About Ryan

Hi! My name is Ryan Waggoner, and I train freelancers to be unstoppable. If you’re new to this site, you should start here.

This website exists to help you, but I’ve also found it’s useful for readers to know a bit about its author (me) and where I’m coming in the resources I offer. So this page is one of the few places on this site where I talk at length about my own background and story, after which you can never think about it again.

Thanks in advance for indulging me.

Quick bio

Note: if you need headshots or bio for publication purposes, check here.

Hi, I’m Ryan.

I’m a software engineer who has been a full-time freelancer since 2007. My first few years of freelance were really tough, I racked up a huge amount of debt and came very close to total failure. But I managed to figure it out, and for years I’ve consistently earned at least $250,000 from consulting clients.

In 2015 I launched Everleads, which curates the best freelance jobs for developers and designers and delivers them daily via email. This method was how I got most of my leads during my early years of being a freelancer, and I’ve taught it to many others who have found great success with it.

In 2016 I started working on a course for freelancers called Freelance250k, and now hundreds of students have taken it. I’ve got several new courses and products in the works to launch in 2019.

I’m incredibly proud and humbled that tens of thousands of freelancers have subscribed to my newsletter, followed me on social media, and purchased my products. It gives me incredible joy to have the privilege of teaching others the lessons I’ve learned on my own journey.

I’m in my 30s, my wife Alexis is an ordained minister, and we have one daughter, Junia.

We live in NYC, and are madly in love with this city. If you’re ever here, look me up (see open invitation section below).


I saw Derek Sivers do this on his about page and I really appreciated it, so I’m going to replicate it here, although mine is longer and more detailed because I’m more of a narcissist than Derek is.

1982, South Florida: I enter the world as the first child of a couple who were 20 years old when I was born. That’s way too young to be having kids!

1982 – 1995: I grow up in a few cities in South Florida. My life revolves around church, family, and books. My parents have two more boys and a girl, and we’re all homeschooled.

Early 1990s: My dad acquires some old computers, including a TRS-80 and a Commodore 64. I start to learn how to program.

Sometime in 1995: Our family moves from Florida to Colorado so my Dad can work at a now-defunct nonprofit there.

August 1997: I finish 8th grade and transition from homeschool to a small private Christian school in Colorado Springs.

August 2000: I decide not to return to high school for my senior year. I’m only a semester’s credits short of graduating, so I decide to just take community college classes, which also give high school credits.

September 2000: I miss the deadline for community college classes, but I also can’t return to high school at this point. I’m now a high school dropout. Good job, Ryan. Fortunately, I have enough credits to rejoin my class in the Spring semester and still graduate. I decide to keep delivering pizza for this semester.

October 2000: Bored with delivering pizzas, I naturally enlist in the Navy. I’ll leave the following summer after I graduate high school.

January 2001: I rejoin my high school class for the last semester before graduation. I need an elective during a period where the only thing will work is a pre-calculus class I had already passed. I take it again as an elective. I meet a girl in the class named Alexis who is a military kid and has just joined our class for senior year (but I wasn’t there in the fall semester, when I was a high school dropout). She’s not a fan of math, but she is a fan of MxPx. I’m mildly interested.

February and March, 2001: My interest grows.

April 2001: Alexis and I start dating, even though we’re about to graduate. She’ll be heading to California for college and I’ll be heading to the Navy. It’s unclear why we’re doing this given it has no future, but we decide to deal with that later.

May 2001: I graduate high school.

July 2001: I leave for Navy bootcamp. It’s hard and depressing leaving Alexis, but the Navy doesn’t care. We decide to date long-distance.

July – September, 2001: Bootcamp is hard, fun, and interesting. I could write a book about my experiences here, but I’ll leave it for now.

September 13, 2001: I graduate bootcamp two days after 9/11, and my time in the military was completely transformed as a result.

June 2002: After almost a year of training at various places in the US, I’m shipped off to Sicily, Italy, where I’ll spend the rest of my time in the Navy. This was the first time I had been outside the US, and it was unbelievably scary and transformative.

January 2003: Alexis comes to visit and I propose. We set a date to get married in January 2004, one year later. She’s rocketing through college and will end up finishing 18 months early.

January 2004: I make the best move of my life and marry that girl from my math class. Alexis and I have been dating long-distance for the last two and a half years, during which time she has rocketed through college and graduated early. She moves to Sicily to be with me while I finish my last 18 months in the Navy. I’m 21 years old.

January 2005: I get out of the Navy six months early so I can finish school. I have about a year’s worth of college credits from classes taken over the last few years. We move back to Colorado Springs and buy a 4plex as an investment. We live in one of the units while I attend school.

January 2005 to June 2006: I take as many classes as the dean will let me, plus some more classes at community college. At one point I’m taking 8 or 9 different classes for more than 30 hours of credit. I’m exhausted.

Early 2006: We almost get divorced. It’s a long story and not really the type of thing you post online, but we got a great therapist and she helped save our marriage.

June 2006: I graduate summa cum laude with a BS in International Business from the University of Colorado at Colorado Springs. I’ve been a straight-A student and I have a 3.93 GPA. I’m the first in my entire extended family (that I know of) to get a bachelor’s degree.

July 2006: We move to San Francisco without jobs or knowing anyone. I have no idea how we managed to rent an apartment, but we got an amazing tiny little studio near Union Square.

September 2006: I land a job at CNET as a product manager. I enjoy the work, but still want to do something on my own.

July 2007: I start freelancing on the side. I charge $50 for PHP web development from someone I found on Craigslist. It’s fun and easy and rewarding.

August 2007: Emboldened, I quit my job to freelance full-time. Alexis does the same thing a week later.

2007 to 2010: We struggle hard with freelancing and with finances. We almost give up and leave freelancing and / or San Francisco many times, but we stick it out. We gradually get the hang of freelancing successfully. I transition to doing iOS development in 2010.

2011 to 2012: We move to Portland so I can participate in PIE with a friend. Our startup fails. I keep freelancing throughout. The income from freelancing has become life-changing for me. I’m now able to consistently earn at least $250,000 per year, which means we can live well, take time off, travel, put a lot of money into retirement, and make other investments.

Summer 2012: We spend two weeks exploring Europe in a convertible for my 30th birthday and then move to NYC for Alexis to get her Master’s in Divinity from Union Theological Seminary.

2012 to 2015: We get to know NYC, make amazing friends, earn great money from freelancing, and generally just have one of the best seasons of our life.

April 2015: We have our first kid, a girl. Life will never be the same.

May 2015: I launch Everleads, a service to help freelancers find new clients, and I start writing about freelance to promote it.

June 2015: We move to Nashville. We want lower cost-of-living, lower taxes, and a slower pace of life. We do a careful search of many cities all over the US, and finally pick Nashville.

2015 to 2018: We live well in Nashville, working hard to get to know it, to make friends, and to get as much out of the city as possible. We enjoy it.

March 2018: We move back to NYC. Read this for a lot more context. We have no plans to ever leave again, unless it’s to live overseas for a few years before returning to NYC.

February 2019: I write this page.

Habits > Goals

I’m a big fan of focusing on habits and systems over goals and outcomes. I do have some goals, because I think they’re helpful in stepping back and thinking about where you want to go, but I try to spend 80% of my time focused on the inputs and daily / weekly habits which will get me there.

The Mighty 5

I currently am tracking 5 daily habits, which I do Monday through Friday.

  1. Exercise for 60 mins
  2. Read for 60 mins
  3. Write for 60 mins
  4. Deep work for 4 hours
  5. Devices off at 830p

I’m not going to lie, this is really challenging. In particular, the “4 hours of deep work” and “write for 60 minutes” habits, which require a level of intentionality around my daily planning which doesn’t come naturally.

I also have several others I try to do daily, though not as strictly:

  • Meditate
  • Stretch 2x
  • Check finances
  • Post on Instagram

Finally, in 2019 I’m trying to publish one substantial (500+ words) page or post every single day. I’m writing this page on Sunday night in mid-Feb to be able to publish it today. We’ll see how long this habit lasts though. Not sure it’s sustainable.

Random tidbits

I love international travel. I’ve visited dozens of countries, with too many favorites to list. Were I rich and single, I would travel the world for the rest of my life.

I go on 3-5 cruises per year by myself. I know, it probably sounds odd, but I find it a cost-effective way to escape, relax, and have time to think and write.

I’m a certificated private pilot, though I haven’t flown in years.

I’m an open water diver, and I usually dive several times a year while traveling.

I’m an active residential real estate investor.

I’m a runner, at least when I’m not injured, as I currently am as I write this. To date the longest race I’ve run is a half-marathon, but I’d love to run the New York City Marathon once.

I live to read. Every year I have a goal of reading 100 books, though I usually don’t come close. But I’m getting better over time, and I’ll get there eventually. You can track my books and ratings on GoodReads.

Open invitation

I love having quality conversations with interesting people. If you’re ever in NYC and you’d like to grab a coffee and chat, let me know and we’ll try and make it happen.

I will usually update Instagram, Twitter, and my now page when I’m going to be traveling outside of NYC, so if I’m going to be in your neck of the woods and you’d like to meet up, contact me!

Connect with me

Let’s connect! I’d love to get to know you and see if we can help each other. Here’s what I’d suggest:

  1. First, make sure you subscribe to the newsletter. It’s the best way to keep up-to-date on everything that’s going on.
  2. The now page will keep you up to date on what I’m focused on at the moment.
  3. You should follow me on Instagram and Twitter, where I share stuff from my daily life, as well as ideas and tips on freelancing, entrepreneurship, habits, goals, travel, and much more.
  4. You can read my blog posts, which are usually a lot more informal and “behind the scenes” about my business and my life than the rest of this site.
  5. You’re always welcome to contact me! I don’t respond as quickly as I’d like, but I almost always respond. Please be patient with me.

Thanks for reading!