Resilience and Leadership

How to keep ahead in business when the going gets tough

Just over 17 years ago I sat face to face with a co-founder. The money had run out, the business was burning through a high monthly wage bill and income was just four figures a month. Everything seemed doomed. The first major product launch had been well received but failed financially. Many people lost their jobs, the company pivoted but never recovered to the dizzy valuations it had enjoyed just months prior.

The CEO was ousted from the very company he’d founded. Exhausted and burnt out he mustered up his last reserves of energy and began a new project. At first it was just an idea that rested on a domain name. It took shape and 17 years later his new company is worth over $2B.

I have seen (and also experienced first hand) the struggle of founding a company, trying to get the market to value the output, trying to make sales and failing, time and time again. Behind every successful company are often innumerable stories of ‘to the brink of failure’ or conflict, despair and a level of sheer effort and grind that sometimes makes you question your own reality. Indeed, Nvidia co-founder said he’d opt out if he had the chance on ‘doing it again’. So what IS it that propels people to the successes that we read about all the time online or even in movies?


From startups to large corporations

No more so does resilience in leadership manifest itself than in the crazy world of startups. I’ve seen fist fights, tears, elation, exits, all of it. Somewhere within all of that lies a founder or leader that manages to rise above all of it and keep going. Few tales resonate more strongly with entrepreneurial resilience than that of Airbnb during the COVID pandemic. Net losses hit over $400M from 2017 to 2019. Brian Chesky, founder and CEO of Airbnb turned the crisis into an incredible rebound. The business dropped 80%, the IPO was put on hold – how could Airbnb possibly succeed?

Chesky’s resilience meant he kept a cool and strategic head even in such awful conditions. Airbnb quickly implemented a blanket refund policy and last-minute cancellations to allay people’s fears of travel (caused by COVID). They laid off staff, refocussed on their core offering, produced a special enhanced cleaning badge for adhering hosts and dug deep into their customer’s emotions around stays.  Furthermore the way in which Airbnb treated those employees it laid off was praised by the industry. In 2020 Airbnb’s IPO was one of the largest IPOs of the year, valuing the company at $47B. A remarkable turnaround.

In a similar way we can look to a larger company with Microsoft. In the corporate landscape, Microsoft’s journey under the leadership of Satya Nadella serves as a beacon of resilience. Faced with the decline of desktop computing and the rise of mobile devices, Microsoft struggled to adapt in the early 2000s. However, Nadella’s strategic vision and resilience came to the fore when he led the company to focus on cloud services and subscription models. This bold pivot revitalised Microsoft, positioning it as a dominant force in the tech industry once again.

Agile Leadership – Adapting Swiftly to Change

The essence of resilience in the entrepreneurial journey often lies in embracing agile principles. The ability to break down complex challenges into manageable tasks and iterate rapidly based on feedback is exemplified by successful founders. Examining Chesky’s methodical approach to the company’s turnaround you can see the quick insights from their customers morph into real-world products that made a big impact. 


People, emotions and empathy


Contrary to the perception that businesses should force employees to work insane hours and burn out for success you’ll often find visionary leaders advocate for the opposite. They way in which Airbnb CEO Brian Chesky cared for the workers that he had to lay off shows a huge empathetic understanding. Similarly Nadella at Microsoft believes in a strong work/life balance and introduced ‘OneWeek’ where employees are encouraged to take time off to focus on their own projects and interests.

A Daily Routine


But what builds resilience? How do these celebrate visionaries do it? There are some common threads. Routine seems to be one of them, as does exercise or hitting the gym. This Inc. article provides a great list of things that many founders and CEOs have done to keep building their resilience.

How to build your own resilience

1 Lean into yourself

Accept your situation. By developing a self care mentality you become able to lead without losing it. You’ll feel calm in situations where others may panic. By accepting who we are and learning to be kind to yourself you make it easier to deflect incoming noise, drama, stress and are able to make the right decisions at the right time

2 Build your routine and stick to it

There is never a ‘done’ in life. So once you get that construct a routine of good habits and keep going. This will serve you well. Routine means structure, discipline and results over time. When things get tough you’ve always got your routine to keep you going.

3 Work out

I’ve been through complex neurosurgery, many failed ventures and some successes. I can honestly say that lifting weights most days has been instrumental in building my resilience. You’ll also be surrounded by like-minded people who will encourage you to do better. Often daily. Build in an exercise program into your routine.

4 Eat well and be healthy

Obvious but eating junk and boozing heavily will make you lethargic and feel crap. When stress hits and you need to call on your inner reserved of mental and physical strength your diet will prepare you well. Again, incorporate healthy eating into your daily routine. Results at the gym or exercise are largely dependent on diet.

5 Learn, Daily

You don’t know it all. No one does or ever will. Keep your mind active by being curious. Learning new skills, reading new stories about successful founders or businesses or even learning how to do latte art will keep fuelling your brain with thoughts and ideas.

6 Lead by example

Be on time, try to be presentable. Don’t lose your shit too much. Jump on things however small to show you care. I cannot stress how much impact a founder or leader can have by getting in there with the team, ideating on something, doing something that the team wouldn’t expect. Go all in.

7 Ask

Steve Jobs called it here. If you don’t ask you’ll never get. Whether it is for investment or just a question about an idea. Don’t ever be afraid to ask as you leave opportunity on the table.

8 Be kind

What matters to you? Do you think your team will remember reaching their OKRs for Q4? Or nailing that one launch that you held a deadline over their head for? Nope. People will remember gestures, experiences, the times you listened and cared and treated them with respect. So be kind, if anything at all.