Finally Emerging From A Founder Depression

At times we can be our own worst enemy.  The challenge is to minimize those times.

We often hear choosing to become an entrepreneur – and the life that accompanies it – is not for the faint of heart.  This is absolutely true.  But for the longest time I didn’t really understand what it meant.  Or moreover, I didn’t fully respect the ramifications of the simple choice of taking my entrepreneurial leap.

Yet now being on the other side of this experience, I understand on a deeper level what entrepreneurship all about, and how to best navigate through it the rest of my life.  As I describe some of my thoughts and observations, I hope they might resonate with you as well and help you through whatever your situation you might be in currently.

Entrepreneurs, by default, are high performers.  And high performers, by default, are hard on themselves when times get tough.  Combine those two and you could get a deadly combination.

Entrepreneurs hold themselves to higher standards than others and often are disappointed when things don’t necessarily end up as great as they had thought when they initially set out.  But you know what?   Entrepreneurship never ends up like you initially thought.  It’s messier than anyone ever imagines and more extreme than anyone ever describes.

After I experienced a failed startup I dropped into what I now can identify as a depression.  I was not – and am not – depressed as in the clinical sense, but it was more like what you would think when people refer to the last economic depression we recently survived.  It was temporary and externally triggered.  Things weren’t right and I was responding to them certainly in a negative and self deprecating way.

It was painful.  It felt troubling.  It sucked because I wasn’t supposed to be there.  Or so I thought.

What I discovered was I denied myself some truths I should have admitted at the time.  I wasn’t admitting things like: 1) I really didn’t know what I was doing, and neither does anyone else.  2) The business was not working the way we had positioned it.  2) Startups actually do fail!  3) It’s okay to walk away rather than being so committed to a project you drive yourself into the ground.  4) Your personal value is more than just your company’s success.

I did not admit those things and the result was just that – nose dive right into the ground.  Being a friend or family member you probably wouldn’t have known it by being around me.  I am a damn good actor.  I do a great job of burying the issue and grabbing another beer to selflessly talk about your challenges and issues.

Yet deep down inside was some of the worst self talk anyone could imagine.  I was not my biggest cheerleader, supporter, believer and best friend.  If you are wondering, negative self talk is not the path to success.

It took a few years to pull myself out of it.  It took me accepting the fact that although I knew I could be a great founder at some point in my life, now was not the time.  It took me putting my ego aside and accepting positions with other startups and companies where I could add value and learn more about building companies.

It seems elementary now, but letting go of the founder dream and using my skills in an another company was the farthest thing from my mind at the time.  It took me admitting I did not know it all and I need to place myself somewhere to both earn a living and learn more about the world of technology and growing a business around it.

This type of wisdom and perspective is almost impossible when you think you are worthless.  And that is exactly what people think when their startup fails.  They think since they could not make their own company work – one where they pretty much put every ounce of effort they possibly could into making it work – what’s their value anywhere else?  This and other similar thinking is obviously incorrect and ill applied.  Yet, I am telling you this is exactly what I and other founders find themselves thinking.

I have since pulled myself back together, landed a great position with another company here in Seattle and on the path to learning and earning!

The resulting mental and emotional clarity is refreshing. It has allowed me to stabilize my life and opened up space for other projects like Founders RAW, Coinme, and getting back to writing.  It has allowed me to establish myself as a mentor and advisor to other entrepreneurs, here and elsewhere in the world. It has allowed me to embrace and fully enjoy a meaningful relationship for the first time in a long time.

The lesson here is not that you can do things to avoid the founder depression.  More than likely it’s inevitable for you, me and every other entrepreneur.  The lesson is in identifying the oncoming founder depression, quickly observing its symptoms, and then finding mitigation strategies you can deploy to keep you afloat – and happy.

Entrepreneurship is not for the faint of heart.  But it is for the wise and honest.

When A Founder Crosses The Line Towards Godlike Hubris

I recently noticed a frightening trend with certain founders in the tech industry.

–> Have a great idea.  Get a few key people to join you and build it.  Launch the product and raise money from investors.  Experience massive success.   Raise more money.  Gain hundreds of millions of users. Raise billions of dollars and fight off regulators.  Have unfiltered access to billions of people’s data.  Exploit it.  Believe you are the second coming of a God.  Act like an uncaring, immoral capitalist.  Care only about your wealth and not what you are doing to everyday citizens.  And so on…

With the recent Uber misteps and observing the resulting outrage which ensued, it has come to my attention that we, as an industry, need to take a long look in the mirror.  Founders need to take full consideration in how they are running their company, the culture they are creating, the data they are generating, and the ultimate consequences of their actions.

I hope Uber realizes they are doing to their users exactly what they were furious (I assume) about the government doing to them as citizens when the Snowden files were revealed last year.

We all need to understand we are standing at an unprecedented time in the history of business and technology.  Everyday Joes now have the opportunity to create an app or platform that one day might just become indispensable to mankind.  With its use, Joe will collect billions upon billions of data points on everyday citizens – like where they are currently, where they are going, who they talk to, what they typed, to whom, what they viewed on their phones, whom they connected with socially, etc..  With all this happening, Joe will find himself directly in the middle of our society, holding a treasure trove of personal data and a devil on his shoulder just waiting for the right time to temp him into exploiting it.

I mean, it’s like big brother!

But surprisingly it ain’t the government doing these things.  Imagine what Facebook knows about you.  Couple that with your Uber or Lyft usage data.  Toss in your twitter clicks, Instagram photos, Gmail history and Google Chrome browser history.

We are doing this to ourselves.  We are the ones creating this new world of massive data collection which is resulting in unprecedented spying, snooping, breaches of security, cloud hacks and the like.

This is your fault.  And mine.  It’s all of our faults.  All in the name of making more money.

I am not here to end the data analysis, in fact I believe in it and when done correctly it makes for a better end user experience.  I also know data collection is only going to get more prevalent with the expansion of categories like the Internet of Things and connected homes.

Yet, I am urging us to start thinking about things using a different filter, or scope of perspective.  Start asking yourself these questions:

Recognizing all possible data about myself and every other person is now being collected, how to I structure my platform to preserve mankind and the humanity inherent within our society?

How do balance personalization of my technology with personal security of my users?

How do I proceed when I know I CAN do something but unsure if I SHOULD do something?

Where’s my “do not cross line?”

How can we best usher in a new era of technology applications where security is inherent within the structure of the product, not an afterthought when plugging holes after launch?

How do I shift my perspective from making the most money possible with my application towards making the world a better, more secure and protected society?

Please start thinking about these questions and more…  It’s time we call a spade a spade – WE are the ones creating the exact surveillance society we were deathly afraid of growing up.  We just thought it would be the Big Bad Government or another foreign country, not ourselves.

Please understand hubris will sink anyone who thinks they are immune to it.  You – as a founder and someone desperately wanting to change the world – can now no doubt do just that.  You and your technology can alter the history of humans here on earth.  Just make sure you know what change you are putting in place.

3 Startup Principles Every Early Stage Founder Needs To Know

I recently gave a talk to early stage entrepreneurs at a weekend hackathon in Bellingham, WA.  It was fun, challenging and educational for all.

Given these individuals were just starting on their journey, I chose to focus on things they should be considering coming right out of the gate.  Below are the three things I addressed with them and what I feel every founder needs to think about as they hack together their team and build out a first version of their product or service.

Cofounders

cofounders

The very first thing you must think about is your team – whom should be on it and whom shouldn’t.  Get it right or pay the price later.

Especially when you are starting something at a weekend event like a hackathon or Startup Weekend, it’s tempting to just grab abled bodies from anywhere so you so you can fill empty seats.  This is not advised, since the wrong person on a can bring down the entire ship.  It’s very important to fill specified roles within the team to put your company in the best position to succeed.

Here are the three positions I feel need to be filled if you are considering forming a team to build a software/app based startup:

The Developer.  First – and especially if you are starting something in tech – you’ll need a technical person.  This individual is the one who architects the product and who writes the code. Great engineers are able to balance pragmatism and perfectionism, are not averse to debugging and bugfixing, and employ a healthy skepticism of their code and the world around them. This is the engineer.

The Designer.  Second, you’ll need someone who makes the code look pretty, readable to the layman allowing for a great user experience.  Great designers understand that 90% of good design is not about the pixels, they understand basic coding and have a well rounded view of other sciences of the world.  This is the designer.

The Hustler.  Lastly you’ll need someone who can sell your product, or the one who understands how to get it in the market and found by people.  This is generally the business person, the CEO, and the Hustler.  To quote Fred Wilson, CEO’s really need to just focus on 3 things.  They set the overall vision and strategy of the company and communicate it to all stakeholders. Recruit, hire, and retain the very best talent for the company. And lastly, make sure there is always enough cash in the bank.  That’s the Hustler.

Fill those roles first, or deal with the consequences later.

Customer and User Validation

interview

The second thing early stage founding teams need to think about is finding out who will actually use the product by doing customer discovery and validation.  The knee jerk reaction of most founders is to believe they are so genius they can think up an idea in the shower, grab a few developers to build the app and then sit back and enjoy millions of downloads from all over the world.

NOT-GONNA-HAPPEN.

It’s imperative to get out of the door and talk to actual people who YOU THINK would be your end users.  You need to interview them, asking questions about what problems they are encountering, why they are having those problems and how are they trying to solve them today (they usually just piece together a few random tools to solve it until something better arrives.)  Figure out how they are doing it now so you can offer a solution 10x what is available on the market today.

And rather than trying to plan the entire thing out before talking to customers – like sitting in an office and writing a 30 page business – just start with a hypothesis, do some interviewing and testing on a few good ideas on how to solve it, and then adjust and pivot with the results you observe.  You will learn more in a week or two of testing hypotheses than months/years of preparing a well written business plan full of (mostly) wrong assumptions.

Do your customer interviews now or learn later no one wants what you just built.

Product Simplicity

tip

The last one is a biggie!  It’s paramount a founding team understands their vision, know what they are trying to change in the world and then break it down into approachable pieces to start with.

As a founder you need to think about your entire vision as a large iceberg. The challenge is to find the tip of the iceberg and only release that as the first version. The rest of the iceberg is under water and very large, just as your entire vision is in your head and not visible to the rest of the world. Some think of this as an MVP (minimum viable product) and I concur, I just like the illustration better.

Most founders make the mistake of not finding (or determining) the tip of the iceberg and thus end up building the whole iceberg, resulting in lost time, a bloated product and a lost value proposition.

For every Uber – a very simple and easy to use app – there’s thousands of apps that get it wrong and initially build a too complex product. They end up confusing users and not even getting to the point of an exponential user growth curve.

Twitter was simply a status update and following what others were updating. That’s it and people could easily talk about it and share it with their friends. Snapchat was pictures you could send to friends that disappeared after 10 seconds.  YO was absurdly simple, yet at least it was simple enough where millions of people got it and downloaded the app to mess with friends.

The key is to break down your complex problem into its essence. Know the end game and the large vision but find the simple starting point where millions of people will understand what to do with the app. Find the least amount of features and code possible to solve your initial problem.

These three principles are essential to a successful product launch.  If not paid attention to they will hinder a startup team from building a product, launching it successfully and achieving any traction in the market.

The #2 Founder Sin is Getting Married On The First Date

Would you ever consider marrying someone after the first date?

Thought so.

Since we are on the topic of Founder Sins (you can read my first one here) let’s talk about the second one real quick.  Another very common thread I see fraying from the rookie founder sweater is how quickly they are considering whom to choose as their cofounders.

“I met this developer at a networking event and I think we’re going to build something together.”

“Do you know anyone who codes?  Do you think they could help me with my idea?”

“The six of us started a company at a Startup Weekend!”

I hear these all the time.  It’s not a bad idea that people are “hustlin” and looking for skilled people to build out their team.  It’s just that it ain’t easy.

Just as dating the right person takes time for the relationship to develop into a marriage, so does a business partnership.  I am not saying you need to “court” the person for years on end, but I am saying it takes more than one event, one week or a few short meetings to grant a random person a large stake in your future company, basically legally binding the both of you.

Las Vegas Welcome Sign 3/30/11

Here’s why I know.  I have lost a cofounder myself.

In the fall of 2011 I was approached by an awesome developer – whom I didn’t know at the time – about joining the founding team of his newly forming startup.  He read an article I had written, emailed me and said we should meet.  When we met for coffee he showed me the prototype of the mobile ordering/payment stystem he was building and said he was looking for a CEO.  I was impressed and intrigued.  We booked another meeting or two and within 2 weeks we were talking “marriage”, better known as personal responsibilities, founder equity and company formation.  Before I knew it I was CEO of a tech startup (Seconds) and diving into leading a founding team I did not know two weeks ago.

But unfortunately, 6 months after that initial meeting he was on a plane moving down to SF to do contract work, leaving me to find another CTO.

What happened?

I am forever grateful for Jacques to have sought me out and single-handedly placing me on this path I am today.  Yet, in hindsight it’s clear we jumped in too quickly.  We were excited, thought time was of the essence and needed to get to work today!  Within a week or two of knowing each other we were having the “how much percentage of the company do you get and how much do I get” conversation.  I was immediately in charge of estimating product timelines, leading a team of developers, laying out our fundraising strategy, talking with the media and figuring out how we’ll make it to the next phase of the company.

All this and I didn’t even know who these people were!

I didn’t know how they handled stress (although I found out pretty quickly!)  I didn’t know how they had performed in the past on other teams and projects.  Did they run from challenges quickly or where they the ones to stick it out and find a solution?  I was not aware of their tell-tale signs of when things weren’t going right.  And I hadn’t learned how to best approach them to talk over difficult situations and touchy subjects.

In the end, I didn’t know them at all.

And now I know why investors ask about the backgrounds of the founders and how long they have known each other.  It’s very important you take the time to get to know people you want to work with in the future.  If you have a long view on your career – your entrepreneurial journey – you will see there’s decades of time for you to work on various projects and many different people you will work well with.

The thing is it’s very hard to determine that after one or two meetings.

Take it from me, it’s best to start laying the foundation for your future cofounder relationships now so that when the time comes for you to form your dream team you will already know who you will pick.

That, or get used to signing divorce papers…

The # 1 Founder Sin Is So Damn Easy To Avoid

I have noticed a trend recently as I help founders wrap their arms around their ideas and how to best get started.

They come to me with an idea – a problem they have observed in the world – and are devising a unique solution and hopefully in the process attach a kick ass growing business to it.  The problem starts when they try to get too tricky – maybe even too complex – and add all these extra functions and features to their solution.

They create Product Bloat.

This is not good.  It’s the number #1 founder sin.  Yet it’s so easily avoidable.

Why?

It’s the number 1 sin because people think too deeply about what they are trying to do.   Thinking to deeply is not actually the problem; implementing too much and attacking the entire vision right out of gate is.  They also want to be different than others in the market, so they think “well, what if we put this into the app?”  Or “such and such is doing X so we’ll just do Y so we can be different.”

The issue with that type of thinking is it takes you farther and farther away from “problem solving” thinking and puts you closer to “creating something new” thinking.  This is wrong because trying to launch a successful product without solving a clear problem in the world is very difficult, if not impossible.

iceberg

But back to simplicity.  As a founder you need to think about your entire vision as a large iceberg.  The challenge is to find the tip of the iceberg and only release that as the first version.  The rest of the iceberg is under water and very large, just as your entire vision is in your head and not visible to the rest of the world.  Some think of this as an MVP (minimum viable product) and I concur, I just like the illustration better.

Most founders make the mistake of not finding (or determining) the tip of the iceberg and thus end up building the whole iceberg, resulting in lost time, a bloated product and a lost value proposition.

For every Uber – a very simple and easy to use app – there’s thousands of apps that get it wrong and initially build a too complex product.   They end up confusing users and not even getting to the point of an exponential user growth curve.

Twitter was simply a status update and following what others were updating.  That’s it and people could easily talk about it and share it with their friends. YO was absurdly simple, yet at least it was simple enough where millions of people got it and downloaded the app to mess with friends.

The key is to break down your complex problem into its essence.  Know the end game and the large vision but find the simple starting point where millions of people will understand what to do with the app.  Find the least amount of features and code possible to solve your initial problem.

And then release it and gain users.

Once you have your users you can then figure out the next few things to place in the app experience.  But take it from me, don’t commit the number 1 founder sin right out of the gate.