Ask Aish: "When Does the Creative Part Actually Start?"

Where business gets spiritual...and founders get honest with their questions.

Hi Aish: I started my company because I wanted to build something meaningful! A brand with a real point of view, products I actually believed in, work that felt creative and alive. I thought I would be creating moodboards and planning creative photoshoots. But most of my days don't feel like that at all. They feel like a pile of tasks I don't know how to do, decisions I'm not qualified to make, and a to do list that never gets shorter. I keep waiting for the part where it feels creative and inspired. Am I doing it wrong? Or is everyone else just not showing this part?

AISH: You’re doing it exactly right. And truthfully no one is showing this part. Not enough, anyway. What you see on brand CEO’s feeds are the cool shoots and the press mentions and the dinners we get invited to once the thing is working. What we don’t post is the afternoon we spent on hold with the Secretary of State’s office trying to figure out whether to incorporate as an LLC or a Delaware S-corp. The morning we drove two hours to meet a manufacturer who ultimately wasn’t the right fit. The spreadsheet we built and rebuilt trying to figure out if the math even worked.

Here is what I want you to hear: that spreadsheet is creative work. The financial model is creative work. The cold call, the demand plan, the insurance broker search…all of it is creative work. It just doesn’t look the way we were told creativity looks. We were sold an image of the founder as the visionary, the taste-maker, the one with the beautiful ideas. And that person exists. But she is also the one reviewing her credit card statements and also asking whether she’s with the right bank.

The creative, meaningful work you signed up for is real. It lives inside a container that nobody fully prepares you for, and that container is operational, unglamorous, and relentless, especially in the early years. Let me show you what it actually looks like.

Pre-Launch: Just You, a Dream, and a Lot of Tabs Open

This stage is almost entirely infrastructure and blind courage. You are doing things you have never done before, often learning them the day you need to do them.

You are making cold calls to people you don’t know — suppliers, brokers, potential partners — and figuring out how to sound credible when you have nothing to show yet. You are flying or driving to meet manufacturers, walking factory floors, asking questions and hoping you’re asking the right ones. You are building a financial model from scratch, plugging in numbers, stress-testing your margins, trying to figure out if this business can actually work.

You are incorporating your business and learning what that even means. Delaware or your home state? LLC or S-corp? You are finding a trademark attorney and learning what a class filing is. You are opening a business bank account. You are applying for an EIN. You are building a website, writing your own copy, choosing your own fonts, and second-guessing all of it. You are doing customer discovery — which means asking strangers if they would buy a thing that doesn’t exist yet.

This is the creative work. The vision, yes, but also the model that tests whether the vision can survive contact with reality. Both are creative. Both require imagination and rigor in equal measure.

Launch to $1M: You Are Every Department

You have launched. Something exists. And now you are the founder, the marketer, the salesperson, the ops person, the customer service rep, and the accountant — often in the same day.

You are answering every customer email personally. You are reaching out to buyers and press with no publicist, no sales rep, just you and a well-crafted email you’ve rewritten four times. You are managing inventory in a spreadsheet because you can’t afford software yet. You are inputting invoices into Bills.com. You are running payroll for the first time and realizing how much you didn’t know about employer taxes.

You are doing demand planning based on gut and data you’re still learning to read. You are negotiating payment terms with suppliers. You are figuring out shipping rates and 3PL options and what fulfillment actually costs at scale. You are watching your cash flow obsessively — a 13-week cash flow spreadsheet that you update and stare at like it might tell you something new.

You are probably raising money or deciding not to, which means you are either pitching angel investors or figuring out a line of credit, or both. You are shopping around for business banking. You are comparing credit cards for the rewards and the limits. You are learning what goes into a term sheet, and you realize how massive the information aysmmetry is between a first time founder and an investor who negotiates these for a living. (Spoiler alert - it’s completely ridiculous and I will be writing a piece about this in the future….we are supposed to run our businesses, build brand, AND know what liquidity preferences, voting rights, and dozens of terms and details that are intentionally confusing for the founder.)

Every single one of these decisions requires creativity. The negotiation is creative. The cash flow management is creative. You are solving problems no one has solved for you, with resources that are never quite enough. That is the definition of creative work.

$1M to $10M: Building the Machine

This is the stage where you start to hire, and hiring creates its own entirely new category of work that no one warned you about.

You are choosing a payroll provider — Gusto or TriNet or Rippling — and learning that this decision has real implications. You are setting up HR systems, onboarding processes, employee handbooks. You are buying business insurance and realizing there are more kinds than you knew existed; general liability, product liability, D&O, workers’ comp. You are reviewing contracts. You are negotiating terms.

You are building processes for things that used to just happen because you did them yourself. You are documenting SOPs. You are setting up your first real tech stack — your ERP, your CRM, your inventory management system — and integrating them, or trying to. You are running weekly team meetings and realizing you have to actually prepare for them.

You are reviewing financial statements monthly, not just cash flow but a real P&L, a balance sheet. You are navigating your first 409A valuation, in case you did raise money from angels. You are constantly asking: do we have the right partners? The right 3PL? The right bank? The right insurance broker? Because at this stage the infrastructure matters enormously and switching costs are real.

You are also managing people now, which is its own form of creative and emotional labor — one that will ask more of you than almost anything else.

$10M+: Still in the Trenches

Here is where I want to push back on a story you may have heard: that once you reach a certain size, you ascend to some elevated plane of pure strategy and vision, finally free from the details.

That is not what the best founders I know are doing.

At $10M and beyond, you are still reviewing your Ramp charges line by line. You are still asking whether you’re with the right bank, the right credit card, the right insurance broker. You are building OKRs and holding your team accountable to them with honesty and rigor. You are running business reviews. You are looking at channel mix and asking hard questions about where growth is actually coming from. You are reviewing budgets, forecasting, making decisions about org structure and resource allocation. You’re trying to decide between bullshit and real stuff when a senior hire shares their POV on something with you. You’re figuring out which law firm to hire when you get hit with your third ADA lawsuit (good luck trying to escape out of this one — if you have a reasonably sized biz, they’re coming from you at least every 24 months). You’re making the hard call to let team members go. You are still, constantly, building.

The work doesn’t become less detailed as you grow. If anything, the details become more consequential. The best CEOs I know still have an extraordinarily tight pulse on their businesses..and these are founders whose companies are doing $100M and beyond. They know their numbers. They know their unit economics. They know who handles their sales tax and why. And let me be clear here —that is not a failure of delegation. That is mastery.

A Note on Creativity and the CEO Role

I want to say something directly to the person who got into this because they love the creative work — the brand, the product, the vision — and finds the operational reality of building a company exhausting or misaligned with who they are.

Because here is the truth: what I’ve described above is the job of the CEO. Not a distraction from the job. Not the unglamorous tax you pay to get to the real work. This is the real work. The CEO is the person who holds the financial model and the brand vision at the same time, who cares as much about contribution margin as she does about the creative direction, who knows that a beautiful product sitting in the wrong 3PL with broken demand planning will not reach the people it was made for.

If you are someone who genuinely only wants to do the creative work — and that is a completely legitimate thing to want — then the move is not to push through and become a reluctant operator. The move is to find a partner or hire a CEO who loves this stuff, and to let yourself be the Chief Creative Officer of the thing you’re building. That is a real and valuable role. Just go in clear-eyed about what you’re choosing.

But if you want to be the CEO, then the spreadsheet is yours. The insurance broker is yours. The 13-week cash flow is yours. And with time, if you let it, all of it becomes something you’re proud of, because it is the architecture underneath everything beautiful you’ve built.

The Most Memorable Business Conversation I’ve Ever Had

A few years ago, I had the privilege of spending an hour on the phone with Indra Nooyi, the former CEO of PepsiCo. This came through an incredibly generous introduction: one of our investors had been her mentor, the former president of the Boston Consulting Group, and he kindly connected us.

What I got was one of the most clarifying business conversations of my life.

She zoomed into Brightland with a precision that stunned me. She asked detailed, specific, probing questions about my business…the kind of questions that showed that nothing was too small for her attention. This was a woman who had overseen a Fortune 50 company. Hundreds of thousands of employees. Billions in revenue. And she was sitting with me, a founder of a small premium olive oil brand, asking the kind of questions that only someone who truly understands the details of business would know to ask.

That conversation changed something in me. Because if Indra Nooyi is still that close to the details — still that curious, still that rigorous — then there is no stage at which any of us gets to stop paying attention.

There is no version of this job where the details stop mattering. There is only the version where you get better at holding them, where you build a team that helps you carry them, and where you slowly, over time, start to understand that knowing your business this deeply is not the obstacle to doing creative work.

It is the most creative thing you will ever do.

Photo by omid armin on Unsplash