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Some investors may be considered "angels" — but they are no saints!

That's why when it comes to getting "bailed out" by future investors, whether it be compensating us personally for money we've lost or helping to get our startup out of debt, we're entirely on our own. We've helped thousands of Founders raise capital, and invariably, many ask whether new investors would be willing to cover their previous losses or investments. The short answer is "absolutely not." But the longer answer may help you understand exactly why.

What Debts Are We Talking About?

The most common debts Founders ask about are personal debt they've created in financing the company or forgone compensation. The question often looks like, "I've put in $100,000 of my own m...

Venture-funded startups grow way beyond their means because they have to.

Time and time again we get asked by (typically bootstrapped) Founders about why in the hell venture-funded startups love that so-called "fake growth."

You've seen this before, when a new startup raises gobs of venture capital, hires hundreds of new people, burns through tens of millions of dollars (or more!), and then later on has to crash and burn the whole thing because it never actually made any money.

From the outside, it seems insane. What Founders don't realize is that this whole "fake growth strategy" isn't just some bizarre misstep - it's an actual playbook. We look at stories like WeWork and ask "How could anyone let that happen?" Well, it turns out, there's...

There's a reason the only way to get the "Founder" job title is to start the company — because there's no way to hire for it otherwise.

When I was running my first company, I was in my mid-20s with a hilarious lack of experience. The company was growing quickly, and we went from "a few people in a room" to "a few hundred people in a room," and soon my lack of experience (and pimples) was becoming very evident.

I was scared, so I set out to find a replacement for me, someone who could not only bring more experience but more confidence to the staff in executive leadership. We found an "old guy" who, at the time, I think was maybe 38, probably less, but he had some gray hair and was orders of magnitude more mature than the lot of us.

Try #1: C...

TL;DR: "Oh Sh*t!! My competitor just raised a bunch of funding to do exactly what we're doing. We're done for, right? How can we possibly compete with someone who now has the resources to do all of the things we wished we could do?"

Yes, a competitor just raised some funding. No, it probably doesn't matter.

"Wait, what? How could my competitor raising money be anything but my own personal Armageddon?"

Well, it turns out that when the pixie dust settles after those big announcements, our competitors often have a whole new bag of problems to deal with that we don't. We need to look past the upside of that new capital to understand how most funded startups actually sink themselves with an anchor of funding.

All Fat and Bloated

The very first t...

Forget Snapchat. One of the most speculated about potential IPOs in Silicon Valley this year is file sharing and storage company Dropbox.

Dropbox was one of the earliest Valley unicorns to seem to defy any logic in valuations, and at its last round was valued at $10 billion making it one of a handful of so-called “deca-corns.” At one time, it and Airbnb made up some 95% of the value of Y-Combinator’s entire portfolio. And it was backed early on by top venture capital firms Sequoia Capital, on their way to raising some $600 million in capital. Its office was so lavish it reportedly spent up to $40 million a year just on employee perks. Its lobby sported a $100,000 statue of a Panda.

Yes, for a while, Dropbox and its co-founder and CEO Drew H...

Every good startup dies a thousand deaths before it ever lives.

We don't like to believe that because it sounds awful. Who would get excited about doing anything that sounded like it was going to die a bunch of times? Yet death — in the form of setbacks, restarts, and in some cases implosions — is kind of what we do for a living as Founders.

Pretending like we're going to get through this whole thing unscathed is like picking up a video game on the hardest setting and thinking we're going to beat the entire game without ever losing a life. It just doesn't work that way.

So just like our blinking Super Mario coming back to life for the 1,000th time, we've got to learn how to play through the whole game while pretty much expecting to lose a f...

The only product that makes sense right now is the one that makes dollars.

We all want to believe that in the formative days of a startup, all we should be building is the exact product vision in our heads. We should be turning a blind eye to anything that doesn't directly contribute toward that vision. Everything else is a distraction... right?

While that does sound wonderful, it's not only rare, it's also somewhat delusional. The reality is most startups (who aren't funded) need to focus on building stuff that makes money, regardless of whether it's directly contributing to the product vision. And guess what? Sometimes that winds up being the best product investment we can make.

Money = Runway

Let's start with the obvious — we need to get...

Every single time I look up the value of the AOL Time Warner merger it shocks me. And I’ve covered this industry for nearly 20 years. $350 billion. The biggest merger in history, at the time. Steve Case– the man who was the architect of it, who stepped aside from his CEO job in order to make the deal happen– is not surprisingly a man who got used to be considered crazy.

It took AOL seven years of evangelism and partnerships to get to some 200,000 customers and an IPO of some $70 million. When the company started, it was illegal for commercial entities to be hooked up to the Internet, only 3% of the country was online, and Sears was one of the most innovative Internet pioneers. Sears!

The story of the early days of AOL as told to us by Steve...

To say that Rand Fishkin is the ‘Godfather’ of the SEO industry may not be technically true, but it kind of feels that way.

He’s been a thought-leader in the digital marketing and search space since as long as I’ve been in the game (12+ years for me which is an eternity in anything digital these days), so if there were a Mount Rushmore of SEO (or digital marketing), he’d probably be on it.

He’s been showing people like me how to slay the dragon that is Google for years, and lots of folks owe their ability to have careers in the digital marketing space directly to his efforts.

Not only that, but he also Co-Founded a pretty well-known SaaS company called Moz along the way (with his Mom I might add), and built it into one of the best and most ...

The startup world is in a "Silent Recession" that no one is talking about, and it's a real problem.

Most of the Founders I speak to in private say the same thing — their business isn't going well. It's a combination of a weird economy, a Nuclear Winter in startup funding, and sky-high interest rates. Economists can tell us that the stock market is at an all-time high, unemployment is down, and inflation means people are spending too quickly. Yet if you talk to enough Founders honestly, they will tell a very different story.

If you're at a point where you're trying to understand why things aren't quite going as well as they should, let me shed some light on things my friends. We're in a Silent Recession among startups, where secretly they ar...