The market for capital raising advisory is not well regulated, not well understood by most founders, and not short of people willing to take a retainer in exchange for introductions that may or may not lead anywhere. That is not a cynical observation — it is a practical one. The range of capability, integrity, and genuine market access among people who describe themselves as capital raising advisors is enormous, and the consequences of choosing badly fall entirely on the founder.
Having spent years on both sides of this equation — raising capital directly and advising founders on how to approach it — I have a clear view of what separates advisors worth engaging from those who are not. It comes down to a handful of questions. If you are considering engaging an advisor for a capital raise, these are the ones worth asking before you sign anything.
Have you raised capital for businesses like mine before?
This is the most important question, and the answer requires specificity. Not "have you raised capital" — but have you raised capital for businesses at your stage, in your sector, from the type of investors you need to reach. A track record in raising growth equity for technology businesses tells you very little about an advisor's ability to raise early-stage capital for an alternative asset operator. The skills and networks required are different.
A credible advisor will be able to name deals — not necessarily publicly, but in a verifiable way. They will be able to describe the investor type, the deal structure, the approximate size, and the timeline. If the answer to this question is vague, or the examples are all from sectors and stages different from yours, treat that as meaningful information.
Who specifically will you introduce me to?
Many advisors sell access to a network. Far fewer can articulate that network with specificity. There is a significant difference between an advisor who says "I have strong relationships with family offices across Australia and Southeast Asia" and one who can name three specific allocators they have closed with in the past 18 months, describe their investment preferences, and explain why your business is likely to be relevant to them.
"Network is only valuable if it is current, specific, and reciprocal. An old contact list is not a network — it is a history."
Push for specificity here. You do not need names at the introductory conversation stage — but you do need evidence that the network is real, current, and relevant to your raise. If the advisor cannot or will not give you that evidence, the network may not be what it is presented as.
What does your fee structure look like — and what does it align you to?
Fee structures in capital raising advisory vary widely, and the structure matters as much as the amount. A large upfront retainer with a modest success fee creates different incentives than a modest retainer with a substantial success fee. The former incentivises the advisor to take on as many clients as possible; the latter incentivises them to close.
Geoffrey Woodcock's view is that the best advisory relationships have meaningful skin in the game on both sides. The founder should pay enough in retainer to signal seriousness and cover genuine advisory work. The advisor should have enough at stake in the success fee to be genuinely motivated to close. Structures that are all retainer and no success fee, or all success fee and no retainer, tend to create misaligned incentives in predictable ways.
Ask the advisor to walk you through how they are compensated, and then think carefully about what behaviour that compensation structure rewards.
What will you actually do — week to week?
This question surfaces a lot about how an advisor actually works. Good advisors have a clear, structured process — they can describe what the first 30 days look like, how they prepare materials, how they manage the pipeline, how they handle follow-up, and how they keep the founder informed. They think in process terms because they know that a raise without a managed process is a raise that depends on luck.
Advisors who are vague about their process — who describe their value in terms of relationships and judgment rather than activities and milestones — are often telling you, without meaning to, that the engagement will be reactive rather than proactive. That is a significant risk in a capital raise, where momentum is everything.
What are the most likely reasons this raise fails?
This is the question most founders don't think to ask, and it is the most revealing. A good advisor will answer it directly and specifically — they will identify the genuine risks in your business, your documentation, your market positioning, or your timing that could cause the raise to stall. They will have a view on how to mitigate those risks before the process begins.
An advisor who struggles with this question, or who reassures you that the raise is straightforward, is either not thinking carefully about your situation or is telling you what you want to hear. Neither is what you need from someone you are about to trust with one of the most consequential processes in your business's life.
The right advisor is not the one who makes the raise sound easy. It is the one who understands exactly why it is hard — and has a credible plan for doing it anyway.
This article is intended for general informational purposes only and does not constitute financial advice.