How Ryan Dossey Pushed Past Fear to Lead a Happier, More Successful Life

Lead from a position of strength.


6 min read

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In this series called Member Showcase, we publish interviews with members of The Oracles. This interview is with Ryan Dossey, founder of Call Porter, a support company for real estate investors. It was condensed by The Oracles.

What was a defining moment early in your life?
Ryan Dossey: Growing up, I watched my grandfather bust his back as a pharmaceutical sales rep. He and my grandmother grew apart as a result, and she got heartbreakingly bitter, so it was incredible to watch them fall back in love when he retired.

But then, she had a stroke 12 months later. She forgot his name, and her mental capacity reverted to that of a 12 year old. Now he’s her caretaker. He worked so hard for decades to enjoy just one year. That’s what made me decide that “normal” wasn’t good enough and I wasn’t going to spend my life hustling.

How did your business get started?
Ryan Dossey: I grew up watching my dad run his businesses with perfection. He has been an incredible example of integrity and hard work. The problem was that he could never hire, grow, and scale. It was always just him.

I started Call Porter, a full-service real estate call center, because I wanted to be a business owner, not a solopreneur. The goal was to allow real estate investors to focus on what makes them money. It’s been incredible to hear testimonials from firefighters, doctors, and full-time investors about what we’ve helped them accomplish. My buy-and-hold real estate business simply couldn’t function without it. Thanks to Call Porter, the team hasn’t taken an inbound call in three years.

What are you more skilled at than most people in the world?
Ryan Dossey: My areas of expertise are direct-to-seller real estate marketing and building systems. I find off-market deals on houses and apartments at 50 cents on the dollar, while also leveraging tools and building teams. I’m a firm believer that you can build a business that either serves or enslaves you. Ultimately, it’s your choice.

Here’s a perfect example of how these skills can work together for a profitable, efficient business. A few months ago, I went on a two-week vacation to Paris with my wife. During that time, my staff contracted $1 million of property worth, raised the private funding, closed the deals, and started the construction — and my phone didn’t ring once.

What book changed your mindset or life?
Ryan Dossey: I honestly didn’t know whether I would ever share this, but the book that changed my life was, “No More Mr. Nice Guy” by Robert A. Glover. I was raised in a conservative, middle-class family with many issues around money and success. Not rocking the boat was my goal in life. My subconscious would freak out whenever I was successful, which came from a deep-rooted fear that I wasn’t supposed to have more than “just enough.” If I had too much love, money, or happiness, God would take it all away. So, instead of showing up wholly, I’d only give 70 percent when it came to power, love, and intimacy. This meant that I held back in business, rolled over in relationships, and dialed myself back in general.

This book was the catalyst that led me to go to therapy, which changed my life. I still have to keep my “nice guy” tendencies in check, but now, I stand up for myself and lead from a position of strength — while enjoying success instead of fearing it.

What was your biggest challenge starting up? How did you overcome it?
Ryan Dossey: I really struggled with money. I didn’t know how to make it, keep it, or invest it. In the first few years of my real estate company, I treated the business like a slot machine, throwing money into it and hoping it would pay off. In 2016, I bought and sold six houses — barely scraping by.

The next year, I bought and sold 74 houses. I turned the corner by treating my business like a business, tracking KPIs (key performance indicators), and being consistent. The lessons I learned allowed me to take Call Porter from a sloppy, three-person operation to a seven-figure company that handles over 10,000 calls a month for elite investors around the U.S.

How do you define great leadership?
Ryan Dossey: Great leadership is about building people up, doing what’s best for the company, and making it fun. Too often, employees show up, do work they don’t like, collect a check, and leave the same. We focus on developing our staff as human beings — so much so that personal development is one of our core values. We’ve been known to pay our staff for reading books of their choice. If an employee leaves to strike out on their own, it’s the highest compliment they could ever give us (assuming they aren’t starting a competing business!).

How do you evaluate a good business deal?
Ryan Dossey: A good business deal is all about lifetime value. Never give up equity because you need cash in the short term. And never negotiate from a position of need or lack. If you’re in that spot, don’t let anyone see you sweat!

When evaluating business deals, I visualize hitting all my targets. I recently turned down an opportunity to sell a piece of one of my companies because it wasn’t a win-win in the long term.

What’s your daily routine for success?
Ryan Dossey: My most productive days have this recipe in common: I get up earlier than I need to, exercise, take a cold shower, meditate, and don’t check my email or social media for several hours after I wake up.

If you ever start a charity, what would it be called and what would it do?
Ryan Dossey: I want to have an investment portfolio where all the proceeds support charities I care about. I’m especially passionate about helping end human trafficking. But instead of writing checks, I’d like to build an engine that funds the organization. It would also be cool for our residents to know that their rent helps save lives. I’m not sure how it will work yet, but that’s my passion project.

What is the most exciting question that you spend time thinking about?
Ryan Dossey: I’m a marketing nerd, so my favorite questions have to do with next-level prospecting. I think about how to turn funnel opt-ins into prospects, predict who will call an investor before we market to them, and how to get in front of the right people and avoid those who aren’t interested. I also think about how to add so much value that our sales calls are simply onboarding conversations.

Connect with Ryan on Instagram and Facebook, or visit his website.




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