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Welcome to Billion Dollar Energy. I went from a farm town in Canada to a Silicon Valley insider and venture capitalist. I share secrets and insights to help you build wealth, legacy, and freedom.
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Expense receipts shouldn't require a search party
Adam spent 20 minutes looking for a $36 receipt. His finance team sent three Slack messages. Someone made a sticky note.
Ramp would have matched it automatically the moment he swiped. Auto-coded, in-policy, synced. Nobody had to ask Adam for anything.
This is what finance looks like when it runs itself.
Your team can be Adam. Or they can not be Adam.
I’m feeling introspective this week. From time to time, something snaps me out of the daily grind that makes me reflect on my path through life so far. How did I get here? This is one of the big reasons why I tell people to ask themselves ‘Why not me?’ Our path is not set in stone. There is nothing inherently special inside someone who has “made it” compared to someone who hasn’t. Sometimes, all it takes is the right mindset and a little nudge.
Last weekend, I got on a flight to LA and sat down next to Seth Rogen. This moment has put me in a headspace to reflect on how much my life has changed.
We talked for most of the flight, but I couldn't stop thinking about a version of myself from 20 years ago: 16 years old, in a farm town of 2,000 people, watching Superbad in a theater with the same friends I'd known since kindergarten. Some of us stole the cardboard cutout of McLovin from the lobby that week, and it made the rounds through our friend group for months, showing up in bedrooms, backseats, and house parties.
You can hear him saying it.
That town didn't have much room for reinvention. Most people who grew up there stayed, worked at the plant, or married someone from two towns over. I don't say that as a knock on any of it. I say it because living a life elsewhere wasn't really on the menu, and a teen comedy about growing up and saying goodbye to lifelong friends was one of the first things that made me believe it could be.
My father gave me the version of that belief that actually stuck.
As most of you already know, my dad is blind and never graduated high school. My mother worked while he stayed home, and by every conventional measure, we didn't have a path to places like San Francisco and Los Angeles. But he told me something once that I've never been able to shake:
"Jenny, you can be anything they can be. They are not better than you."
I didn't fully understand what he meant at 16. I understand it completely now. He was removing a ceiling I didn’t realize I had unconsciously accepted.
At 17, I pitched a billionaire to fund my education, with no real reason to think it would work. It worked. That was the first domino, and the ones after it took me to Silicon Valley, writing a book, launching my own venture fund, and eventually onto a flight where the guy from Superbad happened to be sitting in seat 14C.
If any of this sounds familiar, it’s because I’ve told part of it before.
A few months ago, I wrote about rewatching Superbad and texting my childhood friend Mike for the first time in years. We grew up in the same town, at the same school, with the same starting line, and by 36, our lives don't look anything alike. I still don't have a clean answer for why my path worked and his didn't. I only know the movie keeps finding its way back into my life at exactly the moments I need to take a step back and reflect.
The distance is the part I still can’t get over.
I used to scrape ice off my windshield in a town most people will never hear of. Now I live in the City of Angels, I run a venture fund, and I occasionally end up mid-conversation with someone whose face I used to hold up as a joke at a house party.
None of that erases where I started. If anything, it's the only reason any of this means something. The version of me in that farm town needed proof that the walls were movable before she could ever try to move them. Superbad, a stolen cutout, and one blind father who refused to let me believe I was smaller than anyone else, that was the proof.
Where you start doesn't have to be where you end up.
Hit reply and tell me: what movie, moment, or person made you believe you could aim impossibly high? I read every single response.
Jenny
P.S. If you haven't read the 35 inflection, it's the closest thing I have to a part one of this story.
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