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Today I want to talk about adversity. First, some context. Over the last 4 years, I’ve grown my bootstrapped business to $60M+ in revenue and exited to private equity. On the surface it sounds great, but that's only half the story. While the outcome was great in the end, the journey was not up and to the right. It was filled with misstep, elation, failure, enthusiasm, doubt, courage, hardship, conviction, hope and luck.

Wow that's a mouthful right? If I'm being honest, today it's the exact same minestrone soup of emotions - just at a different scale. As a business builder, you consistently face a spectrum of different emotions when going through the journey. Mega highs on some days and the lowest of lows on others; sometimes both in the same day.

One of the traits I most admire in people - regardless of if they're in business or not - is emotional steadiness. I'm a firm believer that you can get through anything with emotional steadiness. It's never quite as good as it seems; nor is it as bad. There is always a move to make and a hand to play. But if you're emotionally unsteady, this clarity of thought often eludes you.

To that end, I came up with 14 principles to help me whenever I'm facing a critical situation. Each principle takes inspiration from Greek philosophy:

• Logos - Have we found the ground truth?
• Ethos - Do we believe in the ground truth?
• Pathos - Are we inspired to act upon the ground truth?

Not every question applies to every circumstance. But many of these questions overlap more than you’d think. Whenever you’re facing a difficult situation, run through the most applicable question. With that said, let’s get into the list.

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Question 1: Am I being arrogant?

If you think you’re right and someone else is wrong, ask if it’s because you have better:

(A) Information (B) Judgement (C) Instinct

In my experience, if it’s not at least 2/3, you’re missing something that could lead to a better outcome.

Question 2: Am I judging the delivery or the substance?

You have to separate the message from the messenger.

If messenger > message, you create an environment that breeds “cliques” and “sides”

If message > messenger, you create an environment where meritocracy wins.

Question 3: Am I connected?

As your organization scales, it’s hard to be as plugged in as you once were. Your job as a leader is to maintain perspective. If you don’t have the ingredients to make a call, (a) dig in or (b) entrust the decision to somebody else.

Question 4: Am I being too pessimistic?

There’s a fine line between being realistic and being negative. To be realistic (and not negative):

• Maintain a vision of the opportunity
• Be disciplined in the pathway to achieve the opportunity

This approach builds credibility.

Question 5: Am I being too optimistic?

Being overly optimistic is dangerous. We romanticize this in company building, but in practice it creates less reliable, stable and enduring orgs. Ask yourself, if an unplanned risk were to come up tomorrow, how would your business fare?

Question 6: Am I being consistent?

Everyone on the team needs to know:

• Where the goal post is
• What the expectations are

As a leader, you need to make sure you are consistent in your commitment to these standards. The moment you let up is the moment you regress.

Question 7: Am I being passive?

Every issue starts as a snowball. Direct communication prevents snowballs from turning into boulders. I’ve learned (the hard way) that this approach is ultimately always better for the team. No matter how uncomfortable it is at the moment.

Question 8: Am I letting perfectionism get in the way?

Focus and attention to detail is important. But I’ve found through experience if you extend this to its logical extreme, it can be paralyzing. Optimal balance = getting the little things wrong and the big things right.

Question 9: Am I trying too hard to please?

In the short term, pleasing people is easy - it quells the momentary discomfort. In the long term, it’s cancerous and the fastest way to kill credibility. Promoting truth is the only way to build long term sustainability.

Question 10: Am I overthinking this?

Every substantive decision has pros and cons. Analysis is important, but overanalysis leads to paralysis. Bias towards action and moving in the right direction vs. endlessly analyzing. Especially because most decisions are reversible.

Question 11: Am I focusing on the input or the output?

Bad input, bad output = Incompetence

Bad input, good output = Luck

Good input, good output = Repeatable

Good input, bad output = Keep It Up

Good inputs lead to good outputs with enough attempts. Keep shooting.

Question 12: Am I afraid to decide?

It’s ok if you don’t have the answer, but it’s not ok if you don’t have a path forward. How do you define a path forward?

• Confer with others
• Collect more information
• Set a timeline for the decision

Whatever you do, don’t punt.

Question 13: Am I taking enough risk?

This can be overwhelming. As a leader, it pulls you from your comfort zone. But growing a company isn’t a straight line up and to the right - it takes big moves to cross the chasm. Too little risk = short term comfort, long term pain.

Question 14: Am I leading from the front?

If you want people to give their all, you have to set the tone. In my company I leave no doubt that I am the hardest worker. Nothing builds respect like showing vs. telling. This isn’t the sexy part of entrepreneurship, but it’s by far the most impactful.

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I look at these 14 questions whenever I’m facing a challenging situation. I hope these help you as you build your business and inevitably deal with adversity. Let me know if you have any other questions I should add to the list.

Until next week,

Romeen

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