go check them out and hang out with them at a really crucial time.
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Hey, if you have any forover tips, drop your X in the comments.
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Adam Adam hi.
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Will, lovely to meet you.
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Adam is our most tenured account exec and core part of the team.
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The average tenure of an outside employee right now is like two months, something like that.
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We've had a lot of people in the last three, four months.
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I think we were 20 people in December.
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Yes, I think I was 12.
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You were 12, yeah.
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And now my third office, which is crazy.
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Yeah, that is crazy.
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You've been here eight months and you've been through three offices.
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Yeah, we outgrew this office way faster than we thought we would.
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This was our revenue thermometer in YC.
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We did the summer 23 batch.
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Goal is 150k by end of batch.
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So I drew this very crude thermometer that we had hanging in our first office.
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You can see first deal eight and a half thousand plus ten thousand plus two and a half thousand.
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I mean tiny deal sizes, but we filled it up and then Jessica, our office manager, had the idea to frame it.
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And so we put it up.
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It's kind of like art gallery style, like with the light above.
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Yeah, literally. So cool.
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If you were to give the audience like a sum up in one sentence of actually what Outset is, could you run me through it?
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We're a qualitative research platform, so we serve market research and user research teams primarily at enterprise companies and help them better understand their customers.
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We have an AI moderator that will actually conduct user research interviews, dig in deeper, ask follow-up questions.
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A big thing for us is we're not replacing humans.
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You'll see that in like our out-of-home advertising.
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The tagline was Listen to humans, don't replace them.
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We're away from the team now.
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What's actually going on for you guys?
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You've grown exponentially.
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You're moving into a new office.
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Tell me about it.
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of software is infinitely scalable, right?
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You can write code and build a product that's useful to people.
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And if you are lucky, you can scale up to hundreds of millions of dollars in revenue almost overnight, tens of thousands, millions of users.
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But you can't scale physical office spaces infinitely.
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We are bursting at the seams in our current office, which is why we're moving to this new one.
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It's about double the size.
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We have enough desk space, but the meeting rooms end up being really crowded.
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So, actually, that's our ad.
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I see you there.
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Were you a firefighter before?
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Yeah.
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Right after college, I went to Fire Academy and then started working as a volunteer firefighter up in Lake County.
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And I did that for three or four years while I was at another tech startup, actually.
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The plan originally was to go be a full-time firefighter, but I kind of got pulled into this startup, worked there for a number of years, did firefighting on the side.
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I'll never be the guy to post on LinkedIn five things firefighting taught me about how to start a company.
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B2B SAS.
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There's a thing called ICS, which is the Incident Command System.
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It's just like scientifically developed to be a highly efficient way to run an incident.
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And so we draw from that in like how we treat incidents in our code base or at our company.
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There's a clear incident commander.
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We have clear roles and responsibilities, clear channels of communication.
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There's an old joke that's like, how do you, how can you tell us when it's a firefighter?
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They tell you.
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I feel like as an investor, like I would say there's certain qualities and discipline that come with something like that.
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Like you're in extreme environments all of the time.
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You must have such a high level of emotional intelligence to be able to deal with people in those situations too, right?
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Like it's high pressure all the time.
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Yeah.
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Yeah, this is the new office.
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It's about twice the size, so we're pretty excited to move in.
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What are the challenges for you guys right now as you're growing?
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There's two main buckets of challenges.
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There's kind of the standard hyper-growth challenges.
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Any company is going to go through growing pains when you add as many people as we're adding.
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The other bucket is maybe unique to AI companies, which is just staying on the bleeding edge and pushing forward with product and making sure that,
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you know, we are doing things that were never possible before.
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I think that's the only way to win in this market, right?
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If you look at any AI company, like there's no software emote anymore because you can write software in a matter of hours with cloud code and whatnot.
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I use this analogy all the time.
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Like what it feels like right now is we're on a boat where someone's broken the throttle off
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and it's jammed at 100 and there's no way we can slow down.
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All we can do is steer around the icebergs.
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If you look on X or whatever, right?
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VCs, but also aspiring founders and all the rest, right?
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They're seeing so much noise on social media platforms about what's changing with AI.
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How are you staying focused during this period while the shiny ball syndrome is literally everywhere?
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Stay off Twitter.
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Stay off X.
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I'm quite good at compartmentalizing, and so is Aaron.
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You have to be able to take in the data around you.
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And remember what really matters is do our customers find our product useful?
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Are we able to market the product, and are we able to close new customers?
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That's really what matters.
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Nothing else matters.
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Fundraising doesn't matter.
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And if we're not doing those things, then we shouldn't be a company.
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Just went over to the new office.
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It's fully painted.
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Wi-Fi is installed.
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We are good to go for Monday. So, woohoo!
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Super exciting.
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Yeah.
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Yeah, go to the office.
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Before we get a normal stand-up.
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So as some of you know, we're calling another Code Purple.
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For those who don't remember what that is, Code Purple is like we have enough data that we want to go focus on something, and even at the expense of other things.
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So it's like extreme focus for a couple of weeks.
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What's the purpose of the Code Purple meeting after?
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Give it a reminder, we had conversations last night.
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Right.
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My take is that in the stand-up, we talk about the Code Purple.
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Maybe I'll take it.
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The important part is that we are framing it in a motivating way.
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This is an exciting thing.
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It's a little frantic.
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In that kind of spirit, we got a few bits of data
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that came in around the same time last week about some opportunities for us to improve a certain price of our product.
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We're still scoping out exactly what we're going to do, but there was a lot of talk late night in the office last night, in the morning, on Slack,
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and so we are going to go heads down on that for a little bit.
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Thanks, everyone.
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Let's have a great day.
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It's just nice having everyone together, you know?
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And it's fun to get to see everyone's faces and then it's just easy to disseminate this stuff.
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Instead of over Slack, it's just so much better to be able to say it to everybody.
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Hell yeah.
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Our jobs to some degree are leading this group of very exceptional people.
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So that means having the right leaders, giving them the right kind of opportunities, pushing people in the right direction.
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We're doing a really intense sprint on a subset of features because,
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hey, we have enough data now that we can like really focus in on like two or three features.
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So we're going to drop everything and just focus on that.
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Right.
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And so like that's us having enough understanding and context
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and finger on the pulse of the market that we can like make
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that call and focus our resources on a couple of things.
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We need to be doing that.
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We should talk about what we want to build and making sure
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that the things we are building have the most disproportionate impact.
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Kind of the core point of this is that this feedback has been coming up over and over and over again.
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And so I would love for none of us to ever hear this again.
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And so whatever we do, hopefully we do it with that in mind.
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So we are doing a sprint, and we're doing it fast.
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As we identify the points, we will obviously scope to what are we going to ship in the next n weeks.
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But the end result must be a coherent user experience.
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Yeah, I think what I want to use this exact meeting
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for is there's these kind of two main work streams in my, like maybe three main work streams, and just what do we actually want to do in these and discuss.
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I think very broadly, what we started just circling around yesterday.
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It seems like there are kind of three big areas that we can improve and like the problems.
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Latency, speed, guide creation, and editing.
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We've just stepped out of this code purple meeting
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and Michael earlier in the day had a fair bit to say about the general team culture here.
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It's one thing to say, but it's another thing to see in action.
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One of the key points I've just seen is we're in this morning standup and they're talking about this code purple, which is essentially like a sprint briefing.
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It's urgent for them.
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They're going to knock off a bunch of resources from the dev team to actually pull this all together.
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But the important part was how they addressed the team and how they positioned what this was about.
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And it was really cool to see.
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So Aaron said, this is an opportunity.
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We've gotten some amazing feedback here and we can now innovate on the product.
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Essentially, it's product improvements that they're trying to implement here.
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But he could have taken that in a very different direction.
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He shaped it in a way for the team to go, wow, okay, that's so cool we're growing and let's innovate on the existing product and let's make this better
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one of the reasons that I love working at outset
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and working at a startup is having those types of meetings
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where we have a roadmap for this quarter right like sometimes information comes in
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that changes that and we have to adjust on the fly.
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But I think the core tension is how much do we want to be band-aiding
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and fixing something versus how much do we take a beat, take even a day, and just like think about okay where does this get us to where we want to be in three months, six months, nine months down the line.
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That's in our DNA as a startup, as a research startup, and as a startup just in general is okay how do
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we figure out who we need to actually go talk to and get feedback on this.
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Launch the best version of this.
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The reason that we win is how insanely, not just customer obsessed we are, but research obsessed we are within the community, how we show up in the community,
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how we engage people in the community, how we build for them.
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That's why we show up very authentically in the way that we go to market and people really resonate with that, especially with this audience.
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I've loved working in the research space because they're such authentic people.
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Okay, here's my favorite advice for Young Founders is if you want to start a company, just decide you're going to start a company quit your job and then figure out what to build.
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You don't need to, the number one thing I hear from people who are thinking about it are like, I'm waiting for the right idea.
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I think the right idea is never gonna just like hit you.
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You're going to like spend all day obsessing over interesting ideas and then go build something.
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But you gotta have all day to do that.
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So quit your job and go do it.
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It's a hard journey, but if you do a good job
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and you're lucky enough to build a company where people choose to plant their flag with you and join the journey, have fun on it.
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The problem is if you want the 20K, that's a bad idea.
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You have to catch all 20K.
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We're putting the camera off.
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What are we doing this all for
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if not to build something really cool with a bunch of really great people
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and produce a company and a product we're really proud of?
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Who Will Love This Video?
If you’re an English learner aiming to boost your English speaking practice—especially for real-world business conversations—or prepping for IELTS speaking practice, this video is gold. It’s perfect for intermediate learners ready to tackle fast-paced, professional dialogue. You’ll pick up how to talk about growth, startups, and challenges in a natural, confident way—skills that shine in interviews or work settings.
Words & Idioms to Add to Your Toolkit
- At the forefront: Leading the way. Example: “AI is at the forefront of modern tech.”
- Scale fast: Grow quickly. Example: “Startups need to scale fast to stay competitive.”
- Aftermath: The result of a big change. Example: “They’re dealing with the aftermath of hiring 30 new people.”
- Tiny deal sizes: Small business agreements. Example: “Their first sales had tiny deal sizes, but they grew.”
These phrases are everyday business English—steal them to sound more fluent!
Nail the Pronunciation: Tips for This Speaker’s Style
The speakers in the video talk quickly with a casual, professional tone. To mimic them, focus on connected speech: link words like “kind of at” (kinda at) or “a lot of” (alotta). Use a shadowing app like Shadowspeaks to repeat short clips—pause, then say the line aloud immediately. Pay attention to how “venture capital” is stressed (VEN-chur CAP-i-tal) and the rise in intonation when asking questions like, “Can they scale fast enough?” This practice will make your speech sound more natural, whether you’re using it for learn English with videos or real conversations.
Pro tip: Start with 10-second clips. Master the rhythm, then move to longer sections. You’ll be surprised how fast your fluency improves!
Grammar in this video
The structures the speaker uses most, with the exact words from the video:
| Structure | In the video |
|---|---|
| Present perfect continuous have/has been + -ing — an action that started earlier and is still going on | has been coming |
| Relative clauses who / which + clause — extra information about a person or thing | months, which is · that, which is · office, which is |
| Present perfect have/has + past participle — a past action that still matters now | They've raised · They've gone · You've been |
| Passive voice be + past participle — the focus is on what happens, not who does it | being really crowded · is installed |
What is the Shadowing Technique?
Shadowing is a science-backed language learning technique originally developed for professional interpreter training and popularized by polyglot Dr. Alexander Arguelles. The method is simple but powerful: you listen to native English audio and immediately repeat it out loud — like a shadow following the speaker with just a 1–2 second delay. Unlike passive listening or grammar drills, shadowing forces your brain and mouth muscles to simultaneously process and reproduce real speech patterns. Research shows it significantly improves pronunciation accuracy, intonation, rhythm, connected speech, listening comprehension, and speaking fluency — making it one of the most effective methods for IELTS Speaking preparation and real-world English communication.