How To Shift From Startup Founder to CEO: Lessons in Scaling from Airbnb CEO Brian Chesky

Building a new company can be a daunting endeavor. It will probably be the most challenging mission on which you will ever embark as a startup founder. There are pitfalls along the way and obstacles to overcome. Most entrepreneurs thrive on the challenge, but what about once the startup phase is over? How do you leverage the skills you have learned as a founder and transition effectively into the role of CEO?

In a recent interview from Stanford University, Airbnb CEO Brian Chesky shared how Airbnb came to be and some of the challenges they have faced and the lessons they have learned along the way as they have scaled the business.

It’s very rare to be the person who starts a company and be the person who scales it to 1,000 people. You have to be a very different person at each stage.

- Brian Chesky, Airbnb

As an entrepreneur, it is "all hands on deck."  Everyone does everything and business growth during this phase is all about survival. My colleague, Carol Bodge, calls this the "funding to toilets" stage. During this stage you are as likely to negotiate funding as you are to clean the restrooms. 

As the business begins to mature, everything shifts and becomes about facing threats and scaling. So what does it take to scale your business? Here are some real-world insights.

Before we dive into the list, though, keep in mind that scaling a business is not a prescription. The steps that work for one business may not work emphatically for another. Your job is to filter the essential tenants of that insight and apply it to your situation.

With that in mind, let's get started!

When Scaling Your Business, You Must Shift from Founder to CEO

As a CEO, your primary responsibilities shift from daily, hands-on implementation to nurturing and protecting the culture of the organization and creating the strategy and vision to guide the organization forward.

Culture can be a difficult thing to scale. Some leaders seem to foster a thriving culture naturally. Others may struggle. What do you do if building a strong culture is not your strong suit?

Repetition, Repetition, Repetition

How many times do I have to repeat it? I've said it all before. They should just know. These thoughts, and others like them, will fill your head as you grow from startup founder to business owner and manager.

You are the chief brand evangelist. In every situation and at every opportunity, you are responsible to spread the message of your brand. As entrepreneurs, we like to move fast. Tell me once, and I've got it! But as a business owner, you can never stop repeating your mission, vision and values. It's now your full-time job. 

During the startup phase, you could work directly with your team. The organization was completely flat. You may have been coding all night right next to your technical cofounder, or perhaps you made sales calls with your sales team (or maybe you were the sales staff!). As you scale your business, you will add new team members more quickly than you ever have before, and it may be no longer possible to work as intimately with every member of your team.

You'll probably have someone hiring for you, doing new employee orientation and then managing those employes. But in the end, you are responsible for their outcomes.

In everything you say and do, you must be the living, breathing embodiment of your company's core values. If you aren't or don't, then your team will quickly leave them behind as well. You may then look up in shock to realize you are heading a company you barely recognize.

Trust But Verify

The qualities and skills that got you to this point as a startup founder won't get you to where you need to be as the CEO of a growing organization.

When you started your business, you probably observed a problem and developed a solution to solve it. That process, in the early stages, relies heavily on your gut instinct and intuition. It is creative and exciting, and most entrepreneurs only see the potential.

As you grow into a CEO, you will experience a transition from operation by intuition to a reliance on data. Your intuition as an entrepreneur is important, but as the company grows verifying your instinct with data is a tool that can make you an effective executive.

Strategically, the ability to analyze and interpret data will help you recognize potential opportunities that may have been unseen or will alert you to miscalculations or obstacles lining the way. Many entrepreneurs fail to make the transition because they are used to operating solely by instinct.

Facing the Threat of Competition When Scaling Your Business

As soon as you achieve market fit, you will be confronted by competition in one form or another. Some assaults will be more direct than others. The difficult thing about competition is that it can never be predicted. Even if it is expected, it will often appear seemingly out of nowhere.

The problem with these challenges is they are a punch in the face while you are casually walking down the street. You have no idea where they are coming from.

-Brian Chesky, Airbnb

Leverage whatever situation comes to you for the company's advantage. If a competitor pops up, determined to take you down, identify what they are hoping to accomplish (besides neutralizing the threat of your company in the market).

What is their strategy? What is their horizon? What do you do better than they do? What promise can you deliver on consistently that they cannot? What tactic do you need to employ to ensure your longterm survival?

These are all questions that a confrontation by a competitor will cause you to ask. Here are some tips when facing competitive challenges.

1. Know Thyself
Clarity is essential as you scale. You, as the CEO, have to be absolutely clear on your mission, purpose, and values. Reacting and responding to your competitors is an ineffective and inefficient strategy for overcoming competitive challenges. Commit to the vision you have for building your business and focus on your "sweet spot."

What do you do best (or what can you do best)? What is the experience you can create for your customers that your competitors can't or won't dedicate themselves to creating?

2. Pivot or Speed Up (or both)
It may seem like I'm saying to double down on what you have been doing when I say to focus on your vision, but that's not necessarily true. I am really saying that you must be 100% clear about your vision. In order to win, you must still be agile, flexible and responsive.

You may not need to shift your entire business plan or strategy, but you are (usually) the smaller, leaner organization and can shift more effectively than your competitor. Use that to your advantage. Leverage your competitive challenges to propel your business forward.

A direct confrontation by a competitor may open up new opportunities to scale more quickly than you may have planned. This may be scary, but it can also be a catalyst to propel your company forward.

If you are clear with your vision of growing the business, you can make smart decisions that will position you to take advantage of new opportunities you may not have even imagined before. Yes, it is a calculated risk, but it can also produce incredible results.

Two Keys To Success in Scaling Your Business

Chesky noted two very specific qualities that seem to distinguish those who successfully scale their business from those who do not: Intelligence and Curiosity.

Entrepreneurs who begin to believe their own hype struggle to grow their business. Scaling a business is largely an exercise in pragmatism and efficiency. Keeping an open mind and an incessant pursuit to uncover new and better ways of doing what needs to be done will lead you to the people and tactics you will need in order to grow your business. As soon as you start to believe that you know it all, you have lost in the game of scaling your business.

I think being a CEO in a hyper growth company is every 6 months you have a completely new job. It’s like if you were a pro bowler, then became a pro football player, then a pro hockey player, etc. Every stage is a completely different sport.

-Brian Chesky, Airbnb

As the CEO of a quickly growing company, every day is different and you must often learn new skills faster than you can implement the old ones. Can you keep up?

The same qualities that have made you a successful entrepreneur--the ability to adjust quickly and pivot--will be required in new and more sophisticated ways.

Take pride in the accomplishments you have achieved as a startup founder, and recognize the challenge that lies before you as the CEO of your growing business.


Read Chesky's complete interview at Stanford

Photo Credit: PascalCC 2.o