Casey Wright – CEO, Wright Brothers Inc.

Casey Wright serves as owner and chief executive officer at Wright Brothers, Inc., an agile corporation that provides digital marketing services to the residential real estate industry and operates several eCommerce stores.

Wright Brothers, Inc. was started in 2005 and is currently headquartered in San Diego, California. The company’s growth has accelerated over the last several years, culminating with Wright Brothers, Inc. being recognized as one of San Diego’s fastest-growing companies for four consecutive years (2014 – 2018), and one of Inc. 5000 fastest-growing companies in the U.S. for the last two years.

Casey is also co-host of the award-winning Wright Brothers Podcast and a featured contributor at Huffington Post and Inman News. He lives in New York City with his dog, Titan.

How did the concept for Wright Bros Inc. come about?
In 2004, my parents (real estate agents) asked me to help design an email marketing program to replace their print marketing expenses. Over the next year, their business doubled, while their marketing expenses decreased 90%. Once their friends and colleagues caught wind of it, my phone started ringing off the hook, asking me to erect similar systems for other agents. I began working with new clients whenever I could, on weekends and holidays. Once enough money was coming in to support myself, I dropped out of college and invited my brother to help me grow the business. Thus, Wright Brothers, Inc. was born.

How was the first year in business?
The first year was exciting, but also terrifying. Every meeting felt like it could be “the meeting” to take us to the next level, but we were also barely breaking even and constantly worried we wouldn’t be able to pay our bills or pay ourselves. Looking back now, I’m amazed we made it out of the first year, but we were fortunate to focus on enough of the right things at each stage of our business to make it to the next stage.

What was your marketing strategy?
In 2005, few real estate agents had any familiarity with email marketing. So our first priority was education—showing what was possible with email and creating a desire for our service. To do this, we found we needed a good 15-30 minutes with a captive audience and the opportunity to answer specific questions afterwards. This led us to the strategy of in-person office presentations.

Most real estate brokerages had weekly one-hour meetings, and brokers would typically fill that space with sponsors, such as title companies and mortgage brokers who would cater breakfast and in return get 30 minutes to talk about current market trends and pitch their services. This was the space we wanted to fill, but we couldn’t afford to host multiple breakfasts every week, so we did the one thing we could do—make the presentation so damn interesting and entertaining that brokers would invite us to speak even if we weren’t hosting.

Pretty soon, a common pattern emerged. At the beginning of the presentation, the broker would say, “My colleague said we had to have you in because you’re so good. I don’t think our office is going to get much out of a couple of kids talking about computers, but I said I’d give you a spot, so here it is.” At the end, the same broker would come up and say, “That was amazing. Seriously, the best office meeting we’ve ever had. You have to present at these two offices next!”

At the time, it didn’t feel like we were doing anything strategic. I honestly felt embarrassed that we had to work so hard to make up for our lack of basic business resources. After fourteen years of doing this, I’ve come to see that as the central element of strategic thinking—figuring out how to get what you want with less than perfect resources.

How fast did the company grow during the first few years?
Our growth was fairly exponential during the first few years. We basically doubled our revenue each year for the first four years. Of course, that’s easier to do when you’re starting with very low numbers.

How do you define success?
I really like Ray Dalio’s definition of success: “meaningful work and meaningful relationships.”

What is the key to success?
I think it’s turning the things you want to do into things you like to do. For instance, I want to be the type of person who reads 50 books a year, but the thought of sitting down and reading for an hour makes me feel like a caged animal. I’m an auditory learner and I love to walk my dog around the city, so audiobooks provide a perfect solution. In the end, we always fall back to the habits that are easiest and most enjoyable. With a little strategy, we can make sure these habits pull us towards the person we want to be.

What is the greatest lesson you’ve ever learned?
The compounding effect of habits. Take the previous audiobook example. It doesn’t feel like a big decision to switch from music to audiobooks on afternoon walks, but that simple decision (compounded over time) has brought 450 books into my life—books that now form the entire foundation of my personality and belief system. It really is amazing how time rewards (and punishes) small, daily decisions.

What are some quotes that you live by?
The mantra I try to repeat throughout the day: “I am not my thoughts; I am what I do.” It reminds me that wanting to sleep in doesn’t make me lazy and that being frustrated with someone doesn’t make me a jerk. It’s how I respond to these thoughts that really defines who I am.

What are some of your favorite books?
1) Sapiens: A Brief History of Humankind by Yuval Noah Harari (ostensibly not about business, but my single favorite book)

2) Atomic Habits by James Clear (how to install habits that stick—quick, powerful, and practical)

3) Moneyball by Michael Lewis (amazing true story of how math changed baseball forever—massive parallels to business in 2019)

4) The Better Angels of Our Nature by Steven Pinker (inspiring, fact-based argument that the world is better than ever and getting better)

5) Antifragile by Nassim Nicholas Taleb (how to build organizations, products, and systems that grow stronger as they encounter adversity)

6) Good Boss, Bad Boss by Robert Sutton (should be required reading for anyone that manages other people)

7) The Diamond Cutter by Lama Christie McNally (fascinating true story of applying Buddhist values to business)

Tell me about one of the toughest days you’ve had as an entrepreneur.
The toughest days for me are the days I have to let someone go. We’ve been fortunate to never have to lay people off due to financial constraints, but I’ve had to fire plenty of people for poor performance. I still hate it. Telling someone they’re not good enough to work at your company is devastating. No matter how confident or accomplished you are, hearing that hurts. Being the source of that pain makes me sick to my stomach every time.

When faced with adversity, what pushes you to keep moving forward?
Like most entrepreneurs, I’m terrified of failure and have a love/hate relationship with adversity. Adversity is stressful but it tends to bring out my best work. There’s a real feeling of being alive during the really trying times, in the same way that you really feel alive when you lose a loved one or get your heart broken. It hurts like hell, but there’s a sense of profound meaning and vulnerability—which, properly channeled, can be a source of tremendous strength for an entrepreneur.

What advice would you give to young entrepreneurs?
Sales, sales, sales. I’m amazed at how many young entrepreneurs have these multichannel branding strategies and pitch decks talking about the millions of dollars they’re going to make without acquiring the most basic validation from customers. Release and sell a mediocre product, get data, then get better. Don’t obsess over getting everything perfect. Customers will help you build a better product if you let them, but that conversation doesn’t really begin until you start selling.



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