Why Great Leaders Are Perpetual Students

Hi everyone, 

It’s time for another bite to chew on. 

We spend a lot of energy sharing our strategies and tactics here. But today we want to pull back a bit and talk about something more fundamental → 

Mindset. 

If you’re a dedicated founder, you probably have the drive to get better and better all the time. 

You want to develop mastery. You want yourself, your brand, and your company to be the best. 

That kind of ambition is a vital piece of the puzzle. But it’s not the whole thing. 

Over the years we’ve discovered something else - that your mindset must also include a blend of humility and curiosity.   

Because you’ll never, ever be great at everything. 

Because there’s always another layer of wisdom and knowledge to be discovered when it comes to your company, or your industry, or the world in general…

You have to be dedicated to becoming a perpetual student.

That way, you are always prepared to learn from others, from your business, and (especially) from your own mistakes. 

Today we’re going to go through what that has meant for us and how you can think about becoming a great student - 

Rather than only focusing on being a master. 

On the Menu

• First Course - Become a student of your business

• Second Course - Become a student of your market

• Third Course - Become a student of your channel

How to become a student of your business 🎓

This is natural when you are just starting out and looking for product market fit. 

You are nothing but a student at this point because you don’t know anything, besides your conviction that you can make this idea work somehow. 

But as you get traction and add team members, sales channels, and marketing strategies…

There is the temptation to get a bit lost in the day-to-day of everything. 

If you are running around and trying to: 

• Fight fires

• Develop relationships

• Build teams

• Attend meetings

• Manage admin

• Create new products

It can be easy to get caught up in the never-ending hamster wheel of to do lists and “action items”. 

A cluttered calendar is a preoccupied mind. 

Here’s a framework to think about things as you study your business and your role as a leader:

GREAT: What is the one big thing that, if accomplished, would have the biggest impact on my business?

GUT PUNCH: Why are ideal prospects not buying from us?

INTENSITY: In what areas of life can I double my intensity?

PROCRASTINATION: What are three things I haven’t started because I’m pursuing perfection and what is one small step I can take today?

ENEMY QUESTION: If I was competing against myself what chinks in the armor would I exploit?

It can feel like you don’t have the time or energy to take a step back and look at your business. 

Except once you are growing and scaling, a leader's job begins to shift from the core of operations to the guiding hand on the wheel. 

And in that case, it’s very important for you to understand where you’re going and how you’re going to get there. 

Because if you don’t understand this on a fundamental level, neither will the rest of the company. 

This will ultimately cause chaos, confusion, and cap your growth (or doom or your business entirely). 

What does this mean in practice? It varies from brand to brand, person to person, but here’s what we’ve had to always learn about when it comes to Obvi:

Finances 💵

You need to constantly update your understanding of the relationship between your income, your costs, and your investments. 

Topline growth can become an obsession but also a distraction, because it may not have much relationship to your bottom line. 

Especially if you aren’t going in and regularly updating your knowledge of what you're making and what you’re spending. 

Growth Levers 🎚️

When you first start out, you’ll probably have one hero product, one sales channel, and one marketing channel. 

But opportunities and distractions will multiply quickly once you reach 7-figures and beyond. 

There is always a new tactic, a new tool, another sales channel, a different market to pursue. 

Your focus can become scattered across so many different things, that it becomes necessary to pull back and deep dive into your core vision, mission, and competencies. 

You need to regularly evaluate what is driving you forward, versus what is just a drag on your efforts.

Biggest risks and landmines 💣

Once you are out of PMF survival mode, it’s not just the operations and opportunities that multiply, but also the risks you’ll face.

• How solid and dependable is your supply chain?

• How healthy is your brand perception?

• Does your cash flow and fundraising match your growth ambitions?

Some brands are killed by outside factors, but most die because they don’t spot the pitfalls and landmines along their path before it’s too late. 

Team alignment 👨‍👩‍👧‍👦

Perhaps the biggest learning curve for entrepreneurs is how to go from a founder to a CEO. 

Everything in the early days is intuitive because it all flows through you. That changes as you grow because it becomes impossible to do everything.

So you need to build a team. 

But even if you try your best to “hire for culture”, share your unique brand vision, and carefully onboard new teammates when they arrive…

There will always be the need to study and re-evaluate your team’s understanding and alignment within the business. 

• New hires will never care as much as you do

• They will only see a fraction of the company or the brand on a daily basis

• They may not understand why certain decisions are being made

• Their incentives may not match what you’re trying to achieve as a leader

If you aren’t regularly assessing how your team thinks about the business, its goal, their role within it, and what's in it for them - 

Then you face being undermined by inefficiency and conflict.

What you can do

Try this exercise.

Draw 4 quadrants on a whiteboard. 

Add each of these headings:

• Differentiator/Critical ← Core efforts, leadership, and investments

• Non-Differentiator/Critical ← Staff, VAs, offshoring, vendors

• Differentiator/Non-Critical ← Roadmap for future special projects / big swings

• Non-Differentiator/Non-Critical ← Get rid off

Now go ahead and fill in your company’s roles, projects, and operations in each quadrant. 

This should help clarify what you are doing now vs what you should actually be spending your time and resources on. 

Now, this is just an example of a simple process that will help you study your own business on an ongoing basis.  

But the real lesson is to take the time to step outside of the day-to-day and carefully go over what you’re doing, what is working, what your challenges are, and what needs to be done.

Tool of the Week

Before we talk about becoming a student of your market…

We want to share something we recently discovered when it comes to checkout optimization.

Like many DTC brands, we’ve tested a bunch of stuff in checkout.

The 2 biggest things we’ve found so far:

⭐️ Product reviews

📆 An exact delivery date

These are easy to implement with Aftersell, but they’ve made a major impact for us so far.

Want to learn more tactics like this?

Join me (Ron) and Alicia Gan of Aftersell on September 18 where I will share Obvi’s strategies for optimizing your checkout experience.

Sign up for free to learn:

🔥 How to lower complexity and abandonment in your checkout.

🔥 How to use free shipping and other offers to boost conversion rate.

🔥 How UGC, testimonials, and trust badges can increase credibility.

And way more.

If you’re looking for ways to optimize your Shopify checkout in advance of BFCM, you don’t want to miss this one.

Become a student of your market 🧑🏽‍🎓

Of course, you can’t just navel gaze your way to success. 

If your company is a ship, then your market is the sea. 

You need to study your target demographic, what they want, what they don’t want, and how to position yourself. 

When you first get going, it’s easy to interact with customers. 

You probably spent time reacting to Facebook comments or responding to emails. 

Eventually, there’ll be too many comments, too many requests for you to manage. You’ll lose that direct contact. 

Instead, you have to purposefully build processes and feedback loops so your customer's voice is always heard.

Not just by your customer service team, but by leadership as well.

Even more important is having a thick skin and the humility to accept criticism. 

Everyone loves to read their 5-star reviews. But it’s the 1-stars that can be the most educational. 

You can’t please everyone and there will always be haters, but you need to separate the random negativity from the stuff that tells you something useful about your biz. 

• Is there a problem with product quality or quality assurance?

• Is there friction in your buying process or customer service?

• Does your key value prop or brand position resonate?

• Are people asking for something new? 

Always find a way to keep an ear to the ground. 

Study how well you’re serving your customers, if you are building a relationship and loyalty, and if you’re making it easier or harder to buy from you. 

But also, you need to keep a constant eye on the horizon so you can spot any big opportunities or challenges before they crash down on you. 

• Is there a fad or trend you can take advantage of to boost growth?

• Is something disrupting your market that may benefit or threaten you?

• Who are your key competitors? 

• What tactics or strategies are they using to gain market share?

Things like this will always shift, change, and evolve. 

Your understanding of the market cannot be taken for granted, be it your customers or the competitive landscape. 

Become a student of your channel 👩🏼‍🎓

Okay, this is getting a bit long so we’ll make this section brief. 

Aside from your business and your market, you’ll also need to study your channel. 

A DTC company that sells on Amazon vs a CPG company that distributes through major retail are very different beasts. 

Each will have its own unique hurdles, costs, strengths, and metrics.  

Without studying and understanding your sales channel(s), you will have a hard time making sense of your own performance and efforts. 

Think about…

• What are the established norms in your channel?

• How do you contextualize your metrics against other sellers and brands?

• How are similar companies driving growth and profit? 

We’re not saying you should research DTC as an industry and then try to mirror all of the benchmarks and best practices you find.

No two brands or businesses are exactly the same. 

But sometimes putting your performance in context can at least give you a clue about how to understand what you’re doing well. 

Or it can raise a red flag when you find a key measure that is lagging behind your peers. 

Sum it up ✍️

You can’t rest on your laurels in DTC and consumer. 

And you can’t only commit yourself to the study of your business, your market, or your sales channels. 

You have to always be learning about all three.

But let’s return to the issue of mindset. 

We hope the frameworks and advice we’ve shared here are useful, but the big takeaway is - 

Be both bold and curious. 

Ambitious and humble.   

In this game, there’s always another level to unlock. 

Another boss fight to conquer.  

You have to develop the kind of ego that says “I can do this impossible thing”.

But also have the perspective of a student who is hungry to learn more and who has humility before the facts. 

All the best,

Ron and Ash