Happily sounds like such an interesting company! What brought you to this specific career path?
You know, ever since a young age, I’ve always been intrigued by this concept of business. My dad ran his own business for 20+ years, and I just always thought it was cool to create a product and try to get people to use it. I’ve had some big ideas over the past 25 years of my life (most if not all of them, terrible ones), and there’s just something about trying to bring your vision to life and add value to the lives of your customers and community. The idea of beginning with nothing, and building something – i.e. entrepreneurship – is just really fun to me.

Can you tell us a story about any hard times that you faced when you first started Happily and how you overcame them?
Oh, absolutely. Most people only want to talk about the glamorous parts of building a startup, but the reality is there are far more failures than successes, and there are far more frustrating or challenging days than there are easy ones. Building your first product is hard, getting customers is tough, hearing negative feedback from customers doesn’t feel great, but at the end of the day, I really believe taking it one day at a time is the best approach – and there are certainly victories and great days along the way that should make any entrepreneur very motivated and proud.

Happily is known for its “date in a box” date nights, which send everything you need for a thoughtful, creative date straight to your door.

How is the rebrand and Happily launch going?
It’s been great. I’m super excited for the direction that our company is headed. We are hard at work introducing our new products to our customers and learning how we can continue to support the relationships and marriages of the couples in our community. I couldn’t be more proud of our team for all of their hard work, and I’m really excited with how the new brand, design and products turned out.

What do you think makes Happily as a company stand out? Please provide a specific example.
I think the thing that I love about Happily is that we do a great job making relationships fun. Being married or being in love should be the biggest joy in our lives, but we often times treat it as an inconvenience! When I look at all the different products and services on the market designed to help couples in their relationships or marriage, they all have such a serious, and often times negative context or origination to them. I think what makes Happily stand out has been our ability to take a light-hearted approach to being intentional with your partner or spouse, and when you look at our products they reflect that. They’re fun, inviting, easy to use, and budget-friendly for all couples, because we want all couples to feel invited into this community that we’re building. I just don’t think there are many companies in our space that can say that.

Happily’s “Love Notes” send a handwritten note to your spouse or partner, all from the convenience of your phone or computer.

What tips would you recommend to other startup founders to help them to thrive and not “burn out”?
This one is really tough. I will say, if you don’t legitimately, genuinely enjoy working, being a startup founder is probably not for you, because that’s your life and you have to own it. That being said, I think it comes down to finding balance where you can, and also identifying what it is that helps you disconnect and separate yourself from your work. For me, I try and make sure that I spend time with my wife doing things we love. I try to play basketball four to five times a week because that helps take my mind off work, and I also have other various hobbies that I love. I think finding ways to mentally disconnect is the biggest part of avoiding burn out.

None of us are able to achieve success without some help along the way! Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?
Wow, I feel like an entire separate interview is needed for this one, there are so many. My wife Devon first and foremost. She sacrifices so much and supports me better than I deserve. All of our investors, starting with my parents and in-laws who were the first to believe in me and this company. Jeff Cherry and Marcus Morrison, two of my co-founders who have been with me since day one, and still are to this day, and all of our employees who work so hard, and with such great passion everyday to make Happily what it is.

What are five things you wish someone told you before you started your company?

  1. Prepare to work 10x harder than you ever have.
  2. You don’t know what you don’t know. Don’t be afraid to ask questions and admit when you don’t know something. The fastest way to learn, is to ask someone to teach you.
  3. Everyone thinks they have the answer and can do your job better than you.Trust your gut, most of the time it’s right.
  4. Hire people that are smarter than you.
  5. Don’t be in too much of a hurry to try and scale, figure things out while you’re small.  If it works with 100 customers it will work with 1 million.

For more information on Brett’s story and the Happily brand, visit them online or on social media @thehappilyco.