Updated: Feb 27
Why overly experienced hires are bad for startups
I write a lot about what startups should not do, and it's true. But while my articles have an appearance of negativity toward startup life and culture, in reality, I love startups!
They are full of excitement, hope, and endless opportunities (if you are willing to break a sweat.) I have worked for startups in the past and currently work with several startups as part of my business, so I see the good, the bad, and the ugly from the Idea Phase all the way up to Series A and beyond.
It is my hope that by sharing all of the spooky scaries of Startup life I can help another Founder navigate the trickier patches that come with such a great responsibility.
Now on to an issue I see pop up with younger Founders: hiring the "Father Figure."
A "Father Figure" in the startup world is a term used for much older, more experienced industry veterans. These people have been the movers and shakers in their respective fields working their way through the trenches to be experts in their industries.
These professionals are the ones you worshipped through college and post-graduate studies, some of them probably even wrote your textbooks. Who wouldn't want to hire these people? They are the elite, the best of the best, they have built their careers from the ground up and they are giving your startup a passing glance!
It seems too good to be true but I promise you it is not. These professional juggernauts are the epitome of success in a sense; for an industry professional making over $500,000 a year minimum, at a global company, to notice and want to even be part of a three-man minimally funded team based on an idea, is monumental and gives merit to a Founding team's dream.
So why am I so vehemently opposed to hiring these industry elites for a new startup with young blood? Because they are completely out of touch.
Startups are a place of trial and error, starting fresh, and bringing new eyes and new talent to the forefront. It is a place where ideas and progress can flourish untethered into undiscovered territory. There is young, vibrant, and hopeful energy in the air, not yet jaded by the cruel corporate world.
These industry elites have been removed from environments functioning like this for years if not decades. The processes and systems are already established for them, they know nothing different other than established efficiency.
Some may argue that these veterans have done this before so they have the best knowledge, but unfortunately, this is not accurate in the slightest. Starting a business 20 years ago, 10 years ago, or even 5 years ago cannot be compared to the technology, advancements, and current climate of startups in 2023. They are just too far out of touch.
And, if we are being completely honest, they haven't had to do actual grunt work during the last 10+ years. At these major corporations they work at, they have pyramids of teams working below them doing the heavy lifting.
This is not me bashing these professionals, they have earned the right to not do the grunt work anymore. At this point in their career, they are here to supervise/advise, lead, and step in to do top-tier work like business relations and forecasting. It is not their job to coordinate meetings, update new software, create pitch decks, try to learn new systems, or be smiley and friendly with their co-workers.
However, in a startup, it is nothing but grunt work and everything I listed above. You have to play nice because the receptionist is also the HR Manager and Payroll Specialist, the Executive Assistant is also the COO/Facilities Manager, and the VP of Hardware is also your company IT/Security guy. It is a group effort where people are expected to jump in wherever necessary to get the job done, not sit in an office closed off from the world, and expect the small details to be handled for them.
Young Founders need to realize that while it is flattering for these industry veterans to want to be a part of something so new and so unstable compared to their 9-5 salaried corporate job, it will never end well.
They will be excited and say all of the right things to convince you that they "totally understand and really are fine with starting over at such an innovative company" which I believe is genuinely true. The problem lies not in their words but in their actions.
While they truly do mean to come in and get their hands dirty, they are not at all properly equipped with the skills necessary to execute at ground level anymore.
This is where a new startup will be eaten alive by the chaos this hire could create.
They struggle to execute basic company functions which causes friction with everyone else trying to pull their weight
They struggle to connect with their teams because they have never had to give the same respect to the receptionist as they do the CEO
They struggle to get into their groove because they are having to juggle 20 different tasks, some not even related to their expertise or title, wherein their last company each task had a person who specializes in that particular task assigned to it
They overcompensate for all of the above, desperate to regain a little confidence and control (and save face) by trying to implement clunky dated systems from their past conglomerates into a new efficient company
They sell the clunky dated programs to the Founders who bite hook, line, and sinker only for it to blow up in their face later and have to scramble to undo the damage
Frustration runs rampant among other employees who have put in ten times the amount of work only to get 1/4 of the pay, equity, and respect that this industry veteran receives.
From here it just spirals further and further until employees start becoming resentful, Founders scramble to rally the troops, and it eventually leads to full-blown anarchy. Everyone is doing their own thing, no one communicates, hatred for certain employees spirals to downright mutiny and soon the best talent quit because of how toxic the environment became.
I wish I was being dramatic but I have lived this exact scenario and now as an advisor/operational support specialist to Silicon Valley startups I have made it my mission to prevent this from happening again.
To all my young Founders or soon-to-be Founders, be confident in your choices. You don't need someone else to tell you how to make your dreams come true. By all means, hire them in an advisory capacity but never hire them to be an employee.
Armani suits and Gucci loafers don't fare well at all against jeans and trainers when digging in the trenches of startup life.