Entrepreneurs, Executives, Influencers and Success: 3 Ways to Deal with the Dark Side

Loneliness and depression affect everyone in all walks of life. Successful people are more prone to it and this piece provides practical, tangible measures to minimize the impact of the dark side.

Mark Suster, a venture capitalist at Upfront Ventures, believes that success breeds loneliness. It can be a depressogen and in some studies the rate of depression in successful people is higher than 1 in 3.

Mark identifies four reasons success can be a lonely place:
1) the expectations don’t stop – they get higher
2) there is so much more at stake and so many more livelihoods and legacies that you plan for
3) it is only a heartbeat away from failure and the press love a rise and fall story
4) you find yourself surrounded by a bubble and often a bubble with vested interests in your actions.

This holds true for successful people in all walks of life, but I’d like to focus in on three groups:-
* entrepreneurs,
* fast-track executives, and
*social media influencers.

All three can get thrust into the spotlight of success with far more impetus than other groups and are therefore susceptible to the sudden onset of loneliness and depression, with no experience in how to identify or cope with it.

One moment Jim was a struggling entrepreneur. His mother kept yelling at him to get a real job. His friends told him that he was crazy. The next moment his company was valued at over a billion dollars and some guy he’d only ever previously seen on the cover of magazines was thrusting a very, very big check into his hands. He spent six months mastering golf and travelling the world. Deep down he began to feel more and more hollow inside. He was becoming detached from his former entrepreneurial self and didn’t know how to identify himself anymore.

Fast-track Executives
Greg was on the executive fast-track within a Fortune 500 company. There was a constant pressure of work on him. He was taking big jumps up the corporate ladder and the higher he got the lonelier he became. He eventually made it to CEO, but this was short-lived. He was replaced eighteen months later when the board decided to bunker down on what had worked in the past rather than exploring new opportunities. He was extremely disappointed and went into an irrevocable downward spiral.

Social Media Influencers
Helen shot to prominence when she attracted a huge following on her YouTube channel. She received a six figure sum just to place a popular motor vehicle in the background of one of her Instagram photos. However, the industry began to wear her down. While the going was good she did great, but as she started to stumble it became really tough for her.

What can you do to deal with the dark side?

1. Embark on quest-centered therapy

Before you start any form of therapy or very early on in your therapy sessions, figure out with your coach or psychotherapist, what you want to achieve, for example being at peace with yourself.

And then embark on a quest to achieve this goal, marking your journey towards peace with myriad small wins. As you progress you will get better at achieving results that progress you towards fulfilling your quest.

2. Explore the dark

Your life exists as a narrative, a story arc with a past, present and future. In order to truly achieve well-being you need to delve into parts of your past and present that you may feel much trepidation about. There may be dark times when your arc dipped low and this darkness cannot be avoided. It must be explored as it leads to the third point.

3. Tackle the triggers

Loneliness is often exacerbated by triggers. Things happen in your life that for most people would be viewed as slightly negative, but you view them as off-the-charts negative. Having explored the dark you become aware why these things have such an effect on you. You can identify very early on, even before the trigger starts having an accentuated impact on you, that it is there and you can act.

You can put in place methods you’ve worked out with your coach or therapist to combat the downward spiral into depression, you can blast away the negative thought processes and the self-sabotage well in advance of them taking control of you and launching you into a days-long relapse.


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Three Things Successful CEOs Do Exceptionally Well


Over the years I have taken on the CEO mantle a number of times, I have coached many others and  I’ve enjoyed being Chairman and working together with CEOs and their Boards.

From my experience there are three core activities that great CEOs have become expert at:

1. The ability to see the business and the macro environment from a 40,000 foot level;
2. While simultaneously listening empathetically to staff and customers (or users); and
3. Surrounding themselves with great people who they consistently empower to give of their best.

Creating this winning CEO algorithm in either a large corporation or a highly volatile startup atmosphere requires nerves of steel, a strong sense of self and belief in your ability to lead your team.


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Creating Contagion: 5 Rule to Delivering Brand Success


Here’s the rub…against a backdrop of thousands of new brands appearing daily, you decide to take your destiny into your own hands and create a new online brand. Your friends call you crazy, after all, how can you be heard above all the noise in the marketplace, how can you think anyone will become an evangelist for your brand.

Rest easy, there are 5 rules to creating contagion. Follow these rules and you will be well on your way to getting a strong following and building brand success.

RULE 1: Embrace Messy
The real world isn’t a clean, ordered place. So why should your brand be? Embrace the messy bits, do things when you have yet to perfect them, release alpha. Get out there, push the edges.

RULE 2: Release Control
Don’t think of your brand as a fragile newborn that you need to hold onto tightly and nurture closely without giving it any room to grow unchecked. Instead look at your brand as a sprightly teenager that needs a level of freedom to go into the wide world, explore new avenues and grow in ways you never imagined. Give up some control in your brand to your users, let them evangelise for you and you will be pleasantly surprised at the results.

RULE 3: Back Fires
OK, you’ve got your site up and have regular users. Some of them are innovating on your site, but you’d also like to do some really big things on the site. Wisdom says rather pour small amounts of gasoline on the fires your users have already started, than pumping gallons onto large logs that no-one has tested. The analogy is that a fire with a small amount of gasoline on it will be boosted, whereas a log with gallons of gasoline will simply be a …wet log.

RULE 4: Scare Yourself
Look for issues that would take you way out of your comfort zone and tackle them. If you go right to the edge and really scare yourself, it’s easy to then deal with the smaller issues closer in to your comfort zone. Continually challenge yourself.

RULE 5: Solve Small
Give your users small problems to solve. This gets them used to working with you on building your brand. Once you have established a pattern of problem solving you can ratchet up the size of the problems you open up to your users.

Build these rules into your daily mantra and go build your brand!


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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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