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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
Picture of me, my dog Esmeralda, and Laguna Beach

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.

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
man holding money

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.

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
dog face

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…

1,000 acquisition rejections taught me why entrepreneurs really sell their businesses — and it isn’t always a cause for celebration.

entrepreneur excited about selling his business
entrepreneur excited about selling his business

My throbbing fingers ached with searing pain from the repetitive motions: Research, Review, Reject, Repeat.

  • $200k asking price, $400k LTM revenue, and $330k profit. Sounds great, right? Pass. Their niche was banned across the world’s largest search engine and second-largest advertising platform.
  • $120k asking price, robust tech platform serving thousands of customers, maintaining 70% profit margin. Pass. The tech was built on a system that will no longer be supported, so a complete software rebuild is required.
  • $39k asking price, innovative B2B product with hundreds of paying subscribers, and $0 ad spend. Pass.

No, it isn’t failure — not even close.

an entrepreneur’s biggest fear may not be failure
an entrepreneur’s biggest fear may not be failure

“I’m afraid I won’t become Greg.” That’s what I told my fiancé as I stared at the wooden table between us, while my mind wandered far, far away.

Ever since breaking free of Wall Street’s golden handcuffs in exchange for the massive uncertainty, self-doubt, and financial insecurity that comes from pursuing entrepreneurship full-time in the nation’s wealthiest city, I’ve accepted fear as a main character and relentless constant in my life. …

These 8 flubs cost their founders lucrative acquisitions at the 11th hour — and I was the would-be buyer.

entrepreneur who made a mistake that cost him a 7-figure business deal
entrepreneur who made a mistake that cost him a 7-figure business deal

735. That’s the number of businesses I’ve passed on in recent weeks. That’s 735 chances for a founder to “wow” me and 735 times they’ve fallen short. Coming from an investment banking background, I thought I was perfectly poised to sniff out, properly value, and snap up ideal acquisition targets. To my surprise, finding an attractive business to acquire these days is a lot harder than it looks.

Of course, I can’t attribute all 735 rejections to a faulty founder or a subpar or even misvalued business.

  • Some businesses represent fairly valued assets with high growth potential, but simply lack…

Who’s bought, sold, and built over 24+ companies and generated billions in sales.

$700 million serial entrepreneur
$700 million serial entrepreneur

A black pickup truck parked along the 45-degree hill awaited our arrival, concealing the identity of its unassuming owner. A gray-haired man with a jovial face stepped out to greet us, opening the door to the $2.7 million architectural masterpiece and beckoning us in. Within seconds, we were enveloped in the panoramic views of the stone and glass palace. Greg didn’t need to show us this house — he was a serial entrepreneur simply doing a favor for his real estate agent daughter.

At that moment, we had no clue who Greg really was. However, three houses, two lots, and…

From an entrepreneur who made an extra $250,000+ by bucking the trends and challenging the advice of marketing “gurus”

unconventional new marketing strategy that bucks the trend
unconventional new marketing strategy that bucks the trend

The first few years of my entrepreneurial journey were rough — and by that, I mean expensive and unprofitable. I followed conventional wisdom, hired top-notch advertising teams and marketing “gurus”, and dug myself a six-figure hole to climb out of. Finally, after about four years of doing things the “right” or “conventional” way, I fired all my teams and decided to start breaking the rules.

In so doing, I accelerated my sales by over 1000% in just a matter of months, slashed my customer acquisition cost, and added over $250,000+ to my bottom line while cutting out $50k+ of unnecessary…

Rachel Greenberg

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