Lindsey and Courtney Glasser of Grey Bandit: “Strategic Reinvestment ”

Strategic Reinvestment — Don’t be greedy. Take what you’re making and reinvest it into your business. If you want to get to the next level, you need to reinvest. Save where you can, take only what you need to pay bills and meet your needs, and re-invest everything else back into the business. Forego a large salary […]

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Strategic Reinvestment — Don’t be greedy. Take what you’re making and reinvest it into your business. If you want to get to the next level, you need to reinvest. Save where you can, take only what you need to pay bills and meet your needs, and re-invest everything else back into the business. Forego a large salary so that you can keep growing. We did this for the first few years of our business and truly believe it helped us grow to where we are today.

Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

I had the pleasure of interviewing Lindsey and Courtney Glasser.

Lindsey and Courtney Glasser are the co-founders of Grey Bandit, a clothing and e-commerce business that highlights confidence building, mental health and fashion. Along with their brother Robert, the triplets launched Grey Bandit in 2017 to fill a gap in the marketplace that they personally experienced. Now, Grey Bandit has grown into a multi-million dollar business providing a lifestyle of wellness and positive vibes for all their customers.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Lindsey: Growing up with parents who were both entrepreneurs, my siblings and I knew from an early age we wanted to build our own company. As kids we didn’t know what that would be, but our mom gave us a lot of insight early on. We’d go to her warehouse and help pack orders, make sales, work with graphic design, merchandise, and it really showed us the hard work it takes to start a business and all 3 of us admired this so much. In college, Courtney and I were both avid online shoppers and in 2015 we were shopping so much. At the time, we loved buying from these amazing Australian boutiques, but there was nothing here that was on-trend and easy to find that we could shop at our fingertips.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Lindsey: It wasn’t necessarily one specific moment, but Courtney and I regularly talked about how there was this gap in the US market. For my senior year project, I wrote the business plan for Grey Bandit, since we had always talked about doing something like this down the road. Courtney was going to do a mockup website for her senior project, but we knew we needed something more, another hook. I noticed that many brands had charitable initiatives and mental health was something that we and so many of our friends dealt with every day. I knew that the target demographic for Grey Bandit would relate to these issues because we did! We felt the connection, so we included this in the plan and when we launched, we knew we had to create a community to spread confidence and positive vibes, not just in what you’re wearing, but by being authentic and real. It was important to us to share real people and ourselves, our stories. We felt like the two (clothing and mental health) fit together. After graduation, the three of us talked it through and we decided we were ready to do this and we launched Grey Bandit in August 2017.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Courtney: Definitely our mom. She is a hard-working entrepreneur. She has always had so much drive and determination. She owned (and still owns) her own screen printing business. She would teach us the importance of various skills that helped her run a business. We were always in awe of the hard work and dedication she had. When we first told her we were going to start Grey Bandit, she had no reservations. She believed in us and because of that stood behind us 110%. Without her, Grey Bandit wouldn’t be where it is today. When we proved our business model to her, she gave us a small loan to help us scale. Without that, we probably wouldn’t have been as risky and wouldn’t have grown at the pace we did. Once we were successful we were able to pay back that loan, but we would not be where we are today without her.

What do you think makes your company stand out? Can you share a story?

Courtney: I think there are a few things that make our company stand out. First and foremost, we want everyone to look good and feel good when wearing Grey Bandit. We regularly talk about mental health and wellness on our social media channels and want to encourage normalizing the conversation around mental health. I think this is something a lot of our core demographic can relate to, even more so in the pandemic; it’s something we struggle with day to day. As we grow as a business, we’re taking this a step further. At the end of this month, May — Mental Health Awareness Month, we’re hosting a group therapy zoom session with a licensed professional counselor and yoga instructor. The session will highlight how Yoga can be beneficial to mental health and self love. This is just one way to engage with our community that we hope to continue in the future.

Lindsey: Another thing that I think makes us stand out is that we always put our customers first. We use social media in a big way to help us interact with our customers. We’ll ask for their opinions to make sure that every time we roll out a new product, it is something that our customers will be interested in. We include them in the process because at the end of the day their opinion matters most! In addition, I think if you can go above and beyond to help a customer out, it only strengthens that relationship and leaves the customer feeling excited to come shop with us again.

How have you used your success to bring goodness to the world?

Courtney: One of our biggest goals as a company is to help reduce the stigma around mental health and be a resource for our community. As someone who has anxiety, I want people to understand that anyone can have anxiety — whether you’re a student or a brand founder! I hope that by normalizing the conversation around mental health we’re able to bring goodness into the lives of our followers and customers.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?


  1. Take Risks — Back when we first started, we had no idea about influencer marketing but just decided to take the risk. While they may not have been the best investments in the beginning, our work helped us learn and get to where we are today. It helped us understand and form a better strategy. Beyond just our marketing, when we first launched, we had to take risks in inventory to plan for upcoming launches and seasons. To an extent this is still true, but now we’re able to forecast and predict more.
  2. Be Compassionate — Customer service is a huge priority for us. Our customers are how we got to where we are today and our compassionate personalities have helped us really understand their questions or at times frustrations. For example, we’ve had customers talk to us about a lot of reasons why they need extensions on the return policy or exchanges. Whether they have something going on at work or are struggling with something personally, we understand that things come up. We believe it is so important to treat people with compassion because you just never know what could be going on in their lives.
  3. Be Innovative — You have to be able to adapt with the times. E-commerce is very fast paced so we have to know when to switch and change up what we’re doing. We are constantly pivoting. Whether it’s through our marketing or coming up with a better way to provide customer service, we always think about how we can pivot to make our business stronger. When the pandemic first started, we had to be really innovative; we had a lot of inventory and the products people wanted were changing. We had to think on our feet and change our plan. We saw value in having comfortable clothes and the tie dye trend early on in the pandemic. We called our warehouses across the U.S. to get white sweatshirts and partnered with a tie dye creator to tie dye everything for us, to give our customers what they were looking for as quickly as possible, without sacrificing quality.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Lindsey: We’ve learned that when buying inventory, we need to think about our customers. We’ve taken the advice of wholesalers to buy into certain trends based on their trend reports, buying a certain style from them that in the end ended up being a bust. In turn, we learned that we know our customers best and we stay true to our customers. For example, our bathing suits are sold in a variety of prints and patterns — which has been very successful with our customers. While we originally stayed away from solids, we took advice to buy into the solid bathing suit market and did not sell through the inventory. Our prints are what our customers want. That is why we now buy what our customers will love and know will be successful based on our own reports.

Can you tell us a story about the hard times that you faced when you first started your journey?

Courtney: We started our business right out of college and a lot of people told us not to do this or that we couldn’t succeed. People would ask us all the time, “Are you sure that’s what you want to do?” “Do you really think you can do this?” We were constantly questioned and every day we didn’t know if we would be able to pay our bills. We quite literally shared a bed our first couple years out of college. To us, it was the sacrifice that we had to make to save money and help our business be successful.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

Courtney: We really believed (and still believe) that things take time. Rome wasn’t built in a day. Our mom who worked in retail told us you have to give it 3 years to really see the results. If you’re still in the red by then, then you have to close the doors, but it’s important to see it through. We sacrificed a lot to make it happen, but we knew our vision was something that could be a profitable business. We knew we had to evolve, grow and innovate. If we pushed through and continued what we were doing, we knew that we would grow. If you’re passionate about your business, that’s the drive that will help you continue forward.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

Lindsey: It’s so important to acknowledge the highs and celebrate the victories, but also learn from the lows. You’re allowed to be upset, but if it’s not going to matter in 5 years, don’t spend more than 5 minutes on it. If you get too stuck on the lows you won’t be able to move forward. Have patience and push through. Think about what you can change to bring more momentum and help with the lows. Not every day is going to be the best day ever, but there will be more to come if you keep working. There are days when sales are slower but that doesn’t mean it’s the end for us. It’s a matter of looking at what else we can be doing.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

Lindsey: Every company and every brand is different. It’s really important that any young founder or entrepreneur knows this. What worked for us may or may not work for someone else. I would definitely recommend they talk to their network as much as possible. Chat with people who have done both. Listen to them and ask questions! You can never ask too many questions. Growing your network is a tremendous thing to do when starting your business. You never know how someone can help you along the way. Once you’ve explored both options, look at your business model and see which would be the most effective for you.

Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.


  1. Get in the mindset of your customers — We are our own customers so with everything we do, we think about if we would purchase or become a repeat purchaser. This is something we did from day one. Even with our first buy, we sat down and thought about if we would purchase each piece and why. We think about this every season now.
  2. Be open-minded — Listen to advice from others and don’t be stubborn. It’s important to be open to change. If you’re set in your ways, you may not try something different to take your business to the next level. As we mentioned before, when we first started investing in influencer marketing, our investments were not seeing a return. We needed to adapt and change our thinking to see a strong ROI. Beyond that, we try to be open minded every day. Most recently, we spoke to some of our customers and saw that they were shopping on mobile and apps. We launched the Grey Bandit app in February. Now app purchases account for more than 10% of our sales this year and we have over 18,000 downloads! We initially weren’t sure if an app was the right move for us, but we were open-minded and listened to our customers.
  3. Have a point of differentiation — What makes you different from all the other businesses? When we were starting Grey Bandit, we knew we were going in with a mental health initiative. We wanted our social media feeds to be real and relatable, showing a normal college girl in their Grey Bandit clothes. Other brands were using stereotypical models or mannequins at the time and we needed to show our customers wearing Grey Bandit and feeling confident. In 2017, online boutiques were not thinking this way. We knew that if people could see the clothes in real life — at brunch, out to dinner, in the city, the beach etc.- then they would be able to envision themselves in it and feel confident when they did wear it. That was our point of differentiation.
  4. Strategic Reinvestment — Don’t be greedy. Take what you’re making and reinvest it into your business. If you want to get to the next level, you need to reinvest. Save where you can, take only what you need to pay bills and meet your needs, and re-invest everything else back into the business. Forego a large salary so that you can keep growing. We did this for the first few years of our business and truly believe it helped us grow to where we are today.
  5. Know your numbers — You need to know the numbers behind your business. What is your overhead? How many employees do you need? What do you need to charge and what are your margins — and believe in your pricing. Be able to stand behind what you’re putting out there. Make sure you know your return customer rate. We are constantly looking at our numbers to plan ahead. One summer we sold 50 pieces of a bathing suit in 2 days, but the season is 3 months long, so we knew we needed to put in a reorder quickly so we didn’t miss out on the momentum.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Courtney: Not being open minded. People were questioning us from the beginning when we started our business and when we first started with influencer marketing. Then later on those same people realized they needed innovative marketing like influencer marketing for their business to grow. It’s important to be open minded and take risks. In order to be successful you have to make mistakes to see what works for you and give new things a try. If you don’t you may still grow, but the rate at which your business scales will be much slower.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

Lindsey: Schedule time for yourself. As startup founders, there’s always something that comes up. If you don’t schedule time for yourself as if it’s a meeting, then you won’t take it. We know this can be challenging, it is for us too, but physical and mental health and wellness are so important to run a successful business. Sometimes it will feel like things are non stop which is why it’s important to take time for you. You can’t be successful if you’re constantly burning out because then you’re never really focusing on the tasks that need to get done. By actively scheduling time for you into your daily schedule you’ll hold yourself accountable for it.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Courtney: A huge part of our business is mental health awareness. We’ve done some campaigns surrounding mental health education, but we want to encourage more people at a younger demographic to feel comfortable talking about their mental health. If we, as brand founders can do it, we hope that consumers will feel less alone when they talk about it. You go to your general practitioner annually for a check up, we would love to start a movement to normalize going to therapy for a regular mental health check up, even if it’s just annually. In the meantime, we are doing what we can to donate to organizations that directly give people access to therapy.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Both: Selena Gomez — We love how much she talks about mental health and while also being a strong businesswoman. Selena has struggles, just like everyone else, and now talks about them openly although she could have kept quiet and just seemed like someone who has it all to outsiders.

How can our readers further follow your work online?

Readers can visit to shop or check us on our instagram or TikTok to see more about what we offer and us as founders!

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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