With some people… if I had a shot every time they said they “had” integrity, I’d be drunk as a sailor… but if I had to down a shot every time I actually “saw” such examples, I’d be sober as a kite.

“When someone shows you who they are, believe them; the first time. —Maya Angelou”

New York Governor Andrew Cuomo resigned. Political allegiances aside, there were moments where you couldn’t help but think he was a man of great integrity and character. Today it’s Andrew Cuomo, tomorrow it will be someone else. Without a doubt, we’ve all had wonderful mentors, people we have looked up to, who have helped us, and whom we hold in high regard. Not everyone is bad, not everyone will let you down. And when it comes to people we look up to, we’ve all had our Andrew Cuomos in our life (this isn’t merely about sexual harassment, but more about how we look up to icons and set ourselves up for disappointment and heartbreak).

But, if the allegations against Mr. Cuomo are true, then it’s another reminder that, more often than not, in the end, people will let you down.

Over the past 15 years, you can imagine I’ve held strategic conversations with hundreds of investors and media companies. Usually, I’m drawn to the company, sometimes the people. One time, ages ago, we held early-stage conversations with a media company that wanted to buy WatchMojo. I respected the company, but I admired the champion of the deal. We’ll call him Jack. As there are many stages of mergers and acquisitions, this was early in the process and the conversation never went far. 

Free Finance Advice

Initially, the interested party wanted to acquire a significant majority in a straightforward control deal. Before long, due to board approval requirements (I was told), the structure evolved to a more convoluted slight majority whereby they would have a call option (aka a right to buy) the remaining portion but they refused to give me a put option (the right to sell) the unsold part of the business. 

Some Life Lessons

As I contemplated the opportunity, in essence, I was being asked to take on uncertainty whereas they wanted as much clarity around their interests. It boiled down to trust, character, and integrity. Striving to be a reasonable and trustworthy person, I was open to it… but eventually, my advisors discouraged me and my instincts told me I would be disappointed over time, especially if they refused to buy the balance while shifting their money-losing units underneath us, which would reduce our value. Say we earned $1M in profits before the deal, but they then merged their money-losing units with us. If we broke even, they could have bought the balance for nothing. As a finance-trained person, that’s what I am trained to spot. As an entrepreneur, paranoia is the baseline for your thinking. 

Thanks, But No Thanks (we’re cool, though, right?)

Instead of dragging them on, at the earliest crossroads, I politely declined. Amicably, I thought, we parted ways. There’s a reality that when someone wants to buy you. If you turn them down, they will try to kill you (see: Facebook vs Snap, the early years). Other times, the party that was turned down just moves on, almost offended and hurt. People say “It’s business, we don’t take it personally.” but those are just some of the lies people tell themselves.

FOMO vs ROMO (Regret of Missing Out)

Now, from a strictly financial sense, passing on the deal was the right call. But, I’m human. We walk the line between fear and greed. For years, I wondered if I’ve done the right thing for the company, its stakeholders (leading with employees), myself. For years, I would question myself, realizing it was futile but unable to simply get it out of my mind.


Fast forward to today, the main champion of that deal – Jack – emerged elsewhere, and we reconnected to see if we could pursue a commercial partnership on another matter where we introduced two parties to collaborate on a project. Hey, if we could execute on one project, perhaps we could do more things.

For the past few months, we had more or less finalized the salient terms and slowly but surely ironing out the outstanding terms and conditions, getting ready to sign the final agreement. Then, I received a text asking:

“Hey Ash, Wondering if you have five minutes tomorrow just the two of us, at your convenience? no rush and all good.”

I knew something was up, and due to new developments, they wanted to revisit the terms. That’s fine, but given that I introduced the two groups, I felt a need to ensure fairness.

How you go about things is more important than what you are trying to achieve. I’ll spare some of the details which would further explain my disappointment, but I’ll simply state that while trying to ensure neither party took advantage of the other, I was lied to, thrown under the bus, and when I had the audacity to say this doesn’t seem fair or right, Jack reminded me that he “had integrity.” Sure. The straw that broke the camel’s back was his subsequent sense of indignation which seemed a tad too much. I’m sure corporate chiefs are used to bulldozing their way around, intimidating subordinates and gaslighting those who push back. Newsflash: I don’t care.

All Bets Are Off

Adding further insult to injury, he said “this is why we didn’t reach a deal then.” I wish I could be more stoic sometimes, but at that moment, my Masters in Not Taking Shit From Anyone kicked in.

“No, Jack, we didn’t reach a deal because you changed the terms (and pointed to your board, and I gave you the benefit of the doubt). But this time, there is no board to pin the blame on.”

Twenty years into my career, the pattern is clear: most of the people who rise to the top in corporations do so because they are willing to compromise their principles and integrity to do their board’s bidding, to walk away with the spoils. But, by the same token, I don’t lose sight of my privilege as an entrepreneur, founder and owner. Entrepreneurs tend to be long-term greedy (we are after all masochists), whereas executives have to be more near-sighted – for themselves and their companies – it helps that they are more sadistic in nature.

A mixed blessing of never have had outside investors is I could never take the easy way out and blame my words, actions, and deeds on others. As a result, I went out of my way to display as much character and integrity as possible… which makes the lack of reciprocity unfortunate and disheartening, but such is life. You can’t control how others play the game, as in sports, some will be more aggressive, others more sportsmanlike. To each their own, but every time you step on the field, remember that there is a course to success through fair play.

YOU Don’t Get to Decide If YOU are Honest

I sometimes say “I’m very transparent” but because I then proceed to say something so honest and candid that people literally tell me “thank you for such transparency.” But I have made an effort to stop saying it, because integrity, truthfulness, candor, transparency, etc. is not you yourself thinking you have it, but others knowing you have it, based on your words, actions, deeds. This, in bold from one of my advisors, is really what drives me more than any other measure of success.

"Great news on the year's results. A lot of hard work and smart decisions to get to this point to let WatchMojo grow into its next phase. On a personal note, you have been great to work with, an inspirational leader, true to your word every step of the way and built a impressive business and culture.  Not many people can check all those boxes.  For me it has been a great privilege to get to know and work with you!  Look forward to watching WatchMojo grow and prosper and let me know if I can help in any way whether formal advisor or informal advisor - I am here to support you and WatchMojo.

Human beings are on a journey balancing Good v Evil, managing sins and virtues they face. You could spend decades building your reputation, and one moment to lose it. For me, any lingering doubt about whether I made the right call to turn down Jack’s offer years ago washed away. We will never know for sure, but it was now clear that despite all of his verbal assurances, he would have moved the goalposts and likely not kept his word.

It’s normal for you to second guess yourself and wonder if you made the right call. More likely than not, if you trust your instincts and stand by your principles, it’s more than likely you did. When I think that this was someone I was considering appointing to the WatchMojo Board, I am once again reminded that everything happens for a reason. You just need patience and perspective to come to that conclusion.