Category: Commentary

“Maybe I destroyed the game.  Or maybe you’re just making excuses.” — Michael Jordan

They can do it because they got funding.  You’re stuck because you need money to do all the big things necessary to grow your startup idea into a real company.  If only you had the advantages they do!  Of course they have traction, because some VC took a chance on them.  You can’t get customers without money!

Lies.

All lies.  I had to learn and relearn this.  I thought I needed money.  Nope, not yet.  Maybe now?  Nope.  Still more I can do.  Now?  Still no.

Don’t look for money until you’ve tapped out everything else

It takes a lot longer to exhaust all possible bootstrap growth activities than you think.  When money is not an option, you get way, way more creative.  Every time you think you’ve reach a true stopping point, where nothing more can be done without money, you discover a new batch of things you can do to move forward.

I’m not for or against raising money.  What I’m against is closing off your greatest asset – your work ethic and imagination – because you’ve bought the, “I can only do X with money” narrative.  I’m wary of this narrative because I had to fight it.  It’s a tough opponent.

My brother bootstrapped a company for seven years with no outside funding.  When he went to throw gas on an already growing fire, he was able to raise $10.2M in less than a year on great terms.  It was his sound advice that tied me to the mast to resist the Siren song of fast funding.

I’m good at selling a vision.  Raising money seemed an easier task than grinding out some traction.  I kept thinking I’d better go raise so I could build the product the way I really wanted to, market the way I really wanted to, etc.  My brother’s advice reeled me back in.

I’ll never forget it.  We were sitting in my 2002 Saturn in an Isle of Palms parking lot outside a hotel where he was spending the weekend while visiting us.  He said, “What are you stressed about?  You have an ideal situation.  You have a great job that allows you to build this thing on the side for the time being.  Just keep doing that.  Do every single thing you can before you even worry about the need to quit your job, raise money, etc.  Not only will everything you do now improve terms for any future funding, but if you had a million dollars right now, how would you use it?  You’d probably waste it.  You can try stuff cheap now, experiment at low risk, and figure out what efforts are worth more money.”

I knew he was right.  I didn’t want him to be right, because the, “Imagine all we could do with money” narrative is exciting and intoxicating.  But I knew I could do a lot more before I actually ran into walls that couldn’t be climbed without money.  I also knew he was right about wasting it.  If I had a million dollars to start Praxis, I shudder now to think of all the ways I would have misused it.  I needed small victories under my belt before I took any big swings.

Not only does bootstrapping as long as possible mean you get more creative, figure out what gets traction, and improve future terms, it also means you have more skin in the game.  This is an important incentive structure.  The more you are playing with your own resources, the sharper your decisions.  Milton Friedman famously described the four ways to spend money, and the level of care with which you’ll act in each case.  You’re the most prudential spending your own money on yourself, less spending your own money on someone else, less spending someone else’s money on yourself, and least of all spending someone else’s money on someone else.  The longer you can incentivize the wisest form of spending, the better.

Outside funding isn’t evil.  It’s wonderful and can be necessary.  I ended up raising an Angel investment just nine months after deciding to build the company.  Paradoxically, it was only after I firmly committed to build the company without funding that people began to take notice.  I didn’t seek the Angel investor, he sought me.  Why?  Because I had a bit of buzz and traction.  Buzz and traction I wouldn’t have if I’d spent those months chasing funding instead of trying to get my first customer.  I was building the company, with or without money, which made the prospect of investing attractive.  People want to invest in momentum, not just ideas.  I wasn’t bluffing.  Praxis was going to keep moving, money or not.  That commitment was necessary.

Every time I thought I was out of steps and needed money, I refused to let myself give in to the narrative that money was my only move.  I’d ask myself, “If money wasn’t an option and would never be an option, what would I do?”  There was always something.

Maybe well-funded startups destroyed the game.  Or maybe you’re just making excuses.

“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.

“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.

“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.

“”In some attempts, it is glorious even to fail.” – Longinus

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.

“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.