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).
I was born on the East coast but always identified with the West coast. …
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 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.
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…
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…
For the past few years, I’ve been invited and re-invited to speak at some of the nation’s top business schools. I’ve shared the stage (or panel) with some very impressive entrepreneurs across various industries — tech, sports, media, healthcare, fintech, you-name-it. Sometimes I’ve been the most experienced and accomplished entrepreneur on the stage and other times I’ve been the least; however, they always invite me back based on one unique differentiator.
It’s all based on a controversial statement…
As a newly-minted CEO (or whatever you call yourself to quell your parents’ disappointed, fear-stricken cries in response to your recent — arguably reckless — corporate exodus), you’re probably excited to start putting your new title to work.
Step 1: Create a corporation, pay your formation fees, and name yourself CEO. This is really just the legal bit and more of a formality.
Step 2: Update your LinkedIn — everyone must know of, respect, and congratulate your new self-appointed promotion as CEO of the next big thing.
Step 3: Quickly return to Step 2 and attempt to erase all evidence…
Many people have bought into the fallacy that making thousands or tens of thousands of dollars has to come at the expense of tens or hundreds of hours of grueling, tedious, or at the least mind-numbing work. The consensus seems to acknowledge two viable options to attain those “riches”:
As a former investment banker, I’ve seen more than a few golden parachutes written into deal structures for a wide variety of companies and industries. What I have never seen, however, is an ousted CEO receive a golden parachute (especially one in the hundreds of millions of dollars) for a deal that fell through — especially one plagued by subsequent disputes and red flags. The golden parachute promised to WeWork’s former CEO, Adam Neumann, seems to do just that.
In case you aren’t familiar, this is how Investopedia defines golden parachute:
Imagine this: You’ve spent the past nine months perfecting a product, surveying beta users, running focus groups, and even announcing your offers on an auditorium stage. You’ve hired a new marketing team for $3k/month and have revved up your ad spend ahead of your upcoming launch that’s set to take place in 90 days.
Then, on a whim, you scrap your entire marketing strategy and launch timeline, slash your prices, and impulsively go to market right then and there, the very following week — with an untested offer structure.
Sound like a good idea?
Well, I tried it.