About Me — Rachel Greenberg

Just another day in my dog’s shadow…working hard to afford her extravagant lifestyle. I also work with startups, when she lets me.

If you don’t like dogs, startups, coastlines, and a healthy dose of sarcasm, I may not be your cup of salted almond milk cold foam iced coffee with 9 pumps of sugar-free vanilla syrup, 7 packets of salt, and 2 Splenda (Starbucks baristas, you are the real MVPs).

My life in a pistachio shell:

I was born on the East coast but always identified with the West coast. After more than a couple of decades of seasonal depression, barely surviving the tundra of North Carolina (yes, the South does get cold), I finally got my invitation to embrace the California lifestyle, with my first official job at JP Morgan in San Francisco, working in asset management.

Unfortunately, my early career in finance took me back to the East coast, so a few more years of teeth chatteringly cold winters and heated blankets under my desk would be the reality of my subsequent investment banking career. If you’re going to be sitting at a desk, writing pitch books and building financial models until 2 am anyway, is a little climate discomfort all that much worse?

Direct route to failure, exit 1 on the right

I’ll spare you the details of life in finance — perhaps that’s for another article, another day. All you really need to know is that I hatched a little plan to escape, called “startups”, and was welcomed into the entrepreneurial fold with my first swift taste of very expensive failure. Suffice it to say, great and valuable lessons were learned along the way. If you want to spare yourself the hundreds of thousands in expense and heartache, you can learn mine here:

But you can’t like business AND art…(yes, a recruiter actually told me that…four years before I got hired at her firm’s esteemed M&A group)

Perhaps I should have mentioned startups were my goal all along — pre-finance, I knew I wanted to build and grow companies. My favorite thing in life (aside from dogs and cliffside beaches) is creating things…a lot of things. All the time. Paintings. Screenplays. Businesses. You name it…(see pic below)

In case that sparked any questions, I’m including a few relevant articles below — both how I became an award-winning screenwriter in three months and how I got a 200x ROI on one of my lowest-budget startups.

I’m also one of the few fortunate people lucky enough to meet my one true soulmate fairly early on in life, so I’ll leave our love story below:

Fun facts about me:

• I’m a lactose-intolerant lacto-ovo pescatarian (In other words, I don’t eat cute, furry things, but I do eat things that swim…and while I won’t eat fluffy flying creatures, I will eat their unhatched offspring — preferably scrambled or soft-boiled. That also means that I eat milk products like ice cream and cheese, even though I really shouldn’t…)
• Sometimes, I just can’t be normal. Case in point: My engagement ring is green…and took us two years to locate, since apparently green diamonds don’t grow on trees…
• I once walked 20 miles in one day (in flip flops) from the Ferry Building in San Francisco to Sausalito, across the Golden Gate Bridge, and back.
• I’m petrified of heights, and since I also enjoy a good bit of adrenaline and setting myself up for a challenge, I also love rock-climbing.
• A rock climbing and sushi combo makes for my perfect date. Throw in a puppy or two, and we’ll probably get married.
• Speaking of marriage, since I can’t be normal (per the green ring reference), I also couldn’t simply go wedding dress shopping at a bridal salon. Instead, I custom-designed and ordered my gown…wait for it…from China! During the pandemic. And guess what? It actually worked.
• I currently have three fur children: Flumpster (a 7-year-old Holland Lop — it’s a rabbit), Esmeralda (my two-year-old Japanese Chin soulmate), and Chinderella (Esmeralda’s six-month-old little sister from another mister).
• I love hiking — especially cliffside, oceanfront hikes with stunning panoramic vistas. My biggest recommendations would be Corona del Mar (Newport Beach) and Heisler Park (Laguna Beach).
• If it’s too cold to hike, I always love a good drike (Drive hike). Drike definition: a hike taken via a vehicle, in which the sole purpose of the drike is to experience nature just like an on-foot hiker, without subjecting oneself to the cold.
• Yes, a mike is also a hike (Mall hike). We do this around holiday times or if it’s too cold for a hike and too rainy for a drike. This is rare in Southern California, but occasionally it happens.
• I’ve somewhat recently discovered Medium, and so far it feels like my biggest guilty pleasure. I’ve always loved writing, but I have a hard time justifying time spent on things that don’t guarantee a significant ROI.
• My other guilty pleasure is real estate. I love the eye candy that the modern architecture across the Southern California coast provides, from Malibu all the way down to San Diego — the glass-paneled mansions are endless and truly breathtaking. I would pay a ridiculous amount of money to get an in-person tour of every single cliffside modern mansion…plus a little bio about the owner, just for research purposes, to better understand how the majority of the SoCal real estate wealth was created. Is that weird?
• I’m a coloratura soprano, with about six or seven years of classical opera training. My fiance believes I should embark on a second (third? fourth?) career in “popera”, in which I sing “pop” music in the operatic style. I’m not opposed, but again, not sure about the ROI on this one.
• The vast majority of my time is spent building businesses, consulting for others, advising, and sometimes stepping in as an interim “ghost” CEO or cofounder. I advised or consulted over 500 startups in just the last year.
• I write mostly about startups, entrepreneurship, and business, and as such, have achieved top writer status in those three categories. (Well, it’s “Startup”, but that’s because apparently nobody wants to tag the plural…)
• If I could be my dream person — the ideal version of myself, having achieved all my goals — I’d be a mix of four people: Aaron Sorkin (screenwriter of The Social Network), Wil Schroter (founder and CEO of Startups.com), J.K. Rowling (needs no introduction — Harry Potter, come on), and Tim Ferriss (he also needs no introduction, but he wrote The 4-Hour Workweek, and my personal favorite, Tools of Titans — such an inspiring read!).

In case you weren’t turned off by the drike, mike, or popera, maybe we can be friends

If you’d like to keep up with me or connect, I’ll leave a few links below — always happy to meet new, inspired, aspiring creators.

• My LinkedIn
• My personal website…kind of a work in progress, depending on when you’re seeing this.
• One of my many emails: [email protected]
• I try to avoid the socials as much as I can (back to the whole ROI for my time decision), but a LinkedIn message or email is probably the best way to get in contact with me.
• If you can find my Facebook, you’re welcome to friend me there, too — though if you’re looking for something other than a barrage of Japanese Chin pictures, you may be disappointed…
• If you want to become my BFF, there are two ways: 1) pitch me an idea you want me to help co-found and make me absolutely love it and you enough to hop on board, or 2) buy me a third Japanese Chin puppy so my fiance can’t say no (it’s impolite to refuse a gift, and you certainly can’t return or regift a puppy).

Startups, dogs, California, sushi, real estate…I think that pretty much sums me up. Oh, and the most annoying Starbucks order a barista has ever heard. If you can guess my full order, I’ll send you a Starbucks gift card. Hint: it’s obviously not on the menu, and no, I didn’t give the whole thing away in the first paragraph.

Also, for anyone curious about the mysterious green engagement ring to which I’ve alluded, I’ve linked that article below, as well.

Thanks for stopping by — I, unfortunately, must depart — my master is calling, and a humble servant can’t leave her royal highness (Esmeralda) waiting.