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.

Tenability

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.


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This phenomenal perk has a dark side. Use the concept of ‘loss aversion’ to fix it.

Unlimited Paid Time Off (UPTO) has become the quintessential hallmark of tech startups. This amazing perk representing the ultimate “I trust you” signal from an employer.

At face value, it seems pretty incredible. No limit to the number of days you can take off? You mean I don’t need to carefully track and strategize how to use my days off? I don’t need to accrue days over the year so I can have enough time to take that vacation with my family?

Nope, no limit. You’re an adult, we want to treat you like an adult. We trust you to…


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“Failure is a great teacher, and, if you are open to it, every mistake has a lesson to offer.” — Oprah

It’s been over a year since I left my role as CEO of my first startup. Things were fine, but it wasn’t growing as quickly as I’d hoped. After 5 stressful years of 80+ hour weeks, I lacked the physical, mental, and emotional zeal to keep going. So instead of forcing myself into year #6, I chose to step down and leave the job to better, fresher minds.

Enough time has passed now that the scars from my emotional…


Starting a business is all fun and games until the IRS and legal work get involved. Then it sucks. Best know what you’re getting into.

In the summer of my second year of college, I started an IT consulting business with a good friend. Given we were both IT experts, it seemed like a great idea.

Problem was, neither of us had started a business like this from scratch. It was an eventful ride, but the TLDR version is due to our inexperience, the IRS believed we owed $60k in taxes.

It took 2 extremely painful years to convince them we didn’t (the business went belly up, and we lost money).

The entire debacle could have been avoided if we’d only know what we were…

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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