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

It’s selfish, and here’s why

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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)

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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:

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.

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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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Photo by Kyle Glenn on Unsplash

“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…

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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…

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Can you see the hidden message? Share what you see in the comments

Make sure it sends the ones you want

The design of your cap table sends messages both to future employees and to investors. It’s unavoidable.

There are obvious messages, like:

  • Which founder wears the pants in the relationship?
  • How generous were the founders in distributing equity?
  • How disciplined have the founders been in fundraising?

Plus many more, interesting psycho-analysis questions you could derive from how the cap table is split.

A plethora of articles have been written on this topic, and I do not intend to add to them.

My intention with this article is to discuss the optics of the actual design of your cap table. I…

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Photo by Chris Liverani on Unsplash

An end-to-end guide on the undeniable power of the Conditional Close, with strategy, rationale, and examples to give your startup momentum

One of my best friend’s name is Cache (disguised), and one of my favorite things about Cache is what we call “Cache Bets”.

A Cache Bet is a spontaneous bet initiated by Cache, on a ridiculously stupid yet entertaining premise at very low-risk terms, often for nothing more than the pride of proving the person who bet against him wrong. Examples of some of our favorite Cache Bets include:

  • Betting he could avoid getting hit by a roman candle (he succeeded)
  • Betting he could jump 1/2 up the stairs of a friends cement stairwell (he failed)
  • Betting he could run…

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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