The complete fundraising guide, with strategy, rationale, and examples to help build your unfair financing advantage

Let’s be candid.

Fundraising is damn hard.

Especially as a first-time founder.

My first time, I pitched over 100 investors. I flew from California to Charleston, from Chicago to Austin, trying to find the right investors.

It took 6 months of full-time effort, sometimes having up to 10 different video conference calls or in-person pitches a day. My days were full of investors telling me why we weren’t a good fit, and me continually refining my approach, trying to find that fit.

But hard does not mean impossible.

It requires concentration, organization, and a ridiculous amount of grit to get…

It’s the investor version of “It’s not you, it’s me”, and a cover for the real reason

While fundraising, particularly for first-time founders, it’s not uncommon to hear the following phrase from investors when they pass on your investment opportunity:

You’re too early

However, in my experience, this isn’t really a reason. Rather, it’s a red herring that feels like an acceptable reason to turn down an investment, yet serves to functionally hide the truth — which may be harder for an entrepreneur to hear or more difficult for the investor to communicate.

Justification for “Too Early”

Usually “too early” is combined with an “explanation” such as:

  • I’d like to see more customers
  • I’m curious to see how the market is…

4 next-gen banking tools you can start using today to improve your finances

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If you have cash sitting around (i.e. not in an investment account) that isn’t earning 10% interest annually, today is the day to change that.

How, might you ask? It’s all made possible via defi and crypto lending. If you’re new to the space, I have another article coming shortly to explain the basics, and I’ll link it here when it’s available.

In the meantime, this article will cover the following:

  • How to earn >10% interest on your cash
  • Blockchain + traditional bank = The future bank
  • How to trade crypto like a pro without doing anything
  • How to access…

The visual “get smart fast” guide to understanding your options and key questions you should be asking

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We’ve been hiring a lot lately for our companies, Learn In and BookClub. One of our founding principles is to bring people on who are aligned to our mission, and one way to help do this is by offering stock options as part of every compensation package.

Many of these amazing people have never worked in a startup before, and haven’t had to deal with stock options. As such, they have a lot of questions trying to understand them, what exactly they’re being granted, and how exactly they work.

Options are complicated. After 7 years of dealing with them, I…

Learning how/when to employ “Top-Down” v. “Bottoms-Up” communication styles is a priceless skill that will pay lifelong dividends

Supervillains want to be understood, even if it’s just the hero right before they supposed to be destroyed.

We all have an innate desire to be understood. There’s a reason supervillains are known for monologuing — they want someone to understand the genius of their brilliant plans.

In real life, a similar phenomenon occurs in communication where people believe it’s critical for others to understand the context of a situation prior to delivering the punchline. They want to be understood before they get judged, so they’ll provide explanations and details for their actions before sharing what actually took place.

In my perspective, the reason for this is people want to convey something like “If you had been in…

Figuring out what to do next depends on your physical and mental energy

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I recently had a conversation with a first-time founder whose tech startup was on its last breath. She could see the writing on the wall and was trying to decide what to do next.

She had a handful of concerns she wanted to discuss, among them feelings of inadequacy and worry about not having the attractive resume line she was anticipating she’d have.

A big part of informing the decision of where to go next has to do with unpacking an individual’s mental and physical state.

The mental state

The first thing I wanted to highlight was

Just because a business failed doesn’t…

It’s selfish, and here’s why

As a pragmatic utilitarian with a lean process-oriented mindset, there’s much for me to love about the FIRE movement.

I love that it advocates for people to take an earnest look at their wants and needs and figure out every opportunity to eliminate waste.

I love that it encourages people to live within their means — to minimize expenses and increase income — thereby maximizing their net income and encouraging people to save/invest a majority of their earnings.

I love this fundamental focus on saving and conservation over spending and accumulation.

However, I believe there’s a fundamental flaw with FIRE.

The key is determining where to flex (hint: use the Triangle of Constraints)

When I was a kid, we had this huge golden retriever named Chance. Even though he was a bear of a dog (he weighed over 90 pounds), he had a relatively small mouth. As such, one of my favorite things about Chance was watching him try and fit three tennis balls into it.

He could pick up the first two without any issues but try as he might, he was never quite able to get that third tennis ball in. As soon as he put his head…

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And answering the question “When is the right time to quit”?

The idea for my first business came to me in January of 2014. I was working with my 6th manufacturing client at McKinsey, and realized the fundamental behaviors driving the problem we were there to solve mirrored the previous 5 companies almost to the “t”.

My engineering brain went into overdrive, and I began thinking of what a technology platform would look like that could both address and improve those behaviors.

As the idea took shape in my brain, I pitched it to 2–3 friends at the client and received extremely positive feedback. This feedback was enough that I immediately…

Determine if a business idea is worth pursuing by evaluating “tenability” v. “competition”

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There’s a simple framework I’ve found helpful to work against when evaluating a new business idea — specifically when trying to answer the question:

“Is this idea worth pursuing?”

I use the axes of “tenability” and “competition” to provide an insightful evaluation of the idea.


The first question, and perhaps the most natural one, is “Is the idea tenable?”

I used to think of it in terms of “good idea” v “bad idea”, which tends to be a quick way to react to new ideas. But sometimes the best ideas come from the ones that started out as terrible ideas.

Jonathan Woahn

Chief of Staff @ The Future of Work Studios. Husband. Father. TFA. McKinsey & Co. 3X startups. Entrepreneurship, leadership and self-actualization enthusiast.

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