Let me start this one off with an admission: 

I ultimately decided *against* raising money for my own startups, and fund my venture studio through the various projects I create & have my teams manage. Before making that decision, I weighed a lot of options, talked to a lot of people, and I’m fully aware that at any moment I can raise whatever amount of capital I need in a matter of weeks.

Let me continue it with the brass tax assessment:

Early stage equity based fundraising only makes sense if you’re creating new, deeply innovative technology that’s expensive to build & test. For MOST other startups, you’re usually better off (in the long run) utilizing debt - venture debt, business loans, credit cards etc. than dealing with all the shenanigans. More on this throughout the article.


Fun fact about me: I’ve been trading and investing in one form or another since I was a kid. When I was 8 years old, I would sell rice krispie treats & brownies when I went camping, turning $20~ of material into $100+ of profit. (Which I promptly blew on food, haha)

One year, some other kids showed me these little pewter statues that they were trading with the merchants. They were about 25 cents each, or 5 for a dollar. Most of the other kids gave up after about 10 minutes, going off to play in the mud or whatever it was they did. Me? I bought a whole bunch of those statues and got to work.

Over the course of a weekend, at age 8 I turned a few dollars into a few hundred worth of stuff. I traded with merchant after merchant, brought a little candy box around with me to show off my own wares, and got a whole host of cool things - a rabbit skin bag, a potato gun, a waterskin… Look, I was 8. What do you want?

Later on, I played a bunch of Runescape and WoW, where I not only ran a bunch of pugs (Server first pug group to kill Deathwing btw - literally walked 30 minutes to the library during a snowstorm to make that happen), I also did a lot of trading and investing in various in-game markets. I did pretty well for myself. Let’s just say that they *literally* had to change a rule or two because of me.

Anyway, the point is: I’ve always been a huge fan of both investing AND trading. Where other people find them complex and hard to follow, I actually find them very simple and easy to understand - and I’m not talking about technical analysis or algorithms, for the record. I’m talking purely about the fundamentals - I’ve always loved figuring out exactly how things tick.

It’s these same tendencies that have led me to build my own projects and look into fundraising for myself. I’ve got to say, speaking frankly: Whenever I look at how other people approach investments, I’m completely fucking shocked.

Y’all be some crazy motherfuckers I swear.

I feel like I see pretty much 4 types of investment talk (All of which I think are complete bullshit, for the record):

1. “Bruh, my startup is the greatest thing that’s ever going to happen in the history of the world! That’s why you should give me 2 years of your life AND 300K!” (Despite having no product, no customers, no marketing campaigns, no knowledge, no team, no anything really.)

2. “Just invest 25% of your money in a 401K until you’re 65 and don’t even question your broker because they know best.” (Are you… Are you actually retarded? Do I need to have you tested? Because I feel like if I need to explain why I feel the need to have you tested, you need to take a retarded test.)

3. “This revolutionary sparkling water brand just raised $200 Mil in just 3 days WiTh No PrOdUcT!@!” (Sure. I was born yesterday and I have an arrow sticking through my skull.)


4. “Don’t even invest. You need to start up a small business feeding semi-aquatic squirrels. They’ll be your greatest customers.” (Newsflash: semi-aquatic squirrels DON’T HAVE ANY MONEY!)

… You get the idea.

Here’s what everyone wants you to believe startup investing looks like from the outside:

Technical genius discovers untapped potential in a new market, and boldly follows his dreams. With nothing more than a hope, a prayer, and a lot of hard work & determination, he finds the first investor who truly believes in him, giving him the first million dollars that changes his entire life - forever.

Here’s what MOST popularized startup investing *really* looks like:

Tech bro invents new form of slavery, shamelessly circumvents laws & regulations designed to protect consumers through an ultimate technique: burning money at a rate that almost feels illegal. After 5 years, 1 out of 10 manages to exit at a 100x valuation - after successfully enslaving half the world’s population.

(Actually I’m not really being harsh enough here - some of these things really got crazier than that.)

And here’s what MOST real startup investing looks like (ie. Not the popular tech bro stuff):

Above average businessman with a decent enough plan and good executionary skills (albeit moderate marketing & business skills) manages to convince an investor to give him just enough money to last until they need to raise funds again in 6 months. He enters into a multi-year cycle that only ends when they either successfully find someone willing to buy the company (usually at nowhere near those unicorn valuations), or they finally exhaust every possible angle and can’t find new investors.


Now the question is: Why does this happen?

I’m gonna let you in on an open secret here. Most startup founders don’t actually know shit about business. (Hell, most entrepreneurs don’t know shit about business either, if we’re being *really* honest here)

Give me all the flak you want here, but I’ve run the audits. You know as well as I do that when you come to me saying “I’ve made a whole 80K this year in gross revenue and kept $5,000 of that!” that you don’t have a real business. (It’s better to accept it - go read the 25K / mo article if you need real, practical advice on changing your situation quickly.)

Instead, *most* startup founders are looking for every possible way that they can avoid putting in the genuinely hard work. The deep levels of thought that require you to confront your own ego and your insecurities. The cold calls that leave you feeling like someone just shoved a spiked dildo down your throat.

The acceptance that you need new levels of skill. The reframing and repackaging of your products and the brutal reality that even if you DID manage to get the funds from an investor, it doesn’t solve the underlying problems that you have.

They think that what’s holding them back is a lack of funds. I’m living proof that it isn’t - I’ve lost track of the number of times I’ve either helped someone else or built & watched a project go from $0 -> $10K+ in profit in 1 month.

So the paradox is this:

You as a startup founder want to get paid for the work you do. In accepting an outside investment from the wrong person, you open yourself up to an entire world of trouble - stock fuckery, bad terms, constant phone calls & meetings, a lot of stress, and (even worse), the lack of a truly functional business in the end. (Because you weren’t forced to figure out how it would actually turn a *profit*)

This is BEFORE we talk about deeper nonsense. Cap tables, investment delays, internal politics, all that jazz. Look, I’ll be totally upfront: There’s so many ways you can get fucked, and this particular area of investing isn’t 100% my area of expertise. I’d hate to tell you guys one thing and then it turns out I’m completely wrong about it.

Just bear in mind that even I don’t even understand all the subtle ways you can get fucked as a founder. I *literally* built a video game with hundreds of cards & thousands of interactions, and kept all of that straight in my head no problem. What does that tell you about what witchcraft we’re dealing with here?

So how do we fix it? How do we break out of this paradox?

Short answer:

Sales & market validation. More on that in the 25K / mo article.

Long answer:

Take a good, hard look at what you’re building. Try and figure out where and how you can cut costs on your prototype, and how you can make do with what resources you have at your disposal. If a man can build a dialysis machine out of some bamboo and a few plastic tubes, I’m pretty sure you can figure out how to build an MVP with a few bucks.

Once you have the barebones framework - not even the prototype, mind you - go to people and just ask for feedback. If they try to give you money, you’re on the right track. If they don’t, switch gears. Either talk to different people, change something up in your product, or move on to something else.

Just by doing this and iterating enough, you should be able to reach $50K+ / month SOLO. If you can’t make that happen, you literally aren’t doing it right. Solo cold calling alone will get you there if you do it right.

IF you have something genuinely big or unique enough that requires investment funds, do the following: Vet your investors thoroughly, build great boundaries, and only accept checks of $100K+.

What, you’re trying to raise $50K from an angel? See above, dummy. Ignore this advice at your own peril.


“Startups are funny. So many of them are broke people pretending they’re rich & uniquely talented, all peddling the latest buzzwords. They do this in order to raise funds from other broke people pretending they’re rich & uniquely talented, also peddling the latest buzzwords. They never seem to realize that they could literally just try selling their thing and get much further, much faster.” ~ Synclair

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