"You can't connect the dots looking forward; you can only connect them looking backwards."
- Steve Jobs, Stanford University Commencement Address, 2005
Six months ago, I received a wire transfer worth more than my first-year investment banking salary and bonus!
It came from advisory shares I'd received for Zoom calls that often felt completely pointless because I wasn't sure I was adding value. The thread that led to this payout started with a birthday present: five CrossFit training sessions I almost didn't use.
I watched Steve Jobs' famous Stanford commencement speech years ago and while I liked the idea of it, I couldn't see how it would apply to my life.
“Connect the dots looking backward” he said. Only through hindsight can you see how seemingly random events form a pattern.
Seems like a smart thing to say - and makes a lot of sense to a great entrepreneur like Jobs.
I didn't even see the implicit link between this idea and the recurring theme on Shane Parrish’s Knowledge Project podcast of pursuing long-term feedback loops.
That I found Parrish’s podcast during the pandemic lockdowns and the most challenging period of my professional life (so far…!) is also not lost on me.
The threads we pull today might not show their worth for years - or even decades. Sometimes the most valuable connections are the ones we can't see forming.
This is the story of two threads I pulled without knowing where they'd lead.
I used to get so much joy out of mocking Ryan for his CrossFit obsession. My best mate had gone full cult - obsessed with eating like a caveman, religiously touching a barbell daily, training in warehouse gyms with names like "Warrior Legion" and "Titanium Forge."
I wanted absolutely no part of it. Until I did.
In the pre-pandemic boutique-fitness bubble that was New York City, I was a promiscuous gym-goer - willing to try anything as long as it was below 34th Street. The mainstay of my rotation was Exceed Physical Fitness, a block from my house. Through my regular attendance - borderline obsession, really - I became friendly with the trainers and started dabbling in what we called "CrossFit-Lite." No barbells, but plenty of lifting, carrying, and swinging heavy things around.
As I publish this on my 45th birthday, I realise that it was on this exact day in 2019 - six years ago - that a great friend and Exceed regular bought me a 5-pack of "Introduction to CrossFit" sessions. A birthday gift I didn't know I needed, from a thread I didn't know I was pulling.
I only managed two in-person sessions with Tyler Le Floch before the pandemic shut everything down. But Tyler was nimble - he shifted to video, text, and Google Sheets, and we kept going.
The timing was both fortunate and devastating. I suddenly had endless time for fitness because Ample Hills - the ice cream company I'd spent two years desperately trying to save - had just filed for bankruptcy. I'd joined thinking I was boarding a rocket ship. Turns out I'd climbed aboard the Titanic after it hit the iceberg.
I've written before about how hard that failure hit me. The barbell became my therapist. CrossFit became my refuge. While everything else in my professional life was collapsing, at least I could control whether I could lift something heavy off the ground.
As I disappeared further down the fitness rabbit hole, I asked Tyler for a nutritionist recommendation. He connected me with Dr Jamie Schehr, an accomplished athlete and nutrition coach.
Looking back, a 40-year-old recently unemployed dad overseeing homeschool for three kids obsessing about macronutrient ratios was borderline nuts. But grief makes you do strange things. If I couldn't control my career, at least I could control my protein intake.
Dr Jamie ran blood tests, reviewed my food diary, and made a few tweaks to my already decent setup - save for the pandemic-booze consumption, which we diplomatically agreed to monitor!
The most impactful change Dr Jamie made was suggesting I switch to ProMix Nutrition for protein powder. She told me it was the cleanest on the market, and that the founder, Albert Matheny, was someone I should meet if I ever got the chance.
Another thread, pulled without knowing where it led.
After several months using the products, I asked Jamie to introduce me. I wanted to invest.
I was trying to rebuild myself as an investor after the carnage of Ample Hills. ProMix felt right - great product, compelling founder, growing wellness market. But more importantly, Albert was calm and measured. No manufactured scarcity, no hype, no pressure. After the circus of my last company, his steady hand felt like oxygen.
My confidence was shot, so the cheque I wrote was modest. Looking back, I was probably protecting myself from another catastrophic loss. Fair enough.
Albert and I stayed in touch. He mentioned he occasionally made angel investments and asked me to keep him posted on anything interesting.
Nine months later, I was working on a CBD manufacturing deal in Florida - too big for my network alone, so I'd partnered with a longtime friend running a Texas family office. When we started marketing it, I thought of Albert. The deal aligned with some product ideas he'd been mulling over.
He didn't just invest - he got enthusiastic. Enthusiastic enough to ask if he could bring in another investor from his business, a serial entrepreneur named Justin.
Justin came in late - less than a week before close - so he wrote a smaller cheque than he would've liked. But the work we'd done on the deal impressed him. He asked if we'd help with some ideas he was working on.
What began as informal advice evolved into something more structured. Justin granted us advisory shares in exchange for helping craft his pitch deck, data room, and investment narrative. Honestly, it felt good to be useful again. To have someone seek out my perspective after Ample Hills had wrecked my professional confidence.
Often these calls felt pointless. Some days I'd hang up wondering what value I'd actually added. Other times it felt like box-ticking - going through the motions of advising without making real impact. The thread felt frayed, leading nowhere.
Justin's company took off and he needed us less until eventually we stopped checking in altogether. Albert, meanwhile, kept building - steady, methodical, sending monthly updates you could set your watch to.
When Albert emailed near the end of last year to tell me ProMix was being acquired, I wasn't shocked. He'd always understood his market, knew exactly which KPIs mattered, and obsessively focused on hitting them whilst raising minimal capital to preserve his returns.
The acquisition closed smoothly and the cash hit my account before year-end.
It seemed bananas to me that a birthday gift six years earlier had led me to try out a sport I used to think was a cult. Then in the face of a pandemic and lockdowns I stayed in touch with a trainer as a kind of crutch to my mental despair at my failure. And that the same failure which pushed me into a fitness obsession meant I had met Albert. Now my tentative cheque was coming back to me in multiples. Whaaaaaat!
One thread, pulled during the darkest professional moment of my life, had just paid off in ways I never could have predicted.
Six months later, my phone rang. Justin.
I literally couldn't believe my ears when he told me.
His company had secured a significant transaction. An investor wanted to buy out everyone else, which meant those advisory shares we'd received two years earlier - for calls that often felt pointless - would result in a payout worth more than my return on ProMix!
We hadn't heard from Justin in over a year. His industry had shifted, his strategy had pivoted, and honestly we'd written off any value from those shares. This felt like a joke… it was a F#&!ing miracle!
Within two months, the money hit my account. Again.
Two threads, pulled years apart. One during a pandemic whilst hiding from professional failure. Another in the final week of closing a deal that almost didn't happen and certainly didn't need to happen.
Both leading to outcomes I never could have orchestrated or predicted.
This is what Jobs meant. This is what Parrish keeps banging on about.
I pulled the CrossFit thread when I was mentally crushed and unemployed, using fitness to avoid feeling the full weight of professional failure.
I pulled the Justin thread when I was tentatively rebuilding, unsure if I still had anything valuable to offer. Neither felt strategic. Both felt small. One was literally about protein powder.
The lesson isn't that you should optimise for maximum thread-pulling or network more aggressively. It's simpler than that.
Stay open.
Help people without knowing if it leads anywhere.
Show up for calls that feel pointless.
Make modest bets when your confidence is shot.
Trust that some of these threads - not all, but some - will weave into something meaningful years down the line.
The hardest part isn't pulling the thread. It's living with not knowing where it leads.
As I turn 45 today, I'm thinking less about the money and more about the threads still unravelling. The connections I'm making now that might pay off in 2030. The calls that feel pointless today but might matter in ways I can't yet see.
You can only connect the dots looking backward. But you have to be willing to pull the threads looking forward.
