My Day As A Startup Founder


By Nicolas Cole

As a startup founder, however, my day actually started late last night. I climbed into bed around 11:14 p.m., after spending two hours working on my next book. I then proceeded to roll around in bed until 12:37 a.m., my mind turning.

I woke up this morning at 7:00 a.m. sharp.

I originally had my alarm set for 6:30 a.m. but adjusted the night before when it became apparent around midnight that I wasn’t going to fall asleep any time soon. When my alarm finally did go off, I decided to forgo my usual morning shower, throw some clothes on, and get myself out the door as quickly as possible.

I don’t have an office to show up to.

My company, Digital Press, is entirely remote. In less than 8 months, we’ve gone from a 2-man operation (myself and my co-founder, Drew Reggie), to 10 full-time employees.

Over the past 2 months, I’ve been making it a point to wake up early and walk to a coffee shop a few blocks away. There’s something about getting outside as the sun is coming up that sets the tone for the day. Before I get outside, I text my girlfriend good morning, that I love her, and then spend the entirety of the walk with my phone on silent.

This is my first meditation of the day — a walking meditation.

By the time I arrive to the coffee shop, I am present. That is the primary purpose of this new morning routine, and one I’ve deliberately implemented to counterbalance the day-to-day stresses that come with a fast-growing startup. I like this coffee shop in particular because of the industrial-chic design, the single hanging lightbulbs and wire-rim fixtures, and the wall of deep green foliage outside. Here, they brew bean grounds through what appears to be a coffee bong using filtered water. It’s some of the best coffee I’ve ever had in my entire life, and every morning I try a different roast.

Despite the fact that some of our employees and clients are on the east coast, and my phone is full of Slack messages, and my email is bubbling over, I don’t check any of it until after I’ve sat in silence, had my morning cup of coffee, written a few poems in my journal, and taken 30–45 minutes to read to myself.

This is, aside from late at night, the only time I will get exclusively to myself for the next 10 hours. And in order for me to be an effective leader, it’s essential that I check in with myself, first.

Once my cup of coffee has been downed, and the sun is officially up and working, I depart from the coffee shop and head home.

My impulse is to reach for my phone and start checking messages the moment I leave — I try very hard not to do this, if for no other reason than to practice the art of “letting go.” As a founder, it can be INCREDIBLY tempting to stay glued to technology — especially when running an Internet company. Over the past 8 months, however, I have learned that my single most valuable asset is my own clarity. When I am clear, I am effective, I am positive, I am stress free, and I am productive. The more times I return back to my phone, the quicker that state fades. It is a finite resource, and so I work hard to preserve it best I can.

When I get home, I put my oatmeal in the microwave and stand in the kitchen in front of my laptop.

Now, it’s go-time.

In just one hour of being awake, my phone has filled with dozens upon dozens of messages from team members, notifications from social media, family group chat messages, etc. In a flurry, I start responding to anything that needs my attention immediately.

Everything else, I ignore for the time being.

First, I must eat.

I grab the scooper from inside my bag of chocolate protein powder and mix it into my oatmeal. I then slice up a banana and a few strawberries, and walk my breakfast and laptop to my desk. Most mornings, I am sitting down right at 9:00 a.m. and dialing in to my first call before I’ve even had my first bite. This was the price I paid for staying the full 45 minutes at the coffee shop to read this morning — I had to choose, time to read, or time to eat.

As a founder, your life becomes a never-ending cycle of these kinds of pro/con decisions.

This morning was no exception: I dialed our newest employee on Skype, dove into working through some training materials (while I snuck bites of breakfast), and then at 9:30 a.m. jumped to an onboarding call for our newest client.

I kicked things off, made the introduction between Client and his Digital Press Editor, and then put myself on mute while eating breakfast and taking notes on feedback I could provide the Editor to help him improve on future calls.

At 10:30 a.m. the call wrapped up. I received a Slack message from my co-founder:


We catch up for 30 minutes. He tells me about a meeting he just left in Atlanta with a promising potential client. We then trade stories and laugh about our weekends — always putting our decade-long friendship first above anything business related.

“Oh, we have an interview in 3 minutes, don’t we?” he said.

We do.

For 30 minutes, we interview our next potential employee with our (all star) HR manager. After the call, us 3 jump on a separate Skype call to share our feedback, hear each other’s opinions, and ultimately reach a decision.

Then we start talking through our never-ending list of internal items:

  • Status of our upcoming company retreat — and trying to imagine how many team members we’ll be at by that time.
  • Status of ordering team t-shirts (I requested hoodies as well because why not have hoodies too?)
  • Status of new clients starting this week.
  • Status of invoices overdue.
  • Status of our internal book club, and whether or not a book was shipped to our newest employee (it was).
  • Me asking how one goes about renewing their passport, and then sharing my distaste for the dysfunctional and incredibly inefficient processes that require me (a Millennial!) to send paper documents by mail. Unbelievable.

At 12:30 p.m., the call ends. I’m starving. And while I make my way to the kitchen, I Facetime my girlfriend to see how her day is going (she also works from home). We talk for 15 minutes or so while I make lunch — today I was in rare form, trying out a new brand of microwavable gluten/dairy free frozen macaroni and cheese. It was delicious. I shall purchase again.

At 1:00 p.m., I hop on my first workshop of the day.

Workshops are our internal way of constantly improving the quality of the writing we produce here at Digital Press. It’s a method I learned studying creative writing in college. As a student, my classes consisted of nothing but sitting in a semi-circle and reading our work aloud. I found those classes to be extremely valuable for me as a writer, if for no other reason than the growth that came from hearing your own words outside of yourself, and in front of others.

Internally, I hold workshops with each of our Writer/Editor teams once per week. We pick the hardest client piece from the week before, read it aloud together over Skype, and then pick apart each section, sentence by sentence, looking for how the piece could be improved.

These workshops accomplish a multitude of things for me, as a founder:

1. They set the tone for our internal culture.

I know how writers can be. I know how editors can be. I know the egomaniacism that can happen inside publications. From Day 1, I wanted everyone to know that the dynamic is not that the writer writes and then the editor tells the writer all the things he/she did wrong. That is not conducive to growth, to morale, or to great writing. By me leading these workshops, I set that tone. We focus solely on the piece itself. We read it together. We make suggestions together. And we listen and hear each other as we work collectively to produce the best possible product. As the founder, this is my responsibility.

2. These workshops give writers and editors the feedback they need in order to improve, and continue mastering their craft.

In every interview, for every new team member, I ask them what they don’t or didn’t like about their previous job. Nearly every single person says something to the effect of, “I wasn’t getting any outside feedback. I never knew if I was improving, doing something wrong, etc.” Since Day 1 I have wanted to encourage the opposite — and not just from the feedback I provide, but creating a culture where feedback and constant improvement is expected.

3. These workshops give me time on the calendar with every single team member.

As the founder, the bigger your company scales, the more valuable your time will become. However, I am a firm believer that people are one of the best time investments you could ever make. It’s during these weekly work sessions that I’m able to get a sense for how people are doing — not just in their work, but emotionally. This gives me insight into what I can do to help them — which is good for them, and good for the team.

At 2:00 p.m., I finally have some time to dive into my own lengthy To Do list.

When I stand up from my desk chair, however, I realize that aside from making microwavable macaroni and cheese for 15 minutes, I have been sitting since 8:30 a.m.

My hips, abs, and lower back are on fire.

I decide it’s time to order a standing desk.

What I imagined should only take me 10 minutes ended up taking me close to an hour. I found a standing desk I liked online and placed the order, only to face an error message saying I had to call the company’s customer support line.

I called — and endured 15 minutes of ear-destroying waiting music, making it impossible to do anything else.

When someone did finally answer, they had to manually re-do my entire order over the phone. When I gave them my credit card, they said an order had already been placed, and I’d triggered a double-charge on their end.

“Okay, so now what?” I asked.

“Sir, you have to call your bank and tell them this was not a fraudulent charge. Then call us back with this reference number, and we can try again.”

Founderitis really kicked in then.

This is a term Drew and I have coined over the past few months. If we were to give it a formal definition, I think it would read something like this:

Founderitis (fown-der-i-tis): to effortlessly spot everything that is wrong with someone else’s company.

As founders, you spend all day, every day, improving your business. There isn’t a single minute in the day when you aren’t painfully aware of what else needs improving. And since it all falls on your shoulders, that’s a heavy burden to bear.

Which is why, should you experience a horrific customer experience with someone else’s company, Founderitis kicks in.

By 3:00 p.m. I was finally off the phone, my standing desk was in the mail, and I had 1 hour to grind through about 50 emails before my next call.

  • Emails from people who had read one of my Medium/Quora answers and were interested in becoming Digital Press clients.
  • Emails from people who had read one of my Medium/Quora answers and were wondering if I was available to consult.
  • Emails from readers just saying what’s up (I love getting these)
  • Any emails from clients
  • Emails from friends making introductions
  • Select: All deleting the insane amount of PR pitches I get in my inbox

When all is done, I grab my jacket and walk down the street to Starbucks to grab a quick afternoon coffee.

During my walk, I turn my phone on silent and try to use these 10 minutes to clear my head.

At 4:00 p.m., I jump on a Skype call with our only apprentice at Digital Press — Jack Martin. I find interns and such to be a complete waste of time, because you end up spending a disproportionate amount of time teaching as you do reaping the benefits of having 2 more hands on deck. Jack’s work ethic speaks volumes, and that alone makes the time investment worthwhile on my end. (If you are in college and you want to learn how to attract the job you want, take a page out of Jack’s playbook.)

For an hour, we do our own 1v1 workshop. We read through the piece he worked on that week together, and I provide him feedback on what’s working well in the writing, and what could be improved. Again, it’s on me to set the tone, and beyond the writing, establish how we approach the work we do here at Digital Press: never from a critical, negative place; always from a positive, improvement-focused place.

At 5:00 p.m., I make a quick snack and start preparing for my call at 5:30 p.m.

We are onboarding a new client based on China — it’s morning for him.

Same as the morning onboarding call, I kick things off, pass the conversation over to our Editor, and then put myself on mute and listen. At the 45 minute mark, I realize I’m probably going to be late for yoga — so I start to get ready a bit early while the call wraps up.

At 6:25 p.m. I’m running out the door.

On my way, I respond to text messages I’ve ignored: family group texts, friend texts, girlfriend — I text her good luck tonight. Then I turn my phone on silent and enter the yoga studio.

For that hour, nothing else matters. Not the 17 new emails that have appeared since I cleared my inbox out 3 p.m. Not the gazillion To Do items I didn’t even get to touch today. Nothing.

Ever since I herniated a disk lifting weights about a year and a half ago, I’ve really struggled to find a physical outlet. I’ve only been able to start lifting again over the past 6 months — and yoga has helped loosen up a lot of the muscles that turned into deep knots to during the herniation near my neck.

It’s hot yoga. I leave there drenched in sweat.

During my long walk home, I don’t check my phone. I know what’s there — more to respond to. But this is another one of those few pockets in my day when it’s more beneficial for me to preserve mental clarity over constantly catering to the next notification. I’ll check them when I get home. For now, I enjoy the evening walk.

Soon as I walk in the door, I turn on the TV and start making dinner. I’m not watching anything in particular — The Office, or some World of Warcraft 3v3 tournament replays, just to have something on in the background. By this point in the day, I’m braindead, and all I can focus on is making dinner.

Tonight it’s spaghetti, zucchini, and avocado — I’ve been vegan for months now.

While the pasta boils and the pan starts frying the zucchini, I bring my laptop to the kitchen counter and open a new Google document. I need to delegate one of my primary tasks to someone internally (I don’t have the time), so I start writing up a full How To guide so they can run with it on their own.

Back and forth, I bounce between explaining my modes of thinking and implementation strategies in text, and stirring my gluten free noodles.

When my dinner is finally done, I take a break from working on the document and sit down with my spaghetti. I’m starving. I watch 20 minutes of The Officewhile I wolf down an entire plate of bright red noodles. Then, it’s back to work.

By 10:17 p.m., the document is done, and I feel ready to delegate this task tomorrow. I text my girlfriend — she’s busy talking to her sister — so I start browsing Quora. This question catches my eye, because I had been thinking earlier how much my day-to-day has changed over the past few months.

I start writing this Answer. Half-way through, my girlfriend calls. We talk about our days, listening to each other, before finally saying goodnight.

I stay awake for another hour and a half to finish writing this Answer — not because I think I should write more on Quora (I always should), and not because it’s going to give me some sort of defined business goal (it might), but because I love writing. This is one of the few moments of my day when all is quiet, and I can hear myself think.

It’s 12:16 a.m.