Shadowing Practice: 24 Hours Inside a $47M YC AI-native Insurance Startup - Learn English Speaking with Video
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kind of scares me.
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I don't want to become the bottleneck of this company that I'm constantly figuring out what everything is going on.
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That's not a good way to run a company.
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We can't ever make a billion dollars like that.
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That's never gonna happen.
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For years, the obvious way to build an AI was to sell tools to an industry.
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But the best founders have evolved past that.
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They're using AI to become the business itself and taking the revenue that used to belong to the incumbents.
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The startup I'm visiting today is doing this in one of the oldest industries there is.
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We have to be fully in control of the funnel.
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What's happening is that the funnel is in control of us.
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And there's a lot of smart people here, so we can take control of the funnel.
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Until that thing gets out to market, or until somebody bought it, it's in our hurry.
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I don't love the outcome, I'll be honest with you.
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I have to make this company exist beyond me.
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Today, I'm going behind the scenes with Harper, an AI native commercial insurance startup in Silicon Valley.
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A traditional broker takes weeks to source quotes and find a business the best price on insurance cover.
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Harper uses AI to do it in as little as a day or two across more than 160 carriers.
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Week is too long, I would say a day is a goal.
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They came through Y Combinator's winter 2025 batch
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and raised 47 million in a combined seed and series A led by Emergence Capital.
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Almost think of it as like when you boil water, at some point the water starts spilling over.
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That's us every day.
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Insurance is a demand capture business.
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Literally every business in the country needs it.
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So demand was never the problem.
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The real question lies in understanding whether they can build the back end fast enough to capture it and venture scale.
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So you may notice that it is super, super early in the morning.
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It's not nighttime.
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This is morning light right here.
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And the reason we're up so early is
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because we're going behind the scenes with a company with a work ethic that we have not seen on this channel yet.
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We're going behind the scenes with Harper, an AI native insurance startup based here in San Francisco.
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They've raised a 47 million combined seed and series A.
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And these guys are on a complete different level.
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When I was on a call with them, you know, I was gonna come in at about 8 a.m.
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That's usually when I like to come see startups.
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And they said, hey, we get in at like 5.15.
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I was like, okay, I'm gonna get in there with you.
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The hats just keep showing up in different places.
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Like, there's a hat here, there's a hat off the charge desk.
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For a bit of background context, Dakota wears hats all along, apparently.
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And just like, leaves little crickets around the office.
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Yeah.
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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.
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Did everybody see that?
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Does anybody have any questions about it?
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I have a comment.
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Yeah.
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For contractors, I feel like for all of them, we can just reach out for Inland Marine.
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Yeah.
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And just let them know, hey, if you need your tools and equipment covered, we can get that handled for you.
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And then for the higher rev accounts, we can start talking about some professional liability.
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Maybe also looking into accounts with actual employees, a specific payroll, maybe specific industries where we can look into the workers comp.
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This is the end of the month.
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So typically this should be our busiest week, right?
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A lot of people need an August 1st start date.
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So really push for that.
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Send emails, text messages, calls.
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We need to get people aware that if they want to start date for August 1st, they really should be paying today, tomorrow, Wednesday.
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Yeah, yeah, yeah, get ahead of me.
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Yeah, right.
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All right, just stepped out of that morning kind of sales briefing.
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Again, early in the morning, it's like 6.30 AM.
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The team is on it.
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Like, they are powering ahead.
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And I'm like, wow, okay, I need like two coffees.
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All right, so now I'm looking at this thing Let's see is the funnel getting leakier.
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I feel like maybe we have 14 construction contractors Nine ISC quotes one same day bound and seven applications built.
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What does this mean?
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So now I'm nervous Let's get it going
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And I heard there's some parsing issue now So
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that one was like with Vince new changes He makes the parsing like more like synchronous
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So what happens is that it's happening like at the same time
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So what I'm gonna do is I'm gonna refresh it
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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.
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So I'm gonna figure out what's going on there.
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Tell me what that means.
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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.
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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,
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this wouldn't look like this.
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It would have the specific line of coverage.
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Oh, now it says fees and taxes.
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Now it just says fees
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and taxes it's not parsing properly okay basically what's happening right now
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which is fyi is when you send out the quote they have to manually type everything in
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because whatever finn did with the parsing is fucked up
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so basically it's like it just shows fees and taxes
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so you send provide a ten thousand dollar quote it looks like you have ten thousand dollars fees
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and taxes so i think arian's on it
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but just make please like please be on top of that
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because that's really problematic for the conversion yeah
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because it just looks like all you're doing is paying fees
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and taxes to send the 8 30 products say okay cool
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and then let's make sure we have our good a good
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sense of what what our agenda for that's going to be
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so we can model what we want to see in the world, which is good agendas.
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Okay, let's think.
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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.
302
And it's cool to see that these guys have not lost sight of the reason they exist, which is the customer.
303
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.
304
What happened?
305
I need my charger.
306
I was just speaking to the camera about how fast this company moves.
307
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.
312
Are you new or are you...
313
You've been here a while?
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I've been here for like three months now.
315
Hell yeah.
316
Yeah.
317
Super fun.
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You keep running, you keep running.
319
Dude, so run me through.
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It's all hands today.
321
Like it's happening.
322
It's always all hands.
323
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?
325
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.
327
And of course, the company has evolved and we have had a lot of people come in to, you know, lead different efforts.
328
One of the things about me and Dakota is we're very detail-oriented.
329
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.
331
Yeah.
332
He's one of those unique people who holds a lot of context in his head.
333
And then I have to think about, okay, how do I tango?
334
It's all a tango.
335
Because in the sense, okay, what is going on right now?
336
And how do I best support the organization in the sense of building out capabilities?
337
They can provide leverage.
338
So if somebody goes left, I'd go right.
339
So whenever there's an organizational shift that's happening, it's very much like, okay, how do I bring my organization behind it?
340
And how do we have a lot of impact and force behind it?
341
I see some things here where it's like Anas was testing the voice AI
342
and the person just dropped off the voice AI.
343
For me, the way I think about this is the highest level.
344
There are 38 things that are still sitting there
345
that we paid for in some way or another that we still need to figure out what's going on.
346
And all I really, it's like the same kind of probe to you all every day.
347
I'm trying to understand is like give me the narrative of
348
how we're gonna recover all these 38 things like I'm getting closer
349
but kind of like not still getting a clear sense of what exactly is happening with these things
350
and that kind of concerns me.
351
So I'm just trying to figure out what's actually going on.
352
Can I just be sure?
353
What?
354
Can we just do you to make sure that this is probably...
355
Please.
356
And also please if I'm being unfair I promise you please tell me I'm being unfair and please help me understand.
357
I'm genuinely just trying to understand
358
because we get to the end of the day every day
359
we have some amount of pending applications all I'm trying to
360
do is make sure y'all know what's actually going on
361
and I can have some hope
362
that we have a path to recovery of some of this
363
stuff that's all I'm trying to do okay anything else kudos
364
to Garrett I think Garrett was a pretty good day we have a lot of work to do
365
so I will start my night shift but it was a great day
366
and I look I look forward to seeing you guys tomorrow.
367
What would you say to these founders out there that, I want to do this, I want to do this,
368
and properly go and change the world?
369
I think the simple advice I tell myself every morning is, get into the arena and fight like hell.
370
There were so many moments in me and Dakota's journey that we could have stepped away from the arena.
371
You may not know if your product is making it.
372
You may not know who your customers are.
373
You may be trying to figure out who your co-founder is.
374
Me and Dakota religiously have done 18 to 19 hour days for the last many years.
375
Crazy.
376
Just, like, it does, you know, there's no stopping.
377
I do this every day because, like, I saw directly when the little guy gets hurt.
378
Like, what happens when this doesn't go right, when it's not the happy path?
379
And I genuinely do believe that this is a business that's AI for good.
380
I don't think there's any substitute for hard work.
381
I say, like, okay, I'm going to my night shift.
382
It's like, my night shift is I'm observing all the things that happen throughout my day.
383
I see a team that's in need of direction and some more guidance.
384
I think they'll get there.
385
I need to help them get there.
386
Let me spend my evening across a number of things from product to what you experienced in the growth meeting.
387
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.
388
It's like, Hey, here's how we're operating tomorrow.
389
So we can achieve what we need to achieve.
390
And then people see the success and the wins and they get excited and they keep moving.
391
And then eventually they learn these pieces and you just compound and compound and compound.
392
Yeah.
393
Yeah.
394
And everyone wins.
395
Yeah.
396
To be honest, people want to be on a winning team.
397
My job is not to be anybody's best friend here.
398
My job is to make sure That's it.
399
I love it man.
400
Well I'll get everything I need.
401
This is perfect.
402
Perfect.
403
Thank you for joining us.
404
You're always welcome.
405
Thank you.
406
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Deze video bevat 405 zinnen en 4518 woorden om na te spreken. Het gesproken deel duurt 20:50. De spreker praat snel, ongeveer 217 woorden per minuut, dus reken op verbonden en ingeslikte klanken. 87% van de woorden hoort bij de 3.000 meest gebruikte Engelse woorden, dus de woordenschat is goed te volgen.
Belangrijke woorden in deze video
15 minder gangbare woorden uit de video, met uitspraak en betekenis:
- founder /ˈfaʊ̯n.dəː/ (zelfstandig naamwoord) — stichter, grondlegger. One who founds or establishes (a company, project, organisation, state, etc.).
- curse /kɝs/ (zelfstandig naamwoord) — vloek, verwensing. A supernatural detriment or hindrance; a bane.
- startup /ˈstɑɹtˌʌp/ (zelfstandig naamwoord) — opstart, opstarting. The act or process of starting a process or machine.
- instant /ˈɪnstənt/ (zelfstandig naamwoord) — moment, ogenblik. A very short period of time; a moment.
- compound /ˈkɑmpaʊnd/ (zelfstandig naamwoord) — verbinding. Anything made by combining several things.
- vertical /ˈvɝ.tɪ.kəl/ (bijvoeglijk naamwoord) — verticaal. Standing, pointing, or moving straight up or down; parallel to the local direction of gravity; along the direction of a plumb line; perpendicular to something…
- comparative /kəmˈpæɹətɪv/ (bijvoeglijk naamwoord) — vergelijkend. Of or relating to comparison.
- deck /ˈdɛk/ (zelfstandig naamwoord) — terras. Any raised flat surface that can be walked on: a balcony; a porch; a raised patio; a flat rooftop.
- priority /pɹaɪˈɒɹɪti/ (zelfstandig naamwoord) — voorrang, prioriteit. An item's relative importance.
- resource /ɹɪˈzɔːs/ (zelfstandig naamwoord) — bron, hulpbron. Something that one uses to achieve an objective, e.g. raw materials or personnel.
- monitor /ˈmɑ.nɪ.tɚ/ (zelfstandig naamwoord) — toezichthouder. Someone who watches over something; a person in charge of something or someone.
- agenda /əˈd͡ʒɛn.də/ (zelfstandig naamwoord) — schema, programma. A temporally organized plan for matters to be attended to.
- implement /ˈɪmpləmənt/ (werkwoord) — implementeren, (in de praktijk) toepassen. To bring about; to put into practice; to carry out.
- cheers /t͡ʃɪəz/ — proost. A common toast used when drinking in company.
- combine /kəmˈbaɪn/ (werkwoord) — combineren. To bring (two or more things or activities) together; to unite.
Phrasal verbs die je zult horen
- figure out (werkwoord) — uitvogelen, er achter komen. To come to understand; to discover or find a solution; to deduce.
- go on /ˈɡoʊˌɒn/ (werkwoord) — verder gaan. To continue in extent.
- get in (werkwoord) — binnenraken. To get into or inside something, literally or figuratively.
- double down (werkwoord) — inzet verdubbelen. To double one's wager, particularly, the name of a specific doubling bet allowed in blackjack.
Uitspraak om op te letten
De spreker gebruikt 115 samentrekkingen en verkorte vormen, zoals I'm, we're, gonna. Spreek ze kort uit, zoals je ze hoort.
- De klanken “sh” en “zh”: capture /ˈkæp.(t)ʃɚ/, partnership /ˈpɑɹtnɚʃɪp/, evolution /ˌiːvəˈluːʃ(ə)n/, shake /ˈʃeɪk/, conversion /kənˈvɝʒən/
- Lange woorden — let op de klemtoon: comparative /kəmˈpæɹətɪv/, priority /pɹaɪˈɒɹɪti/, genuinely /ˈd͡ʒɛn.ju.ɪn.li/, optimistic /ˌɒptɪˈmɪstɪk/, manually /ˈmænj(u)əliː/
Zo oefen je met deze video
- Luister de hele video één keer zonder te spreken en noteer de woorden die je niet kent.
- Begin op 0,75× snelheid, spreek zin voor zin na en ga terug naar normale snelheid zodra het makkelijk gaat.
- Neem jezelf op en vergelijk met het origineel; let daarbij op woorden als founder, curse, startup.
Grammatica in deze video
De structuren die de spreker het meest gebruikt, met de exacte woorden uit de video:
| Structuur | In de video |
|---|---|
| Present perfect continuous have/has been + -ing — iets dat eerder begon en nog bezig is | has been using · I've been working |
| Present perfect have/has + voltooid deelwoord — iets uit het verleden dat nu nog telt | have evolved · have not seen · They've raised |
| Betrekkelijke bijzinnen who / which + zin — extra informatie over een persoon of ding | line, which is · world, which is · thing, which is |
| Lijdende vorm be + voltooid deelwoord — het gaat om wat er gebeurt, niet om wie het doet | is fucked · was implemented · being done |
Wat is de Shadowing-techniek?
Shadowing is een wetenschappelijk onderbouwde taalleermethode die oorspronkelijk is ontwikkeld voor professionele tolkentraining en gepopulariseerd door polyglot Dr. Alexander Arguelles. De methode is eenvoudig maar krachtig: je luistert naar native Engelse audio en herhaalt het onmiddellijk hardop — als een schaduw die de spreker volgt met slechts 1–2 seconden vertraging. In tegenstelling tot passief luisteren of grammaticadrills, dwingt shadowing je hersenen en mondspieren om echte spraakpatronen tegelijkertijd te verwerken en te reproduceren. Onderzoek toont aan dat het de uitspraaknauwkeurigheid, intonatie, ritme, verbonden spraak, luisterbegrip en spreekvaardigheid aanzienlijk verbetert — waardoor het een van de meest effectieve methoden is voor IELTS Speaking-voorbereiding en echte Engelse communicatie.