Full heart , clear eyes, can't lose

How paying our emotional debt can be the secret to sustained success

Welcome entrepreneurs. I’m so glad you’re here.

Before we dive into this week’s newsletter, over the next two weeks I’ll be (virtually) visiting a few cities, discussing the dark side of crush-it culture with entrepreneurs. Here’s a bit about the talk:

"Crushing It" has become a way of life for many startup founders.  Regardless of the details of the business, presenting an image of success and competence has seemingly become a critical part of leading a startup, particularly in attracting talent and raising capital.  But "Crushing It" also has very real consequences.  After raising $21m and scaling his company into a market leader reaching nearly 20% of all US high schools, VNN founder Ryan Vaughn reveals the very human costs of "Crushing It," and how a founder's persona of success can make it exponentially harder to succeed.

Two of the stops, listed below, are open to the public. They’re virtual, and they’re free, so you can attend in your pajamas.

If you’re interested in the topic I would love to see you there. Click on the links above for tickets.

Thanks to Invest Detroit VC and Startup Grind for holding the space.

Now then, let’s dive in.

Full heart, clear eyes, can’t lose

According to Ben Horowitz, co-founder of A16Z, most successful companies will experience five WFIO moments in their lifetime. (WFIO is an acronym for “we’re fucked, it’s over.” And if you’re building a company, you know exactly what I mean.) As much as strategy and tactics, it’s an entrepreneur’s resilience in those moments that separates the successful companies from the rest.

I use the word resilience intentionally, deliberately drawing a distinction between it and its close cousin: persistence. You might say tomato/tomahto, but in my experience, when compounded over time a habit of practicing resilience vs persistence can lead to dramatically different outcomes.

You can sweep your stuff under the rug for company, but if you do that too much without cleaning it up afterward, you’ll eventually trip over a lumpy ass rug

The cost of persistence: Emotional debt

Many founders, when they hear the word resilience, think of a stone-cold badass, shrugging off the mightiest challenge and moving forward. A scarred warrior, blood spattered and exhausted, gritting through the pain and lifting up his spear once more. This ignoring the fear and pain and pushing on by sheer force of will is actually persistence, which, while undeniably effective in the moment, comes with a heavy cost — what I call emotional-debt.

As decades of psychological science will attest, shoving down your emotions like this in the name of progress doesn’t make them go away. The repressed emotions stay with you, causing mental and physical ailments and creating a field of emotional landmines just waiting to be triggered.

Like companies incur technical debt or people debt, leaders incur emotional debt every time they push down an emotion to get shit done. Like other forms of debt, a little emotional debt is manageable and can even be useful when incurred consciously and subsequently paid (switching into ultra-logical mode in a crisis, thereby incurring debt from the emotions you aren’t allowing yourself to feel, can be a great decision as long as you take the time to process when the dust settles). But perpetually carrying emotional debt can cloud a leader’s judgement, and lead to significant issues.

Think of a time when you’ve seen (or been) a leader bite an employee’s head off for asking a question. This type of disproportionate reaction usually indicates that the objection triggered a deeper feeling, something unexperienced from a previous incident.

Or consider a leader delaying a bold-but-smart decision to “get more data,” and missing her window of opportunity. It’s hard enough to make a tough call with insufficient data alone, but compound that with a heavy balance of repressed fear and it’s amazing how creative our excuses to delay can be. We can trick even ourselves.

Or think of the dreaded burnout — a topic about which I personally know well. I “overcame” my fear and worry and anger for years by each time telling myself to get back to work. I thought I had a superpower. That I could will myself past the unpleasant stuff with no repercussions. And then it all came due at once and I had to take a sabbatical to get my head right.

It can be a good decision to max out your emotional credit cards by persisting in the heat of a crisis. Just remember that debt compounds, and if you don’t pay your bills don’t be surprised when the creditor comes calling to break your kneecaps.

Resilience is intentionally feeling, and then acting

Resilience is different. Resilience is supple. It’s the way that skyscrapers flex in the wind, moving with every last gust before returning to center. It’s a Judo black belt using the force of an opponent’s strikes against them, or the way water adjusts to every obstacle placed in its path, but never stops flowing. Resilience is intentionally feeling the emotions of the situation without changing them, all the way through to completion, and then moving forward with a clear head.

It took me a long time to learn the difference, and I still practice it consciously every day, but as counterintuitive as it is to lean into your negative emotions, to consciously choose to feel the texture of your fear and resist the urge to fix it, I’ve found that the results are profound. Various studies have found the same. By practicing resilience, processing your negative emotions in real time with curiosity rather than resisting them, you allow them to move through you and complete. And in doing so you pay the emotional cost of your current WFIO moment in cash, and can move to the next one with freedom and balance.

“Maybe the only enemy is that we don’t like the way reality is now and therefore wish it would go away fast. But what we find as (meditation) practitioners is that nothing ever goes away until it has taught us what we need to know. If we run a hundred miles an hour to the other end of the continent in order to get away from the obstacle, we find the very same problem waiting for us when we arrive. It just keeps returning with new names, forms, manifestations until we learn whatever it has to teach us about where we are separating ourselves from reality, how we are pulling back instead of opening up, closing down instead of allowing ourselves to experience fully whatever we encounter, without hesitating or retreating into ourselves.” — Pema Chodron

Coach Taylor from the amazing Friday Night Lights was onto something, he just had the order wrong. Focus first on keeping your heart full. Feel everything, and let it pass through you. Then your eyes will be clear, and you can’t lose.

What all CEOs feel, but many don’t process

Despite the image you may have of what a “successful” leader looks like (which I’ve tried to dispel here), all CEOs feel things. Intense things. Startups are called emotional rollercoasters for a reason, and they carry an emotional cost.

For those of us who have trouble figuring out which of those emotions we might be repressing, below is a revealing and outstanding dive into some of the most common things CEOs feel but don’t process productively.

May you find that one that resonates. The one that you read and your stomach drops. And may it begin for you the enlightening process of processing.

Raising money: Here’s some simple, but powerful, advice

I’ve been helping out an early stage angel fund over the past few weeks, and in the process have found myself looking at detailed numbers on pitch decks. I’ve found myself giving the same advice over and over again, so I figured I’d leave it here.

For those of you building investor materials, something to consider:

  • If you show Excel-level data, you will get Excel-level questions.

  • If you show Powerpoint-level data, you will get Powerpoint-level questions.

Worth considering what kind of conversation you’re hoping to have with your prospective investor, and rounding your numbers accordingly.


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