Category: Commentary

Lessons from Building Praxis – Part 5

“Do not neglect to show hospitality to strangers, for by this some have entertained angels without knowing it.” — Hebrews 13:2

I had a lot to do, much of it outside my ability, much of it costly, and I had a few grand I could put on my personal credit card and that was it. The idea for Praxis wasn’t fundable yet, and I didn’t even know what the letters “VC” meant anyway, let alone how to go raise.

But I didn’t need any of that, because I had something far more valuable.  I had dozens of accounts with positive balances of social capital, and it was time to cash them in.

Social is the most valuable kind of capital

The first decade of my “professional” life was full of meaningful connections.  I went out of my way to meet people, follow up with people, respond same-day to every email, look for excuses to write thank you notes (physical ones!), generously offer help without asking anything in return, and connect people to each other whenever possible.

Part of this is my personality.  I’m a connector and a people person.  But part of it was a choice and it took a lot of practice.  I am not sentimental, I move on to the next thing quickly, and I’m forgetful.  That made the practice of writing thank you notes the furthest thing from natural.  A leader I respected wrote me a thank you note for something small.  I asked him why, and he passed on advice someone had given to him, “Look for excuses to write thank you notes.”  It stuck with me.  I bought a stack and carried them with me everywhere, stamps and envelopes too.  I used them generously.

It’s not so much about thank you notes specifically, but the mindset necessary to write lots of them.  It requires/develops an abundance mindset.  You begin to see win-wins everywhere.  You become more grateful and happy.  You begin to see subtle ways people just doing their job is helpful to you.  This in turn makes you more able and willing to help more people out.

Instead of a social spender, you become an investor in your network.  When you meet new people, instead of handing them a business card and asking them to help you, you default to genuine interest in them, a real connection, and seeking any way in which their interests could be served by something or someone you know.  Every person you meet has an invisible account with your name on it.  Every interaction is a deposit or a withdrawal.

I made deposits.  Tons of them.  For years and years with no clear payoff at the end.  I enjoyed it and it seemed like a good idea.  I didn’t have a clear and compelling reason to spend any social capital, so why not keep investing and saving unless and until I did?

When I went all-in on Praxis, I knew this was the time to empty my accounts and even go into social capital debt.

I turned to friends, colleagues, acquaintances, and acquaintances of acquaintances.  I cashed in every ounce of social capital I had and got some lines of credit.  I asked for introductions, advice, lists of leads, design help, tech help, legal help, strategic help, research help, product development help, and most of all help spreading the word.  I traded some phantom stock and paid some cash, but I mostly traded on goodwill and positive social capital I’d built from helping lots of people, being kind and open appreciative, and having a reputation as a guy who helps lots of people.

Had I seen my professional life as a zero-sum game, where I must exploit and best every threat and carve the biggest slice of a fixed pie, Praxis never would have left the launchpad.  The fact that I chose to see it as a positive-sum game, where helping as many people win as possible would grow the size of the pie, meant that I had access to a lot more of it when the time came.

The social capital I cashed in to get started was priceless.  I’m not being cute.  There is no amount of money I could have raised that could have accomplished what a deep, wide, and rich social network did.

I’m so glad I had the patience and self-control to not get spendy early in my career and trade tiny bits of social capital for tiny promotions, pay raises, or prestige.  I needed a huge balance to build a company, and my long-cultivated habit of generously depositing social capital everywhere possible was the only way.

Lessons from Building Praxis – Part 4

“The most powerful force in the universe is compound interest” — Albert Einstein (unverified)

Ever heard that riddle about whether you should take a million dollars or a penny, doubled each day for a month?  Take the penny.  You’ll end up with $1.3M if it’s a 28-day month, and as much as $10.7M if it’s a 31-day month.

Doubling is extreme, but even growth of a fraction of a percent compounded every single day can achieve mind-boggling results.  When you’re trying to go from idea to inception, progress each day is crucial.  You can’t get stuck waiting for one big leap.  You need to take at least one step every single day.

Do one thing every day to make your company more valuable

I was in way over my head when I decided to make the idea for Praxis a reality.  How to file for incorporation?  Do I need to do that before I build a website?  How to build a website?  Do I need money?  Where to get it?  Do I get businesses lined up first, or start selling customers first?  What price-point makes the most sense?  How to describe the company?  Do I need brochures?  Do I need a formal business plan?  Do I need to build the curriculum first, or get some market interest first?  Do I need to setup a business bank account?  Who could help me navigate all this?

My brother, a seasoned entrepreneur already, told me to chill out.  He said none of that matters right now.  “Just do one thing to take the idea closer to reality.  Just one thing.  Then after that do one more thing.  If you run out of things and hit a wall that requires some kind of outside assistance, get it.  Until then, don’t worry about it.”

I was mentally trying to solve problems from the future.  I had a list of hurdles I imagined stopping me tomorrow, and it was crippling my today.

His advice was freeing.  I was still working full-time and wasn’t able to devote all my time to Praxis anyway, so I made a commitment.  I would do at least one thing every single day to make the company more valuable.  That’s it.  Just one thing.  No other deadlines or goals of having this or that done by this or that date.  Just every day, I had to answer ‘yes’ to the question, “Is Praxis more valuable now than it was yesterday?”

Some days I couldn’t do anything but search the web for ten minutes looking for similar programs in the market, or buying a domain.  Not massively valuable, but one thing done.

Other days I spent hours on end feverishly writing marketing copy, contacting business owners, talking with college students about whether they’d consider alternatives, building spreadsheets to play with the business model, talking with web designers, outlining the curriculum content, and more.

I did as much as I could whenever possible, but what really mattered was hitting my minimum of one thing done.  What really mattered was not letting a single day go by where this thing didn’t make progress.  Time is the enemy with a startup.  A day without action means you’re going backwards, losing value.

This approach worked wonders.  The idea never lost momentum.  There wasn’t enough time to talk myself out of it.  Some days I was on fire with enthusiasm and faith in the idea, other days I did my one thing with little excitement and lots of doubt.  But I committed to doing one thing every day, so I had to act regardless of inspiration.  It moved me from the vulnerable sand of emotion to the unsexy concrete of action.

And it did compound.  I made it so much farther than I ever imagined before I even needed to think about things like raising money or addressing big huge hurdles I imagined.

Lessons from Building Praxis – Part 3

“I would go 0 for 30 before I would go 0 for 9.” — Kobe Bryant

Launching a startup takes some big, scary leaps.  You can’t leap tentatively.  You can’t go in with an escape plan.  You need to burn the ships behind you when you reach the shore in order to have the tenacity necessary for the attack.

Go all the way or don’t even try

When I knew I wanted nothing more than to get Praxis off the ground, there was one more hurdle before I got started.  My most important partner in every endeavor needed to be on board.  My wife.

I’m pretty persuasive and she’s pretty trusting of me, so many times in our marriage I talk her into something.  She’s not an easy sell, but if I persist enough, I can usually get at least a tepid ‘OK’.  The problem with anything less than full-hearted agreement is that if things go south I’ve got to pay later for pushing her further than she really wanted to go.

Even if unspoken, the feeling that I dragged her into something that turned out badly is awful, and a wedge in the family.  It puts me in a defensive position, irrationally trying to justify the decision while she goes on the offense and uses her original hesitancy as leverage against me.

I knew that a startup was unlikely to succeed under these conditions, and my family certainly wouldn’t.  That wasn’t an option.  I needed her in on this 100% if I was going to be able to go in 100%.

So I made a pitch.  It might have been the weakest pitch I’ve ever made to her.

I said, “I believe in this idea.  I love it.  It feels different than other ideas.  I am willing to commit to launching this thing whatever it takes, win or lose.  But I’m only willing to do that if you are in too.  I don’t want you to go along with it just to make me happy and then later regret it.  I don’t want you to use it against me later if doing this means we have to suffer.  I can’t promise you anything.  We might end up living in my mom’s basement.  I might be working all night.  I might be emotionally drained all the time.  We might get clobbered in the market.  We might have haters.  We might succeed and get rich and have a lot of friends and family resent us for it.  I have no idea.  All I know is that I’m willing to go for it and live with the consequences, but only if you are too.  Take all the time you need to decide if you’re all in.  I won’t mention it again.  Think really realistically about what it might mean, and whether you will be bitter down the road if it’s tough.  If you say no, I will not pursue it.”  And I meant it.

She said nothing but, “OK, I’ll think about it.”

I was chomping at the bit.  I could not wait to get started, but I also prepared myself for the possible pain of her saying no.  There’s only one thing in the world that could keep me from launching this thing, and that was my family.  That’s the one thing I couldn’t force and cajole.  It had to be real, genuine agreement.

I waited.

I waited some more.

OK, now it’s just getting ridiculous.  Did she forget?  Is she trying to torture me?  Is she waiting for me to sweeten the deal somehow?  Maybe I should remind her?  No.  I told her to take as long as she needed and I told her I’d say nothing more.

So I waited.

We usually make decisions very fast.  A few minutes is normal.  A few hours an exception.  Days?  Never.

Two weeks.  The longest two weeks of my life.

After two weeks of silence, one day as I was grabbing a snack and she was standing in the kitchen she looked up and said, “OK.  Let’s do this.  I’m ready.”

That was one of the best moments of our marriage.  Probably because it’s one of the few times where I didn’t do any talking.  I knew she meant it.  I knew it was her saying yes to Praxis, not her saying yes to me.  That meant everything.  I needed her on my side to go full throttle.  She gave me a blank check to pursue this thing come what may.  That was by far the most valuable investment in the company.  She was the first investor.  The first person to believe in the idea so strongly they were willing to put tremendous personal resources at risk to make it a reality.

We’ve had hellish moments.  Many.  She’s never once held it against me or asked me to stop or complained that Praxis takes a toll.  She gave me the go-ahead to keep shooting the ball, even if I went 0-30.

If I had partially pursued it while hoping to win her over just enough to let me pursue it a little more I would have gotten crushed by the first big setback.  I could always use the excuse, “Well, I guess I have to stop for my wife’s sake.”  Destroying any excuse to retreat or any way to pin it on someone else put me in a position of win or die.  Best thing I could have done.

Lessons from Building Praxis – Part 2

Are you willing to fail in order find the answer to your question?

Everyone is too scared of failure.  But also everyone glorifies failure too much.  ‘Failure porn’ is a real genre of Medium articles and trendy startup swag.  It’s pretty stupid.

Failure sucks.  It’s awful.  It should be avoided.  You shouldn’t feel weird for not liking failure.  You should want to win.

But some things are worth failing for.  When you find one, you need to act and fast.

The willing to fail test

I had a lot of business ideas prior to Praxis.  All of them shared a common trait.  They all required several things I didn’t have if I were to pursue them.

“If I knew for sure about X, I could try this.”

“If I had X amount of money, I’d try this.”

“If I could find person X, I’d try this.”

I liked the ideas, but I needed less risk in order to take a step.  In other words, I was willing to launch any number of them, but only if I knew there was very little chance of failure.

That’s a sign that I’m not the right person to launch that company.  If you’re in it because you think it’s a sure thing, you will quit when it gets really, really hard.  And it will.

Praxis, on the other hand, was so all-consuming and captivating that none of those objections mattered.  I didn’t have money and I didn’t know how to get it.  I didn’t have the team, expertise, market knowledge, or any assurance demand was real.  I didn’t care though.

I was so obsessed with the question, “Is my theory about a better way to build a career correct?” that I needed and answer more than I needed the answer to be ‘yes’.

This was the first business idea I was willing to fail for.  When I thought about trying Praxis and failing, it felt ten times better than the thought of not trying it at all.  That was the test.  That was how I knew this was the one.

That’s when I cashed in all my chips.  I don’t want to fail, but I want my answer more than I want to not fail.

Lessons from Building Praxis – Part 1

“Can’t change the world unless we change ourselves” – Notorious B.I.G. (probably not)

My colleague TK Coleman and I like to joke about this quote from the trailer of what looks like a badly made movie about one of the greatest rappers of all time.  It doesn’t seem like Biggy would’ve uttered such an empty cliche, so we use it in situations that get too close to cheesy inspiration as a way to playfully mock self-seriousness and pretension.  Never fails.

But like all fluffy cliches, it’s true.  That’s the first lesson for getting a company from idea to reality.

You can’t build a company unless you build yourself

TK was busy building a career in Hollywood, hustling to act, produce, write, and launch a entertainment tech startup.  He decided to do something that had nothing to do with his career goals and was not required for any job.  He started blogging every single day.

TK prioritizes personal growth over everything.  He’s a voracious reader, and he decided he needed to push himself to do more than consume ideas.  He needed to create, and ship them out to the world.  I watched him transform from an irresponsibly curious guy to a disciplined, creative machine.  Then he turned it on me.

He challenged me to blog every day for 6 months.  I committed, and that was the first step in the launch of Praxis.

The blogging had nothing to do with startups or Praxis.  It had to do with pushing myself to become a better version every day, even if I didn’t have to.  I had a great job and daily blogging added nothing to it.  But it worked wonders for my personal growth.  I became a creative machine.

More ideas came, more energy, more confidence, and more clarity.  Finally, an idea a decade in the making came into focus.  An alternative to college.  It seemed so simple, and I’d been sniffing around the edges of something like it since my own underwhelming university experience.  Praxis was born because TK continued to build himself when he didn’t have to, and pushed me to do the same.

We built the company around this culture.  Every member of the team is inspiring.  They are each committed to relentless personal growth.  That’s why it works.  A person who knows how to grow themselves and add value to their own life can grow an idea and add value to a company.

I had a lot of entrepreneurial ideas prior to Praxis.  Most were pretty weak, some were good.  But it didn’t matter.  I didn’t have what it takes to execute on any of them until I pushed myself much, much harder on personal growth.  Monthly challenges, daily blogging, and a commitment to doing one thing each day to add value to myself were prerequisites to launching a company.

The idea matters.  But ideas come and go and are unpredictable.  You can’t wait around for a great idea.  Get busy building yourself so that if and when a great idea comes, you’ll be ready and able to act.

Get Your Ass Out There

You can’t sit behind a walled garden becoming an expert before you reveal your stuff to the world.

No one hides for a decade, refining and refining, then releases a completed magnum opus to the world.  It will suck.

Give, give, give, ship, ship, ship, create, create, create, work, work, work, repeat, repeat, repeat.  Get your stuff out there.  Do your work loud.  Be in the world.  Be findable.  Get feedback from the market.

Get off your ass and out of your head.

One Way to Tick People Off…

Achieve quickly what they labored long and hard for.

This is guaranteed to enrage some set of people.  Even if your success is not overnight, if it appears you achieved it quickly, or with fewer hoops than most in your field, they will not like it.

You see this play out all the time.

Someone without credentials makes a claim that gets a lot of attention.  Angry responses from experts are mostly, “You’re not a real X”, “You need to engage the literature”, and, “You don’t know what you’re talking about.”  Not arguments in response to the claims themselves, just anger at the one making them and the route they took.

Someone writes a best-selling book on a topic where others labor in obscurity.  How dare they appeal to the crass common man instead of publishing through the guild!?

If people accuse you of doing something you have no business doing, they are probably threatened by you.  Not so much what you’re doing, but the fact that you did it without their permission.

What’s Your Dominant Trait?  Ideas, Angles, and Hustle


Ideas people are motivated first by ideas.  Their love of ideas is what leads them to action, and all their actions are rooted in some philosophical pursuit.  They can get obsessed with an idea, lost in it, forgoing all else.  They are often intellectuals, artists, or entrepreneurs.  They tend to gravitate toward areas where they needn’t subvert their ideas to a grander scheme, or get on board with someone else’s.  They need space to think and pursue ideas.  They like to look beyond the dominant games and imagine new games.  They have huge upside when ideas are translated into action.  The risk is getting so lost in an ever-shifting amorphous cloud of intellectual exploration that it’s never applied to the real world and nothing gets done.

Angles people are motivated by finding the angle.  Masters of exploiting the moment and expediency, they have a nose for power and a knack for finding those who have it and aligning with them.  Anglers are in the right place at the right time.  They identify and single-mindedly pursue an advantageous orientation around the next big thing.  They are great at spotting a trend (not starting one), making a deal, and adapting to volatile environments.  They thrive in large corporate, financial, legal, and political environments with lots of written and unwritten rules.  They like to figure out the rules of the game and win within them.  They downside is that they aren’t entirely trustworthy.  Without a clear motivating philosophy, angles people are valuable but usually kept at arms length from real power.  They are ready to be the right-hand to the new king at any time.

Hustle people are motivated by the thrill of the pursuit and come alive in the heart of the grind.  They find ideas interesting, and pick them up and set them down easily, using bits and pieces that help them hustle harder.  They are radically practical, philosophically open but minimalist.  They want to build, and wherever they are, they’ll start building.  They will play games or not play them with equal indifference while they focus on building new games, not for the ideas behind them as much as the challenge of building.  They make great small business owners, salespeople, manual laborers, athletes, and bootstrap entrepreneurs.  They are by far the most productive people and you want them on any major undertaking to drive the execution.  The downside is their focus on action at the expense of philosophical foundation or can lead to contradictions, or have them inefficiently violating the 80/20 rule.

I think everyone has some of each trait, but one is dominant.  If you can identify your dominant, secondary, and tertiary traits, it will help you double down on strengths and structure your life to guard against weaknesses.

I’m an ideas>hustle>angles person.  My brother is a hustle>ideas>angles person.  I know good, successful, powerful people with all kinds of combinations, with one exception: I’ve never met someone dominated by angles who is really top-notch ascendant.  They can be worth working with or around, and can get a lot done.  But they’re not long-term partners or deep friends.  You have to sleep with one eye open around them, which gets exhausting.  Angles are incredibly important to understand, and the insight into power-relations and trend-spotting are invaluable.  But if that’s your primary motivation, I worry.

I think you can alter your dominant orientation.  If you do some exploration and figure out why you’re motivated as you are, you can find other ways to get it than through ideas, angles, or hustle.  Do you hustle all the time out of guilt?  You can deal with it in other ways.  Do you exploit angles out of fear of being powerless?  Other ways to gain personal power too.  Are you lost in ideas out of anger towards falsehood, or fear of engaging the material world?  Ways to address that too.

This trichotomy is useful for me in identifying people I want to work with and roles for which they’d excel.  Early on with Praxis, we needed mostly ideas.  Then more hustle.  Now we need a solid mix of ideas and hustle, and we definitely need people with skill at seeing and exploiting angles too, as relationships increase in number and complexity.

How Do I Get More Music in My Life?

I used to sit in my room for hours listening to music.

Nothing else, just listening.

It was a kind of therapy, philosophy, and creativity all in one.  It helped me know myself better, think lyrically and eventually begin writing, and ascend above any situation.

I rarely do this anymore.  I’ve got a noisy house full of kids and a day full of awesome work to do.  I listen to music while working as background.  When I take a walk I usually do podcasts or audiobooks, as reading is tough to fit in at home.  When driving, the car has too many kids to really lose myself in music seriously (doesn’t prevent me belting out diva tunes to annoy my kids and amuse myself).

Every time I do get lost in music, while doing the dishes or driving alone, it soothes my soul and inspires me in a way nothing else can.  I get lost imagining myself on stage, or fighting in some epic battle, or a blur of abstract images.  I get chills marveling at the notes hit, or harmonies woven.  I tell myself, “I need more of this.”

Still, it’s a costly indulgence.  Carving out time to do nothing but listen to music is as tough as hobbies like golfing, skiing, or surfing for a dad and entrepreneur.  It can be done, but it’s almost never worth the trade-offs.

Maybe I’ll join a band again in 15 years when my kids are mostly out of the house.

Don’t be Afraid to Be Interesting

Nearly every significant business connection I’ve made has been because of my deep love of ideas.

The value of my radical, ideas-based network dwarfs that of my pure business/practical connections.

I spent most of the first ten years of my “professional” life getting lost in ideas. When I began fundraising, and then started Praxis, it was my deep love and knowledge of ideas and obscure thinkers thought brought the greatest returns – including both rounds of angel investment, pretty much all Praxis team members, nearly all my speaking gigs, and all of our best business partners.

It’s not that hard to find business-savvy networkers, so those who try to access high-value people using that alone face steep competition. People who are both building things AND deeply philosophical have a huge advantage, because many high-value people are also deeply philosophical, and they love to talk ideas.

Don’t underestimate the profound practical value of chasing ideas with abandon. Not name-dropping, angling type of idea-chasing. That is repugnant and can be smelled from a mile away. Genuine seeking.

Don’t be afraid to be radical either. Stuff I’ve openly written and spoken about unschooling or anarchy have brought more high-value connections to me than the safer stuff, and though they doubtless ward some people off, the ones they attract tend to be better connections anyway.

My take-away?  Don’t be afraid to be interesting.  Don’t hedge in pursuit of truth.

Edit: Per my colleague Cameron Sorsby, worth noting that a bumper sticker is not a philosophy. When people dig deep, if they find deep engagement with ideas, that’s an asset. When people take a glance, if they’re blinded by wild shouting and signalling about ideas, that’s a liability.