Growing up and maturing – An Entrepreneurs Story


Now, at the beginning of 2018, with our political climate looking up and the dollar at under R12, one entrepreneur is filled with a new hope and inspiration for the future. The theme for this year is to scale, build and grow – if you have the seed, sunshine and water the f*** out of it!

Henry works as a developer specialising in websites, web applications and mobile apps in his business, Web Ink.

To give some context to his journey, let him give you some background. ‘I had decided to become a web designer in October 2008 during my time as an English teacher, teaching basic English and business English to adults at a school in Braamfontein. The epiphany I had was that I really enjoyed the teaching itself but English as content was not very stimulating for me. I had always been interested in IT and so I decided to become an IT trainer. The only obstacle being that I had no real teachable knowledge in IT and so began the steady climb to becoming a working professional to gain the skills in order to one day teach!

As a kid, I never went out on weekends and rather stayed at home on my dad’s laptop learning Turbo Pascal and DOS programming for the pure fun of it – I could not get enough of the learning, a passion which is still with me today. The partying came much later on!


I started Web Ink, officially, on the 1st May 2010, the day I stepped out of a 3 month stay in rehab (a story for another day). Knowing absolutely nothing about web design or development, in fact I had only built my first HTML web page using Dreamweaver in 2009. This speaks to my nature which is clearly very stubborn, impulsive, reckless… and passionate, when I find something I love.

The first 3 years were very tough, I mostly lived on Jungle oats and was mostly broke – taking any opportunity to build a website for anyone who would have me and for really cheap. Having zero business schooling either, I was really just winging it, taking each day as it came and intuitively navigating my way along. With no real plan, I have stayed on survival mode right up until around 2015, which is when I started to actually think about what I am doing with Web Ink and this was sparked by the realisation that I was getting tired of just churning out one project after the next with no growth. The lesson here being that you will get what you aim for.


Bright eyed and bushy tailed… also no clue! Doing website design, development and SEO for next to Nada


Decided to focus on and become a WordPress specialist developer


Left my bedroom to rent my first real desk in an office


Took on my first business partner in order to leverage his network – didn’t work out


Had my first experience in a coworking space


Formed Fat Possum, which was my second attempt with a business partner who was a graphic designer;

Narrowed my focus to become a pure developer – leave the design and digital marketing to collaborators

Built my first mobile apps and first software applications


Broke up my business partnership with the graphic designer and took full ownership of Fat Possum, closed office and retrenched our one employee


Rented a desk at Impello – a coworking space in Greenside


Going right back to square-one in terms of infrastructure, the theme for me in 2017 was re-inventing the brand, getting back to basics and rebuilding my identity on both personal and business levels. Being at Impello really lit a fire under this process, giving me access to other professionals and entrepreneurs in my immediate environment (some more, some less experienced than me and all with a different story).

I was bombarded with the intensity of the entrepreneur jargon and clichés… attending many talks, events and other networking events with an overload of exposure to industry professionals; Leaving me with an incredible amount of pressure to be successful, find my ‘why’ and basically wake up to my vision and mission and if I didn’t have one to find one real quick!  The result and sum of 2017 for me was the long-awaited revelation of my ‘elevator pitch’ which I basically woke up to on Friday 19 January, 2018:

“We emphasise strategy and planning in building sustainable solutions to empower progressive businesses.”

The feeling of release when I read the statement above is IMMENSE – bathed in ecstasy, in that instant, everything became clear to me. I now have a very clear vision and mission of my brand, who it is and what it does.

For Web Ink and Henry, 2018 is about growing up and maturing.

The business priorities right now are:

  1. Income to fuel growth
  2. Sustainability and business expansion
  3. Optimisation and iteration to offer value and efficiencies


  1. You don’t need a business partner – if you take on a partner, do so logically and for good reason. Also, be very clear about expectations and give each partner a share based on the value they will bring; And draw up specific contracts at the outset.
  2. If you are a freelancer, get into a coworking space – this gives you an invaluable opportunity to network, get exposed to new ideas and to get out of your own head.
  3. Set goals and have a plan
  4. Set aside a regular time to work on your own business, eg. Every Wednesday for me is ‘Web Ink Wednesday’ – come hell or high water, this day is my sacred day to do work only on Web Ink.

Thanks for letting Henry share and please feel free to get in touch with him if you resonate with any of the above and want to get a coffee or if you have some capital you want to turn into the next big app!

Written by Henry Shepherdson of Web Ink –