Give Yourself Permission To Fail

Giving myself permission to fail has been a reoccurring thought as of late, and reading a recent post from Keen.io CEO Michelle Wetzler really solidified it for me.

After a few years in the back seat helping others in the building process I am back in the founding position. As I get back into the drivers seat I am reminded that my mental approach to this next journey determines so much of my trajectory and overall success.

If I am scared to fail, I most likely will fail. If I am worried we’ll go broke, we most likely will go broke. If I think I am not good enough to be CEO and not fit to lead a successful company, I most definitely will be those things.

BUT if I reverse that thinking I can reverse the psychology as well.  If I believe I’ll be successful, I most likely will. If I am confident in our finances, we most likely will stay afloat. If I think I am good enough to be CEO and fit to lead a successful company, I most definitely will be those things. And if I open myself up to possibility of failure I see that it is not that bad.

Michelle sums it up perfectly.

Giving myself permission to fail has been one of the most liberating, stress-relieving, and rewarding things I’ve done in last year.

The only way we can become a truly great company is if we open ourselves to the possibility that we might not be.

And you know what? It’s okay if we’re not. If Keen busts, we’ll all find new grand adventures. Some us could start a new company together, or get boring jobs at big co’s, or sail around the world, who knows, the world is full of lots of amazing opportunities.

…To give yourself permission to fail, you have to untangle your ego from your work. Having your ego tied up in your work is a handicap. You can’t think strategically or take risks when you and your personal well-being are on the line.

Basically, embracing reality frees you up to be everything you were meant to be. By not being paralyzed by what could happen, you are free to create what should happen.

This is an important lesson for founders, especially first timers who fall victim to impostor syndrome. Wikipedia defines it as “a term coined in the 1970s by psychologists and researchers to informally describe people who are unable to internalize their accomplishments. Despite external evidence of their competence, those exhibiting the syndrome remain convinced that they are frauds and do not deserve the success they have achieved.”

Another way to think of impostor syndrome is to be so frightened by your future (be it positive or negative) that you simply don’t believe you are doing the right things or are the right person for the job. You question every little decision you should make, you aren’t sure if you should go left or right. You think your peers see a different version of you, a lesser qualified person sitting in the front seat pretending they know what they are doing.  You start believing you are an impostor and thus end up failing in the end.

This is all wrong and can be mitigated by giving yourself permission to fail before you even start. That way you are free to make the correct decisions, knowing failure is just part of the process. It sounds crazy but a simple change in perspective makes all the difference. I have found the best perspective is that the world is full of lots of amazing opportunities, and if you fail at this one there’s always the next one.

That, my friends, is why I am back in the drivers seat.

Advertisements

Goodbye and Hello

I’ve contemplated writing this post for more than 3 weeks now – and low and behold – today is the right day to share what’s been happening in my life and take a bit of a dive on the new direction.

Don’t worry, there’s good news at the end.

First a little background and to make sense of why I have not written since November. Two days before Thanksgiving I was laid off from the startup where I had been working full time for a year and a half. Yep, laid off and by one of my best friends to make it even worse. Due to budgeting and funding constraints the founders let half the team go, without warning and under very unfortunate circumstances. I’ll save other details to protect the involved but although I wish them well suffice it to say I was blindsided and quite disappointed.

Thanksgiving, of all weeks!

Being on the receiving end of that sort of news during Thanksgiving week makes it a lot harder to give thanks to your family and to the world, I’ll tell you that much for sure. The sudden change placed me in a quite challenging situation for this holiday season, but one I know I can get through with support from family and friends.

I gotta be honest, it was tough to swallow. How could “I” be let go from a company I felt really needed me? And how does our ego hit so hard upside the head?

Screenshot 2015-12-16 at 5.06.59 PM

The best thing about being let go so unexpectedly is you are given back your time, which provided me a chance to reflect on the trajectory in my life as an entrepreneur and where I was currently heading. I realized I was not at all where I wanted to be professionally and not utilizing my strengths in the ways in which I wanted.

Through it all I can now honestly say I am relieved and energized. As a fighter and a survivor (and most importantly an entrepreneur) this news simply gives me a stronger fire in the belly to strike out on my own and create things that need to exist in the world. It was the excuse I was waiting for, and it served as a nudge from the world to get my ass going again after a few years hiatus.

We should be thankful for every door that closes in our face – there’s probably a damn good reason it needed to be slammed.

See, I had been working on some things during my downtime which oh-so-subtly was getting me very excited, and now I am afforded the time and energy to dive into them full time. I am here to announce I will officially launch them in early 2016.

Yes, I said thing(s).

Two. Things. I. Think. Can. Be. Really. Cool.

And. Maybe. Even. Really. Big.

I am not at liberty to let too much out of the bag yet so a few hints and previews will have to do at this time.  One of them is a really cool new experience for sports fans around the world. I am sure we all have seen the crazy growth (and commercials) of Daily Fantasy Sports and yet might not really know how to play them or feel comfortable with the whole – legal or illegal – sports gambling experience. We definitely aren’t launching another version of DraftKings or FanDuel! But we will be launching a much more lightweight, fun, mobile, and social sports experience where you can share your sports knowledge with the world during your favorite sporting events. If this sounds at all familiar, it is since we are resurrecting an idea I had about 3 years ago but then shelved it due to timing challenges. We’ve determined the time is now and are working under the hood as we speak.

The other startup is best categorized as an entertainment and media brand, and was born out of the combination of a few of my side projects – Founders RAW and Feature Friday, an event I hold in Seattle each month where I pick 5 local startups to demo to a crowd of attendees. Although it won’t be like either one of those projects what I can mention is it will be video based and web distributed. We haven’t found anything identical out there but you will definitely notice similarities to other “shows” or “series” you might see on NBC or FOX. I can also say is it will be fun, entertaining, competitive and hopefully watched by people around the world.

There you have it – not one but two new things to keep me busy during the day and up at night!

I once heard a saying:

“When you see a ship disappear on the ocean horizon, it always appears to someone standing somewhere else in the world. When you say goodbye, someone else is saying hello.”

I might have just butchered that quote but I think you get the picture of where I am at and what I am feeling right now. It’s looking like 2016 will be unlike any other year in my life. I hope it is for you too.

image courtesy of Flickr user kylehixson

Here’s My New ‘Current Projects’ Page, So Y’all Can Keep Tabs On Me

I am noticing a trend forming in my life.

I’ve been more open to starting a few new projects lately and so I decided to update this blog and create a spot where you can go to at any point in time and check out what I am working on.  You can find the link at the top right of the header menu bar on this blog.

Current Project page.

Below you can see a snippet of things I am up to right now.  More will probably come soon but this is what is happening at this point in time in my life.  Given the fact I am currently also doing some outside contract work for other companies, I am only listing the projects/companies I have founder or equity stake in.

Enjoy.

And reach out to me if you are interested in partnering or getting involved with any of them.

Current Projects

Seconds logo

Seconds is a payment system allowing you to swiftly complete transactions via the desktop web, mobile web or text message. It shouldn’t matter what method you use, the payment experience should be as quick, simple and intuitive as sending a text message.  Realizing how important ongoing relationships are between customers and merchants, and also realizing the main point of entry into our world is now through our mobile device, we see an incredible opportunity.

 

Callin'it logo 2

Callin’it is a mobile web based real-time sports prediction and data analysis platform.  Using Callin’it, people are able to test and share their sports knowledge by publically predicting – or calling – stats, plays or outcomes of an upcoming sporting event.  For instance, right now I am calling the Miami heat will have more rebounds than the Chicago Bulls in tonight’s game.  Using real time sports data, we then compare the specific call with the actual result to build out a score for each user based on the accuracy and difficulty of their calls.  If Twitter and the ‘SAT’s for sports’ had a baby, Callin’it would be their lovechild…

 

Founders Raw logo2

Founders Raw is my newest project, a video blog with conversation style interviews focused on bringing out  raw stories early stage founders experience in their rough and tumble entrepreneurial journeys.  I invite founders to talk openly over a beer or a coffee about the “truth” of how they survive and grow their companies.  We intend on slicing up the conversations and sending out daily videos no more than 3 or 4 minutes long so we all can receive daily nuggets of the entrepreneurial truth.

 

Published Books

The Agony and Ecstasy of Entrepreneurship

The Agony and Ecstasy of Entrepreneurship has been adapted from this blog, So Entrepreneurial, and placed into book format.  They are my thoughts and musings on all things entrepreneurial, meant to help you understand what it takes and how to think like an entrepreneur in today’s world.  Far from perfect and by no means the only way to go about the journey, they represent my lessons taken straight from the trenches.  Since my thoughts originated as blog posts it’s best to take them piecemeal, maybe even digesting just a few topics each day. You will find my main perspectives are around mobile, digital and internet technologies but the principles can be applied to any other entrepreneurial focus.

Spring Is In The Air And Something New Is Upon Us

This post is part wind-down announcement and part new product news.

We started Seconds (back then called Order SM) in September 2011 with the goal to experiment around mobile – text ordering at local restaurants.   Our assumption was people would want to simply text “burrito” to their local mexican restaurant and then be able to swing by and grab it without having to wait in line for their food pay with a physical credit card.  Everything would be taken care of in the background on the web.

We learned a ton, but the biggest thing was both merchants and customers really liked being able to just pay for something by sending at text and not mess with all the other communication crap, so we ended up moving towards specifically focusing on a mobile payment system.   We changed the name to Seconds and rolled it out in Jan 201n2.   We saw a dramatic market interest in our unique take on payments, receiving inbound request from almost every continent in the world.   Unfortunately, we weren’t able to secure capital it required to scale our team and out product and so we basically stalled out at the end of the year.

Rather than being a Zombie-startup, I decided it was best we make better use of each members skill set (go get paying gigs) and wind down the operations on Seconds, as a mobile payment startup.  This means we are not taking new customers or putting in new work around the product.  It also means we are retaining the IP and tech, placing it on the shelf for a while as we determine the next phase for our ideas.  As I said to the team when we made this decision, “with each passing day, people will only get more comfortable with mobile payments and we’ll make more and more mobile payments as the months and years go on.  I don’t think this is the end of the line for our ideas, just not the right time and place for Seconds as it is today.”

This was definitely a tough decision and one I probably put off for a few months not wanting to accept the reality of the situation.

For all you who know me personally you will be quite familiar with my challenges as I built Seconds.  It is not easy to be a founder, no matter how “rock star” it may be described nowadays.  It’s lonely.  It’s stressful.  It stretches you in ways you will never imagine.  It mentally challenges you to the point where you actually think you are crazy (and probably could be) yet just normal enough to not be committed.

Frequent readers will recall my many posts on what it’s like to be a founder.  Rollercoaster is an understatement, mainly because when you get off the ride you say to yourself “wow, that was crazy fun” and then simply go back to your normal, unaffected life.  No so when you jump head first into your life as an entrepreneur.  There are scars from this journey that will take years for me to fully recover from.

With that said, we are not finished.  Strangely, I am scarred yet more excited and more prepared for future success.  A backstory will help you understand what is about to transpire from here on out.

About 7 weeks ago the Seconds team took the Super Bowl Weekend and entered Sports Hack Day, a 3-day hackathon to see who can build to coolest thing using sports oriented data.  What a weekend.  It was full of late nights, massive brainstorming and beer infested hacking.  Although we didn’t end up winning any prizes or awards, we emerged from the weekend with a kernel of a cool idea that as sports fans we just wanted to use as we went about our life.

“What if you predict – or make a call – on any stat, play or outcome of a sporting event, and in Twitter fashion simply be able to shoot it out into the social sphere telling the world you think ‘X’ will happen in this game.  If correct, your score would go up.  If wrong, it would go down.  You could then challenge friends with a simple finger swipe on your phone and then go back to watching the game.  And what if we could then determine who knew the most about sports by this running number, similar to a Klout score but for sports.”

We liked the idea so much we decided to continue to work on the concept after the weekend concluded.  I couldn’t get it out of my head and as a sports fan I wanted to use it – like really bad.  I don’t normally play fantasy sports leagues because it feels like such a commitment of time and mental energy.  But if I could simply make a few predictive calls on my mobile as to what I think will happen in the Bulls vs Knicks game tonight, and show my friend I know more about sports than he does, I’m into that.  It’s addictive.

So the 3 of us wondered what it would look like and continued to build it out.  It ended up more of an undertaking than we realized and has required many late nights over the last month.  We are now almost ready to release it to the world and see what happens.  That is all I will be saying until we announce the release very shortly, but needless to say we are interested to see what the world thinks.

As for me, I will be hired here soon and will have new daily responsibilities with another company.  Am I excited to join another company?  Yes.  Do I wish I was full time (and paid) in my own company, not having to work for someone else?  Yes indeed.  Will it just take a little more time until that happens?  For sure.  Will I give up on pursuing my creative side as an entrepreneur?  Hell no.  Do I realize my time building Seconds is pretty much the only reason I will be hired into this next position?  Yep.  It’s not lost on me all this has been worth it no matter the financial outcome or the pain associated.

Spring is in the air; no better time to emerge towards a new direction and pursue an exciting new opportunity.