The Truth About the 3 Different Types of Entrepreneurs

By Sean Ogle •  Updated: 11/05/21 •  15 min read

This is a guest post from Jacqui Pretty. Jacqui is the Founder and Head Editor of Grammar Factory, which helps entrepreneurs write awesome books so they can establish themselves as thought leaders.

Imagine this scenario…

You sign up for a business course or coaching program.

Your coach makes you delve deep into the passion behind your business. They open your eyes to new possibilities and endless horizons. They build your confidence, telling you about the difference you could make and the impact you could have on the world.

You realize that you’ve been playing too small.

You need to get bigger, build your audience and reach out to new markets. You have an important message the world needs to hear, and you won’t stop until they do.

After six months of working fourteen hours a day, seven days a week, you find yourself looking at your bank balance.

‘That can’t be right,’ you think as you run the numbers.

You’re making the same amount you were making six months ago. You look at your list and see that, even though you have some more subscribers, the difference is negligible. You look at your website traffic and see that it hasn’t gone up either.

You then start to think about the last six months. You’ve stopped seeing your friends and family.

You’ve been meaning to go on a trip, but have put it off month after month. And those personal interests? You know, learning the guitar or tae kwon do? They’ve fallen by the wayside with everything else.

You wonder, ‘How can I have nothing to show for all my hard work? What was I doing it for?’

You realize you’ve moved away from what you wanted

When you started your business, what did you want?

Quit your job?

Have more time to pursue your passions?

See the world?

Call the shots in your own life?

Yet, you realize you don’t have any freedom. Your business – the vehicle that you thought would take you to your freedom – has become an engine that constantly needs to be fed.

Instead of skydiving in Jordan, smoking cigars in Cuba, or dipping croissants into your café au lait in France, you’re shoveling coal into the furnace.

If you already had a somewhat-established business before you decided to change the world, you might even feel like you’ve gone backwards.

You had a steady stream of freelance clients, most of whom had been referred by past happy clients. Sure, you weren’t earning a fortune, but it was enough for you to be independent, to manage your own time and to have the freedom to work from anywhere.

To maintain that business, you didn’t need a big email list or a thriving social media presence – because they found you through word of mouth, you could just focus on doing your work and doing it well.

You start to wonder, ‘Was all of that work for nothing?’

The issue isn’t that your business course or coach was wrong. The advice they gave you was probably great advice for changing the world, making an impact, building an audience and becoming a leader.

The issue is that it might have been the wrong advice for you.

The 3 different types of entrepreneurs

According to John Warrilow, author of Built to Sell, there are three different types of entrepreneurs:

Take a closer look at each one:

Mountain Climbers want to change the world. They want to build empires, change the way things are done and may want to take down an enemy. When you ask them about their business, they will talk about their vision for the future.

Freedom Fighters want to do things on their own terms. They are motivated by freedom and independence and loathe being tied down. They’re the type to talk about the lifestyle their business is creating (‘I get to travel for six months of the year!’) rather than what they’re achieving with their business.

Different types of entrepreneurs: Sean Ogle is a Freedom Fighter

Yes, Sean definitely is solidly in the “Freedom Fighter” camp.

Craftspeople just want to do the work. The programmer wants to program, the designer wants to design, the writer wants to write and the accountant wants to work with numbers. These are the sort of entrepreneurs who say, ‘Business would be great if it weren’t for the clients’.

According to Warrilow, about 75% of entrepreneurs are Craftspeople, about 23% are Freedom Fighters and about 2% are genuine Mountain Climbers.

In other words, most entrepreneurs don’t have the desire to build empires, climb (metaphorical) mountains and change the world. They want to do work they love and they want to have a great lifestyle while they do it.

If you’re reading Location Rebel, I’m guessing you’re a Freedom Fighter. You want the freedom to work from anywhere. You want to sit on a banana lounge with your laptop while holding a cocktail with a little umbrella sticking out of it.

Unfortunately, most business courses today aren’t designed for Freedom Fighters ( or for Craftspeople.)

Note: Location Rebel Academy is designed for both Freedom Fighters and Craftspeople 🙂

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The problem with business courses today

The problem with most business advice today is that it’s targeted at Mountain Climbers. This is why so many courses and coaches talk about finding your why, having a deeper purpose, making an impact on the world and being an inspiring leader.

This is then compounded by the fact that the 2% of entrepreneurs who are Mountain Climbers are the ones who are getting 98% of the coverage.

The problem is that this sets up 98% of entrepreneurs (the Freedom Fighters and Craftspeople) to have expectations that aren’t in alignment with who they are and what they want to do.

As a Freedom Fighter, you don’t particularly want to change the world or be an inspiring leader. You want to live an amazing lifestyle on your own terms doing work you love.

That’s okay.

There’s no point in artificially creating a purpose that sounds good to the outside world (or to your business coach) if you don’t genuinely want to achieve that purpose. There’s no reason why you can’t still do amazing work and have happy clients if your end goal is freedom.

Unfortunately, it’s a little difficult to come out and say that when everyone’s harping on about the importance of a bigger purpose.

The entrepreneur identity crisis

Things really start to get tough when you are trying to be something that you’re not. In most cases, it’s when Craftspeople and Freedom Fighters are trying to be Mountain Climbers, instead of building businesses based on who they are and what they want.

The Craftsperson

Take the Craftsperson, who loves the work but doesn’t really like the rest of the business stuff. I think of these people like the ‘talent’ in Hollywood. The big stars don’t need to manage their calendars or emails or transportation or even their health and fitness regimes – they have a support team that manages all of those areas for them, which means they are free to show up on a set or on a stage and practice their craft.

In business, the equivalent might be outsourcing everything that you don’t love to a support team.

If you’re a photographer, for instance, you can focus on the photos (and perhaps post-processing, if you also like that), while a VA manages your emails and appointments and a customer care person takes care of sales calls, customer feedback and communication.

The Freedom Fighter

If we take the Freedom Fighter, on the other hand, the focus is more on the motivation behind the work (freedom and independence) rather than the work itself.

This means that they might be more comfortable taking on the supporting roles in the business as well as delivering the main product or service, but that their business should never feel like it’s tying them down.

So if you’re not going to build an empire, what should you be doing? I’ve seen two approaches when it comes to creating a great lifestyle business – staying small or growing big fast.

One More Thing…

Another approach for the Craftsperson or the Freedom Fighter is finding a job. I know, I know – I’m not supposed to use the J-word when writing about entrepreneurship, but it’s not quite what you think.

Not all jobs have to be the 9-5 cube farms that you have in your mind. There are more options, working with other entrepreneurs, and startups, for example, than ever right now.

But the fact is that if you don’t enjoy and aren’t good at all of the other cogs that are turning in your business machine, consider it’s better to work in someone else’s business doing what you love than to build your own.

The two business pathways for Freedom Fighters

The easiest business pathway for the Freedom Fighter is building a fulfilling and sustainable small business.

Building a “Small Business”

You are the main provider of your business’s service.

Because you are the one providing your business’s service, you don’t need to worry about hiring, training and monitoring employees.

This means your capacity to take on work is limited, so you need fewer clients to be fully booked.  You don’t take on the expense of new employees, so you don’t need to take on more work to pay for that expense.  And you don’t need to spend the time training and monitoring employees, which gives you more time to do what you love.

You charge a decent rate for your service.

You want to charge enough for your service that you don’t need to work ridiculous hours to make ends meet.

How much you need to enjoy life will vary depending on your circumstances and the type of lifestyle you want to create, but the goal should be charging enough so you have enough income coming in to support your lifestyle, and enough time to enjoy that lifestyle.

The service needs minimal infrastructure and support.

Physical offices, employees, freelancers, software, marketing materials and the other things that surround your core service require time and money to sustain.

While every business has some non-negotiable infrastructure requirements (in my case, the non-negotiables are Microsoft Word, Gmail, Xero, MailChimp, WordPress and my domain and webhosting), in many cases, we add on things we think we need that we really don’t.

If you have infrastructure and support you don’t need, let it go. The less time and money you need to spend, the more time and money you have to create the life you want.

Your main focus is delivering a great end result for your clients.

Great end results lead to repeat business and referrals.

And, if you charge a decent rate for your services and your business stays small (in other words, you don’t increase your capacity to take on new work by hiring more people), it can survive on repeat business and referrals for years, if not indefinitely.

This means that building a list, blogging, vlogging, social media, networking and everything else entrepreneurs do to bring in new clients becomes superfluous, which frees up your time to focus on doing great work and enjoying an awesome lifestyle.

Building a Bigger Business

The second, more challenging, pathway is building a bigger business. The key to doing this well is to grow your big business as quickly as possible.


Because there are predictable stages of every business’s growth, and not all of them are positive. By growing quickly, you can get through those difficult stages, or struggle zones, quickly.

This theory comes from Glen Carlson and Daniel Priestly, the founders of the Key Person of Influence Program in the US, the UK, Australia and Singapore, who argue that there are five clear stages to an entrepreneur’s journey.

These stages are:

  1. Startup: The startup stage is when you are launching your business. You have a lot of excitement and enthusiasm, but there is no money or structure yet.
  2. The first struggle zone: At this stage there is a lot of competition in the market and the entrepreneur needs to work hard to bring in money. This means they have very little time, money’s tight and they’re often stressed or burnt out as a result. Priestly and Carlson define these businesses as having fewer than three employees and generating less than $300,000 in revenue.
  3. The lifestyle business: When I said the second pathway for the Freedom Fighter is growing big fast, this is what I was talking about. Your revenue in this stage is between $300,000 and $2 million and you have between three and twelve people on your team. At this stage, your revenue is strong but your overhead is low, which gives you the freedom and the finances to enjoy the lifestyle you want, and the support to take a break from the business as your team can take care of it.
  4. The second struggle zone: This stage happens once you’ve created a lifestyle business and you think, ‘I’ve gotten pretty good at this – let’s get bigger!’ The problem is that growing beyond the lifestyle business stage requires drastic change – you need to hire more people, take on more debt, open more offices … and suddenly your expenses go through the roof. While your revenue increases, because your expenses have gone up so much, your profit falls dramatically. This then causes more stress.
  5. High performance: The fifth and sixth stages are the high performance zone. You have a team of over 50 people, have presence in several markets and have people wanting to buy your business from you. Your profits are over $10 million and you take on the role of the visionary leader.

There are a couple of things I’d like to clarify about these business stages.

The first is I believe it’s possible to have a great lifestyle business as a Freedom Fighter with lower profit and staff numbers than what is outlined in the previous discussion.

This is what the small Freedom Fighter business is about – because you are providing the service and your expenses are low, you get to enjoy the profits and don’t need to work an insane number of hours to do so. Yes, when you take time off the business will stop, but if you’re charging a decent amount for your services you can manage this by putting income aside in a holiday fund.

The second thing is a Freedom Fighter’s ‘big’ business is very different to a Mountain Climber’s ‘big’ business.

A Freedom Fighter’s big business is the lifestyle business defined in the previous stages – up to 12 staff and up to $2 million in revenue. The Mountain Climber’s big business is the high-performance business – over 50 staff and over $10 million in revenue.

If you do decide you want a bigger business, the key is growing it quickly, otherwise you could get stuck in the struggle zone – more stress, more time and less reward – until you might forget why you even started your business.

Closing thoughts: Remember your ‘why’

Business courses and business coaches have a lot to offer any entrepreneur.

They can alert you to hidden opportunities, help you avoid mistakes, help you optimise what you’re doing and push you to achieve more than you thought was possible.

The key in any course or coaching program is to remember why you got into business in the first place.

Yes, building a $50 million company, becoming a household name and ending poverty are all noble goals that will excite and inspire you, your staff (if you employ any) and the media, but that excitement and inspiration will only be sustained if it’s a genuine goal.

Going on a crusade is great in theory, but if it isn’t what you really want, then you could spend a lot of time, money and energy to make very little progress.

Instead, be honest.

Do you really want to change the world? Or do you want to live life on your own terms and/or do the work you love?

If you want an awesome lifestyle doing work you enjoy, then focus on doing amazing work, charging decently for it and enjoying the spoils of your labor.

Leave world domination to the Mountain Climbers.

About the author

Jacqui is the Founder and Head Editor of Grammar Factory, which helps entrepreneurs write awesome books so they can establish themselves as thought leaders. Download the first two chapters of her new book Book Blueprint: How any entrepreneur can write an awesome book for free at

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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