Raising Capital: How to Close the Deal with the Right Investors

At the latest CFO Recruit boardroom, ‘Financing Your Company: Understanding How to Close the Deal,’ Scott Griffiths gave attendees a rare look at fundraising from both sides of the negotiating table. Griffiths has built companies as a CFO and later ran a venture fund himself, and that background shaped a session that went far beyond the usual pitch deck advice.  

He walked the group through what investors actually think when a founder or CFO sits down across from them and why so many raises stall before they ever get close to a term sheet. 

“You’ve got two eyes, two ears and one mouth. Make sure you’re using them proportionally,”  

Griffiths told the group early on, a line that stuck with attendees for the rest of the session. 

Why Raising Capital Starts with Finding the Right Fit 

Griffiths opened with a point that trips up most founders anyway. Not every investor is the right investor, and the mismatch usually comes down to sector, geography and deal size. A healthcare investor will not fund an enterprise software company no matter how strong the numbers look, and a fund built for ten million dollar checks is not writing a two hundred thousand dollar one. 

He also pushed back on a common habit: Approaching every investor on a list at once. Griffiths recommends going after five names at a time, taking the feedback and fixing whatever did not land before moving to the next five. It protects a founder’s reputation, since word travels fast in this world. 

The Fund Economics Behind Every Investor Decision 

Griffiths spent real time on the economics behind a fund’s decision and this is where raising capital stops being about a good story and starts being about math. Venture funds run on a ten year cycle, most carry a two to two and a half percent annual management fee, and the target return that gets discussed in press releases rarely matches what funds actually deliver. He cited data putting realistic venture returns closer to thirteen to fourteen percent, well below the twenty four percent figure most funds chase. 

What Raising Capital Actually Costs You 

Before a founder signs anything, Griffiths said, they need to be honest about what they are willing to give up. Equity, board seats and control are the obvious ones, but he also flagged something founders rarely plan for: Investors often ask existing owners to reset their vesting schedule, even on stock they already earned. It is not a trust issue on the investor’s side; it is them making sure management stays committed to growing the capital they just put in. 

“To an investor, your company is purely a deal,”  

Griffiths said, reminding the room that founders who forget this tend to negotiate from a weaker position. 

What Investors Actually Check Before Writing a Check 

Griffiths broke down the diligence points founders should expect on the other side of the table, and it is worth treating this as a checklist before any first meeting. 

• Sector and stage fit: Does the fund actually invest at your stage or just claim to 

• Fund life cycle: Is the fund early in its cycle with capital to deploy or winding down 

• Syndicate history: Who else has this fund invested alongside and how did those deals perform 

• Ethics and reputation: How do they treat founders once the money is in, not just before 

• Active deployment: Are they still writing checks, since a quiet fund often means a closed one 

The session also covered timing, and Griffiths was blunt about it. Summer and the stretch between Thanksgiving and year end are the worst windows to start a raise. The best time is right after Labor Day or right after the new year, and founders should be building relationships with investors six to eighteen months before they actually need the money, not after. 

In Summary 

Raising capital, as Griffiths framed it, is less about the pitch and more about preparation, timing and picking the right five names before the right fifty. CFOs walked away with a clearer sense of how investors think, what they are quietly checking behind the scenes and how to avoid the mistakes that kill a deal long before it reaches a term sheet.