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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 ( ←YOU ARE HERE 😀)

• Part 3 - Equity Funding for Startups

• Part 4 - Convertible Debt 

Phase Two - Investor Selection

Phase Three - The Pitch

Phase Four - Investor Outreach

Let's dive in!

Debt is the most common form of outside capital for new small business owners. While angel investors and venture capitalists get all the big headlines for funding exciting companies, it’s the debt providers that are behind most of the investment dollars that go into the 99% of companies that aren’t splashed across magazine covers and business websites. SBA Loans, Personal Loans to the business owner, merchant ca...

Welcome to Phase One of a four-part Funding Series:

Phase One - Structuring a Fundraise

• Part 1 - Startup Bootstrapping ( ←YOU ARE HERE 😀)

• Part 2 - Debt as Startup Capital

• Part 3 - Equity Funding for Startups

• Part 4 - Convertible Debt 

Phase Two - Investor Selection

Phase Three - The Pitch

Phase Four - Investor Outreach

We are excited to guide you on your funding journey. Let's dive in!

Bootstrapping involves all sorts of capital — friends and family, your personal savings, crowdfunding, and of course the ever-popular "sweat equity" (getting people to work for stock in your company).

Bootstrap Meaning

Contrary to what many believe, most businesses don't get started by way of a big investment from some deep-pocketed investor. Most businesses get sta...

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 ...

In a time where lots of people are announcing staff reductions left and right, it's a good time to talk about the most important aspects of dealing with the human element of reductions — Ego and Safety.

When I was a younger manager just learning how this all worked, I didn't understand the value of Ego and Safety. My "fires" turned into heated outbursts, crying, and grandstanding. I couldn't figure out what was going on and assumed these blowups were tied to the people I was letting go.

They weren't — it was entirely my fault. Even though I tried to be kind, I didn't appreciate that letting people go isn't about the transaction — it's about the person. How we manage that relationship is the transaction, and it always maps back to how we vie...

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...

What if no matter what we do, our anxiety never goes away?

We all want to believe that the relief from whatever is stressing us out is just one milestone away. If we could just raise this next round, or get the product shipped, or get to profitability — we'd be able to breathe easy.

It doesn't stop there. We believe if we just make enough money, meet the right person, or finally buy that one thing then we'll be "satisfied" and all that anxiety will melt.

But what if it never does? What if all of our achievements keep bringing us right back to the same point — and we can never figure out why? Can we really "out achieve" our anxiety?

I Tried It — It Didn't Work!

Let me tell you Founder friends — I tried it. I started this game with a boatload...

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...

We spend most of our time living in terror of things that never come to pass.

I call these "Paper Demons" because they are shallow, flimsy evils that we make up in our heads but somehow pretend they are entirely true. It's the many awful fates we consider of our startups and our careers if things go wrong or the knockdown, drag-out arguments we're going to have with investors if we crater this thing.

Our Paper Demons come in many flavors but they all share one trait — they are imaginary outcomes that we treat as if they are absolute. The problem with this thinking is that it consumes an insane amount of real energy and focus, which, ironically, is exactly what we need to conserve in order to avoid those fates.

My Investors Will Revolt!

Ah y...

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...