Should You Become an Angel or Venture Capitalist? Transitioning from Operational Executive to Portfolio Player


Leading executives can become totally focused on their operational role. Yet at some point, a trigger results in them losing their mojo for working in one business. What type of role is better suited to their next phase in life?

I posit that it is a meaningful transition for them to coach entrepreneurs and manage a portfolio of startup investments.

I’d like to illustrate my hypothesis by exploring two case studies.

Finding His Creative Mojo: From Ad Agency to Angel

David is a successful CEO of a world leading advertising agency. He has been focused for the last 12 years on growing the business, its reputation and its people. When he first approached me he felt that something wasn’t quite right. he had used an executive coach for many years, so understood the paradigm. Yet he realized that he needed to work more with a transformational coach. A coach who not only understood the business landscape, but also had firsthand knowledge and understanding of and empathy with people going through a transformational journey.

He loved to sing in the shower, especially on mornings before a big pitch, or when he was traveling on business. But he found himself no longer singing. This was the initial signpost for him to realize that it was time for him to go on a different journey. Many people ignore these early warning signals until it’s too late for them to change.

We spent our initial time together exploring what had excited him before. We delved into what areas he most feared. We explored if there were deep, unresolved issues that could stand in the way of him making a transformational shift. It is always best to work through such issues in the early phases of a transformation. They may cause blockages in your ability to perform. They could also act as blinkers to you discovering what you find purposeful.

We started the process of getting him to hear his inner voice. It had been suppressed for many years by his ego. This voice is always there in every one of us. We may suppress it to the point were it is so faint that we cannot hear it. What we were looking for from his inner voice was a deeper understanding of what resonated for David. What was his true soul work? In his 20s, he had worked with some start up companies on their market positioning. He had also been active in creating a technology spin out from his advertising agency.

He came to the realization that it was time for him to move on from running the operational, day-to-day side of his agency. It was time for him to get back into the world of creating. At his core he was a creative, which is why he had been so successful in the advertising arena. In particular, though, it was time for David to move deeper into the world of startups. Meaning and purpose for him was about building companies that were making a difference in the world.

This was never going to be a binary process, with him being an operational executive one day and a startup portfolio player the next. We had set that expectation early on. He knew it was a significant journey. It would have many moments: some positive, some negative.

A thought leadership position can benefit the move from operational CEO to Non Executive Chairman. David had no interest in writing books, but was keen to do outreach activities. He joined the board of a not-for-profit organization in the medical health arena. He was invited to be be a regular on a well-known, news-related television show. This significantly raised his profile. He took two further board seats of large companies. This positioning helped him make the mindset shift from single focus to portfolio player. It also ensured the right circles noticed when he made the announcement of his transition to Chairman and startups.

The next transition activity was a robust succession plan within the advertising agency. He identified two executives who had the skill set, drive and passion to step up into joint CEO roles. They were both positive about taking over the operational aspects of the agency. They began working with executive coaches to assist them in this process. David also began the discussion with his Chairman about his decision. They mapped out a plan for him to transition into the role of Non Executive Chairman within 24 months. The Chairman volunteered to take a less active board role.

We then began exploring the role that David should play within the start up space. He didn’t want to take on a CEO or other operational role in any one company. Instead he wanted to build a portfolio, working closely with startup CEOs as a coach. He wanted to ask the hard questions. He wanted to accelerate their growth and keep them on track as they scaled up. He preference was to invest into these companies, rather than consult to them. Their upside would be his upside.

He was comfortable working as an independent agent, as a lone wolf. Although he could see the benefit of teaming up with other investors when it made sense. He was suited to becoming an angel investor. He had significant net wealth at that point. His financial investment portfolio was diversified and included properties and blue-chip stocks. He could afford to allocate a few million dollars towards his initial startup portfolio. He was also of the mind that this was risk capital. He wanted to deploy his capital into companies taking bigger risks that had above average goals. He was mentally prepared for the fact that he may not receive a positive return on investment from this activity. It was to be a learning experience.

We worked closely on how to place him within the entrepreneurial ecosystem. He began to get a feel for how he could determine whether a startup was worth looking at closer. He crystallized his Investment Charter. This set out his strategy for the kinds of companies, types of technologies, geographical preferences, stages of development and many other factors that assisted him make investment decisions. The aim was to ensure he was targeting the right kinds of businesses that could deliver him significant return on investment.

As he started doing meetings and due diligence on potential investee companies, we continued with his education in this area. The aim was to make sure that he was not making emotional investment decisions. It was also to ensure that he was able to draw on his significant business experience. He became comfortable that he could add significant value to the companies that he chose to invest in. He wasn’t keen to join a formal angel group. Nor did he want to become part of the herd that chased investments at pitch competitions.

Some of the companies that he was targeting already had angels circling them. In some cases he had a meeting of the minds with these investors. This was one way he was able to start growing a network of angels he was comfortable to invest with. He also reached out to senior executives were either already active, or wanted to get active, as angel investors. Within a matter of months he had four different informal networks that he was teaming up with.

David went on a three year journey from operational CEO to having a portfolio of board seats and angel investments. He has not only found his inner voice but is also singing in the shower again.

Adventure Capital: A Venture Guy’s Journey

Tom was the CEO of a large communications service provider. He had been in this role for six years, having worked his way there from inside the organization.

Similar to David, he reached a point where he no longer saw colors. Tom’s world became black and white. He approached me with the realization that he needed to make some significant changes in his life. He had worked with an executive coach for a number of years and so understood the power of coaching.

He wanted to explore how best he could get excitement back into his life. He had also become enamored with the entrepreneurial fervor that was sweeping the world. He initially sat on the investment committee of his company’s corporate venture capital group. He found that he enjoyed spending time with their investee companies.

His company had already created a succession plan and there was no need for us to revisit that. He was also well known in the business arena. He had a high profile thought leadership position that we could leverage. We could move forward at a fast pace.

Tom decided to make a clean break from his company. We explored the best positioning for him within the entrepreneurial ecosystem. He didn’t want to operate as a lone wolf. He was more comfortable being part of a formal group that had significant track record and a brand name. He preferred to work with a group of partners from whom he could learn the ropes.

Through his corporate venture capital exposure he realized that he didn’t want to work with very early stage companies. He found this time in a company’s development frustrating. He was well suited to work with companies that had already reached product market fit and were experiencing rocket ship growth. For example, startup companies that were about to receive a significant Series A investment.

It became evident that the best place for him to play would be as a partner in a venture capital firm. He had discussions with venture firms that his company had done deals with. He got on well with some partners of these firms. He started receiving offers from VC firms. He chose to join a well-known firm. They were raising a new fund. This meant he could both participate as a limited partner in the fund and as one of the general partners deploying the capital they raised.

I continue to coach him in his position as a VC. There are many VC nuances he is finding a deeper understanding of – for example,

* the healthy tension between being an individual VC and a partner within a partnership;

* the potential for conflict between a venture guy and their investment companies.

* how best to coach portfolio CEOs – what kinds of questions he should be asking, what signs he should be looking for that they are on target and on track both operationally and emotionally.

Both David and Tom have not only stepped up through their transformations. They have also proven the power of having a virtuous circle by referring some of their portfolio CEOs to me and some of their former colleagues have also expressed interest in coaching.


1. Be aware of trigger signs that a transition is imminent. You may miss the signs and find yourself in a trough – it is significantly harder to catalyse a transformation the deeper you fall into a trough. Heeding the signs earlier is better. This ensures there is no urgency to your transformation journey.

2. Be prepared for significant change. Transformation is never linear and this organic journey may take you places you didn’t initially imagine. Go with that flow.

3. Be prepared to listen to your inner voice. You may have a tussle with your ego not wanting to let go. Eventually your inner voice will win out.

4. The world of startups is not for everyone. Nor is being an entrepreneurial investor. Go there for the right reasons – it resonates deeply with you, you enjoy creativity, you have the right risk appetite and profile. Don’t go there because you’ve read in a business or in-flight magazine how hot startups are or how much money you could make in the space.

5. Don’t burn bridges. Once you’ve made your mind up to transition, do so gracefully. Ensure the right succession plan is in place. Leverage your current position to create your thought leadership position. This will ensure you optimize your transformation trajectory. You already have a solid network in place, they want to help.

[Note: Names and situations have been altered for confidentiality reasons]


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Quests Can Be Massively Transformative. Here’s How To Choose Yours


“When your desire is not clear nor strong, it cannot take shape. Besides, if your desires are personal, for your own enjoyment, the energy you give them is necessarily limited; it cannot be more than what you have. When you desire the common good, the whole world desires with you. Make humanity’s desire your own and work for it. There you cannot fail.”                         Nisargadatta Maharaj

This quote points to the power of having a quest that is bigger than yourself.

Taking on a quest is a transformative trigger. By doing so you are giving yourself permission to change. Here we look more closely at the nature of quest.

What defines a quest?

It is classically understood to be a journey towards a goal. It is the act of seeking or pursuing something important. In many cultures it is viewed as a long and difficult effort to find or do something.

In contrast to simply living day to day, focusing on a quest changes your perspective: it’s bigger, it’s harder, it’s longer, but doing it packs a punch. In fact, the essence of a quest is change. If a quest doesn’t leave you changed, it’s more a hobby than a quest.

8 common quest characteristics

* What are you ready to own?
A quest is an act. It requires you to step up and own it. You take on the responsibility of doing your utmost to complete the quest.

* What do you already know you have to do?
Determining what quest to embark on may at first seem daunting. Until you realise that it can be influenced by injustices, by inequalities or by the hand fate deals you. In many respects a quest is presented to you, not selected by you.

* What is the difference you can make for others?
A quest is bigger than you. A quest is not about you. It is not about gaining recognition or status. If it doesn’t benefit others, be they a community, a company, a country or even the entire world, then it isn’t a quest. As such a quest benefits the many, even though some or all may never become aware of what was done for them.

* What intention can you crystallize?
A quest can be long, challenging and anything but linear. At any stage you can get sidetracked or lost. It’s imperative that you crystallize out a compelling intention that you can hold onto in order to reinforce your thinking and ensure you stay the distance and complete the quest.

* How can you attract others to your quest team?
the quest does not have to be undertaken alone. Remember that pride has nothing to do with it. At different times on your quest journey you may need different kinds of support. Determine how you can attract the best team around you to help you complete the quest.

* What is your next step?
A quest requires momentum and movement. A quest is completed one step at a time. It cannot be done by not taking action and you need to constantly be putting one foot in front of the other, constantly thinking about the next step.

* Are you ready to take a leap of faith?
Questing is not for the fainthearted. You will be required to take many and myriad leaps of faith on your quest journey. There will be times when you doubt yourself. There will be moments of second-guessing. Fear may be your constant companion. You may want to turn back or find an easier way, but you can overcome these tests on your resolve.

* Are you ready to brave the elements?
Embarking on a quest is filled with uncertainty. As much as you plan, the outcome of a quest can never be known in advance. A quest is an organic journey of exploration. You need to build an understanding deep within you that you are comfortable with whatever happens. Your normal constraints and constructs will get in the way and try to hold you back from making the choices and taking the action that the quest demands of you. You will need to be willing to stride into the center of the field and stand exposed, braving the elements and embracing change.

Come Alive

The EXOscalr Come Alive Program is a 12-month, quest-based coaching program designed to trigger and support clients on their quest journey.



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A Unique Opportunity to Experience the EXOscalr Coaching Philosophy

How do you know if transformational coaching is for you? No amount of marketing material can help you make up your mind. It is an intensely personal choice, both for you as client and for your potential coach. There needs to be a meeting of the minds for both of you. The only way to really gauge compatibility is to do a coaching session.

In this spirit, the philosophy we are taking at EXOscalr is to invite interested people to join us for a one on one coaching session. Our premise is that, even if you do not become a member of our Masters Circle we will make a difference in your life and that makes it worth doing.

Visit our page to get more information and click on the call to action if you want to avail yourself of this opportunity.



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How to Design Your Life to be Frictionless


No one wants friction in their life. We all want to reduce it. We praise people who choose better business or life partners. We admire people who restrict time wastage and mindfully reduce friction. Yet, somehow, friction manages to sneak into our lives. How do we achieve the life design goal of a frictionless life?

Frictionless design evokes the intuitiveness of the Apple mantra: “it just works.” According to Andreessen Horowitz partner Steven Sinofsky it is about “reducing the energy required by an experience.”

Consider also that frictionless design fits into flow theory. When you reach the point of flow in an activity it becomes frictionless, it just works for you.

Frictionless does not mean simple or minimal. A complicated process may be smooth in its operation. One of life’s greatest joys is losing yourself in the narrative of a good book. Getting the latest novel from your favourite writer used to be a painful experience. You saw the review in the New York Times and then had to wait for your local bookshop to stock the book some months later.

Today you take for granted the process of reading an Amazon-purchased digital book on one of your devices. There is a lot of complexity in the model of delivering a book to your device. Yet it is almost instantaneous. Once you’ve purchased it, you can lose yourself in its pages at any time by opening the Kindle app. The book will synche to the latest page you were on across all your devices.

Think about your life. What barriers and constraints can you deal with and remove to make your life run more smoothly?

Look for activities that frustrate you, that induce rage or that are unnecessarily complex.

There are three friction-prone areas in which to start. These are areas where you can achieve easy wins:

1. Travel
How much travel do you do a year? Do you make the decision to travel lightly? Do you consider alternative ways of connecting and engaging?

One of colleagues is in high demand not only for his work coaching clients one on one, but also as a speaker at various corporate events around the world. He loves giving talks and meeting face to face with his clients, but cannot stand being on the road too often. It cuts deeply into his contemplative time. He could be writing another bestseller that will impact the lives of thousands. Instead he is standing in line at Heathrow Airport security.

I’ve suggested to him that he reduce friction by limiting his travel. This does not mean less client interaction. It means designing his method of interaction around a medium that is better suited to smoothing out his day. Connecting with clients via videoconference can be just as effective as meeting with them face to face.

2. Direct Reports
How many direct reports do you have? I once worked with a CEO who had 12. This is far too many. It is not only too much of a burden on you, but it is also unfair on your team as they each have minimal access to you.

You should have a small team of trusted lieutenants and provide as much autonomy to your broader team as possible. Hire great people and empower them.

3. Meetings
Does your organization run on meeting fuel? Do people need to meet in order for a decision to be made? How many regular meetings do you run, or attend? Do you require an agenda for every meeting? Does the term “meeting” mean a specific algorithm to your people, for example, must a meeting always be an hour (or more) in length? What percentage of your meetings are face to face versus via videoconference?

Creating a Frictionless Design Playbook

I recommend you consider implementing the following 8-step process over the course of a year. Work with your coach to refine this playbook and then discuss your progress in your regular coaching session.

The results will not only please you, but surprise you with how much more productive you become.

1. Categorize and chart your activities;
2. Score your various interactions daily, from 1 to 10 according to how much friction you feel;
3. After a month you should have enough data to determine which are your high friction interactions;
4. Plan out how you can reduce those frictions;
5. Introduce frictionless behaviour modification into your life. Focus on changing your behavior so you reduce the frictions;
6. Chart your interactions for the next 2 months. Pause monthly to review your progress;
7. Rinse and repeat this process over the next 3 quarters;
8. Conduct an annual review of your friction count.


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Does Your Business Have the Capabilities for Achieving Exponential Growth?

As CEOs and Boards you are faced with an unprecedented level of pressure to achieve growth. Your company needs to stay ahead of increasingly aggressive competition, from other companies in your industry, from outside your industry and even from scrappy startups who define their own playbook.

Growth is not a lever you turn on or off at will. It requires focus, it requires a set of core capabilities that work together as a well-honed scalable operating system. Does your company have such an operating system in place? To achieve the nirvana of hyper-growth, this operating system needs to be working at peak performance capacity. How close is your business to operating at optimal capacity?


We’ve designed a set of questions that help you uncover whether your business has scale in its DNA, whether it will be constrained by limitations and frictions and whether it has the capability to easily add fuel into its mix.

You can access the quiz via or directly here.


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Finding Your Soul Work: A Journey from Near Death to Nirvana

EXO1Rewind back to early 2014 and I was enjoying working for the world’s leading research and advisory firm as an executive leadership and innovation analyst. I spent my days flying around the world advising Fortune 500 Boards, CEOs and CxOs on growth, leadership and disruptive innovation.

On a Sunday night, mid-February, I’d prepped for an international flight in the morning and then…I dropped dead from a sudden cardiac arrest. I was able to revive myself, but was in a state of conscious ventricular tachycardia, a severely life threatening condition in which the heart beats at an extremely rapid rate.  I was rushed to hospital and spent several weeks undergoing a number of surgeries and also had a mini stroke, which was terrifying. I’ve detailed my health journey over this time (here and here), but in summary after an initially positive response my health deteriorated from mid 2014 leading to a further operation in December. Since then my health has improved dramatically.

Coming out of hospital for the first time in March 2014, I felt extremely grateful for being alive, for breathing fresh air and I saw the world through fresh eyes. I felt at the time that I had to make use of this opportunity to do something world changing. How could resuming the status quo be sufficient?

As Joseph Campbell puts it, “Only birth can conquer death – the birth, not of the old thing again, but of something new.

But what was it that I would do that was new? As the months passed, I spoke with many people, considered diving into a few opportunities and also went back to my work as an analyst. I realized that I’d been given a very rare second chance at life and to honour that I needed to do more than what I had been doing. I also realised that what I did had to resonate within me, deeply.

Steve Jobs explains this so eloquently, “Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

Even though I had some very trying times over the course of 2014, I was enthused by the journey I’d embarked on to search for my soul work, my calling. I came to realise that during my time as a VC and previously as a coach, I found most joy in helping great people transform themselves into being extraordinarily great – asking the right questions, guiding them to make the right decisions and acting as a trusted advisor. In this regard the role of a VC and a coach are very similar. As Roelof Botha of Sequoia Capital points out, the role of a VC is to help entrepreneurs navigate and solve problems on their own, to provide perspective and ask the right questions, and to provide frameworks for decision-making.

And so I’m super excited to announce that I’ve left my high flying analyst role and set up EXOscalr, the elite performance and transformational coaching and advisory firm. Our moonshot is to help create $1 trillion in value over the next ten years while also positively impacting 2 billion people. To achieve this goal we are working with entrepreneurs and leaders who have the capability to build exponentially scalable or exoscale companies, leaders who we can guide through a transformation into elite performers.

I invite you to join me on this journey.


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