From Death to Stock to Death to Stress
No. 04
David Sherry
from With Good Company
Clayton Fuller
Clayton Fuller

I have watched David Sherry live two lives. The first as the founder of Death to Stock, which began as a small experiment and grew into a global creative platform for designers and creators everywhere. The second began when the ambitious pace that many of us know caught up with him, leading him to reevaluate his identity and redesign his life.

Today, he works with founders and leaders to navigate transitions of their own, from times of intense growth to moments when old motivations no longer work. In this written conversation, David shares his thoughts on identity, energy, and the questions we all have to consider for designing a creative life — how we define success, where we place our attention, and what it means to build something without losing ourselves in the process.

IRL Escapism
David Sherry
CF
Can you tell us a bit about the experience and process of founding Death to Stock?
DS
I was trying all types of different projects. Before Death to Stock (DTS)??, I had failed at a few business ideas through college.

Just after school, I was flexing my creative muscle and trying weird experiments that were more like art projects. I wanted to help brands create better visuals for an internet (circa 2012) that was shifting towards social photo feeds like Instagram. It started as a newsletter where Allie, my co-founder, and I would share photos we took and send them out for free for people to use in their projects.

Looking back on the business through a different lens (pun intended), I think DTS was built on solid core values like having an abundance mindset (the photos were freely shared) and wanting to promote individual artists (eventually we would hire and feature others to create the photos). The newsletter grew pretty large, eventually to 500k+ subscribers, and people always ask how that happened. I think it came from consistent generosity, doing things that didn’t scale, and being creative about how we built our community.

The joy of building DTS was in the creative experimentation that led to the organic growth of the community. The model itself paired brands and creators who were hungry for beautiful visuals with artists who wanted to do their best work. It was elegant in that brands would pay us, we would pay artists, artists would create unique new work, and those visuals inspired new work from the brands. It formed a virtuous creative loop.
CF
When you look back at the Death to Stock years, what kind of ambition were you running on or towards?
DS
This is such a good question because the thing that creates companies is the ambition inside the entrepreneur that drives them forward. And a lot of that ambition comes from pain and struggle.

I started the company with a strong ambition to be an entrepreneur and a founder. I remember fully committing to this path of working for myself. I even got a
tattoo related to the Icarus story?? to commemorate the decision. It was a line in the sand that I drew for myself (and literally on myself, on my left arm). Since that decision in 2013, I’ve worked for myself and myself only.
Since that decision in 2013, I’ve worked for myself and myself only.
Now, some of the drive I had was culturally influenced. Startups were becoming popular. I realized after running my own business that founding a company can be just like following the corporate ladder. It's just a different pathway culturally laid out for you with its own set of rules. It's kind of funny to think you’re being rebellious and different, only to realize it’s a path with its own cultural norms to conform to.
CF
This reminds me of that quote from James Baldwin about how we think our choices and experiences are unique but we’re living within similar patterns — and some of those can feel like a trap.
DS
Happily, I bootstrapped the business, so I never took any venture or angel funding. That gave me a lot more control over my decisions. I see founders all the time who feel trapped or in a pressure cooker because of the funding they’ve taken. The benefit of venture capital is that you’re signing up for a structure designed to produce a specific type of outcome. The downside is that the incentives of those who fund you can push you into decisions that might be at odds with what you actually want. A lot of my work now is supporting founders through their first-time journey of growing a company, and essentially being a partner at the table with them as they navigate those challenging moments and decisions.

My transition away from Death to Stock came from awareness of that ambition changing. When you pay attention to what’s driving you, and get more conscious about it, you can get a pretty good idea of where your next opportunity to grow and expand is. I was able to go my own way because I had full freedom and autonomy. I was able to listen to what I was wanting and where my growth was. That pathway took me away from Death to Stock and was, of course, influenced by my own unique set of experiences.
Raw Element
Raw Element
CF
If I recall correctly, part of that transition was fueled by a bad case of shingles?
DS
I wrote a blog post about a decade ago called "The Smack from the Universe." The basic idea is that if we don't listen or pay attention to the signals presented to us — the ones that show up to teach us something — those signs will get louder and louder until we finally pay attention.

Getting shingles was a wake-up call because I don't think I truly understood the level of stress that I had been operating under. I mean, every entrepreneur understands the feeling of waking up in the middle of the night in a cold sweat. And in this day and age, there are so many ways to avoid feeling what you're truly feeling.
And in this day and age, there are so many ways to avoid feeling what you're truly feeling.
Something rarely talked about is the stress, pressure, coping, or even illness going on behind the scenes with founders that people don't know about. In my case, things looked like they were working, but internally I was running on fumes. My smack was getting shingles at 26. My understanding is that shingles only happens when your immune system is completely down, something far more likely to happen to someone in their 80s.

I wasn't paying any attention to my internal operating system. I was so focused on the outside — how I was seen by others or whether I was reaching my external goals — that I avoided truly being aware of what was happening on the inside.

Lucky for me, this painful experience where I couldn't work for a month put me in timeout. It kicked off many different shifts in my life, some of which may have already been brewing, and it ultimately led me to grow and expand as a person and an entrepreneur. That growth led me to shift away from understanding myself as an intellectual, a mind and a labeled identity, to being a whole person with a body and emotions.
CF
You’ve clearly lived in the identity of being a founder. What helped you see yourself as more than your work?
DS
If I had one message for founders, it'd be that you are more than an entrepreneur.

Of course, this is obvious. Yet it's actually not so obvious to many people who are struggling within the stress of their business. I’ve been there so I get it. And yet I also know how much more there is out there. A company is just a single vehicle, a single aspect of your life. You have a body and a soul, you’re in relationships, and you have creative parts of you that don’t fit into the founder box.
You get to build a life that, as Robert Fritz says, is “art.”?? Your life is your art project. If you don’t care for your physical body you might find yourself in what Tony Robbins calls “ultimate failure,” which is “success without fulfillment.”

The second commitment I made to myself after that first commitment to be an entrepreneur was to commit to building a life rather than just building a business. Having a great life to me means having many successful and great days. A great life does not exist in the future. It only exists now, today, and day by day after that. Once you start focusing on the present instead of just the future, you make space for your whole self instead of just the self you are trying to create for something external.
Aura
La Calma
CF
When you’re helping people design their lives, not just careers, what shifts have to take place?
DS
One thing I do with the founders I work with is help them build more diversity of experiences into their day-to-day lives. Sure, we measure success through external metrics like revenue or income, but the metrics I care about most, honestly, are moments like when a founder tells me they took two weeks off with their family and really enjoyed it. Or that they're spending more time with their kids. I even have a founder who's working toward his black belt in karate.There's a point in coaching where most of my clients go from solving problems to enjoying new experiences. I’ll have a client say, “David, I feel bad coming to our session today because I don't have any problems to bring you.”

I laugh when they tell me that, because I basically tell them, “What! You think coaching can't be about something good? What if we use this space to get really excited together about all the opportunities in front of you? I'm always available if there's a problem or challenge you're facing to work through it with you. But what if we spent a bunch of time on creating more goodness, more fun, more creativity in your life? Who says we have to talk about problems?”
I'm going to be doing this for the rest of my life?
I’ve realized that a lot of founders (and ambitious people in general) don't really know what it's like to feel really, really good. People often get really uncomfortable when things feel good because it's not what they used to be driven by.

A lot of my work is helping people through a transition in what's driving them. The sneaky thing about creating success is that you often start wanting something different. I mean, once you reach a goal you set, you typically want to set a new goal, right? Entrepreneurs don't realize that in reaching their goals and in creating success, they create a new challenge, which is that the old goals no longer excite them. The previous version of the company no longer excite them. This is now obvious me and impossible to get around. If you spend five or ten years building a company, I can guarantee you that you will be a different person at the end of that five to ten years. And if you're a different person, you're going to want different things.

People tell me, "I'm going to be doing this for the rest of my life." This is a mostly naive statement because it rarely happens. Too much changes. So it’s helpful to know that most times a company is a phase of your life (5-10-15 years) and you will maybe do that multiple times.
CF
Through the lens of the coaching you do, what mistakes or misconceptions do high performers have about stress or ambition (or related)?
DS
I try to help founders and CEOs understand that life’s “scorecard” isn’t one-dimensional. Success is not tied to any one metric or goal. Success is something you judge yourself on. There are many ways to evaluate your own success and it’s really personal. You can feel successful before you are “validated” for that success, which runs counter to how many people are conditioned to think.

This becomes obvious to people when they look backwards. For some reason, when you look forward, you anchor to one type of success metric, and when you look back, you anchor to another. For example, looking back at my time spent in college, I don’t fondly remember getting an A in a class or on a test. I remember the teacher who really moved me with her lectures, or joking around with my friends. I might look back fondly on how much studying for a test sucked, yet I don’t even remember the grade part of it.

Another thing is that there are so many things telling people to focus. The problem with extreme focus is you lose perspective. You see a dot and miss the painting. I like to enjoy the whole painting and each of the dots.
IRL Escapism
A simple heuristic is to think about success in two ways: Your inner world (your feelings) and your outer world (your results). You can:

A. Feel great inside and have strong results outside (best place to be)

B. Feel bad inside but still have strong results outside

C. Feel great inside even if your results aren’t strong yet

D. Feel bad inside and also have weak results outside (worst place to be)

Most people index more toward the outer world than their inner world. Yet I’ve found that the inner experience makes up probably 70% of how you experience life. I’m not saying quit and become a monk (C). I’m simply trying to shift people a bit further into that inner exploration.
CF
What’s a counterintuitive principle or habit you teach your clients that they resist at first — but ends up being the unlock?
DS
I’m surprised how often founders don’t see their excitement and enthusiasm as their compass. Building a project or business takes a ton of energy, so if you build things you’re energized about, it’s much easier. It’s a competitive advantage. When I ask what they’re currently most excited about they usually look at me like that’s not a viable way to do planning. If your next quarter isn’t exciting on some level, why do it at all? People build half-hearted features or services that they think they should create. We all know when we’re really in and into something or not. Don’t cheat yourself, keep adjusting and searching until you find the thread that truly lights you up.

If you as the founder are genuinely interested and excited about something I believe it’s much more likely to be successful.

Another counterintuitive idea is that every problem you have in your business is also an opportunity. It’s beyond solution seeking. Everything you’re frustrated with, every issue you want to hide from, every area you’re challenged by is where growth is possible. Say you’re embarrassed by your customer service. There are long wait times, customers are frustrated, and you’re getting tons of negative feedback. You want to hide from this problem, or complain. You let it grow because it pains you to look at it.

Well, next quarter, why not create a world-class customer service department? Why not go beyond getting this to baseline and make customer service a core reason your brand is known? When something is poor quality, or frustrating, it usually means there is a good amount of opportunity there.

When you look at your business through this anti-fragile lens, every liability can become a strength. Wherever there’s frustration, there’s massive opportunity. So instead of complaining about it, create a better vision for it, a vision where that problem not only no longer exists but is an area of pride and joy for you.

One thing I teach entrepreneurs is to look each quarter for the parts of their business that are ready for “better.” As a practice, turning challenges and frustrations into opportunities is a pretty good recipe for growth.
CF
I’ve heard you say, “most people don’t have a personal business model.” What does that mean in practice, and what guidance would give someone to create one?
DS
What I mean is that you have to know how you create and capture value, and you have to be clear about how that works for you. It’s part philosophy and part system.

I can start with myself. One philosophy that I have is “always be exiting.” It means I don’t wait and pray for some future exit to give me wealth. I don’t plan to make all of my money in one go, at some future point in time.

I want to sell pieces of equity all of the time. Some might say that’s terrible advice. Their business model might be, “I’m going to compound this equity for 20 years and then have a massive exit.” That might work for them, it doesn’t work for me. I want to get rich slowly one small to mid-size sale at a time. As a bootstrapped founder, that mentality works for me.

My coaching business also has a model behind it. It’s not about maximizing cashflow — it’s about investing. I eventually realized I couldn’t earn more than I could grow through investing. I’d rather give thousands of other people my money, through equities or startups, and let them work on growing my wealth. So any cashflow from coaching gets reinvested into startups, equities, or crypto. I’m also married. My wife has a more traditional job. Together, we have a business model where I take more risk and she has a steadier income. It’s a barbell model.

If I had to make this more actionable, I’d ask, “How are you actively building wealth right now?” I just want people to have a clear idea and plan for how they capture that upside now or in the future.
CF
What’s one thing people think is “self-care” that’s actually making them more anxious?
DS
Ha, I love this question. I mean, let’s say you’re hardcore and working 15-hour days. And you’re drinking tons of coffee. And you’re doing Crossfit. Oh, and, because everyone is saying you need to be doing this too, you’re cold plunging into 45-degree water.

Might it be that you’re body is getting a bit… overloaded? Rather than doing everything people say is “good for you,” it’s better to be more simple and intuitive about these things. People don’t often have a great relationship with their bodies, I certainly didn’t.

Self-care shouldn’t be this “special” thing you do. Self-care basics really are the basics… sleep, diet, and exercise. All three require time and presence. Can you unplug an hour before bed? Can you create enough space to enjoy a healthy meal slowly? Self-care is being intuitive about what you’re needing. It’s knowing when to skip a workout, and it’s knowing when to show up even when you don’t feel like it.

A big challenge people face, especially high performers, is unplugging from work and being present with their relationships. Relationships are also self-care. Connection is probably more important than diet or exercise for your longevity, as crazy as that sounds. I recommend finding places where you can be with people who bring you back into presence and back into equilibrium. When you have experiences where community makes you feel more at ease, it creates a strong foundation to build on.

If self-care was a pyramid, I’d put connection at the bottom, and build up from there. And I’d bet most people have it the other way around.
Raw Element
By Water
CF
What investments have you made in your own personal development?
DS
For starters, I decided to literally invest in my development. I made a rule to invest more every year than the year prior in my own growth.

After that, it was about learning “how” to map my growth trajectory for myself. Therapy and coaching can help you understand how to guide and direct your growth consciously. As you get coaching or therapy, you should become a better coach or therapist to yourself. If that isn’t happening, you’re just outsourcing your agency.

I’ve always been curious about how coaches or therapists were doing what they were doing when working with me. The more aware you are of where you are in your growth trajectory, the better. Funny enough, astrology is a good basis for this. People like astrology, regardless of it’s veracity, because it gives you a sense of context for where you are and where you’re going. So, what if you could become your own astrologist? You can.

People don’t often realize this, but psychology is technology. It’s what John Vervake calls "psychotechnology." Most forms of therapy are simply new psychotechnological breakthroughs. There are some really incredible tools and tech people have built for your psychology, it’s a trip.

So the takeaway is that you can get better at working with your own hardware and software. The good news is that people have been exploring and working at this for thousands of years. Religion and spirituality are
Lindy (time-tested).?? If this sounds interesting, and you’re wondering where you can start, I wrote up a list of good wisdom maps.
CF
You’ve become almost monk-like about energy. What does managing energy actually look like?
DS
You know, I’m still trying to figure this all out. I’ve had many peak experiences in my life, and what excites me is the question: What if you could have peak experiences from day-to-day moments, not just during some future perfect moment on vacation watching the sunset?

If you can have peak experiences on a regular basis, that to me is a great life. Being fully engaged, being on purpose, being light and creative, I seek all of these things. As you seek something though, it can become elusive, so you have to watch for that. You never want to pursue something too directly, especially when it relates to feelings or experiences.

There’s physical energy where, again, it’s the basics: sleep, diet, exercise. Score yourself 1-10 on each of these, and see if you can bring a score in one area from a 3 to a 6 or a 5 to a 9.

Then there’s your essence, the true energy of who you are. This is your enthusiasm, your presence. This is more than the biological hardware, it’s how your software is running day to day. The truth is you can change your energy on a dime. This is what spiritual gurus like Ekhart Tolle talk about for hours and hours and hours. By shifting your present awareness, you can immediately change your experience. Have you ever been at a dinner with a friend, or sitting on a porch, and suddenly drop into a deeper conversation — like the lights dim and you focus more intently? Or gone through a breakup and found the rawness bringing you more in contact with your emotions and the emotions of others?

You can manage your energy in an infinite diversity of ways. You can play with your energy. Making this practical, what would it look like to show up to your next meeting with more joy or curiosity? What if you started the meeting with a joke or something you’re grateful for? What if you asked a question that was deep? Or shared something vulnerable?

I heard a genius idea from someone who’s worked with some of the top musicians in the world about being present. He said, “The idea is not to not be distracted, it’s to let yourself be distracted. Use the distraction to focus you.”
CF
Appreciate you sharing so generously. Last question, what are some actual tools, systems, or apps you rely on to manage your energy?
DS
My bed. I don’t use an alarm clock, and I try to be asleep by 9:30.

Questions. I get curious and ask questions. I try and avoid forcing a question, or asking a “stock” question. I let questions hit me. I sit patiently until a question forms itself that wants to be asked.

Apple Notes. I write down notes all the time, I rarely look back at them. I jot down lists and notes frequently. Lots of times the lists I make are “things that make me feel good” or “things to avoid.” I just write and re-write those lists and sometimes they change. These inform my habits. Some things on my latest list of things that make me feel good — eat an apple or smoothie for breakfast, don’t like or comment on a post (call the author), call mom, budget every month.

Reader by Readwise. I like this app because it allows me to “save” articles for later. I’m easily distracted, and I imagine you feel the same when it comes to seeing emails, newsletters, posts, podcasts, etc that pop up on your feed. Rather than click and read them now, I save them for later.

Oh, it’s worth noting that what hasn’t helped is other people’s productivity systems. The only ones that work for me are the ones I invent for myself.
Launching Comet with Perplexity
No. 05
Aaron Marks
from Studio Freight
Category