쉐도잉 연습: 24 Hours Inside a $47M YC AI-native Insurance Startup - 영상으로 영어 말하기 배우기

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kind of scares me.

I don't want to become the bottleneck of this company that I'm constantly figuring out what everything is going on.

That's not a good way to run a company.

We can't ever make a billion dollars like that.

That's never gonna happen.

For years, the obvious way to build an AI was to sell tools to an industry.

But the best founders have evolved past that.

They're using AI to become the business itself and taking the revenue that used to belong to the incumbents.

The startup I'm visiting today is doing this in one of the oldest industries there is.

We have to be fully in control of the funnel.

What's happening is that the funnel is in control of us.

And there's a lot of smart people here, so we can take control of the funnel.

Until that thing gets out to market, or until somebody bought it, it's in our hurry.

I don't love the outcome, I'll be honest with you.

I have to make this company exist beyond me.

Today, I'm going behind the scenes with Harper, an AI native commercial insurance startup in Silicon Valley.

A traditional broker takes weeks to source quotes and find a business the best price on insurance cover.

Harper uses AI to do it in as little as a day or two across more than 160 carriers.

Week is too long, I would say a day is a goal.

They came through Y Combinator's winter 2025 batch

and raised 47 million in a combined seed and series A led by Emergence Capital.

Almost think of it as like when you boil water, at some point the water starts spilling over.

That's us every day.

Insurance is a demand capture business.

Literally every business in the country needs it.

So demand was never the problem.

The real question lies in understanding whether they can build the back end fast enough to capture it and venture scale.

So you may notice that it is super, super early in the morning.

It's not nighttime.

This is morning light right here.

And the reason we're up so early is

because we're going behind the scenes with a company with a work ethic that we have not seen on this channel yet.

We're going behind the scenes with Harper, an AI native insurance startup based here in San Francisco.

They've raised a 47 million combined seed and series A.

And these guys are on a complete different level.

When I was on a call with them, you know, I was gonna come in at about 8 a.m.

That's usually when I like to come see startups.

And they said, hey, we get in at like 5.15.

I was like, okay, I'm gonna get in there with you.

The hats just keep showing up in different places.

Like, there's a hat here, there's a hat off the charge desk.

For a bit of background context, Dakota wears hats all along, apparently.

And just like, leaves little crickets around the office.

Yeah.

We have another email going out today that'll just be like, hey, just a reminder, like, we saw this, and then if you'd like to get in touch with us, and then the plan is to give those guys a call tomorrow.

Did everybody see that?

Does anybody have any questions about it?

I have a comment.

Yeah.

For contractors, I feel like for all of them, we can just reach out for Inland Marine.

Yeah.

And just let them know, hey, if you need your tools and equipment covered, we can get that handled for you.

And then for the higher rev accounts, we can start talking about some professional liability.

Maybe also looking into accounts with actual employees, a specific payroll, maybe specific industries where we can look into the workers comp.

This is the end of the month.

So typically this should be our busiest week, right?

A lot of people need an August 1st start date.

So really push for that.

Send emails, text messages, calls.

We need to get people aware that if they want to start date for August 1st, they really should be paying today, tomorrow, Wednesday.

Yeah, yeah, yeah, get ahead of me.

Yeah, right.

All right, just stepped out of that morning kind of sales briefing.

Again, early in the morning, it's like 6.30 AM.

The team is on it.

Like, they are powering ahead.

And I'm like, wow, okay, I need like two coffees.

All right, so now I'm looking at this thing Let's see is the funnel getting leakier.

I feel like maybe we have 14 construction contractors Nine ISC quotes one same day bound and seven applications built.

What does this mean?

So now I'm nervous Let's get it going

And I heard there's some parsing issue now So

that one was like with Vince new changes He makes the parsing like more like synchronous

So what happens is that it's happening like at the same time

So what I'm gonna do is I'm gonna refresh it

and figure out why I think it's getting like there's like a lot of volume so it's probably getting like clogged somewhere.

So I'm gonna figure out what's going on there.

Tell me what that means.

So I'm manually having to type in the premium for each of the quotes, when normally it would automatically have its own line item.

So I'm just adding a line, which is, I mean, it doesn't really matter, but from a, let me just show you from an email perspective, if I'm sending a normal quote,

this wouldn't look like this.

It would have the specific line of coverage.

Oh, now it says fees and taxes.

Now it just says fees

and taxes it's not parsing properly okay basically what's happening right now

which is fyi is when you send out the quote they have to manually type everything in

because whatever finn did with the parsing is fucked up

so basically it's like it just shows fees and taxes

so you send provide a ten thousand dollar quote it looks like you have ten thousand dollars fees

and taxes so i think arian's on it

but just make please like please be on top of that

because that's really problematic for the conversion yeah

because it just looks like all you're doing is paying fees

and taxes to send the 8 30 products say okay cool

and then let's make sure we have our good a good

sense of what what our agenda for that's going to be

so we can model what we want to see in the world, which is good agendas.

Okay, let's think.

Are we getting more things that are like good and going straight through and quotable?

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And I was doing some of the board deck prep though I was kind of like thinking through, like the first pass rate is one measure, but then it's kind of like the quote rate because sometimes people still will have questions regardless,

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like just a simple question that we might be able to answer ourselves.

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I believe the right metric for this is like how many quotes are we getting back

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and how fast versus the first pass rate.

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Like the first pass rate is like a starting indication of like the bigger thing, which is just like, are we getting more quotes back and are they coming fast?

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If you're defining first pass rate as like the first pass rate we're tracking, that's like how good the intake was done, right?

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Yeah.

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So then I almost imagine like follow-ups and the number of follow-ups and then how fast we get the quote back, like a combination of those two sort of determine whether the app checker skill is actually.

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Yeah, I agree.

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We should take this part of the conversation

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and curse the curse the curse the curse the curse the curse

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or we should have a little bit more Interaction with AI and figure out what's a good answer for this?

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I really want to explore this little more

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because I want to make sure we're tracking to the right KPI first pass rate alone I think is a bad one.

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Okay, cool.

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So we got that all done.

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Do you have breakfast?

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No, I don't have breakfast usually Oh, well just keep the energy levels up.

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I feel like breakfast takes it and sucks your energy away Really?

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Yeah, it's weird.

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I really enjoy just you know a load of caffeine in the morning Interesting.

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So are you saying like espresso coffee or brew coffee?

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What's the vibe?

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You know what?

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My wife's not gonna like this, but energy drinks.

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C4.

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I know, it's dangerous, scandalous.

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I was just with Dakota in the meeting.

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He's just briefing before this meeting we're going into.

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And he says, Cursor Cursor Cursor.

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What is that?

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Oh, okay.

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So one of the things that we're doing in the company is that we monitor everything all our emails, our phones, text messages, they all kind of flow into a central place

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because we want to have the knowledge building of the entire company and not have tribal knowledge in different places.

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Now, when we have granolas, Dakota is saying, cursor, cursor, cursor, because his cursor literally will be continuing to process everything that he's saying and he's going to send him reports.

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So in many ways, he's just telling his cursor that, hey, this, by the way, please listen, tune into this thing so that you can give me an answer to this.

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Oh, cool.

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So it's a hookup, a ticker no-off.

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First party, yeah, Cursor is almost like a first party thing here.

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So a couple of things.

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Ever since we met over the last many weeks, everyone has been using Cursor.

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So we have both engineering operations.

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We have started getting ops to be able to really build out their own applications as well.

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So kind of moving, engineers are moving towards more like, let's build a software factory.

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And so then the operators are going and building their own applications.

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And by doing so, they can move faster.

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Right because they already know their pain points very well.

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They know what's the problem So they can go ahead and like build these applications out and they can unblock themselves.

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Dude.

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All right real quick Let's try this.

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Let's let's give this a go All right, cheers.

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Cheers Holy shit, that's really good.

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It is really dangerous.

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It's like cordial Team I tried my first seatbelt this morning by the way.

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How do you like it?

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That's a good move.

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It's crack.

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It's crazy.

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This thing is like, I'm already like shoving my hands like this.

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If you start beating ants on your skin.

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Can you help me understand where we are with like launching more verticals on the voice AI piece of it?

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Um, let's see if we can start there.

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Cause I also saw something over the weekend where it's like, you're able to do workers' comp alongside these things and others.

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So maybe walk me through what the product has developed to over the weekend and then what we're thinking for today.

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Correct.

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Over the weekend, we actually added three more verticals.

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Also, each vertical is down.

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Where are they?

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We added retail, smoke shops, and consultants.

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Okay.

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Each vertical is now able to take the general application as well as cyber, workers' confidence property.

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So if the customer wants all four lines, we're able to do that on this platform.

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Right now, the plan is to keep testing them for the day with the real customers.

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I've tested them all night yesterday.

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The idea for this week is to finish up to 10 verticals.

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There's no reason why we shouldn't take every call out there

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right now in any vertical we can do with Voice AI taking it end to end.

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Because in theory, it's like there's no capacity constraint and we need to just quickly figure out if it's working or not.

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We need a massive signal.

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So my view is that Anas should be sitting there all day with like 50 calls, like in the ideal world.

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50 calls going at one time.

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I mean, we should take every single thing we can get on.

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And literally just make sure you asterisk it.

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It is an R&D budget is a true literal non-marketing R&D budget.

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It is literally get this guy as many voice AI calls as possible so we can see the thing works.

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I would think about it on par with like the spin we have on LLMs

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or something like that in terms of how how much it can grow.

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So that's a top priority.

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I know for sure we can bid a lot for retail.

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I know we can bid a lot for consultants and make sure that we get it done.

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Even if it's four or five hundred dollars per one

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that we get in the categories that he can now actually do on the voice AI, the number one priority that we have is make sure

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that we completely get it fully tested and buy every single thing that you can.

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Another feature that was implemented over the weekend was if the customer gives us their phone number, we're able to capture all the information so we don't have to actually,

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because we we just wait six to seven minutes on just getting the company's name The address all

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that so now it's all eliminated with the phone number

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We're able to refill the application of what we have in big brother Okay, the other thing I would say is

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that like I need more You know I get nervous because you're also have doing sales consumes out today.

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There's a you're doing the sales anyway There's a lot going on

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but if you hear the actual thing that's the most important for us to scale the top of funnel I mean, if the voice AI can do a full intake itself,

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it's already able to do workers comp, cyber, and all this other stuff.

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I cannot really think of a place that should be more well-resourced.

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It's literally able to do all the calls.

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So in my view, I think that the speed of getting out the next one is seemingly a little slow.

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It sounds like there's so many things being done, but this is a super critical focus area.

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So I would just say in general, I think resource reallocation a little bit.

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I would leave it to Karin and to Shara to think a little bit more about what that looks like.

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But I would really reallocate some of the focus because this sounds like it's working quite well.

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And we need to get as many of these things set up as possible as fast as possible

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because that's going to be the way that we really decouple, literally like it actually is the decoupling factor of people to like the number of things we can intake.

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To add to that, our target is by mid next week, we need to automate the entire intake through voice agents.

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Yeah.

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The target we have and regarding scaling, I've been working on maintenance voice agents until now to automate internal operations, but scaling is the most important factor right now.

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Steps out of that meeting.

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Wild.

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We are going through everything.

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Anyway, next up is a growth meeting, but I wanted to quickly touch base on what I'm seeing.

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They deployed voice agents in under a week.

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I think it was like a couple of days they deployed them live

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and they're running them across different industries that they're actually doing calls on and intakes on.

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Two days, three days to implement that across multiple industries

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and you know label it as R&D which makes a lot of sense

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because they're still figuring out how this thing works and

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if it actually works properly which clearly it does straight away

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and so they figure that out in a week

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and then the next week they're doubling down

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and they're going to roll this out over all industries

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and to move that quickly like that is a complete evolution of the company

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because suddenly you're freeing up the sales team

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like a ridiculous amount it's just crazy the speed is just

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incomprehensible until you're in it until you are here anyway we're

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going back in for another meeting my hands like shaking on c4

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so we paid 246 for this lead there is no application but it got instant quoted on what portal

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somebody open so you all gonna have to care about

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that you want to open up a big brother So this got instant quoted.

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Jessica for 2K?

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It was for 2K.

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So Jessica presented a $2,000 quote to somebody, and then what happened?

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She read it within an hour.

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Okay.

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Of the last phone call.

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And then what time was the last phone call?

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Be careful, Karen, with your 27T000000Z because you can't really see what the time is.

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I can't really, it's not really time set.

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Oh, okay.

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I think it was 8.15.

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8.50, 9.28.

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8.30, and now it's 9.47 and nothing happened.

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So how are we tracking that in the system?

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Jessica was told that within one hour, somebody would pay her, right?

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We have this in our system as we have no application, application bill, we gave an instant quote for $2,000.

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The person said she's gonna pay an hour.

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So I'm also a little bit nervous

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because you all don't really have control of what's happening

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if you all think the prices are $2,000 and Harsh is finding that it's $600 and you are running the sales team.

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All day long, every hour and a half, we're just gonna keep doing this.

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I'm gonna go through everything you want.

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I'm telling you, until you all get systems that answer all these questions I'm telling you, you will never have a stop to your leak of your funnel.

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You're always going to have a leaky funnel.

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We're always going to be sad at the end of the

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day talking about how we fail to keep up with what's going on.

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It'll never be good because until you get this right and you think like this, it's not going to happen.

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Next one.

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Is this a normal morning for you?

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Yes.

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This is a business that's always going.

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It's fine.

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There's a lot going on.

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I like it.

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So how are you feeling?

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Now after these two minis you've just run in, it's all systems go.

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How do you feel?

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I feel optimistic.

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I mean, I think when people know, I feel good.

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Like, it's like when you know a problem, you can fix it.

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I think it's clear what the problems are.

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I've made a clear system of delegation, like, you own this, you own this.

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It took me a while to learn that.

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I think I used to, I'm a person who is obsessive about controlling everything myself.

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So another version of where this was two months ago, I probably would have taken all those outcomes and just gone and done all of it myself.

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Then I'm super bottlenecked.

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I can't think about growth.

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I can't talk to Joanne about partnerships.

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I can't do anything.

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So I feel happy and excited and optimistic because I feel like we have dissected the problems, now people have them, but I never let it go.

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Like I'm like, okay, I said all this stuff, but I always have this subconscious thought, something can still get fucked up.

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So I'm always thinking like, okay, like now let me go monitor, let me do some other things, but like in an hour, I need to be on top of it again to make sure it's going.

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Then when I see after two or three checks that it's still going, I'll be like, okay, this is gonna end up in a good end of day.

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I can really shift my focus to board prep.

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Because right now I have to prepare for my poor meeting home and stay And I have my memo, but I've not sent it out and I have to get it out today.

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Yeah.

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Wild.

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Wild.

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I am very impressed with the level of hyper focus from Dakota.

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He promised to us at the beginning of the day

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that the one goal was focusing on fixing the leaky funnel

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but just the determination to stick to that one problem

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and try and fix it because you have to have

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that level of focus at a company of this size

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because things will always get pulled apart and put by the wayside and forgotten and like tickets get missed.

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If I wanted to get commercial insurance from these guys,

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knowing that one of the founders is sitting there going through individual quotes and individual customers is so important.

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And it's cool to see that these guys have not lost sight of the reason they exist, which is the customer.

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Also, they move at a million miles a second, like to the point of where like, I'm trying to keep up with what's being said.

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What happened?

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I need my charger.

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I was just speaking to the camera about how fast this company moves.

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And then I just get this.

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Can I come home running?

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Yeah, yeah, yeah.

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It's actually so fun here.

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I love it, man.

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Are you new or are you...

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You've been here a while?

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I've been here for like three months now.

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Hell yeah.

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Yeah.

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Super fun.

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You keep running, you keep running.

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Dude, so run me through.

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It's all hands today.

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Like it's happening.

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It's always all hands.

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Okay.

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I do think that we are going through a phase where, you know, we've been very founder mode, right?

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Yeah.

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And so because we've been very founder mode, we're like, okay, like, you know, we're very hands on deck and do every single thing.

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And of course, the company has evolved and we have had a lot of people come in to, you know, lead different efforts.

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One of the things about me and Dakota is we're very detail-oriented.

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Yeah.

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So we really care about, you know, Dakota is really detail-oriented when it comes to go-to-market, life cycle of the customer service, basically everything.

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Yeah.

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He's one of those unique people who holds a lot of context in his head.

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And then I have to think about, okay, how do I tango?

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It's all a tango.

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Because in the sense, okay, what is going on right now?

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And how do I best support the organization in the sense of building out capabilities?

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They can provide leverage.

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So if somebody goes left, I'd go right.

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So whenever there's an organizational shift that's happening, it's very much like, okay, how do I bring my organization behind it?

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And how do we have a lot of impact and force behind it?

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I see some things here where it's like Anas was testing the voice AI

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and the person just dropped off the voice AI.

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For me, the way I think about this is the highest level.

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There are 38 things that are still sitting there

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that we paid for in some way or another that we still need to figure out what's going on.

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And all I really, it's like the same kind of probe to you all every day.

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I'm trying to understand is like give me the narrative of

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how we're gonna recover all these 38 things like I'm getting closer

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but kind of like not still getting a clear sense of what exactly is happening with these things

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and that kind of concerns me.

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So I'm just trying to figure out what's actually going on.

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Can I just be sure?

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What?

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Can we just do you to make sure that this is probably...

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Please.

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And also please if I'm being unfair I promise you please tell me I'm being unfair and please help me understand.

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I'm genuinely just trying to understand

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because we get to the end of the day every day

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we have some amount of pending applications all I'm trying to

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do is make sure y'all know what's actually going on

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and I can have some hope

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that we have a path to recovery of some of this

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stuff that's all I'm trying to do okay anything else kudos

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to Garrett I think Garrett was a pretty good day we have a lot of work to do

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so I will start my night shift but it was a great day

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and I look I look forward to seeing you guys tomorrow.

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What would you say to these founders out there that, I want to do this, I want to do this,

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and properly go and change the world?

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I think the simple advice I tell myself every morning is, get into the arena and fight like hell.

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There were so many moments in me and Dakota's journey that we could have stepped away from the arena.

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You may not know if your product is making it.

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You may not know who your customers are.

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You may be trying to figure out who your co-founder is.

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Me and Dakota religiously have done 18 to 19 hour days for the last many years.

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Crazy.

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Just, like, it does, you know, there's no stopping.

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I do this every day because, like, I saw directly when the little guy gets hurt.

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Like, what happens when this doesn't go right, when it's not the happy path?

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And I genuinely do believe that this is a business that's AI for good.

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I don't think there's any substitute for hard work.

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I say, like, okay, I'm going to my night shift.

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It's like, my night shift is I'm observing all the things that happen throughout my day.

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I see a team that's in need of direction and some more guidance.

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I think they'll get there.

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I need to help them get there.

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Let me spend my evening across a number of things from product to what you experienced in the growth meeting.

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Let me make sure I come back in this evening that they see at two or three o'clock in the morning, that final message from me.

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It's like, Hey, here's how we're operating tomorrow.

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So we can achieve what we need to achieve.

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And then people see the success and the wins and they get excited and they keep moving.

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And then eventually they learn these pieces and you just compound and compound and compound.

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Yeah.

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Yeah.

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And everyone wins.

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Yeah.

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To be honest, people want to be on a winning team.

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My job is not to be anybody's best friend here.

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My job is to make sure That's it.

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I love it man.

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Well I'll get everything I need.

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This is perfect.

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Perfect.

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Thank you for joining us.

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You're always welcome.

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Thank you.

406

Legends

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실제 시나리오: AI 스타트업의 하루

이 비디오는 실리콘밸리에 위치한 AI 기반 보험 스타트업 하퍼의 하루를 담고 있습니다. 창업자와 직원들이 빠른 성장을 위해 고군분투하는 모습을 보여주며, "병목현상이 되고 싶지 않다" "퍼널을 통제해야 한다"와 같은 비즈니스 현장에서 자주 쓰이는 표현들이 등장합니다. 이런 진짜 회화를 통해 영어 회화 연습을 하면, 실제 비즈니스 상황에서도 자신감 있게 말할 수 있게 됩니다.

유용한 구문과 콜로케이션

"become the bottleneck": 병목현상이 되다. 예: "I don't want to become the bottleneck of the team." (나는 팀의 병목이 되고 싶지 않아.)
"take control of the funnel": 퍼널을 통제하다. 마케팅이나 비즈니스에서 자주 쓰이는 표현으로, 고객 유입 과정을 관리한다는 뜻입니다.
"venture scale": 벤처 수준으로 성장하다. 스타트업이 큰 규모로 성장하는 것을 의미합니다. 예: "They need to build the backend to venture scale." (그들은 벤처 수준으로 성장하기 위해 백엔드를 구축해야 해.)
"demand capture business": 수요 포착 사업. 모든 기업이 필요로 하는 보험처럼 수요가 항상 있는 사업을 말합니다.

당신의 shadow speech 챌린지

이제 영어 회화 연습을 위해 shadow speak를 해보세요! 비디오에서 "We can't ever make a billion dollars like that. That's never gonna happen."라는 구문을 찾아서, 다음 단계로 연습하세요:

원본을 2-3번 듣고 발음과 억양을 주의깊게 살펴봅니다.
원본을 멈추지 않고 바로 뒤따라 말합니다. 이때 속도와 강세를 최대한 비슷하게 맞춰봅니다.
자신이 말한 것을 녹음해서 원본과 비교해보세요. 어디가 다른지 찾고 다시 연습합니다.

이 방법은 IELTS 스피킹 준비에도 효과적이며, shadowspeaks를 통해 자연스러운 영어 발화 능력을 키울 수 있습니다. 매일 10분씩坚持하다면 빠르게 실력이 향상될 것입니다!

이 영상의 문법

화자가 가장 많이 쓰는 문형을 영상 속 실제 표현과 함께 정리했습니다.

문형	영상 속 표현
현재완료진행 have/has been + -ing — 전에 시작해 지금도 계속되는 동작	has been using · I've been working
현재완료 have/has + 과거분사 — 과거의 일이 지금도 관련이 있을 때	have evolved · have not seen · They've raised
관계절 who / which + 절 — 사람이나 사물에 대한 추가 정보	line, which is · world, which is · thing, which is
수동태 be + 과거분사 — 누가 하는지보다 무슨 일이 일어나는지에 초점	is fucked · was implemented · being done

쉐도잉이란? 영어 실력을 빠르게 키우는 과학적 방법

쉐도잉(Shadowing)은 원래 전문 통역사 훈련을 위해 개발된 언어 학습 기법으로, 다언어 학자인 Dr. Alexander Arguelles에 의해 대중화된 방법입니다. 핵심 원리는 간단하지만 매우 강력합니다: 원어민의 영어를 들으면서 1~2초의 짧은 지연으로 즉시 소리 내어 따라 말하는 것——마치 '그림자(shadow)'처럼 화자를 따라가는 것입니다. 문법 공부나 수동적인 청취와 달리, 쉐도잉은 뇌와 입 근육이 동시에 실시간으로 영어를 처리하고 재현하도록 훈련합니다. 연구에 따르면 이 방법은 발음 정확도, 억양, 리듬, 연음, 청취력, 말하기 유창성을 크게 향상시킵니다. IELTS 스피킹 준비와 자연스러운 영어 소통을 원하는 분들에게 특히 효과적입니다.

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당신의 shadow speech 챌린지

이 영상의 문법

쉐도잉이란? 영어 실력을 빠르게 키우는 과학적 방법