Avoiding the Cofounder Crypt

Avoiding the Cofounder Crypt

Here’s a fact.

Finding a smart operator to work alongside is one of the most difficult challenges an entrepreneur faces.

Your choice of a cofounder or partner not only determines the future of your company, but also yourself.  

In fact, Icehouse Ventures reported that out of 100 businesses they funded, 35% of these had a founder leave the company, costing the startup time and money.

Below, I examine several co-founder traits and red flags you should watch out for. 

This will help you avoid falling into the ‘cofounder crypt.’ 

Keep in mind that most of my examples are drawn from personal experience. 

And you can take solace in the fact that, if you experience awkward situations and odd behavior from your cofounder, it (usually) isn’t you that’s the problem.

It is them!

Normalcy is a myth

Prepare to work with oddballs.

The only normal people are the ones you don’t know very well.

Alfred Adler

In his book, Lucky Or Smart, entrepreneur Bo Peabody wrote what is, in my opinion, the greatest chapter in any book on start-ups. 

The title? “Startups Attract Sociopaths.”

Not the best and brightest.

Not the top of the class.

Not the award winners.

But, sociopaths. 

Ordinary people don’t agree to work for start-ups. They go get ordinary jobs. So, as an entrepreneur, you’d better like odd people, because that’s who is going to agree to work with you.

Bo Peabody

This is one-hundred percent accurate. 

Start-ups are filled with misfits, oddballs, and outcasts (and are often led by them).

Even the most widely respected and successful founders are not immune to this phenomenon. 

Before Steve Jobs became the ubiquitous figure that every founder wants to emulate (which in itself is a major red flag), he exhibited a few odd quirks that were anything but normal.

  • Steve believed his vegan diet meant that he didn’t need to shower more than once a week. He also didn’t believe he needed deodorant.
  • He would often walk around barefoot.
  • Walking around barefoot isn’t that odd until you find out that he frequently inserted his feet into public toilets to de-stress. 

In your search for a smart operator, cofounder, partner, or even leader, prepare for the antithesis of normal behavior.

You have been warned.

Expect to meet unreliable people (who will haunt you)

Reliability sounds simple. Answering an email in a timely manner, showing up on time, and delivering on your responsibilities should be basic requirements that everyone can fulfill.



In this age of mass communication and mass distraction, the trait of reliability has become antiquated. 

In relationships, people tend to ghost or are left unread. 

In the world of business, it is worse.

You are haunted.

Here’s what I mean…

You exchange communication and move forward. Then, when it’s time to act (signing a contract, attending an important meeting, making a strategic move), the other person doesn’t show.

Sure, they will remain in communication but things get postponed or rescheduled. No action is taken. Nothing is accomplished.

Like a poltergeist, their ethereal presence is there within your company, but you receive no benefit from it.

And because you can’t move ahead, all of your hard work and plans begin to fall apart. 

Strategic partners begin to doubt your judgment. Investors lose interest. Supporters start to flee.

Your promising start-up rots away because the partner you thought was the correct choice has left you in the lurch.

Coming from the world of nightlife marketing and promotions, I once had a great partner. He was intelligent, professional, reliable, and quick.

We planned big, dreamed bigger, and took massive risks (some of which almost resulted in academic expulsion).

There was only one problem.

On the nights of our major events, he often showed up hours late (if he showed up at all) and was already inebriated. 

This wouldn’t have been an issue if he was a paying customer, but as a partner who had certain responsibilities (the most important of which was to be sober!), it was an enormous red flag.

And it’s the major reason I preferred to be a solopreneur for most of my nightlife endeavors. 

Honesty is rare

We are all taught that honesty is the best policy. However, when it comes to our professional careers, it is a rarity. 

Why is this the case?

Because years of social media consumption has conditioned us to parade our successes and conceal our failures.

People don’t want to read about your failures and what you learned. They don’t want life lessons. 

They want to hear about your successes, your exciting life, your major milestones. 

The algorithm supports this by driving traffic and promoting what is popular, whether it be misinformation or sensationalism.

Obey the algorithm.

Follow what is fun.

Bury what isn’t.

Paradoxically, this has led to a culture of braggadocious behavior which makes it difficult to find a truly authentic operator. 

For example, you may come across someone who claims to have had a successful business exit. Yet the exit had nothing to do with them because they were an employee — not a founder or executive who was responsible for the liquidity event. 

These assertions are more common than you think:

  • The serial entrepreneur who (conveniently) has no record of his previous work
  • The self-made success story that doesn’t hold up to scrutiny
  • The expert who attended an Ivy League school but, in reality, only holds a certificate from a course, not a degree.

I remember when one of my clients wanted to introduce me to Alberto Chang Rajii in Miami. 

Alberto was a self-made billionaire. He had gone to Stanford, was one of the first investors in Google (he was given 1% equity in exchange for $10,000), and used the cash he made to launch a global VC fund.

There was only one tiny problem.

Stanford had no record of him.

No one at Google had heard of him.

In the end, it was all exposed as one big lie. Smoke and mirrors. A Ponzi scheme.

The truth eventually comes out. Make sure you complete due diligence to avoid ending up in the crypt (or in this case, a cell).

Shared experience is beneficial

Having shared experiences — your background, industry vertical, or mutual interests — can prove beneficial. 

Strangers are the unknown. All you learn about them comes from their online bios and social media profiles. 

When two people meet, they don’t appreciate their respective strengths and weaknesses. They don’t know what one another can bring to the table. A resume and a LinkedIn profile only tell you so much (and is that even accurate?).

You need to establish a relationship with whoever you choose as a partner. 

You need to determine if your shared experiences will benefit what you build — and the decisions you make.

Paul Allen and Bill Gates had a mutual love for computers before they formed Microsoft. 

Larry Page and Sergey Brin met and started Google while at Stanford

Alexis Ohanian and Steve Huffman were college roommates before they created Reddit. The list goes on.

Understand that you won’t stumble upon the right cofounder if you have nothing in common. 

You will spend a great deal of time with this person. More often than not, you will spend more time with them than you do with your friends or family.

You need to have something that binds you together and also allows each of you to grow your enterprise and personal skill set. 

For some, their shared love for money is enough. Others rely on their mission and the problems they truly believe they can solve.

It is different for everyone.

At my first meeting with a general partner from Improve Ventures (where I am also a partner), the conversation wasn’t centered around investments or entrepreneurship. 

Instead, we discussed our mutual love for a South Beach nightclub. 

In the past, he was a customer at this nightclub and I was a promoter. Although they probably wouldn’t admit it, I suspect one of the reasons I was offered a GP role was due to that conversation. 

You will recognize the value of shared experience when you discover it. 

That brings me to my next point.

Navigation: the inner feeling

Fingerspitzengefühl is a German word translated as “fingertips feeling,” and means an intuitive flair or instinct. It is often used to refer to situational awareness and the ability to respond tactfully.

We need that talent, especially when we seek someone we can trust and work with over the long term.


Because navigation is the one skill that the majority of us were never taught.The ability to be a proper navigator of others and of life. 

Your navigation skills could make or break you or your business.

You must learn how to navigate people. 

Like hazards at sea, you need to know who to avoid and who to seek out. You need to flee from the toxic harbors and instead seek shelter where you can resupply and prepare for the oncoming storm.

You need to trust yourself and listen to your gut. People often promise you the world to be part of what you are building, only to utterly ruin it. 

Start-ups have a shelf life. The journey is often a one-way trip. And every adventure seems exciting until one is on it. 

You need to navigate the countless people you encounter until you find the right match. The one person who won’t haunt or cause you and your idea to decay. The one who can deliver.

I meet many founders who are keen to work with me in some capacity. It’s now easy for me to tell in a minute or so if they are serious.

I have a checklist:

  • Are they serious about what they are building?
  • Do they understand the value of time?
  • Are they based in reality?
  • Do they understand the game they are playing?
  • Are they educated about their vertical or do they just talk in buzzwords?

My inner compass has not always worked to my benefit, but with practice comes experience. And experience has led me to continue to dig deeper.

Follow my lead on this.

Because when you dig through the garbage and actually find the right partner, it is life changing. 

When you find this person, you may call it fate, good fortune, or destiny.

In reality, it is the result of your navigation skills. Your ability to cut through the nonsense and the bullshit. To see people for who they are, not for what they say.

Don’t rely on their social media profiles; these are often embellished.

Don’t look at their business history; you won’t find many faults.

Instead, look at them as a person. 

  • Do they take action? 
  • Are they reliable? 
  • Do they come through for you? 

Above all, do you see yourself working with them for many years to come? 

If so, this person may be worth their weight in gold (pun intended). 

Final thoughts

Finding the right business partner is no easy task.

You will face frustrations and setbacks. But that’s not a reason to stop. You need to be both patient and vigilant. 

The ideal person may not exist but the ideal business relationship does. 

Remember that the person you seek is probably out there (in anonymity) looking for you, so keep moving forward until you find one another. 

The alternative is that you make a poor choice and face a future in the cofounder crypt.

And that is a destination no one wants to travel to.

Happy hunting. 

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Shaun Gold

Shaun Gold is the true definition of a polymath. He is a lifelong entrepreneur, 2x best-selling author, international speaker, advisor and super connector to start-ups and standouts, Jeopardy contestant, and screenwriter. He not only writes YouTopian Journey, but also heads content creation for various startups and founders, including OpenVC.app.

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