Superhuman Business Owner
The Calling
Growing up, I was convinced medicine was the highest calling anyone could have. Everything I did up until 2011 was aligned to becoming a doctor. Then in the summer of 2012, I suddenly realized I didn’t want to be a doctor. After taking the Medical College Admissions Test (MCAT) twice, painstakingly writing essays, and finally submitting my medical school application, I made one of the hardest decisions of my life - I withdrew my application. I’ve never felt more lost or uncertain than I did that summer. For three long years, I drifted without direction. Despite having a successful job at the time, I was deeply frustrated and confused about what I wanted to do with my life. Then one day, I stumbled upon a TED Talk by Fred Swaniker, who spoke about his entrepreneurial vision to nurture the next generation of African leaders. Something clicked instantly; I felt an undeniable pull, an itch I couldn't ignore. I answered the call and haven't regretted it once. Whether you've started your own business or acquired one, you probably felt something similar: a voice, a passion, an urge you could no longer ignore. At first, that feeling is exhilarating, but nothing truly prepares you for the transition from inspiring idea to operator.
Transition Hell: From Idea to Managing Reality
70% or more of small businesses fail within their first five years of operations. I have started two companies, so I understand firsthand the mental trauma and challenges of transitioning from the dopamine rush of an exciting idea to the reality of running business operations. In 2022, I started Garage Mobility, a B2B auto part marketplace that connected traders to auto part suppliers and provided inventory financing to ensure their shelves remained stocked. Within 5 months of operations, we were generating about 250K USD in monthly sales volume. It was incredibly exciting to see our idea take off but no one had quite prepared me for what came next. Most days I felt like I was losing my mind and struggling to keep up.
By day, I was wearing multiple hats - handling sales, procurement, fulfillment, inventory, HR, and finance all at once. By night, I was moonlighting as a business analyst, pulling data from disconnected systems, trying to understand our inventory position, whether we had enough stock to meet demand the next day, how much we had sold, and if there were any cash or inventory reconciliation issues. Fair or not, the world expects business owners to be superhuman. Other than raising my cortisol levels, this constant context switching also had some downsides for the business.
When you’re focused on growth and wearing multiple hats, it’s easy for things to fall through the cracks. What kills most businesses isn’t a single catastrophic failure, it’s the small inefficiencies, unchecked leaks, missed signals that slowly drain you until it’s too late. In our case, even though sales were growing, we were unknowingly overstocking slow-moving SKUs; placing repeated orders without realizing they weren’t turning. Over time, this quietly compounded and increased our inventory days. It wasn’t until we started facing pressure with payables that we realized we had a working capital issue. To free up cash, we had to heavily discount the excess inventory, which led to losses and strained our cash flow at a time when we needed flexibility the most.
Why Do Small Business Owners Struggle Through Transition Hell
Transition hell is real for many business owners and is an implicit reason why businesses fail. Most small business owners are experts on the product and service they sell. However, as the business starts growing, they are expected to be superhuman and wear multiple hats. This leads to things falling through the cracks such as poor inventory management, high discount dependency, high churn that’s remains unattended, etc and all these have significant impacts on a business’ cash flow which is one of the top reasons businesses fail.
As I reflect on my own experience and that of other business owners I’ve been fortunate to chat with, I believe there are three major reasons why small business owners struggle through transition hell.
First is poor visibility. During this phase, business owners are wearing multiple hats; yet they lack centralized, easy access to the data needed to make quick, informed decisions across functions. Information is often scattered across spreadsheets, disconnected tools, and handwritten notes, making it nearly impossible to get a full picture of what’s really going on in the business at any given time.
Second is the lack of operational forensics knowledge. Even when business owners start pulling data from different sources, many don’t yet have the mental models or experience to clearly identify what inefficiency looks like. For instance, stocking slow-moving SKUs while celebrating growing sales may seem harmless until you run into cash flow issues. Or you may think discounts are helping drive volume, without realizing you’re eroding already thin margins. Without understanding the levers that drive financial health, even well-intentioned decisions can quietly bleed the business. And again, siloed data compounds this issue because if you can’t bring all your information together, you can’t diagnose what’s going wrong.
Third is limited access or knowledge on how to use automation tools effectively. Even when inefficiencies are spotted, many small business owners aren’t sure where to start, what tools are available, or how to deploy them in a way that creates repeatable, sustainable impact. This leaves them stuck manually solving the same problems over and over again.
Together, these three challenges—poor visibility, limited operational forensics, and a lack of automation trap many business owners in a loop where growth hides inefficiency, and hard-earned momentum is slowly drained by the cracks beneath.
The key to unlocking abundance on Main Street is to significantly reduce the failure rate of small businesses. Over the next 10 years, millions of businesses will be passed down from boomers to first-time owners and many more will be created from scratch. These new operators will be faced with the same challenges of transitioning into operators.
In this series, Superhuman Business Owner, we’ll explore how to harness AI to help small business owners transition successfully into operators and scale their businesses without loosing their minds.
THIS WEEK ON MAINSTREET
📰Mainstreet Minute:
OpenAI recently launched free AI education through its OpenAI Academy. This is an ambitious project to drive the mainstreet adoption of AI beyond tech savvy users. small business owners, teachers, students and others can now access free courses through the ChatGPT creator. Not to be outmatched, google also partnered with America small business development center (SBDC) to launch AI U, an initiative to train over 100K small businesses on AI literacy and tools to help grow their businesses.
📌Quick Win Tip:
Brand24 is the fastest way to monitor your brand across the internet—without digging through dozens of platforms. It tracks mentions from social media, blogs, news sites, and forums in real time, and uses AI-powered sentiment analysis to surface what really matters. Let Brand24 handle the noise so you can focus on building stronger customer relationships, protecting your reputation, and spotting opportunities as they happen. Get a quick win this week by setting up real-time alerts for your brand with Brand24.
Great read!!