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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 decided I should pursue the idea full time. …

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.

Instead, I believe “tenability” is a better metric to gauge the intrinsic value of an idea. …

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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 get your job done, deliver value, and take whatever time off you need to take care of life and your mental sanity. …

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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 wounds don’t feel quite as fresh and I’m ready to share a few thoughts from that experience. …

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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 getting ourselves in to. The ugliest parts of starting a startup are by far the legal and tax aspects. But people rarely talk about them, and nobody hands you a “how-to” guide when you decide to start your business. …

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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 share three interesting questions that will play a tangible role in your company’s future (at least they have in mine) and took brain cycles to correct or resolve. …

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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 across 1/2" thick ice at Bear Lake in the winter (he…

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Photo by Stephanie Klepacki on Unsplash

Investors have one of the most intense cases of FOMO you can imagine — it’s your job to change their narrative

Call me jaded, but I’ve long since given up on believing people when they say “maybe”.

Whether it’s asking a colleague if they want to meet up for lunch, asking your in-laws if they want to watch your kids this weekend, or asking for an investment, “maybe” just means “no” (or for the “optimistic”, not right now).

“Maybe” is a cover for people who are either too uncomfortable to communicate or too afraid to commit to a “No”

When I went through the fundraising process with my first startup, I pitched over 100 investors/investor groups. I had the opportunity to pitch some pretty big names, and never having gone through the process before, I often got excited when we had a favorable interaction and a response that could be classified as “maybe”. …

Otherwise, nothing happens

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Photo by NeONBRAND on Unsplash

Early in my time at McKinsey & Co, working with one of my clients on a quick 6 week, high impact project, I had a brilliant idea.

I was so proud of the idea, I immediately sent my manager an IM (Lotus Notes messenger anyone?) with the high-level details. He immediately responded with:

“Genius! Now go write it down on a slide. Nothing happens at McKinsey unless you write it down.”

I found his response incredibly annoying. …

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An end-to-end guide on the power of Forwardable Emails, with strategy, rationale, and examples to help build your unfair advantage

I’d just started Techstars in Kansas City, 2017. I was hyped up, stoked beyond belief to be part of this incredible network, drinking the Techstars Koolaid and loving every gulp.

We were listening to David Cohen talk to us about fundraising tactics over Blue Jeans video conferencing when he spoke the words that changed my life forever:

“… and then once you get a response, offer to send them a ‘forwardable email’…”

My ears perked up. “Forwardable email”? I’d never heard of this concept before, but it sounded intriguing. …


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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