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Show me a startup Founder and I'll show you someone with a boatload of health issues.

But why? Why is nearly every Founder who is neck-deep in the trenches of their startup suffering from physical, mental, and emotional issues? More importantly, why do we feel like these sacrifices are justified?

We are surrounded by tons of Founders all essentially making the same mistakes at exactly the same time, particularly with our health, at which point we assume that must be "how it goes." And yet, the reason we're all blowing ourselves up is that collectively we're doing it all wrong.

Are Sacrifices the Cost of Being a Founder?

To an extent, yes, we do have to make sacrifices to build a startup. We need way more resources than we can possibly pay f...

We all understand the "startup struggle" part of the process, but how does that other part, where we make a bunch of money work?

Doesn't it seem to be the case that there's endless lore about the early startup days and then the end where the company gets big, but not much clarity about what happens in between?

It's kind of like one of those "comeuppance" montage scenes (Wall Street's Bud Fox come-up is my personal favorite) that shows the time-lapse of the Founder struggling, and then all of a sudden on top with all the fancy things.

No One Sees it Coming

I've interviewed countless Founders of every possible industry who have "made it" and I always ask them the same question: "When did you realize you were about to be successful?"

They alwa...

About once a decade, the U.S. Financial Markets implode. It happened during the "Dot Com Bust" of 2001, again in the financial meltdown of 2007, and is now upon us in a Post-COVID recovery.

For Founders, while we understand the broader implications of "this is bad" we may not be aware of how it affects us personally now that we're running a startup in this environment. Fortunately, we have plenty of history to fall back.

What Just Happened?

In short, many of the tech IPOs that are the holy grail of startup investments have failed in an epic proportion. The reason that matters is that for startups, all of our fundraising is tied to the idea that someday there will be a massive pot of gold at the end of this journey.

Well, that pot of gold tu...

What would happen if we went straight up nuclear on the staff today?

That's right — a total hard reset. We burn the whole thing down and start all over again. We stomp out the politics, throw the dead weight overboard, and wipe the slate clean altogether.

Depending on how our day as a Founder is going, that might sound like our worst nightmare or pure heaven. But it's actually a very real question that Founders can and should contemplate, in good times and in bad.

For argument's sake, let's say that we were forced to shut down and let everyone go, but then managed to raise some capital to resuscitate the business and had a chance to do it all over again (we actually did this with Zirtual.com when we bought it, so it's not just mental exerci...

“I became an investor because I understand how to build businesses. It excites me. I enjoy the startup phases of businesses and enjoy being involved in many at the same time.” says Joanne Wilson, Angel Investor with 95 investments under her belt, otherwise known as “Gotham Gal”. This matches here credo — “Work hard and play hard.” Living in New York City, she is a self-professed foodie who also loves to cook and host and is always up on the latest cultural and fashion trends her city has to offer.

Joanne primarily invests in consumer based products and that covers a wide range with an emphasis on women and minority founders. “I have focused my thesis on female entrepreneurs — a decision that is more practical than philanthropic. She also w...

What if this very moment is our last - and best - shot at success?

It's kind of hard to think about, actually. We tend to think about our careers as a whole in a progressive way, where we start at the bottom and climb our way to the top. But our startups are more like a job where we can be the mailroom clerk one year, the CEO the next year, and the doorman the next year.

It puts us in a tough spot because we're constantly wondering whether this is our moment. For those of us that haven't been around long enough, it's worse, because we may not realize yet that those peaks and valleys even exist — all we've seen is the come up.

Striking Lightning

Most startup Founders get one glimpse of "striking lightning" when all of the pieces of momentum ...

Yes, there are Founders who take personal money off the table during funding rounds, and no, you probably won't be one of them.

For the unfamiliar, there is in fact a practice whereby investors are sometimes willing to directly purchase shares from existing stockholders (like the Founders) in order to create some liquidity for them personally. It's called a "Secondary Sale" and it simply means the proceeds go to the Founder, not to the company proper.

The problem is most Founders just hear "investors will give me money personally" and assume it's a regular practice. It's not, at all, but it's also not something that's very well explained to Founders either. So, here's how this actually works.

When to Ask

A few things have to happen for us t...

I grew up with zero choices. As a broke kid with a single mom, I never really understood what people were talking about when they said they could "choose" how life worked for them. I just got used to being stuck with zero choices and dealing with the outcomes.

"Oh, you want to pay me 'ones of dollars' to mow your lawn? OK! I guess that’s what I have to do, because I need money."

Later on in life, I got to live this all over again as a broke startup Founder. No one presented me with an abundance of choices, I just took what I could get because I was constantly leveraged. Unfortunately, that runs a bit counter to the popular narrative we're hearing in startup culture, where we somehow have all the choices in the world and we're simply not ma...

In the moment when our startup ship is sinking to the bottom of the ocean, everyone has jumped on the life rafts, and we're wondering what the world will think of us, what goes through our minds?

Whether we fail or not, we've all run through the same scenarios. The only difference is when we fail for real, we get to see what actually happens. We get to see what kind of support we really have and what people will really think about us.

But what's both sad and comforting is how few people will care at all.

No One Actually Cares

In our minds, we're sitting around thinking that everyone is against us. Every investor, employee, partner, customer, even random people we don't know are sitting around taking turns bashing us. In every one of our soc...

The only way we grow is to bite off way more than we can chew.

There's this notion, however, that the way startups are built is by first building the entire product, team and infrastructure, and then attacking our market. While that sounds fantastic, it's actually not how startups grow.

We grow when we take giant leaps that are way beyond our current capacity and then figuring it out from there. In order to do that, we need to feel comfortable with taking these steps.

Am I Lying?

The first problem we all deal with is feeling like a fraud. We assume that if we're not 100% ready today, then we shouldn't even attempt to pitch our product to customers or investors. If that were true, startups would never get past a single Founder.

The reality i...