Lessons From Running A Business Rather Than Just Thinking About Business

Welcome to our first Substack newsletter. Buckle up.

Over on Mailchimp, we send out a weekly newsletter to 11,000 people. But we've sat on the Substack fence for a while. Today, we get butt off said fence and dive in.

Waking up this morning to tens of new subscribers was motivation enough.

Many of your names I recognize. Some of you have had great success in the past few years running and selling agencies. Even if we haven't spoken in a while, I watch on and love seeing your success.

A little introduction

If you don't know me, in short: Hi, I'm Mark Pollard (@markpollard).

I've worked in agencies since I was about 19. For the first ten years I worked in digital agencies and digital departments as a producer but back when that involved writing long functional specifications, doing the information architecture and wire frames for projects.

At 28, I moved to Leo Burnett Sydney and worked in a hybrid role–50% digital planner, 50% account planner. A few years later, I moved to New York to "do good work at scale". I struggled. The corporate culture shock drained me–too much bureaucracy, too many meetings, so hard to do good work, and all of it felt conservative compared to what I was used to.

But, during my first five years here, I taught strategy and spoke at conferences a few times a year. Each time I did, I felt reinvigorated. So, five years ago, I decided to leave the corporate world and rebuild my life. Sweathead is part of it.

On January 20, 2018, Sweathead launched as a Facebook Group. A month later, I launched the podcast. In 2020, when the world shut down, all of my plans were scuttled. My first book "Strategy Is Your Words" had just been funded on Kickstarter so I navigated lockdowns, factory closures, and shipping complexity to get it printed and launched and, in the meantime, I turned it into 100 classes. And this got us through the year.

Now, as our fifth anniversary approaches, Sweathead has a team of about eight freelancers making it happen. We're running conferences such as The Sweathead Do-Together, multi-week training programs such as The Sweathead Strategy Accelerator, and, in 2023, we'll have three levels of memberships, two of which will include masterclasses and more.

Part of what we're trying to work out is how to bring in more strategists and pay them equitably. In 2021, we paid our Do-Together speakers 2% of gross revenue. We haven't cracked the model yet but we think about it every week. By the end of 2022, we'll have paid over 40 strategists to teach with us. You can find out about it all on the Sweathead website.

My first Substack was going to be called, "The Most Ugly And The Most Beautiful Truths About The Strategy Life". But I'm going to save that for next time and, instead, give you a list of things I've learned, struggled with, or enjoyed about running a strategy business in New York.

Here you go:

1. You have no choice but to launch

I love the melee of the strategy life–wrestling with confusion, lingering in a possible connection between things you've found in odd places, mind-mapping on tens of pieces of paper to arrive at one sentence. Sometimes, you emerge from the melee with clarity in hand like a soldier with a King's crown.

But running a business is simpler in many ways. If you think for too long or if you think to exhaustion, nothing happens. If you have no product to sell then there's nothing to buy. If there's nothing to buy then you don't have a business.

"What are we doing next?" is a critical question. Yes, there can be delays and do-overs, but you have to launch. And while each launch is stressful, you know that if you keep going for years to come, you'll have launched tens of things and some of them will be successful.

2. Make a deal, make it happen, then learn from it

One thing that irks people new to freelancing or setting up their own business is money–what to charge, how to ask for it, and how to follow up about it.

If you do only one or two deals a year then each will seem precious. What if you get yourself into a bad situation and get taken advantage of? What if a better opportunity comes up? What if you could save a few cents here and there?

Building a business is about building velocity. You need to be able to get up to a certain speed so that there is enough momentum to carry you into the next thing. The opposite of this is feeling like you're starting over again every time you do something, like you raise a flag up a skyscraper-tall flagpole in the morning then lower it in the evening and repeat the whole affair the next day. Exhausting.

I believe it's useful to approach deals with some light-heartedness, as if you're playing a game. Work out what you think you're worth, work out what's non-negotiable, ask for you want, and hope the deal comes in. Then do the work and, later, spend time thinking through how you'd approach it differently next time.

You'll make mistakes. You'll lose money on some deals. You'll waste time on some deals. You'll throw bonuses into your deals as an act of goodwill that might not have been worth it. It's all good. Each deal is an opportunity to learn.

3. It can take time to redefine what "real work" is

I still struggle with this: sometimes, I'll spend a day paying invoices or hours trying to fix something on the website, and the advertising strategist inside of me says, "This isn't real work."

The truth is, some of this is the most important work at the time. For example, I respond to most of our customer service emails. We're at a point where I could bring someone in to do this (and we will soon), but it's important work to me so I do it.

I remember spending a day paying invoices for our first conference in 2021. I felt guilty because I wasn't writing or generating new ideas but I also felt really fulfilled. Sure, we weren't paying our speakers millions of dollars but we'd set out to try to pay them 2% of gross revenue and, while the event just broke even, that day of paying invoices ended up filling me with smiles.

4. The rhythm of business is different from the rhythm of the strategist

When I set out on my own six years ago, I wrote a list of what I wanted to strive for. A big part of what I wanted to do was to create things ("IP" if you like) that I could sell in many different ways. Another was to wean myself off two decades of timesheets.

What this can look like is bursts of intense creation, such as months of writing and editing a book or long days making videos for online classes, but, eventually, you emerge with a catalog of work that goes to work for you even when you're not in front of a computer.

I'm 44 now. And I still get anxious on weekends when I choose not to work. So much of my twenties involved working weekends for agencies or publishing a hip hop magazine. I'm still wrestling with this because, when I am anxious, sometimes sitting down and drawing up a plan for the week or thinking through an event to launch, calms me down. But is that a good thing?

I've borrowed phrases such as "I am where I need to be" and "I don't have to, I get to" that help me talk back to that voice in my head that says, "You should be working now." But the rhythms of running a business are different from the firehose of the strategy life.

5. You need to think in catalogs

Part of me wishes I studied art or writing when I was younger. I might have understood the artist's mindset better. But, as with many of us, I was told that poverty is not success and that artists are poor.

The thing about artists is this: they have to make. They often publish in catalogs or collections or ranges. These are useful concepts for people starting their own businesses. It means you don't stop at the first thing.

It means you don't try to narrow down just that one thing. It means you create and launch a catalog of things and then another. And I think this mentality is very good for mental health. Launch and release then repeat.

Next steps

Thank you for being here. I hope you check out what the team and I launch in 2023 with Sweathead. Whatever happens with the economy, I know one thing: we gotta launch.

Got a request?

Feel free to send me a question or a prompt. I'll name-drop you in my response :)

--Mark, Strategy Friend

-> @markpollard