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You don’t have to be a Harvard dropout or the son of an emerald mine owner to become an entrepreneur. Anyone can start a business, and anyone does. In our time we’ve partnered with hundreds of startups and founders, all of who brought their own spin to business birth.

Whatever your unique origin story and expertise is, there are several types of entrepreneur it’s helpful to be aware of. Each mould is shaped by its own set of strengths, weaknesses, opportunities and threats that connect and differentiate you from your peers. To help you zero in on which one you fit best, we’ve narrowed down the five types of entrepreneur in the contemporary startup economy. Without further ado:

  • 1. The Buccaneer Entrepreneur
  • 2. The Saviour Entrepreneur
  • 3. The Maestro Entrepreneur
  • 4. The Hybrid-Visionary Entrepreneur
  • 5. The Buyer Entrepreneur

1. The Buccaneer Entrepreneur

The Five Types of Entrepreneur

The Steve Jobs archetype. The square peg. The round hole. Where the ordinary person may see a lost cause, they see opportunity. Although they may not have Oxbridge running through their veins, they’re open to new ideas and are blessed with natural creativity. This makes them lovers of outside perspectives who aren’t afraid to ask for help.

This type of entrepreneur is never satisfied with their first idea, certain that things can be improved, ever pivoting, ever iterating, ever improving. A surefire way to know if you’re this type of founder is the all-consuming thought of “what can we do differently?” bouncing around your brain. They are serial idea machines, and are prepared to perform mental gymnastics to find the idea that fits their problem.

To fuel this desire to learn, they’ll devour every ounce of wisdom that can push them closer to their vision. In terms of format, they’re not fussy. Whether it’s a podcast, book, Ted Talk or a conversation, as long as it helps them get ahead of the competition, they’ll welcome it.

While they may not be an artist, they’re still highly creative. This may not be in the traditional sense, but then again, nothing about this type of person is ever traditional. They’re like the opposite of Schrödinger’s cat; you know for sure they’re not in the box. They will apply their creativity and problem-solving skills to everything they do.

We tend to have explosive ideastorms with them, innovating and iterating their ideas together until we strike something golden. That’s when (thankfully) process kicks in; groundwork, design systems, research, plans, you name it.

Inspirational Outfly partners who fit this mould: Jack Cohen (Massless), Dezzi McCausland (Q Shoreditch) and Seb Ross (The Society Company)

2. The Saviour Entrepreneur 

The Five Types of Entrepreneur

This entrepreneur is on a mission to solve a specific problem. Which sounds like most entrepreneurs right? The key difference here is this entrepreneur has a clear vision. (Remember, having a creative idea or spotting a gap in the market is not the same thing as having a vision.)

But where does the Saviour’s mission come from? Well, like all good things, it’s homemade. Not in the fashion of a generation-old recipe, but in the sense that it has directly affected the entrepreneur themselves, or their loved ones. Upon seeing this problem, they want nothing more than to solve it. And (spoiler alert) they will.

One great example is Alex Nash, founder of Alcuris. After his grandfather was diagnosed with dementia, Alex searched for a way for him to be looked after while still holding on to his independence, only to find that it didn’t exist. So Alex made it exist. Flash forward and Alex’s app is now making a difference to families across the United States. The difference between solving a problem and solving a problem as a Saviour is that Saviours don’t stop. They realise the wider implications of their mission, the impact they can have, and that big problems aren’t solved quickly. The realisation that their problem isn’t just local is where their vision begins to form.

Their journey reflects an obsession with the future, and of improving that future for the better. They aren’t satisfied by a simple improvement in industry. They want improvement on a huge, planet-sized scale. The Saviour doesn’t just want to help those closest to them, they want to help every single person who has this problem.

Once their vision is in place, there’s no stopping them — they’ll do anything to make it a reality, and will push ahead full throttle to get there.

Inspirational Outfly partners who fit this mould: Simeon Quarrie (Vivida), Dami Hastrup (Moonhub) and Jillian Kowalchuk (Safe & The City).

3. The Maestro Entrepreneur

The Five Types of Entrepreneur

On the other end of the risk-taking spectrum is the Maestro. With a red brick University in their past, and the words “senior manager” or “director” floating around their CV, they are solidly risk-averse but immensely experienced. They don’t characterise themselves as disruptors and put their trust in tried and tested methods. Hey, if it’s not broken, why fix it?

Their knowledge is bottomless. They’ll know every small detail of their industry, and have the insight to see where it’s going. Interestingly, while they may have the understanding needed to change the game, that isn’t their goal. CEO from day one, they are masters of delegation, which is the attribute that gives them exactly what they want —- a team of highly skilled professionals ready to knuckle down. Using their corporate experience to deliver on ambitious targets, the Maestro will carve up, plan out and distribute workloads across employees, contractors and outside experts.

Detail is good, being prepared is better. They’re likely to raise VC early, rather than relying on the exposure of a frantic bootstrap, and will use their funds to draw up a meticulously designed business plan that lets them forecast every aspect of spending and revenue. The Maestro thinks like a chess grandmaster, always one step ahead, always considering potential repercussions before making their move. As the tortoise knows: slow and steady wins the race.

By the time they sit down with us, it’s because they need a team that can help them scale. Revenue and impact are already being made, but it’s time to grow. For this, they need proven design innovation expertise that can help them design, deliver and manage the improvements that will fuel their next stage of growth. Calculated risk done right — it’s the magic formula to scaling for any established Maestro.

Inspirational Outfly partners who fit this mould: Claire Cockerton (Plexal), Poppy Szkiler (Quiet Mark) and Carlos Monreal (Plastic Energy).               

4. The Hybrid-Visionary Entrepreneur

The Five Types of Entrepreneur

These types of entrepreneurs are experienced in their industry but haven’t quite reached the level of master. By seeing something that could be done better, and recognising the way to do it, they can create the vision themselves, rather than through a skilled team of workers.

Whilst having the heart of a daredevil, their risks are much more calculated, a middle ground between well-thought-out and throwing caution to the wind. The Hybrid-Visionary strikes a cool balance. They like the idea of spontaneity but are much more likely to want to do it with a team in place.

Venture capital isn’t the first stop on their journey. Instead, they try to find a community of like-minded people to bring on board. This marks the beginning of their journey as a co-founder, rather than a Han Solo. They’ll surround themselves with supportive and collaborative souls that act as the perfect counsel for any idea. Acting as the perfect lion, they will always seek validation from the rest of their pack before making any sudden moves.

Maybe they didn’t come up with the initial idea, but they’re a dab hand at spotting a great opportunity. Their flexibility and willingness to work with solo entrepreneurs means they’re excellent at building a vision and are perfect team players.

Partners are a big part of the Hybrid-Visionary’s experience, and finding those with shared enthusiasm, shared values and bucketloads of chemistry isn’t always easy. They want radical insight, someone who can create a spark and drive forward the progression of the team. Someone to share the load and act as a sound board for ideas. And, most importantly, someone with a complementary (not competitive) skillset. The Yin to their Yang.

Despite all this, the Hybrid-Visionary is probably capable of making it on their own. But the opportunity of finding a partner on their wavelength is often too good to resist.

Hybrid-Visionaries are nestled comfortably between Maestros and Saviours. When they find their way to us, they’re looking for a support network. They’re after somebody who can deliver an influx of skill, innovation and vision that will help them scale faster.

Inspirational Outfly partners who fit this mould: Hussein Cholkamy and Sarah El-Taher (Eyrus), Rezene Woldeyesus and Naomi Bottrill (Love Language).

5. The Buyer Entrepreneur

The Five Types of Entrepreneur

With a pile of successful, thriving businesses in their wake, this type of entrepreneur is already established, with a highly successful business brain to boot. Whereas other entrepreneurs see opportunity, these types see viability. They’ll carefully study a business, acquire it and find the most suitable person to run and grow it. These magpies are experts at spotting diamonds in the rough and boy do they know how to make them shine.

Their diamonds range from expert team members to market potential — they know what they’re looking for before they even start looking. But Buyers are also realistic about their goals and, thanks to their experience growing small businesses, they’re the perfect gardener.

There’s very little risk for these types of entrepreneurs. Things are always easier when the foundations are already there, and they’re experts on making the most of what they’ve got. As a result, they can focus purely on building something that has already gone through many twists and changes.

It’s not always plain sailing, and thanks to COVID-19 it’s even more difficult for small businesses to stay afloat, no matter who is at the helm. But, luckily for the Buyer, they’re experts at spotting promise in smaller businesses, and have a knack for navigating those inevitable market storms.

Inspirational Outfly partners who fit this mould: James Ewan and Harry Droop (Boreland Loch Tay).


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