Asher's Blog

There is a version of leadership in startups people rarely talk about.

It is not the funding announcement.
It is not the celebratory team photo.
It is not the “we just hit record growth” milestone.

It is the quiet but intense moment. The version where you are sitting alone at 11:47pm staring at projections that are tighter than you hoped, knowing that payroll is due in days, a regulator just changed a policy, key execs exiting, a customer loan gone bad, and your team is looking to you for stability you are still trying to manufacture inside yourself.

That is where I have found myself more than once as a startup founder. They’ve been huge moments of reflections and I have gained useful scruples in those reflections. One of them is that extraordinary leadership is not revealed when things are normal, it is revealed in when there is a lot of constraints. 

The Myth of Smooth Growth

We often romanticise startup life as momentum stacked upon momentum, but research consistently tells a more sobering story. According to data frequently cited by Harvard Business Review, nearly 70% of change initiatives fail, not because the strategy is flawed, but because people cannot psychologically transition at the speed of execution. Strategy is rarely the primary issue. Human capacity under pressure is.

Similarly, startup data from CB Insights shows that one of the top reasons startups fail is not competition or technology but running out of cash, which is rarely just a financial problem; it is a leadership resilience problem. And it is not just on the founder or founding team, sometimes, I know key investors can help a startup founder navigate the challenging times. I really appreciate the model Kola Aina shows with his startups, that’s a model investor to follow. I haven’t been lucky to get him in any of my 2 startups but maybe I will later, who knows. My mentor, Parker C was not that lucky – he was sacked by his investors after a tough moment in his first startup but he went on to do a multi-billion dollar startup after that. 

Founders go through a lot of psychological warfare and it is more intensed when you don’t have the backing of your key investor or there is a co-founder split. These 2 events usually mark the end of a startup but in very rare circumstances, a founder can navigate it with resilience and a lot of patience – cos sometimes, the founder may need to allow the situation unfold before he starts picking up the fallen pieces. 

Pressure Does Not Build You. It Reveals You

For a long time, I believed pressure built character, but over the years I have come to agree more with the idea often attributed to leaders like Warren Buffett, who famously said, “Only when the tide goes out do you discover who’s been swimming naked.”

Pressure does not create a new version of you; it exposes the version that was already there. For instance, when you delve into personal insults and slam the door (virtually or physically) during intense or crucial conversations, that version of you is a reaction and it reveals more of who you are, rather than what caused it. So, 

• When revenue tightens, do you compromise standards to protect optics?
• When a customer defaults, do you bend discipline to preserve relationships?
• When a senior team member underperforms, do you delay the hard conversation because confrontation feels exhausting?
• When fear rises internally, do you transmit anxiety or transmit steadiness?

Extraordinary leadership is rarely about genius; it is about response. I have made mistakes in these areas but the good thing is realising it and not making these mistakes again.

The Founder’s Private Strain

There is a silent tension that founders carry that is rarely articulated publicly, which is the requirement to move decisively while still processing doubt internally.

• You must project conviction while privately wrestling uncertainty.
• You must inspire confidence while recalculating risk in your head.
• You must make decisions that affect families and livelihoods while managing your own emotional equilibrium.

I have initiated strategic changes quickly in the past: new products, pivots, restructures, and logically they were right decisions, but my body often took weeks to align with what my mind had already decided. That gap between intellectual clarity and emotional adjustment is real, and it can be destabilizing if ignored. As Angela Duckworth writes in her work on grit, sustained excellence is less about bursts of intensity and more about disciplined perseverance under long periods of difficulty. Extraordinary circumstances demand that kind of endurance.

What I Am Learning About Being Extraordinary

1. Slow Down Before You Speed Up

When pressure rises, urgency feels productive, but urgency without clarity multiplies error. So, in hard seasons, I now force myself to ask slower questions: What actually matters this week? What must not break? What is noise disguised as importance? That pause often prevents reactionary decisions that would compound the stress later.

Clarity under pressure becomes a strategic asset. Always Pause. One thing I have prioritised above everything else is being liquid, that is usually our first priority and everything fits into that goal. It helps us retain and multiply our leverage. You may try the same. 

2. Protect Standards When They Are Expensive

In extraordinary seasons, standards suddenly feel negotiable because survival feels urgent, but the moment you lower standards under pressure, you teach your people that standards are conditional.

When growth slows, the temptation to cut corners increases, whether in compliance, credit discipline, hiring, or communication. Yet it is precisely in those moments that discipline must tighten, not loosen.

As leadership thinker Jim Collins wrote in Good to Great, enduring companies preserve core values while stimulating progress. There would be a lot of temptations and the prayer, God do not lead us into temptation, is a real prayer. I went through a phase of temptation some time ago, and I’m thankful that it naturally failed. I have since built stamina to let it go whenever it comes back and I have repeatedly done that the 2 times it happened in the last few months. 

Remember, your standards are most valuable when they cost you something.

3. Regulate Energy Before You Regulate Others

Teams mirror leadership more than they listen to them.

• If I am reactive, the organization becomes reactive.
• If I am visibly unsettled, even without saying so, the room feels it.
• But, if I am calm but honest about difficulty, steadiness spreads.

Emotional contagion within teams is real; the emotional state of leaders significantly influences performance and morale. Extraordinary leadership does not mean pretending everything is fine. It means saying, “This is hard, but we are steady,” and embodying that steadiness consistently.

4. Think in Sequences, Not Reactions

Extraordinary circumstances require correct order of operations and fanatic discipline. When we didn’t achieve or exceed our target, it wasn’t because of incompetence. It was mainly because things were done out of order. You cannot do everything all at once, so you need to pre-determine what is important and help your team prioritise their goals and actions. 

You see, extraordinary circumstances expose disorder immediately because the margin for error shrinks. So, what I am saying is that sequence matters – strategy before speed. I have learnt that discipline compounds quietly, but disorder compounds faster.

5. Stay Anchored to Mission

In difficult seasons, fear grows louder and ego becomes fragile, but mission must become louder still.

When I reconnect with why we started, the people we intend to serve, the long-term impact we intend to create, the infrastructure we are building for the future, short-term volatility becomes easier to absorb. Vision stabilizes emotion, and extraordinary leadership requires emotional stability. When the mission is clear, it will be easy to be centered around it when the pressure is high but you have to pause. It is during the Pause moments that you gain centrality afresh. 

The Invitation

If you are in an extraordinary season right now, whether in business, leadership, or life, it is not an indictment; it is an invitation.

An invitation to elevate standards.
An invitation to deepen discipline.
An invitation to regulate emotion.
An invitation to lead beyond instinct.

It is an opportunity for an extraordinary great outcome.

I wish you well