Never Raise Without Putting Your Own Money In
Commit a substantial slice of your own net worth before you syndicate a deal — it settles the ethics and enforces the discipline.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 6
- Confidence
- 80%
Girdley states the rule plainly: he hates raising money for anything unless he is putting his own money in, so he commits a substantial amount of his net worth to new ventures before going out to syndicate. His stated reason is visceral rather than analytical — doing it the other way feels 'yucky' — but he identifies a second-order benefit that turns it into a genuine framework. Because real personal money is at stake in each deal, the rule stops him doing too many things: he has to really believe in something before he'll commit. The numbers are not token. He describes funding new businesses with a couple of million at the low end and $50-100 million at the high end, and personally guaranteeing the debt on Dura's first deal. The rule extends into how he structures partnerships. His strongest preference is a co-founder who also puts money in and makes the venture their job, which he calls the absolute best skin-in-the-game outcome. He is candid that he typically puts in more money than the other partners, and offers strategy, insight, best practices and connections rather than operating labour — while explicitly not wanting the operator's job. Girdley also claims a 100% success rate on partnerships, which he describes as one of his superpowers.
Origin
Asked whether he raises a fund or uses his own money, Girdley described syndicating deal by deal and named the personal rule that governs when he is willing to ask anyone else for capital.
Core principles
- 01Put your own money in before you ask for anyone else's.
- 02Personal capital is the natural brake on overcommitment.
- 03The best partner is a co-founder who also writes a cheque and makes it their job.
- 04Put in more than your partners if you're the one convening the deal.
- 05Offer strategy, insight and connections — not the operator's job.
- 06Syndicate deal by deal rather than raising a blind pool.
How to run it
- 1
Commit your own capital first
Girdley puts a substantial amount of his net worth into new ventures before approaching anyone else. The sequence is the point.
- 2
Size it so it constrains you
New businesses range from a couple of million to $50-100 million. The amount has to be large enough that it stops you doing too many things.
- 3
Take the personal guarantee where needed
On Dura's first deal the partners used debt and Girdley personally guaranteed it — exposure beyond the equity cheque.
- 4
Then syndicate the deal
With his own money committed, he syndicates deal by deal with other people rather than raising a blind pool up front.
- 5
Structure the partner for maximum skin in the game
The best outcome is a co-founder who invests their own money and makes the venture their full-time job — Paul at Dura is his model.
- 6
Define your side of the exchange
Strategy, insights, best practices, connections and a board seat. Girdley is explicit that he doesn't want the operator's job and wouldn't be good at it.
In the wild
Girdley and his partner — the former head of support at Rackspace — put up their own money for the first acquisition and only raised outside capital after running out at a couple of million. Girdley personally guaranteed the debt on the first deal and put in more than the other partners.
→ His partner became CEO, and Girdley cites him as the model co-founder — money in, job on the line, complementary skills.
Two associates from Girdley's entrepreneur-in-training programme, Hayden and Franco, built hirewithnear.com. Girdley put up the money and guided them; they did all the work.
→ He calls it 'the apex of Girdley automation' — a substantial cap table position in a business started with essentially no work from him.
Common mistakes
Raising on someone else's risk alone
Girdley's plain reason: it feels yucky. Beyond the ethics, a backer reasonably reads the absence of your own capital as an absence of conviction.
Committing an amount that doesn't constrain you
A token personal cheque satisfies the letter of the rule and loses its real function, which is forcing you to only do things you really believe in.
Taking equity while wanting the operator's job
Girdley is explicit that he doesn't want his partners' jobs. Convening a deal and then competing with your operator for control destroys the exchange.
Is it for you?
Best for
Operators syndicating acquisitions or new ventures who will be asking friends and peers for capital repeatedly.
Not ideal for
Founders without meaningful personal capital, for whom the rule would simply block every deal.
From the transcript
“what i've learned and that i only do is i hate raising money for stuff unless i'm putting my own money in it so i'll…”
“skin in the game matters then that also helps me not to try to do too many things like i could just be like okay…”
“the absolute best way of that is if they're a co-founder and they put money in it like me and then they make that their…”
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