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I often picture this Marty McFly moment where I'm sitting across from my 18-year-old self, this skinny pimply-faced kid who thought he could start an Internet company, and trying so hard to impart the wisdom that cost me decades to share.

It makes me wonder whether there could have been a directional shift if only someone was helpful enough to provide just the right advice at just the right time. It's what I've dedicated my whole life to in helping my fellow Founders, but still, I wonder if I could have helped myself.

If I only had three things I could tell this young fool — what would I say, and how do I think he would have taken it?

Lesson 1: "You have 50 Years"

I never realized how much time you really have to make an impact. When I was ...

Continuing in Phase One of a four-part Funding Series:

Phase One - Structuring a Fundraise

• Part 1 - Startup Bootstrapping

• Part 2 - Debt as Startup Capital

• Part 3 - Equity Funding for Startups ( ←YOU ARE HERE 😀)

• Part 4 - Convertible Debt

Phase Two - Investor Selection

Phase Three - The Pitch

Phase Four - Investor Outreach

Let's dive in!

Pursuing equity financing means that, in exchange for the money they invest now, angel investors or venture capitalists will receive a stake in your company and its performance moving forward.

Equity financing is one of the most sought-after forms of startup funding for entrepreneurs, although certainly the least available (compared to something like a business loan or friends and family financing). Simply put – there...

Founder: The person who started the company. It is someone who has an idea and creates a business around that idea. They are the “Founding Father” or "Founding Mother" of the company, as the company would have never existed without them creating it. They are often focused on vision and big picture of the start up. They are generally the business owner, or at least one of them.

CEO: The head of the company, responsible for overseeing all aspects of it and making sure everything runs smoothly. The Chief Executive Officer runs it as a business, sets the long term plans and drives towards success. They also communicate directly to the board of directors. A Professional CEO will have the distinction of having risen through the ranks, and brings ...

“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...

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...

Founder success is almost never what we picture it to be.

When we think of wildly successful Founders our minds easily jump to billionaires like Branson, Blakely, and Musk, balancing a life of magazine cover story photoshoots with keynote presentations and TV interviews. Our most "successful" Founders often have this air of glamour around their success.

But as it happens, Founder "success" feels way less glamorous. In fact, the most exciting success milestones are often so mundane when they occur that we don't even realize they happened. But this success is a culmination not of a single event, but a series of tiny events that we later look back and realize was when our success was truly defined.

We Always Make Payroll

For most of our journ...

The worst time to get tired in a race is at the end.

Now, imagine we've just run a marathon (it's called a startup) and at the very end of that marathon is the finish line (it's called an exit), but we're too tired to make it across. Can you imagine a worse time to be out of energy than the moment where we're just about to win the race?

Yet many Founders, by the time we get to our most important milestone (the sale), just have nothing left. So we capitulate. We agree to silly terms, or unrealistic expectations, not because we think it's a good deal, but because we just want to be done with any deal. We're incredibly vulnerable, and that's incredibly dangerous.

"But I Just Want to be Done With it!"

Look, I get it. By the time we're teeing up...

Being a Founder is a job that anyone can get and no one is qualified for.

My 9-year-old daughter became a Founder last year within 60 minutes of forming her own company online (she didn't even need my help). I'd argue she's about as qualified as most of the Founders I meet at Startups.com, and that's not a knock. It's to say that none of us are "qualified" to be a Founder, not because we're not smart enough, or capable enough, or experienced enough — it's because fundamentally it's impossible to be qualified for this job.

We Can't Be An Expert At Everything

The difference between a Founder leading a startup and a CEO leading an established business is that the Founder has to be there from the start when no one else is there. That means the...

In 2008, the world got a new music streaming service named Spotify. It was developed in Stockholm, Sweden, and provided digital rights management-protected content from record labels and media companies. It may have started out as a local thing, but the freemium service quickly expanded. Today, Spotify has more than 140 million monthly active users and over 50 million paying subscribers.

I had the pleasure of meeting up with Andreas Ehn, who was Spotify’s first employee and CTO. Andreas was responsible for the product and platform architecture as well as hiring a world-class engineering team, of which many have gone on to become successful entrepreneurs on their own.

After Spotify, Andreas founded Wrapp — a mobile online-to-offline customer...

A Founder that doesn't understand startup finance is a liability to the company.

The very survival of a startup comes down to whether we have enough cash to survive. If the Founder can't answer that question, it'd be like hopping on a jet with a pilot that doesn't understand how to read the altimeter, compass, or fuel gauge. They might be a great pilot, but without knowing the fundamentals, that trip is going to end poorly.

Fortunately, Founders don't need an MBA in finance to be competent, we just need to understand a few basic principles very well. While I'm the Founder + CEO of Startups.com, I'm also our CFO. That's because I learned long ago that with a solid understanding of just a few key principles, we can make (and avoid!) really cr...