How being irrationally ambitious led to the $26.2 billion sale of LinkedIn
Perspective that could change your outlook on the future
Abstract
Returning from holiday, I had just retrieved the luggage from my first transit flight and got my first few bars of free airport Wi-Fi.
I would only be at the airport for a couple of hours and so I had a choice to make.
Listening to music or listening to a podcast?
I deliberated and decided I had sufficient cognitive ability to listen to another podcast and so as a frequent listener of ‘Diary of a CEO’, my default was to explore what has recently been released.
Stumbling upon a rare business-based conversation with Reid Hoffman, one of the co-founders of LinkedIn, I was pleasantly surprised and saw immense potential in the almost 3-hour episode.
I listened to the first half while waiting to hear the gate announcement for the final plane back with the sole intention of having something to listen to in the background.
When describing the traits of an entrepreneur based on his experience, Reid Hoffman mentioned the phrase ‘irrationally ambitious’ and the ideas in my mind started firing.
Upon hearing it I thought: ‘You could apply that to exams and life in general’, to which I then replayed the point multiple times.
Now back at university, I decided to listen to the podcast once again, this time watching it on YouTube.
I picked up 3 key points I believe extended the theme of ‘irrational ambition’ and have the ability to change our outlook on what the future holds for us.
Discussion
This episode inspired deep introspection into what it means to be ambitious.
In the context of Reid Hoffman, being ambitious was having a vision, being prepared to state his case, and being unafraid to accept that the ‘smart’ people doubting his vision may be right.
He reiterated the point that the competition for his idea was small due to the overt risks that building a social network like LinkedIn presented.
Fears of employees seeming disloyal to their employers and the dependency on having active users in order for utility of the platform to be maximised both casted major doubts on the platform.
Nonetheless, Hoffman highlighted that if everyone thinks your idea is a good idea, it is probably not a big idea.
It was this way of thinking and framing contrarian beliefs that I found interesting.
The awareness that something is probably unlikely to happen but maintaining that belief and hope that the result you desire will come true, and if it does, the possibilities are endless.
Upon reflection, the times I had been irrationally ambitious where in moments where I felt I only had one shot at something - recognising that my circumstances had bred an opportunity that may not arise again.
Due to this, there were specific points from the podcast that resonated with me and attested to the idea of irrational ambition.
Have a 2 to 3 year plan instead of a life roadmap
A tendency that Steven Bartlett drew out from Hoffman was his ability to consistently be successful in predicting what the future holds.
Hoffman isn’t only a co-founder of LinkedIn.
Alongside being an author and running a podcast today, he has amassed substantial wealth from being an angel investor.
He was a part of the ‘PayPal Mafia’; a concentrated talent network which included Elon Musk and birthed companies such as YouTube and Reddit.
After PayPal’s sale to eBay, Reid invested into a range of startups such as Facebook and Airbnb.
He exemplified irrational ambition through his investment in Airbnb. Even when it was touted to fail, he maintained belief and recognised the exponential growth potential it possesses.
This has led to him amassing a net worth of $2.6bn as of January 2025 according to Forbes.
But when asked what he wanted to be when he was older, his response would be anything other than a lawyer, which was the job that both his parents had. Even today, there is ambiguity over what the future holds and what the next move is.
It’s fascinating, but not surprising.
On one hand, you may argue that being in an environment where tech was known to be the next big thing as well as having the network enabled him to assimilate to his surroundings.
After all, investments have their risks and much is left to chance, to which you can say it is impossible to predict success.
For that reason, is there any point predicting exactly what the future holds or is it better to focus on what you can do now to steer the uncertainty of the future in a direction you wish?
The extent of planning that Hoffman described was having a 2 to 3 year plan, which has been a key feature throughout his life.
Personally, the degree at which I plan is determined by the level of assurance I can have over the consequences of my actions today.
What this means is not hyperfixating on results today, but acknowledging the foundation my actions may lay for tomorrow.
As a result, self-awareness is a major factor alongside my ambitions where I too create mini life plans instead of planning for the unforeseeable future.
Arguably having this type of planning/way of framing the future prevents falling into the illusion of ‘having time’.
Although I do have long-term goals, they serve as purpose behind my actions today.
I use goals loosely, as they are more so frameworks for what I aspire to, rather than fixed milestones I am working towards.
Due to this, focusing on the next 2 to 3 years or so has consistently forced me to reflect on my current position and to acknowledge the power of what I can do now; a feature of my life since I was 16.
It’s funny how I processed the idea of irrational ambition - somehow I’ve ended up with reasonable and irrational in the same sentence but here it goes.
In a sense, having a 2 to 3 year plan is a reasonable scope to be irrationally ambitious as your ability to predict what is next would be far better than a 5 to 10 year plan, which is often cited as a benchmark for progress.
A lot can happen in a year, so imagine what happens if you continually work towards your ambition year-on-year, compounding your efforts.
The idea of compounding I think is key as it is easy to exhaust our initial drive to achieve something but more difficult to maintain the drive in order to have a meaningful impact.
Through my experience, I noted that:
A strong willingness for intensity at the start is nurtured by systems to become consistency.
Making the best of what you have: your skills, qualities, interests, network, etc., will plant the seeds to future growth.
It may not sound like a tough ask when the conditions are right, but our tendency to overcomplicate things steers us away from repetition and mastery.
Self-awareness is key.
Realising your passion isn’t possible without strategy.
Strategy is not just about business, how to scale and how to grow.
Strategy includes the systems you put in place so you can continue to enjoy your passion.
It contains the reason behind exercising your passion. The ‘Why’.
Hoffman highlighted that being passionate is a prerequisite to being world class, but especially in entrepreneurship, strategy comes first.
Irrational ambition and passion intertwine here as we explore our ability to sustain our belief despite facing self-doubt.
I watched a video by Andrew Paul, whose popularity exploded in 2024, starting from a couple thousand subscribers to amassing over 100k subscribers through his cinematic and brilliantly curated storytelling.
The topic of conversation was on being stuck in the middle.
He shared a very intimate reflection on his journey over the past year and his current position, where he describes having progressed to a point where the origins of ‘why’ he started seemed distant, but at the same time there is a feeling of being far away from having a foreseeable end goal.
This is where most people would quit.
A passion remains a passion until it becomes a burden.
When the novelty doesn’t hit the same, motivation dries up, and circumstances don’t cater the same way to the passion, why continue to follow it?
When nobody cheers you on, how do you maintain the drive to keep showing up?
My drive is sourced from purpose and gratitude - acknowledging the position I find myself in and making the best of it.
However, this drive can be overcast when the feedback loop isn’t as overt and efforts seemingly lead to more efforts.
Especially for creatives, where the metric for success is abstract and subjective, I think instilling that sense of purpose is a necessary constant to keep challenging ourselves and challenging our limits.
The same applies to you.
Our biggest challenge may be resisting the pull to try something new when in the chasm of progress; our efforts seem to plateau and outcomes feel invisible.
A change in focus could be the difference between achieving meaningful results and being stuck in multiple learning curves where we expected the results to arrive.
A strategy is what keeps us in the game.
Infinite Learner
Be open-minded, curious, and tenacious - learning is a lifelong journey.
Each lesson learnt is a step towards actualising your ambitions and being irrationally ambitious doesn’t allow you to fall into complacency or a fixed mindset on the knowledge you have acquired.
It may seem obvious, but entrepreneurs are constantly learning - they are infinite learners.
But I feel as if, whether you are a student, an employee, or an entrepreneur, as soon as you become reluctant to challenge your beliefs you close your mind off to learning.
Knowledge is not a one-and-done game.
Knowledge is something that has to be reiterated, tested, and applied in various contexts to be understood and retained.
Being irrationally ambitious urges you to adapt quickly, seek solutions, and reflect, in order to make things work, all of which are a part of developing knowledge.
A key takeaway I learnt from the podcast was Hoffman’s approach to iterating plans.
Start with Plan A. If it fails do not immediately fall to Plan B.
Only go to Plan B when after many iterations of Plan A the plan becomes worse than the original.
Whether it be personal projects or study techniques, I realised my approach was uncannily similar.
The lesson I’ve learnt is to use everything in your power to make Plan A actualised.
After all, that is the plan you desire.
If the plan is well thought out, the rate of growth will be exponential.
The person who is more self-aware is more likely to find opportunities that cater to them specifically.
In my experience, challenging what I know allows me to achieve new feats.
I recognised that fear of being challenged is an indicator of being comfortable in what I know, likely signalling to an underlying need for change.
Conclusion
I noticed a common theme amongst the 3 points I picked out:
They all start with ourselves.
Whether it is mindset, planning, or strategy, taking ownness of our actions positions us to succeed.
Irrational ambition combats helplessness and holds you accountable for your progress.
There’s:
Ambition;
Irrational Ambition; then
Delusion
In my opinion, the difference between ambition and delusion is self-awareness, i.e. you set out to achieve something because you are aware that it is possible.
There’s an agency that comes with thinking that the highly unlikely is possible. It’s liberating, and that is where irrational ambition plays on the cusp of delusion.
Hence it combats helplessness - it makes you believe and believe that you are the right person to interweave these possibilities.
However, on that journey of ambition the 3 points are reminders of what it takes to be persistent in achieving extraordinary things.
In the case of LinkedIn, without those frameworks, such innovation would not have been possible.
P.S.
How much do these points resonate with you and are there similarities in your approach?