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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...

Most startups launch with $0 in funding, but no one ever really explains how the hell they do it. We keep saying, "They bootstrapped it," as if that explains anything other than "They didn't take on investors." What the heck does that even mean? What it is intended to mean is that we find creative ways to compensate people and buy things that don't involve using cash in the bank.

We can't possibly cover every use case of how startups find resources for $0, but let's take a look at the most popular categories that people run around looking for money for and see how we make it work.

Paying for People

Figuring out how to compensate people is where we're often stuck first. Most of us are familiar with paying folks with equity, but that's not th...

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...

There is a ton of hidden treasure in failed startups — you just have to know how to look for it, and ultimately, how to capture it.

After my first (not last) venture-funded startup tanked, everyone pretty much ran for the hills. Investors bailed, the team got other jobs, and customers found better solutions. But I kept thinking "We just spent a ton of money to build all of this, can't I capture this value back?"

Then it occurred to me — the same thing is happening for countless other failed startups. All of the assets that they spent millions to build just get buried. Everyone tries to make a last-ditch effort to sell them off, but in most cases, it never works and they just evaporate.

But what if we were the ones looking to dig up that bur...

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...

Here's a crazy idea — what about a startup that just makes money?

I know, I know — crazy talk! But it turns out that while 1% of the startup world is busy chasing venture capital and trying to create outsized returns, 99% of the rest of businesses are just trying to build a business that consistently turns a profit.

"How dare you question the wisdom of VC!" — echoes the startup world.

But seriously, it turns out even grizzled veterans of the startup world, especially those who have raised venture capital before, are getting really excited about building companies that guarantee a profit versus potentially generating an exit.

What Happened?

It's a confluence of factors, really. When the Nuclear Winter of Funding hit in 2022 and beyond, an aw...

The startup world is all about moving fast — but at what expense?

We've built this narrative for ourselves within startups that we're constantly under the gun to move quickly or else. If we don't move quickly, we won't attract more funding, we'll lose ground to all of our competitors, and we'll be perceived as being "slow," which is considered the death knell for any respectable startup.

But what if all of that is bullshit?

What if there are real costs to moving too quickly that will far outweigh whatever perceived benefits we're told we're getting? We stand to lose a lot if we invent a false notion of urgency that prevents us from making good decisions for the long term.

Pleasing the Wrong Party

Let's start with who we're moving fast for. ...

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...

When times are good at our startups, we think it will never change; when times are bad, we think it will never change.

Yet the only constant with startups is change.

The challenge for many Founders is that this is likely the first time we've had good or bad times, so we have yet to see a full cycle. That makes it difficult to know whether this is a short-term blip or a long-term trend. As such, we tend to grossly overcompensate by spending too much in good times and running for the hills in bad times.

How Startups Actually Grow

We all have this fantasy that our startups constantly grow "up and to the right!" on our beautiful charts. The reality is way different. The best way to think about our startup journey is a constant cycle of "feast o...

What if I told you that selling a company for $40 million could net you more money than if you sold it for $200 million?

On its face, it sounds ludicrous, I know! But what's missing in that formula isn't the exit price, but how much of that exit we get to put in our pocket as we raise more rounds of capital.

More importantly, our opportunities to sell for $40m are dramatically more abundant than selling for $200m (or more!). That means every time we raise capital, while it sounds like we're improving our chances of an outcome, we're also reducing our options to find an exit at all.

Real Founder Dilution Numbers

CapShare released a study of 5,000 startup cap tables to determine how much equity Founders have at each stage of a funding round. ...