Brad Feld

Category: Running

I finished marathon #25 today and checked South Dakota off the list. I ran it with ten friends (nine of us did the marathon, two did the half) who were all part of my Chorus team that I started in June.

While this was one of the most enjoyable marathon weekends that I’ve had, it was a rough marathon for me. I finished it in a personal worst of 5:58:26 (gun time right at 6:00:00 – the clock said 5:59:59, but the website says 6:00:00.)

Things went wrong almost from the beginning. The weather was in the low 30s so I couldn’t decide whether to wear pants or just run in shorts. I was hot in the first mile and my stomach was rumbling. At mile three, we looped back around to the start so I went into the Crazy Horse Visitor Center, took my pants off, and took a five-minute bathroom break to make sure I was empty. The Visitor Center was warm, so when I went outside to start running again I immediately stiffened up. At least my gut felt better.

I caught up with my friend Mahendra (co-author with me of Startup Boards). I had planned to run the race alone, but I settled into a nice pace with him as we comfortably cruised through a long downhill section (that we knew we’d have to turn around and come back up later, but well – that was later.)

Around mile 8 I had a sharp pain in my left calf. I never get cramps, so this startled me and I limped on it for fifteen or so seconds. When I realized that it was seizing up, I stopped to stretch it out, but the damage was done. I didn’t have a pain free step on my left leg for the rest of the marathon.

Mahendra was awesome. Instead of going ahead, he waited with me for a minute while the cramp subsided. We walked for a few minutes until I felt like I could run again. We then ran side by side for the remaining 18 miles. A marathon typically gets difficult for me between mile 15 and 20. Today’s was hard for the last 18 miles. That’s a long way to be uncomfortable.

The downhill segment went from mile 4 to mile 10, where there was a turnaround point. Amy was at the turnaround and as she saw me coming she asked if I was ok. Apparently, my gait was off enough that it was noticeable.

For a moment, I thought about calling it quits. I’ve finished every marathon I’ve started and given the Chorus team activity, I quickly got over my doubt about staying on the course. Mahendra (standing to the right of me) and I said goodbye to Amy and started back uphill.

After seven miles, we crested the hill. By mile 17 we were both pretty done and were just shuffling through each mile. The course was extremely well crewed, which was great, but the snow started around mile 17 and by the end we were cold, wet, and mildly manic. When we turned the last corner and saw 5:59:00 on the clock, I told Mahendra to get moving since I didn’t want the clock to hit 6:00 (even though we had 90 seconds or so banked from the start.) We crossed the line right at 5:59:59.

The amazing thing was the performance of Team Chorus in this race. The marathon winner, Jason Burke, was on our team, as were #5 (Winter Mead) and #6 (Gary Ditsch – my coach). On the women’s side, one of our teammates Lou Anderson came in 14th.

Everyone else turned in impressive times. Ryan Martens finished (his first marathon!) in 4:14:37 (with Lou). Christina Sollenberger also finished her first marathon in 4:35:02. And Donna Miller finished her first marathon in 5:04:52. Bryan Oki finished his first half marathon in 2:00:02 and Davis Godbout got his first half marathon done in in 1:47:11.

As we had a post-race meal and told race stories, we all agreed how much Chorus had helped us on both our training and motivating us for the race. I have some new friends for life. While not a great marathon for me, it was a great weekend.

And Amy – you are the most awesome marathon sherpa ever!


I’m running my 25th marathon in South Dakota on 10/8/17. My training has been going well and I’m now in a zone of 30+ miles a week with a long run once a week in the high teens.

Today’s run from Aspen to Basalt was the best run I’ve had in over a year.

Just under a year ago, I did this same run in 4 hours. So, I’m in significantly better shape, which makes me happy since my October 2016 Marathon in Portland, Oregon was a debacle.

A three and a half hour run gives my brain plenty of roaming around time. I like to run naked (no headphones, no music) so the thoughts just drift around. My friend Matt Bencke was in my head a lot on this run. Houston and Hurricane Harvey floated around. The red mountains that I was surrounded by frequently caught my attention. I said hello to a bunch of cyclists and a few horses. Random company stuff made its way to the surface. I noticed lots of crawling bugs and scurrying animals. A bunch of jets flew overhead delivering people to Aspen for the weekend. I thought of Amy a lot.

On a run like this, I need more than two water bottles. I’ve been trying different running backpacks and finally found one I like – the Nathan VaporAir Race Vest. Yup – I’ve got a pile of others (from Camelback, Osprey, and Patagonia) all collecting dust in various closets. The Nathan VaporAir is a keeper.

In the photo above you can see Amy, in her Range Rover, waiting patiently for me at the end of my run (just after the bridge that crosses over 82.) She’s an amazing sherpa for my running, always bringing me a clean shirt, stuff to eat and drink, and transportation back to wherever I started. We went and got a pizza at New York Pizza in El Jebel before heading home. We’re on the couch watching Nadal vs. Mayer, Amy is knitting, and I’m typing.

Today is a day to treasure. Just like all of them, no matter what is going on.


I’m going to run my next marathon in October. I haven’t chosen it yet, but I’m getting close to deciding which one I want to do. And – I’m looking for some help on my training.

Early this year, we invested in Dick Costolo’s new company, Chorus. Some of you know Dick from Twitter, where he was CEO for four years. But you may not remember that before he was at Twitter, he was at Google, and before that, he was the CEO / co-founder of Feedburner, where we were one of the investors and I was on the board.

I loved working with Dick at Feedburner. When he joined Twitter as COO (and then CEO), I was happy for Twitter but sad that I didn’t get to work with him on a regular basis. If you are connecting the dots, you’ll remember that Twitter bought Gnip, where Chris Moody was CEO. Moody worked for Dick for a year before Dick left Twitter and now Moody and Dick get to work again since Moody has joined Foundry Group.

It’s a delightfully small world.

But – back to the help I’m looking for. I’m interested in having up to 24 people join my marathon team on Chorus. If you are a regular runner who is game to get on a training plan with a goal of running a marathon in October, you qualify. You’ll get to be an early pre-beta Chorus user (it’s somewhere between alpha and beta right now), give feedback on it, and be part of my next marathon gang. Oh, and you need to have an iPhone, as it’s iOS only for now.

If you are interested in being part of my Chorus Marathon Team, email me.


I can now check Oregon off the “marathon in every state list.” After a four year hiatus, I ran marathon #24 in Portland today. My official time was 5:38 but there are some caveats that bring it down almost 20 minutes (to around 5:20). More on that in a bit.

Once again I ran it with my running buddy Matt Shobe. This is the fourth marathon we’ve done together (Portland, Detroit, St. Louis, and Huntsville). Matt is much faster than me but he patiently jogs alongside me, tells me jokes, and asks me to do a systems check about every other mile. This time he had to take a dump around mile three that added five minutes to our time. We also each had three other bathroom breaks, which added another five minutes. We’ve decided that eating Pho the night before is not the right food strategy for a marathon.

There were a few things about the marathon that were great. The volunteers and staff were awesome. This is the 45th year for this marathon and Portland shows up to take care of the runners. We stayed in the Hilton a few minutes from the start and finish – that was nice. And the marathon started at 7am which means I’m now on a plane heading home so I can spend the evening with Amy in Boulder.

Other than that, the marathon sucked. The weather was awful – it rained the entire time. Matt and I bought some MontBell shells the day before so our upper bodies were sort of dry. My iPhone, which is carried in my fanny pack is busted and Matt’s Nexus is as well. I have a few blisters on my toes, which never happens, and is a result of 27 miles in soggy shoes. Both of our fingers were numb and waterlogged by the end. And there were long stretches of the course that were just dark, wet, and soul sucking.

Normally a marathon is 26.2 miles. But this one was 27.

We didn’t ever see the mile marker for mile 1. When we eventually saw the mile marker for mile 2, our watches said 2.5 miles. When I crossed the finish line, my watch said 27.02 miles. This fucked up my running strategy way more than I expected as I spent miles 3 to 7 obsessing about the extra distance. My plan was to walk through the water stations but they weren’t consistently spaced so at some point I had no sense of what my run:walk pattern was. This contributed to us going out to fast, which was probably the most painful part of the race, which was completely self inflicted.

Other than the bathroom breaks, we were either at or below 11 minute miles for the first 11 miles. We drifted up to 12 minute miles for the next few and the I completely hit the wall at mile 16. A string of very slow miles – times I’d typically see in the last few miles – started. 13:42, 12:36,13:54, 14:53, 14:36, 13:36, 14:52, …

At mile 18, I told Matt to just go ahead and we’d meet up at the end. He said “no fucking way – I have one mission today and that’s to get you across the finish line.” I love him.

At the system check around 20, I finally figured out how to describe how I was feeling. “Globally great, locally shitty.” We chucked a bit and I said “all my global variables are in an acceptable range but my local variables are completely screwed up.”

We crossed the 26.2 mark at 5:27 on my watch. This wasn’t my PW (personal worst) – that’s 5:47 – but it was close. If you subtract the bathroom time, It’s a little under 5:20, which is still slow for me (I’m usually in the 4:45 – 5:10 range with an occasional 4:30.

It was an incredible relief to cross the finish line. I was done. We hugged, walked to the hotel, took showers, had a beer, ate some food that wasn’t Gu, pretzels, or gummy bears, and then headed home.


I spent the day yesterday with Seth, Ryan, and Jason at our quarterly offsite. We finished, as is our tradition, with dinner at Frasca, which involved a lot of wine. I rarely drink wine anymore as I never feel good the next day (I’ve switched to mostly drinking scotch.) But Frasca is a special place and the wine choices I end up with when I’m with my partners are spectacular.

I’m running enough now (around five hours a week) to be in a disciplined routine where I follow what my coach Gary gives me each week. When I went to bed last night, I knew I’d have a hangover in the morning and it’d be tough getting out the door. I had a one hour run – a typical Tuesday run for me after a long run on Sunday – that’s a combination of recovery and gearing up for whatever is really coming at me this week.

I was not surprised that when I woke up at a few minutes before 7am I felt like shit. It wasn’t the “I have a cold” feeling, but “Wow – I drank too much last night” feeling. I drank about a liter of water,went to the bathroom, brushed my teeth, put my running clothes on, and Facetimed Amy. I had a fantasy that when I got off the line with Amy I’d feel better, but I knew it was a fantasy.

As I got out the door to start my run, I decided to punish myself today. I knew that I wouldn’t have any speed in me, so instead I took a right on the Boulder Creek Path and headed to Eben Fine Park. I knew that I’d be going uphill on a steady grade once I got to the park and by that point I’d feel completely crappy as the hangover started to burn out of my system. I also knew it would be worth it, as by the time I hit the 30 minute mark and turned around, I’d feel good.

And I did. I glided down the hill back toward home, hangover gone, legs moving, and sweat flowing. I let my thoughts go wherever they wanted to, and as some point I thought “Ok – I’m at a new level and ready to start thinking about a marathon again.” The breakthrough was that I got out there and did a real run even though it would have been easy to roll over in bed, moan, and go back to sleep at 6:50.

If you are a runner, I expect you know this feeling. It’s the redemption after a night of excess, followed by the joy of the next day when your system is recalibrated.

The sun is out, it feels like summer, and life is good.


I’m a solo runner. While I regularly get asked to go on runs with other people, I almost always decline, as one of my great joys is to run alone.

There is one exception – I love to run with CEOs and founders of companies. There are some great stories about the outcomes from these, like my runs with TA McCann that resulted in our investment in Gist. I’ve run marathons with TA, Matt Blumberg (Return Path CEO), Matt Shobe (FeedBurner co-founder), Herb Morreale, and a bunch of people including my partners Jason and Ryan.

My favorites runs are the impromtu ones with CEOs like the one I did last night with Matthew Bellows (Yesware CEO). Earlier this week, Matthew sent me a note to see if I wanted to go for a run just before a dinner we were having together with Bart Lorang (FullContact CEO). My running goal this week is “three runs of any duration” and by Tuesday I knew the dates were going Thursday, Saturday, and Sunday. So I said yes and we scheduled it at 5pm – after my last meeting, but just before dinner at 6pm.

We met at my office at 5pm. The sun has gone down in Boulder by then at this time of year, but Matthew looked ready to go in his red running jacket and sweatpants. We walked down the stairs to Walnut and were blasted with a gust of cold wind. We headed up the Boulder Creek Path leading up to Canyon and out of town, straight into the cold wind.

We talked non-stop. He had a few things on his mind and I gave him feedback. As the minutes unfolded, I noticed I was doing a lot more talking as I told a few stories to underline my points, but it could have been that he was enjoying just plodding along at my slow pace, enjoying the run.

At the turn around point where the Creek Path starts really heading up the canyon, we stopped for a moment and looked around. Matthew has spent a lot of time in Boulder, including a two year period earlier in his life, and he emits the glow of someone who was touched by living here and always loves to be back.

The trip downhill with the wind at our backs felt a lot faster and before we knew it, we were back at my office. Matthew was going to head back to the hotel, shower, and change but I reminded him we were in Boulder so instead we just walked over to Bramble & Hare and hard dinner with Bart, which was awesome at many levels.

Matthew – thanks for another great CEO run!