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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…

A few considerations before you accept venture capital (or any other type of funding).

man holding money
Photo by Shane on Unsplash

A few years ago I received an email out of the blue that really took me by surprise.

I was at least a couple of years into my startup journey (also known as, living in a dingy 400 square foot studio apartment and trying to stretch my savings as long…

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.


Most entrepreneurs are too scared or embarrassed to check the destination plugged into their startup’s GPS.

the roadmap to entrepreneurial success that most founders are scared to or neglect to check
Photo by Christine Roy on Unsplash

I bit my tongue as the color drained from the young founder’s face, her eyes bulging as the investor’s harangue pierced into the confidence she’d spent the past 12 months fostering. He knew, just as I did, that she wasn’t quite investable yet. He and I also knew the next…

From an entrepreneur who’s worked with 100s of founders, some who’ve attained massive success, others who’ve returned to the 9 to 5 grind.

shocked bulging eye of an aspiring entrepreneur, listening to a fellow entrepreneur’s confessions about success or failure
Photo by Kalea Jerielle on Unsplash

As a full-time entrepreneur (and serial founder) with countless friends, clients, and peers in the startup space, there’s one thing I’ve learned: We’re all hiding something.

That might sound strange, deceptive, or dishonest, but I’m not talking about burying critical operational shortcomings from investors a la Theranos saga. I’m simply…

Elizabeth Holmes’ and Sunny Balwani’s text messages may serve as red flags to protect future entrepreneurs from a similar fate.

entrepreneur sending risky, success-compromising texts to a cofounder or team member
Photo by Mikel Parera on Unsplash

For those who’ve watched the rise and fall of Elizabeth Holmes and Theranos, it’s easy to call out the gravest errors that preceded their demise.

The obvious?

  • Don’t lie to investors.
  • Don’t create awkward power imbalances by dating your team members.
  • Don’t say (or do) anything behind closed doors that…

Many competent, results-focused entrepreneurs will succumb to this temptation; don’t follow their lead.

Entrepreneurs making the fatal mistake of being too reactive and quickly implementing their research-based discoveries from a competitor
Photo by UX Indonesia on Unsplash

I winced from 3,000 miles away as she enthusiastically rattled off the list of new suggested initiatives. Since this was a phone call, rather than zoom or in-person face-to-face, she had thirty more seconds of excitement-fueled speech before pausing to hear my underwhelmed reaction. …

This is the simplest way to multiply your revenue, propel your fulfillment, and expunge burnout — without spending a dime.

as you run from the business that disappoints or burns you out, ensure that you simultaneously have another completely different place to run to (so you never get bored or unfulfilled)
Photo by Yuiizaa September on Unsplash

It started as an experiment — kind of a fun, little hobby. An escape, I suppose, from the stress-inducing startup I was running, alongside another synergistic venture that had similarly drained my current zeal for business. Put bluntly, I was burnt out — but flopping over on a couch doesn’t…

Rachel Greenberg

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