Rethink Podcast #9 – 6 Entrepreneurship Lessons from a Portland Realtor


If you ask Portland Realtor Tracey Hicks about her five-year goal, she’d say something along the lines of picturing herself on a beach somewhere, enjoying an adult beverage, and monitoring her business from her smartphone.

Hicks is hard to label. Sure, she’s a Realtor. But she is also a marketer, a boss, a mom, a newspaper and magazine founder, an Instagram poster, and the creator of several real estate-related retail businesses. OK, maybe she’s easy to label. She’s an entrepreneur.

Entrepreneurship is hot ‒ even if it means being an entrepreneur within your role as an employee in someone else’s company. Thomas Friedman often tells the story of the waitress who was acting entrepreneurially when gave him extra fruit with his pancakes order that resulted in her getting a 50% tip.

According to the 2016 Kauffman Index, about 550,000 new businesses are launched monthly. However, only 50% of those businesses will reach their fifth birthday, and only a third will make it to their 10th anniversary, according to the Bureau of Labor Statistics.

So, for this episode of the Rethink Podcast, we interviewed Tracey Hicks, a Portland, Ore., entrepreneur in the real estate industry. While her example is not as sexy as an SaaS tech startup featured in Forbes or Inc. magazines, the lessons she’s learned and can pass along to the rest of us are the foundational characteristics that define what it means to be an entrepreneur (and eventually also a better marketer).

“I became an entrepreneur kicking and screaming,” she said. “I grew up in the restaurant business. My parent’s ran restaurants. We were feast or famine my whole entire life. So I was like, I am never going to do that. Ever. And I have not opened a restaurant. That is one thing I will never do. So at least I have stayed true to that. But, of course, when you grow up around entrepreneurial parents, eventually you are going to lose that battle and become an entrepreneur.”

The Courage to Pivot

Hicks became a Realtor in 2005, the height of the U.S. real estate bubble. For a bit of time, she was thinking, “This is fantastic.” We all know what happened next. The Great Recession. Foreclosures. Short sales. Closings that dragged out for a year or more. And Hicks wasn’t getting paid until the closings were finalized. There were bills to pay. Kids to feed…

She pivoted. She worked from home for about 18 months. By the end of that time the Portland market started warming back up, and Hicks was getting a bit of cabin fever. She pivoted again. She and her partner opened their own real estate shop. “People thought we were a little crazy starting a company at that time,” she said. “But as entrepreneurs it isn’t always about what’s going on in the outside world. It is more about what’s going on with you, timing, family, all of that.”

During this period, she also started the newspaper, All Things Real Estate. “I really wanted Portland to have something for their Realtors to market not only their properties, but also themselves.”

She thought she could generate revenue from real estate agents buying ads. “What ended up happening was that the Realtors ended up becoming our readership,” she said.

Again, she pivoted. And she began selling ads to mortgage brokers, home inspectors, plumbers, contractors and so forth. And the newspaper took off, at least within its niche. Five years later, she met two former magazine designers who had just gotten their real estate licenses. One thing led to another, and she pivoted again, this time converting the newspaper to a monthly magazine.

“Being an entrepreneur, there are a lot of pivots,” Hicks said. “You just have to be able to handle that, and be OK with change, and learn from your mistakes … And you really have to be able to shift to what your consumer, your client, your customer is telling you, what they’re doing, and what they’re buying.”

Follow Your Passion

OK, I know what you’re thinking, ‘How do you know where to pivot to?’ And when you look at Hicks’ example of starting a newspaper targeted to real estate agents, it isn’t the most obvious choice. Around the country then, and likely now, newspapers were going out of business or going online.

“First things first, you have to do what you love, because it is going to take a lot of your time and you’re going to lay in bed at night at 12:30 a.m. and remember you have to post to Instagram or you have an idea in the middle of the night and you have to write it down,” she said.

Folks were telling her to create an app instead. “I just love the picking up of a newspaper and the touch and the feel. It’s kind of nostalgic in a way. … And there is always a time where somebody is sitting somewhere, where they’re going to pick it up and read it.”

Know Your Industry

Hicks’ several business endeavors include her real estate practice, the newspaper/magazine, an ecommerce retail shop, and now a brick-and-mortar retail store. However, they are all tied to real estate.

“All these start-ups … You have to start someplace, I guess” Hicks said, laughing. “People are saying, ‘You have so much going on!’ but it’s all real estate. It’s all related. It’s not like I’m trying to do a horse farm, sell real estate, and plant avocados.”

Starting a business on what you know is typically a key to being one of those companies that celebrates its 10th anniversary. And you’d be surprised just how much you know. It could be your knowledge comes from past professional experiences, or from consuming a product personally, or from having a passionate hobby that then becomes your business. The list goes on. On the flip side, the less you know about what you’re jumping into, the more time, money, or other resources it will take to get that knowledge.

“I know what realtors want,” she said. “And I know what they need ‒ even with them not knowing what they need.”

Find a Market Need

Hicks had her “Aha Moment” for her first retail product, a home buyer’s journal, while showing homes to a picky friend. She realized they could use something to jot down what they liked or didn’t like in a home, how they felt about each house, and so forth. Hicks realized these journals could be custom branded and given away by real estate agents and mortgage brokers to customers.

“My whole goal,” she said. “Real estate products have been so ugly for so long, and I just got tired of it and I just wanted to change the look of real estate.

“In real estate, it is so important to stand out,” she said, especially if you’re part of the one of the big brand networks. “Everybody that comes into the store or goes to our site gets so excited. It’s all about marketing. It really is.

Always Be Marketing

One thing all successful real estate agents figure out quickly is that they need to always be marketing and thinking of creative ways to always be marketing.

With each order shipped, Hicks includes a copy of the All Things Real Estate magazine. Customers get a suggestion to take a picture with their ordered products and then share it on Instagram, Facebook, and other social media with the #AllThingsRealEstate hashtag. She then shares all that user-generated content (a marketer’s dream) via the store’s social channels.

She estimates the All Things Real Estate store sends out 30 to 40 packages per day throughout the country, and even internationally, to Canada, Japan, and Russia. “Instagram and Facebook does that,” she said. “You get to reach a whole new community that you just didn’t have access to prior to social media.”

Customers also receive a welcome email that shares Hicks’ origin story. And she’s learning from mistakes, such as dumping an unengaged acquired email list, and instead building a better one from scratch.

“There are going to be some things that we do fail at, but as long as we’re learning from our mistakes then I totally don’t mind making mistakes,” she said. “That’s how you learn. That’s how you figure things out.”

Find the Right People

Another key to being a successful entrepreneur is building a great team. If you’re the creative one, then go out and find the analytical partner. In my own experience participating in start-up weekends (where different folks come together and start one or more businesses), the teams that come out often include a tech person, a marketing person, and a sales person. Hicks references ideas attributed to Michael Gerber’s E-myth, which advocates that owners should be working on their business and not in their business.

Hicks is quick to give credit to her real estate partner, her graphic designer, and her store manager for her business success. When she talks about the future, she’s thinking of ways to give her employees ownership.

Now … about that end goal and where she sees herself in five years?

“I have always wanted to create a life for myself and for my family that allows me to run a business remotely,” Hicks said. “The way business works today allows that, whether it’s email marketing, social media, and so forth. My problem is I’m having so much fun right now.”