Venture Capital: The 5 Essential Fundraising Rules

Entrepreneurs are faced daily with so many unknowns, so much chaos and survival pressure.  Adding fundraising into the mix can often feel overwhelming. How do they keep their heads above this murky water and avoid the many obstacles that lurk below the surface? I’ve distilled out five rules that apply to all fundraising activities as a series of guiding principles.

1. Timing is everything.

Sharks can detect a drop of blood from a long way off. Investors can similarly detect fear from a distance and this can negatively impact their view on investing in your company. At worst they will walk away, at best they will command a much lower valuation and more onerous terms.

The worst time is when you have little capital left and a very high burn rate. It would be far better to close a fundraising round ahead of needing to increase your burn rate.

Similarly, putting your product out into an unprimed marketplace that ignores it or does not deliver the level of hockey stick growth you were wanting will send a negative signal to potential investors. It would be far better to raise capital so you can use it to generate the right level of publicity and interest in your product ahead of its release so that there is pent up demand for it.

2. Fundraising is not transactional.

Think of raising capital as a continuous process that starts when you launch your company and ends when you sell it.

Always be raising based on your continuum of growth needs. But never be raising at some juncture when it is critical that the funds come in or your business will falter, as per the point made above.

Also factor in that however long you thought it would take to close a round is probably only about half as long as it will actually take.

3. Funding marketplaces are cyclical.

Be aware that the climate for funding can shift markedly. At one moment there can be a funding frenzy with investors desperate to get into specific opportunity spaces. This will drive up valuations and give you a feeling that funding is easy, that you can demand better terms.

However, just as quickly the market will freeze over and it can become much harder to raise money either for a specific sector or overall.

Currently we are in the middle of a slowdown. The frenzy is over. Investors are taking their time doing due diligence and forming relationships before they ink deals. At this point you need more patience and to be more realistic on valuations than a few years ago.

4. Leverage funding inflection points.

Make sure you raise the right rounds of funding to match your position on the growth continuum.

And raise only enough to progress through the risk reduction you aim to achieve in that round. Too much funding may allow you to skirt through this risk reduction process and continue down a flawed pathway, building a delusional sinkhole that you cannot escape.

Continuously pare back on opportunities that present themselves to focus on core activities that progress you through each round’s inflection point.

Seed funding should be used to build a basic, but demonstrable validator for your hypotheses. Ideally this should be scalable – starting with a bare minimum validation but then progressively adding to it so that your product begins to approximate, but not reach product market fit. Remember to listen carefully to market feedback at this point and don’t power ahead into that delusional sinkhole when all the signs are there that your hypotheses are not being validated.

Series A funding is raised to get you to product market fit and the subsequent market traction that this enables. Investors prefer to come on board when they can see product market fit on the horizon as this allows them a more reasonable valuation than when customers are banging the door down to get to your product.

Series B funding is used to deliver scalable growth. You’ve built the rocket ship, you now need to scramble out of the growth engine room and into find the command console so you can steer your business into directionally correct territory that sets you up for the next round of funding.

Series C funding is perhaps the hardest round to raise as it is the real truth seeker. Up until now you could have relied on buzz to generate growth, but now you need to prove that you have the right unit economics in place to ensure sustained, profitable growth. This is a crucial time to be aware of that delusional sinkhole again. If you’ve raised too much money you could be plowing it into revenue growth and delaying the hard conversation you need to have around the economics of your unit growth. Revenue growth must convert into positive unit growth or you will sink your business as you expand it.

There are always exceptions, but raising outside of these inflection points is exponentially harder.

Coming back to the key point that timing is everything you should factor in about two years between each of these funding rounds. That gives you enough time to focus on growth for a full year before picking your head up for six months to raise the next round, while maintaining a six month contingency as a buffer.

5. Optimise your fundraising for success.

Does the investor or group of investors you are bringing into a round have what it takes to support you, over and above the capital infusion?

If you answer a resounding yes, then find an approximated win win deal and close the round. You could keep negotiating them down on deal terms or look elsewhere for a higher valuation, or a bigger named venture firm. But that would be a distraction. A financing deal is one moment in the growth continuum of your business. Keep your eyes on the prize: business success.

You are taking on a venture capital partner because you want to build a bigger business at an accelerated pace to what you could without their funding and guidance. Don’t over obsess about your equity stake. Think more about how much more you can grow your business with their involvement so that you all win, big. Keep that goal in mind and view each funding round as a mile-post on that journey. It is an important enabler, nothing more, nothing less.

By investor I refer to the sponsoring partner at a venture capital firm, not the firm itself. Your relationship with them is going to be a lifelong partnership, not a transactional, deal-based one-off interaction. Are you comfortable they would take your call at 3am in the morning or delay their Wednesday afternoon golf game to attend an emergency board meeting? Think of them as talent you are bringing onto your team. Talent you are prepared to take advice from and whose counsel you would trust implicitly.

I hope these rules assist you in your capital raising endeavors and provide you with much needed perspective to view funding as a part of your growth journey.


This post was initially sent as part of the EXOscalr BeFierce newsletter. If you want to receive it directly  you can subscribe here:

Growth.Reinvented: How Leading Companies Create a Concerted Front For Business Growth

As evidenced by numerous surveys, growth is the major enduring focus for business leaders. However, growth is tackled ad hoc across many organizations. Leading companies drive rapid, sustained growth through a concerted front strategy.

More and more companies have a leadership mandate to achieve growth, a vision of what growth needs to be and an understanding of a growth culture.

They embark on various growth initiatives, but these are mostly carried out in silos.

Leading organizations not only undertake numerous growth activities, but they also conduct them using a concerted front strategy.

They start by formulating a view across all their growth activities. They then translate that view into a business-wide operating system.

As their concerted activities mature this operating system shifts to being driven by a dedicated growth group that works across the business.

I’ve written a Growth Report that explores the concerted front strategy used by leading companies to achieve rapid and sustained growth.

The report starts by highlighting key aspects of the 10 facets for driving business growth, then considers what a dedicated growth group should consist of and what to look for when hiring the right people for it. It concludes with suggestions on how to create a 100 day growth dialogue.

You can download the full report from the EXOscalr website at the following LINK.

The EXOscalr Entrepreneurial Growth Program: How to convert chaos into growth

High growth scaling up is a function of converting random chaos into positive, directionally correct chaos. To do so you need to know where you are going and whether you are on track.
At EXOscalr we have devised the Plan Data Progress Operating System to help you transition seamlessly from startup to scaleup.
Find out more about this Operating System as well as other algorithms and methods for growth on the EXOscalr Entrepreneurial Growth Program. We have a limited number of spots available. Ping rand at exoscalr dot com if you are interested in being considered.

We Dare Not Fail Ourselves

Waiheke Winter Light

We live in a world surrounded by terror and unrest. The immediate agony of disease, displacement and starvation pervades. Technological advancements bring economic uncertainty to many disengaged workers.

70 years ago Sir John Gorton, who went on to be Prime Minister of Australia, spoke of a similar world. Surrounded by so much intolerance I believe his advice echoes across the ages. May he inspire all of us to be fiercer with ourselves, with our relationships and the world around us. May we never be complacent. May we be brave and not accept injustice, wherever and however we find it.

Hear his words and be watchful: –

“We cannot expect to make a new and better world as a result of the exercise of brute military force. We can only expect to achieve the kind of world we want by the use of brains and effort during peace.”

“We must raise the spiritual standard of living so that we may get a spirit of service to the community and so that we may live together without hate, even though we may differ on the best road to reach our objectives.”

Tomorrow we must carry on again. And the tasks which lie in front of us are immense and urgent as never before.”

“What can we do? Individually, it may not be much. But we can at least all think on the problems which are in front of us and be ready to act on our thoughts if the opportunity arises. We can try to reason out how we may best provide a full and satisfactory life for all our citizens. We can practise tolerance and understanding. And we can be ready always to defend against attacks, either from within or without, the political freedom, the measure of freed which we already have.”

 “It will be hard. It will mean a constant effort from all of us. Build a world in which meanness and poverty, tyranny and hate, have no existence.”

– Sir John Gorton, Mystic Park Hall, April 3rd 1946.


We dare not fail ourselves. We dare not see the chance to improve our world wasted.

Every single one of you reading this has the power to affect change. In fact, many of you have already demonstrated, in your unique ways, the power to lead massive change.

I implore you to step up, to break free from your daily busyness. Accept my challenge to make a commitment within 24 hours of reading this and join me on this quest.


This post was initially shared through the EXOscalr Be Fierce newsletter. You can subscribe at:

Formulating a Quick Digital Transformation Ratio Test

The quick ratio measures the ability of a company to pay its current liabilities when they become due only from quick assets, which for the purposes of this liquidity test are defined as assets that can quickly be converted into cash within 90 days. [Hey, I do remember something from time as a trainee accountant in 1983!]

In today’s climate of almost pervasive digital transformation initiatives I questioned in a recent post whether such activities were working. Could they be measured yet?

The argument against is that innovation and change takes time to percolate. Perhaps, but that is a cop out. There is the equivalent of the quick ratio that can be used to test if a transformation activity is on track. A digital transformation can have many moving parts, and depending on the size and scope of such an undertaking it can be difficult to pin down exactly what is its end game.

This is where the quick ratio comes in. Can you quickly, within the first 90 days of its commencement, poll senior executives in a company and come up with a common view, lingua franca and cohesive support front for a digital transformation initiative? If not, then the initial dissidence and inertial dampeners that emerge as a result of not singing from the same transformation hymn sheet will grow exponentially  during the course of the ensuing months. The resultant friction may well prevent such an initiative from achieving its desired result.

One of the sharpest analysts I’ve had the pleasure to work with, Gartner’s Mary Mesaglio, has posited a step by step Quick and Dirty Transformation Test for Executives.

EXOscalr Announces Support For Early Stage Entrepreneurs

At EXOscalr we want to support the next generation of entrepreneurs and are offering a limited number of slots for early stage entrepreneurs to work with us.

As part of our support, we will significantly reduce our rates for one on one coaching with entrepreneurs and will also work with peer groups made up of a maximum of 3 synergistic entrepreneurs.

To qualify your current business must be pre-Series A funding. You could be anywhere on the spectrum between exiting your current role to do a start up through to being close to raising your Series A venture capital round. Our logic is that Series A is enough of an inflection point for us to have a full business conversation that doesn’t necessarily require EXOscalr subsidising you by reducing our fees.

EXOscalr is a strategy, growth and wisdom coaching company. We help CEOs and their teams deal with the internal entrepreneurship rollercoaster, supporting the growth they need to exponentially improve their performance and their life.

Ping to find out more about the opportunity to work with us.

Digital Transformation and Innovation: Is It Working?



When I was at Gartner my colleagues and I advised many companies to focus on innovation and digital transformation as a core mechanism for achieving growth. It is fantastic to see so many companies in so many industry sectors seizing on this.

So why are business leaders still up at night?

What is your number one fear?

“Will it work?”

How do you know that all this change, this innovation and digital transformation activity, will deliver on your greatest business need  – growth. Without this change and growth, you fear your company will be in grave jeopardy.

Overcoming the Fear Panoply by Crossing the Threshold

This overarching fear keeping you up at night is an existential one, the fear of becoming obsolete.

One moment you are.

The next you are gone.

Perhaps remembered for doing some great things, but more likely forgotten as quickly as a shoreline sandcastle washed away on a relentless tide.

Perhaps an even worse fate awaits, that of being remembered for not having reacted to an obvious, changing situation. Forever known as the company that got blindsided before it could change.

This is the fear that is being exploited to drive you to take up the change mantle.

“Innovate or die”

Given that your company does not operate in isolation your fear of becoming obsolete is exacerbated by two competitively-driven, change-related fears. The overarching one is the fear of not growing. This is a foundational fear. Growth is seen as the marker for continued relevance, for being able to stave off obsolescence.

This logic drives the second of these fears, that of missing out. This fear is predicated upon the thinking that if your company continuously misses out on opportunities for growth it will accelerate the early onset of obsolescence.

The fear of not growing and of missing out have become key drivers for companies initiating digital transformation and innovation programs. But to do so they require sufficient change impetus in order to overcome the fear of making mistakes.

No company wants to waste its valuable resources or suffer the loss of face that results from failure. Failure, particularly continued or massive failure, can also lead to obsolescence.

The tension between tackling change and the fear of making mistakes has been reduced somewhat by the startup-inspired hypothesis that failure is not in and of itself so bad as it provides fuel for learning.

Be that as it may, in order for your company to successfully undertake digital transformation and innovation it must sufficiently cross the obsolescence threshold.

This threshold is crossed when your company’s fear of becoming obsolete is driven more by the fear of not growing and missing out than the opposing fear of making mistakes.

This is an important distinction as the nature of your company’s digital transformation and innovation initiatives is predicated on the velocity at which your organization crosses the obsolescence threshold.

Ultimately, the success of such initiatives will be determined by what type of digital transformation and innovation your company undertakes. Depending on the groundswell of industry change within which your company is encapsulated, these initiatives need to have more or less impetus to succeed.

Too little activity that matures too slowly produces lacklustre results. This is a level one transformation failure.

Too much activity that matures too fast leads to burn out. This is a level two transformation failure.

Both levels of failure can be fatal for your company and it is crucial to find the right transformation cadence.

Currently there is sufficient impetus in the fear of becoming obsolete and enough of a herd mentality in most industry sectors for many companies to be initiating a digital transformation and innovation program.

And this leads to the pivotal question. How do they know these programs will work?

Is there a commodifying effect at work? If everyone is innovating and has a lab in Silicon Valley what does this mean? Does it reduce the effect of such activities to a common baseline? Do you then need to be even more disruptive or more of a digital business? What do you change, what should stay the same?

Are there warning signals such a program is working or not working? What are the leading and lagging indicators? How can you spot these and course correct before it is too late?

How can we help?

The EXOscalr team brings 30 years of digital transformation and innovation wisdom to give you peace of mind.

We ruthlessly analyse your capabilities, we benchmark your activities against our success modelling and we give you discrete, honest advice on what is working and what isn’t.

We then double down and guide you to be fiercer with yourself, your people and in your activities so that you can eradicate this panoply of fears.

So Much Innovation, So Little Wisdom

Incubator, Schmincubator. Hackathon, Schmackathon.

Pause for a moment and consider how many incubators are operating in the world right now. How many hackathons are taking place?

The mind boggles – they used to be geographically dispersed, then they focused on industry sectors, now they have proliferated down to the micro-industry level.

Startups are graduating from not one, but multiple incubators and they have still not been able to find their mojo.

There are ‘professional’ hackathoners who win event after event, but never actually produce anything.

All this innovation. All this busyness. But how much real progress is a being made? Are people and companies learning from these activities. Can we truly say wisdom is on the increase as a result of innovation?

Pause for a longer moment, think about it – what have you done to increase worldly wisdom today?


What’s impossible when you unleash your absolute potential?

Last week’s 3000 km (1800 mile) drive across Australia may have only covered a relatively small part of this great southern land but it enabled me to do three important things:

1. spend precious family time in the South Australian wine regions;
2. take down time and fly my drone across amazingly stark terrain; and
3. contemplate the work I’m doing and hone my thinking.

All three of these activities are essential for my continued well-being and overall spiritual fitness. I arrived back in Sydney exhausted, but full of energy and motivated to continue with my overarching purpose – using my wisdom to guide leaders unleash their absolute potential.

During this journey I both refined my purpose and crystallized a framework that succinctly explains our approach to strategic leadership.

Absolute Potential

Recently, one of my clients beautifully described how I was guiding her to ‘unleash her potential’. This really resonated as an apt moniker for my work. On the trip I realized that adding one extra word made a world of difference.  That word is ‘absolute’ – my focus is on “unleashing your absolute potential“. By this I mean your unconstrained potential, free of self-imposed limitations and societal constructs.

As I move into the second year of running EXOscalr I aim to apply this insight to my work and ask clients a really big question, “What’s impossible when you unleash your absolute potential?” Imagine what is possible when you operate without constraint.

Strategic Leadership

On my journey I also formulated the EXOscalr Strategic Leadership Model, which you can see in the diagram below.



This provides the framework for the way in which we work with clients. It is designed in three core modules that connect to drive deep self-awareness, build your momentum and empower you to achieve your absolute potential.

As I say in the EXOscalr Overview (Dropbox link), this sounds straightforward and may even give you a sense of comfort. However, don’t be fooled – EXOscale results are not achieved by following a curriculum, nor are they beholden to a set, linear path.

“You are the program. Your words, your voice contain your powers and they come to life within the coaching space.”

Under the Strategic Leadership Model a lot of work goes into self-inquiry and developing a growth engine, but the final element required for achieving your absolute potential is to be fierce, to harness your personal superpowers and, by doing the work, making things happen. This is a true sine qua non and I have seen people flounder who have put in the initial groundwork, but have not been sufficiently fierce, have not been proactive and seized opportunities.

To be fierce is that essential magical element and I have renamed this missive, Be Fierce, as a reminder to all of us to constantly step up and challenge ourselves.

I encourage you to take a read of the EXOscalr Overview and reach back to me if you’d like to talk about coaching yourself. Feel free to also pass it on to colleagues, portfolio CEOs and friends who may be interested in removing their constraints, refining their capabilities and unleashing their absolute potential.

At EXOscalr we work with our clients to unleash their absolute potential and make a difference. We draw on decades of experience, including insights gained in venture capital, corporate innovation, building high growth organizations and advising the Fortune 1000 on transformation.

I read all my email at and I’m also at +1-650-529-4181 and +1-646-480-0205. Feel free to reach out.

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