Caleb Elston – Co-founder and CEO of Delighted

We’ve always focused on how do we deliver an experience so good that people can’t help but tell others about it.

Caleb Elston is co-founder and CEO of Delighted, the fastest and easiest way to gather actionable feedback from your customers. Prior to starting Delighted, he led the team that created Mosaic, which was featured by The Today Show, Apple, USA Today and others. Before Mosaic he founded Yobongo, which was acquired in March of 2011. Caleb was also the vice president of products for

Where did the idea for Delighted come from?

My co-founders and I have been building products and one of the challenges we experienced at each company was how to incorporate customer feedback into that process. At a previous company, we had been gathering feedback from customers using a cobbled together collection of tools: a simple survey tool, an email marketing tool to deliver the survey, a business intelligence tool to make sense of the data, presentation software to make and share reports with the team, and human effort to categorize responses that needed to be followed up with by customer support. We weren’t happy with this approach and were looking for a better way, but we couldn’t find anything that was both powerful and well-designed. So, we spoke with friends about how they were solving this problem, and we found they were having similar challenges at their companies. Delighted is our approach to solving the problem of how to use real customer feedback to make your product or service better.

What does your typical day look like and how do you make it productive?

My typical day has me responding to customers, since I still get a small percentage of our customer support requests each day. I want to make sure I have a grasp firsthand on what we are doing well and what we can improve most for new and existing customers. We are also always working on new functionalities for the product, which will be somewhere along the spectrum of being in early idea stage, design review and critique, early testing on our staging environments, ready for preview-rollout to customers or ready for full rollout. I will also usually have one or two projects that are happening in the company that I can have a unique impact on so that can be a launch of a new product, recruiting, longer-term roadmap planning, or more. Staying productive isn’t hard when there are so many projects that are all advancing quickly and we have a constantly growing customer base to support and ensure are successful. There is no shortage of ways our efforts can make the experience of Delighted better.

How do you bring ideas to life?

This is a deceptively complex question. If I were to distill it down to the essence, for us it comes down to making sure we deeply understand the problem we want to solve, the pain we are going to alleviate, and then exploring the many different approaches to solving that problem, taking into account the various constraints. And ultimately after you have an idea of how you’ll solve that problem, you start building it or implementing it. Some ideas are small enough in scope that only one person is involved, but some ideas are such that they benefit from many people being involved. Ultimately you need both the insight into the idea to come up with a solution and the technical ability to make it happen. We are fortunate to have an incredible team who are amazing at that entire process.

What’s one trend that really excites you?

I love that the quality of the products we all use continues to increase. If you think back to the software you’d use at work even just 10 years ago, it wasn’t very good. People are used to high quality software due to the pervasiveness of smartphones and the internet broadly. Now, people expect the products they use at work are just as easy to use, well-designed and powerful as the products they choose for themselves at home. The days of complex, hard to use, ugly software are numbered.

What is one habit of yours that makes you more productive as an entrepreneur?

When working, I turn off social media.

What advice would you give your younger self?

Take more math and computer science courses.

Tell us something that’s true that almost nobody agrees with you on?

A small team can do more than a large team. I think in general, people believe if you have more people working on a project or in a company, clearly that company will be able to do more. But I’ve found that within certain ranges, say five versus 15, or 10 versus 30, often the smaller team or company can both be more productive and create something more loved.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I think through the question, “What is the next most important thing we can do?” and I work to get that done either alone or with the team, depending on what it is. For example, we didn’t build credit card collection into our product on day one – we didn’t have a way to accept payment. We built that when folks were getting value from the product and were asking us where to pay. Why? Because it allowed us to focus on the other parts of the product that would make it valuable to customers, such that they would want to pay us.

What is one strategy that has helped you grow your business? Please explain how.

We’ve always focused on how do we deliver an experience so good that people can’t help but tell others about it. The standard for business software is quite low, people generally expect low quality products, support that is automated and not helpful, pushy salespeople, incomprehensible documentation and obscure pricing. We do our best to ensure every aspect of doing business with us is great. No part of the experience is too small to warrant thinking through the question, “What would make this the best experience possible?”

What is one failure you had as an entrepreneur, and how did you overcome it?

In one of my previous companies, we were fortunate to get a lot of press from folks like The New York Times and The Wall Street Journal. It felt great, and generated a lot of attention and even some users. But ultimately, it was a distraction. I took the press as validation that we were doing great, but the real situation wasn’t so rosy. I confused attention with fundamental success. You need to look to your customers and their experience with your product or service for the real validation.

What is one business idea that you’re willing to give away to our readers?

There are currently two main ways people in the U.S. deal with where they live: they either rent or own. I think there is an opportunity for something in between – a way that you could have the benefits of being in a single-family home and build some equity, without the negatives of having a massive part of your net worth tied up in a single asset.

What is the best $100 you recently spent? What and why?

They were more than $100, but Apple’s AirPods are incredible. They are the sort of product I remember thinking, as a kid, was science fiction.

What is one piece of software or a web service that helps you be productive? How do you use it?

Slack. We use Slack as our core messaging system at Delighted and as a remote team, it is incredibly important to stay in touch and get closer to a feeling of presence.

What is the one book that you recommend our community should read and why?

“Setting the Table” by Danny Meyer. Danny Meyer is the restauranteur behind restaurants such as Gramercy Tavern, The Modern, and even Shake Shack. Danny shares how his focus on generous hospitality has led to his restaurants resonating with customers. I find the intense focus on the details of the diner’s experience and showing them great respect and care to make their dining experience special incredibly applicable to businesses beyond restaurants. Everyone wants to be taken care of and remembered by the companies they do business with. Danny shares how he developed this philosophy and how he implements it across his various restaurants, ranging from fine dining to fast casual burgers.

What is your favorite quote?

“The way to get started is to quit talking and begin doing.” – Walt Disney


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