Jeraldene Menon
In the start-up culture everyone talks about building for scale, where the unicorns, loud wins and exits are celebrated.
Understandably, the most noteworthy entrepreneurs are the most enduring, the stayers; they tend to build their businesses up with strategy and a quiet determination. Dale Simons, founder and CEO of the MiDO Group, and the Stellenbosch Network’s Entrepreneur of the Month in July, happens to be one.
Based in Jamestown on the outskirts of the town, where he was also raised, his family cultivated strawberries and grew vegetables there. Simons’ parents were deeply involved in ministry and community building, values that shaped his vision from an early age.
This “quiet entrepreneur” remains a proud Jamestowner. After studying mechanical engineering and working in both project management and IT he decided to pursue a different path.
What started as a way to solve technical problems and manage IT projects evolved into something much bigger: connecting young people to meaningful digital careers. Over more than a decade Simons has built the MiDO Group, an integrated “digital ecosystem” with three distinct entities – MiDO Technologies (work-integrated learning and digital internships, 2012), MiDO Foundation (digital awareness and tech access for school learners, 2018) and MiDO Academy (accredited learnerships and cybersecurity pathways for post-matric youth, 2023).
Each addresses a different stage of the youth’s journey, from early awareness to real-world employment. “I started by solving technical problems,” Simons related. “It has since evolved into creating employable digital pathways for youth.”
Alongside co-founder Anna Collard, and with support from the UK’s Foreign Commonwealth & Development Office Africa Cyber Programme, he launched the MiDO Academy in response to two urgent challenges – the global shortage of cybersecurity professionals and local crisis of youth unemployment.
Today the MiDO Group works with partners such as Amazon Web Services (AWS), Stellenbosch University, The Sanlam Group and KnowBe4 Africa, yet remains firmly rooted in Stellenbosch.
Internally the team operates on a simple but powerful philosophy. “We focus on good stewardship, great systems, creativity and innovation,” Simons pointed out. “We believe in building smart and healthy teams.”
Before MiDO materialised he spent years in the information and communication technology (ICT) space, as ICT director at Spier Holdings and an ICT consultant at Pragma Africa.
In addition to his mechanical-engineering qualification Simons also holds an executive-development qualification from the Stellenbosch Business School, and became a Microsoft Certified Solutions Associate in 2003.
Armed with such technical and leadership credentials he is now focused on helping young people navigate the Fourth Industrial Revolution through access, education and real opportunity.
Next, MiDO will launch a new online cybersecurity-training platform in partnership with BeeLine. They are also working on a frontline support system for victims of cybercrime in partnership with AWS, Cyberhelpline UK Ciso Alliance, Vizstrat and others.
Even with global reach Simons keeps his mission local, having built a company that reflects his town, a place of care, consistency and quiet impact. His advice to other entrepreneurs? Stay the course.
“Entrepreneurship is an exciting, terrifying and rewarding journey demanding much. Start with personal growth and development, then go to knowledge and systems. Failing is part of the journey; get used to it! Practise gratitude daily.”





