Why Founders are Optimising for the Wrong Game

As a recovering serial founder myself, I know the brighter and darker sides of entrepreneurship. It’s exhilarating being a founder. Falling in love with an idea, and seeing it come into the world, is a joy that few other experiences can hope to replicate.  But in the adrenaline rush, it’s easy to lose sight of the bigger picture – and to optimise for the wrong game. That leads founders to lose their own sense of authenticity, boldness and distinctiveness – and everything from chasing funding to the best team mates.  The right game, from my experience supporting over fifty founders in every conceivable sector, is about founder legacy.

I define founder legacy as the mark a Founder leaves on the world – right now, for the years to come, and for future generations. Legacy-driven entrepreneurship is all about being intentional about what that mark is.  Legacy should be intentional, not accidental. Founders in most organisations are not thinking sufficiently about how they can create an enduring legacy for the next and future generations. Futureproofing legacy will be critical to a founder’s external success – particularly in ensuring that their products, services, products or programmes are relevant to the needs of new generations.

Legacy-driven entrepreneurship involves:

1. Recognising when you are at an Inflection Moment
There are times in an entrepreneurial journey when it is really important to step back. These inflection moments could include a new funding round, significant team or board changes, or changes in the market landscape, technology or regulatory conditions.  For example, a med tech founder I was advising was able to raise a much larger funding round by being able to evolve their product to allow for changes in AI.

2. Articulating a really unique perspective on the problem you are addressing
It’s tempting as a founder to fall in love with our own mousetrap – our own product, solution or service. But the best founders are deeply in love with the wider problem, and remain open about the best way to address it. A Perspective Statement helps articulate how a founder sees the world differently from others in their sector. It becomes the key mechanism to attract the very best people, investors and board members around a founder. 

When I founded my education organisation (which scaled to 50,000 schools and 20m children), I thought the main issue was a lack of motivation among teachers (who were facing a very challenging system), not a lack of technical training. That helped me to raise $30m in funding by taking a very different approach to others in the sector.  It’s tempting as a founder to chase where the money is. But then you become like everyone else. Instead, the more contrarian you are in your Perspective, the more likely you will be able to leave a real legacy in the longer-term. 

3. Falling in love with the problem, not your solution
The best founders I have worked with combine conviction (which is essential to bring people along) with openness and flexibility to refine and adapt their solution to what they learn about the problem. When I advised the B-Corp movement, they were already very successful with their certification model and service, with the combined revenue of their member businesses reaching 3% of UK GDP. But to get to the next level of growth, they had to adapt their strategy to work more deeply with regulators, pension funds and government. They realised that the market had evolved – which they had contributed to! They now needed to evolve their offering with it to continue to be leaders in the sector. 

4. Building your solution and organisation with the next generation
Legacy cannot be created top-down. It needs to be co-created between generations in specific organisational contexts as well as with wider sector and societal trends (e.g., AI). It’s only through this generational co-creation that the challenge can be met. A whole set of founder-led disruptor organisations will emerge that explicitly focus on making next-gen lives better. If the incumbents and legacy organisations can collaborate in wider systems, they can redefine and futureproof entire systems together. I have been helping a Michelin-starred leading founder-led restaurant group evolve its offering to allow for the needs of a younger workforce and customer base.

5. Discarding old leadership “baggage” to face this generational inflection moment
Founders often compartmentalise professional and personal success and lives, but in truth, they are deeply interrelated, e.g., it may be an adult child’s struggles to get into an AI-jittery job market that inspires a Founder to think more consciously about Legacy, as much as the feedback from his / her Gen Z workforce. Similarly, it can be unhelpful to separate the needs of a new generation of customers/clients/citizens from those of employers and internal stakeholders. Both will have knock-on effects on the other. It’s critical to think holistically as a founder about the legacy you want to leave – not just within your organisation but in your life more broadly. 

6. Founders need to deepen cross-generational understanding & collaboration
Right now, we see Generational Inertia with Gen Z workforces quietly quitting, while founders are often quiet leading, i.e., they are being transactional in how they deal with younger generations. Founders need to help both generations understand and accept Generational Difference – particularly the key dimensions of Perspective, Authenticity, Connection and Excellence (PACE).  Founders also need to develop new frameworks, tools, processes and most of all Safe Safes to help different generations within organisations and societies move from inertia to legacy – through overcoming dissonance, experimenting, accelerating and then finally defining and building legacy together. If they can do that, they can retain an ongoing competitive edge and really be authentic, bold and distinctive in their sectors. Legacy-driven entrepreneurship is a journey, not a fixed destination. Its definition will continually evolve with how a founder sees their problem, and with the needs of new generations. It’s a much less “paint-by-numbers” approach to entrepreneurship, but much more likely to lead to founder fulfilment and success. Being a successful founder is not just about playing a game well. It’s about defining the right game to play in the first place.