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Start A Business To Avoid Working Until 65

Start a business for success. Person climbing a mountain.

Hey friends! Today’s post on why you should start a business is a guest entry by a friend I made online who runs the personal finance blog Foundered. His name is Connor, and he is retiring early this year, and has quite the compelling story, which I know you will enjoy.

An introduction

I am not and never will be the best business person in the world. Or the smartest, and sadly, not the most handsome. But I’d give most people a run for their money regarding work ethic. I have been called many things in my day, but being lazy is not one of them.

Being successful in business isn’t about being the best, though. It’s about being willing to go further and to work harder than your competition. It’s about understanding your customers, what they need, and meeting this with your product or service at a price they are willing to pay. Mostly though, it’s about knowing your business inside out from the financial perspective. 

In this article, I will try my best to articulate some of the best financial lessons I’ve learned in business and how these transcend into our collective private lives—especially those of us on the path to financial independence. [For those new on the path to financial independence, I, Olaf, suggest reading the book Buy This, Not That by Sam Dogen. It lays out the groundwork and framework to achieve success.]

Old me

Hey everyone, I’m Connor, a 40-year-old, soon-to-be early-retiree from Ireland. I decided to start a business in my spare bedroom in 2009 with less than £1,000 saved. Since then, I have also created two complementary enterprises under the same brand, supporting our clients with various products and services.

I manage a team of forty employees and another twenty third-party contractors I work with daily.

All three of the brands were acquired by another entity in November 2020, mid-pandemic. I am only a few days from exiting the business I created and retiring early!

New Me

I take my daughter to school most days. I am home from work on time every day. I am learning to play golf and trying my best to make house and techno music.

I live a relatively simple and drama-free life most of the time. I am present, and as someone who spent 60, 70, or 80-hour weeks working previously, this is a welcome change in mindset. 

Financial lessons learned in 13 years of business

There is never a perfect time to start a business. There will always be significant and scary challenges to overcome. I left a permanent, secure, albeit low-paying job to start my own business. I did this in September 2009, mid-recession. I had a plan if the worst should happen, and my business failed, though things worked out a little better than okay.

A sale is not a sale until the money is in the bank – Part 1

Things worked out too well. On day one of the business, right out of the starting blocks, I made sales. Quite a few, to be honest, and this was all well and good until my suppliers started asking for payment, considering I was yet to be paid.

The term overtrading was something I learned about the hard way, and the business nearly went under in the first twenty weeks.

I’ve never been in debt personally, not once. But I can promise you that waking up in the middle of the night worrying about paying suppliers and getting payment from customers was one of the worst times of my life.

I didn’t sleep properly for nearly two months, and every waking minute I remained focused on this. It was draining and destructive. I wouldn’t wish it on anyone.

Thankfully, many of the first clients were friends and past business acquaintances. So, I was able to chat with them about tightening their payment terms. 

It’s incredible the lengths people will go to help you if you ask.

(Any new clients were on strict payment upfront until they established strong trading history. A practice we continue to this very day. I count this as one of the core reasons our cash flow was always great. I learned this lesson early on, albeit the hard way.)

If you don’t have the money in cash, you can’t afford it

My parents drummed this into me from the earliest days. It’s not that credit was evil; they wanted to instill the values of saving and spending wisely. To this day, I continue to practice this trait.

Every bit of capital expenditure in the business has been self-funded. Delaying the purchase of equipment and machinery has prompted us to give full consideration to every decision. The trade-off may have been quicker growth in the business, but I’m happy with how things turned out. When it’s your own money, and it matters to you, you’ll always make the right decision or make the wrong decision work.

Not getting into debt allowed us to weather any market downturn or quiet period. Many competitors who were debt leveraged are no longer in business.

Invest in yourself

I live and breathe the Japanese practice of continuous improvement. Striving to improve through continued, incremental changes in all aspects of my personal and business life has made me the person I am today.

I am smarter than I once was, a better listener than ever, and have knowledge of systems and programs I previously did not know. All because I have chosen to learn and develop these skills over the longest time. 

My goal was to make myself a happier person overall and to forge stronger relationships with those around me. Liken this to compound interest: You rarely see the benefit immediately, and often it feels like you aren’t progressing, but over a longer time horizon, you will achieve the goals you set for yourself and be able to observe the growth you have made.

Looking back at where I was in 2009 and comparing it to 2022, my knowledge and skills are leagues apart!

A sale is not a sale until the money is in the bank – Part 2

Selling your business is one of the most challenging tasks a business owner will endure. Selling your business in the middle of a pandemic is right up there with putting people on the moon. We did it, but not without challenge.

On the first attempt at selling, I was sitting in the solicitor’s office awaiting a call that we were to sign our documents. That call never came, but another did. The one that went around the world told us to go home from work, lock our doors and sign happy birthday twice while washing our hands.

Thanks, COVID-19!

Not only was the sale of the business off the table. We had to navigate a new era where many of our clients closed their doors, didn’t need our products or services and weren’t paying their bills.

Aside from the business element, I had forty staff looking to me for answers. Answers I did not have or was making up based on the scarce information I could find.

Our business paused for a total of two days during COVID. During that time, I am not ashamed to say that I walked the streets with tears in my eyes, trying to figure out what to do next. And the idea came for us to pivot into a new range of products immediately required due to COVID. It wasn’t enough to fully replace all the business we’d lost, but it kept the doors open, lights on, and a lot of people in jobs. 

We became the leading supplier for this type of product in the country and won several significant tenders on the back of that. It is hard to overstate the importance of being a creative thinker as a business owner. We had to face an enormous challenge we’d never encountered, and I’m incredibly proud of how my team and I responded to this.

Our prospective purchaser had kept an eye on these developments and observed our resilience to these world-altering events. Around September, the deal came back on the table, and we completed it at the end of November. 

Until the money reached the bank, I didn’t allow myself to celebrate.

Don’t wait for the big payday and forget to enjoy the journey!

I have business associates who describe their business as their pension. They live to the limit of their means but aren’t building or diversifying their wealth away from the company they own. If the worst happens to their business and profits fall, they’ll return to the starting point. 

During the past 13 years after I decided to start a business, I made the considered effort to become financially independent. Regularly saving 70-80% of my profits, I often remember declining events, trips, or holidays because I couldn’t “afford” them. This was the same day I’d likely deposited significant sums in my investments.

Early in my journey towards achieving financial independence, I forwent experiences, and I look back wishing I’d just gone on the trip or gone to the gig. Conversely, I’m here now, making up for it with a vengeance. So, potatoe, potato.

Want a pay increase? Start a business 

Before I decided to start a business, I never earned more than £20,000. Even in the UK and Ireland, this was below average. Working for myself provided me with the most significant jump in salary possible—a salary wholly determined by my actions and the profit I made. 

There were no such things as side hustles in 2009. You had a main job and a second or third job. The hustle culture wasn’t mainstream like today, and a fraction of the online resources were available. If I had to do it all over again, I’d start a side hustle and work evenings and weekends to get my business off the ground before leaping into self-employment. [Looking for side hustle ideas? Foundered has a great list located here.]

Live in your accounts 

When working toward financial freedom, it can be intoxicating to see the value of your investments go up.

Many look at their net worth daily and daydream about this growth over the long term. It’s fun to do, but because you are not in control, there’s little you can do, but add more funds, watch and wait.

Daily account checking provides little value day to day. 

However, within a business, being in control and on top of your accounts is something you control. Knowing how much your business has sold, what costs you incur, and how much profit you’ve made is critical to your business’s success and growth. As a driven and ambitious business owner, it serves as fuel to the fire, knowing that you are making money.

Alternatively, knowing your accounts inside and out explains the day to day and allows you to take appropriate action if you’re not making money.

There should never be any surprises in your finances as a business owner.


If you’ve ever debated on whether or not to start a business, go for it. But, plan for the worst and work to make the best possible outcome happen. It won’t be easy, and it won’t always be fun. There will be moments of sheer joy and moments of utter despair. Many of these moments revolve around money made and money spent in the company. Anyone who tells you otherwise is a big fat liar.

Focus on your finances first and foremost. These are the lifeblood of your company, regardless of size.

I promise you that no one has everything figured out. Don’t let that stop you. We each need to experience things and learn to grow and improve our knowledge and skills. Go ahead, get started on your business. You will become a different person for doing so.

And please don’t get into unnecessary debt. You’re robbing your future self.

Today’s guest post is part of my ongoing series where I bring in others to share their thoughts on personal finance. I hope you enjoyed it and please let me know your thoughts in the comments below. If you would like to write a guest post, please contact me! But, without further ado, let me introduce today’s author!

Author bio: Connor is the blogger and mind behind Foundered, a personal finance blog that shares his views, experiences, and more. Most importantly, he is a father, and someone who isn’t afraid to pursue his ambitions. He will retire at the young age of 40 this year. To learn more about him, you can read his blog here.

Mile High Finance Guy

finance demystified, one mountain at a time

mile high finance guy

3 thoughts on “Start A Business To Avoid Working Until 65”

  1. This was so vague….thought there’d be specifics, what business, what products, how the ideas were implemented, specific challenges (not just, “didn’t sleep for 2 months”), what determined the exit point, how was the sale negotiated and how investors were lined up, why decided to sell, what’s the plan for the next 40+ years….these vague “work hard, start a business, retire early” posts are useless in my opinion.

    1. Hey Bo,

      Thanks for reading and sharing your candid feedback. I will reach out to Connor to see if he will chime in to give more details. Going forward, I will take your thoughts into consideration and strive for more specifics when I have guest features.

      Olaf, the Mile High Finance Guy

    2. Hey Bo, I’ll answer what I can further. Some is under contract of non disclosure.

      My business was not for sale. We were approached by an M&A firm who’s client was looking to move into our market. That said though, we had made great strides to make ourselves known in that intermediary space over the 2-3 years previous. We were on the radar and had helped many of their businesses to grow. We had a great reputation, so it made things much easier.

      Sale negotiations are tough. Comes down to valuation of your business and then a slight arm wrestle around this (Up or Down). Ultimately both parties need to feel like they have gotten a deal. We were selling from a position of strength, so we wanted a fair value only. Not the earth, moon and stars.

      I’ve honestly no plans for the future. I spent a lot of time over the past few years considering this. I started a blog (cliche I know) and I’m trying to educate people I know about personal finance and saving in general. I’m an entrepreneur so I always look for opportunity in things. I’m also a builder of things. What form that takes is still to be determined. Right now, I’m spending time with my family and being present. It’s very rewarding.

      Happy to answer whatever I can here.

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