Singing*— “Time keeps on slippin’… into the future.”
Whichever rendition you prefer, neither The Steve Miller Band nor Seal lied when they sang these lyrics because, unlike Moneybagg Yo, I just looked at my wrist and don’t have time today. And, I didn’t have it yesterday or the day before either.
WTH? Where does the time go?
Something has gotta give.
As for me, I am taking intentional steps to gain a return on time (ROT).
Reflecting what we as startup founders know, the study confirmed that CEOs never stop.
The study revealed that CEOs:
Sound about right?
If you’re anything like me, you’re thinking: Let’s double those weekday hours. As tech CEOs, we work even more.
According to First Round Review, “[t]he average tech CEO works about 300 days a year, 14 hours a day.”
As an entrepreneur, especially when we’re in the early stages, this is the story of our lives. And managing our time is often the most challenging part of the gig. Therefore, receiving a Return on Time (ROT) may seem inconceivable, but believe me, it’s not!
Over the past 13 years ago, I’ve evolved as a leader. I have learned from my many successes, but even more from poor choices, past failures, and other humbling experiences.
Early on, I unintentionally squandered time—giving it aimlessly to any and everything, taking meetings with anyone, then realizing that I hadn’t accomplished anything I needed to complete.
As a result, I stayed up all night, completing tasks I was unable to complete during the day because of all of the meetings—some planned and others impromptu, but a majority of them longer than necessary.
I allowed e-mails and other unplanned tasks to distract me throughout the day.
This “fly-by-the-seat-of-your-pants” behavior was unmanageable and left me always playing catchup.
We are not alone.
Founder, operator, advisor, and angel investor Bill Trenchard penned the First Round Review blog titled, “70% of Time Could Be Used Better – How the Best CEOs Get the Most Out of Every Day.
According to Trenchard, 70% of approximately 4,200 hours that tech CEOs spend working each year is sub-optimal.” He writes that nearly 30% of that time is devoted to e-mail and another third to meetings, with tech CEOs wasting almost 2,100 hours each year.
These numbers are astounding!
Over the past decade, my relationship with time has evolved but not perfected.
Because I want to save founders of newer startups the trouble of developing poor time management skills, I assessed my evolution with time—taking inventory of those habits that have enhanced my relationship with time and those that have constrained it.
This inward assessment inspired the creation of Hutch’s recently published guide to help founders and CEOs manage their most precious commodity—TIME!
My hope is that this tool along with the transparency of seasoned founders who have dropped balls, missed opportunities, and fractured relationships will avert new founders and CEOs from making the same mistakes.
The residual effects of poor time management will reveal themselves at the most inopportune times.
Believe me, I have many stories to share, as well as some bumps, a few bruises, and the T-shirt to prove it.
I had the perfect getaway planned.
After all, 15 years of marriage is not for the faint of heart for even the most mundane couple. So, consider a 15-year-marriage that included a medical residency, a tech startup, two kids, and two ever-advancing, highly successful careers.
Undoubtedly, what Dr. Letitia Dzirasa, whom I affectionately call Tish, and I have is extraordinary.
So, our celebration had to be perfect. I looked at my beautiful wife, who was relaxing on the other side of our suite.
“Babe, we have three hours to spare before it’s time to get ready for dinner. Want to head to the beach, grab a drink, or visit the shops? It’s your world.”
As Tish contemplated my options and likely considered alternatives, I inadvertently clicked on my e-mail out of habit. Some habitually check social media accounts, but I habitually check my e-mail. Yes, even on vacation.
“Oh shoot,” I said.
As I read the e-mail, a mix of emotions overtook me.
I had been working to partner with the National Football League (NFL) for months— flying to and from Los Angeles, meeting with NFL executives and representatives of the United States Small Business Administration, and even legendary rapper, actor, and filmmaker Ice Cube.
It had been a work in progress with me at the helm.
Finally, it had come together, and they were ready to move forward. It was a dream come true
They needed a proposal within the next few days.
I thought to myself, “Is this happening?”
I had planned to check out of work, lock in with my wife, and take full advantage of this time away. After all, we deserve it.
Over the past two years, she led Baltimore through a global pandemic while raising our young child, and I grew Fearless into the largest software development firm in the Baltimore region.
None of it was easy, but all of it was worth it. Now, it was our time to relax, recharge, and reflect, while celebrating this triumphant milestone.
I’m sure you all have heard of the “6P Rule”—Prior Proper Planning Prevents Poor Performance.
They are great words by which to live.
However, I had not prepared the proposal for this tremendous opportunity I knew was looming.
I had spent the week reacting rather than preparing.
Knowing I could potentially receive this opportunity and not being ready was a rookie mistake.
While I didn’t know exactly when it would all come together, I knew it was highly probable. And when it did, I would have to be ready.
Yet, here I was on vacation, unprepared for this transformative business deal.
But, it gets worse.
Unlike all of Fearless’ other contracts, I had held this opportunity close to the chest, failing to assign it to a portfolio manager or at least bring someone else up to speed on the project.
Because it was such a huge endeavor that I had taken the lead on, I felt I knew the most about all of the inner workings and had to keep my hands on it.
I had made an exception to the process, which had backfired tremendously.
Now, here I was on a lone mission.
“Honey, I’m sorry, but I now need to handle something. How about I book you a spa treatment for the next few hours, then we can head out for dinner?”
Because Tish believes in the success of Fearless as much, if not more than me, she gave me the time and space I needed to complete the proposal that led to Fearless’s inclusion in the NFL’s $125 million investment to increase economic equity by partnering Black-owned businesses.
However, it didn’t absolve me from feeling like crap.
My response is: “And, so am I!”
Let me spare you the math as you try to figure out how long I’ve been married or begin scrolling through Fearless’ social media feeds to determine when we secured the NFL deal.
This just happened in February of this year.
Look, don’t judge me. Bad habits are hard to correct.
For this reason, I am committed to helping new founders take control of their time.
Almost immediately, through market research, we learned a lot. While startup founders aspired to receive return on their investment (ROI), even more so, they needed a return on time (ROT).
Transparently, Hutch participants valued their time and wasting any of it was an aspect of business that troubled them most.
While money was significant, time was king.
Apple Founder Steve Jobs once said, “My favorite things in life don’t cost any money. It’s really clear that the most precious resource we all have is time.”
Hutch participants reminded us that Jobs’ sentiments still ring true.
As a startup founder, I wholeheartedly understand the pressure of feeling like there’s never enough time.
We’ve all been there,
This is all unacceptable but has become a lifestyle to which we have become accustomed.
Therefore, we had to reassure them that Hutch was a wise investment.
We had to convince them that Hutch would accelerate the startup process, helping them overcome hurdles they likely would have faced without our guidance and support.
But, most importantly, we had to prioritize their need for a return on time.
This was a mutually beneficial challenge as I have been working on my time management and task prioritization for as long as I’ve been in business. While I have mastered it at times, I sometimes get off track as the business grows and evolves. However, the resounding feedback of our Hutch company founders required an executional vision.
Mastering these skills will save founders from squandering their time on things that are not advancing their business goals.
We recently published a Prioritization Playbook by Hutch to help founders and CEOs focus their time and energy on the things that matter.
The playbook highlights the seven “plays” listed below.
These are all plays that I have acquired over time and am always working on mastering.
Founders and CEOs often have a vision for their businesses. However, balancing the long-range goals with day-to-day business development and operations does not come naturally to all, making it difficult to separate the forest from the trees.
Hutch published a blog, titled Tips for time management for CEOs who want to reclaim their time, providing five plays to help leaders take control of their time.
The Prioritization Playbook and Time Management Tips enumerate actual plays that I have incorporated into my personal and professional life over time.
And, I challenge you to do the same if you really want to grow and scale your business.
To be honest, maximizing your time by ensuring that every minute counts is a critical component to successful expansion.
Believe me, these prioritization plays and time management tips have shifted my way of thinking, resulting in Fearless’s exponential growth.
For instance, I once was driven more by impact than output.
However, by applying Prioritization Play #3, I was able to create and continuously reassess operational and strategic plans that set and prioritize long-term goals, providing a vision for investors, team members, and clients.
And, staying on task daily to advance and execute those annual goals has required the disciplined application of Prioritization Plays 2, 4, 5, and 6 because the daily distractions come way too easily.
From the onslaught of e-mails, texts, and calls to the never-ending “To Do” list, I don’t know how I got anything done before implementing the prioritization plays and time management tips. So, let me save you the headache.
As New York Times, best-selling author and businessman Harvey Mackay once said…
“Time is free, but it’s priceless. You can’t own it, but you can use it. You can’t keep it, but you can spend it. Once you’ve lost it, you can never get it back.”
Like most CEOs, the daily return on time requires me to prepare at least a day ahead, which has its challenges.
Driven by making an impact, my ability to stay on track daily takes much deliberation and assistance. Honestly, I often operate from the two ends of the spectrum and never much in between—sometimes overly disciplined and other times very fluid.
I must prepare the day before and stick to my prescribed daily schedule.
This can be a lot, but it always pays off because I feel aimless when I stray from this level of discipline, often concluding the day feeling unproductive and out of control.
In my more wayward times, it feels like everyone and everything are running the business rather than me, and that is a serious problem.
But when I am more disciplined, I can separate the forest from the trees, allowing me to prioritize those tasks that further the overall objective and ignore everything that does not. This leaves me feeling accomplished and focused.
The difference in these times is motivation.
So, it is vital that I apply Time Management Tip #3: Dream up my ideal calendar my daily productivity is based on the night before. Therefore, scheduling my ideal calendar than adhering to Tip #4: Bringing someone in to enforce it is imperative.
With my adrenaline pumping and endorphins overtaking, at this point, I am highly motivated and ready to “Win the Day.”
While the founder and CEO of a fast-growing tech firm, I maintain my tasks the old-fashioned way—with good ole’ sticky notes that I keep next to the trackpad on my laptop.
I know, I know…pretty basic?
But, this fundamental aspect of my routine keeps me on track. I do not get distracted by applications and other shiny technological gadgets. I can see my task, accomplish it, mark it off, and move on to the next item. It is key to my optimal return on time.
I maintain these lists throughout the week, listing my tasks in order of priority.
If I do not complete a task, it is added to the sticky for the next day until it is completed.
However, compiling this prioritization list is not arbitrary. It takes much thought as I dwindle what outstanding tasks I must complete versus those I can delegate. Then, I rank them in order of priority.
This line of questioning causes me to pause and consider the best and worst-case scenarios in each situation.
When I go through this exercise, I can appropriately delegate tasks, only keeping those for which I am the best to do it.
I could have and should have brought this major deal to our COO, my partner, John Foster, and our Chief Growth Officer, Greg Godbout. After all, this is what they do.
Over the three years that Greg has been with us, under his leadership, we have secured a $120 million Blanket Purchase Agreement with the United States General Services Administration.
He, alone, is more than qualified to handle the NFL contract.
This epic fail infringed on my time and brought in team members who could have been planning and strategizing later rather than earlier. Based on our decision to hold the potential deal, I brought my team in on game day without having afforded them the benefit of a few practice rounds.
In 2009, when I started Fearless, I was trying to paint a dream that others could grasp. I constantly tried to convince people—selling them my vision, setting the tone for the future, and creating a culture that inspired people.
By 2016, we saw a shift. We were all finally working in one centralized location, and our work portfolio was not as heavily classified as it had been. Therefore, our growth required more focus which required discipline. Consequently, I was often in survival mode as I attempted to demonstrate the Fearless culture in person while also growing and scaling.
After creating and sustaining a dope company structure, we have proven that we can do the work.
At times, I may fall off track, like in February when I was handling the NFL, which resulted in me working during my 15th wedding anniversary vacation. However, it is comforting to know that I have these plays to guide me as I work to get back on track.
Now, as I sit here, preparing for tomorrow and compiling my Prioritization list, at the top of this list is:
I will use the Prioritization Plays and Time Management Tips to properly prepare for a work-free trip and trust myself and the process to know that Fearless will be fine while I spend much-needed time with my queen.
Until successfully planned, it will remain at the top of my list!