Entrepreneurship is Mostly About Self-Knowledge

The hardest part about being an entrepreneur is that you’re constantly forced to tease out of yourself stuff you know that you don’t know you know and don’t know why.

You have to make decisions. Many of them have pretty big stakes. Big changes to upside and downside probabilities. You can think through and analyze them easy enough. But that’s not enough.

Some things just feel right. Some things just don’t sit right. Some things are stuck in flux between the two.

Your job is to decide. But to do that well, you’ve first got to figure out what the hell you know and feel about the decision and why.

Plumbing the depths of your own gut, or subconscious, or spirit, or whatever you want to call it is no easy task. It’s hard to get down there and access the source of your inclinations. And you never know what you’ll find. You may not like it. You may try to pretend it’s not true, because your head tells you you’d have to be an idiot to feel that way about that decision.

So you have to develop rigorous self-knowledge (hard), then rigorous self-honesty about what you find (harder).

Once you go through the brutal process of figuring out what you actually want and accepting it, the decision part gets easy and fun.

But if you avoid the interior exploration and confirmation, the deciding part is torturous and only gets worse over time. Second guessing and sleeplessness are signs you haven’t yet figured out what you really want or accepted it.

This is true in all parts of life, but business forces you to confront it more quickly and frequently than most areas.

Categorized as Commentary

How to be Content with the Present by Living in the Future

Someday, you will look back fondly on these days.

That thought just hit me this morning.

I was going through my mental rolodex of all the things I have to do, deadlines, pressures, unsolved problems, and promises. I was annoyed at the weather, annoyed at things around my house and property I have to repair, annoyed at a lot of the inescapable elements of this phase of life.

Staring out the window processing my tasks for the day I fixated on a small tree whose branches changed to stunning red in the last week or so. It was beautiful. I heard my kids through the door bickering and chattering.

Then the thought hit me out of nowhere.

Someday, you will look back fondly on these days.

And it’s true. I know it’s true because I look back fondly on the other phases in life I’ve completed, even though in the midst I was usually focused only on what needed doing and improving.

I don’t think it’s a bad pattern. Discontentment and a drive to do and accomplish is inherent in humans. As long as it’s paired with optimism, it can be good.

But taking a minute to recognize that I will likely look back fondly someday on this phase – the ages of my kids, the place I live and work, the early chaotic stage of the company – suddenly made me feel a lot happier and more relaxed.

Categorized as Commentary

Live-In-Market > Go-To-Market

All the typical growth strategies for startups are still useful. But not as stand-alone activities.

For maximum effectiveness, they are nested activities.

First, they are nested within a cluster of partners. Each strategy gains leverage when done together with partner companies – complimentary tech, service agencies, affiliates, and alliances.

Next, they are nested within a community or ecosystem. This is where customers, partners, and individuals trusted by both live and interact.

While recording the next PartnerUp Podcast episode yesterday, Airmeet CMO Mark Kilens laid out the six basic growth approaches:

  1. Sales led/outbound
  2. Content led/inbound
  3. Events led
  4. Product led
  5. Partner led
  6. Community led

These are all valid, but listing them on the same level felt off. As we talked, I sketched out on MS Paint (my favorite design program) the way I think these are layered for maximum effectiveness.

You could swap “ecosystem” for “community”

To win big, you need several things.

  • Live in the community/ecosystem where your customers, partners, and those they trust live
  • Create and maintain partnerships with the complimentary companies in that ecosystem
  • Build a sales process that co-sells with partners in that ecosystem
  • Build content with your partners (Mark’s rule: “60% of our content should be created by someone other than us”)
  • Host events with your partners (Tyler Calder, CMO of PartnerStack: “We’ll never do another event alone”)
  • Co-innovate with partners on your product – involve them in the process, make integrations core to the roadmap

Of course to really get the flywheel going, you’ve got to think about how your customer success strategy is nested in partner relationships which are themselves nested in an ecosystem.

Turn those customer service requests into referrals for service partners. Turn help documentation into partner education content.

The efficiency and effectiveness gained by living in market and partnering on every action, vs going to market with siloed strategies is immense.

PS – a 5-day deep dive into what this approach really looks like for each department is happening November 7-11. Join us at the PL[X] Summit!

Categorized as Commentary

The Fake Book

When I was a kid at the music store my mom asked an employee the best way for a novice to learn to play a song from the radio.

She made us take piano lessons and we didn’t like it. We said we’d like it more if we got to play popular music instead of classical stuff. She called our bluff.

The guy said, “Well you could get the actual sheet music, but that’s gonna be pretty hard to play. Their are simplified versions too, but honestly, I’d just get The Fake Book.

My ears perked up.

The Fake Book was a cheat code. It showed the basic chord progressions of songs, rather than typical sheet music which showed the exact notation. The Fake Book gave you the building blocks and let you improvise with your ear on the rest.

I don’t think we ended up getting The Fake Book. Or if we did, I didn’t end up using it. But the concept was a game changer.

When the the guy at the music store nonchalantly suggested it, it opened up a world of possibilities. It was like someone telling me that all the instincts and habits I’d thought were bad were actually okay. He was telling me I was right, and I should keep following my instincts instead of fighting them.

I didn’t know at the time, but I’ve always been an 80/20 guy. I want the quickest route to the closest version of the answer.

This musical cheat code – learning the chords and playing the rest by ear – got me through years of lessons.

I never learned to read sheet music, but my teachers either never figured this out or just wanted to get me through the 30 minutes a week my mom was paying them for and let it slide. My eyes wanted to be glued to my hands, but I had to pretend to be looking at the music at least every once in a while.

I realized I was pretty good at memorizing tunes, so I’d ask the teacher to play a new song several times for me first. Then I’d struggle through a few times. Then I’d go home and memorize it so that next week, they’d think I was actually reading the music.

When my mom let me quit piano lessons, I picked up guitar. All my buddies were learning too, and we all faked it together. We’d play what sounded like songs we heard on the radio, never trying to figure out the exact fingering.

After playing guitar for a while, I realized that I actually loved piano, despite hating lessons. I still used the piano keys as a visual reference in my head when playing guitar. So I started playing again.

It wasn’t until I played with some worship teams at church that I realized they all used The Fake Book approach. Every week, members of the band got a sheet with the lyrics and nothing but the chords. No notes. They did the rest by ear and improvisation.

I was in love.

The Fake Book has been my approach to pretty much everything since.

When I encounter something new, I do two things: Listen or watch people do it, and try to figure out the basic chords. I ignore the detailed notes, tabulation, and debates over time signature.

Then I try to do it myself as soon as possible. Not worrying about anything but producing a reasonable facsimile to the basic melody.

What’s crazy is in every field, you imagine the best are insanely trained classical practitioners with perfect form and the ability to read complex sheet music. Most of them are more like the worship team. They’re using The Fake Book method too.

I’m not denigrating classical training. Those people are wizards. There are things they can do I can’t even dream of. Either because I lack the talent, or I’m too lazy, or both. What they do is awesome, I respect it, and I’m glad it exists in this world.

I’m also glad it’s not the only way, like I thought before I heard about The Fake Book.

You’ve got to know what works best for you. Once you do, work with it, instead of against it.

Categorized as Commentary


I have a theory on when to work through anger and when to channel it.

When you’re not sure of the source of the anger, it requires working out. Without clarity, it will compound and damage things around you. A tangled call of causes will accrete complexity unless you stop and start to unwind it.

When you know exactly what you’re angry about and you can isolate your focus to it without dragging in anything else, it’s probably a good time to channel that into some kind of productive activity.

First, understand it. It often dissipates from this alone, or drives you to conversations or actions that do. If it doesn’t, channel it.

Categorized as Commentary

Learning and Becoming

You can’t learn from every experience.

The most important experiences don’t translate into ideas and postulates and theories and frameworks you can codify, teach, systematize, or apply elsewhere.

The most important experiences change who you are, not what you know.

The greatest challenges, if handled with integrity, transform you into a superior version of yourself.

Sometimes lessons are drawn along the way. But when you have a genuine peak or valley, the value is not in what you gain, but who comes out the other side.

The next step of the journey requires more than different ideas. It requires a different person.

The point of learning is to use the knowledge to achieve greater ends. Achieving greater ends requires not just knowledge, but a greater version of you.

If you can’t explain what you learned from an experience, don’t sweat it. Let it work in you.

Categorized as Commentary

The Humility of Parenthood

There is no escaping humiliation as a parent.

Even if you think you’ve done everything right, your kids will reveal to you ways in which you didn’t even know it was possible to fail. You cannot stand blameless before the world and say, “I made no mistakes as a parent”. It’s not possible.

The mistakes that are easy to identify aren’t the most humiliating. Saying, “I didn’t know what I was doing here, and I would do it this way now” is hard, but not that hard.

What’s really hard are the times when you know you haven’t done things well, but you don’t quite know why or what you would’ve done differently. The known unknowns of parenting.

The grace in all of this is that this kind of humility is good for a person. There aren’t many other ways to get it, and none quite as powerful.

Being backed into a corner, forced without escape to see in yourself shortcomings, errors, and screwups you can’t even pinpoint removes the feeling of smug superiority from the field of options. You know too much about what your kids reveal in you to maintain it.

Being stripped of that sort of pride and learning to be ok with the inability to defend yourself at every turn is a kind of freedom that only comes with pain. But it’s good.

Categorized as Commentary

Two Kinds of Business

You can get away with mistakes and missteps in business if you don’t make big promises.

A more laid back, low expectation business has wiggle room for screw-ups but limited ability to grow fast.

You can get away with huge, even unrealistic promises if you never drop the ball on things.

A more ambitious, high-risk business can grow fast but has almost no wiggle room for screw-ups.

You can’t have both at once. You’ve got to choose. Would you rather be able to drop the ball from time to time and have everything be ok, or would you rather go big?

Neither is right or wrong. It depends on your preferences and priorities.

Categorized as Commentary

You Don’t Have to Make Up a Story Because it’s Already There

There’s a story behind everything. Finding it can be a trick.

Pick up a loaf of bread, a stick, or a T-shirt. They aren’t just objects. They are part of a narrative.

They have an origin, a destination, and something in the middle. There’s a ‘why’ to them.

Your life, also being a narrative, is a complex web intertwined with the narrative of everything you encounter. But teasing it out, making it explicit, and putting words around it can be tough.

Once you learn to do it, you can’t undo it. You see narrative the way Neo saw the virtual reality in the lines of code.

That’s when the real fun begins. Every person, every company, every event, every action, every product has a narrative and is part of other narratives.

Those who can see and surface these narratives influence where the narratives go.

Categorized as Commentary


Many scientific theories are attempts to explain things we already know. Especially about human beings.

We know gut instinct is a real thing. We know butterflies and lack of appetite and a sinking feeling are serious signals to be heeded. We know when a decision is wrong even when we can’t craft arguments for why.

Our gut is smarter than our ability to understand how or why it works.

It’s there for a reason. It might be your greatest asset. It certainly is in times of trouble or high-stakes decision.

Listen to it. Don’t abandon it. Stick with it. Be true to it.

If you don’t, you become double-minded and perpetually plagued by self-doubt, regret, justification, and confusion.

The gut doesn’t come in to play often. But when it’s telling you ‘no’, listen.

Categorized as Commentary

Without Words

Some of the most important experiences need silence more than description.

This is something I’ve had to learn slowly. I’m an expressive, verbally processing person. I want to talk about everything.

This is beneficial most of the time. I’m good at teasing out of myself and others feelings, beliefs, and fears that need to be surfaced and dealt with.

But parts of reality are beyond words. The effort to verbalize them takes something away, prematurely stops processes at work.

A related phenomena: when I put down bullets or an outline for something I want to write, it decreases the odds I’ll actually write it. The act of jotting down the ideas is a release valve. It offloads the ideas and ends the beneficial discomfort they cause. It pins them to a future date, and present tension is released.

But the tension of the unexpressed is the very thing needed to complete the work!

Some moments and movements need silence.

I’m trying to learn and practice this.

Categorized as Commentary

Ellsworth Toohey

“A world of obedience of and unity. A world where the thought of each man will not be his own, but an attempt to guess the thought of the brain of his neighbor who’ll have no thought of his own.”

Toohey used to seem like a far-fetched villain. And maybe he is. Maybe all of those impulses and traits cannot exist in a single body to such a degree. But Toohey definitely exists, even if in aggregate, and has become one of the dominant forces at war in this world.

The total sublimation of self into an infinite regress of what each person imagines the next person wants sounded crazy too me until 2020.

The deliberate destruction of beauty and propagation of ugliness sounded too much until the bulk of critically acclaimed art and advertisement in the last half decade or so.

I don’t know if there are singular Tooheys behind these shifts, but the spirit of the character has definitely taken hold.

The only way to fight it is as Roark did. Not with Twitter call-outs and exposes. By ignoring it and building the beauty you want in the world.

Categorized as Commentary

What Happened to the Internet?

I guess I should’ve expected it.

I had a naïve assumption that the internet meant the release of information permanently. That everything – good, bad, true, false – would make its way online, and therefore be forever findable.

I never thought everything would be easy to find or equally treated (which would be a horrible experience), but assumed it would be there. I assumed controversial things would have findable info from all sides. I assumed things done or said wouldn’t disappear or become altered with no record of what they used to be.

Those assumptions were wrong.

It’s been shocking how quickly this seemed to happen, or at least how quickly I began to take notice.

Google searches are not good anymore. And they’re getting worse. Google’s goal of “a single result” is one of the worst ideas I can imagine. And they seem to be moving towards it with fewer and fewer meaty results, more flimflam, lots of sanitized “officially sanctioned” fluff, and a whole lot of weird bot created content in between.

Wikipedia was never perfect, but it seems worse than ever. But now, even the internet archival services are scrubbing things. History is literally being erased.

I don’t know if there’s any solution except to change our comfy assumptions about the availability of information. The internet seems to be creeping toward a much noisier version of Pravda. At least wholly owned state propaganda papers were known as such and discounted accordingly.

We’re caught off guard because The level of fakery and bullshit on the internet happened quickly, and the quantity of info out there can make you feel like everything’s represented. But scratch the surface and those assumptions fall apart.

New approaches, tools, and mindsets are needed to wade through the internet today. And new offline info sources are needed as well.

Categorized as Commentary
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