Wall Street Investment Banker → Entrepreneur & Startup Consultant. “Top 10 Entrepreneurs of 2020” Yahoo Finance. CEO of Beta Bowl. Mom of 3 furbabies ❤

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

Picture of me, my dog Esmeralda, and Laguna Beach
All pictures in the above collage are owned and were edited together by the author (me) in Canva. They include me, my dog (with her permission), a Laguna Beach hike, and my fiance’s seaside proposal to 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…

This formula is proof you can launch a business for under $1,000.

Photo by Diggity Marketing on Unsplash

I’ve built companies for hundreds of thousands of dollars, and I’ve built companies for hundreds of dollars. I’ve also lost hundreds of thousands of dollars (typically on those more expensive-to-build companies), and I’ve made hundreds of thousands on companies with an initial investment of under a thousand.

I’m living proof…

What I learned in my first startup failure and how you can determine if and when to cut your losses.

Photo by Ayo Ogunseinde on Unsplash

Let’s be honest: I know why you’re here.

You’re excited to hear another startup failure story from someone whose dreams have crashed and burned before them, even better to hear it was all their fault (what a poor, pathetic loser of an entrepreneur they must be), and you can’t wait…

How a boy named Esmeralda changed my life. A love story for those who don’t believe in love.

dog face
Picture of Esmeralda, taken and owned by her owner and the author (me).

Let me preface this with the fact that I’m not a very emotional person.

I don’t open up quickly or easily and I have an auto-cringe response to most anything mushy or gushy hurled my way. I like to keep my friends, enemies, and pretty much all humans a good six to ten emotional feet away from me on a fairly regular basis.

On…

Or any career, for that matter — and it’s not too late to start asking them now.

8 questions you should have asked yourself before starting your business or any career for that matter (and it isn’t too late to ask them now)
Photo by Emily Morter on Unsplash

Last year, I made a $1.4M purchase that surprised even me. That purchase came on the heels of a months-long search for prospective startups to acquire. After hundreds of hours spent pouring through attractive opportunities, I trashed them and went all-in on a completely different industry. …

I kept my diagnosis a secret from my customers — and it gets worse

entrepreneur dealing with Covid and running three businesses
Photo by Ryan Snaadt on Unsplash

I’ll admit it: I was one of the lucky ones. Come New Year’s Eve, 2021, I was one of the fortunate few who’d successfully dodged Covid and its every variant. In fact, if I’m brutally honest, some of my businesses had even experienced quarantine boosters (in sales, not the shot)…

There’s one type of partner no entrepreneur has time for and another you desperately need. Which one are you?

A Fight With My Business Partner Exposed Her Major Flaw — And It Has Nothing to Do With Credentials
Photo by Yogendra Singh on Unsplash

I stared at the email, mentally sifting through the most succinct, palatable answer to a question I hear all too often. Unfortunately, the real answer isn’t succinct, and it isn’t what she wanted to hear. It didn’t matter; I bit the bullet and replied with an honest miniature novel.

Her…

An honest exposé from a Type triple-A+ serial entrepreneur who doesn’t always act like one

Entrepreneur exhibiting one of the less admirable stages of entrepreneurial discipline so few want to admit
Photo by Nick Fewings on Unsplash

I sat beside my former client-turned-close friend, sharing a sushi roll and ringing in the new year with a secret on my chest. I’d danced around the confession for months, repeatedly steering our conversations into lighter, less business-focused avenues. Until tonight.

She shared her big news first. I blinked back…

Business is not meant to be performative; it’s meant to be impactful

sometimes marketing itself — or a lack thereof — can be deceptive in itself; the correlation between paid marketing, social media posts, and sales may not be positive
Photo by Marten Newhall on Unsplash

If you’re anything like me, you’re no stranger to spiraling. For those less spiral-prone people, here’s a brief example of spiraling in action:

  1. A couple doesn’t post their annual Christmas post.
  2. You reach out to check if they’re “okay” — to a curt reply. Or maybe no reply at all.

Rachel Greenberg

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