Balancing the Grind with Caleb Holstein, Co-Founder at greensquare

Caleb Holstein is the Co-Founder at greensquare, a multi trader green coffee trading and management platform built to elevate the coffee trade into the digital era.

Let’s start with your background! Can you share with us your career journey and what you’re currently up to?

Growing up in the back of my parent’s businesses on the central coast of NSW just north of Sydney unaware to me but my entrepreneurial spirit was being cultivated in the days spent watching, learning, and living the business owner life from hours before and afterschool spent with my parents and older siblings in the business.

So naturally at the age of 14 when my older siblings had organised vendor finance from my Mum for the small cafe she had owned for the past 2 years I was lucky enough to join them and become an owner of my first-ever business.

If I am honest at that age the opportunity was lost on me and I did not know how lucky I was to have this experience and to have my family and older siblings share this journey with me until years down the line when I was owning and operating my own businesses in my early twenties realising the unconventional and unique education I was given from my family.

Helping me build a robust work ethic, personal confidence, and most importantly self-awareness which have become crucial as my career has developed over the years. 

We’d love to know what a typical day is like for you. Could you describe a recent workday?

A typical day for me is:

  • 5am: Wake up, I take the dog for a walk or run depending on how we are both feeling
  • 6am: Stop into my wife’s post-dog walk for a coffee and chat (honestly the best part of my day)
  • 7am: Head back home and get set for the day (I work from home mainly)
  • 8am: Morning meeting with My Co-founder and review each of our days ahead along with handling all handovers that have come in overnight from my co-founders based in Germany, reply and follow up to 
  • 9am-12pm: Usually consists of a few meetings with clients ( Coffee Roasters or importers) along with planning or shooting some education/support or content.
  • 1pm-3pm: If no meetings (which isn’t common) afternoons are for planning be it fundraising docs or meetings, user support sessions, optimisation tips for users, or even events/ media interviews we have upcoming.
  • 4pm-5pm: Email wrap-up end-of-day platform/software check and review. See the activity for the day and see if there is anything we need to address or follow up for users along with summarising the day and meeting notes.
  • 6pm-7pm: Germany wakes up. Almost every weekday I finish my day with a call to my co-founder and our COO Jan who lives in Berlin, Germany. Honestly, the best way to wrap up my day and I like to think it is a great way for him to start his day.

Can you define work-life balance for yourself and share with us your approach in maintaining it?

I think this is personally one of my biggest challenges. Previously I had gotten this completely wrong and it directly affected my personal mental and physical health along with my relationships both personal and business-wise.

But having gone through this and realising that I needed to address this when starting SquareX and greensquare, it was at the forefront of how I want to set up the project from my side and how I want to provide myself with the framework to be successful in a sustainable way.

I would be lying if I said I am nailing it every day because I always love overworking but I feel I am a lot more self-aware about striving for balance and a lot more forgiving to myself when I do need time to wind down or switch off.

I feel I naturally have a very good work ethic and strive which has been amazing to help me achieve my goals but seeing burnout coming and knowing when I need to take a break has always been a weak spot but this is now the goal to learn this skill set and allow myself to thrive in a more sustainable way.

Change is constant, and it’s essential for growth. Have you made any lifestyle changes in the past year to improve your work-life balance?

Yeah my previous business was a Communal Coffee Facility which was based a 1:45 min drive from my home and I spent 3 ½ years driving there and back 5 days a week working 14+ hour days and achieving some amazing things but realising the way I was working was not sustainable. Taking on way too much work across the business and trying to be the guy who does it all.

So when co-founding SquareX and greensquare I was determined to surround myself with an amazing team and structure my workflow to be a sustainable approach that allows me to thrive in my own skills and allow me to create a space for others to do the same.

We’re always on the lookout for new resources! Can you recommend any books, podcasts, or newsletters that have helped you in your journey towards balance?

For me, this was my first entry into the start-up world, and found it to be a pretty intimidating and cliquey space, to be honest, but the funny business podcasts from Rob and Lach at the Dream Big Social club were awesome. Such good content helped me find my community and people in the startup world. Also, another great podcast that was actually recommended by a mate that has helped me a lot is The Imperfects.

Before we wrap up, do you have any final words of wisdom or insights on work, life, or balance that you’d like to share with our readers?

This is my personal little mantra but it helps me to know I am moving in the right direction when checking all these boxes. Be sure to be and surround yourself with good people, doing good things for good reasons.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.