There’s something timeless about a fire pit. It’s more than warmth — it’s a gathering place for thoughts, stories, and connection.

Around a fire, solitude feels different. The quiet crackle gives space for reflection… for thinking deeply, honestly, and without distraction. It’s where vulnerability meets clarity — where you sort through ideas that don’t surface in the noise of the day.

But the magic grows when others join in. Family. Neighbors. Friends. Teammates.. Suddenly, that same fire sparks brainstorming, laughter, creativity, and new energy. The glow becomes a circle of trust — where the best ideas, and the best versions of ourselves, come to life. I’m also confident in saying that some of the best business ideas came to light around this circle of fire vs the wooden table in a conference room. Finally, let’s not forget where many of the greatest music playlists have been generated. Judged .. and then deployed to the masses.

So whether it’s a night alone in thought or a late conversation that changes everything… never underestimate what a simple fire pit can ignite. 🔥

hashtag#Reflection hashtag#FirePitMoments

I received a call two days ago from my good friend, founder, pastor and mentor, Pastor Corey Brooks “Hey Kayne, want to join us in NYC on Friday and ring the opening bell?” I am not sure that I allowed him to finish the sentence and interrupted with “ABSOLUTELY!”

Ringing the bell has always been a dream of mine, a bucket list item, etc. Although it wasn’t my company, we weren’t doing an IPO, it exceeded all my expectations.

First, I will say that the NYSE team are true professionals. Before we walked into the building we were welcomed with massive signage. Upon getting thorough security, we were led to an incredible waiting area with breakfast, a ceremony for the Pastor, and picture taking event. We then moved to the floor for more pictures and opening the market with the customary ringing of the bell. Hats off to the NYSE team for a wonderful day.

Most importantly, I want to congratulate the entie Project H.O.O.D. team. Your passion, your effort, your dedication towards building this community center and reducing violence in Chicago is so inspiring. Seeing Hood’s logo on the building and all over the trading floor is a true testament of those that are listening, watching and offering to help.

Finally, I want to share something directly from the Pastor:

“From O-Block to Wall Street. Today, we rang the bell at the New York Stock Exchange not just for Project H.O.O.D., but for every block that’s been overlooked, every life that’s been written off, and every dream that refuses to die. Hope has an address. And now, it has a voice on the biggest stage in finance.”

#FromOblockToWallStreet #NYSE #ProjectHOOD #WeCanBeBetter #OpportunityBlock #UrbanRevival

Ah.. it feels good to be back ..

“If you want something you’ve never had, you must be willing to do something you’ve never done.”

It’s been 30+ years working, learning, succeeding, failing, and gaining experience to finally do something on my own. I feel fortunate to finally become the sole owner of a company. After six months of searching for an ideal company to acquire and another four months of due diligence/deal closing, I am excited to announce that I have acquired United Transportation through a newly formed entity called Graxon Logistics.

After my work at Uptake and being entrenched in logistics and transportation sector, I became captivated with this space. The possibilities for greater innovation, efficiency, transparency to the end customer, driver satisfaction, and safety were (and continue to be) endless. Over this three-year period, I had a unique opportunity to interface with OEM’s, dealers, operators, and drivers. Every level had me intrigued on the problems we were solving and solutions that could still be developed. During my evaluation process and search, I purposely narrowed it down to something niche within the industry. It needed to be service oriented with massive expansion opportunities worldwide. United Transportation became the obvious choice.

I am taking the torch from a visionary founder, Ricky Singh He has been a true professional, partner, and friend throughout the transaction. I’m deeply honored and humbled to build on the incredible foundation he has created over the past 15 years. His dedication and passion have shaped United Transportation into what it is today. With our amazing team, I’m excited to explore new opportunities, embrace challenges, and continue creating value for our customers, partners, and community.

I want to thank Tom Keenan for the introduction to Ricky and joining me on this journey. Tom has close to 30 years in warehousing, logistics, and trucking. He will be an unbelievable asset to help with nurturing our existing customer base and assisting me with rapid expansion. In addition, I want to thank Scopelitis and Byline Bank for assisting me with closing the transaction. Finally, thanks to my wife, family, friends and mentors in my network that I relied on for advice and critical feedback.

I couldn’t be more excited to be in our O’Hare warehouse and get my hands dirty. If ever around the area and want to see the operation in person, let me know….

It’s GO time!

There’s a vision emerging on the near Southside—one that can be best seen from 19 feet in the air.  

There, atop a stack of shipping containers, Pastor Corey Brooks is living in a tent until February 28, 2022, braving the cold Chicago winter to promote his radically ambitious plan for the Englewood-Woodlawn neighborhoods. And he deserves our help. 

Pastor Brooks, Senior Pastor of New Beginnings Church, is also the founder of Project H.O.O.D. (Helping Others Obtain Destiny), an organization committed to providing mentoring, job training and community services for one of Chicago’s poorest and most crime-ridden neighborhoods. Ten years ago, he camped for 94 long, freezing days and nights on the roof of a long-closed hotel near the corner of East 66th St. and South Martin Luther King Jr. Drive. That decrepit structure, abandoned and used only for drugs and prostitution, was eventually torn down with the funds Pastor Brooks raised during his campout. 

The Pastor’s ultimate goal for that property, however, has yet to be realized. He undertsands that without skills, without encouragement, without self-esteem and a firm belief that one can succeed, there is no hope for individuals, families, or entire communities. That’s why he has set his sights on a major plan to build and operate a community center dedicated to improving, even transforming the lives of thousands of local residents. 

It is an enticing vision indeed. The center will bring 400 new jobs to the neighborhood—but that’s only the beginning. It will provide trade school training in construction, plumbing, electrical and other sorely needed occupations. It will support the arts with theater and dance studios. A swimming pool and golf simulator will allow urban youth to learn sports they would otherwise never have a chance to try. It will include three restaurants where food service skills can be taught. 

Eyes, Hearts Opened 

Big ideas, however, require big gestures and big support—which is why Pastor Brooks has once again pitched a tent above his beloved streets. This time, he’s asking for others to join him.  

His infectious dream has attracted scores of celebrities,  CEOs, political and religious leaders and many others, all of whom are spending at least one night with him in his little outpost. I had the privilege of joining Pastor Brooks on November 20, the first night of his 100-day commitment. 

As I huddled around his stove, listening to the Pastor talk, my eyes were opened to more than the night air. I discovered how much is happening, both bad and good, just a few miles from where most of us in Chicago live and work every day. I realized that the problems we face as a society are only solved when we, as individuals, step up and care. 

While some social challenges don’t affect each of us directly, we still have a responsibility to find answers. What impacts our neighbors impacts us as well. And when people like Pastor Brooks and his team not only develop a practical solution, but also put their personal blood, sweat and tears behind it, we have an obligation to assist. 

This 85,000-square-foot initiative, called the Leadership and Economic Opportunity Center, will be a stake in the ground for the Woodlawn and Englewood neighborhoods. It will be a safe place for kids to gather after school. It will give recently incarcerated adults a way to transition to gainful employment and eventually become financially independent. It will offer programming for teens on nights and weekends, encouraging kids who otherwise might not have a place to go to spend their time learning and contributing positively to their community. 

Moreover, this kind of center has huge potential for replication. If it succeeds—and I have no doubt it will—it will be a model for other Chicago neighborhoods and ultimately other cities across the U.S. to follow. Pastor Brooks’ idea is a powerful engine for change. 

Make It Happen 

Grand undertakings are rarely inexpensive. The Leadership and Economic Opportunity Center, already designed and planned through the voluntary contributions of leading Chicago architects and construction professionals, has a price tag of $35 million. Seven million dollars have already been raised—but there is much more left to do. 

Tens of thousands of people have already supported the project, either directly or indirectly, through their time, effort and contributions. Corporate financial support, along with additional individual and organizational giving, is still sorely needed to drive the movement forward. To donate, please visit the Project H.O.O.D. website.  

If you can’t donate money—or even if you can and you’re looking to take an extra step—donate a morning or afternoon to the cause. Come and see firsthand what is happening at Project H.O.O.D., from the computer coding programs for girls, to the classes on stocks and investing, as well as the summer boot camps for boys. There are many, many opportunities for professionals of all specialties and backgrounds to share their knowledge. 

Finally, I’m challenging at least a few dozen Chicagoland CEOs to sign up for a night with Pastor Brooks during his Tent-a-Thon. Spend an evening with him as he shares his insights and ideas for how we can better our community. Look out over a portion of our city that is starved for attention. Bed down for the night with a new sense of participation and purpose.  

Make the climb. You will come down unbelievably inspired. 

To sign up for a night at the Tent-a-Thon, visit www.projecthood.org/tent-a-thon.  

Since I joined Uptake as President two months ago, I’ve been listening. This comes in the form of stand-ups, weekly staff meetings, happy hour Zoom sessions, and my weekly talks with our Founder and CEO, Brad Keywell. Through my various conversations with our employees and senior leaders, I have gotten the advice to focus more on the culture and what drives our high-performance work environment. With more than 20 years managing teams, I have learned many different ways to dissect the strengths and opportunities within an organization. In the end, the most effective tool is to simply dig in and meet with employees directly, having unfiltered and honest conversations. Yes, this will take time and you have to balance the meetings with your other dozens of tasks as the new leader, however there is no better validation than what you hear in these one-on-one sessions. With 100 employee conversations completed thus far at Uptake, I am consistently hearing one word: culture. All things culture. 

What is culture? Maybe it’s best if we first define what culture is not. I’ve seen companies spend hundreds of thousands of dollars on lavish offices and amenities. These are award winning office spaces, with visitors having office envy. One can appreciate the artwork, modern furniture, beer/coffee taps, cafeterias, and pickleball courts. These are amazing employee perks; however, does this define your culture?

For me, this is not culture. These objects are simply artifacts of culture. While they may contribute to a healthy and fun work environment, they shouldn’t be considered the motivators behind your culture. Nothing is wrong with creating the fun work environment, however is this truly retaining your highest performing employees? With many of us working from home today, I would like to assume everyone’s workplace is being validated in a real-time manner. How is it working out?

For me, a positive and high performing culture is the shared understanding of company values, transparency to business and professional goals, effective communication, and consistent recognition.

Celebration happens bidirectionally, from the top down and bottom up. Because culture can mean a lot of different things to different people, I’ve been diving into this topic very specifically and very attentively with our staff. My conversations have been unbelievably informative, transparent, and productive. Each Uptaker is helping me personally to think about the core internal strengths of Uptake and where we can concentrate on opportunities for growth.

What’s been inspiring from my conversations is the incredible amount of diversity, talent, and breadth of expertise within Uptake. Backgrounds, experiences, and projects that our employees have done pre-Uptake or while at the company are impressive, and they also point to our collective potential. An important part of that promise is that Uptakers aren’t strictly technologists. One of our teammates has a background in meteorology, and they bring that to bear when building products and factoring in contextual data. Another spent time in the Los Angeles entertainment/film industry, working with clients on really hard deliverables and projects, and they now ensure that our customers are satisfied and derive value from our products. Our immersion in heavy industries is the foundation for our expertise, yet the unique perspective our people bring of life far-flung from the worlds of chemical processing and discrete manufacturing are equipping our team with the agility and creativity to tackle some of the most difficult industrial challenges.

One of our greatest strengths is innovation, driven by our diverse and deep employee experience. It’s an organic strength because longtime Uptakers dream big and build amazing products and services. As a new employee, you see and feel this within a couple of days of arrival. There’s still a month-one start-up hunger that drives us in our sixth year, and creativity in data science, products, and technology, is an expression of that collective pursuit and ambition. The insatiable desire from our team for better, more, stronger, faster is absolutely part of the culture I see consistently at Uptake.

Another core strength of Uptake’s culture is asynchronous clarity. Brad Keywell has spoken about the term as being an important part of remote work. It’s the ability to know how to navigate the digital world and have access to the information you need to do your job without being able to stop by someone’s desk and ask about who has responsibility or expertise over a certain area. Uptake teams deploy software for customers all around the world from their own living rooms. With the crystallized clarity around roles, responsibilities, and who is doing what, we can move swiftly towards achieving our company goals. There is pride and a sense of mastery over one’s area of responsibility as well as a mutual understanding and respect for our colleagues with full alignment towards the greater good of our organization. These are critical building blocks for a harmonious and an effective remote work environment. I consider that ability to effectively work remote and related to talent, ambition, and expertise. From day one, it’s a part of the organic start-up culture Uptake has built as an Industrial AI company.

So, what is culture? It’s a question that merits re-asking frequently because culture is something we do, not something we have.

I’ve learned that each Uptaker will give you a slightly different answer, but the openness to give an answer at all and to question is why I’m encouraged. As I listen to each and every team member, I’m gaining a fuller picture of our everyday culture and our collective commitment to the direction of our company.

I don’t know about you, but I’m learning a lot in 2020. For starters, I’ve incorporated “synchronous” and “asynchronous” learning into my daily lexicon. I’ve also discovered that one of my kids likes to do remote school in his room, one prefers my wife’s office and another chooses to Zoom from the dining room table. Also, no one likes the basement.

Though it has taken us several months to navigate work, school and life in general during a global pandemic, my personal party of five is getting pretty good at working together, understanding each other’s nuances, quirks and idiosyncrasies, and perhaps most important, learning from each other. With that learning, comes inevitable growth. It’s a lesson I value greatly during this time of uncertainty and larger unknowns. 

A little over a month ago, I joined Uptake, the Chicago-based industrial data science and artificial intelligence (AI) software leader, as the new president of the company. There was a very nice news release written and like other press announcements regarding business leadership changes, I talked about strategies, value proposition and “excelling in a digital world.” While my statements are true, I’ve never been more ready to run a company like Uptake. I accepted this position not just because I want to help grow the company and expand its global footprint. I took this role because I believe, at my very core, in the power of people. Those that listen, connect and learn from each other, build something meaningful together.

I’ve spent the last five weeks becoming acclimated to this new position. My conversations with various team members have been thoughtful, meaningful and extremely inspiring. I’ve also spent a fair amount of time with Brad Keywell, our founder and CEO. I was fortunate to establish a partnership with Brad in 2015 while co-founding DRIVIN together. In the earlier stages of the build out, we collaborated frequently, as both DRIVIN and Uptake were being built on the same floor. With a background in data and analytics, I had a deep appreciation for what they were building and solving in the industrial sector. Over the past five years, Brad has assembled a smart, dedicated and talented organization that I’m fortunate and proud to now call my colleagues. It’s a tremendous opportunity to reimagine the future of Uptake and working along someone that I admire and trust.

In coming to Uptake, I bring some past successes to the table including the acquisition of DRIVIN to KAR Global, where I spent three years utilizing data to strengthen their digital products and services. I also carry failures, some larger than others. These learnings would become building blocks for the future or as I like to call my “crash-course MBA.” I’m proud of and humbled by both and know that every role I’ve ever held has ultimately prepared me for this one. 

I know it will be a process. It will take time to take in the history of our collective successes and failures to develop and execute a flawless strategy and plan that unequivocally meets the needs of our customers. But we’ll do it by cultivating connections, setting aspirational goals, and investing in each other. We’ll build momentum with energy and passion, one small win at a time. If there’s anything I’ve learned over the course of my career, it’s that success comes from the willingness to learn. Good leaders are ALWAYS “under construction.” I have much more to learn and look forward to my continued education within Uptake.

I was on a flight recently, fiddling with my phone, trying to get an app to work correctly. My six-year-old daughter, who was sitting next to me, reached over the armrest, gently took the phone out of my hands, and said, “Dad, you’re doing it wrong.” (She’s blunt, that little one.) But she was right. I was in fact, doing it wrong, and at that moment, it was evident that my pint-sized techie was clearly smarter than me.

Having participated in many early staged companies, building a business is quite similar. Whether you have 5 or 75 employees, everyone is working harder, doubling responsibilities and fulfilling new and unforeseen roles. As a result, there are a lot of ups and downs. The team can be very high one day and beyond low the next, always testing the culture of your organization. Survival in most cases is dictated by who you have hired.

At DRIVIN, we want to become the NASDAQ of the used car industry, using a recipe of human capital and data to create a frictionless service for dealers to source, acquire and deliver quality vehicles. We’re building a two-sided network that has never been built before and solving an industry-wide problem for dealers. It’s a big undertaking with no playbook to copy. To make this all work effectively, we hired a world class leadership team and it was methodically created from day one. Having previously learned this the hard way with my fair share of hiring mistakes, I have come to the realization that it’s not my job to be the expert at data, technology, marketing, operations or sales. It is my job to hire the right people to perform these roles and not be afraid or intimidated by their experience. Although early, I believe this is why DRIVIN is succeeding.

To give you a simple analogy, I consider myself the band manager; I assemble the band, get people to the venue and then allow the band to do the show, with the knowledge that the set list will change regularly. I can say with certainty that DRIVIN earned the Moxie award for Chicago’s Best New Startup because of the determination of a hard-working team, comprised of dedicated people who are specialists in their field. We are all “marching to the beat of the same drum.” We are transparent, we are honest, and we have trust in one another.

I have found that the real work begins when you recognize your own limitations, put aside your ego, and make yourself vulnerable to recruit and hire ambitious employees and leaders who not only meet the qualifications for the job, but also enforce the company culture. Done right, they immediately become the true experts within their respective jobs. As the leader of the organization, you step aside and allow them to make the magic happen. It’s my job to keep the larger organization focused and set the pace, tone, and direction.

In the end, as the leader, it’s critical that you allow yourself to be outshined by people who are smarter and more talented, as this creates growth and a stronger organization. Be passionate in finding the A-players and those with exceptional talent, intelligence, and drive. Most importantly, find people that challenge you on a consistent basis, as this will improve your personal skills and experience.

Now, excuse me while I check in with my six-year old and get schooled on using my smartphone more effectively.