This was a big week. After changing the name of this newsletter a couple weeks ago, this week I launched the next evolution of my work, as a leadership coach for entrepreneurs.

Hi, I’m Ryan. I’m a leadership coach to entrepreneurs.

I work with amazing humans every day to build the company of their dreams and grow into extraordinary leaders.

I know about the highs of running a company.  I’m a 3x founder, having scaled to over 11-million users across 45 states.  As CEO I raised over $20m from leading venture capitalists, built a team of nearly 100 world-class employees, and acquired or partnered with nearly a dozen companies.

And I know about the lows.  I know about losing your biggest customer.  The fear of missing payroll.  I know about going to bed crying, wondering how you’ll survive.

I’ve been there. I know what it takes. More importantly, I know what it takes out of you.

I’m here to help.  If you think you might like to work together,
let’s chat.

I’m excited, nervous and a bunch of other emotions to formalize what has to this point been an informal coaching relationship with some amazing entrepreneurs. But thanks to some coaching of my own, I’ve decided that I can make the biggest difference by taking the plunge, and working directly with entrepreneurs on their “inner game”.

Entrepreneurs are the change agents that steer our world, and by helping entrepreneurs become transcendent leaders I hope to help these amazing humans to change people’s lives, and our world, one company at a time. I am honored to be a part of the journey for some amazing people, and walk alongside them as they bring their wildest dreams to life.

Dear reader, you of all people know that starting anything takes a leap of faith, and this is no exception. I have no idea what’s going to happen, and it’s scary to take that leap. But there’s a beauty in it. As entrepreneurs, leaping is what we do.

"Living is a form of not being sure, not knowing what next or how. The moment you know how, you begin to die a little. The artist never entirely knows. We guess. We may be wrong, but we take leap after leap in the dark." -- Agnes De Mille

My goal initially is to work with only a handful of partners by design, to ensure I can dive deep with each entrepreneur on their journey to extraordinary leadership. If you are running a company and would like to know more, send me a reply to this email. I’d love to learn about your company.

Some meaty topics this week. Let’s dive in.

Unveiling the Mask of Fear

I want to talk about fear.

We don’t talk about fears in startups often, or well, but the unexamined and unreconciled fears of the entrepreneur (not to mention the leadership team and the board) are among the most common causes of a company underperforming or going out of business. It might look like founder infighting or capital inefficiency, but behind all those easier to swallow explanations, more often than not, lies fear. Raw and thick.

This is uncomfortable to write, but that’s the problem. Our industry’s inability to talk about fear directly has instead led it to fester in the background, the root cause of symptoms we spend so much time addressing.

I want to talk about fear because I learned the hard way that to move past your fears, to be free of them and gain back the autonomy that will allow you to make your best decisions, you must bring them into the light of day.

The first step in solving a problem is recognizing there is one. — Will McAvoy

So let’s do this.

The Roots of Entrepreneurial Anxiety

My parents got divorced when I was fifteen, and fifteen years later it almost killed my business.

I was blindsided when my dad told me, driving me home from school, that he was moving out. In hindsight I can now see the signals, but as a kid all I saw was my mom and dad, and their unceasing parentness. And then, out of nowhere, I saw my mom. And then, separately, my dad. At the time I played it off as though it didn’t phase me. People got divorced all the time. No big deal. But I can see now just how thoroughly that event shaped my view on life. On relationships, on business. On people leaving me.

Fifteen years after my dad moved out I was running a high growth, venture backed rocketship. We were 9 months removed from raising our Series A round, and we were flying high. In those nine months we had scaled from 15 to 75 people, we were hitting all our numbers, and everything was shaping up well to raise our series B.

I remember the specific brown of the boardroom chair in which I sat, when one of my investors told me that the investor presentation I had spent weeks on was garbage. He said nobody would buy it, and instructed me angrily to take an entirely different angle.

In that situation it’s the CEO’s job to push back. The board needs the CEO to manage investors as much as employees to keep the company on the right path, no matter the aggressiveness of the tone. Investors should challenge the CEO to ensure he’s considered everything, but they should not dictate strategy. I knew this even then, but I didn’t push back, because fear took over.

The insidious influence of fear in the startup world

I remember the wave of shame hitting me. A bodily rush of heat and pressure that hit my chest and turned me from a competent CEO to a defensive little boy, scared that his father would leave him if he didn’t do what was asked. That fear, triggered without warning, whiplashed me into a 180-degree turn in the way we were going to market. Regardless of our momentum and all the reasons to stay the course, my investor’s directive triggered my (at that point unexamined) fear of my father leaving me, and that fear overrode my fiduciary responsibility with a compulsion to do what was asked.

None of this happened at the level of conscious awareness. Consciously I simply found myself executing a new plan that I supposed was the right one because the investor was so convinced. I was blind to the fear driving the decision until much later.

So I changed the pitch to what the investor wanted. And, naturally, because I didn’t believe in the pitch and it didn’t fit our business, the investors I pitched didn’t believe it either. Our raise failed, and we ended up closing a bridge-round with our tails between our legs. It took us years to recover.

We can call this poor leadership. Bad board management. But those are just the symptoms of unexamined fear.

“When an inner situation is not made conscious, it appears outside, as fate.” — C.G. Jung

Although we rarely talk about it, I’ve learned from working with entrepreneurs that I’m far from alone. We all have a topology of fears in our psyche, little landmines that when triggered throw us into reactive, fight or flight mode, causing us to make bad decisions in an effort to stay “safe”. You see this all the time. Think of how many times you’ve seen someone exhibit one of the following:

1. Flinching in a negotiation

2. Flat investor pitches

3. Perfectionism, or failure to ship

4. Defensiveness, or blaming

5. A need to be “right”

6. Taking credit or sharing blame

7. Being uncoachable

8. Underhiring key direct reports

9. Burnout

10. You can come up with so many more.

All fear based. Mostly unexamined. We can see it in others easily (why can’t they just be honest with themselves and deal with it, we wonder) but we struggle to see the same thing in ourselves. This is a problem, because if we won’t look at our fears, we can’t manage them.

It’s one thing to ignore or try to push down your fears in daily life. The worst that can happen is you mess up your own life. But for founders, ignoring this risk can mean the difference between successful outcomes and failures, not only for us but for all the people counting on us. Once we’re aware of this, like any other risk we have a fiduciary responsibility to do the inner work to mitigate it.

Confronting Fear in Decision Making

So what do we do? In short, we look at the fear directly and talk about it openly. In this way we can learn the texture of our own personal fears and manage them consciously.

First we look at it. By understanding our own topology of fear we know our likely triggers, so when we find ourselves suddenly overwhelmed by a rush of dread when we find out our runway has been shortened by half, we can develop the skill of seeing the fear, experiencing it fully, and letting it go. This skill alone — sitting with discomfort until you can respond rather than react — is a superpower.

Then we talk about it — as fear itself, the cause, not as one of the many symptoms listed above, more palatable though they may be. Through extensive work with my own coach, I’ve learned that simply talking objectively about my fears goes a long way. Unexamined, fears take over at the worst moments and we say we “had a bad day,” or that we were “off our game,” but under a microscope we can see that fears are just predictable, cause/effect processes. Fear is a reflex. Seeing this demystifies them and lessens their influence.

For those brave enough to do the work, the best bet is to do this with a trained professional, which is one reason why so many venture funds are funding mental health programs and coaches for their founders. As in my case, oftentimes we’re too close to see the way our decisions are being made so it’s helpful to have an outside perspective to help us see what’s going on. Doing this, helping founders navigate their fears consciously to enable authentic leadership and great decision making is one reason why I coach.

It’s uncomfortable, but we need to begin to talk about fear as an industry, openly and without stigma. We need to treat it as a business risk to be managed, rather than a weakness to be shunned. “Ignoring it and hoping it goes away” is not an acceptable strategy for competition or technical debt, nor should it be for fear.

Until we begin to talk about fear for what it is, and work to proactively manage the risk that it poses to our companies, founders will continue to struggle silently. Companies will fail unnecessarily. And we will call it lack of innovation or bad board management.

Overcoming Perfectionism: A Startup's Struggle

One of the places I’m most confronted by my own fears is in writing. I tend to refer to this type of fear as writer’s block. Or standards. Or fixing it before I move on.

This type of fear is really perfectionism, an excuse to keep your work hidden so it can’t be judged, and it crosses creative disciplines. In startups, this type of fear prevents many good products from being shipped until it’s too late.

The hardest thing about writing, for me, is facing the blank page. — Octavia Spencer

If you’re not embarrassed by the first version of your product, you’ve launched too late — Reid Hoffman

Writing has been around for many thousands of years longer than startups, so fortunately founders can manage this fear (once they recognize it) with a writing technique. I’ve used this technique since college, and I can personally vouch for its efficacy.

The short version of this technique is the following: Write when you’re writing, and edit when you’re editing. And never mix the two.

The longer and more colorful version, which uses the creative archetypes of the Madman, Architect, Carpenter & Judge to describe the issue, was stated best by Betty S. Flowers. Some highlights below (although I encourage you to read the whole):

"What happens when you get stuck is that two competing energies are locked horn to horn, pushing against each other. One is the energy of what I'll call your 'madman’, (who) if really let loose, could turn out ten pages an hour. The second is a kind of critical energy-what I'll call the 'judge.' He's been educated and knows a sentence fragment when he sees one, but for all his sharpness of eye, he can't create anything.

"So you're stuck. Every time your madman starts to write, your judge pounces on him.

Whatever joy there is in the writing process can come only when the energies are flowing freely-when you're not stuck.

"And the trick to not getting stuck involves separating the energies.

The creative process is the creative process, whether writing or business building. Perfectionism is a particularly seductive kind of fear, which kills novels and businesses alike. Once you recognize it for what it is, here’s a technique you can use to transcend it.

Strategies for Fear Management

Managing fear is not the only underdeveloped skill in the typical entrepreneur’s arsenal. Self-awareness in general is also surprisingly underdeveloped in leaders. A study of 5,000 leaders done by the Harvard Business Review found that only 10-15% of leaders actually fit the criteria of a self-aware person. Further, they found that most leaders, while they understand the importance of self-awareness, have no idea how to develop this skill.

That’s a topic for another newsletter, but one particularly interesting finding among many from that study is that self-aware leaders tended to ask more “What” questions than “Why” questions.

As it turns out, “why” is a surprisingly ineffective self-awareness question. Research has shown that we simply do not have access to many of the unconscious thoughts, feelings, and motives we’re searching for. And because so much is trapped outside of our conscious awareness, we tend to invent answers that feel true but are often wrong.

So if why isn’t the right introspective question, is there a better one? My research team scoured hundreds of pages of interview transcripts with highly self-aware people to see if they approached introspection differently. Indeed, there was a clear pattern: Although the word “why” appeared fewer than 150 times, the word “what” appeared more than 1,000 times.

Therefore, to increase productive self-insight and decrease unproductive rumination, we should ask what, not why. “What” questions help us stay objective, future-focused, and empowered to act on our new insights.

I’ve found that our brains are very effective question-answering machines. Which means you must be very conscious of the questions you ask, because your brain will answer them.

These findings, counterintuitive as they may seem at first, actually provide very practical, actionable advice for overcoming adversity:

When you find ourselves or your business stuck, if you ask “why am I stuck?” your mind will give you the answer to why you’re stuck. And then you’ll stay stuck.

Better to follow the example of 1,000 conscious leaders and ask instead, “what is stopping me?” You’ll get an answer, and then you can go address that thing.

Maybe it’s procrastination.

Longtime readers know my love for David Whyte. Since a theme of this week’s newsletter has been managing fear and stuckness, I thought his poem Start Close In would be a fitting close:

Start Close In

by David Whyte

Start close in,
don’t take the second step
or the third,
start with the first
thing
close in,
the step
you don’t want to take.

Start with
the ground
you know,
the pale ground
beneath your feet,
your own
way to begin
the conversation.

Start with your own
question,
give up on other
people’s questions,
don’t let them
smother something
simple.

To hear
another’s voice,
follow
your own voice,
wait until
that voice

becomes an
intimate
private ear
that can
really listen
to another.

Start right now
take a small step
you can call your own
don’t follow
someone else’s
heroics, be humble
and focused,
start close in,
don’t mistake
that other
for your own.

Start close in,
don’t take
the second step
or the third,
start with the first
thing
close in,
the step
you don’t want to take.

I hope this hits home for you.