Практика Shadowing: 24 Hours Inside a $47M YC AI-native Insurance Startup - Изучайте разговорный английский по видео

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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?

100

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,

101

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

102

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

103

and how fast versus the first pass rate.

104

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?

105

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?

106

Yeah.

107

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.

108

Yeah, I agree.

109

We should take this part of the conversation

110

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

111

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

112

I really want to explore this little more

113

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

114

Okay, cool.

115

So we got that all done.

116

Do you have breakfast?

117

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

118

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

119

Yeah, it's weird.

120

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

121

So are you saying like espresso coffee or brew coffee?

122

What's the vibe?

123

You know what?

124

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

125

C4.

126

I know, it's dangerous, scandalous.

127

I was just with Dakota in the meeting.

128

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

129

And he says, Cursor Cursor Cursor.

130

What is that?

131

Oh, okay.

132

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

133

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

134

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.

135

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.

136

Oh, cool.

137

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

138

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

139

So a couple of things.

140

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

141

So we have both engineering operations.

142

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

143

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

144

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

145

And by doing so, they can move faster.

146

Right because they already know their pain points very well.

147

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

148

Dude.

149

All right real quick Let's try this.

150

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

151

Cheers Holy shit, that's really good.

152

It is really dangerous.

153

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

154

How do you like it?

155

That's a good move.

156

It's crack.

157

It's crazy.

158

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

159

If you start beating ants on your skin.

160

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

161

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

162

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

163

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

164

Correct.

165

Over the weekend, we actually added three more verticals.

166

Also, each vertical is down.

167

Where are they?

168

We added retail, smoke shops, and consultants.

169

Okay.

170

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

171

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

172

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

173

I've tested them all night yesterday.

174

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

175

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

176

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

177

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.

178

We need a massive signal.

179

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

180

50 calls going at one time.

181

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

182

And literally just make sure you asterisk it.

183

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

184

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

185

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

186

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

187

So that's a top priority.

188

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

189

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

190

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

191

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

192

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

193

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,

194

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

195

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

196

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

197

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

198

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

199

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,

200

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

201

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

202

It's literally able to do all the calls.

203

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

204

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

205

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

206

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

207

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

208

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

209

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.

210

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

211

Yeah.

212

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.

213

Steps out of that meeting.

214

Wild.

215

We are going through everything.

216

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

217

They deployed voice agents in under a week.

218

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

219

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

220

Two days, three days to implement that across multiple industries

221

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

222

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

223

if it actually works properly which clearly it does straight away

224

and so they figure that out in a week

225

and then the next week they're doubling down

226

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

227

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

228

because suddenly you're freeing up the sales team

229

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

230

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

231

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

232

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

233

somebody open so you all gonna have to care about

234

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

235

Jessica for 2K?

236

It was for 2K.

237

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

238

She read it within an hour.

239

Okay.

240

Of the last phone call.

241

And then what time was the last phone call?

242

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

243

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

244

Oh, okay.

245

I think it was 8.15.

246

8.50, 9.28.

247

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

248

So how are we tracking that in the system?

249

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

250

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

251

The person said she's gonna pay an hour.

252

So I'm also a little bit nervous

253

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

254

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

255

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

256

I'm gonna go through everything you want.

257

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.

258

You're always going to have a leaky funnel.

259

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

260

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

261

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

262

Next one.

263

Is this a normal morning for you?

264

Yes.

265

This is a business that's always going.

266

It's fine.

267

There's a lot going on.

268

I like it.

269

So how are you feeling?

270

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

271

How do you feel?

272

I feel optimistic.

273

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

274

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

275

I think it's clear what the problems are.

276

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

277

It took me a while to learn that.

278

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

279

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.

280

Then I'm super bottlenecked.

281

I can't think about growth.

282

I can't talk to Joanne about partnerships.

283

I can't do anything.

284

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.

285

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

286

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.

287

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.

288

I can really shift my focus to board prep.

289

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.

290

Yeah.

291

Wild.

292

Wild.

293

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

294

He promised to us at the beginning of the day

295

that the one goal was focusing on fixing the leaky funnel

296

but just the determination to stick to that one problem

297

and try and fix it because you have to have

298

that level of focus at a company of this size

299

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

300

If I wanted to get commercial insurance from these guys,

301

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.

308

Can I come home running?

309

Yeah, yeah, yeah.

310

It's actually so fun here.

311

I love it, man.

312

Are you new or are you...

313

You've been here a while?

314

I've been here for like three months now.

315

Hell yeah.

316

Yeah.

317

Super fun.

318

You keep running, you keep running.

319

Dude, so run me through.

320

It's all hands today.

321

Like it's happening.

322

It's always all hands.

323

Okay.

324

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

325

Yeah.

326

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.

330

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

Legends

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Почему практиковать речь на этом видео?

Это видео — отличная возможность для практики разговорного английского, потому что оно сочетает деловой контекст с естественной речью. Сотрудники стартапа говорят быстро, используют разговорные фразы и обсуждают актуальные темы (AI, бизнес, страхование). Это идеально подходит для shadowing (т.е. повторения за говорящим), так как вы научитесь воспринимать быструю речь и копировать интонацию. Учиться английский по видео таким образом помогает улучшить не только произношение, но и понимание контекста в деловых ситуациях.

Грамматика и выражения в контексте

"We can't ever make a billion dollars like that" — здесь используется конструкция "can't ever" для усиления отрицания. Обратите внимание на разговорную форму "like that" (таким образом), которая часто заменяет более формальные выражения.
"What's happening is that the funnel is in control of us" — структура "What's happening is that..." помогает сосредоточить внимание на событии. Это удобно для объяснений в деловых диалогах.
"I don't love the outcome, I'll be honest with you" — фраза "I'll be honest with you" добавляет честность и естественность. Она часто используется, чтобы мягко выразить критику или сомнения.

Трудные места для произношения

В видео есть несколько слов, которые могут вызвать сложности: "incumbents" (инкумбенты, существующие игроки на рынке) — обратите внимание на ударение на первом слоге и звук "b" в середине. "funnel" (воронка, модель продаж) — произносится как "фаннел", а не "фуннель". Также стоит обратить внимание на быструю речь: слова часто сливаются, например, "kind of" становится "kinda", "want to" — "wanna". Это типично для разговорного английского, и shadow speech поможет привыкнуть к таким особенностям.

Используйте это видео для shadowing английский — повторяйте за говорящими, копируя их темп и интонацию. Это один из самых эффективных способов улучшить речь на практике!

Грамматика в этом видео

Конструкции, которые говорящий использует чаще всего, с точными словами из видео:

Конструкция	В видео
Present Perfect Continuous have/has been + -ing — действие началось раньше и продолжается	has been using · I've been working
Present Perfect have/has + причастие прошедшего времени — прошлое действие, важное сейчас	have evolved · have not seen · They've raised
Придаточные определительные who / which + предложение — уточнение о человеке или предмете	line, which is · world, which is · thing, which is
Пассивный залог be + причастие прошедшего времени — важно, что происходит, а не кто это делает	is fucked · was implemented · being done

Что такое техника Shadowing?

Shadowing — это научно обоснованная техника изучения языка, изначально разработанная для подготовки профессиональных переводчиков и популяризированная полиглотом доктором Александром Аргуэльесом. Метод прост, но эффективен: вы слушаете аудио на английском от носителей языка и немедленно повторяете вслух — как тень, следующая за говорящим с задержкой в 1–2 секунды. В отличие от пассивного прослушивания или грамматических упражнений, Shadowing заставляет мозг и мышцы рта одновременно обрабатывать и воспроизводить реальные речевые паттерны. Исследования показывают, что это значительно улучшает точность произношения, интонацию, ритм, связную речь, понимание на слух и беглость речи — что делает его одним из самых эффективных методов для подготовки к IELTS Speaking и реального общения на английском.

Техника шедоуинга: читать полное пошаговое руководство →

Практика Shadowing: 24 Hours Inside a $47M YC AI-native Insurance Startup - Изучайте разговорный английский по видео

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Почему практиковать речь на этом видео?

Грамматика и выражения в контексте

Трудные места для произношения

Грамматика в этом видео

Что такое техника Shadowing?