The most painful fundraise I ever did was my own
Fifteen years advising on raises, then the founder’s chair.
By the time I co-founded WeSwap, I had already spent close to fifteen years on the advisory side of fund raising, M&A and capital markets. I had advised on more IPOs than I can comfortably count (as reporting accountant, Nomad and Sponsor), sat across the table from countless founders, and quietly assumed I understood what raising money felt like.
I did not.
Advising someone through a raise and lying awake wondering whether you can make payroll are not the same beast. They are barely even the same species.
What the founder’s chair taught me was not a technique. It was a feeling, and it changed how I read every business I have worked in since.
When you have personally signed the documents and watched your own runway shorten day by day, week by week, you stop seeing a fundraise as a transaction with a close date. You start seeing it as the thing the whole business is quietly organised around, whether anyone admits it or not.
We nearly lost an anchor investor (a family office) on one round because the executive who was working it from their side took offence at the annual leave provisions we had in our employment contracts. It became a big emotional thing for me, and my heels were firmly dug in.
Until our lawyer said to me: “Simon, are you really going to throw this away over that? Are you even taking any holiday?”
I have since had the CFO seat through IPO, delisting, refinancing and turnaround. I can do the mechanics in my sleep, which is roughly what I was doing, given I executed one of those IPOs as CFO on a three-day-a-week contract, which everyone told me was mad.
Well, I did it, and we raised £18m.
But the thing founders actually seem to value is not the mechanics. It is that I have been the person with everything on the line, and I have not forgotten what that does to your judgement.
Most finance leaders have seen a capital event from one side. I have been unlucky enough, and lucky enough, to see it from all three: adviser, founder, and the C-suite.
I work as a fractional CFO for SaaS and technology businesses with a raise, a refinancing, a listing or an exit ahead. If that is where you are, I would be glad to talk.