The Scariest Decision of My Career

Happy Friday Friends,

I’ve made the scariest decision of my 20+ year career.

Before you get to the juicy details let me give you a brief background.

I studied design, advertising and communications at university in South Africa. I chose this route because I thought I wasn’t smart enough to handle a business degree. I was also very creative and got an A+ for art and design in high school. In my last year of university, I spent 3 months in an ad agency and hated every single second. I knew I couldn’t face this as a career. So, I discarded everything I’d spent 4 years studying and fell into managing restaurants for a few years. To this day it was some of the best “education” I’ve ever received.

That led me to start a “Restaurant Tech” startup. Importing products and services for hospitality to South Africa. I was inexperienced, and too early to market, so we failed. But it led me to my next opportunities. After building a successful water purification franchise for 2 years I decided to leave SA and move to London. I knew I needed to leave South Africa but I hardly knew anyone in London. Also worth mentioning this was Jan 2009. Splat, bang in the middle of the GFC (Global Financial Crisis). People told me I was mad to leave what I’d built and take the risk of emigrating. But I did. And, then spent the 6+ years working in online gaming and casinos. I travelled the world, it was awesome.

I’d almost earned myself UK citizenship, built a group of close friends and had a pretty decent network in London. But, again I decided life was too easy and to take a more challenging path and emigrate. Again - this time to Australia. I gave up almost a decade of experience in an industry for a new country with new experiences waiting for me. It took time to find my feet and to find a career path that would excite me. I discovered tech and startups. I fell in love.

I spent the next 8+ years working in tech startups. Gaining experience in all the areas needed to start and scale a successful tech company with the hope of leading one. I’m "lucky" in that I’ve been headhunted a few times which allowed me to progress while learning about different industries. 

To be honest with myself; I was chasing a C-suite role. And then I got the chance in August 2021. For the past 18 months, I’ve been the CEO of a SaaS tech startup servicing hospitality clients in Australia. When I accepted the job I convinced myself this was my medium-long term path. I could finally settle down.

I helped rescue and then grow the business. But, after spending time as a startup CEO, I realised that a title I’d been chasing for years didn’t mean anything to me. I came to see that the C-suite in any startup is not as glamorous or as profitable as the media hype would have you believe. A CEO and founder warned me before I started; “CEO in a startup really stands for Chief Everything Officer”. 

The biggest surprise though was that I still wasn’t my own boss. I still, didn’t own my time. I still had to answer to investors and board members who gave orders without any experience. 

I proved to myself I could do the hard things. I could run a small team, raise capital, grow revenue and drive towards profitability.

Here’s a short list of what I helped achieve at Wirely.

• Raised a pre-seed funding round of $1M+ 

• Achieved $1M ARR milestone in less than 12 months

• Grew revenue by 4x 

• Improved cash burn by over 50%

• Improved average contract value by 25%

• Improved cost of acquisition by 5x

• Improved onboarding times by 300%

• Improved time to first value by 100%

So, after careful consideration of what puts fire in my belly, I decided I didn’t want to be the CEO of a startup. At the end of the day, I was investing all my time, and more importantly my emotional energy in someone else's baby. I decided to step away from the business and hand it over to the founder. 

I needed to do some serious thinking. Who wouldn’t want to be a CEO, especially when the business is growing? I asked myself some tough questions.

And, after some deep soul-diving, I realised that I’ve always hoped and depended on other people to create the “big” opportunities for me. I networked and found mentors with the hope they would give me a once-in-a-lifetime opportunity. Or, introduce me to the business that would be the next unicorn. It’s now time to stop hoping for someone to come save me. No one is coming to save any of us. It’s all on me now.

So What’s Next?I am going to take 20 years of entrepreneurship, tech and business experience and focus on helping others improve and scale their businesses. I love coaching and I love getting scrappy to figure out business inefficiencies. I am starting a business consultancy and offering my services as a fractional COO (Chief Operations Officer).

I have done bits of consulting here and there over the years. I’ve helped a few founders develop their Customer Success and Retention orgs. But, this is different. I did those as small side gigs, not for the money but because I like helping people and solving problems. Now, I need to sell my experience and my services. And, I need to build a portfolio of clients so I can support my family. I am starting a startup. 

My heart rate increases by saying that sentence out loud. It is terrifying that it all now sits with me. I have to create this future and do all the things needed. Alone for now.

But, when I talk to people about my decision I get more excited than I have for years. I am confident I have the knowledge and experience to make a success of this. I just need to quiet my inner voice and back myself.

Life is short and you only live it once. 

What Does This Mean for The Weekly Feels?For now, I will continue writing Weekly Feels posts because I love writing in this form. But, to build a business I will need to write more business-focused content. My goal is to build a following by writing a newsletter for startups and business owners on how to optimise different parts of their business. This writing plus networking should then lead me to customers who need help optimising and scaling their business.

How Can You Help?I’m so glad you asked.To get my first clients I am tapping my network for help. Yes, that means you.

I'm offering guidance to tech companies hitting the scaling phase. If you know a founder, CEO or team who is finding the scaling phase a real challenge, I would appreciate an introduction.

You can reply to this post or email directly jarrenp[at]strivelab.xyz If you’d like to check out my website it’s Strive Consulting. All feedback is welcome.

I appreciate all of you and thank you for the ongoing support.

Exciting 2024 ahead!

Peace, love and muscles.Jarren

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A Pic From My Camera Roll