You're sitting across the table from someone you've never met. Maybe it's an investor evaluating your pitch, maybe it's a founder you're considering backing. And before a single word about valuation or vesting schedules comes up, there's a quieter question running underneath everything: who am I to be talking to this person?
JJ Goldsbury, a strategic advisor and capital strategist who's spent 15 years moving between energy, infrastructure, finance, and real estate, says that question, and the fear behind it, is more powerful than most of us realize. In his keynote, The Courage to Create, the Conviction to Believe, at the June Rockies Investor Capital Expo, he shared the story of how pushing past it just once led him to his unicorn.
The Setup Nobody Plans For
After exiting a commodities business in 2022 — one he calls more of an "escape from a bad partner" than a true exit — JJ figured he'd cracked the code on private equity. He had deal flow. He had a network. He had confidence. What followed instead was a stretch of bad bets and worse investments.
Then came an ordinary morning at the gym. JJ overheard a stranger telling a friend he'd lost everything — couldn't pay for his kid's college, didn't know what came next. JJ walked over, introduced himself, and offered the man something simple: an evening of his time. They ended up talking for four hours. By the end of it, the man asked JJ what he did for work — and the conversation that followed led to an introduction to a founder building grid-scale battery technology rooted in nuclear reactor science.
The Breadcrumb
A few months into advising the company, JJ asked a casual question: where's this business based? The answer — Tri-Cities, Washington, a place almost nobody outside the energy world has heard of — happened to be where JJ grew up.
It wasn't a calculated move. It was a coincidence he chose to follow. And following it meant getting past a small, nagging hesitation: this guy might be more accomplished than me, more connected than me — who am I to dig in here? JJ pushed past that fear anyway. That one relationship, built on a willingness to stay curious instead of intimidated, became the deal that changed his trajectory.
Why This Matters For The Rest Of Us
It's tempting to hear a story like this and file it under "luck." But the truth is that opportunity rarely announces itself clearly. It shows up disguised as a stranger at the gym, an offhand comment about where a company is headquartered, a connection that doesn't look significant until much later. The skill isn't predicting which breadcrumb matters — it's having the habit of following them at all.
That habit gets blocked by the same thing on both sides of the cap table. Investors hesitate to engage with entrepreneurs they don't yet understand. Business leaders hesitate to push themselves into rooms where they feel out of their depth. JJ's point is that this hesitation comes from the same root — a fear of not being enough, or not being worth someone's time — and it quietly costs both sides relationships that could otherwise compound into something real.
The Takeaway
You don't need a dramatic gym encounter to apply this. You need a willingness to follow the small, unremarkable thread — the offhand detail, the unlikely intro, the conversation that doesn't seem urgent — rather than dismissing it because it lacks a clear ROI.
The biggest opportunities rarely arrive labeled. They show up as breadcrumbs. Your job is simply to notice them and to be willing enough — past the fear — to follow where they lead.