I help people start, finish, and ship creative projects.

Sign up below to receive exclusive, weekly updates.

instigate. inspire. lead.

For a more in depth look at building a team and shipping a product to market, get my new free (for now) 7 week course. Sign up here.

On 16 October, 1890, in a small farm off the windswept southern coast of Clonakilty, County Cork, Ireland, the leader of the Irish Revolution was born.

Of course, no one could predict this at the time, but like all history: it now seems inexorable.

The youngest of 8 kids, Michael Collins didn’t grow up with a lot of money, but what his family lacked financially his parents made up for with an intense focus on education (it would come to serve him well in the future).

At the turn of the 20th century, when Michael was in his teens studying hard and working a full-time job, hoping for a better life, Irish-British relations were hitting a tipping point.

For hundreds of years prior, the Irish faced subjugation and enslavement at the hands of the British (in fact, the first slaves sent to America were Irish).

At the same time, Irish nationalism was on the rise with underground national pride movements happening around the country.

Michael found himself swept up in the movement at a very young age.

Eventually, he became its leader.

From 1917 to 1921, Michael organized, managed, and led an outnumbered, out-financed, and outgunned revolutionary force against the strongest empire in the world.

And, against all odds…

He won.

What Fighting a Revolution Can Teach us about Business in the 21st Century

The secret to Michael’s success wasn’t in vision, charisma, or leadership (although he had all three), but in the genius management and operation of a guerilla force.

While you might not be leading or managing your own revolution anytime soon, these lessons are no less effective for starting a business, managing a remote team or leading multiple collaborative projects.

Let’ get to it:

#1. Set and Focus on One Goal

Before Michael ever took over the reins of the revolution, the objective was clear: freedom.

Of course, what does “freedom” really mean? What does it look like? How do we know we’ve achieved it (or lost it)?

If the framing of these questions feels familiar, they should.

This is the same thread that runs throughout the Lean Startup technique I talked about last week and how to properly analyze the success or failure of an operation so you know when (and how) to pivot.

To run a revolution (or a business), we need to focus on one specific, clear objective or goal.

Further, this goal must be measurable (which means we need to define what metrics we use to measure success).

For Michael, this meant defining freedom for the Irish (an independent Irish state).

The measurement was simple (certainly not easy): that Irish citizens could govern and lead themselves, free from British rule.

Applying the “One Goal Method” to Your Business

I had the pleasure of connecting with Corbett Barr of Fizzle.co last week in San Francisco. During our happy hour meetup, I asked him: how do you run and operate Fizzle.co? Specifically, how do you know what to focus on to succeed (and how do you define that)?

His answer was priceless.

Over at Fizzle.co, the team focuses on themes.  Each theme lasts about 3 months, and is further broken down into 3 week execution phase (build, deploy, evaluate).

One of their recent themes: customer success.

They wanted to make sure every Fizzle member was succeeding, so they focused their time and attention for 3 months on this problem set.

The beauty of this methodology: it keeps the team focused on one goal, one objective. It also helps teams avoid getting sidetracked or focusing on low value activities (sure, a new widget would be good for X, Y or Z, but does it pertain to customer success? If no, scrap it).

Why 3 months?

“It just works.” – Corbett Barr

#2. Lead by Parameters, not Pinpoints (The Flying Columns Technique)

Fighting a revolution against the world’s strongest empire when they’re literally in your backyard is a pretty overwhelming problem set.

Traditional military strategy and tactics call for hierarchy and direct control; standardization of systems, processes, and protocol; large force movement and conflict.

On the surface, these seem like good attributes – most enemy forces would try to fight in like-kind…

Michael saw them for what they are – weaknesses:

  1. Hierarchy and control means inflexibility and slow decision making
  2. Standardization means little or no growth, learning, or improvisation
  3. Large force movement and conflict means slow reaction time

In order to exploit the weaknesses Michael saw in his opponent, he developed (or rather, let develop and then leveraged) what became known as Flying Columns.

These were independently organized and operated fighting forces that could do everything the British Army couldn’t;

  • move fast
  • attack and withdraw quickly
  • adapt to the local battlefield

Of course, the nature of such organic, independent units meant that Michael had to find an unorthodox way to lead and manage his troops (otherwise the whole thing would quickly unravel).

His solution: give his units broad but clear guidelines and the freedom to operate within those guidelines (for example: only attack military personnel; focus on small patrols so the wins seem bigger, etc.).

A pinpoint is a point on a map marking a precise location or target; there’s no room for flexibility around the order (“do this, nothing else is allowed”)

A parameter is a set of guidelines that establish what we call in the Army “left and right” limits; it allows for freedom and flexibility but maintains alignment with mission (“don’t do this, anything else goes”)

Most people think the only way to lead is through pinpoint.

Michael chose parameters.

Applying The Flying Column Technique to Your Business

I run a number of collaborative projects with multiple team members.

Most recently, the Bootstrapped team shipped issue 2.

This is an entirely remote team so classic management strategies don’t work.

I don’t have “eyes on” the people who work with or for me. I can’t know what they’re doing or how they’re doing it.

So I don’t even try.

Instead, I make sure we’re all focused on the objective (see #1 above) and I give parameters for how to create / test / ship etc.

A couple examples of parameters:

  1. Quality over margin (if the question comes down to what we should develop, the focus should always be on quality at first without going into the red)
  2. Relationships over sales (building relationships with readers and subscribers is more important than the initial sale)
  3. Learning and growth is always most important (self explanatory)

Like Michael’s flying columns, these guidelines or parameters (or “left and right” limits) allow me to manage multiple teams spread out across the world (in my case, internet helps a lot).

Yes, you’ll have things built different than your original vision but, if you have the right team, that’s a good thing.

#3. Spread Resources Evenly (the 1/N Strategy)

If you think guiding and directing multiple autonomous units across 32,000 miles of terrain (with no modern perks like cellphones or email) is hard, consider arming and supporting them.

Michael’s primary job, besides intelligence and designing and developing the battle strategy, was logistics.

He had to make sure the revolutionary forces had weapons, ammunition, food etc.

And he also had to make sure no area was without resources to maintain the fight.

It would be very easy to ignore certain parts of the country that were harder to reach, but Michael knew that, in an uncertain, highly unpredictable environment, in order to increase the likelihood of success, he had to spread his resources evenly.

Here’s why this makes sense from a mathematical perspective (excerpt from Antifragile by Nassim Taleb):

the right policy would be what is called “one divided by n” or “1/N” style, spreading attempts in as large a number of trials as possible: if you face n options, invest in all of them in equal amounts. Small amounts per trial, lots of trials, broader than you want. Why? Because in [extremely volatile environments] it is more important to be in something in a small amount than to miss it. As one venture capitalist told me: “The payoff can be so large that you can’t afford not to be in everything.

How to Apply the 1/N Strategy to Your Business


  1. Instigate and ship a lot of products.
  2. Keep your time, effort, and money investmentment in each equal

Focus too much time, effort, and money into one project (before product/market fit) over another and you increase fragility and decrease probability of success.

*Counter-intuitive and contrary to common advice that tells people to focus on one thing only, but statistically it’s the best strategy for survival. And entrepreneurship is all abut survival.*

For more on antifragile businesses, click here.

Wrapping Up (plus new free course)

There are three major lessons we can learn from the Irish revolution – lessons we can apply directly to our businesses today:

  1. Focus on One Object (The One Goal Method)
  2. Set Parameters, not Pinpoints (The Flying Columns Technique)
  3. And Equally Invest in Multiple Projects (1/N Strategy)

I hope you enjoyed today’s blog post.

If you did, I’m creating a 7 week course on how to develop, lead, and ship collaborative projects.

What you will learn in my FREE 7 week course:

  1. How to create a simple, effective business plan that allows you to approach your project the RIGHT way (and avoid major mistakes along the way)
  2. How to validate an idea before you put your team together (so you don’t waste your time or your teams time)
  3. How to find and recruit talented rockstars with complimentary talents to you (so your project becomes a 1000% better than you could do alone)
  4. How to organize a team (focusing on remote organization…i.e. how to run a business from a beach while sipping mojitos…or BinTang)
  5. How to deal with formalities like business contracts and structure
  6. How to MANAGE the development of your product or service (I’ll take you inside the systems and processes I have set up in all my businesses…I’ve never seen anyone share this type of info before, so I hope you find it useful)
  7. How to co-launch your product or service with a big ass launch.

And much more.

>>> I’m giving it away free for early subscribers (but I may charge for it in the future).

So get it while it’s hot: Sign Up Here.

* * *

I hope you enjoyed today’s post.

If you did, please SHARE IT!

Or for the incredible lazy people in the audience (guilty), here’s a click to tweet [CLICK HERE].

Started in San Francisco (at Four Barrel coffee), finished, and shipped in Redmond, Washington.

Writing time: 6:10 hrs

Soundtrack: Geographer Radio on Pandora


Last month I got an email from a friend.

After 6 months of hustle, she’s throwing in the towel.


  • Not enough sales.
  • No traction.
  • No growth.

I felt bad.

I hate seeing people fail.

I hate it even more when a project fails that hasn’t  been properly tested in the marketplace.

In my friends case, she had only tried one option.

It didn’t work.

Surely there’s a better way…

Only the Strong Agile Survive

Granted, not all projects are worthwhile.

Some simply aren’t economically viable.

Is your project economically viable? If not: Pivot!

Others might be able to sustain themselves through whatever means (force, trust fund, etc.), but to what end (the excruciatingly slow death of the postal service comes to mind)?

But the reality is: you can’t know whether a project is worthwhile from the first failure (not if you want to eventually build something that lasts)

So I told my friend that she shouldn’t shut down just yet.

Instead, she should pivot.

The Lean Startup Pivot

What’s a pivot?

Taken from Eric Ries’ book The Lean Startup, a pivot is a:

structured course correction designed to test a new fundamental hypothesis about the product, strategy, and engine of growth.

Good, but a little technical.

Here’s how Steve Blank describes it:

“Pivoting” is when you change a fundamental part of the business model. It can be as simple as recognizing that your product was priced incorrectly. It can be more complex if you find the your target customer or users need to change or the feature set is wrong or you need to “repackage” a monolithic product into a family of products or you chose the wrong sales channel or your customer acquisition programs were ineffective.

In simpler terms (hopefully without missing the point):

A pivot is adjusting your current approach to a problem.

Note: read all the way to the bottom to download The Essential Pivot Checklist and Workbook for when you’re ready to pivot your business or project.

Sometimes it’s a complete overhaul, identifying a new “job to be done” (the pain point you’re solving for people), sometimes in an entirely new industry or via a different medium.

Other times, it’s not so dramatic – just a simple shift in execution.

Every successful company in the world has pivoted at some point in their lifecycle. It’s inevitable.

Pivoting in business.

How do I Pivot?

After I told my friend she should pivot, she asked a reasonable question:


My friend wanted me to tell her what to do in her particular situation.

Here’s the problem:

By its nature, pivoting is a creator-led process.

It requires the owner / operator to think, engage, challenge, test, break and build.

Nobody can tell you how to pivot, nor can someone do it for you.

So, instead of telling her what to do, I suggested some resources that could provide a framework for her to approach the problem. At the same time, I realized that most people have no idea what a pivot is or how to go about pivoting in their business.

While books like The Innovator’s Solution, Running Lean, 4 Steps to Epiphany and many others have covered pivoting in some way, these are very technical books and focus on the tech startup community primarily.

That sucks because everyone should know how to pivot (in business and life).

So here’s my attempt at breaking down a pivot for the less tech savvy people of the world (me).

This is the framework and the mindset I use to approach everything (from the books I publish to the products I launch).

I’m no expert, but I hope my thoughts on the subject can at least get you started on the right path.

* * *

NOTE: this blog post assumes you’ve already built something and that it’s not working. However, it’s equally valuable for those about to build something because it probably won’t work (I’m not a pessimist, I’m just experienced in failure). So bookmark and take notes for later.

And if you like this blog post (and want more like it), shoot me a tweet to let me know!

[Click here to Tweet me to let me know you want more content like this!!]

* * *

Step 1: Lay the Foundation for Your Pivot (Figure Out What Worked and What Went Wrong)

In the Army, after every mission, training exercise, event (basically everything), they conduct what is known as an After Action Review (or AAR for short).

An AAR is a chance for key players (anyone involved in an operation or exercise) to identify:

  1. What was supposed to happen?
  2. What DID happen?
  3. Sustains – what did we do right and what should we do the same next time or in a similar (3 is usually the minimum)
  4. Improves – what did we do wrong and what should we do different the next time (3 again)

If you’ve read any of the business books I’ve listed above, you should see a thread that runs through the lean startup methodology

  • What was supposed to happen = Hypothesis
  • What did happen = Testing the hypothesis
  • Sustains / Improves = Measuring based on metrics you’ve established earlier so you can iterate (try again)

I conduct an AAR with myself or my team after every major shipped project.

For an AAR guide and pivot checklist and workbook, download The Essential Pivot Checklist and Workbook

AARs are valuable for things like:

  1. Writing. If I write for a major platform (like Fizzle.co or Problogger.net) then I want there to be some positive result (like X number of new email subscribers to my list, or Y number of comments, or…you get the idea). I need to sit down after something like this ships to see what the results actually were and if it’s worth doing again in the future (and how to improve the next time to get better results)
  2. Consulting. When I consult with someone, I want to make sure there’s a positive result for the person I’m helping. This is the only way to improve and continue getting clients.
  3. Projects. I launch a lot of projects. What were the results? What can we learn? How can we do better next time?

If you take away anything from this, know that pivoting begins with analyzing what was supposed to happen versus what did happen.

Without this basic knowledge, you can’t pivot (you’d just be shooting in the dark…which might work…if you’re lucky).

Step 2: Determine the Shift that Needs to Take Place for Your Pivot

Cool, so you know your first plan didn’t work…

Now what?

The AAR should give you insight into what to do next.

  • If your “sustains” included something that sorta worked, can you double down?
  • If your “improves” included something that completely missed the mark, can you scrap it altogether try a different approach?

More likely than not, some part of your original iteration worked.

If that’s the case, it may be useful to consider how you can maintain your original idea (mostly) while tweaking what worked to make it more effective (or reducing what didn’t work so it is less disruptive to your business model).

Conversely, if NOTHING hit the mark, it’s much more effective to change things dramatically.

Here’s Ash Maurya’s (author of Running Lean) take on it:

If the goal is to maximize learning, you have to pick bold outcomes versus chase incremental improvements. So rather than changing the color of your call to action button, change the unique value proposition. Rather than experimenting with different prices, experiment with different pricing models.

In other words: to know where to go, you need to know where you’re at.

That means determining if you’re FINDING the fit, or OPTIMIZING the fit.

Pivoting Before and After You Find Product / Market Fit

When I launched The Creative Entrepreneur (now Bootstrapped), I was shooting in the dark a bit.

Iteration 1: finding product market fit…

I knew I wanted to create some sort of annual publication with reoccurring revenue and I knew I wanted to focus on business.

The first thing I did was pitch the idea to potential contributors (the people who would produce the content for the publication.

This is how I received my first form of validation (I’ve written more about that here).

In a nutshell: I figured if people would write for the publication, then people would pay for the publication.

This is an assumption, of course, and needed its own round of testing (preorder sales).

I don’t want to go in depth here about validating an idea as that’s a topic that deserves its own analysis (read this article for more information on validation), but the point is: I was trying to find product/market fit.

With the preorders I received, I found it (at least in a small way).

Iteration 2: optimizing product market fit…better, no?

The next step for issue 2 was optimizing the product/market fit.

This required pivoting again by asking questions like:

  • How can I scale this?
  • How can I grow this?
  • How do we get more users, subscribers, etc.?

For us, that meant branding redesign, re-evaluating the content strategy, adding new sales channels, etc.

Have we optimized product/market fit?

We can’t be sure just yet.

Yes we’re getting subscribers and yes the reaction is overwhelmingly positive, but some of these tests take weeks or more to confirm for sure (especially big changes like a rebranding).

What’s the “Right” Pivot?

To be entirely honest, the answers to these questions are elusive at best.

Just like if you’re trying to pivot a new business (or an old one), you won’t know what the right answers are for sure. The point isn’t to know the answers at the outset.

The point is to have an idea and be willing and able to test until you find something that works.*

**just to emphasize again: what “works” for optimizing product/market fit is different than what works for finding product/market fit**

Step 3: Test and Measure Your Pivot

Testing and measuring your pivot is the simplest step.

Step 3 is all about taking meaningful action.

What did you decide to pivot?

  • Did you decide to change the pricing model?
  • Did you decide to add or remove features?
  • Did you decide to change mediums?

Whatever the choice, make sure you can measure it.

For example:

  • Changing a pricing model is easy: did you get more or less sales?  How does that affect revenue and profit overall? What’s the reception from your target market.
  • Adding or removing features? Again, how many more people opted in? Did you get more paid subscribers, more signups, more…?

You get the idea.

A pivot is only as useful as what you’re able to measure.

The Hardest Part of Pivoting

Testing and measuring your pivot is also the hardest part.

Not because it’s technical – it usually isn’t - but because it’s hard to pick ourselves up and test something that didn’t work out the first time.

It hurts to get rejected.

It hurts when we miss the mark again – sometimes more than the first time.

Here’s the deal:

There’s nothing to be ashamed of by retesting an idea in a new way.

If someone said no to your idea, it’s not grovelling to go back with a new pitch and ask again. In fact, the person you approach again should be happy that you adjusted course. After all, if this person is in your target market, they want what you’re trying to create.

So don’t worry about the rejection or failure (it’s all part of the process).

Instead, perceive and approach your pivot as an experiment and a game.

This works because…well, it is

So don’t stress – just test.

A Free Guide to Help You Pivot

Okay, so this blog post taught you a little about pivoting , but what’s next?

I always find it helpful to have some sort of guide or worksheet to help me follow through on material, so I took it upon myself to create a sweet downloadable (and FREE!) product for those of you looking to pivot in your business.

In the workbook you’ll get:

  1. A 2 page After Action Review workbook (including a breakdown of what an AAR is and how to use it)
  2. The 3 Step Pivot Evaluation Method (this will help you focus on what to target and whether you should focus on finding product/market fit or optimizing product/market fit)
  3. 10 “Target-Pivots” that Eric Ries of The Lean Startup uses when pivoting a business (this stuff is gold)
  4. The 5 Step Pivot Execution Framework (to help you put it all together!)

[Get your free copy here]

do it

* * *

I hope this blog and the accompanying checklist and workbook help you on your way to product/market fit and a successful business.

If you enjoyed this blog post, let me know.

Click to tweet me and let me know!

* * *

Started in Napa, California (just before meeting up with The Resistance, San Rafael Branch). Finished and Shipped in San Fransico, California.

Writing time: 9:14 (ouch…true story)




Rebuilding America with Chad Grills

Chad Grills is a veteran, entrepreneur and the author of the currently-being-crowdfunded-book: Veterans: Don’t Reintegrate, Rebuild America.

Chad and I happen to have a very similar background, and like myself, he is currently occupying his time with a cornucopia of projects.

(bonus points for using the word cornucopia in a sentence)

In today’s broadcast, we touch on some seemingly random topics (but I promise – they make sense in context), including:

Chad’s military background, his new book, Antifragility, Post Traumatic Growth, and how to hit the ground running as a military veteran transitioning into the civilian world.

By the way, Chad has less than two days left to fund his new book.

I already have my copy preordered.

You can support Chad and get your copy here.

What Chad Grills and I Talk About:

  • Chad’s transition out of the military and into the civilian world
  • Antifragility and how it applies to creating a better life
  • All about the Regret Minimization Framework
  • Post Traumatic Growth, or: how to turn trauma into momentum, regardless of where it comes from
  • How to transform fear into prudence, pain into information, mistakes into initiation and desire into undertaking
  • How to beat entrenched businesses as a bootstrapping underdog
  • Why it’s important to constantly run small experiments for personal and entrepreneurial growth

Wise Words from Chad Grills on Rebuilding America:

As Entrepreneurs, we need to give ourselves as much exposure to the upside while limiting the downside.

Where You Can Find Chad Grills Online:


Additional Resources:

Antifragile by Nassim Taleb


http://highspeedelite.com (exclusive veterans mastermind and network)

* * *

If you enjoyed today’s podcast, please leave a review on iTunes here. Thanks so much in advance for your support.