“I’m Winston Wolf. I solve problems.” — Pulp Fiction

I had a conversation recently with a founder I’ve been coaching for a while. Nothing dramatic happened—no big exit, no new venture just launched.

But something was different.

He Was Showing Up Differently

He sounded lighter. More clear. He was describing conversations he used to dread that now felt easy. He was building relationships, asking great questions, and genuinely enjoying it. Not performing—participating.

He told me about:

• Hosting a major industry event and enjoying being recognized for leadership

• Connecting deeply with people at a wellness startup launch

• Taking in two hours of a live Eckhart Tolle presentation with no notes, no urgency to “get everything down”

• Exploring franchise opportunities—not to escape his day job, but out of real curiosity

• Giving up alcohol, not with fanfare, but because it just made sense

• Reworking his schedule to include tennis, yoga, strength training—and sleeping better than ever

Leading by Letting Go

He also told me he’s ready to step away from the business he sold to private equity—his “day job,” as he called it—with clarity, not bitterness. He’s actively developing his team, handing them more responsibility, and watching them thrive without him in the room.

None of this came from trying harder. It came from letting go of the pressure. The pressure to prove, to perform, to control every outcome, to find and solve every problem.

And when that pressure dropped? Possibility showed up.

He’s not “on fire.” He’s not “crushing it.” He’s not selling someone on his 7-step plan.

He’s just building a life that actually fits him now—and noticing what’s worth leaning into.

A Subtle but Life-Changing Shift

Sometimes the shift we need isn’t tactical. It’s internal. It’s not about having a plan. It’s about having space.

This shift doesn’t just happen to founders. It can happen to anyone.

When you are looking for problems, you find them.

When you are looking for possibilities, you find them, too.

If that’s a shift you’d like to explore, there are two ways to spend two days getting exposed to viewing from possibility.

First, as a one-on-one retreat. Second, as a group event in Denver October 20-21.

If either of those possibilities appeal to you, like this post so more people can see it, and send me a DM.

“I’ve suffered a great many catastrophes in my life. Most of them never happened.” — Mark Twain

“Be fearful when others are greedy and greedy when others are fearful.” —Warren Buffet

Recent events have convinced many people that we are headed for a recession or worse. That it is time to hunker down and play it safe.

Yet time and time again, the worst economic times have led to the biggest opportunities.

It’s Not About What You See—It’s About Where You Are Looking From

I confess I have no idea, yet, what the big opportunities are in this time of incredible uncertainty.

But here’s what I do know. They are a lot easier to see if you are looking for them.

If you are convinced that doomsday is coming, then by all means build a bunker. Stop living life. But keep in mind that both Uber and AirBNB came out of the financial crisis of 2009. And there are startups from COVID times that continue to thrive. I know for me, it was during COVID that my access to and focus on founders became much more clear than it had before, and I have never looked back.

I now look at COVID as a turning point for my business.

Time and time again there have been turning points when things looked most difficult.

Will this be a turning point for you?

If This Was the Biggest Opportunity You Had Ever Seen, What Would You Do?

Because here’s the secret. Every market creates winners, and down markets create some of the biggest.

In every conversation I’ve had with a founder in the past few weeks, they have come away convinced that their biggest problem is not a coming recession, but taking advantage of all the opportunity that both exists and is coming.

Would you like to see that, too?

Reach out and let’s talk.

Remember, you don’t have to know right now. You just have to know that you can see it if you look for it.

Every leader I work with has a routine (conscious or unconscious), and the results that they get are directly related to the habits that they have established.

I want to share a few things that have worked for me, with the hopes that if you make even one change in your existing routine, it can have a massive impact on your results.

It All Starts with Your Physiology

If you are running around in a panic, you are not going to create good results.

So the question I like to start with is—who do you want to be?

When they get past the goals, financial, business, and otherwise, most people I talk to say things like—

— I want to be a person who sets and achieves goals with ease.

— I want to be more calm and present.

— I want to make better decisions.

— I want to have better relationships.

— I want to be more creative and engaged in the work that I am doing.

— I want to live a life of minimal regret.

All of these start with your physiology.

You can’t do any of these when you are consistently in fight or flight. So having a routine that minimizes the time you are in that state will pay exponential benefits.

It Must be Doable

I work with a lot of overachieving leaders. And when the topic of a morning routine or habits comes up, they often try to design the perfect routine—I’m going to meditate an hour a day, I’m going to do yoga, go to the gym, train for an ultra, etc., etc.

And like the New Year’s resolution that lasts two weeks, this approach fails over and over.

Start Small and Build

I once asked a leader to set aside one minute a day to breathe deeply. Because we had done that in a session and he had felt the impact in just that one minute.

If you get success with small things, it will reinforce itself and you will take on more. A virtuous cycle that will pay increasing dividends over time.

A Sustainable Routine that Works for Me

Here are the things that I have been able to implement and sustain over time. And a couple things that I am trying to get better at incorporating.

Meditation

I used to meditate an hour a day. For years. But it stopped working for my schedule once I started my own business. I went months without meditating at all and I noticed my reactivity was increasing in its absence.

In the past few months I started a new habit. After I make my coffee, I meditate for five minutes. That’s it. And my focus is on belly breathing, the 4×4 exercise (four seconds inhale into the belly, exhaling out my stress and thoughts, repeated four or more times) that I recently wrote about. It clears my head for whatever is coming in my day.

Journaling

After I meditate, I pull out my notebook and write for three pages, an exercise called “Artist’s Pages” first written about by Julia Cameron. But I ask specific questions—What is being called to be created by me today? What is it that my higher self wants me to know about myself today? Who do I want to create myself as today?

Once the ink starts flowing (I highly recommend that you physically write rather than keyboard), something opens up and I almost always see something about myself or the world that I did not see before. And that reinforces my understanding that each of us is literally creating ourselves fresh and new in each and every moment. There are limitless possibilities, if only we get in the habit if seeing them!

Exercise

My wife routinely goes on ten mile hikes. I confess I am much more utilitarian in my exercise, focusing on what is the minimum dose of what I need to feel the way I want to feel.

For me, that means resistance training and aerobic training. I am trying to incorporate more work around flexibility, such as through yoga, as well, but it is not as established as I would like it to be.

For resistance training, it means a simple weight working on machines and with dumbbells, exercises done to failure. I often incorporate what are called “drop sets,” which means you do a set to failure, drop the weight significantly, then do another few reps to failure again. it is intense but it works. I feel great after a workout. I can get though my weight workout in about 20 minutes and I do it twice a week.

For aerobic training it depends on time of year. I try to have it be outside—a run with the dog for 30 minutes to an hour, or cross country skiing, or carrying a weighted backpack uphill. I try to do sprints or short intervals (100, 200, or 400 meters) once a week or so for variety. Sometimes I end up doing those intervals in a treadmill but it is not my preferred approach. I do two aerobic workouts a week.

Time Outside

There is lot of research pointing to the fact that time outside helps us with both stress and creativity.

I walk outside with the dog two or three times a week for about an hour (I share dog duty with my wife—the dog gets out every day!). It can be difficult to get out sometimes, especially in the middle of the day, but I’ve found it’s a good time to listen a podcast or make phone calls, so it can serve double duty if needed. I also find that a hour walk while doing absolutely nothing else can be incredibly energizing and head clearing when I feel like there is just too much going on.

Having A Hobby

My newest addition to this routine is playing the saxophone. I first picked up a saxophone on April 6, 2023 (I sang growing up but have never played an instrument) and it has become the part of the day that I consistently look forward to the most. What I love most about it is the fact that I have to be present to have any chance of doing it well. If I have anything else on my mind, the horn lets me know, immediately.

Building YOUR Routine

Those are the elements of my current routine, and they have been cultivated over a period of years. They also change from time to time based on what else is going on in my life.

But every ingredient brings me some combination of joy and building my capacity to be calm and present with whatever else is going on in your life.

What are the elements of your routine? I’d love to hear what works best for you.

I’ve been in conversation with several founders about fundraising in the past few weeks. Each is in the process of raising, or has just completed raising, millions of dollars.

Each founder brings a different pitch to each conversation. But they also come from a different place.

And I notice that the place the founder comes from has a bigger impact on their success than the product, the industry, or the pitch.

Let me start with two examples—

Founder A is in the process of raising $25 million for his company. I ask him how it’s going.

“I’m so stressed. My calendar is not my own. I’m chasing people trying to do anything to get a meeting and then when I do get one, it ends up a waste of my time. And then I run to the next conversation, knowing that if I don’t find some money, fast, I’m not going to meet payroll. I know it’s a numbers game, but it’s so hard to keep going.”

Founder B is in the process of raising a similar amount. I ask her the same question—

“I’m feeling pretty good. We are having conversations with a few good potential partners. But we do a really good job of screening them before we get into a serious conversation so the time away from my team and doing my other work on the business is pretty minimal. We’re not there yet, but I’ve a feeling we’ll end up with someone we feel really good about.”

Two founders, two very different experiences. Why the difference?

What Else are You Bringing to your Conversations?

Fundraising can feel like an existential crisis—

It’s about the quality of my idea.

The quality of my pitch deck and my projections.

My experience. My team. How well I tell my story.

My performance.

My very sense of self-worth can feel at stake.

And everyone knows that cash is the very lifeblood of a business. If I run out, the business dies, along with my dreams of finally proving myself.

Exaggeration? Maybe a little. But does it resonate?

If it does, can you understand that when you put your very physical and psychological existence on the line, the conversation can feel just a little bit stressful?

What if there was a different, easier way?

Who’s Auditioning Whom?

Most founders I talk with think that the people with the money have the power.

Like actors auditioning for a part, they put themselves in a room with fifty other people, all more experienced and better-looking. And they try to psych themselves up to show up exactly how they think the casting director, the one with the money, is going to want them to show up.

Maybe this time they can be good enough!

But what if you’re actually the casting director? And people are lining up to see if they can please, please, please invest their money with you.

The Big Secrets

There is plenty of money. In fact, there is way more investible money than there are good ideas.

And no one really agrees on what is a good idea—only about one in ten are really going to hit no matter what.

No matter what someone tells you, they have no idea if your idea is one of the winners.

So how do they decide?

Your story. How you talk about your idea matters. Make sure it is abundantly clear why it is different, and how it wins (a big TAM—Total Addressable Market is also nice, but not absolutely necessary).

Your experience. While you can’t change this in any meaningful way, you can change how you talk about it. For example, one of my clients had no meaningful startup experience. But what he was building was actually more about starting at a scale that most founders wouldn’t dream of. And he did have that experience running large organizations. He had the experience that most mattered, even if at first it didn’t look like it.

Your confidence. If you come from a place of auditioning them, of being absolutely clear what your ideal partner looks like and what you are looking for, you will instantly become more attractive as a potential investment.

How to Be Less Desperate (Even When You Feel Desperate)

I get it.

All this sounds nice when you have a year of cash in the bank.

But what if you actually need the money, and soon?

Do your customers care if you can’t make payroll?

Your potential investors don’t either, unless they are using it to take advantage of you. (Not the investors you want.)

You still need to come from an audition mindset. You still need to find the right partner, not just any blank check, because this is the phase where the wrong partner could have a huge impact.

You still need to be one hundred percent confident. Even if you don’t know exactly how things are going to work out, you have to be confident in your ability to figure something out. In your own ability to get out of a jam, just like you have so many times before.

If you feel hesitation, breathe. Deeply. Into your belly. Slowly.

Every time you exhale, let some of that stress you are feeling out. Will it change your situation? No. But it WILL change your body’s experience of your situation, and your potential investment partners will feel that.

Your certainty becomes their certainty. Not cockiness. Not bravado. Just calm, centered confidence.

You’ve got this.

At a Crossroads?

Taking some time away, with a guide who has been there before, might be the best way to get some clarity on what’s next.

I have a couple of ways of doing that. Two days for thinking bigger thoughts. One on one or in a group.

Reach out for more details. Your transformation as a leader awaits.