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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 born on the East coast but always identified with the West coast. …

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 that there is not necessarily a positive correlation between the amount of money you put into a company and the subsequent success (sales, profit, growth, etc.) that company can go on to achieve.

I’m also living proof that every dollar you spend is not equal. …

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 as possible, while attempting to build a business in a vacuum).

These were the early days. We were making money, but we were also spending money — and we were spending more per month (on the business) than we were bringing in. Also known as not being profitable.

However, there…

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 to use this example as an excuse to justify your own entrepreneurial self-doubt or shortcomings.

Don’t worry; I meant what I said in the title, and I will deliver.

I’ll even offer some helpful takeaways that you may be able to apply to your own current startup or other future…

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 top of my lack of emotional availability, I’ve also never felt very maternal. I see babies kind of like I see socks. They’re (sometimes) cute? They’re cool. I guess…

Do you see where I’m going with this? The fact that I could even write that last paragraph and admit it…

From a finance person-turned-entrepreneur and startup consultant. And yes, I’ve made this mistake too.

a professional finance person nickel and dime-ing her prospective customers and accidentally spiting her own startup
Photo by Kelly Sikkema on Unsplash

I stood behind a table covered in holiday-themed dog treat bags as the canines descended upon me. Dogs of every breed pulled their owners from outside the park and across the street to my table. Once the ravenous stampede (and their seemingly more ravenous) owners licked, chewed, and snatched my table clean, they disappeared into the busy Los Angeles neighborhood, and I was left alone and empty-handed.

What began as a “Merry Chinmas, Happy Chinukkah” event for my Japanese Chin Esmeralda to frolic with her rare-breed clan turned into a successful marketing event for a friend’s Los Angeles-based pet treat…

9 months after getting 100% rejected, this founder turned the tables and bagged his dream team without sacrificing an ounce of equity.

founder who successfully persuaded a hesitant partner to join his team 9 months after a total rejection
Photo by DISRUPTIVO on Unsplash

About 9 months ago, an enthusiastic founder approached me, seeking a potential partnership. He was fairly open to a variety of working arrangements and compensation structures, and I’d bet some people would have seen the potential money grab opportunity and taken him for a ride. Unfortunately, a few reservations led me to decline the partnership, even as the founder continued to bid up his offer, hoping more money, a revenue split, or generous equity would win me over.

I didn’t decline his offer(s) because I didn’t appreciate his venture or disliked the space. I didn’t decline it due to my…

There’s a reason many startups begin in humble garages, far from the limelight.

famous entrepreneur suffering the inescapable attention of a large following
Photo by Erik Mclean on Unsplash

Even if you’ve been living under a rock for the past few years, I’m pretty sure the word “followers” has edged its way into your dark, otherwise solitary hole. Thus, when asked what they want when they grow up, it’s no surprise kids often say “fame” or “followers” (alongside money, of course). If you asked an aspiring entrepreneur what they’d like — or what might give them a leg up on the journey to success — you might hear a similar answer: an audience.

There are primarily two types of aspiring entrepreneurs:

  1. The solution-focused entrepreneurs with a product or service…

Avoid the uphill battle that comes from choosing the wrong role

person who decided to become an entrepreneur for the wrong reasons when he should have been a creator
Photo by ConvertKit on Unsplash

About six months into my second startup — after the public 6-figure failure from which I aimed to recover — I finally had a solid product ready to launch. It was then, when I shifted from the early stages of building a team, seeking out partners, and creating the piece de resistance that catapulted my vision from nothing to something, that I realized entrepreneurship was no longer what I’d expected. …

And the counters that will land you more desirable jobs that won’t feel like work at all.

entrepreneur in a lucrative career he hates, thanks to bad business advice
Photo by Mubariz Mehdizadeh on Unsplash

It was 11 am on a Wednesday, and I hoisted my giant snail’s behind out of bed to start my day bright and early like the successful entrepreneur I aspired to become. Then, I mosied over to the ridiculously priced gourmet market down the street for some sustenance — the arduous trek deserved a hearty (and costly reward). …

Rachel Greenberg

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