Interview with an Entrepreneur: "Why do you do what You do?"

Paul Myers MBA

Three questions that I asked a serial Entrepreneur

Image by StartupStockPhotos from Pixabay

I was fortunate to interview a number of Entrepreneurs for research projects in the last couple of years. Below is one that I’d like to share with you.

Enjoy folks!

Q1 — Why do I do what I do?

What makes me tick / what motivates me? This is by far the toughest question. I have thought about it many times over the years and have not found a simple answer that sits right with me.

Here’s where I’ve gotten to so far:

Desire to achieve my full potential

Ever since I was very young, I’ve felt the presence of a very strong power inside me (i.e. the potential of a human being). I’ve always felt that the world is a place where there is an unlimited opportunity and find it very exciting to think about the endless possibilities.

I can’t tell you where I got these beliefs from…but I imagine I got some of them from my mother / from her encouragement and belief in me.

Disappointment in myself fuels the hunger to drive change

I feel I had the potential to do well at swimming, but never realized my full potential. While I had talent and guts, I didn’t apply myself and expose myself to the pain / physical discomfort that was required to enable me to realize my potential. This feels like a waste and a shame.

It’s like there was an amazing life-changing adventure ahead of me and I didn’t open the door to it and experience it.

I felt that I could have done well in school…but know I didn’t achieve a fraction of what I could have. In my third year in college, I started to apply myself, worked hard, and began to get quite a few first-class honors results. Ultimately my combined score was 2% short of a first (Distinction), I was disappointed in myself that I didn’t bring it home.

The above disappointments just fuelled the hunger inside me at that time. I felt strongly that I had what it takes to become successful (in my view of ‘successful’ at that time in my life anyway) and really wanted to make it happen.

When I was half-way through college, I began to think about business as a way for me to ‘achieve my potential’ and prove to myself that I had what it takes to be successful.

Looking back now, I realize that I've been doing entrepreneurial activities since age 10…but this was never obvious to me until much much later in life — it was just what I did, just who I am.

The reason I started working hard in college was to get into an investment bank after I made this my goal. The irony is that investment banks choose candidates based on their results before their final year — by the time they get their final results, candidates are already working for the banks.

It was just what I did, just who I am.

Tasting success makes me hungry for more

It wasn’t easy, but I fortuitously managed to get into a summer internship at Lehman Brothers. The following summer, I again fortuitously managed to get into a summer internship at another investment bank — this time Chase Manhattan Bank.

Based on working for two investment banks before I left college, I thought I’d have my pick of graduate investment banking programs when I left college.

Not so. Not so at all.

While I applied to all banks and brokers (about 25 applications), I was only invited to 3 interviews. From there, I was offered 2 jobs, one for an investment bank and one for a broker.

I chose to join Merrill Lynch (ML) where I stayed for 5 years.

One in 10,000 chance

It wasn’t until many years later that I found out that over 10,000 candidates applied for 25 positions with the bank in London. The truth about investment banking (which I didn’t know at that time) is that the hardest thing is getting in, in the first place.

From the minute I joined ML, I applied myself as I had never applied myself before, apart from the summer internships at the other banks where I worked incredibly hard too.

I felt like I had been given a last chance to make something really special of my life / go on one of those mysterious adventures that I missed when I didn’t walk through the swimming door of opportunity.

Over the following 5 years, I worked incredibly hard and achieved very good results.

I started to be paid relatively well for someone in my position at the time, with annual bonuses of USD 250k. While it felt good to be doing something I was good at and to begin to be rewarded for it, I was still hungry and getting hungrier (not for money).

Some frustration begins to set in and my entrepreneurial trait comes a-knocking again

One of the main reasons I really liked the work I did in the bank was that I was part of a very small entrepreneurial group. There were initially 5 of us and we were extremely nimble.

I was basically free to roam around the bank looking for opportunities and had access to almost all companies in the world to pitch ideas to.

Over time this became a global group of about 40 and things began to change as we made more and more money (we were making over USD 150m a year.

Other individuals and groups in the bank began to take more notice of what we were doing.

  • They started to compete with us.
  • Rules were put in place.
  • Barriers were put up.
  • The regulatory environment began to change.

Everything became much more political. My manager began to take credit for all my ideas and I began to feel frustrated.

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Testing the water

During my 5 years at ML, I tried to pursue some entrepreneurial projects such as buying a houseboat in a cheap area with a view to ‘importing’ this ‘real-estate’ into an expensive area in London and invested in property.

believe the houseboat / importing real-estate concept was good, but the execution was poor, mainly because working in a bank like that leaves you with no time to properly work on extracurricular projects — it’s one of the reasons you get paid so much at a bank.

The entrepreneurial projects were generally disasters but the property investing worked-out very well.

By the time I had been at ML for 5 years, I had made more money in property than I had at the bank — with less than 1% of my time — no exaggeration.

Frustration at work from the increase in internal politics/increase in regulation/barriers and decrease in that ‘entrepreneurial experience’ as our group became larger, more ‘above the radar’ and more profitable combined with the frustration that I had lots of ideas that I wanted to do myself but didn’t have the time because I was working so much at the bank.

This led me to the conclusion that the right thing for me to do was to simply leave the bank. It was 2001.

That was a very unusual thing to do. I wasn’t ‘wealthy’ at the time that I left, but it was inevitable that I would become very financially wealthy if I had stayed — my immediate boss ended-up making over USD 100m personally.

Regret test

But to me, I simply applied the ‘regret test’:

If I stayed at the bank, made a shit load of money, would I regret not listening to the entrepreneurial call that was like a really strong magnet?

The truthful answer was ‘yes, I would regret it’ — I knew this to be the case. And so my decision was simple, as soon as I realized this — I just had to be true to myself.

Overcompensating / making-up for lost time

I was like a bear out of a trap once I left the bank. I went with my entrepreneurial gut and continued to focus on property used my tax skills to help me raise capital.

In time I hoped to have more opportunities to widen this to venture capital and private equity projects.

Over the following 5 years, I made a lot of money, attracted and retained quite a lot of talent and took over another company.

While I had managed to acquire EUR 100m (circa GBP 75m) of property development assets (with an ultimate end value in excess of GBP 300m), I still didn’t feel that I was even scratching the surface — I felt that so much more was possible, that I hadn’t even gotten started properly.

It was never about the money for me. While my ‘net worth’ was probably around the GBP 10m mark at one point, I didn’t even own a car and lived in rented accommodation.

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Fear as motivation

I had borrowed a lot of money from banks, from ‘friends and family investors, and professional investors.

I never intended to put myself in a position where I owed huge amounts of money to friends and family. I was energized by the excitement of making money and sharing my ‘winnings’ with them.

I didn’t stop to think about what could happen if I was not able to repay them.

As time went on, the amounts of money continued to increase. The property teams that I had assembled/acquired were hungry and I spent most of my time obtaining new capital to ‘feed’ them.

I began to become more and more aware of the risks that I was exposing myself and my friends and family investors to. The desire to repay all friends and family debt began to get stronger and stronger in me as time went on.

But it wasn’t easy to achieve, for many reasons. I wound-up in an unusual place where I ended-up borrowing more and actually increasing my risk exposure, with a view to making more money that would enable me to repay the friends and family investors and still have a large property development group in place.

The fear of letting down friends and family was a huge motivating factor during this time of my life.

What motivates me today?

Fast forward to today. What motivates me now? This is still difficult to totally answer.

I can still feel some of the old drivers — namely the feeling that I haven’t yet really succeeded at anything (perhaps other than for short temporary periods) and still feel the strong desire to prove stuff to myself.

A big part of me would really like to repay all the friends and family investors who lost money when my group collapsed in 2008.

However, I can’t be constrained by the events of the past and have had to accept this.

This desire is no longer a driving force in my life…but ‘that would be a really nice thing to do if I ended up making a lot of money to enable me to do so.

I have mellowed in other ways: one of my big motivating factors these days is freedom. This is hilarious to talk about as, in many ways, it’s clear that a lot of the projects I get involved in and positions I put myself in, significantly reduce my freedom, temporarily at least.


However, by ‘freedom’ I mean the freedom to pursue the entrepreneurial projects that I want to pursue, regardless of how difficult they are, how much money they would require, the contacts that may need to be made etc.

Deep down, I think this was a huge driver during my years in London too:

I wanted to create a financial group where I had the ability to potentially pursue any project on the planet that I felt passionately about.

"Freedom" is probably the single word that gets closest to answering your question: "what makes me tick / what motivates me?"

If I were to rephrase, it would probably be:

The freedom to choose.

I would like to have total freedom to choose how I spend my time, the freedom as to where I spend my time,

The freedom with who I spend my time with, including time with myself.

The freedom to choose what entrepreneurial projects I take on, including having access to whatever capital is needed to take them on.

The freedom to choose who I partner with / work with on each entrepreneurial project I take on.

The freedom to express myself, follow my gut, make mistakes on lots of entrepreneurial adventures.

So, in conclusion, the desire for freedom (or perceived freedom) in its many guises is probably the biggest motivating factor for me at the moment (which encompasses the strong desire to get out of debt — as debt restricts my freedom…and therefore getting myself out of debt (again) is a huge motivating factor for me right now).

Other factors are a desire for adventure, excitement, personal challenge/growth and development and to have a positive impact on the world are also part of my motivational make-up.

Q2 — What are the biggest challenges and/or opportunities that you see in your line of business?

Biggest Opportunities … hmmm!

Using digital platforms to enable people who notice or observe opportunities, to make us aware of those opportunities. For example, as part of a community of opportunity-hunters with a lack of capital, to pick but one illustration of many.

Using digital platforms to match investor capital and funding to (the best of) those opportunities

The unleashing of talent

The rapid improvement in technology and communications has leveled the playing field for all.

Almost everyone has access to a global audience of billions from the video-camera on their smartphone, tablet or laptop. Anyone can open up a global shop within minutes. For free.

any of the competitive advantages that large corporations once held are fading away. Individuals and small groups of individuals are increasingly creating more value from their bedrooms than many large corporations who have been around for decades.

They are having a bigger impact on the world and getting rewarded accordingly.

These rapid developments significantly level the playing field and obliterate competitive advantages that corporations have enjoyed from technology, monopolistic distribution networks, access to capital and more.

The net result is that talent is now the determining factor: Those with the talent have the best opportunities of succeeding…and those without it don’t stand a chance.

Those businesses that can attract, enable, facilitate and support the best talent around will have a significant competitive advantage over those who fail to do so e.g. large stagnant corporates.

In my line of business, I believe the biggest opportunity is in becoming better and better at attracting, identifying, supporting, facilitating, enabling, and retaining talent, in a whole manner of different ways — finding really talented individuals and teams and helping them to naturally shine.

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Biggest challenges

The flip side of the leveling of the playing fields and the reduction/elimination of middlemen is that there are many many more voices out there shouting to be heard and vying to connect directly with their audience.

There is immense competition for people’s attention and this is increasing. It is not enough to have an amazing new product, shop, story, video, piece of music if nobody notices it amongst the millions that are vying for our attention.

It is not true to say that the talent will rise naturally to the top.

Some of the most talented individuals are introverts whose talents do not include drawing attention to themselves. Individuals now have direct access to their audience. TV networks no longer control the media.

One of the effects of this is that the power and influence of celebrities including business celebrities, such as Richard Branson and Bill Gates, has increased dramatically and are continuing to do so.

While there are huge opportunities to connect directly with a global audience for everyone, it's very challenging for an unknown to enter the market and get some of that attention.

Some of the most talented individuals are introverts whose talents do not include drawing attention to themselves.


At the moment, we’re seeing the development and proliferation of peer-to-peer investor networks.

Technology platforms enable many investors to each invest a relatively small amount directly in a project/business that, when combined, adds up to a very meaningful amount for the projects.

While this is partly an example of the disintermediation i.e. removal of the middlemen of commercial lending banks, it is more than this:

Never before has individuals had access to so many investment opportunities.

It is now possible for someone to efficiently invest or lend EUR 5 or 50 into a company or project. Before technology made this efficient, the cost of doing this previously was inconceivable.

As a result, the venture capital, private equity, property, and other non-public market investment opportunities of the world were restricted to the richest 1% in the past.

This is changing.


Technology is enabling the efficient transfer of capital from those who have it to the opportunities and entrepreneurs who need it.

However, the regulation still remains a challenge. Similar to tax, the regulation of financial investments is regulated on a country-by-country basis whereas capital is competing in a global world.

While regulatory restrictions can result in opportunities, regulatory restrictions also pose challenges.

For example, at the moment it is not practical for any non-US company to seek capital from US individual investors over peer-to-peer web-based networks despite the fact that:

  • (a) some US investors would really like to invest some of their capital in non-US opportunities and
  • (b) many non-US entrepreneurs (who may have many online US customers already) would like to access US-based individual investors.

Similar problems currently exist in relation to most cross-border web-based investment opportunities that involve individuals. The fact that each individual country (more or less — the EU has streamlined a lot of its rules for its members) has its own regulatory system designed mainly to protect its own citizens is challenging in the context of the development of truly global peer-to-peer investment digital networks.

Q3 — What leadership traits and characteristics (or strengths and weaknesses) do you exhibit within your field of expertise?

Okay, let me think…

My strengths include

  1. I am an open-minded, unconventional, creative thinker and notice opportunities that most others don’t. I’m good at taking the nub of an idea and developing it into a bigger opportunity. I’m strong at communicating my ideas to others which enables me to attract capital and talent to progress certain idea and opportunities (leadership).
  2. I am not afraid to do things that others have not done before or to attempt to do things in ways that are different from the ways they have been done in the past. In fact, I probably seek these opportunities out as part of my experimental/curious nature.
  3. I am a very positive optimistic person with an enquiring, curious mind, am very passionate, and care deeply. These traits are very helpful when it comes to coaching entrepreneurs.

In my view, ‘coaching’ of entrepreneurs/talent is much more productive, valuable, and enjoyable than attempting to manage them.

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My weaknesses include

  1. Taking on more risk than I should. In supporting the entrepreneurs and talent that I do, I expose myself, my family, and my financial backers to more risk than I should. I let emotions get in the way of making hard financial decisions. I get too close to the entrepreneurs that I back which leads to me exposing myself to very large risks.
  2. I am over-optimistic when it comes to predicting the future. This way of thinking also has the effect of me exposing myself, my family, and others to large financial and other risks.
  3. It’s possible I may have poor judgment when it comes to selecting entrepreneurs to support. This remains to be seen, but if it is the case, it is a fatal weakness.

I don’t like to manage or micro-manage others. I prefer to spend my time thinking about and developing new ideas and opportunities. If I am backing someone, I prefer to coach them and not manage them.

This is a weakness where I make a poor selection of an entrepreneur to support, who actually needs ‘managing’ in the traditional sense.

To conclude, I sometimes don’t realize my own limits or the limits of the entrepreneurs or teams that I support. This weakness has the effect of leading me down the path of trying to achieve too much at once / running before walking.

That’s it Paul — I really enjoyed reflecting on everything.

Final thoughts

Having re-read this interview that I conducted a few years ago I thought I’ll leave it up to you to share your comments below.

On that note I’ll leave you with some Startup successes that this Entrepreneur delivered in the last 5 years:

  • Grew an online retail business from €2.5m to €12m per annum
  • Set-up a service business that achieved €5m annual revenue within 7 years
  • Grew property portfolio from €1.5m investment to €10m market value

Plus many more projects.

Individuals are increasingly creating more value from their bedrooms than many large corporations that have been around for decades.

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