Holding the space

(Today, we’re starting with a bit of a detour. I promise we’re still going to talk about commerce eventually. I just need to set the scene before getting there.)

In my freelancing days, the best Engagement Manager I’ve ever worked with was called Dave.

Chronically unkempt hair, colorful bandanas, and the tiniest backpack humanity has ever designed always over his right shoulder, Dave was the kind of guy you wanted in your corner on a messy engagement. Together, we’ve worked on what remains the most incredible project turnaround of my career, which eventually led to me being poached by our client as their CTO.

Despite having the authority to do so, Dave didn’t micromanage, didn’t push for deadlines, and didn’t point fingers—no matter how stressful things got.

Instead, Dave always had our backs. He did this in very conventional ways—by supporting us during difficult client conversations, advocating for our team to get the best designers and developers, and making sure projects were well-scoped—but also in very unconventional ways.

Dave will remain known for things such as:

• Buying lifetime Calm subscriptions for everyone on his team and asking them to meditate daily in the weeks leading up to a stressful launch.
• Making sure everyone stayed hydrated and didn’t get too drunk during a client party at now-defunct Electric Pickle.
• Allowing me to take a much-needed shower and have breakfast at his place in Hollywood, FL at 5am before a big demo.

I was not surprised when Dave went on to do amazing things. He was good, and cool, and completely crazy, and we all loved him.

Most importantly, Dave had an unwavering ability to hold the space. By that, I mean he could systematically identify and create the conditions for people to be their best selves, which in turn allowed them to do their best work. It felt good. It felt empowering. And it led people to accomplish the impossible.

And this is where Dave’s story and the story of commerce converge.

In 2021, $5B of VC money flowed into DTC. In 2023, that figure fell to $130M—a 97% decrease. When oxygen is sucked out of a room in such dramatic fashion, those left standing experience increased pressure to deliver results, and to do so more quickly and with fewer resources than they were ever prepared for.

As external pressure increases, a company’s ability to hold the space decreases. At a strategic level, that means there’s less room for intentional decision-making, investments with a longer time horizon, or experiments that eschew existing best practices. At a tactical level, it often means increased expectations, longer hours, and shorter tempers.

Service and technology vendors understand this dance very well, and they all line up to reposition themselves as the partner that unlocks quick impact and unparalleled efficiency. A shrinking market consolidates power in the hands of a select few. A shrinking market also generates rigid blueprints: you either play by our rules or don’t play at all.

However, blueprints are always the lowest common denominator of an industry. They’re not recipes for innovation—which, by definition, do not exist—and they often gloss over the complexities of the real world—which, it turns out, cannot simply be willed out of existence.

I recently wrote a LinkedIn post about failed Shopify replatforms that exemplifies this concept well. Right now, it is common knowledge in e-commerce that Shopify is THE platform to be on. At a time when everyone is trying to do more with less, Shopify’s promise is that it allows brands to cut costs while also offering the best partner ecosystem and highest-performing shopping experience in the industry. What’s not to love?

Unfortunately, while the underlying proposition is solid, many brands shoot themselves in their big corporate foot by attempting to artificially accelerate adoption. Their burning desire for something better leads to a quasi-religious suspension of disbelief, which manifests in unrealistic expectations, hasty planning, and subpar execution.

In the short term, this trend hurts the brands that see their replatforms turn from beautiful fairytales into unspeakable nightmares. In the long term, it may also hurt Shopify: once we realize that there’s no such thing as a free lunch, I wouldn’t be surprised if we started looking for the next witch to burn.

I appreciate that this might all sound a bit reactionary, so let me be clear: Shopify is an amazing piece of technology, and we’re proud and happy partners. In fact, we’re involved in at least three large-scale Shopify replatforms at the moment that we think will have a dramatically positive impact on the brands that commissioned them.

But like all technology, Shopify is not magical. It has strengths and weaknesses, it affords freedoms and creates limitations, it simplifies certain aspects and complicates others. If most small brands can afford to ignore the downsides, that’s not the case for larger merchants. The more you have to lose, the more you need to hold the space—not just when it comes to technology, but across all areas of the business.

As for what “holding the space” looks like in practice, I’ll be honest: it’s easier said than done. It’s highly dependent on your financial posture, corporate governance, and board composition. There’s only so much you can do to hold the space when doing a certain thing by a certain date will determine whether you get your next round of funding.

With that said, there is some space-holding advice that I think can be applied even under intense stress and scrutiny:

• Beware of blanket recommendations. When someone says you HAVE to do X, you should be skeptical by default. Why is X important for you? What are the upsides? What are the downsides? (Corollary: Don’t do something just because it has worked for you at previous companies or in previous situations.)
• Don’t be afraid to sound stupid. Sometimes, executives don’t want to question basic assumptions for fear of sounding incompetent, ignorant, or out of touch with the zeitgeist. As it turns out, “the zeigeist” is often the collective artifact of a bunch of people with your exact same fears and aspirations.
• Hire good leaders. Good leaders act as buffers: when pressure is high, they hold the space just long enough for the company to still make the right decision. (Lately, I’ve started to think this is also what makes good agencies so valuable: by being removed from the daily grind, they have the luxury of pushing back on bad choices.)

To some, this might all sound very touchy-feely and disconnected from the harsh reality of doing business. However, I’ve been at this for some time now and I’ve seen tens of companies go through their journey—some were wildly successful, others not as much.

The ones that made it had one thing in common: during stressful times, they did everything they could to continue to hold the space, stay intentional, and allow people to bring their best selves to work.

And if nothing else, it might help to know that I still use Dave’s Calm subscription every day.