Matt Lipstein lives in Austin, Texas. He hosts a weekly radio show on KOOP-FM called Free Samples and he makes ambient music under the name, The Moss End.

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TRANSCRIPT:

ZAK: 10 years ago, Matt was living in Brooklyn. It was a cold, January morning after a snowstorm.

MATT: And I was heading out to our car which was parked on the street as you do and when I went up to the car, I noticed something was amiss and I went to turn the car on and all the lights came up on the dashboard when I did that. Like I've never seen that before. And, uh, I went outside and I brushed some of the snow off the side of the car and I realized that my car had been hit by something and then as I look up and down the rest of cars that were parked on that side of the street, all the cars were hit by something and I thought that because it was a snowstorm, it was likely a snowplow that had come and just nailed an entire side of the street just kind of scratching up all the sides of the cars and knocking off side-view mirrors and all that.

ZAK: It's a great way to start your day.

MATT: It was a rough one.

ZAK: So Matt calls his insurance company and they tell him, they'll pay for the damage but not the one-thousand dollar deductible.

MATT: And I felt this since a city of New York snowplow had hit my car and so many others that it was worth calling the city of New York to find out if they would pay for my thousand dollar deductible and what unfolded was a year and a half process of trying to get the right person on the phone to understand what happened and why it seemed reasonable to ask the city of New York to pay for that thousand dollar deductible.

ZAK: How many phone calls do you think you made over the course of that year and a half.

MATT: I would have to guess I made at least 20-25 phone calls.

ZAK: And your final call, who was that to and what were they able to do for you?

MATT: So, I somehow made my way to...I believe the person's title is comptroller. In about 2-minutes, he was like, yeah, of course we should pay that. And then just in an instant the skies opened and he made it happen and within a few weeks after that I got a check for a thousand dollars from the city of New York.

ZAK: Wow. Ok, so...the advice that comes out of this crazy 18-month journey is what?

MATT: Always get the right person on the phone. Make sure that they understand your problem or your request and then try to gauge if they have the knowledge or the access to help you. And if they don't, you can go one of two ways...you can either politely disconnect from that call and try again or you can ask to escalate to get to the right person. But either way, use your sense and see if that person is the right person on the phone and usually you know whether they are or are not.

ZAK: Right. And I feel like to actually do this takes a combination of skills, patience, resilience, persistence...You have to be willing to say to someone like, 'you are not helping me' which I think for some people can be challenging cause you don't want to, if you're a people pleaser like me, you don't want to hurt their feelings. It seems to me that you need to either be that type of person or practice to get this right.

MATT: I think practice sounds right. I mean, something that i've said to people a lot on the phone is, 'don't take this personally. I know that you're trying to help me but I'm not getting the results that I need. Can I speak with your manager or supervisor." Or, I'm going to disconnect and see if I can get someone else on the phone.

ZAK: Now that is some hard-won wisdom. Matt got in touch with me through the advice hotline. I would love for you to do the same thing. If you have some advice, give me a call at 844-935-BEST. And if you're enjoying this show, please consider leaving a rating or review on Apple Podcasts. Thanks so much in advance for doing that. I'll talk to you soon.

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