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:

Are Entrepreneurs Suicidal?


The topic of depression in startup founders is becoming more prominent. It is an important discussion that was highlighted when outspoken serial entrepreneur Jason Calacanis was asked his views by a journalist.

He replied, “Running a startup is a mentally-challenging pursuit, with the chances of failure being absurdly high and the effort required being so extreme. Most of the people attracted to changing the world via a startup are highly-driven and quixotic, but sometimes they are manic.”

“I don’t think startups cause depression, but I do think depressed people can be lured into the chemical rush of running a startup without understanding how trying it really is.”

My personal view on the topic is that being prone to depression should not be a contra-indicator to becoming an entrepreneur.

Instead there are methods for dealing with depression, fostering resilience and reducing fear (of failure, of success) that while important for all entrepreneurs become imperative for those who need to fight their shadows more than others.

The most likely accelerator for depression is not being true to one self. Do a startup for the right reasons that resonate at your soul level, not because it is cool. Not being true to yourself creates emotional friction that will wear down your resilience and let the shadows in.

There is also a misunderstanding about what generates depression and people often oversimplify this very complex issue. It is not as simple as “just getting over it”.

This comment from a Reddit thread on the topic points to the complexity involved:

“The solution to depression is to be happier and stay positive, but doing that involves rehauling habits, improving one’s environment, setting goals, having the proper environment and support, and putting consistent work into changing the way one thinks, day after day without fail or else one runs the risk of undoing every step of progress. By the way, you have to do all of this while your mind tells you how pointless everything is and leeches away your capacity to feel pleasure or pride about a job well done, so any progress you do make provides no intrinsic motivation.”

Many entrepreneurs feel overwhelmed by the sheer number and weight of the decisions they face. Do I hire this person? Do I fire that person? Should I take funding from them, or them? Who is giving me the right advice? What are the consequences of releasing a new product feature – too early, or too late? Should I sell the business to them, at that price? And on and on.

These decisions can mean life or death for their business. Yet for people living with anxiety, every single decision, no matter how small they may seem to others, feels like they have life or death consequences. Factor anxiety into the mix for an entrepreneur and they become far more prone to depression and even suicide.

Another Reddit comment highlights how someone with anxiety thinks:

“It’s like a life or death game of chess. You have to think ten moves ahead and have a move for every situation in advance. The fear of death gets worse with every possible move you analyze. And if life makes a move that you didn’t see coming, instant breakdown, no matter how small insignificant the move was.”

Nor is depression a tap that can be turned on or off at will. It is with someone constantly as another poster to Reddit said:

“Every day of my life! Normal people don’t get it. They think you are acting crazy and irrational and treat you like you can just turn it on and off whenever you want, like it’s a choice. It’s not. I’ve learned to “deal” with it and suppress it a bit but it’s always there.”

Unfortunately there is a rise in suicide rates across all demographics, not only entrepreneurs. A 24% rise between 1999 and 2014 in the US has been attributed to concerns about jobs and personal finances. These issues can be exacerbated amongst entrepreneurs worried about how they keep supporting their staff and feeding their families.

It is important for entrepreneurs to realise that there is no direct causal link between being in the grip of fear and spiralling into depression. Realisation and resilience are key to staving off the shadows. Former Google and now CEO at Accompany, Amy Chang said in an interview recently, “I’ve made so many mistakes along the way. I have those ‘3am wake up and can’t go back to sleep moments’ all the time. It is good for people who are just starting their careers to know that too, so that when they are totally scared out of their minds of failure, or whatever else, they know it is 100% normal.”

My advice to entrepreneurs, be they new to the game or old hands, is tread the entrepreneurial path with eyes wide open. Do not be afraid to talk about your fears and anxieties and seek assistance if things get more serious.


This post was initially published as part of the EXOscalr BeFierce newsletter. You can subscribe here: .

A World Leading Entrepreneur Growth Program for Leaders

EXOscalr is proud to launch its world leading Entrepreneur Growth Program, which is designed to provide early to mid stage companies invaluable insights into achieving high growth.

The Program runs over 6 weeks and gives senior executives practical advice, algorithms and methodologies that will significantly boost the velocity of their growth.

Announcing the Program, EXOscalr CEO Rand Leeb-du Toit said, “Growth is the perennial focus for business leaders. Yet it is often misunderstood and mismanaged. The Entrepreneur Growth Program dispels the myths and delivers an unfair competitive advantage.”

“This advantage firstly delivers the impetus for growth through a suite of tools designed to achieve a growth boost and secondly, delivers methods for harnessing the ensuing chaos and ensuring it is directionally correct.”

The Program is available to companies globally and brings cutting edge insights from leading high growth organisations, in Silicon Valley and internationally, directly to entrepreneurs and business executives.

In addition, EXOscalr is releasing its 2016 Growth Report which highlights the 10 facets for driving business growth and how to create a concerted front strategy and business-wide operating system for achieving the levels of growth only seen by leading companies.

“Growth is not all lead generation and pitching. There is a much wider set of activities that must be undertaken by dedicated growth groups working across a business. Anything less is tantamount to stagnation in today’s dynamic business environment,” said Mr Leeb-du Toit.

The Growth Report explores what a dedicated growth group should consist of and also what to look for when hiring the right people for it.

The Report can be downloaded from the EXOscalr website and expressions of interest in the Entrepreneur Growth Program can be made directly to Mr Leeb-du Toit via email:

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.

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.

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?


A Fiercer Future: What Comes After A!? Let’s talk about chatbots and the Bot Engine



A few days ago I published the following piece on chatbots in my regular newsletter. I had no inside knowledge of what Facebook was planning, so I’m very excited to see real life imitating future gazing a lot quicker than I anticipated. At their F8 conference Facebook has announced they are commoditising chatbots with the release of the Bot Engine which relies on machine learning to create a variable conversation.

The last time I got this excited was when Facebook followed my lead at their F8 conference in 2007 and essentially kickstarted the app economy. Will this move on their part now help push us beyond basic AI? EXOscalr Labs is interested in talking to others who see the opportunity to build on this initiative. Be fierce, act now!

Here is the newsletter I sent out:


There is a major shift in focus from using apps for everything to interacting with virtual assistants. The issue though is that these AI-driven chatbots have zero personality and for the most part are purely functional. How can they be spruced-up and imbued with character, style and quirks? After all, if they are going to replace many of our day to day conversations we want them to sufficiently suspend reality so that we view them as more human-like than machine and so we derive some meaning beyond function from interacting with them.

Let’s use television as an analogy. At one point we watched whatever banal programming the television channels broadcast. But as this technology commoditised and we were freed up to choose what we watched a major shift took place. Quality content was in more demand. We moved over to pay TV and then Netflix, because they entertained us more with compelling content.

The same thing has happened in many areas of our lives – Spotify replaced radio, great novels replaced penny books.

I see a similar shift taking place in the area of virtual assistants. Would you rather chat with Siri or with a virtual assistant named Jerry who has all of Jerry Seinfeld’s character traits? Wouldn’t you prefer to be health-coached by your favorite athlete?

Australian company Complexica has developed Larry, the Digital Analyst, and he acts as a digital expert with the promise to improve topline growth, expand margins, build stronger customer relationships. But does Larry have character? Do customers actually want to interact with him or are they forced to?

There is an article in the Washington Post titled, The next hot job in Silicon Valley is for poets.  It talks about the growing demand for writers and other narrative-generating talent who can engineer a backstory for a virtual assistant.

As I see it, over the next 3-5 years the base virtual assistant + AI platform will commoditise to the point where it won’t matter which one you choose – IBM, Microsoft, Apple or an open source platform. What will matter more is how well you weave together a compelling story for your virtual assistants.

And this is where I see a new form of organization entering the market – a content developer rather than a technology developer. This organization will build a portfolio of compelling characters for its own functional arenas or license out these characters to companies.

This is an opportunity to skate to where the puck will be, not where it is.


At EXOscalr we work with our clients to grow their wisdom practice, 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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