Entrepreneurs Share About Growing From 1 to 10 Employees

by | Feb 5, 2021 | Blog

Daniel Koffler

Daniel Koffler

President of New Frontiers

When you first start a business, you are basically doing everything—from the things that you may be good at which may have given you the confidence to start run with the idea in the first place, to the seemingly limitless list of things that you had no idea needed to be handled (and without proper handling, can very quickly sink the ship).

As you grow from 1 to 10 employees, you need to ensure a few critical things are in place.

First, thoughtful and firmly established core values.

These will end up dictating every from who/how you hire, to when you go to market with a particular product, to what that product is!

I can’t stress enough how important it is to define these, and communicate them directly and indirectly to anyone interested in participating on this journey with you.

Next, you need to be clear about who is accountable to whom.

This has the potential to become a major sticking point as you scale—remember, not long ago it was just one person doing everything.

How you delegate to the new team members and hold them accountable to those tasks will establish the foundation (from at least a tactical POV) for things getting done.

Best practice suggests creating an accountability chart (not the same as an org chat, but similar).

This document can (and should) evolve and grow with the company.

The closer you get to establishing this with the 1st hire (2nd employee), the smoother things will be.

There are obviously more things that one can—and should—do to ensure sustainable growth within an organization that is ramping up.

If you get these two things right, though, you are definitely more than halfway there!

New Frontiers Executive Functioning Coaching

Janet Semenova

Janet Semenova

Co-Founder of Boutique Travel Advisors and Centered CEOs

Most small business owners begin their ventures as either solopreneurs or with just one or two employees.

However, any company that wants to grow, scale, and become a sustainably profitable business must expand its team, outsource responsibilities, and learn to delegate.

Small business owners who take the time to create processes and implement systems can add team members in a streamlined and organized fashion.

Business owners who function in a silo and do not write down or record their procedures will struggle to bring in new talent.

Communicating why you do what you do is just as important as how you do it.

Many small business owners are reticent and unprepared to delegate responsibilities.

They falsely believe that “no one else will be able to do it as well” as they can or are fearful of investing the necessary capital to scale their team.

This often creates inefficiencies and leads to lost revenue.

To achieve lasting success, a business must grow and adapt.

It is essential to shift your mindset and understand that delegation is a sign of leadership and fortitude.

As you add team members, it is vital to focus on creating an environment conducive to collaboration, innovation, and creativity.

When employees feel wanted, supported, and heard, they become personally invested in seeing the company they work for succeeding.

By providing mentorship to your employees and allowing them to learn from their mistakes, business owners can foster meaningful long-term working relationships.

It is natural to feel fear and want to resist giving up control over areas of your business.

However, by delegating tasks that are not driving revenue or are outside your area of expertise, you can re-focus your energy on elevating your brand, products, and services.

This is how your business can create an undisputed market-dominating position and successfully scale.

Dave Shanley

Dave Shanley

CEO of Content Camel

Growing from the original founder or founding team to ten people is all about the growth from “just an idea” to “whoa, we have a real company”.

If you’ve earned it — from revenue — then it’s about finding product market fit, and if you’ve bought it — from funding — it’s all about hustling to get the team focused on hitting your next milestones.

Regardless, as you starting to grow beyond a two pizza team, you start thinking about the systems you need to put in place to achieve the next growth milestone.

It’s a shift from simple drive-by conversations and late night Slack messages to repeatable processes and a shared understanding that can scale.
Content Camel

Eropa Stein

Eropa Stein

CEO of Hyre

Nearly every entrepreneur started off taking on every role in the company.

When I grew from being on my own to 10 employees, I had to learn to trust others to do their roles the way that was best for my start-up.

I was so used to dipping my toes into every part of my business, it took some getting used to in order to let others take charge.

As an entrepreneur, I am naturally resourceful and constantly connecting with other founders to share insights.

I share what I learned with my team and want them to pursue goals as relentlessly as I do.

I want to be in touch with every aspect of operations, but I only have so many hours in a day.

Learning to trust and let go has been vital to my journey.


Xavier Parkhouse-Parker

Xavier Parkhouse-Parker

COO of Cambridge Future Tech

The biggest change is always communication and it’s the mindset that fundamentally has to change, or the company is dead.

Three friends sitting in a room working on a project do not need the think about how to communicate, it flows naturally and constantly.

A ten-person company is where the need for structured informational flow is necessary.
There are two main reasons.

There is too much information.

At ten people the information and data start to be vast and not everyone needs (or wants) to know everything.

At three people, it makes sense for everyone to know everything (and be CC’d into all communications).

At 10 this would kill productivity.

Naturally, though this does not happen and people tend to silo information – the right people do not get the right information.

This also kills the business, in an early-stage startup, you can not have people waiting around for information or making decisions based on incomplete or inaccurate information.

This problem tends to stem from the CEO since the CEO will typically have a clear view of the whole organisation and therefore is responsible for ensuring that information flows to each the right people at the right point.

Their mindset needs to be that ‘without incredible communication we will not make it’.

Cambridge Future Tech

Michael Podolsky

Michael Podolsky

CEO & Co-Founder of Pissed Consumer

I’ve been an entrepreneur for 15 years.

As a CEO and co-founder of PissedConsumer.com, a review platform and consumer advocacy website, I’ve faced challenges that impacted my mindset and the company.

We went from 2 to 100 people.

Looking back, I realize that such a variety of challenges has shaped my habits and attitude in business.

As we grew and realized that we need to hire, it became challenging to find talents.

It was important to us to pass our culture to employees in the organization.

I knew that the military-like style that works for UPS, would certainly not work at my company – high-tech software development.
So, we built a tree structure of management.

We see it as 1-7-49-100.

Let me explain it roughly.

One person can coordinate up to 7 people efficiently.

As you grow, these 7 employees will manage 7 new members, which extends to 49 member in total, and then it goes up to 100.

With each level, the distance between top tier and low-level employees extends.

I value transparency and idea flow within the company.

As an entrepreneur, you have to make sure that senior managers teach the management basics to middle-level managers and help educate junior employees in the organization.
I had to think about how to build a more cohesive team that shares values and corporate culture, and not to lose that connection within the company as it expands naturally.

Pissed Consumer

Brandon Cockrell

Brandon Cockrell

President of Linchpin Sales

Each time you hire another team member your role changes, and with these changes comes a drastic mindset shift (which can be very uncomfortable).

This causes you to change everything from your daily habits, to how you measure your success, what goals you have each day, and even what groups you network with.

For example, at first, I was the sales department which quickly developed into the execution team, followed by the customer service department, then accounting, and so on.

Now, my role is mainly around finding great talent, developing strong internal processes, and making decisions on how to best keep our brand moving forward as a leader in the industry.

Each one of these roles require a different thought process and mindset shift in order to make them successful.

So, make sure to get comfortable feeling uncomfortable, trust your instincts, and invest in mentorship when needed!

Linchpin Sales

About the Community

On the podcast, Sean talks with entrepreneurs about the reality of their struggle to succeed, as well as answering questions from the community, and sharing nuggets of wisdom from his own life.

Discover through these amazing episodes the courage to open your mind, heart, and soul to the world so you can be the best entrepreneur possible, respect the people you work with, and improve the world with your company while not hurting others or yourself in the process.

Sean Weisbrot

Sean Weisbrot

Sean is an entrepreneur, investor, and advisor based in SE Asia for over 12 years. He is passionate about Psychology and helping others improve themselves.

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