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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…

Why risk-entrenched entrepreneurs should sink money into real assets, too — as counterintuitive as that might sound.

million dollar house to invest my cash in to diversify from my risky startup
Photo by Marvin Meyer on Unsplash

As someone who went from a 6-figure finance job to losing my life savings in one fell swoop through my first startup, I’ve lived frugally since the day I graduated college. Even my Wall Street salary felt precarious, as I watched high attrition and moody bosses seal the fate of many an ambitious employee. Once I left the “rat race” to begin my own ventures, my mindset around money centered on one strange principle: Don’t spend it; unless it’s on potentially revenue-generating business activities, in which case, spend away.

Throughout the ups and downs of business failures and successes, losing…

It was the best of times and the worst of times — but nobody prepared you for the problems your “success” would bring.

entrepreneur reacting to something unexpected going wrong after his business takes off
Photo by Headway on Unsplash

For the first 18 months of my entrepreneurial career, I worked in the vacuum of my dark, 457 square foot studio apartment, spending thousands of dollars each month without making a single sale. It was glorious in that my isolated bliss shielded me from the woes I would have encountered if that business were booming all that time…

While that costly, customerless venture went down in history as my 6-figure failure, I was blessed — or should I say cursed — to stumble upon some subsequent ventures that did generate interest and sales. A lot of them. At an incredibly…

And that’s okay — some of us go from zero to $1 million, while others go from $100 million to $1 billion.

entrepreneur who is cut out to be a millionaire entrepreneur, not a billionaire CEO
Photo by DISRUPTIVO on Unsplash

Let’s clarify one common misconception: Entrepreneurs and CEOs are not necessarily the same thing. Many entrepreneurs are their startups’ CEOs (for a time, at least), but many more CEOs never were — and perhaps may never be — entrepreneurs.

Earlier in my career, I entered the world of mergers and acquisitions thinking I’d get a glimpse into the inner workings of companies, their financials, and the entrepreneurs behind them. That was partially true: I did get a robust look inside the businesses we sold for $100M+, and I was intimately acquainted with their financials. I even got to work closely…

Don’t get blindsided by a $30k unexpected bill like I did.

shocked entrepreneur who’s blindsided by a $30,000 unexpected bill for his startup
Photo by Taylor Deas-Melesh on Unsplash

$30,000. My jaw dropped when I opened up the final 5-figure bill of the week. Last month, my company had dropped an extra $18k on one-time marketing expenses, planning to keep our spending lean through the rest of the year. You know what they say about the best-laid plans, right?

I scrutinized each bill, called each vendor, and verified each line item to make sure we weren’t getting scammed. No such luck. The $30k wasn’t an accident, and it wasn’t negotiable. It was due now — all of it. Just like that, I was going to drain a huge chunk…

From an entrepreneur who flushed her 6-figure savings and prestigious career down the drain at 24.

frustrated entrepreneur whose mental health has been compromised by his startup
Photo by christopher lemercier on Unsplash

The scariest day of my professional life took place in a high-rise cubicle, with political riots burning down the city and bankers rushing home to take cover in their luxury condos. Despite the commotion all around me and the footage of flames, vandalism, and violent attacks right outside our building, the sent email in front of me was far more frightening. Within a split second, I was overcome with petrifying anxiety, paralyzed in my chair, too afraid to leave, yet equally afraid to stay.

That email was nearly three years in the making, yet it felt jarringly abrupt and catastrophically…

Rachel Greenberg

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