835 Allyson Mandelbaum: Founder & CEO of Shady Lady

0:00I am unwilling to give up, but I will start over from scratch as many times as it takes to get where I want to be.

0:09Kara Goldin:You just want to make sure you will get knocked down, but just make sure you don't get knocked out. So your only choice should be, go focus on what you can control. Hi everyone and welcome to the Kara Goldin Show. Join me each week for inspiring conversations with some of the world's greatest leaders. We'll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can't wait to get started. Let's go. This episode of the Kara Golden Show is brought to you by Quince. I've been doing a bit of a spring reset with my closet lately, really focusing on quality over quantity.

0:52Kara Goldin:Fewer pieces, but better ones. The kind you reach for every single day. And that's exactly why I keep coming back to Quince. What I love is that they use premium materials like 100 % European linen, organic cotton, and really soft denim, but without the crazy markup. Their spring pieces are lightweight, breathable, and just easy. You can throw something on and instantly feel put together. I've especially been loving their linen tops. They've become my go-to. The fabric feels elevated but still effortless. And honestly, when I saw the price, I had to double check it. It's that good. And it's not just clothing.

1:33Kara Goldin:Their accessories are incredible too. Their leather bags are made from 100 % hand-woven Italian leather and look way more expensive than they are. Quince works directly with ethical factories and cuts out the middleman. So you're truly paying for quality, not the label. Refresh your spring wardrobe with Quince. Go to quince.com slash Cara Golden for free shipping and 365 day returns. Now available in Canada too. Go to quince.com slash Cara Golden for free shipping and 365 day returns. Quince.com slash Kara Golden. Support for today's episode comes from Square, the platform behind so many of the best run businesses.

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3:53Kara Goldin:Hi everyone and welcome back to the Kara Golden Show. So have you ever stopped to think about something as simple as a hat and why it never quite fits right? Too big, too bulky, designed for everyone, but really not made for you or for many women at all. Our next guest did just that. Alison Mendelbaum is the founder and CEO of Shady Lady. And after spending more than 20 years as a reality TV producer, she noticed something that most people had just accepted, that hats weren't actually designed with women in mind. So what started as a personal frustration turned into a simple but powerful product company.

4:40Kara Goldin:So much here. So the question around the brand and rethinking a category, all of those things are what I really want to dig into. And also how she pivoted careers, not at 20 years old, but deciding, I need to just go do this. So I'm very, very excited to have Allison Mendelbaum on the show. Yes. Hi. I'm so excited to be here and such a fan of you in the podcast. So this is like a dream. Thank you for having me. This episode of the Kara Golden Show is brought to you by PipeDrive. For a lot of business owners, CRMs can feel more frustrating than helpful, bloated with extras, hard to navigate, and never as simple as they should be.

5:30Kara Goldin:That's where PipeDrive comes in. PipeDrive is a simple, powerful sales CRM designed for small and growing businesses. It brings your entire sales process into one dashboard so you can actually see what's happening, your deals, your pipeline, and what needs to happen next. What I really like is how visual it is. You can see every deal, what stage it's in, and where to focus. It keeps everything organized without overcomplicating things, which honestly is what most teams need. And because everything is in one place, it's easy to keep your team aligned, stay on top of follow-ups, and move deals forward faster.

6:11Kara Goldin:It's powerful enough to grow with your business, but simple enough that you can start using it right away. Switch to a CRM built by salespeople for salespeople and join the over 100 ,000 companies already using Pipedrive. Right now, when you use my link, you'll get a 30-day free trial, no credit card or payment needed. Just head to pipedrive.com slash Cara to get started. That's pipedrive.com slash Cara, and you can be up and running in minutes. This episode of the Cara Golden Show is brought to you by LinkedIn Hiring Pro. Hi, Kara here. For small businesses, every hire matters, but so does your time.

6:54Kara Goldin:I felt that pressure firsthand. You know, a bad hire isn't just frustrating, it's expensive in time, money, and team morale. And yet hiring the right person can feel like a full-time job on top of everything else you're already doing. Sifting through applications, trying to spot the real standouts, second-guessing decisions, it can get overwhelming fast. That's why having a way to save time without sacrificing quality isn't just nice to have, it's critical. Luckily, LinkedIn Hiring Pro is built for that reality. It's your hiring partner designed to help you hire with confidence by surfacing only the right candidates without turning hiring into another full-time job.

7:40Kara Goldin:Posting a job isn't always the hard part. It's finding, connecting with, and screening the right candidates. Hiring Pro streamlines the entire process from drafting your job to shortlisting candidates and conducting AI-powered interviews for initial screenings. Their updated conversational interface lets you describe what you need in plain language, no recruiter jargon needed. Nearly 60 % of hires find a candidate to interview within a week. With Hiring Pro, you spend less time searching and more time connecting with the right talent. Join the 2.7 million small businesses using LinkedIn to hire.

8:20Kara Goldin:Get started by posting your job for free at linkedin.com slash Kara Golden. Terms and conditions apply. Okay, so for listeners who are just discovering Shady Lady, how do you describe the brand and what truly sets it apart from the traditional hat companies that are out there? Absolutely. Well, what we're doing is focusing on women and women's hats, which is something that no other hat brand is doing. And it really started for me because it was a personal frustration, as you said. I, at the point that I started Shady Lady, had two little kids, very much needed to throw on something and run out the door on a daily basis.

9:04No time to wash my hair, No time to get my roots done. Very jealous of my husband who would just throw on a baseball cap, look good and run out the door every day. And I was like, okay, I need a hat. I've always loved hats. None of them looked good on me. They looked ridiculous. They were too big, too stiff. They like fell down my ears. I had to like either have them sticking out or tucking in. The brims were too big. I like couldn't drive with them. I couldn't see. I was just like, what is going on? I cannot find a hat that fits me well. And on top of that, so many hats had team names on them or, you know, sayings like hashtag mom life, just things that I was like, I'm never going to wear this.

9:49So it really, I started doing research. You know, I looked at all my favorite stores, started doing research and learned that all hats are really made from the universal measurements of a man's head. So they call them unisex, but they're all made from men's heads. And that right there was just my light bulb moment. I was like, it's not me. It's not my head. It's not, you know, any of these things. It's that they're not being made for women. And so I, you know, having no fashion background, no manufacturing or business background, right there was like, okay, I think I need to do something about this.

10:28This is, you know, I'm going to start just making my own. So that's really what makes us different.

10:34Kara Goldin:This episode of the Kara Golden Show is brought to you by LinkedIn Hiring Pro. Hi, Kara here. For small businesses, every hire matters, but so does your time. I felt that pressure firsthand. You know, a bad hire isn't just frustrating, it's expensive in time, money, and team morale. And yet hiring the right person can feel like a full-time job on top of everything else you're already doing. Sifting through applications, trying to spot the real standouts, second-guessing decisions, it can get overwhelming fast. That's why having a way to save time without sacrificing quality isn't just nice to have, it's critical.

11:18Kara Goldin:Luckily, LinkedIn Hiring Pro is built for that reality. It's your hiring partner designed to help you hire with confidence by surfacing only the right candidates without turning hiring into another full-time job. Posting a job isn't always the hard part. It's finding, connecting with, and screening the right candidates. Hiring Pro streamlines the entire process from drafting your job to shortlisting candidates and conducting AI-powered interviews for initial screenings. Their updated conversational interface lets you describe what you need in plain language, no recruiter jargon needed. Nearly 60 % of hires find a candidate to interview within a week.

12:01Kara Goldin:With Hiring Pro, you spend less time searching and more time connecting with the right talent. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash Kara Golden. Terms and conditions apply. This message is a paid partnership with AT &T Business. Hey everyone, Kara here. Let's get real about those early days of building a business, not the highlight reel, the actual day-to-day, the friction, trying to manage everything across time zones, across teams, across locations, and realizing how much depends on staying connected. I remember those days at Hint, a retailer call, an order, a decision, all of it.

12:47Kara Goldin:And you realize quickly, connection isn't a nice to have. It's the lifeblood of your business. As a founder, you don't want to think about your connectivity. You just need it to work every time. AT &T Business is a reliable provider for small business owners. For Small Business Month, we celebrate small businesses by helping them run better. This means reliable uptime, easy switching, and smart communications. Powered by AT &T Business. Built to work. Get AT &T Business at business.att.com. That's wild. So you mentioned this, but you didn't come from the fashion world. You were a consumer or wanted to be a consumer, I should say, but you came from the reality production side of things, very, very different.

13:42Kara Goldin:I always think that the best founders and the best kind of stories in brands come from those who are trying to solve problems. And oftentimes, more often than not, I find that people were not in the industry that they're building a company in. but can you talk a little bit about kind of that time that you were going through you had been this was your career right and and you decided to make that switch which is scary but also something that maybe listeners are thinking about but I'd love to talk or hear sort of where your head was at that time and how did you decide to make that move yes absolutely I you know Now, I have to say, so I graduated college being a television, radio and film major who even knew that that existed.

14:34You know, right away, moved to New York City, started working in, at the time, talk shows. Like my first job was the Montel Williams show out of college. It was insane. You know, and then I ended up going to MTV and worked for a long time at MTV on shows like My Super Sweet 16 and True Life and Catfish and Cribs. And in my 20s and early 30s, I had the absolute best time. It really was. You know, like it was one of those, like, I'm getting paid to do this. This is my job. You know, I was flying all over the place, traveling constantly. I loved it. At the point that I got married and, you know, wanted to start a family, it hit me that this career and what I'm doing may not be the best for that lifestyle.

15:27There was so much travel, so many late nights. It really does take over your life. At the point that I was 30, I was married at that point. I got a network job working for AMC as the director of development. It was like my dream come true. I was one of the youngest people in this position. It was that, you know, the glory days of AMC where it was breaking bad and walking dead and all of this. I it was a dream.

15:56Kara Goldin:This episode of the Kara Golden Show is brought to you by LinkedIn Hiring Pro. Hi, Kara here. For small businesses, every hire matters, but so does your time. I felt that pressure firsthand. You know, a bad hire isn't just frustrating. It's expensive in time, money and team morale. And yet hiring the right person can feel like a full-time job on top of everything else you're already doing. Sifting through applications, trying to spot the real standouts, second-guessing decisions, it can get overwhelming fast. That's why having a way to save time without sacrificing quality isn't just nice to have, it's critical.

16:40Kara Goldin:Luckily, LinkedIn Hiring Pro is built for that reality. It's your hiring partner designed to help you hire with confidence by surfacing only the right candidates without turning hiring into another full-time job. Posting a job isn't always the hard part. It's finding, connecting with, and screening the right candidates. Hiring Pro streamlines the entire process from drafting your job to shortlisting candidates and conducting AI-powered interviews for initial screenings. Their updated conversational interface lets you describe what you need in plain language, no recruiter jargon needed. Nearly 60 % of hires find a candidate to interview within a week.

17:23Kara Goldin:With Hiring Pro, you spend less time searching and more time connecting with the right talent. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash Kara Golden. Terms and conditions apply. This message is a paid partnership with AT &T Business. Hey everyone, Kira here. Let's get real about those early days of building a business. Not the highlight reel, the actual day-to-day. The friction, trying to manage everything across time zones, across teams, across locations, and realizing how much depends on staying connected. I remember those days at Hint, a retailer call, an order, a decision.

18:09Kara Goldin:all of it, and you realize quickly, connection isn't a nice to have. It's the lifeblood of your business. As a founder, you don't want to think about your connectivity. You just need it to work every time. AT &T Business is a reliable provider for small business owners. For Small Business Month, we celebrate small businesses by helping them run better. This means reliable uptime, easy switching, and smart communications. Powered by AT &T Business. Built to work. Get AT &T Business at business.att.com. Of course, I also, at that point, started my family, got pregnant with my son, and had him and very quickly realized that those two things were not going to work.

19:00You know, I was living in New York City at the time. I had a nanny. I thought, okay, you know, I'm going to be one of those working city moms. You know, I'm going to have my nanny. I'll do my job. I was traveling to LA constantly. I started having crazy panic attacks and anxiety. And like, I just was so torn because I felt like I was never, never seeing my son. But I loved this job and had worked my whole career for this job. but how but I'm not being the mom that I want to be and I was just a mess I was a mess so like even if I wanted to have that lifestyle my body physically was like this isn't this isn't going to work for us like we're not going to do this so I went in and I quit my job and it was the scariest thing in the world because I didn't know what I was going to do or you know we're very much a two-income household.

19:54We ended up having to move out of the city. But I just knew that I couldn't keep doing what I was doing. So once we moved to the suburbs, I really, it was very important to me to be in control of my time and my schedule. And I love working. I'm a workaholic. I've always worked. So I knew that I would do something. But how do I kind of do that on my terms, you know, so I'm able to spend time as a mom and still be building something that I'm really passionate about. And so my first business was not Shady Lady. I first did an art business. I was taking, you know, local artists and hanging their artwork in coffee shops and restaurants and things like that.

20:38I quickly realized that it was not really scalable in the way that I wanted it to be. But it did show me that I loved owning my own business. You know, I loved being in charge of it. I loved making the decisions. I loved making the relationships with the coffee shops and the restaurants and all of this. So at the time that I, you know, knew that that business kind of wasn't it for me. But at that point, I was in the mindset of, I really, I want to start my own business and like make it a huge big business and, you know, really do something, do something great. So, and that's, you know, once you kind of get in that mindset and you're looking for these things, then when you do come up with a problem, like me not finding a hat that worked for me, it was easy, you know, for me all of a sudden to be like, okay, I'm going to do this.

21:29I don't know how to do this. I have no idea, but I'm going to figure it out and I'm going to do this. And at that point, yeah, I was 40 years old when I started Shady Lady. So, you know, not the easiest time, but I really, and I stress this whenever I talk to women and women thinking about a career change and it is never too late. You know, you hear the stories of the 20-something-year-olds that are so successful and right out of college. To me, that's great, but I couldn't have done this at 20. Like what I'm doing now, you know, in my 40s, I could have never done in my 20s. So I am just all for career changes, starting something whenever, you know, you feel like it's the right time for you.

22:18Kara Goldin:This episode of The Kara Golden Show is brought to you by LinkedIn Hiring Pro. Hi, Kara here. For small businesses, every hire matters, but so does your time. I felt that pressure firsthand. You know, a bad hire isn't just frustrating, it's expensive in time, money, and team morale. And yet hiring the right person can feel like a full-time job on top of everything else you're already doing. Sifting through applications, trying to spot the real standouts, second-guessing decisions, it can get overwhelming fast. That's why having a way to save time without sacrificing quality isn't just nice to have, it's critical.

23:02Kara Goldin:Luckily, LinkedIn Hiring Pro is built for that reality. It's your hiring partner designed to help you hire with confidence by surfacing only the right candidates without turning hiring into another full-time job. Posting a job isn't always the hard part. It's finding, connecting with, and screening the right candidates. Hiring Pro streamlines the entire process from drafting your job to shortlisting candidates and conducting AI-powered interviews for initial screenings. Their updated conversational interface lets you describe what you need in plain language, no recruiter jargon needed. Nearly 60 % of hires find a candidate to interview within a week.

23:45Kara Goldin:With Hiring Pro, you spend less time searching and more time connecting with the right talent. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash Kara Golden. Terms and conditions apply. This message is a paid partnership with AT &T Business. Hey everyone, Kara here. Let's get real about those early days of building a business, not the highlight reel, the actual day-to-day, the friction, trying to manage everything across time zones, across teams, across locations, and realizing how much depends on staying connected. I remember those days at Hint, a retailer call, an order, a decision, all of it.

24:31Kara Goldin:And you realize quickly, connection isn't a nice to have. It's the lifeblood of your business. As a founder, You don't want to think about your connectivity. You just need it to work every time. AT &T Business is a reliable provider for small business owners. For Small Business Month, we celebrate small businesses by helping them run better. This means reliable uptime, easy switching, and smart communications. Powered by AT &T Business. Built to work. Get AT &T Business at business.att.com. Yeah, definitely. I love that. You're such a great example of that. So, I mean, I meet people who think about starting a company all the time and they're like, I don't know, like the first thing about it.

25:23Kara Goldin:And they always put all these excuses in front of themselves. So I think it's, you know, you just went and did it. But what was the first step that you made when you decided I'm going to go do Shady Lady? What was the first thing you did? You saw this problem, but like how, I mean, in order to actually start a company, you have to have a few steps that you make in order to feel like, okay, I'm going to go and try. Yes. Yes. I could tell you Google was my best friend. I Google, I Googled everything. I Googled, you know, how to set up an LLC, how to, you know, get a trademark, how to, I Googled.

26:05And it's honestly, it's never been easier to start a business, harder in some ways because it is such a crowded marketplace, but everything is really available online to help you get started. So I did, I started doing some of that from the back end of it. And I just started sketching like what I would want in a hat. So different designs. I knew in my head what I was looking for. So I was just started sketching the hats that I wanted in my closet. And then I started, on top of that, sketching those designs, knew that I couldn't make these myself. So trying to find a manufacturer, which really for that, I started talking to everybody that I knew.

26:55People that had nothing to do with manufacturing or fashion or hats or this. I was just like, this is what I'm doing. Do you know of anybody or anybody who knows anybody that may have a connection to a manufacturer? Because I knew that I didn't want to find online. I really wanted some sort of personal recommendation or connection. Because if I was bootstrapping this and putting, you know, my own money behind it and really setting it up, I needed that connection to be something, you know, that was recommended to me. And that's what happened. I talked to a friend, an old producer friend who I had worked with, and we were just chatting on the phone.

27:39And I told her what I was doing and that, you know, I was looking for a manufacturer. And she said, oh, my friend, I think, is dating somebody who is a manufacturer. And that was literally how I found a manufacturer. and I've been with him to this day. He's fantastic, who has kind of, you know, helped me. Our businesses have built together, you know, because he was kind of just starting out too. So we have been growing together and it's just a great relationship. But I don't know that that would have happened for me just cold calling people. So that was important to me.

28:09Kara Goldin:That's so, so interesting. So how did you come up with the name Shady Lady? So that was tough. I took, you know, some market research of my own, of my college friends. My college friends, my group of, you know, they were my sorority sisters. We talk constantly and email each other constantly. And they are some of the funniest women that I know. So I told them what I was doing, told them that I needed a name. And they really helped me. You know, we started with Shade, Shady. We were literally just, we got on a Zoom and we workshopped it. and they helped me come up with it. And I, as soon as I heard it, I was like, that's it.