Unlocking Growth: 3 Holistic Approaches to Scaling Your Business

In 2021, my friend Matt Shterenberg brought me on to manage a couple of his accounts at his seedling cannabis SEO agency.

It was a fractional role that quickly turned into something much bigger.

We started with 7 clients totaling $60k in monthly recurring revenue.

At that point, the business was a blank slate.

We had two incredibly talented founders, a developer and a part-time VA but systems needed to be built. And an entire customer experience funnel. And a way to talk about and market the service. And a consistency to scopes that would allow us to scale.

Over the next three years, we built it ALL and reached $260k MRR with a lean team of specialists that functioned together as a united team. But it came with plenty of challenges.

I learned business best practices of operations and strategy alone would not grow our remote team. It required a type of thinking and way of management that would hold people accountable, and still have the leniency to make shifts and changes with the ever-changing industry to which it demands.

In some ways, I took from the Daoists in that “nature does not hurry, yet everything is accomplished.”

I consider this a holistic mentality, and it was critical to scaling a burgeoning digital business.

1. ‘Perfect’ data is your enemy

Whether it’s understanding your LTV, cost of fulfillment or sales funnel, in a fast-growing startup, tracking and comparing data year over year and even month over month will almost never match exactly.

Comparing apples to oranges is the name of the game, and mentally, if you don’t allow yourself the space to see things from a spectrum, you will find yourself confused and overwhelmed.

It’s easy to get bogged down with the constant fluctuation of scopes/offerings as you continue to narrow down the process and the best way to package your ever-growing product or service.

In my experience, the ability to be flexible and take an 80/20 approach to collecting data allowed me to make decisions and move fast enough to manage the pace of a growing sales funnel.
Another favorite Daoist quote:

“Those who have knowledge, don’t predict. Those who predict, don’t have knowledge.”

For example, time tracking the team was necessary, but I needed to ask “is it necessary indefinitely?” I applied required time tracking for 20% of the month (~10 business days) to understand where time was going. I knew recording hours for specific tasks was a lot to ask of a team with a full stack of work. From there, I projected the rest of their time and made due.

Of course, the name of the game here is something is better than nothing. Sometimes the act of developing how to turn things into data gave us answers to things we didn’t have before. For example, in the process of find the best way to track lifetime value, we realized that what we considered a one off foundational project should actually just be turned into ongoing work from the beginning, shortening our sales cycle and streamlining the onboarding for the team. Of course, this changed everything about how to track lifetime value, but it made a difference to our bottom line.

Ultimately, striving for perfect data leads you nowhere. Living in the gray is where decisions need to be made.

2. Authenticity is the ONLY path to functional culture

Building a set of boilerplate values will lead to a confused team without a clear direction when you are tasked with finding a next course of action that is not cut and dry. When you’re building a team, especially in a remote workplace, using terms like Integrity, Collaboration, Resiliency are just too vague and uninspiring. Humans will be human and glaze over them, forgetting any kind of power they have over their day to day work. It’s not tied to an authentic story.

Finding the authentic story requires the personality and ethical pursuits of its founders and leadership.

Deeproots partners niches in cannabis. Everyday we work wtih dispensary owners and cannabis brands. Weed is the future and it’s something that most of our team consumes. So naturally, Matt and I consumed one night and got to talking. After an imbibing in some indica, the words rank and spank came up. Was it professional? Not exactly. Could it be considered slightly risque? Sure. But those traits are almost synonymous with our industry, and we knew that it had the right zing to hold the attention of our team and our partners.

“Rank and Spank” was born and it promoted our culture of drive, competitiveness and humor.

Functional culture, or a culture that actually works for the people living in it day to day, requires time, analysis and a point of view. It also requires daily reinforcement.

A culture doc will get lost in the folders of your database. People will not keep it up on their desktop and meditate on them every day. That’s where utilizing team meetings to regularly talk about examples where the value popped up in the work allows us to collectively further define the culture: democratizing the vibe and allowing everyone to feel connected to them.

Additionally, if you are not authentically walking the walk as a leadership team, the values have nowhere to flourish. For example, if “Stay curious” is part of your values, how do you help your team live up to that? In my own case, the founders invested in ongoing learning from a high level operations course which I accepted with excitement. It allowed me to lean in every day to our value of “Be the Very Best” which the rest of the team saw in the work and my attitude.

3. Pragmatism wins over distraction any day

Entrepreneurs are faced with shiny objects every day. Partnerships and deals that might, on its surface, be aligned with a future vision but upon further investigation would end up taking time away from core goals.

Time is the most valuable resource of a leadership team. Most of the time, we are at a point in our careers where working 14 hour days is not in the cards. We’ve put in the work. We’ve become the specialists and been in the fulfillment roles, so why would we punish ourselves in reaching these heights without setting up our days for optimal happiness.

So, the name of the pragmatic game is making the most of those 6 good hours in a day to really move things forward.

It requires planning and focus. It requires dedication to realizing that not every idea is a good one. And to be honest with yourself about the

It requires the leadership team to create space to communicate ideas without. Realistically, can we get this project done in three months or will it actually take six? Will we need a new version of this by then anyway considering our growth.

The pragmatic conversation is the one that shouldn’t leave everyone feeling disappointed. It should be cause for celebration and success. We lived another day without leaning from our path.

What power and success could we find if we start to humanize our work? If we start to find more commonalities with philosophy vs “10 ways to jumpstart your business using AI”.

I challenge us all to consider where we would be without the chains of our past learnings. And be OK to predict that nothing can be predicted.