ArticleWhat if I Fired Everyone and Started Over?

What if I Fired Everyone and Started Over?

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 when we bought it, so it's not just mental exerci...

Article“​It’s Not All About The Concept”

“​It’s Not All About The Concept”

“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...

ArticleThis Could be Our Last Shot

This Could be Our Last Shot

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 ...

ArticleWill Investors Let Me Take Money Off The Table?

Will Investors Let Me Take Money Off The Table?

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...

ArticleBeing Leveraged Means Having Zero Choices

Being Leveraged Means Having Zero Choices

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...

ArticleI Failed. What Will People Think of Me?

I Failed. What Will People Think of Me?

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...

ArticleDon't be Afraid to Take Big Swings

Don't be Afraid to Take Big Swings

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...

ArticleWhen Founders No Longer Have Any Upside

When Founders No Longer Have Any Upside

Just because it's our startup doesn't mean we still have upside in it.

Anyone who's taken on a single round of capital and has suffered the painful dilution that comes with has had the first taste of "reduced upside." We accept it though, like taking awful medicine because we know it'll make things better in the end. But at some point that medicine stops working.

At some point, we look around and realize that our startup no longer provides the kind of upside for us we thought it would. It was easy to overlook when we could see us "making billions" but now reality has set in and we realize we just have a really stressful job that pays us way below market.

Call it What it is

First off, we have to call it what it is — a shitty deal. Is it a sh...

ArticleThe Lies Founders Tell About Retirement

The Lies Founders Tell About Retirement

Retirement is a beautiful lie we Founders tell ourselves.

We fantasize about one day selling our startup, retiring, and living this gifted life that makes all of our sacrifices worthwhile. We see this perfect existence that was only constrained by the shackles of our work and the drudgery that was our startup.

Yet it turns out while it may be a fantasy for us, many enterprising Founders before us have actually playtested this fantasy for real. As it happens, nearly all of us develop some version of the same fantasy and later on come to the same (much more sober) reality.

It turns out, it's really easy to tell ourselves what we're going to do when we retire, but actually doing any of that stuff is harder than building the startup it took to ...

ArticleThe Problem with "Local Advice"

The Problem with "Local Advice"

The worst advice Founders get consistently comes from their hometown.

I call these the "local yocals" and every hometown has them. They are well-meaning advisors who try to guide a Founder through the startup stages but instead fill their head with irrelevant, outdated, and in many cases straight-up bad advice.

Every single time I talk to a Founder that's been clearly led astray, I ask where they got that advice. And in almost every case, it's from someone that simply isn't relevant to the startup ecosystem. It's their well-meaning uncle who made a boatload of money in commercial real estate, or a local angel investor who has no idea who YCombinator is, or the "startup guru" who had the one exit in town but has never left the state.

From a ...

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