Alumni Spotlight: Lessons I’ve Learned about Entrepreneurship: Pt 1, Getting Started

Author: Kevin O'Keeffe

Kevin O'Keeffe ESTEEM '15Kevin O'Keeffe ESTEEM '15

Editor's note: This post is the first in a series of articles written by an ESTEEM alum who has been successful as an entrepreneur, and wants to share the lessons he has learned.


Getting started as a young entrepreneur is a challenge, even if you think that you are ready. Sometimes the hardest thing to do is sit down at your desk and simply begin the process of building a company, particularly if you come from a family background without any business ownership or generational wealth. It is this initial inertia that causes most startups to fail before they begin. Luckily, ESTEEM can teach you some of the processes and skills needed to take on the daunting task of a startup as well as introduce you to future co-founders, investors, and advisors. The key benefit of the program is that it can give you that push you need to overcome the inertia common to all new ventures by answering some of the tricky questions and demystifying many aspects of business.  

This is exactly what happened in my case. As a fresh graduate (having just completed my undergraduate degree at University College Cork) and an immigrant arriving in the US, I was faced with a steep learning curve as well as a wide variety of opportunities and choices for how to proceed on my career path. One non-negotiable outcome of ESTEEM for me was to start a business during the program. I was determined to find out if I was cut from the right cloth to become an entrepreneur and the only way to do this was to make the attempt. Over the course of the year, I experimented with several startup ideas and eventually founded a company along with another ESTEEM alumnus, Finn Pegler. This was originally planned as an experimental “side gig” but five years after the first revenue hit the bank account, we operate in four states (the newest location is Super Cleaning Service Louisville) and we are experiencing strong growth year over year. Finn and I now split our time between the management of our growing business, travel and working on other projects of interest to us.   

I have found that setting expectations is a crucial first step when starting a new venture. This project will be a large part of your life over the next few years, possibly even the next 10, 20, or 30+ years so it is important to define what you want out of it and what you will and will not do. In my case, the goals were clear – develop a scalable, fully online, recurring revenue business that could be run from anywhere in the world with minimal upfront investment (as a graduate student, access to spare cash can be limited!). Another critical aspect of the business model was that it should be possible to run the initial startup while also working a regular job in order to de-risk the process for the founders. It is really important to be honest with yourself at this point – are you passionate about a particular product, service or industry? Do you simply enjoy some aspect of business which you want to focus on? With these requirements in mind, you can begin the research phase of a startup. 

The research phase quickly revealed that there are many ways to create value for customers. The startups that make the news headlines usually ride a wave of hype surrounding a novel innovation and can be seemingly immune to the capitalist feedback loop which normally punishes an unprofitable business. Most companies, however, can and do make a profit even in their early days which means that most companies do not need much initial startup investment, particularly in less capital heavy industries like service industries. The U.S. Small Business Administration has reported that main street businesses account for 44% of economic activity in the US and create two-thirds of net new jobs. These are the business models I chose to focus on with my research. 

Luckily for us millennial founders, the internet has changed the way information is shared forever and truly has opened up endless possibilities for new ways of doing business. Sharing both hard data and anecdotal evidence with other business owners in real-time as you experiment can remove some of the trial and error elements of startup research. Online forums like Reddit, Quora, Linkedin and others are rich with valuable insights into particular business models. Experienced business owners are often happy to share their insights and experience with younger founders during coffee meetups or video calls and many lead online communities dedicated to certain business models. Several months into the research stage, the business model was beginning to crystalize. Eventually we settled on a service business model based around home cleaning as the service. It ticked all the boxes, especially the recurring revenue aspect. Due to the quality of the information available from other entrepreneurs and the fact that this was a mature industry with low barriers to entry, we immediately began the execution phase. 

Execution is where you can take some of the concepts and best practices taught in ESTEEM and apply them to the real world. The next few months were a blur of coffee fueled evenings and weekends where the practicalities of startup were dealt with. One by one the boxes were ticked. LLC filing, bank account, first hire, first customer and with a feeling of elation and triumph, first credit card charge. This stage can be a slog – there’s no getting around that, but this is the opportunity to learn the processes and find out what works so that you can hire for these tasks down the road. Reaching real scale requires you hire for the tasks you understand and keep yourself at the leading edge of your growing business. We knew from our research (and quickly saw it in the real world) that we would compete and win market share based on our ability to provide unparalleled customer support, the cornerstone of which is communication. Luckily for us, running an online business meant that we could staff our operations support team with talent from anywhere on the planet. The tools we used (mostly Google suite apps like Voice, Gmail and some niche business scheduling software) worked just as well with a team of two as with a team of twenty. Soon our small business was growing, and we were learning to think about scaling.

In my next post I will explore the process of scaling up digital marketing channels as well as building out a fully remote, online team. This is where the business really comes alive, as the entrepreneur is now working on the business (not working in the business). 


Kevin O’Keeffe (ESTEEM '15) hails from Ireland where he was awarded a B.E. in Chemical Engineering before emigrating to the US and completing the ESTEEM Program at the University of Notre Dame. Currently based in San Francisco, he is co-founder of an expanding local service company serving Indianapolis, Milwaukee, Louisville and Oklahoma City. 
If you enjoyed learning about Kevin's journey in entrepreneurship, read more about these other ESTEEM Alumni: