Over the holidays, I broke down how people, products and companies avoid Death, by looking at things through the Sins and Virtues.

Success boils down to people – how we react to events, how we balance forces of Good vs Evil. Now I am not religious, but I am spiritual. But since religion was just a framework to tell history and explain mankind’s actions before Science came along, then I sometimes turn to it to explain matters of life. The seven deadly sins, also known as the capital vices, or cardinal sins, “is a grouping and classification of vices within Christian teachings, although they are not mentioned in the Bible.” Conversely, the seven heavenly virtues are, according to “Catechism of the Catholic Church ‘habitual and firm dispositions to do the good.’ Traditionally, the seven Christian virtues or heavenly virtues combine the four classical cardinal virtues of prudence, justice, temperance, and courage (or fortitude) with the three theological virtues of faith, hope, and charity. These were adopted by the Church Fathers as the seven virtues.”

Companies fail either because they picked the wrong strategies, initiatives or simply could not execute. But since the mission of Context is King is to bring together the psychological aspects of business & touch on entrepreneurs’ struggle with balance, I will break success down by framing it in the context of sins and virtues. Companies and people fail because of:

  1. LUST: Driven by sex, money or power? When it involves the latter, scandals will invariably bring down projects when the people steering them are taken down. If it’s money or power, all I will say is that money and power need to be a by-product of your journey. I’ve studied a lot of successful people and none of them are singularly focused on money or power.
  2. GLUTTONY: Spent too much money, too fast… once they wanted to scale back, morale is hurt.
  3. GREED: Acted selfishly in partnerships with the vendors, suppliers & distributor AND people one needs to excel in business, in win-win frameworks. Nothing is ever 50-50, but it has to make sense.
  4. SLOTH: Waited too long or was slow in acting.
  5. WRATH: It’s a matter of when, not if, you have a disagreement or impasse… how you resolve that determines your ability to succeed.
  6. ENVY: Fuelled by envy chasing fads instead of focusing on their comparative advantage and in areas where they could achieve a positive outcome.
  7. PRIDE: Suffered from hubris, which manifests in many ways, including the belief you are better than others and have a sense of entitlement. No one owes you anything in life and you should never take anything for granted.

To then explain your success through the Virtues:

  1. CHASTITY: In 2006, investors weren’t merely balking at funding content companies, they also didn’t love husband and wife founder duos. But one benefit of having a couple nurture the environment early on is the office doesn’t turn into a locker room.

    Thus for many reasons, we were blessed to avoid experiencing MeToo episodes. I’ve always fought for the underdog, so if I even sensed any possibility of impropriety amongst the troops, I would have addressed it swiftly. Too many executives and entrepreneurs don’t. How you handle these situations are key tenets of success. But this also explains why the company remained small. Maintaining such an environment becomes more challenging as you grow. But if you can accomplish it, it is much easier it is to recruit talent and retain them.
  2. TEMPERANCE: Our success boils to wanting to serve others. Practically in business this means asking yourself how the counter-party or other person would feel or react when you present them your perspective. I’m always focused on how the staff would receive news and changes. Empathy and humanity are not liabilities, they can be turned into assets (loyalty & reputation).
  3. CHARITY: in addition to the obvious iterations of charity, entrepreneurs at their core lead by example and would not ask their team to do something they wouldn’t do themselves, sacrificing as they need be (I am not complaining, I had savings from “previous glory” in the words of fellow investor John Stokes, but the fact remains, I didn’t really collect a salary from 2006 to 2011 while mortgaging our place to avoid layoffs). But more critically, the instant we turned a profit, we implemented a profit-sharing plan with all employees. Given our Field of Dreams editorial approach and platform-centric revenue model (i.e. YouTube’s AdSense), it was anchored around the editorial team. Even in our intense investment years when revenue growth stalled while costs soared and profits tumbled, we kept bumping salaries up aggressively as we were profitable after all and could see which initiatives would be sustainable and which ones wouldn’t. Naturally, as some projects didn’t take off, people left. I hated losing people, but I’d be lying if I said I wasn’t also relieved. My “people before profit” mindset prevented me from mimicking our larger peers and doing layoffs – I was perfectly happy with a bit less profitability, hoping the initiative would find platform/format fit. That said, not buying into “hire slow, fire fast” was a mistake. Montreal’s job market and affordable cost was in our favor from a demand / supply dynamic but we never exploited it:
    – early on offering full-time salaries with health benefits and paid vacation even though the industry trend was toward freelance model;
    – offering paid internships to students, many of whom went on to grow into manager roles over the years (before society and industry woke up to realize that the unpaid internships were not exactly fair or ethical);
    – hiring aggressively through a paid apprenticeship program for young graduates with little experience, whom we could invest and train in before determining culture fit and whether they wanted to pursue an office job. Instead of hiring 1-2 people, we hired 20+ in 2017-18! We didn’t hire youth to have them get us lunch, we hired people and gave them a platform; but as Jack Welch would say, not everyone has the runway or drive. After all, we were largely recruiting aspiring creatives and/or fans of pop culture, and not engineers or accountants.

    The fact of the matter is we probably hired more English communications, media, journalism students than The Montreal Gazette, CBC, etc. combined. But because of our deficit-financed, we were hiring & incurring costs with no real revenue behind those initiatives. This meant losses on those unit’s P&Ls with no guarantee of any path to revenues, let alone profitability. I acknowledged that we could wait six years to break-even on WatchMojo, but didn’t have the same luxury now because our opportunity cost was higher. As I wasn’t comfortable spending other people’s money, we were effectively drawing from the core product’s profits and thus had to be conservative, especially given how unproven many of the recruits were. I do acknowledge, however, that to a 21-year old I’d hired in 2017, the financial sacrifices I made from 2006-11 and legal spectre thereafter were unrelated to them because I’d largely sheltered anyone from the struggles on the field and in my mind. We also hired at the high end of the experience spectrum, but that’s for a #FutureArticle.

    The system worked and all came together in 2020, but admittedly, I could have communicated my method to the madness better and been less “Taarof-ey.”

    This year we issued record compensation to the team, who earned it and then some.
  4. DILIGENCE: Persistence and Effort. Playing soccer taught me so much about management and leadership: i) working with characters, ii) team work vs selfish players, ii) finishing your play, iv) being accountable, v) ethical fair play. I also realized how one player could be the difference between wins and losses, but one bad apple could make it impossible to win.
  5. PATIENCE: I am fiery, passionate and competitive. But I’ll never get mad at people, I get upset at outcomes and yes, occasionally someone “has to do the yelling” and firing up the troops. You also do that to then create a ripple effect where other leaders – some silent, others more vocal – emerge. Sounds crazy but I like it when people interrupt me (sometimes), and I only interrupt people on two occasions (which ones? another article). That said, it doesn’t mean you love losing your temper. No one does. Yelling is the management version of Michael Jordan’s “I succeed every day because I fail every day.” However, over time, people definitely nuance that it’s not the “player” that’s being yelled at personally and instead the focus having been on the “play” or “outcome.” Being based in Montreal, I always cited the fact that I had a team of nice Canadians as a double-edged sword. I wouldn’t trade them for anything, though. The people you can build championship teams with know and understand the difference. Trust me, it’s not like my best team mates have never yelled at me. It’s part of this racket, but if it’s too frequent, it not only gets stale, but also loses effect. Balance!
  6. KINDNESS: Taarof is both the best and worst behavior from my roots. The only thing that ever truly disappoint and thus angered me were instances of wasted i) opportunity and ii) resources. Why? Having been given so few opportunities as a young professional and then subsequently been so strapped for money, I felt it an obligation to create as many opportunities for others as quickly as possible. I may have overdone this by hiring way too many people, too quickly. I learned some painful and heartbreaking lessons, where now I understand that I, too, need to sometimes pause. Going forward, seeing some of the efforts by Mr Beast or Dave Portnoy makes you wonder about how you can manage your time and energy and focus on impact, than just sheer volume of hires and so on. I don’t need the biggest army, I need the right one. You don’t need to penetrate through all fronts, you need to move into the right direction.
  7. HUMILITY: You must possess and display bravery and reverence to win. Granted, I acknowledge that dedicating a whole article let alone website to my experiences in life will not come across as very humble or modest. Two counter-points:
    • I’m an eternal student who’s always learning. Researching and writing are foundations of learning and education, which is our mission in life.
    • I’ve made many mistakes, but by understanding that facts and figures are part of the equation and people’s emotions and feelings come into play, we were able to steer through and persevere.

The truth of the matter is, our success is the result of a collective, naturally that meant some conflict. But thanks to our communications and culture, we contained the sins and were guided by a more virtuous path to a better outcome.

This was an “excerpt” in a longer article on Company Lifecycles.