Startup Management Lessons Inspired by Japan’s 100 Famous Mountains, Part 6: Learn from Failures and Continue to Grow
At D-POPS GROUP, our corporate mission is to multiply the number of growth companies (so-called “unicorn companies”) that will revolutionize society, and our core value is to grow and learn together through sincerity, humility, and gratitude.
Ever since setting his goal last summer to “conquer all of Japan’s 100 Famous Mountains while wearing our company’s iconic unicorn T-shirt”, Genta Sugihara, an advisor to our company, has continued climbing mountains across the country, reaching 62 summits as of writing this article. In this series, he reflects on the successes, failures, decisions, and lessons from his journey, drawing parallels to startup management and organizational leadership.
Because he started with relatively easy mountains, only the most rugged peaks remain after the first 50 or so. Over the past year, by thinking back on every climb, learning from his mistakes, and repeatedly training, he has gradually raised the level of mountains he can climb. If he had attempted the mountains he is climbing now right from the start, he would have lacked the stamina and technique, and likely would have had to turn back or suffered a major injury.
Basking in the afterglow of reaching a summit is wonderful, of course, but it is incredibly important to properly review after every single climb and apply those lessons to the next challenge. Just as merely accumulating mountain climbing experience doesn’t automatically improve your climbing skills, in business, simply racking up years of experience does not guarantee significant growth.
In Part 6, we will explore how identifying failures, learning from them, and connecting them to your next steps is the true wellspring of growth.
16. Review After Every Single Climb: Learning from Failure is More Important Than Not Failing
After every climb—including mountains outside the 100 Famous Mountains—I have kept records using a hiking app (in my case, an app called YAMAP).
Initially, my goal was simply to check my GPS track or look back at the photos I took alongside my memories. However, as I continued my 100 Famous Mountains challenge, I have also begun using it as a way of looking back.
Specifically, I will record the number of times I stumbled, slipped, twisted an ankle, or fell. I note what I ate for trail snacks and lunch, the shoes I wore, my foot fatigue, and the state of any blisters. I also log my overall physical condition for the day.
On a mountain trail, especially on steep slopes or rocky terrain, falls can directly lead to fatal sliding accidents, so they must be avoided at all costs. And stumbling, slipping, or twisting an ankle are the triggers that lead to those falls—and consequently, sprains, bruises, or major injuries.
I memorize how many times I lost my footing one day, or if I slipped on a tree root, fell on my backside, etc. Then, to avoid repeating the same mistakes, I search for the root causes. I think about what I need to pay attention to next time. I realized that doing this is the best preventative measure against accidents.
During the first half of my challenge, I suffered from toe blisters, internal bleeding under my toenails, and thigh muscle cramps multiple times. I even sprained my shoulder when I reached out my hand to break a forward fall. By learning my patterns of stumbling and slipping, tracking my food and water intake to find the causes of my cramps, and devising countermeasures for each issue, I was able to gradually reduce these troubles.
(Every journal entry always includes a review of the day’s climb.)
Before starting the 100 Famous Mountains challenge, I was a complete amateur. But through these reviews, I identified countless failures and learned a great deal from them.
I’ve learned things like:
・Ankle twists are common when descending rocky terrain, so pay extra attention・Bare tree roots are incredibly slippery when wet・On long hikes, replenish calories frequently before actually starting to feel hungry・Frequent hydration and sodium intake are highly effective in preventing cramps・Tape specific parts of feet and legs to prevent sprains, knee pain, and blisters・The quality of sleep the night before a climb drastically affects fatigue levels
You might think those are all just standard mountaineering principles and common sense. However, the important thing is that I learned these lessons through hands-on experience in the field.
The exact same thing can be said in the business world.
When a project is completed, or after executing a business alliance or corporate acquisition, it is absolutely essential to conduct a proper review after the fact—either immediately afterward, or after a certain period when results can be evaluated. What went well? What didn’t? What were the root causes? What should you do differently when facing a similar situation in the future? You must verbalize these things.
You can learn the theories of entrepreneurship, business development, and sales in MBA classes or business textbooks. However, knowing something and actually being able to do it are two different things. You will also quickly realize that in the real world, many theories do not work exactly as written.
That is why the attitude of learning from when something fails in practice is indispensable for startup companies.
Instead of choosing the safe path just to avoid failure, you must challenge yourself without fear of failing, and elevate your experience level through review. In both mountaineering and business, what matters is not avoiding failure, but what you learn from it and how you apply it next. In other words, the key is not letting an experience remain merely something you went through, but transforming it into actionable insight.
Now, people do not necessarily grow just by experiencing things. Only when you think back on an experience, verbalize the causes of your failures, and change your subsequent actions does that experience transform into true learning.
17. Prepare Behind the Scenes in Order to Perform When it Matters
My goal to “Summit Japan’s 100 Famous Mountains by around 60 years old” means that I’m starting the mission at age 58 and finishing all 100 peaks in three to four years. This presents a different kind of difficulty than a challenge undertaken by a tireless youth.
This is because at my age, muscle strength naturally begins to decline, joints become stiffer, and it takes longer to recover from fatigue.
As I continue pursuing my goal, in addition to the review I mentioned in Chapter 16, I’ve started to intentionally train my body when I’m not actively climbing.
This includes thorough stretching routines I previously disliked, especially loosening up my lower body joints. It means doing a strength regimen that leverages my upper body strength for climbing. It also means cutting back on alcohol and prioritizing high-quality sleep.
Furthermore, I now hold conversations with AI as a sounding board to analyze the type of trail and choose the optimal hiking boots for my next climb; determine the transportation method to the trailhead, departure times, and lodging locations according to my predicted level of fatigue; and I decide the amount of water, trail snacks, meal contents, and the number of rest stops.
(Deciding on gear and equipment in advance based on different trail types)
By continuously training and researching on a daily basis like this, I have been able to compensate for the handicaps of my age and continue with my goal, while gradually ramping up to highly difficult mountains.
In the same way, it is vital for business managers to continually refine themselves behind the scenes.
However, there is one difference from mountaineering. When climbing a mountain, being older can be a handicap in some ways. On the other hand, for entrepreneurs and business leaders, being young and inexperienced can be a handicap. Even with boundless passion, a lack of industry network, low credibility, and not having experience can often become a hurdle.
That is exactly why it is so important to keep learning daily to compensate for those shortages.
Even in the midst of a busy schedule, it is crucial to maintain an attitude of learning the wisdom of those who came before you, such as by asking veteran executives to be your mentors. You must also not neglect studying, whether that means researching case studies of successes and failures in your business domain, or deeply analyzing similar or competing companies based on public information.
What is especially important is not waiting to learn until a problem occurs, but continuously learning behind the scenes.
You cannot start building muscle after you encounter a difficult rock wall on the mountain. It is too late to study map reading after you get lost. Similarly, in business, if you start studying finance only after falling into a cash crunch, learning organizational HR theory only after your team starts falling apart, or researching competitive strategy only after a fierce rival appears, it might be too late.
By gaining a broad range of knowledge on a daily basis, looking at the successes and failures of other companies, and thinking about what decisions you would make in their shoes, this steady accumulation of learning leads to rapid decision-making and a wealth of options when a crisis hits.
Just as the stamina and technique for mountaineering cannot be acquired overnight, professional business judgment isn’t something you can obtain right in the moment you need it.
How much you prepare during the rehearsal determines how well you can perform when it’s time to stand on the stage for the real show.
That is precisely why the more you continue to challenge yourself, the more intentional you must be with the time when you are not actively challenging yourself.
18. Gain Field Experience: Expand Your Playbook to Increase Your Adaptability to the Unknown
Along with the previous sections’ concepts of looking back and preparing behind the scenes, an even more important factor is increasing your experience by actually climbing mountains.
“Mountain legs can only be trained in the mountains.”
This is a common phrase meaning that the leg strength and stamina required for mountaineering cannot be forged through training only on flat ground or in gyms. They are built by actually walking on mountains.
As this phrase suggests, you climb many mountains, reflect on your experiences, make necessary improvements, and climb the next one. Through this cycle, you develop strong legs capable of enduring rugged peaks.
However, physical strength and technique are not the only things you acquire through repetition.
Every mountain is different. Even on the same mountain, the situation changes depending on the weather, the season, and your physical condition. Yet, as you accumulate experience, you gradually become able to make judgment calls the very moment a situation develops. For example, “This rock looks slippery.” “That’s a loose rock.” “This pace is too fast and will hurt me later, let’s slow down.” “Let’s take a rest here to recover.”
This happens because your various past experiences accumulate, allowing you to unconsciously pull from a mental playbook of similar experiences to make decisions, even when encountering a situation for the very first time.
Gaining experience in the field is not simply about increasing the number of things you’ve done. It is about sharpening your ability to handle unknown situations and adding more tools to your toolkit.
(I have yet to climb these peaks, which could be called the most difficult mountains in Japan. *Images taken from YAMAP site.)
It is the same in business.
Particularly for startup companies trying to bring innovation to society in new domains, there are no textbooks with the correct answers to begin with. No matter how much you research in advance or bounce ideas off others, in actual sales activities or negotiations, conversations rarely proceed exactly as you envisioned.
You receive unexpected questions from customers. Conditions are suddenly changed in a critical meeting. A new hire doesn’t perform as expected. A major corporation suddenly enters your domain. The fundraising environment abruptly deteriorates.
When faced with such situations, what ultimately makes the difference is not just textbook knowledge, but the sheer variety of situations you have experienced up to that point and what you have learned from them.
Business leaders and executives with extensive field experience have sharpened their ability to detect changes in their external and internal environments (as described in Part 4), and possess a large collection of tools. Even when facing a problem for the first time, they can check it against past experiences and think: “This is similar to that time”, “This option has these risks”, or “In this phase, we need to verify this point first”.
Of course, gaining experience does not mean you will stop failing. But if you review each experience, learn from it, and change your next action, you can lower the probability of repeating the same mistakes. And the options available to you when facing the unknown will continue to multiply.
People do not grow just by experiencing things. But there are lessons you can only learn by experiencing them. Growth does not mean never failing again. It means expanding your playbook with every new experience, enabling you to make better decisions in your next struggle.
This concludes Part 6 of “Startup Management Lessons Inspired by Japan’s 100 Famous Mountains”.
Recently, while I was coming down a mountain, someone passing me on the other side of the trail called out, “That’s a cool T-shirt!” Also, in the 15th month since beginning this challenge, I hit the milestone of 60 mountains climbed. I know this is entirely thanks to the understanding and support of everyone around me, both at work and at home. Filled with this spirit of gratitude, I’ve acquired the habit of buying local souvenirs from the areas around the 100 Famous Mountains and distributing them at the office when I return.
I will continue to do my best so that one day, this D-POPS GROUP unicorn T-shirt—which has climbed up so many of the 100 Famous Mountains with me—will be well-known in both the startup community and the mountaineering community.
Next time, the topic will be “Sincerity, Humility, and Gratitude”. Facing the mountain with sincerity; challenging nature with humility; feeling gratitude toward the people you meet on the mountain, the people who maintain the trails, and the people around who support you: I believe these attitudes are profoundly important in startup management as well. In the next installment, we will explore the concepts of sincerity, humility, and gratitude reaffirmed through mountaineering.
For those who have not yet read the previous articles in this series, please check them out here:
Part 1: Define Your Summit, then PreparePart 2: Detailed Planning, Steady ExecutionPart 3: Strategy, Tactics, and ExecutionPart 4: Extend Your Antennae, Pay Attention to Your VitalsPart 5: Balancing Tenacity and Caution
D-POPS GROUP Advisor Genta Sugihara
September 2026: Mt. Jonen (#55), Mt. Yakedake (#56), Mt. Iwate (#57), Mt. Hayachine (#58), Mt. Hachimantai (#59); October 2026: Mt. Hiragatake (#60)
