[This article is part of a series in which I’m sharing my Startup Lessons Learned from a 100-mile ultramarathon I completed in Bryce Canyon, UT.
In my life as a runner, a sales coach and an entrepreneur, I continuously see parallels and lessons that I feel are important to share with you, the startup CEO, the entrepreneur, the doer of hard things.
Over the next couple of weeks, I’ll share my lessons learned in these posts and on The Startup Selling Podcast.
Much like running an ultra-marathon, the journey as an entrepreneur building a company is long and difficult. As I’ve heard Tom Bilyeu, co-founder of Quest Nutrition, say – the struggle is guaranteed but success is not. It takes tremendous effort, dedication and fortitude to keep going in the face of obstacles and challenges.
Please share these posts with a friend or colleague whom you think might benefit from my lessons learned on the trail. Thank you for reading.]
Whether you’re running a startup or an ultramarathon, even when you know what’s ahead, it’s still much tougher than you think.
When running a startup, most of us do all of the research and preparation we can – both before starting the company and certainly as we’re operating the business – examining industry trends, market conditions, competitors and customer needs, and learning from every interaction with the market, investors, advisors and prospective customers.
Even with the best intelligence, even when we think we know exactly what’s ahead, no amount of preparation, research and due diligence tells us everything we need to know or prepares us for the “hard” that’s ahead.
On the trail, race organizers post a map and elevation profile of the course, and with a little research, you can find race reports from previous years’ races that share details about the course and the trail. A pre-race briefing with the race organizer the night before the race start gives runners a chance to ask any questions they have about the course, logistics and what to expect out there.
Parts of the course that look easy can end up becoming much more difficult than you think. On paper, the downhill sections might look like a place to pick up time after long slow climbs, but the trail might be rocky or sandy or steep. I ran a trail marathon on Mt. Diablo where the downhill trails were so steep I had to walk sideways, back and forth across the trail and eventually slide my backside to get down the mountain. At the Zion 100 last year, a downhill section ran along at the edge of a cliff with a 1000’ drop-off to the right (photo above) – not exactly a place you want to risk tripping on a rock to save a couple minutes. At the Mt. Hood 50 in July, I face-planted 13 times, tripping on roots that littered the trail, finishing the race with shredded knees and palms.
As part of my race prep, I start watching the local weather a week ahead of race day to see what gear I’ll need. Bryce Canyon sits on the Colorado Plateau in a desert climate. Because the elevation ranges from 7000-9000 feet, the weather can change quickly from day-to-day and hour-to-hour. Two years ago, the daytime temperatures reached record highs – stretching into the low 90s. This year, the weather forecast called for highs in the 40s and lows below freezing with rain and snow expected throughout the day and night.
Even with all of that information, you never really know what the course will be like until you’re out there. You never know how steep or challenging the climbs really are. You don’t know how cold 28 degrees will feel at night in the desert when the wind is blowing and snow is coming down.
I remember at Blend with one of our early deployments, the engineering team spent weeks fine-tuning and QA testing our workflow software before we launched with the customer. We had it nailed and were ready to knock their socks off with the latest and greatest mortgage workflow software.
When we asked the onsite users to login, they opened up a version of Internet Explorer that Microsoft had stopped supporting a year before. WTF?
No problem. We’ll just have them upgrade to a newer version or install Chrome.
The IT team told us – “Those browsers are not approved as part of our IT policy. Users are required to use the browser currently installed on their machines.”
Weeks of QA testing down the tubes, and now the team had to recode the platform to work in a deprecated version of IE.
Deploying with this first customer site also meant working through their legal and procurement departments. Keep in mind… this was 2014. The whole “move to the cloud” thing was considered new and scary for many banks and lenders out there.
After six months of navigating the procurement and risk management gauntlet, we passed our SOC-2 audit and had our ISO-27001 certification. We were ready for anything.
Until it came to our deployment when a quick and relatively easy sale to the business team led us to a meeting with their CTO. I’m not a technical person, but even to me, it seemed like many of the questions we had to cover in an hour-long meeting seem elementary. As we walked out of the building, I said to our risk officer, “I don’t think they’ve bought too many cloud-based products before.”
He said, “They haven’t bought any. We’re the first.”
“How do you know?” I asked.
“Because of the questions he asked. If this bank had ever bought any SaaS or cloud-based software, he wouldn’t have asked 90 percent of the questions he just asked.”
Jeez. Here we go again. Even when you think you know what to expect, you just don’t know what you don’t know.
The Bryce Canyon race was a two-loop course – a 50.6-mile course completed twice.
The good news with a looped course is that you know what to expect the second time around.
The bad news with a looped course is that you know what to expect the second time around.
By mile 43, just a few miles from the starting area to refuel and reset for the second lap, the voices started creeping into my head – “Are you sure you want to do this again? It’s going to be cold out there. You could just call it a day after 50 miles, eat a good dinner and crawl into the RV and sleep.”
We all hear these voices, probably more than we’d like to admit. Once you’re on your journey, once you’ve gotten your product to market, once you’ve gotten your first customers and revenue, once you’ve started building your sales team – you know what you have to do, you know what’s ahead for your startup, and we all ask ourselves – “Why exactly am I doing this? Is it worth it? Do I really want to keep going? I could just go back to that easy corporate job with the office and health insurance…”
<-- My iPhone reminded me
it was time for bed. Ha!
Still more than 14 hours
to go...
On the second loop, I reached the mile 75 aid station at 1:30am. During the previous stretch of trail, I had nodded off three times while walking. Yes – I actually fell asleep while I was moving. In the heated aid station tent, I knew what was ahead for the last 25 miles – an eight-mile section with endless up-and-down switchbacks, followed by a five-mile loop with continuous climbing, followed by ten more miles of climbing before the last three downhill miles to the finish. I was still 9-10 hours from the finish.
Later, somewhere between mile 83 and 88, I stopped on the trail and laid on the ground with my arms outstretched, staring at the moon, waiting for the first glimpse of sunrise, wondering how the heck I was going to finish this race. I knew this section still had more climbing ahead before the next aid station. I’d been out there for nearly 24 hours, running from before dawn yesterday, to dusk, then through the night without sleeping. I was spent. The last fifteen miles to the finish might as well have been another 85.
The fact that I knew what was ahead – the course, the trail, the elevation, the hours – made it even more difficult.
Sound familiar?
The parade of investor meetings. The afternoons stacked with interviews to find your sales VP and two more engineers that you needed to hire six months ago.
That three-week stretch of travel, crisscrossing the country from the Big Industry Conference to the customer meetings in Chicago and New York, then back to the office for two days before heading to LA for a meeting with a strategic partner.
You know what’s ahead, and that’s what makes it hard.
Yet somehow, someway, you pull yourself off the ground every morning and keep moving forward every day, every week, every month because it’s the only way you’ll make progress on your startup’s journey.
That’s the only way to reach your finish line.
Go Farther.
Missed the Event? View the recording here
Webinar Recording 2022
Become an Insider! Gain access to videos, articles and more.
By submitting this form you are agreeing to receive email from us.
We hate spam as much as you do, and promise not to share your email address and we’ll keep it safe.
