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  • Writer's pictureGlyn Heath

The Investor Casino: How To Beat The House

We all know that in a casino the odds are stacked in favour of the house. We might get lucky one day but without luck there’s little we can do to affect the outcome. However, attracting investment isn’t gambling and there are lots of things we can control and many choices we are free to make.

There is neither a shortage of investors looking to invest nor businesses looking for investment. The challenge for both parties is finding the right match. In this article we’ll be looking at things from the perspective of the entrepreneur and how the dynamics of the investor-investee relationship can be shifted so that you can beat the house at the investor casino.

Beating the Odds at the Investor Casino
Beating the Odds at the Investor Casino

My observations are based largely on personal experience which I have then extrapolated into generalisations about various categories of investor. Clearly not all investors in all categories behave in the same way in every circumstance or are driven by the same motivations. I apologise up-front to any investor reading this who takes exception because they don't fit a particular mould and applaud you for not doing so. I should also point out that I have been both a major shareholder in several investee businesses and an investor in others.

Start Building Relationships Early

First things first; start seeking-out potential sources of finance well before you need it and begin cultivating those investor relationships. Identify your targets, whether they're specific people or organisations or pools of investor types such as angels, syndicates, venture capital, private equity, debt finance and banks. Within those broad categories there will be strata based on sector focus, deal size banding, minimum and maximum lending and so on. Select the ones that you will fit into at the point you require the investment. 

For a more detailed discussion on what to consider when looking for an investor that fits your business, what they’ll be looking for from you and some of the common mistakes that are made, see my article on Finding The Ideal Investor.

A Marriage of Equals Not a Toxic Relationship

In the same way sharks can detect blood from miles away and dogs can smell fear so investors can sense desperation. The initial mindset is that they have the money and you need it. From the outset they will automatically hold the power in the relationship and your scope for negotiating the best deal for you will be limited.

You mitigate this disadvantage by engaging well ahead of the time you need the investment. Appearing to be relaxed and in full control of your business will inspire confidence and make investors more inquisitive. Tell potential backers about your plans and how you are going to succeed along with how their investment would support future growth and help accelerate it. Keep them updated with progress as you reach milestones along the way in order to demonstrate that you are achieving what you said you would. Be confident and self-assured without sounding arrogant. Building credibility like this sets the scene and starts the process of bringing more equilibrium to the relationship right from the get-go.

The Tipping-Point

Your mission is to reach a position of strength ahead of any real negotiations starting. I call it the tipping-point, where an investor wants to invest in your business more than you need to take their money. You might want or even need investment, just not necessarily from them. Your ideal scenario is where you have multiple investors all wanting to back your business. The negotiating power will have moved in your direction enabling you to select the best terms and partner for your business.

Pick And Choose The Best Bits

In some cases the headline offer from one investor might look very similar to another. In other cases different investors will structure their offers in a variety of ways. Use this opportunity to carve out the best deal for you and your business which might be an amalgam of the most attractive aspects of multiple offers. Your optimum window to negotiate hard is on the way in before anything is signed-and-sealed, so you need to make it count. If you have multiple investors all expressing interest they’ll be looking for you to sign-up exclusivity with them. This is generally a good indicator of how serious the investor is but can be used as a tactic to neutralise a competitive investor. Don’t be in too much of a rush to go exclusive until you are clear that the overall shape and size of the deal is solid. In all likelihood you will be working with an investor over the course of several years and it is no use wishing you had pushed for a better deal six months after you’ve taken their money!

The best deal for you is not just the amount of capital for a given chunk of equity (or at the most favourable commercial rate in the case of debt). The devil is in the detail, as they say, and this is never truer than in investment agreements. Look beyond the high-level heads of terms to the finer detail in order to properly assess how good, or not, the deal really is. For example, do you benefit fully if you blitz your business plan or does the investor take a disproportionately large slice of the over-performance? On the flip-side, what happens if you fall behind targets significantly or circumstances beyond your control change the original investment plan drastically? Are they patient, will they support you through a tough phase?

The Nature of The Beast

During the course of building potential investor relationships it’s highly likely they’ll be your new best friends. Don’t be taken in; investors are interested solely in themselves and / or the company they represent. It is, after all, how they are remunerated. For VC’s and PE’s it’s imperative to show high returns in order to attract future funds. All investors / lenders primary objective is to make the highest possible return on their investment - if you also make money along the way it’s incidental to them. Yes, they recognise that keeping you motivated and appropriately compensated is important but not to the extent that it will impact their return. Of course there are exceptions, such as impact investors or those focussed on supporting social enterprises, but for the majority of investors, especially in the VC and PE world, your financial welfare is of little concern to them.

Investors Don’t Have An All-Seeing Eye

As much as many investors like to give the impression they are Masters of The Universe they are very rarely experts and will almost certainly know less about your industry than you. That’s not to say that their perspectives aren’t potentially useful; they often have access to market intelligence reports and an army of analysts that can be very valuable (and make them sound well informed). Ultimately, however, their investment decisions will be based on balancing their portfolio to factor in a blend of a handful of runaway successes, those that perform on-plan and the ability to accommodate some under-performers.

If your business falls within their investment criteria and risk profile, they’ll be buying into you and your team. They will ask lots of questions of you during the relationship building phase (and even more questions than you could ever imagine possible during the due diligence phase!) You should reciprocate. Ask them what they know about your sector and how their input will create value, speak to other portfolio companies about their relationship with the investor, especially post-investment, ask about successful current and past investments and don’t forget to ask about their failed investments (you might find you’ll get a frosty response or a bunch of excuses on that latter question!).


Here are some takeaways for stacking the odds in your favour when raising investment:

  • Start building relationships before you need the money

  • Focus on cultivating an investor relationship that is symmetrical and in equilibrium

  • Be clear about your objective: get to the tipping-point before negotiations begin

  • Build negotiating strength so that you can get the best deal for you and your business

  • Understand what motivates investors and play to that

  • Recognise where an investor is genuinely strong and can enhance value creation

Image attribution: Free Stock photos by Vecteezy

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