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Tanned,Rested, And Ready: Tyler Giles' Life On the Run

  • 12 min read

Tyler Giles is a friend of mine, a dedicated lifter, an ultra-marathon runner, and an international mergers and acquisitions attorney. We met in law school at Florida State University in Tallahassee, Florida before he transferred to the University of Georgia. Unlike me, he was a stand-out at FSU Law. Like me and the people I gravitated to, he was a bit older. He was smarter than most of us. He was way more jacked than the average law student. He was certainly more tattooed. 

I started chatting with Tyler pretty early on and we realized we liked a lot of the same music, were both from north Georgia (me from Athens, him from Stone Mountain), were both into fitness and the outdoors, and were both in the military. We stayed in touch after he transferred and since then have managed to support one another in our respective ultra-running efforts. As an example of what a great dude he is (and how cool his wife Jennifer is), in 2017, Tyler and Jen ran the Raccoon Mountain Marathon in Chattanooga, Tennessee on a Saturday morning, drove to Lake Martin, Alabama after they finished, and met me in the middle of the woods at midnight to pace me for the last 50 miles of the Lake Martin 100 miler. They each ran a second marathon in 24 hours then hopped in the car and drove back to Atlanta.

Tyler grew up like most of us in North Georgia in the 70s and 80s; playing in the woods, fishing and swimming, and riding dirt bikes. Less typically in SEC football obsessed Georgia, he was a gymnast until he was 17. He says the body awareness and control he learned in gymnastics helped with judo when he started that college, and certainly make workouts on the rings a little easier now. He credits being a gymnast in the Southeast with making him comfortable living outside conventional societal norms. Now he’s a Mergers & Acquisitions attorney, negotiating and documenting the purchase and sale of businesses around the world. Tyler has been very successful in his law career and is passionate about sharing that success with his fellow veterans, whether that’s offering advice or helping people locate jobs. I asked him to talk to me about it because I want to expose the SOFlete community to “regular people”, especially transitioned veterans, who are having great success in a (semi) normal job while still pursuing the ragged edge of life in order to Die Living.  

Ironically, Tyler’s comfort with being outside society’s norms lead him to the Army before he found legal success. His own words probably do better justice to his story, so here’s our Q&A: 

Why did you join the Army? 

I had dropped out of college and was hanging out in the punk scene in Atlanta working in restaurants, getting in bar fights and pretty much trying to find some sort of edge where I truly felt alive. After a 3 AM right arm session my buddy and I decided we would join the Marine Corps the next morning. This was pre-9/11 and my buddy had previously been arrested for discharging a firearm in the city limits so the Marine Corps recruiter told him he would need a waiver. It was a flare, shot via shotgun in a deserted mall parking lot at night and he got nabbed by a mall cop, it’s still funny today. Not to be delayed by a waiver, we ended up at the Army recruiter next door who lied about his waiver and told me my AIT would be “like college with beer”. Imagine my surprise when the JFK Special Warfare Center representative showed up to scoop us up from basic training saying “basic was easy, welcome to hell”. Luckily, he was just fucking with us. But no lie, at the time I was scared shitless and truly wanted to murder my recruiter in equal measures.

What did you do as a soldier? 

I initially enlisted as a Psychological Operations specialist and eventually commissioned as a Medical Service Corps officer because I thought it would be good for my civilian career. I held a number of different positions, all in the Reserves, but the PSYOP teams were the only place I really felt at home – probably because they were full of punk rock listening, fantasy sci-fi reading weirdos like me. Shouts out to Rob Bell, Chris Curran and Dom Pileri – who have all had more interesting careers than me and are all in some way responsible for anything good that I have accomplished so far.

What was the best lesson you learned in the Army? 

The importance of discipline, teamwork, being on time, and knowing where the fuck you are. 

What was your favorite part? 

Being part of a tribe – you don’t get that in the corporate world, which really sucks. Also, some Ranger Instructor is probably going to kill me for giving away the secret, but the omelet station at Camp Merrill DFAC (where we drilled) serves the best omelet I have ever tasted. 

What was your least favorite part? 

Easy. Drill and ceremony and/or anything involving the words: “review”, “inventory”, “inspect” or “annual briefings”. Please someone freaking shoot me.

So you went back to college. What was your path to law school? 

I got a Business Degree at Georgia State University and then my buddy Chris talked me into law school. We were on the same PSYOP team in the reserves and both needed one more year to finish our ROTC commissions, which we only started because our unit did not have money for Airborne school and ROTC did.  I didn’t even know that the law degree was called a juris doctor when I started. I thought I was going to drop out after the first year. It turned out, much to my own surprise, I was actually good at it. Chris went on to do all kinds of cool shit in SOCOM and is now an Assistant US Attorney. 

What was your greatest lesson from the law school experience? 

You don’t know what you are capable of until you try; and sometimes you need someone else to recognize that potential and push you past your comfort zone. Be open to it.

What was the best part of law school, aside from meeting me? 

Graduation and then paying off my student loans. I also met my wife on a study abroad in law school when we were studying European Union law in Brussels, Belgium. She is probably going to read this, so I definitely need to highlight that as a best moment as well.

What three things would you tell prospective law students now? 

I think this advice probably applies to a number of areas in life: 

One, take ownership of your career – if you do well in law school the structure wants to track you into big law, then put you on a team that has an opening. To beat this gravitational pull or steer into it correctly, you need to have an idea in advance of what area of law you want to practice. The only way to realistically do this is to intern or interview people that are practicing in those areas to see what their day to day lives are like and determine if that is what you want to do with your life. A lot of folks, myself included, start with an end state in mind like, “I want to make Wall Street money and do big deals” but they don’t do a ton of due diligence on what it is like to make the sausage. Do the diligence. Figure it out in advance, and make sure it is going to make you happy. Then take the plunge with confidence. Feel free to contact me. I will help you out or if it is not an area I practice in I will hook you up with someone that can.

Two, minimize debt. Go to the school that has the best ROI. There are a number of reasons for this. Law schools are expensive. Most associate salaries are lockstep. So easy math: all things being equal, if you have the same salary and less debt than another associate, then you are making more money than they are. Also, the faster you pay off that debt, the more intellectual freedom you have. Trust me – at some point in your legal career you will decide it sucks. Better not to have an anchor of debt tying you to it. 

Three, relationships matter. Pay attention to the people you meet along the way. Law school is going to push you to be competitive. The first year is notoriously competitive as a result of the straight curve. Further, the practice of law is endemically adversarial. As a result, junior attorneys and law students underestimate the importance of relationships both for their careers and in creating a sustainable lifestyle.  

Four, have fun. Shit gets real after you graduate. 

Lawyers are not known for being particularly physically fit, or even physical, how do you maintain your fitness level in a time compressed, high pressure environment?

I run and lift religiously. I generally run four days a week and lift three. I have always been engaged in some type of sports, but it was not until the Army that I found running/cardio. Now I love running in the woods with a group of friends. I think that is something coded in our DNA that harkens back to hunter/gatherer times.

How did you get into weight training? 

I was pretty small when I was a teenager. I was also a gymnast, which made you suspect in the South. My dad wanted me to get bigger so I would be a harder target for bullies, so he bought me a stack of Weider weights from Sears and conditioned my allowance on lifting weights three times a week. I started then and never stopped. Too bad I can’t get paid to lift weights now.

How did you get into ultramarathoning? 

Peer pressure. Plain and simple. The Army got me into road running. You introduced me to trail running when we were in law school. About 12 years ago, one of my buddies from work talked me into signing up for the Pike’s Peak Half Marathon – which almost killed me. It starts at Manitou Springs and ends on the summit of Pike’s. I am pretty sure I was DFL. Some dude celebrating his 70th birthday clocked me by at least 45 minutes. I could hear the announcement that he had finished when I broke tree-line at Barr Camp. But the scenery and camaraderie hooked me. I was recovering with a large beer at a local bar afterwards and some folks suggested that if I liked Pike’s I should try running Rim to Rim on the Grand Canyon, so I knocked that out the next year. I don’t know what it is, but there is always a runner at the post-race party suggesting another race or run, and the miles keep piling up. 

How do you train for ultras? 

I am pretty unstructured about it – I am also a mid-packer. Due to the weightlifting I tend to carry more weight/size than your typical ultrarunner. So don’t follow my example if you want to podium. Success for me is to finish feeling relatively good. With that in mind, during the week I like to get two runs of 6-8 miles. Then on the weekend I go long. If I am training for a hundred, I will do back to back long runs (17-30 miles each) on Saturday and Sunday, and walk on the off days. I will also sign up for interim races on the path to the hundo. I hate hourly races but I think they are good training tools and allow you to test out new gear and nutrition.


What has been your toughest race? 

Each race has its own challenges. Once you go above a 50K it has been my experience that something is definitely going to go wrong, and it is a question of what it is, how badly the wheels come off, and how you deal with it.  This was the case the first time I went above 50K at the Pine Mountain 40 miler, which in actuality is a 46-mile race. First and foremost, my nutrition plan of a burger and 4 beers the night before the race was not one of my strongest choices. But what really got me was the chafing. It was so bad that I had to cut the lining out of my shorts at mile 19 (luckily an aid station worker had a knife, because I was contemplating using the battery spring in my headlamp). Then to make matters worse, around mile 35 really bad cramping set in. At 40 I could no longer run and had to walk/limp the last 6. I finished but could not shower without Vaseline for 3 days.  Definitely a low point.

What has been your favorite race? 

The Gorge Waterfall 50k in the Columbia River Gorge outside Portland is EPIC! It’s like running through Jurassic park. It culminates with running up and over Multnomah Falls. The scenery is absolutely mind blowing. If you are going to do one 50K this is the one. Recently I have been getting more into running in a non-race environment. Without the pressure of a stopwatch, you can take things slow and enjoy. As an added bonus, there are no lines for the latrines at the start. The year before last we did a circumnavigation of the Wonderland Trail around Mt. Rainer.  It is 97 miles and 27,000 feet of vertical gain. We split it into 3 days, covering around 33 miles a day. There is a ton of water and the trail is well marked, so you can run pretty light with just a sawyer filter (love these filters) and sandwiches (that’s right! Sandwiches, not gels or gu). My wife agreed to shuttle our gear between campsites, so we were able to eat like kings. This trail is not to be missed. 

Moving beyond law school to your profession, how did you arrive at Mergers and Acquisitions? 

It was serendipity. There was a need on the M&A team at the first firm I worked for, King & Spalding, and I somehow talked them into hiring me. I subsequently joined Equifax, America’s favorite company after Facebook, as their M&A counsel, where I got the opportunity to do a ton of deals in Latin America and India, which was an awesome experience. I currently lead the M&A team at FisherBroyles, which is a virtual law firm with around 250 attorneys all over the United States, so I get to work from home in a t-shirt and shorts. They don’t care that I have sleeves of tattoos and generally look nothing like a stereotypical corporate lawyer. 

What do you like about it? 

M&A is awesome in that it allows for a ton of creativity in structuring deals due to the law’s public policy in favor of “freedom of contract”. Did I mention working from a home in a t-shirt and shorts?

What do you dislike about it? 

The hours can be brutal. M&A tends to be a sine waive. If you are on, you are 110% on. Most deals tend to involve large enough numbers that clients want things done as expeditiously as possible. This translates into cancelled vacations and all-nighters for the teams doing the deals. When you are off, you are hoping another deal comes in and trying not to freak out. My lowest point in practicing law was definitely as a second-year associate when I had to leave my buddies wedding in Alabama, which I was in, during the rehearsal dinner (sorry Max), drive back to Atlanta and pull an all-nighter to get a purchase agreement out Saturday morning. I also had my first five anniversary dinners at the office (sorry Jen). Embrace the suck.

What do you think has been the secret to your success in the law? 

There are a ton of attorneys that have been more successful than me. That said, I think any success that I have had is a function of a problem-solving approach, a fire and forget mentality (i.e. taking complete ownership of projects), and a craftmanship ethos. The work needs to meet my personal standards, which tend to be higher than the clients, regardless of how large or small. Anything worth doing is worth doing right. I believe you are only as good as the points you put on the board on any given day. I don’t keep any of my degrees or awards on my office wall. I want to always be hungry, to make every single day a “good day”. I continuously improve my fighting position. 

What is your next adventure? 

My favorite question. Always forward. I have the Yeti 100 miler in September which I am super stoked about. Then I am focused on the Tuscobia Winter Ultra in December.  You have to pull a sled for 80 miles for this one in arctic temperatures, so it is totally outside my comfort zone and whether or not I toe the line will largely be depend on my ability to get to Wisconsin and train enough to feel comfortable in the temps. I have also started long range shooting, so I am considering making a run at the Mammoth Sniper Challenge Tough Man in January. I just finished the build on my 6.5 Creedmor but need to seriously work on my marksmanship under time pressure before realistically considering doing it. I have been the one old school guy shooting .308 at the PRS matches this year and the wind has been killing me. Or maybe I just suck.  I guess I can’t blame it on the gun anymore. 

What have I not asked that I should? 

What is on my record player right now. Answer? Mastodon “One More Round the Sun”.

Any parting shots? 

Seriously, if anyone reading this is entertaining thoughts of law school, is currently in law school contemplating career choices, is a lawyer in a career malaise, or just wants to shoot the shit, please feel free to reach out to discuss, plan, commiserate etc. You can email me or call/text at (404) 513-7511. I am just a normal dude trying to make a living who fucks shit up as much as everybody else – if not more so.