Lessons from Failed Entrepreneurial Ventures

Entrepreneurship is often celebrated as a story of resilience, innovation, and eventual triumph. Yet, some of the most critical lessons do not come from the ventures that succeed, but rather from those that do not. In my journey, I have had the privilege of working with business leaders across Africa, and one truth repeats itself: Failure is not the opposite of success; it is part of it.

Two of my own early ventures – one in video retail and the other in professional photography – failed in commercial terms. But the more I reflect on the experiences, the more I realise how significant the learnings were in shaping the work that I do today, particularly in guiding boards and leaders of family and private companies because those failures taught me important fundamental truths.

Venture #1: The Video Store that Needed more than a Visit-a-Day Owner 

In 2006, I purchased a Stax Video rental franchise. The logic felt sound at the time: There was steady consumer demand, recurring rentals, and an opportunity to be an investor rather than a hands-on operator, and I love movies. What I underestimated was the complexity and time needed to run a seemingly simple retail business.

Margins were thin, competition from DStv and improving internet access was growing, and the model required trustworthy, highly engaged staff, which I struggled to find. I had assumed I could check in once a day, but the business required control, oversight, and operational discipline.

After investing in a store refurbishment and new stock, revenue improved, but not enough to make a consistent profit. After much trial and error I found an honest, committed shop manager and I started to feel hopeful that we could turn the business around and that he could become a partner, but he tragically passed away unexpectedly. Without him, the operational strain and losses returned, and I decide to exit and eventually sold the store back to the franchisor for less than the value of the stock. Soon after, streaming services accelerated the decline of video shops globally and within three years the new owner had closed the store completely.

Looking back, the failure was both operational and strategic. The business model was on the wrong side of history, margins and management requirements were misaligned, and my desired role as an investor clashed with the reality of hands-on retail leadership.

Lessons I took with me:

• Finding the right leadership is critical, but the business model needs to be able to afford the calibre of leadership that is required.
• Disruption does not arrive suddenly; it signals itself. We just do not always want to hear it.
• Shareholder and manager are different hats and often conflict. Committing to one and then setting up the business accordingly is key (Craft versus Enterprise).

Venture #2: When Turning a Passion into a Business Risks Killing the Passion

Some years later, while working in financial services, I faced a different kind of challenge – not operational, but internal. I was bored. I craved creativity and meaning. Photography had always inspired me, so I explored becoming a professional photographer with the goal of eventually replacing my salary.

This time, I approached the idea with thorough research and experimentation. I tested almost every revenue stream I could: weddings, family shoots, wildlife and landscape photography, magazine submissions, stock image platforms, auctions, even international competitions. I spoke to professionals whose work I admired to understand the realities behind the glamour.

I proved to myself that one could make a respectable income. But the work that paid – weddings, family portraits, fashion, food, corporate headshots – was not the work that fuelled my soul. And most of those who did specialise in the photography I loved, confessed that taking beautiful pictures was not what paid the bills.

The lesson was deeply personal:
A viable business that demands you to abandon the very thing you love is not a business that will sustain you. Passion alone is not enough. Profit alone is not enough. The intersection of purpose and commercial model matters.

Failure as Strategic Data, Not Personal Defeat

Both ventures failed commercially, but they gave me clarity that ultimately led to co-founding Sirdar. Today, I have found the variety, creativity and meaning that I craved and have the privilege of chairing and advising boards, helping entrepreneurial leaders scale with stronger governance, and – importantly – traveling across Africa, where I continue to take photographs in extraordinary places. The life I was trying to shape through photography emerged through a different business entirely.

My takeaways for fellow entrepreneurs, directors, and founders:

• Know which hat you are wearing: Shareholder, director, or manager. Confusion destroys value.
• Validate the management economics: Find ways for the business to afford the leadership quality it needs. An advisory panel, or non-executive directors, are great options to consider.
• Interrogate purpose early: If success means that you’ll resent the work, rethink the design.
• Study disruption in your industry: Denial is expensive.
• Exit is not failure: Sometimes it is the most strategic decision you can make.

A Closing Thought

Not every venture will succeed. Nor should it. Some businesses exist to teach us who we are, what energises us, and where we can serve at our highest level. Mine did exactly that – and I am grateful for the lessons.

If you are sitting with a venture that feels heavy, misaligned or structurally unsound, perhaps the most courageous step is not holding on to what you have, but stepping forward into a new beginning. The title of Marshall Goldsmith’s book comes to mind, “What Got You Here Won’t Get You There”.

Image: © Designer491 from Getty Images via Canva.com