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Kevin Gindi of Cheeky: “Don’t be afraid to price your product fairly”

Don’t be afraid to price your product fairly. We iterated on price many times over because we were worried people simply wouldn’t buy at certain price points. If you build an amazing product and experience, that will resonate with people. Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started […]

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Don’t be afraid to price your product fairly. We iterated on price many times over because we were worried people simply wouldn’t buy at certain price points. If you build an amazing product and experience, that will resonate with people.


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 Kevin Gindi.

Created senior year of college, Kevin Gindi, Co-CEO, launched Cheeky after losing his expensive dentist-made night guard that alleviated pain from constant teeth grinding. After realizing there was not an affordable and quality night guard on the market, Kevin partnered with his twin brother, Jack and friend, Samuel to create Cheeky. As the brand lead, Kevin oversees customer experience, product development and overall growth of the brand.


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?

The idea for Cheeky was born out of necessity. Jack, my cofounder and twin brother, and I are both very heavy teeth grinders. During our senior year at Boston University, I lost my extremely expensive night guard I had purchased from my orthodontist in New York. I suffered for weeks not being able to sleep well, not getting any luck from “boil and bite” night guards purchased from the local pharmacy. At a certain point, we found that there was no company offering dentist quality night guards at affordable prices. The moment we graduated college, we started Cheeky out of a small co-working space with nothing more than a 3D printer and a make-shift website.

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

I was laying in bed for the 10th night in a row, unable to fall asleep, because I had lost my custom night guard and my teeth weren’t protected. The boil and bite guard I bought from a local pharmacy wasn’t working. I realized that other people must be suffering like myself. That was the inspiration behind starting this company. A few months later we were able to gain a significant amount of leads — finally getting to interview teeth grinders. We found that the overwhelming majority of teeth grinders we surveyed were pretty desperate for what we wanted to build. Helping all teeth grinders remains our most powerful motivator today.

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?

The biggest support base we have is our family. Business can be an up and down and it is important to have a strong group of people who support you unconditionally. I remember calling my father and telling him I wanted to start a start-up for teeth grinders. Where my friends laughed, he offered support and words of encouragement. Without that, it would have been a lot harder to have the courage to even begin building Cheeky.

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

Our product. We pride ourselves on shipping quality night guards, fast. It is validating hear from our customers about how our product has positively impacted their lives and they thank us for helping them sleep when nobody else could. That means the world. We offer the most options to customize your night guard on the market. We do that because we know every teeth grinder is different and we want to be able to serve everyone.

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

I try to bring goodness into the world by treating our team of amazing employees like family and by putting our customers before ourselves constantly. Inherently the better we do the more goodness comes into the world, since our product actually helps people live their lives in a better way.

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?

  • Resilience

We have had many ups and downs throughout our journey. The main component to Cheeky’s success has been our ability to respond to adversity with real solutions. Being three non-dental founders right out of college, it would have been very easy to close up shop and say it was not possible. But we decided this problem was too important not to be solved.

  • Solve a real problem

Before launching, make sure the problem you are solving actually exists. It is very easy to start at the solution and work your way back. However, that strategy will set you up to fail. Speak to real people and actually try to sell some product before you decide to go all in on something that does not exist. We did not feel 100% confident in our business until we spoke with real people and collected preorders. If you do not speak to your customer consistently how will you know what they want and need?

  • Work with people you love

Running a startup can really consume the founding team’s whole life. You are going to be living and breathing the company you found with the people you start it with. You need to be really comfortable being angry, happy, silly, serious, and vulnerable with the people you work wirth. Jack is my twin brother and Sam is one of our oldest and closest friends. Having them makes doing something as hard as building a start up a lot easier.

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?

This is a great and hard question. We’ve been really lucky to have surrounded ourselves with incredible people who only want us and Cheeky to succeed. However, there are people in the startup ecosystem who are not high ethics people, I would say the only bad advice we’ve received were from people with ulterior motives. Be careful when vetting potential investors or advisors, because not everyone is as nice as you think they are.

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

We launched Cheeky with zero knowledge on how to create custom night guards. Jack, Sam, and I had countless sleepless nights rolling around in doubt as to whether we could actually ship this product. We had to constantly iterate on our product and process and rely on the patience and conviction of our customers to get our product to where it is today.

Different anecdote, we were interviewed and rejected twice by Y- combinator. Being told no twice by really smart people can be devastating. Make sure you believe in the problem you are solving, the solution you are providing, and the team you are working with to get through the lows.

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?

My team, family, and customers have been the main reason why we have been able to be as resilient as we have been. When things get anxious and stressful, I try to remind myself why I am doing what I do, and how blessed I am to be doing it.

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”?

Founders need to surround themselves with other founders. It helps to be reminded that the problems you face are not unique at all. Many people are going through the exact same things you are and have advice on how to get through it.

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?

We started Cheeky completely bootstrapped. That experience was great for us in the moment but also has its cons. The best thing about being bootstrapped is you can run your business the way you see fit and do not have to answer to anyone else. You can move at your own pace and not worry about meeting anyone else’s expectations. However, the main benefit we have found from raising vc is -. It helps to have hardworking, talented people care about your business. If you are deciding whether or not to raise vc ask yourself, do I need vc to get to my goals? Or am I raising Vc for some other reason that does not benefit my business.

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.

  • Solve a real problem

Cheeky started because I truly could not sleep. It feels so great to be the main customer of my own product.

  • Make sure the solution you provide is working

It is important to ensure that your customers love and use your product to solve that problem. In our case, if a night guard is not working, they simply won’t wear it.

  • Price your product correctly

Don’t be afraid to price your product fairly. We iterated on price many times over because we were worried people simply wouldn’t buy at certain price points. If you build an amazing product and experience, that will resonate with people.

  • Listen to your customers

Focus on customer service as often as you can. I find that no practice gives me a better idea as to the state of our experience than going through our customer service reps tickets. I can see trends in fulfillment and product issues and fix it quickly. Any founder must consistently speak with their customers. A startup is a living breathing being that evolves every day. The only people who will give you real feedback on whether you are supporting that evolution are your customers.

  • Plan to scale both product and distribution

We manufacture everything in house. Nothing hurts great distribution like low-quality products and experience. It is important to see trends before they happen so you can plan accordingly and not be reactive.

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?

If one customer is having an issue, it is very likely a cohort of customers is having that issue. Our customer experience is so dependent on the people on our team. From fulfillment to manufacturing, every part of our process needs to be overseen and quality controlled to ensure we are always getting it right. Initially we were not as receptive to problems that would turn into problem trends. We are not extremely diligent on how our process needs to change and evolve, as our scale and customer base does.

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?

To be honest, this is a problem we struggle with as well. Jack, Sam, and myself have often felt overworked. I think it is important to allow yourself a day or two to relax and reflect without feeling guilty about it. ( IIn my opinion, allowing yourself to breathe is the best way to cure burn out

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.

I’d love to sit with Andy Puddicombe, Co-Founder of Headspace. I find it really interesting that he has started both a movement of presence and calm, while also creating an unbelievably competitive and ambitious startup space.

How can our readers further follow your work online?

You can find us on Twitter and Instagram and Facebook @teamcheeky and can also find out more about us at getcheeky.com

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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