A recap: Is your entrepreneurial business an Ultra Marathon?

Parallels for early stage businesses in endurance sport

photo by iancorless.com, with permission

12th October 2017

This past weekend saw the 2017 edition of Lakes In A Day, a gruelling 50 mile run with 4,500m of technical ascent (and descent) traversing North to South through the Lake District. I was too scared to tackle it this year :-( — a year that saw particularly harsh weather adding even greater challenge. In reverence of the accomplishments of those athletes who ran on Saturday, I thought it opportune to dust off my 2015 recounting of the route, interwoven as it was with the parallels I drew from this race for early stage growth businesses and those seeking early stage finance….

Originally published at https://www.linkedin.com on October 16, 2015

On Saturday 10th October (2015) I competed in, and completed my first ever Ultra Marathon. For a runner whose heritage is rooted firmly in the 10k and half marathon heritage, stepping up to the marathon distance recently has proved hard work. But ultra marathon running is in a different league, particularly when it takes in extreme terrain. It takes strength, patience, willpower, mental fortitude and buckets full of endurance. It struck me during the course of a very, very long day that there are similar learnings for those running high growth companies. So I thought I’d lay out the story of the day, and throw in a few parallels as it relates to the life of an entrepreneur as seen through the lens of Series A VC investor (in italics after the story paragraph).

The event was called “Lakes in a day”. From the safety of a computer screen it looked like a wonderful opportunity to wander lonely as an ultra runner, perhaps floating serenely on fell shoes o’er vale and hill. And together with a crowd of (other mad) people, beside the lakes and beneath the trees, on a path that stretched in never ending line, how could I not be but happy in such a jocund company? Perhaps afterwards I thought, when on my couch I lay, in vacant or in pensive mood, memories might flash upon that inward eye, in the bliss of later solitude. Oh yes, a perfect first taste of ultra marathon running, with apologies to Bill. In reality it was always going to be somewhat less romantic than a Wordsworth masterpiece. Registration having been performed the night before, the race kicked off at 8am from Caldbeck in the Northern Lakes. All around were gnarled and grizzled looking ultra runners, years of experience in their sinewy thighs, athletic achievement screaming from their professionally clad bodies.

And perhaps so it is for the first time entrepreneur, sitting in the VC’s office with his laptop and business plan — from a distance perhaps a romantic experience, the reality terrifying. For the entrepreneur a truly transformational opportunity, for the VC, just another day in the office.

The hefty trek

In typical un-ceremonial Northern style we were given 10 seconds notice of the start, and suddenly the assembled masses, well at least 350 people, were trotting their way down the lane from Caldbeck. Hills in the distance at this point were suitably far away to remain attractive and scenic, the conversation was convivial and I was wondering how this could be at all difficult as we ambled along at a pace that would normally only count as a warm-up shuffle. But I wasn’t in my comfort zone of a nice fast, flat half. This was ultra. These were different beasts assembled in their haglof clothing, their fell shoes and cotton beanies. The walking poles meant business and the funny water bottles adorned with periscope-like straws underlined that this was a different type of challenge.

Raising venture money is in reality very different from the day-to-day activity of an entrepreneur — founders need to be aware of what they are entering into.

It wasn’t long before the fun began and the narrow choked lane full of conversation and low heart rates transitioned into open fell and increasing incline. The long ascent to Blencathra would first be punctuated by a testing little 650m climb, to High Pike descended rapidly of course down a valley of thick , boggy heather to splash across the river Caldew at the bottom. It was only when cresting High Pike that the imposing majesty that is the rocky 900m of Blencathra, could be fully “appreciated”. By this point the field was thinning out and the path had thinned to single file as everyone scrambled up the increasingly scree strewn slope.

Does life immediately get hard for an investee company post VC financing? Hopefully not if you have the right investor, who can help you address the scale of the challenge. The right venture firm (and indeed whether a venture firm at all or other sources of early finance) will depend on the company and the situation.

The real test of Blencathra however was in the descent. Crossing over the aptly named Foule Crag and Tarn Crag, the desperate void that is the Middle Tongue dropped away to the side of an exposed ridge that would have been more suited to a mountaineering competition that an ultra marathon. Exhausted already by well over 1,500m of climbing and with over 2 hours already on the clock, this was the daunting prospect separating runners from their cup of tea at the first pit stop in Threlkeld. It was to be the scene of many slips, countless grazes and numerous hairy moments. Not for the faint hearted this race.

Not your average course

There are challenges for an entrepreneur even where it seems that the going should be easier, and even where the outlook is wonderful. Networks are important for addressing these un-expected obstacles and VC network can play a strong role in that.

We reached Threlkeld after just over 3 hours, at this point just 30 minutes or so behind the leaders of the field. I foolishly rushed my pit stop, abjectly trying to force down a couple of flapjacks and packets of jelly beans. The next section was 28km of the roughest terrain, reportedly taking 6 hours and I was rather concerned that in my haste I had not collected sufficient water to last the course. The online briefing had been explicit that there were no places, other than the sheep-poo infested Grysdale Tarn at which to fill up before Ambleside. I was later to find plenty who stopped to do so.

Nothing beats being prepared. There is no substitute for having the right metrics and the correct MI frameworks for the business. Don’t rush this otherwise you might be starving your company.

White Pike awaits

It was shortly after Threlkeld, approaching 4 hours on the clock, where the real brutality of this race started to hit home. White Pike is evil. Pure evil. I’m sure Dante wrote about this hill in his Inferno, and I’m sure I caught a glimpse of Judas standing in the stream about half way up. The hill quickly became a cliff, and runners left right and centre slowed to crawl with obvious signs of distress. After the huge pounding my knees had already taken in the unfamiliar territory of descending two aggressive peaks, the familiar ITB on the outside of my left knee was already very sore and it was becoming increasingly difficult to mount the slope with any speed. The demons flooded in, and 3 times I turned round eyeing Threlkeld in the distance and inventing the excuses to admit defeat, to find the welcoming embrace of vehicular transport. In retrospect this seems startlingly early in the race, but I think after this point time simply distorted, and all realism lost. I’m not sure where the temptation was consigned, but I convinced myself that heading down was not an option, that there would be other options for abandonment later if needed.

There will be times when it appears impossible to carry on. It isn’t.

Partial redemption was found nearly an hour after starting to mount the slope at White Peak as the lunar landscape of the high fell came into view and the repeated challenge of consecutive craggy 200m up/downs now presented themselves in the rolling journey to the peak of Helvellyn. By now, 6 hours in, full running was a dream — I could manage only a shuffling kind of motion, all the time attempting to keep my left leg straighter to avoid the lancing pain being delivered by an angrily irritated ITB. The scene reminded me of a heavy drinking night at college — all around me were various similar zombies, moving eratically with glazed eyes and mumbling unintelligible things about Ambleside and cups of tea.

After Helvelyn there was the forced descent down into Grysdale Tarn and the foreboding sight of Fairfield, another vertical zig zagging path that disappeared 900m above like a high rise building. By this time I had paired up with an equally afflicted runner, Nathan, who was actually struggling more than my shredded thighs up the ascents, but lacked the knee impediment on the descents. We were kind of matched across this remote country. Fairfield was the last of the fully serious climbs, and it lead out onto a causeway down into Ambleside, the fabled mid stop of the race which could be seen shimmering in the autumn evening in the distance. But this causeway, whilst beautifully adorned by a long dry stone wall and framed between the setting sun and the distant ripples of lake Windermere, was seemingly part of an MC Escher painting. 30 minutes later after rock climbing down various gorges, and negotiating slate filled scree paths, Ambleside appeared to be no closer. Just a faint tantalizing vision in the distant horizon. But the knee was feeling slightly stronger, perhaps having by now run through the pain and I was able to resume a downhill shuffle, still slightly dragging the left leg as I negotiated the various obstacles.

Partnerships are often crucial to early stage companies — distribution agreements, channel partnerships, even advisor relationships as you prepare the ground for later in the day. The finish may not seem to get any nearer, but the value is building.

A beast of a course profile

Arriving in Ambleside at around 1730 was nothing other than a euphoric experience. I had just seen off the hardest 6 hour period of my running life. Those beasts of hills were behind us, and the throngs of people in Ambleside were all smiling, clapping and giving various plaudits. After 9 ½ hours of “running”, an ultra run already effectively completed, and the most beastly of terrains was behind us. The feet were cutting up in wet, bog smelling socks, the thighs were shredded from repeated extreme ascent/descent and my back was stiff from carrying 2litres of water and a collection of mandatory, yet un-used kit. But the stop was an oasis of pasta and high calorie foods, and 20 minutes later myself and my new companion were on the road once more for the flat(ter) section of the course. We managed to run a good proportion of this third section, finding deep down reserves of strength to ignore the knee pain, and lift the legs despite the absence of serviceable muscle fibre. As night fell the world reduced to a semi circle of head-torch light and the woods and hills pressed in from all sides. Navigating through Far Sawrey onto the shore of lake Windermere in pitch darkness was an interesting experience, and one for which the Garmin 800 unit was a godsend. Yet even in this seemingly straightforward section, the organisers showed their gratuitous nature, sending us up a severely steep incline and back down before the final pit stop in Finisthwaite. With just 12km to go we arrived at this oasis at 2200, 14 hours after setting off from Caldbeck.

Most successful start up company exits are a result of a long hard slog — perhaps harder than anything else in a career. An entrepreneur will need to dig deep in the reserves to counter the myriad competitive, regulatory, resource and financial challenges that are set to hamper progress along the way. If there aren’t challenges, it’s likely the end result isn’t as valuable as you think.

I’m not sure I can bring words to describe the final section of this race. Suffice to say that after a decent, rice-pudding fuelled, break at Finisthwaite it took over 3 hours to negotiate the final 12km back to Cartmel. By this time our party was up to 3 (broken) runners…although the only running that was possible in this entire stretch started at the boundary of Cartmel School….which housed the finish! This 3 hours probed the depths. And it was beautiful to finish. Europhoric. Very emotional.

The world’s most beautiful sign

Hopefully the completion of any long journey will be a happy one.

I think it is very rare to experience an event that truly changes the way you look at a sport. It’s fair to say that I underestimated the challenge of this race by an order of magnitude, and was completely unprepared for the endurance challenge it represented. But having probed the depths of pain and despair within 4 hours of the start, to finish more than 13 hours later was truly an overwhelming experience. Out of 350 people at the start line I finished in 167th place — possibly my worst ever relative placing in a field. But this is without a shadow of a doubt my proudest ever finish.

Good luck to all entrepreneurs who start the amazing journey that is building a business. And good luck to all those who engage in the fantastic sport that is Ultra Marathon running.

More tales of ultra distance sport here.