How Nate Spiteri did it: I Spoke to 1,000 Investors Before Raising. Here's What Nobody Tells You
Nate Spiteri and his co-founder Drew met at the Antler residency, an accelerator program Antler runs across Australia. Drew was super technical — an ex-CTO at an energy startup with a master's in AI — and Nate was super commercial and marketing focused. They aligned on an impact focus and set out to build a marketplace to challenge Depop, eBay and Etsy, because Australia has a huge textile waste problem and people hoard clothing.
After speaking to hundreds of buyers and sellers, the insight flipped their idea: buying wasn't the problem, selling was. So they doubled down on the seller proposition and built Shopfront — a set of tools that sit between anyone selling fashion products and the marketplaces like Grailed, Depop, Etsy, Facebook Marketplace and eBay. The first product lists your products across every marketplace at once and pulls them down when one sells, using AI for image recognition and background removal to take listing from 15 or 20 minutes down to 1 or 2 minutes.
The hard part was money. Nate had just come back from four years in London, so his network in Australia was super thin when it came to people who would invest. It took a long time to find the ideal investor profile, and to get there he reached out to almost 1000 investors across the whole spectrum — dealing with 99, 95% no's along the way. He treated it like a sales pipeline: find your ICP, find the first yes, figure out what a yes investor looks like, then double down. The raise took about five months to close.
Everyone told Nate he was never going to close a round in December — that if you haven't raised by November you might as well cut the round and reengage in January. He thought that was a bit of a load of crap. He carried on, closed 800 K, and got engaged in the middle of pitching in September along the way. His take on the round: the first investor doesn't make the rest easy — it almost doubles the pressure, because now you can't disappoint the people already in.
What you'll hear
- The marketplace that became a seller tool — why buying wasn't the problem, selling was, and how that flip birthed Shopfront
- Almost 1000 investors — treating a pre-seed raise like a sales pipeline when you have a target of 750 and 99, 95% no's
- Closing in December — why Nate ignored everyone who said a round can't close before year-end
- The first-yes paradox — why getting your first investor almost doubles your pressure instead of relieving it
- Keep the CTO out of pitches — why hundreds of pitch hours should go to product, not the technical co-founder
- Why all the no's stay on the cap table updates — keeping every investor who passed engaged for the next round
- The bottlenecks in second-hand fashion — logistics, pricing and sizing in a market that's huge and exploding
Key claims from this episode
Chapters
Quotes from this episode
It's very hard to, like turn a side hustle into something that's venture scalable. because there's a lot of work that needs to be done before you even think about generating any revenue.— Nate Spiteri, on why building part-time doesn't work (06:41)
Everyone was telling me, you're never going to close a round in December, like you. Basically, if you haven't raised in November, you might as well just cut around and and just reengage in January, which to be honest, thought was, in my case, anyway, a bit of a load of crap,— Nate Spiteri, on closing a round before year-end (08:00)
It took us a long time to find out ideal, investor profile. And so to get to that point, we had to speak to almost 1000 investors.— Nate Spiteri, on the scale of the raise (11:04)
You do deal with like 99, 95% no's.— Nate Spiteri, on the reality of fundraising (11:30)
I think if you get the first investor, you almost double your pressure to get the rest.— Nate Spiteri, on the first-yes paradox (16:55)
We took the approach. We were just going to build the actual product really fast. into like the leanest version possible,— Nate Spiteri, on building rather than waiting for proof (19:55)
Themes Nate returns to
- Treat fundraising like a sales pipeline — find your ideal investor profile the way you find your ICP, then double down on it
- Relentless, not aggressive — be relentless in outreach but personable and authentic so investors get a real feel for you
- Internal discipline over hustle culture — Nate is not in Silicon Valley and doesn't want to embed hustle culture, but if things need to be done they have to be done
- Managing burnout — a partner, a dog and exercise as the three things that kept him from burning out over 12 months
- Building fast over perfect proof — ship the leanest version of the real product instead of a throwaway MVP