Shreya Chowdhary, Founder and CEO of Oak and Hill, on Stress Crying and Trusting Your Instincts

Updated: Sep 2, 2020

So let’s just start off with what you’re doing at Oak and Hill and what your goals are with it. 


“So, basically, Oak and Hill is a tailgate clothing company. I’m doing a lot of vintage now I’m going into NFL and MBA stuff too. Vintage is just a huge thing right now and it feels good to buy stuff that you can reuse but that’s also cool. I noticed that a lot of tailgate clothing companies make the same things and I like for my stuff to be different. I like finding cool stuff from stores and changing them into tailgate things rather than taking a plain crew neck and printing stuff on it. So, that’s what I do. Eventually, I want to turn Oak and Hill into an actual clothing company and get clothing made for going out and normal stuff. So right now I’m making the money to do that and it’s also kind of on hold right now with the whole corona thing.” 


Have you hit a lot of road blocks because of Coronavirus?


“Yeah, so a lot of my shipments have been delayed and I have all these places where I order things in bulk but their factories were shut down and a lot of my shipments from China were delayed and the mass amount of orders at this time has caused more delays for my orders. Trying to deal with everything mentally that’s going on right now is really hard. My intern is also at home in New York which has been hard but Oak and Hill is not being hit as hard as some other businesses so I’m thankful for that.”


How did you get started with Oak and Hill? Did you expect it to be what it is today or did you think it would be more like you making things for just your friends?


“Yeah, so honestly I wear sweatpants and sweatshirts every single day, but when I do go out or tailgate I get a lot of compliments on my clothing because when I try I actually have good style. I wore these sweatpants this past summer and I got so many compliments on them. I realized, though, that even though they were an expensive pair of sweatpants, I could just make them myself. I even had one person say, “I want those for [the] OSU [tailgate].” So that was in my head but then when I was getting on the plane to go back to Michigan, I got the call that I didn’t get a return offer for my job so I was just very mad. So when I get on the plane I really wanted to do something to prove myself and I was just thinking and I decided I would start a tailgate company. So by the time I landed in Detroit, I went online and started ordering stuff on Amazon. I did it so quickly and I was really just trying random shit for the first month and I missed the senior bar crawl and I would come home from tailgates crying because nothing was working and everyone kept telling me to focus on recruiting. So then four weeks after I got to Ann Arbor I released the website and I sent it in the sorority GroupMe and I told everyone that it was for a class just because I was nervous. And yeah, the first day I only got 8 orders and so I didn’t go out that night and I just cried. But then, I don’t know, once I made an Instagram for it, it kinda just blew up.”


So what do you think contributed to the success? It’s obviously grown a lot in the past couple months so what do you think was the leading cause for that?


“I think a lot of it was social media and Instagram, for sure. Marketing is something I put a lot of time and effort into. I think that most tailgate companies or just clothing companies in general, their instagrams are just pictures of the item in good lighting and looking pretty or just pictures of pretty girls wearing these items. For me, I feel like if you were spending money on an item, I want you to be able to see it on. So I would take videos of myself wearing these things or my friends wearing them. My prices are also very reasonable compared to other companies. Like puffer jackets are 55$ with free shipping or a customizable sweatshirt is $30 with free shipping a lot of the time. So, I understand that prices don’t need to be that high and I kind of just employed a different marketing strategy. I also do a lot of giveaways and raise a lot of money for organizations because it’s so important to me. Like in terms of profit, I was negative until February, but even in October I was still doing giveaways and raising money for Mott Children’s Hospital. So even though I wasn’t doing it for publicity, these giveaways get a lot of publicity and show that Oak and Hill have more than just clothing and it cares about people and charity.”


What would you say your most distilled piece of advice might be for someone who might want to start a business during college or in general? 


“Well there’s two things really. One: you need to be prepared to give up your life. If you’re going to be putting something into this, you need to make sure you have the funds and you need to make sure you have the time. I didn't go out nearly as much as I did before, I was stressed, didn’t take care of myself and I was getting sick all the time and you need to be able to handle that. You need to be able to handle running a company when you have the flu or strep or pinkeye in both eyes. You really need to handle that and finals and everything. You’re going to need to give up things to run this company or whatever you’re trying to do. 


And second: you need to believe in yourself and not care about what anyone else thinks. Like, even my family - my mom and dad - still don’t support it and didn’t support it from the start. I’ve been funding it since the beginning on my own. My guy friends would come over and say like, “you’re not actually going to go through with this,” or my closest friends would tell me to focus on school. You can’t let those things get to you because it’s better to start something and fail than wish you started it. I was really nervous about what people would think at first, too, but now I feel so confident about starting literally anything. I feel so confident that I could start anything even if it fails just because I did this one thing and it worked.”


So I know you said you weren’t taking care of yourself or that you weren’t focusing on school work. How did you kind of find that balance in the middle?


“Well, I didn’t. I really didn’t sleep at all like when I say that I mean I was going to bed at 4 or 5 am every day. So I gave up sleep. Social stuff, I literally would go out and like my tailgates were all marketing. I would always just take videos and pictures for it. It wasn’t about having fun. I didn’t really have fun this year, to be honest. When you’re starting something that means a lot to you, it becomes your whole focus. So, that was hard. And school, I failed one class and almost didn't graduate the first semester. I had C’s and D’s but I got a job in October so I didn’t care that much, but it was a class for my major so I had to petition that for a long time in order to graduate. And then in the second semester, I almost didn’t graduate again. So I don’t really have advice on that but… yeah.”


Do you regret having started it during college? Like do you wish that you had your last tailgates or your bar crawl or are you just happy with how it all turned out? 


“It’s so hard because I was prepared to go back to Michigan after spring break and go crazy. Like I shut down my website and I was going to start enjoying things so coming back from spring break was really hard because everyone started leaving. But no, I mean, absolutely not. It set me up for my confidence in the world. People are scared of losing their jobs right now and obviously I don’t want to lose my job but I feel so fine if that happens because I can support myself with this. Also, I think if anyone wants to start a company they should start it during college. You’re not going to have time when you’re out of school because you’re going to have to either choose your job or this and college is just such a good customer base because you’re a college student too so you know what they want.”


So, something else I’m wondering about, and something I’m thinking about with my own blog because I’m trying to make all sorts of stuff is your discovery process. How did you learn how to make these things? 


“Honestly, I really didn’t have a process. Initially my clothing was the Avery labels, basically you print it on a printer and then you ironed it on. So then when I started doing that, I wanted to make things with better quality so I found a machine and that one was great but you can only really do one color. Now I’m starting to look for places that do screen printing but I have to be careful with that. It’s really about trial and error. Once you get more money, you can get better quality machines. I had a sewing machine and now I’m upgrading to an embroidery machine that’s around 4 times the cost of that. There was really a lot of crying, a lot of crying… so much crying. You just have to keep working at it. I learned how to use a sewing machine and I still don’t really know how to properly use it.”


Other than looking for places that use different techniques, what else are you working on right now? 


“So, I want to get the puffer jackets with color blocking on the sleeves, that would be so cool. And the vintage sweatshirts that I have - people are in love with those and I’m in love with them too and I want to keep them all - but I want to figure out how to make the actual sweatshirt with the colors. I found a place to get white Gildan joggers which is insane because they’re literally sold out everywhere but I have some of those coming and I’m praying that they’ll get here in mid June but they’re sold out because everyone’s fucking doing DIY projects. People comment on Oak and Hill all the time asking where they can find white joggers. That’s a problem with Oak and Hill and with starting a company, though, people just ask you the craziest shit. Finding that place was really exciting though, I did so much research like three hours a day for a week or two before I found it.”


Other than these weird DMs that you get, what’s the most bizarre or negative aspect of Oak and Hill?


“Well for one, a lot of people will tell you how to run your company. Michelle Obama said it best. Everyone is always telling Obama what to do and saying that you need to do this or not do this. Everyone thinks they're smarter than you when they’re not in that situation and half the things that people say are things I’ve already tried that didn’t work. So I’ve started to just say like okay thank you and move on. People are just always telling me what I need to do, and I get it because it usually comes from a good place but it’s just a lot. And sometimes, I have to sell to people I don’t like, like people from high school who I think are genuinely horrible people, so it’s hard having to talk to them and have them wear my stuff. A lot of people ask me all the time to borrow stuff, too. Even when I was in debt and everything - and people knew that because it was on my private story - they would say things like, “do you have anything I don’t have to pay you for?” And I was just thinking like I’m $5,000 in debt and just like, who raised you? Like why would I give you anything? 


I think I’ve had around 10 rude customers and I’m usually pretty chill about it. I’ve had some ask me for refunds because they switched schools which was weird but I said yes to most of them. I’ve had a lot of crazy moms, though. There was only one really bad incident and this girl was literally such a bitch that I said I would fundraise to pay for her therapy. I was so mad at how she treated me and I just refunded her so it could be over with. I really lost my cool.”




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