How to reach people who are out of your league, according to Dom Pym
Dom Pym co-founded Up and has backed hundreds of Founders. Here's the cold outreach that actually reached him - and why chasing someone 100 times works.
Most Founders draft a cold message, stare at it, and delete it. The person on the other end - the mentor, partner or backer who seems too big to reply - is too successful, too busy, too famous. Reaching out feels like an imposition.
Dom Pym has spent his career on the receiving end of that outreach. He co-founded Up, one of Australia's fastest growing digital banks, and has personally invested $85 million into the Australian startup ecosystem. On Life After Launch, he told us exactly which approaches got through to him - and made the case that the reluctance to reach out is the actual mistake.
The person you're afraid to message probably needs to be asked
Early in his career, Dom wanted help from Marty Howell, co-founder of realestate.com - at the time running one of the top property platforms in 18 countries. Howell didn't reply. Dom kept going. Howell was in hospital at one point and still not responding, and Dom read it as a famous person ghosting him.
Years later, Howell told him the truth: they ended up business partners because of the chasing. "I chased him 100 times," Dom says. Without the asking, Howell would never have realised how much his help mattered.
That reframes the whole dynamic. Founders assume successful people should volunteer their time, and that chasing them is rude. Dom argues it runs the other way - the up-and-comers have to do the reaching, because the person with the experience and the network genuinely doesn't know you need them until you say so. And when a young Founder asks for help directly, most people find it very difficult to say no. Dom's seen it work at every level: when Sam Altman did his world tour, an Australian crew simply reached out - and got 3,000 people into an event with him, 100 of them backstage. He'd never visited Australia before. Nobody thought he'd come.
The most creative outreach Dom ever received
One Founder wanted Dom's attention and didn't send an email. He built an entire website on its own domain. On it: a fabricated video interview with Dom - answers cut together from Dom's other appearances, since they'd never met - and a working redesign of Up built on the bank's public developer API, loaded with the Founder's own product ideas.
Then he sent Dom a single URL.
It worked. The two connected, and that Founder now runs a highly successful business in the US. Years later, Dom is the one making introductions on his behalf - the outreach turned into a relationship that outlived the ask.
The lesson isn't "build a fake interview." It's that effort is legible. Dom could see instantly that this person had spent real hours understanding his product and his thinking. A personalised artefact - a working demo, a redesign, something made specifically for the recipient - carries a signal no email template can fake.
The $1 coin letter
The lowest-tech tactic Dom shared might be the most repeatable. His team once ran an outreach campaign by post - because nobody sends letters anymore - and sticky-taped a $1 coin to each one. The note framed it plainly: "here's a dollar, which is like a down payment on our relationship." Keep it, or send it back.
It was tactile, it was different, and it produced the best response rate of any campaign they'd ever run. In an inbox of identical cold emails, a physical object on a desk is a pattern break. The dollar isn't payment - it's proof that a real person spent real effort on this specific recipient.
What to actually do with this
Strip it back and Dom's playbook is three moves. Persist past the silence - non-response is the default state of busy people, not a verdict on you, and the follow-up count that feels embarrassing to you is invisible to them. Make something instead of asking for something - a redesign, an analysis, a demo built for that one person proves effort in a way words can't. And break the channel - if everyone's in the inbox, be in the letterbox.
The thread through all of it: Dom doesn't describe any of this outreach as annoying. He describes it as the mechanism by which he found business partners, portfolio Founders, and people worth backing. The people you're afraid to contact built their careers being contacted - as mentors, partners, and yes, sometimes investors.