• The Astral Consulting Group

The Hidden Failures Behind Greatness

Updated: Nov 30, 2020


On March 29, 1982, with seventeen seconds left on the clock, Michael Jordan took a shot in the NCAA Men’s Basketball Championship that long endured as one of the greatest moments in his career. Sinking this shot bumped Chapel Hill over Georgetown with a score of 63-62, and won the Tarheels a national championship.

We’re all familiar with the glory and sentiment of this moment, but there is one uncomfortable question that few actually consider.

What if he missed?

The success stories of our heroes serve as a source of inspiration that guides us through adversity. And while everybody loves a happy ending, it’s often just not realistic.

This week’s founder, JT Haskins of Rogue Ventures, isn’t afraid to ask that uncomfortable question. For him, adversity and failure are the greatest learning lessons of life. Albeit uncomfortable and challenging to overcome, he believes that in entrepreneurship and life, you learn far more from failing than winning.

I asked JT about the day he decided to finally take the leap of faith and start his own company. Before founding Rogue, JT worked in the healthcare arm of a large education management company. He was assigned on an entrepreneurial task that he was enjoying, and which was experiencing continued success. However, it soon became readily apparent that company management wasn’t willing to accommodate the changes necessary to adapt to the rapidly-changing industry, and just “wasn’t moving fast enough”. One day, a call came down the corporate ladder that the firm would not be pursuing several new revenue streams JT and his team had identified as instrumental in remaining competitive in the market. He left the office enraged, and returned home that afternoon seeking support from his wife.

Her sage advice came in two simple yet powerful words.

Just quit.

JT thought critically about what he was truly passionate for in life, discovering a deeper calling for helping budding entrepreneurs. He put in his 2 weeks, and shifted his focus toward building from the ground up. He recalled a conversation years earlier with a friend in the venture capital space, who surmised JT would do well in the industry. Although JT had a deep drive to help entrepreneurs, he saw a discrepancy between the missions of startup founders and VCs. Venture Capital firms are in business to make money, and more often than not that requires stripping control from the founder and replacing them with a more decorated CEO. The result is often heartbreaking for the founder and JT knew there had to be an alternative.

Rogue Ventures aims to help budding companies by coaching them through a humanitarian lens, offering consulting services for startups. He envisions Rogue evolving to an early seed venture fund, but places emphasis on maintaining control with the founding partners who created the vision for their companies.

As I shamelessly scrolled through JT’s “About Me” section on Rogue’s website, I noticed a ribbon with pictures of him powering through Iron Man triathlons. Through these images, I felt an immediate connection. One of my favorite activities is mountain climbing in my home state of Colorado. Personally, I feel my greatest level of focus when I’m on the final pitch of a 5,000 foot climb approaching the summit. With no ropes and almost zero room for error, every motion is highly calculated and deliberate. I find the fatigue in the late stages of a climb to be challenging, and I wanted to know how JT battles fatigue in the later stages of a race.

I immediately sensed his sincere love for triathlons.

“Everybody has these sexy stories about how they woke up one morning and decided to be an Iron Man. Personally I find that story to be unbelievable.”

And why is that? I asked him.

“I’m sure you feel the same thing as a mountain climber. Not everyone wakes up one morning and says, ‘I’m going to climb a 14er today’. More often, they try to climb one and turn back from exhaustion a few hundred feet from the summit. But maybe they’ll make it the second time they try. Iron Mans and mountain climbing are inherently difficult tasks. While reaching the summit and crossing the finish line feel incredible, you will never reach that point unless you fall in love with the process of climbing, swimming, biking, or running”.

I dug deeper, and asked JT if he felt any of these lessons were applicable in the development of a business.

“They’re nearly identical,” he said.

“In business, I’m constantly reassessing my strengths and weaknesses. I focus on what I’m good at and find ways to overcome what I’m bad at. As is the case with climbing or triathlons, you develop a unique skill set over many iterations of similar tasks. The same ideology is applicable to a business skill set.”

JT’s words reminded me of my first 14er. Quandary Peak is hailed as one of the easiest of Colorado’s 54 ranked peaks, yet I struggled immensely scrambling up it. It wasn’t until years later that I developed the physical and emotional skill set to push myself up the more challenging peaks.

On the subject of personal growth through the headwinds of adversity, I asked JT what he hopes to have learned from the pandemic environment when he looks back on it in five or ten years.

“Perhaps the hardest part of this environment is navigating the emotional complexities of something none of us have experienced before. I’m aiming to grow as a businessperson through this pandemic, again taking inventory of my strengths and weaknesses and developing a plan to move forward. I also hope to pay forward some of the lessons that I’ve learned in my journey. I know just how hard it can get at times, and if I can help coach someone through that, I feel I’m doing a good job.”

I then challenged JT to think about the stories of the many who have failed through this pandemic. Nearly every business, big or small, has experienced failure in 2020 to some magnitude. I asked JT’s opinion about the role of failure in business and life.

His response included an anecdote about basketball, where he mentioned Michael Jordan’s famous 1983 mid-range jumper. We can all bask in the success of the moment, but JT proposed the idea of Michael actually missing that shot. What would the outcome have been?

JT noted that Jordan wasn’t always successful at basketball. He struggled considerably through his high school years, including getting cut from the Junior Varsity team, but developed a tenacity and ambition to constantly improve at the sport.

Even if Jordan had missed that shot, JT unquestionably feels that he would have still been the greatest player of all time. Jordan would have gone back to the gym the next day and taken hundreds of jumpers to ensure he would be better next time. The key to his successes was not in his high points, but rather his mentality and drive through the low points.

Additional Resources:


Michael Jordan's Failures

The Astral Consulting Group approaches every business case with a clean slate, and applies our unique framework to build a workflow to suit each client's individual needs. Our founding partners come from engineering backgrounds, and understand the importance of reasoning from the ground up. As such, we combine this "first-principles" style of thinking with a holistic growth mindset to evaluate each case from both the top-down and bottom-up. This creates a comprehensive process unique to each solution we develop, and gives our clients insight into both the granular details of their business and the high-level strategy and vision to propel them forward.