Behind every glorious exit and fanfare of a new startup founder being the next Big Thing, there are stories you haven’t heard about founder f**k ups. Scratch the surface and you’ll reveal the crash and burn of failure that ultimately was down to the founder themselves. This may sound harsh, but the reality is many founders have an ego and believe their own judgement, have blinkers on blinded to their offering, or simply drop the ball to flawed errors of judgement.
The startup journey is a rollercoaster that requires resilience and reflection to get through the many twists and turns. Whilst many do reflect on personal struggles that can help lift the load before hitting the buffers, there’s considerable baggage and hesitation towards stepping into this transparency.
Failure. We’re hypocrites about it. You find scores of pleasant aphorisms celebrating the inevitability of failure of underdogs and entrepreneurs, their determination to come fighting back and the importance of learning from it, but in real life failure is painful. But I’ve had enough of the F-word as some cathartic zen practice and taboo, so it’s time to call founder f**k ups out to help others repeating the same bad practice.
If you’re reading this and just starting out, don’t get discouraged by exaggerated narratives around success and loss. Instead, connect and build a team, bake trust with them, listen to their experience, expertise and points of view, and develop a willingness to get vulnerable from the outset. Remember that failure isn’t an indictment, and above all, try to deal with failure while it’s happening – the mark of true personal vulnerability.
Many founders face defeats, setbacks and feelings of inadequacy, a tower of self-doubt that looms large, despite valiant attempts to shore up their venture, but in my view, too few have self-awareness of the self-inflected damage they are doing to their enterprise and simply believe their own mantra and rhetoric, rather than seeking the advice and support of others. That omission sacrifices much needed depth and dimension in the broader conversation about startup failure.
After all, phrases such as fail fast and celebrate failure as learning are frequently thrown around. We’ve seen many founders up on stage talking about their biggest mistakes as celebrities, but all too often, the conversation stops there – few keep digging to uncover stories not wrapped in platitudes. True vulnerability about how those personal struggles rearing their heads in the here and now is a rare sighting. I’ve also seen founders on the conference and fire side chat circuit offering insight and wisdom to their journey when truth is they’ve not developed a repeatable, scalable sales model.
Let’s walk through the specific challenges founders face. Yes, it’s admirable that most founders learn and pick stuff up as they go along, but let’s also share effective tactics for reversing the sheer ego mania of blinkered decision making. Optimism is key, as Friedrich Nietzsche said, That which does not kill us makes us stronger, after all, isn’t it the lack of fear of failure, a willingness to stumble during a quest, that gives the motivation to spur us onto success against all odds in the first place?
Don’t let failure remove your spark, but having said that, embracing failure to encourage entrepreneurship is misguided. Founder f**k ups should not be celebrated, yet there is a cult of failure surrounding entrepreneurship. Failure’s become trendy. Everyone automatically views failure as a stepping-stone to future success. But it’s an abstract layer. Talk about the potholes you fell into, the errors of judgement down to ego or arrogance, not just the ones in the rear-view mirror.
We need to take the conversation to the next level, so here are ten common Founder f**k ups I’ve seen several times, and a remedy to avoid them.
1. Misplaced self-belief The broader narrative around success and failure creates an innate hesitation to open up and leave the founder exposed. Showing vulnerability and asking for help doesn’t stop that line of questioning, and checking in on the internal monologue, but blinkered self-belief is unforgivable.
Remedy: Prop open your door and mind. Create the space to meet and talk with other founders. Don’t base your understanding of what it means to succeed or fail on what you read about industry deities, take inspiration from the founders that surround you locally at the coalface. You need to hear the stories from the trenches that will help keep you going.
2. Falling into the hyped circus of startup founders I’m the next unicorn. There’s this notion that the only companies that are really successful are the ones that are growing with triple digits. We don’t really celebrate success, we celebrate ultra-success. Actually, It’s not enough to be a unicorn anymore, you need to be a decacorn.
Remedy: Drop the façade. Be the person your dog wants you to be when you get home. Lean on your network and cut through the small talk. Don’t kid yourself.
3. Focus on fund raising and not customers It’s one of the easiest fiascos to spot. We’re heading towards a Series A. I always choke on my brew when I hear this. There’s a culture of celebrating monetary outcomes to such an extreme degree and deifying the people who get to that point. When you’re not there, you’re not making it, apparently.
Remedy: Walk on the other side of the road, spend your time talking to prospects, generating leads, and nailing those invoices. You can only build a sustainable business on cash generated from customers.
4. Taking too much investors’ money too early Other peoples’ money changes everything, but the only thing you owe your investors is your best effort. If your startup fails, you don’t have to make it up to your investors. You don’t owe them a thing – unless you really didn’t try. Bootstrap for as long as you can.
Remedy: Chose your investors like you chose your spouse, align on values and intrinsically understand they have a different agenda to you. Equally, find an investor that has built and exited their own venture, they’ll have some valuable insight to share.
5. Not hiring the right team or not trusting your team Plenty to go at here. It was everyone else who screwed up. I did everything right. I’ve heard that several times. It’s vital not to hire the wrong senior people too early, they’re not only pricey, but when they’re a mistake, they’re a big mistake. ‘Really smart’ doesn’t always translate into being able to execute quickly and iteratively.
Next is hiring great people and then not trusting them to get on with it. Micromanaging isn’t a healthy approach, switching your teams priorities on your choice only fosters an unhealthy culture. In a tech startup, your CTO needs to feel comfortable pushing back, especially if you’re a non-technical founder.
Remedy: There is no such thing as a solo-founder, rather a founding team, so spend time crafting your team strategy and culture – as much as you do on product.
6. Thinking the hustle will someday end Many founders dream of hitting milestones and think things will get easier. But every smart experienced entrepreneur will tell you, some things get easier, but then you find new, harder problems to solve. Entrepreneurship is a path to endless hustle. It’s like a rollercoaster; there are always ups and downs.
The appeal of breaking out of the traditional job is tangible, but the reality is that while you leave behind the old schedule you exchange it for new demands. There will be more freedom in some respects, but a startup can consume every part of your waking life.
Remedy: Do the work, and if it’s not for you, get off the bus. Make sure you enjoy the journey on the way, instead of only obsessing with hitting the next milestone. If you can’t do that, the process will exhaust you.
7. Flying solo I had this great concept, and I just couldn’t handle the idea of letting others get involved. Founders miss crucial relative context around their work. Many are focused on proving that they were right as opposed to being effective, and this ends up with emotional and volatile situations where discussions and decisions are unproductive. This doesn’t give founders the opportunity to provide the leadership that a growing and transforming venture needs.
Remedy: Get a mentor early on. The reality is that a single key to success does not exist. If anything, entrepreneurial success requires a keychain of different ideas, people, and resources that come together at the right time and place. A mentor gives balance, perspective and focus – the distance between dreams and reality is ultimately discipline.
8. Focus on your product, not customer problems In a first session with a founder, I asked a simple question, but the answer was complex around the product. I packed up my stuff and said, I’ll be back next week. You have homework. What is the problem you’re solving?Spending tons of time thinking through product bells and whistles and not validating your riskiest assumption and not making fact based decisions based on your target market is a clear recipe for a f**kup.
Remedy: Catch yourself before spending a lot of time thinking about long-term functionality. Validation is always on. Your startup is constantly a temporary hypothesis around value and traction. You need to change your approach from a delivery-focused perspective to a testing perspective.
9. Not being realistic about cashflow These endpoints of failure colour our perceptions of what it really means to succeed and fail: we slowly lose our grip on reality. Some founders mistakenly believe that starting a business will put them on the fast track to earning substantial amounts of money, but properly timing cash breakeven is one of the biggest tasks.
Remedy: Just like fish pairs well with chips, so does instinct and data. Get handholding on financials if they’re not your strength.
10. Not getting stuck into sales & marketing early enough Dial back the hubris and get out of the building, listen to prospective users, and act and do what is right regardless of what you think you should do. Sales and Marketing are vital activities in terms of reaching and connecting to prospective customers, but they’re also great tests of your hunches – not validating your assumptions will be costly. Get customer insight so you can change your behaviour.
Remedy: Wanting too much too soon, fight your blind spots with real conversations with people. Have clarity in positioning the promised value. Customers need to understand precisely what you are a solution for. Your messaging and branding should run alongside your MVP in the early stages to generate early adopters.
A pitch goes badly. A key team member exits unexpectedly. An investor fails to commit. The product launch is taking too long. Marketing isn’t paying off as anticipated. A key customer drops out. Failure happens to anyone. Sometimes you win and sometimes you learn.
Not everything that goes wrong is a founder f**kup, but we are biased, sometimes things only happen in our head where we have spectacular blind spots and bias. Maybe the most important takeaway, is that in any crisis or failure there is this collateral beauty, an opportunity for reflection that is often the source of progress. As William Shakespeare wrote in Julius Caesar: the fault, dear Brutus, is not in our stars, but in ourselves.
The purpose of life is to pursue happiness. Our philosophy is not best expressed in words, it is expressed in the choices we make. In the long run, we shape our own lives, and we shape ourselves. The process never ends until we die. And the choices we make are ultimately our own responsibility.
