I recently sat down with Amy to talk about pitching at Founders Live, drones, and balancing hard work and a personal life. It was an educational and enjoyable chat. Watch the 35 min conversation below.
Category Archives: Founder
Podcast: My interview on The Startup Sessions with Michael Knouse
I’m very humbled to share a recent interview I did as a guest on the Startup Sessions Podcast, where I talk about my current projects and how I go about the craziness of founder life. I enjoyed my conversation with Michael Knouse (he was a recent guest on Founders LIVE as well!)
I hope you find it helpful.
Creating Your Own Wake
As a founder your survival is a function of how you create your own wake.
A wake is the region of recirculating flow immediately behind a moving or stationary solid body, caused by the flow of surrounding fluid around the body. There is formation of vortex in the wake which is the region of low pressure in it.
…The formation of these waves in liquids is analogous to the generation of shockwaves in compressible flow, such as those generated by rockets and aircraft traveling supersonic through air.
Circulating flow.
Vortex.
Pressure.
Shockwaves.
If you read the entire definition you’ll likely get lost in a hell of a lot of science but those are the words that jump out to me when I read the definition of wake. It doesn’t just apply only to water either, if we could see movements of air we’d be seeing the impacts of wakes and shockwaves all around us.
To me, in human terms wake simply means your lasting impact on the world around you.
I have been thinking about this phenomenon recently since I made the leap back into entrepreneurship as a founder, (re)discovering all the painful and challenging issues you deal with as you are just starting out. So many things are working against you and the inertia of the world is quite similar to the inertia of water. A boat doesn’t create a wake unless its moving. Same for us. Forward progress in life requires some sort of energetic force to drive you forward, pushing against the inertia of the world and creating a wake that ripples outwardly away from you and positively impacting others around you.
There’s some social science for ya.
One of the most important lessons I learned in the last couple of years is you can make the entrepreneurial path a little easier by creating a wake around/behind yourself. This is not easy, because it requires effort and energy to do things we generally don’t want to do. Going above and beyond our normal comfort zone to stand out is almost the antithesis to what we as humans feel we want to be doing each day/week/month.
But standing out – creating a wake impacting others – is what is required of you as a first time founder who is desperately wanting to make it to the next level. That or get lost in the thousands of others vying for the same attention, money and position.
What would a wake look like in real life? How would it involve humans, social interactions, business decisions, etc?
I find the key to gaining an edge when just starting out is finding specific actions to take to create a wake in an industry – shockwaves that keep spreading and impacting people you might not even have direct contact with.
Start writing on topics people in your industry might find interesting, posting them on social media and guest posting on other media outlets. Who cares what you write about (okay that’s kind of harsh but you get what I am saying) and what others might comment on, just having a voice and putting it out there places you at the top 10% in your industry. Be consistent in your writing efforts and don’t worry your audience will find you. Create video or other visual content which is entertaining and educational and that others can share with their networks. It doesn’t exactly matter what you record and put out, it just matters that you start and don’t stop so others start to recognize you. Organize local events and meetups around relevant industry topics so you can help others connect with each other. Be seen and be known. Work on and release products which are both interesting and have high potential to change your industry. Who knows, you might learn something new! Carry yourself, shake hands and talk in a way where people will be impressed.
These are the things people remember, they are what people share with others and what sticks in a room once you leave. That’s your wake.
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.
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?
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
Coasting To Perfection
Am I doing all I can each day to reach my own pinnacle in life? Have I done everything possible to become the person I was created to be or am I just coasting along the highway…?
A post today piqued my interest and spurred this intense inner monologue. MG Siegler writes about a recent SI article on Michael Phelps which details his comeback and rehabilitation from alcohol related incidents. The article touches on a variety of events in his career but what jumped out to me was a very interesting and possibly troubling assessment by Phelps himself, where he simply admits he has never given it his all. Ever. Even after numerous Olympics and all the medal records he feels he under-performed and still has his best inside him. Siegler ties that thought back to all of us:
“we don’t often hear about someone at the pinnacle of what they’re doing also failing to give their all — and yet, that’s clearly the case with Phelps….. And so in a way, I think that’s a more interesting point from which to look inward. If you’re really fucking up and squandering your talents, it’s pretty obvious for everyone to see. But what if you’re only not “giving it your all” and coasting on doing the minimum to still be successful — even very successful? Or maybe not even the minimum, but something less than all you’ve got. I think a lot of people are guilty of this. Maybe even most people. Certainly I am, in some regard.”
So I ask you, are you just coasting through your life?
It’s a troubling thought if you really consider the question when its asked another way: will you ever reach your full potential with your current output of energy, focus and determination?
I ponder this question quite a bit and maybe it’s the reason I have a number of current projects/companies ongoing in my life. It’s almost as if I can’t not do them. I don’t want to ever look back and realize I could have done more, that I should have applied myself more fully to the things and people in my life, and that I coasted lazily while others looked upon me with slight disappointment knowing I was fully talented and capable of greatness but in the end never doing anything worthwhile.
Wasted talent they’d say.
This is why I push myself to write even on days when I don’t want to or don’t feel like it. I want to follow my writing talent as far as it will possibly take me.
This is why I get in front of the camera and shoot more Founders RAW conversations. Setting aside the enjoyment I get from doing them it’s not easy being comfortable in front of a camera and I believe people need to hear the messages we are putting out. I also want to follow my talent in media creation as far as it will possibly take me.
This is why I get on stage in front of hundreds of people each month and host Feature Friday events in Seattle – a monthly event which highlights 5 new up-and-coming area startups. This pushes me to become very comfortable on stage in front of crowds and calms the public speaking nerves, a wise move given public speaking is the #1 fear in the world.
This is why I push myself to build new apps and create whole new companies. I don’t ever want to find myself out of the loop on the latest trends, as well as sometimes it just takes a few cycles before the big idea takes hold.
This is not rocket science but I do these things so that I get better at them until a time comes where they are second nature to me. This is the 10,000 hours stuff Malcolm Gladwell talks about. It is said by the time the Beattles led the “British Invasion” with Beattlemania and brought their music into America they had already played together as a band live so many times they had eclipsed their 10,000 hours threshold and were very very tight as a band. That’s why they were so damn good so early on.
But it didn’t come overnight.
The Beattles believed – as I am starting to now – you are only as good as you choose to be. And “to choose” means you determine to do whatever it takes, however long it takes, with whatever means you have at your disposal to achieve you potential. Anything less is just cheating yourself and the greater world in the process.
Some have it easy you might say. They are naturally talented and without doing EVERYTHING THEY CAN they turn out to be Olympic champions and record setters. LeBron James, Michael Phelps, ect.. Simply more talented than anyone else. I say good for them.
But I am more impressed with the one who wasn’t God gifted with the most talent in the world yet works so diligently at their craft they become one with it, they become the legends we read about. The Wright Brothers. Steve Jobs, etc. The ones who came from nowhere, with no money and no connections, no Ivy League schooling, no Silver Spoon or lucky sperm club card to show off.
These people will it into existence. They are the ones we love to read about and crave to hear speak in public.
My guess is you fit that bill just as I do. So do yourself a favor each day and ask yourself if you are giving it your all – and be honest with your answer. My guess is you’ll be surprised at how much farther within yourself you can dig.
Do Something Everyday That Terrifies You
Here’s some advice that might be scary to you: Do something everyday that terrifies you.
It’s a simple sentence yes, but its consequences reach far and wide. Having courage to do things that scare you is the essence of growth and progress, in both your personal and professional life.
I noticed this phenomenon recently in my own life when I chose to start meditating every day. Before I started, I viewed mediation as a foreign activity, something only eastern religions practiced. But actually, I was scared about doing it for some weird reason, namely because it was new and different to me.
Yet I decided to lean into my fear, push it aside and dive right in. Five months later and I am still going strong, maybe missing one day per week on the weekends when something comes up in the morning and I am not able to sit quietly. I can’t even describe the benefits I have enjoyed and the new growth opportunities I have opened up simply because I am sitting quietly each day and contemplating this crazy world we live in.
I also learned doing terrifying things are good for the soul when I reach out to people and sit down with them for a Founders RAW conversation. More and more of my guests are noteworthy people who have founded well known companies or are successful in their previous ventures.
I think to myself “they get hit up all the time so why would they answer my email? And why would they want to talk with me anyway?!”
But you know what?
I send it anyway.
And they answer it!
Meeting set, great conversation had, sweet new Founders RAW video for you all to watch, and new contact/friend made.
All because I chose to be uncomfortable and reach out to someone who might turn me down or not respond to my request. It’s crazy how your mind twists reality to scare you from doing things each day that would totally change your life. You have to acknowledge the warning but then push past it.
Ask for the sale.
Ask the guy or girl out.
Ask the investor for more money.
Jump off the cliff into the water.
Write the blog post you’ve been thinking about.
Smile at the stranger.
Talk to the stranger.
Post the picture.
Build the prototype.
Recruit the team.
Start the company.
Ask for the raise.
Join the new company offering you a promotion.
Move to the new city if you feel the pull.
Guys and girls – the principle works. Do something new and scary each day of your life and you’ll be shocked at what happens next.
People Are More Impressed With Who You Are Than What You Do
We’ve all been asked that dreaded question at a networking event.
“So… what do you do?”
I drive myself insane wondering why people lead with that question in social situations. My guess is they are just nervous and it’s the first and easiest thing that comes to mind and then out of their mouths.
Yet, it’s the dumbest and worst question to lead with once you shake hands with someone. It shows the other person you are about to judge them and looking for the lowest hanging fruit to make your snap judgement. So do yourself and the person in front of you a favor and don’t ask it anymore.
So what SHOULD you ask?
Anything. Except for the above question anything is fair game. Ask about their clothes. Ask about their background or where they came from. Inquire about something unrelated to the topic of the evenings event like the weather, local sports team, the coffee shop where you are sitting, a funny off-the-cuff joke about the random people you are watching. Really, anything will work here. Absolving yourself of the “what do you do” question will invariably raise you right to the top of the list of people the other person wants to converse with.
But why is this so?
The “what do you do” question makes people feel like they are being interrogated. Especially if the person you find yourself talking with has recently made a huge life change and is in between jobs or startups. Take it from me, when in that phase of life this is the last question any of us want to answer. And the thing is you never know who has recently made that decision or is currently in that phase so better to be cautious and not take a salt shaker and dump it on someones fresh wound right out of the gate.
The “what do you do” question also makes people feel uneasy since its origins can be found in us humans trying to compare ourselves to others. Instinctively, our goal is to find someone who we feel superior to so we can make ourselves feel better, even for a brief moment. If I ask you what do you do and you tell me “I’m a lawyer” or “I just sold my startup to Google” I now know where we stand economically and socially. If you respond with a lower status job description I also know where we stand and feel better about myself.
But what about the people who ask the question only so you ask them the same question so then they can pitch you their business? Same result holds here: not a good idea to lead with your elevator pitch to a stranger that didn’t ask for it. I don’t know about you but I don’t want the first interaction with every person I meet to be a pitch session about what they are working on and how I can get involved. This is also a very shallow and quite self-serving interaction and again puts people on the defensive.
What I have found works best is to be genuinely interested in other people, and ask questions about them and what they care about. Becoming interested in others is quite easy if you don’t lead with “what do you do” questions. I try to challenge myself and get creative in how I converse with people, how much I can get them to talk about their ideas and passions. Initiating conversations without asking about profession or job shows the other person you are genuinely interested in their story and them as people, not just about professional comparisons. One or two great questions or comments unrelated to their profession can jump start a quality interaction with pretty much anyone. I have found this is the best and quickest way to illustrate who I am and my inner character without saying a thing – outside of asking the intriguing questions. The less I say the more I listen – and thus show who I am – resulting in a strong trusted connection with the other person.
The crazy and counter-intuitive thing about this strategy is once you start a conversation with another person not asking about their profession the other person will inevitably bring it up, but on their own terms. And since you didn’t come across as aggressive or interrogating you will find they are very engaged in the conversation and will walk away thinking you were one of the best conversationalists they have ever encountered even though they did most of the talking.
And in this way you will find each and every conversation is a way to learn something new about the world, something new about another person and a fun way to add to your wisdom of the world.
Seek first to understand, then be understood.
You Gotta Give To Get
I have noticed a trend within myself recently: The more I help others when they ask the more I tend to get from others when I ask.
I am not sure if its a natural phenomenon, me being more attentive to others needs or others starting to be more in-tune with where I sit in our industry. Regardless, I discovered really cool things happen when I am more open to giving to people.
The giving I am referring to is of my time, relationships and mind-share. This realization has come to my attention as younger founders or less experienced entrepreneurs more frequently reach out to me for help, perspective or introductions. This is natural, fine with me – given they are respectful in their ask – and something I enjoy doing.
Yes, that means I’d be open to responding to you too if you need it!
Interestingly, many times when I meet with someone they are very thankful and surprised with how generous I seem to be. My response: I feel it’s what we are supposed to do if we are farther down the road in our journey than someone else (referring to providing guidance and intro’s if the situation calls for it.) All I ask is they do it too once they are at a level where they can help others in this way. Most first time founders don’t run in the same circles as investors or wealthy former founders, and they have to get connected somehow, someway. Founders getting introduced to well known people, investors or customers was how pretty much how this whole industry got started. Let’s keep it going…
The interesting thing I notice is how much natural karma is created when you are genuinely more open to helping people when they reach out.
The adage I now live by: help people first and people will no doubt help you.
The Tales We Tell Ourself About Failure
One thing we humans do really well is self doubt.
In the last week I have had two separate conversations with fellow founders about the grave situations their companies are in, how they are staring “defeat” right in the face and don’t really see any other option than to move on.
Both people are down and out right now. And rightfully so… They have put years of blood, sweat, tears and money in pursuit of their dreams. They feel troubled with the fact that they didn’t succeed in the way they felt they could, didn’t build a meaningful and growing company. I know what they are going through, I have was there a few years ago and had a hard time knowing when it was time to pull the plug.
My advice to them is this:
It’s okay. You think the company (and you) are a failure because you have to move on and go do something else. You may have put your self worth into the company so much so that as the company faces a failure in operation you are feeling like a failure in life. You might be feeling a bit embarrassed because of all the things you said to your friends, family, coworkers, and industry partners now make you look at best untrustworthy, and at worst fraudulent.
These are all normal fears and feelings. They are all accurate and a normal part of the grieving process of a failed attempt at a startup company. But these are all fairy tales we repeat internally.
The reality is the very fact you set out and tried something unique and different is the success in this story. The very fact that you had the courage to attempt something most people would be afraid to do is the success. The fact that you were looking to be part of the solution rather than part of the problem is the success. Most likely your entrepreneurial decisions inspired at least one other person to jump up and start their own entrepreneurial journey. And further, maybe that person and their project turns out to be a massive success, impacting millions of people around the world, lots of that due to you. You may never know… but it’s a possibility isn’t it?
Many people lean on the stat that something like 75-90% of all startups fail, they don’t reach a point of self sustaining profits. I feel this stat is misleading since it only measures financial outcomes of each entity. Is the company alive, or dead? Red or black? Running or shuttered? Successful or not?
A better measure – albeit much more difficult – is to evaluate the impact each person and their endeavors have on the people around them. I guarantee if we were to measure the impact and success of each founder who ventures out on their own by looking at how they affected, influenced and inspired others we’d be talking about a whole different number. I bet it would possibly be the inverse, which would be quite inspirational. We’d be saying something like “Only 10-15% of startups really fail to impact the world so you must go and do it!”
To all those who are currently struggling with what to do and which decision to make for your company right now, heed this advice. The only failure in your situation would have been not choosing to attempt the impossible, since that is the only reason you are able to sit in the chair you are sitting in right now, reading this on your device you are holding in your hand, sipping the drink you are tasting right now, and driving in the car you just drove in.
Success is simply choosing to attempt the impossible and inspiring others to do the same.
Is Depression Actually Normal?
I wrote a post recently touching on my brief bout with Founder Depression. As a result, many mentioned it on Twitter or reached out to personally thank me for writing it and to let me know they also struggled with it.
This sparked a few thoughts: “Is depression actually normal?” And “if everyone deals with some sort of depression in their life then what can we do about it?”
I have come to realize depression is something all of us deal with at one point in our lives. It should not be taboo or anything. It should be addressed and talked about openly as part of the entrepreneurial education process. As founders, we encounter depression usually from external events such as failure of a business or a negative outcome of something in which we had hoped for when we first started out.
I am starting to realize being a great entrepreneur starts by perfecting how to handle the shit in your life. Because it hits the fan waaaaay more times than you plan. I have also come to understand the successful ones figure out how to identify the piles in the road ahead of time, and navigate accordingly before they hit something fatal.
Athletes strength train and stretch in prevention of injuries. Why are we not doing this in the startup community? Why are we not helping people to prevent what inevitably happens to those of us who strive for more?
The point here is to understand its not IF it will happen, its WHEN it will happen to you. And then go into your entrepreneurial journey armed with the idea that you will at times feel very down about yourself and your company. This is reality and this is serious. If a founder doesn’t take it as such they are potentially setting themselves up for disaster.
Like I did.
In a recent conversation with my father we touched on this. I noted that only when I realized I had dug myself into such a deep hole emotionally could I fully grasp where I was and what I had to do to get out of it.
I realized even though I was not in control of external events I was in control of my thoughts, feelings and internal dialog. And I was the only one who could bring myself out of the funk in which I had brought myself into. I had to consciously think and make decisions that would place me in a neutral or positive place.
No more negative self talk. No more whoa is me. No more pity parties and thinking I had let myself, my family and my community down. I had to stop fighting myself, put my ego aside and choose a different path. One that – although it has a few more twists, turns, roundabouts and curves to it – is leading me into an even better position than when I was CEO of my own little startup.
The fact is, if you are a high performer and things don’t turn out exactly the way you planned you will naturally tend to go into a dark place. Those sort of feelings will not help you move forward in any way whatsoever, so please think now about how you will respond once you sense yourself going down.
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.
How To Approach Investors
I was asked a straightforward question by another founder recently. “How should I approach a potential investor?”
Although it’s a straightforward question, the answer is quite nuanced and depends on the specific situation at hand. All investors are different and appreciate being approached in varied ways. So given that, here’s what I responded with through email. (I have removed any details that would suggest a certain person or industry)
A) Connection
You need to find someone who you connect with and have a similar view on things. This is why I suggested talking with people that are already into ____________. They should at least “get” your idea and thinking behind it. An investor that usually puts money into software companies probably won’t get it.
So I think you need to continue to look deeper in that community. But you can’t just send an email and ask for their money right up front. Everyone’s knee jerk reaction is no. This is the biggest mistake people make, just like the guys that hit on the women at the bar. Instant turn off. You need to do what you are doing with me and get to know them, allow them to get to know you and your idea. Don’t worry about “giving away your idea” as I have learned it’s better to connect with many people and hopefully there’s a possible business relationship than keeping your mouth shut and then nothing happens. Ideas are a dime a dozen… work on extending your relations with people in the industry.
B) Early success
Most all investors need to see early success indicators. That is why if you can show some early traction as well as some profit, they investors are way more willing to put in some money to help it grow. Although ideas are a dime a dozen, that’s all they are. But a product that has shown some early promise is music to an investors ears. They need to be able to see it, feel it and touch the prototype, or in your case see your early small tests as successes. Once you can show them real numbers you then build out your model of future projections – based on your real numbers – and show them how their money will be multiplied.
C) Trust
The last one is you need to find people who you trust, and who trust you. This goes back to a) in the way I say find someone you connect with. Turning the tables and looking at it from their point of view…. some random guy is emailing them and asking them to put money in something they don’t know anything about. Basically, they don’t trust you. So you need to work on finding someone you can work towards trusting, and he can work towards trusting you. This takes time.
That’s why your lead into the relationship is more like “hey, I have some ideas I want to run by you, I would appreciate your perspective on these ideas…” Don’t even mention money for the first few interactions, and when it comes up you can say something more like “to scale to the level we want to we would need some capital investment. I’m starting to look around, do you know anyone who would be interested?”
Finding investors to put money into your company is hard enough, make it easier on yourself by doing some legwork first.
The Road Ahead
I have often said being an entrepreneur feels like you are a circus clown on a unicycle, riding on a tightrope and juggling 5 different things at the same time.
Yep, that’s pretty much what I am doing right about now and it feels a bit crazy. My hope is that it settles down a bit as we get these things in motion.
Below is a glimpse into the road(s) I am looking down right now and if all goes as planned it will be most of my career focus. They might be general – on purpose – but they are the trends of the next 20 years and industries I am both interested in and feel are at inflection points historically.
Payments – mobile and otherwise
Most of you know I have been in the mobile payment space for a few years now. Our first try with Seconds payments didn’t go as smoothly as we had hoped. BUT, we learned something really valuable – remote mobile payment/billing is going to be huge.
We learned this from realizing the act of forcing someone to make a payment with their mobile device while standing in line at a coffee shop/target/local market/etc actually takes more time and is more complicated than giving cash or card. The end solution just has to save all parties valuable time. It will be years before this becomes commonplace and who knows how much it will take (billions invested) to make it happen.
But, you know all those letters you received (or still receive) from utility companies, munipalities and other entities basically telling you 1) here’s the total you owe and 2) here’s where you send the check or 3) log in at this url to pay? Well, we can save people a lot of time and hassle with a new direct mobile billing experience. That can all be achieved by a simple notification on your mobile device informing you of a balance due, should you opt into receiving it. And with your payment credentials already in the system all you need to do is simply respond with “pay” and it’s all taken care of. Business gets paid, consumers account is cleared, no re-entering payment credentials… Simple.
Yep, we got that in the pipeline.
Cryptocurrencies – Bitcoin
Since I am in the payment/financial space I have been watching the rise of Bitcoin for some time now. It’s very interesting to say the least and everyone has an opinion.
Here’s mine: the world needs a new mechanism for payments to flow around the world and Bitcoin feels like it’s the one. As both a currency and a technology, it will not only transform money as we know it is but also its place within this new digital/mobile/worldwide economy. As a speculative commodity, no one knows if the value will hold ($500), massively increase ($100k) or completely tank ($1). We’ll have to see, but my guess is that its value will not be the greatest impact Bitcoin will have on our world. As for regulation, the government will have to figure out how to play nice and guide it towards positive impact on our country and world. I don’t see it completely taking the role of the U.S. dollar so I think that argument is flawed and used politically to take a side, similar to the silly spat between Republicans and Democrats in this country.
So please remember today’s incarnation of Bitcoin will not be tomorrow’s… merely turning your head and shushing the noise is the wrong answer. Just as there were many naysayers in 1994 and 1995 about the web, we are seeing something truly transformative take shape and I don’t want to look back in 10-20 years and kick myself for not getting involved in the movement.
That being said, yep…. the road also includes some things around Bitcoin. It should be an interesting year.
Internet of Things – API’s of life
Another interesting phenomenon starting to take shape is the so-called Internet of Things. I am not sure I like that term but we’ll agree it means a world where everything is “smart” and “connected” to everything else via the web and sensors. Just imagine what can be automated or programmed when devices and objects – previously “dumb” and non-economic actors in our world (tables, chairs, driveways, houses, bikes, cars, etc…) are brought online and provided an identity. Then include an economic identity (hhmm like using something like bitcoin…. now are you are starting to get it?) and allow humans to communicate with and pay and be paid by machines. The possibilities are endless.
Even more basic is the ability to start automating things in your life. If you have heard of IFTTT (If This, Than That) you know what I am talking about. Basically, it means you can set triggers in the world, that when activated, will result in an action you previously determined. These triggers are offered by various web based components in the form of API’s (Application Programming Interface) which allows you to tap into and easily integrate with other technologies. For example, if I leave the house (known because my GPS on my mobile) then lower the temperature in my house by 5 degrees. If Bitcoin falls below a certain price ($300), purchase X more for me. You get the picture.
Yep, something like that’s in the works as well.
Health Technology – Wearable devices
An amazing area for innovation using connected and wearable technologies is health care. We are wondering what is possible once people wear something(s) that are able to monitor and collect up to the second data regarding our vital heath?
Given my background in health I am immensely interested in the future of preventative health tracking, and we are in the process of laying out our first attempt at it. Imagine wearing a small device that, when it senses a certain vital sign has fallen out of the standard deviation for this specific individual, sends a notification to family and medial team with actionable instructions? Imagine how many heart attacks could be prevented if we knew the second someone was “about to go there”? Now, I know this vision could collide with the scary notion of Big Brother NSA, but I have a feeling the pendulum will swing back toward a better equilibrium of personal safety and information security.
Yes, although it might be a bit on the horizon this is down the road for me as well.
Content Creation – Founders RAW
The last one is video. We are starting to see more online video created and watched each day, month and year. And it’s easier than ever to create and distribute video, especially through social media. I intent on continuing my work on Founders RAW and experimenting with online media. Founders RAW is a great playground, since it falls inline with entrepreneurship and founding of technology companies. My goal is to continue to talk to founders and put out high quality content for all of us to enjoy and benefit from. It will be interesting to see how content and video grows from here, how we all can take part in it.
So there you have it.
If you are tired from simply reading it, how do you think I feel? My mind is spinning with all these possibilities and opportunities. While it may seem like I have some random form of ADD (might be true) it’s more like all these opportunities came to me in the last few months. Some are being built as we speak. Some are on their way. Some are in brainstorming and prototyping stages. Some might not make it into production, but all are well thought out and well positioned to become something great in the future. I hope to be a part of them all.
It’s never been a better time to be an entrepreneur.
Image by Flickr user oatsy40.
A Vacation From Writing
After almost 3 years of consistently posting 3-4 times per week, I am taking a break.
You may have noticed I have been less frequent in my writing lately, and that is indeed true. I have quite a bit of things going on in my life and business(es) and it seems like I cannot find the time and mental clarity to get a post together.
I recently noticed myself getting anxious as I realized I had not been writing as frequently, and I don’t like to get anxious. I would think of great topics for posts and then wouldn’t get around to putting pen to paper (er.. fingers to keyboard?)
I finally sat back and thought to myself “why not just make it official and take a break so you don’t feel like you are struggling to write?”
So I am taking a vacation from writing.
I have no idea how long this break will last. It could be weeks. It could be months…
But have no fear, I will continue to post/update videos on Founders RAW each day since those don’t require much time each day, so you can head on over there and get your Nick fix.
Mahalo.
Chop Wood; Carry Water
I recently sat down for a great lunch conversation with Nick Soman, a founder friend of mine here in Seattle. Nick is the founder and CEO of LikeBright and a TechStars graduate.
As we were reminiscing about the founder life he said something quite profound.
Chop Wood; Carry Water.
It’s obviously a nod to early times in society where life depended on staying warm and keeping hydrated. People couldn’t just hide in their cave if something went wrong, they would eventually die. Or if successful, they couldn’t just rest on their laurels when something went right. Simply put, life goes on. They needed to keep chopping wood and carrying water no matter what.
I believe that thinking applies today. Actually, the principle applies even more today than ever since we have so many distractions in the palm of our hands and right in front of our faces.
If you have experienced something exhilarating, exciting and greatly advantageous for you or your business, the question is what do you do next?
You need to chop wood; carry water.
If you are down and out, struggling with life and fighting the feelings of disappointment the question is what are you going to do tomorrow?
You need to chop wood; carry water.
The point is you need to stay alive. You need to keep working. You need to keep doing what got you that advantageous opportunity in the first place. And if you have hit a negative streak you need to just keep going, things will come back if you get back into the game and work on the basics.
Successful people make it a habit to be steadfast in their ways – they don’t get too high when things go well and they don’t get too low when things get challenging. They stay even keel.
They keep chopping their wood and carrying their water no matter what happens to them.
I like that. And it’s what I have been telling myself lately as I have been enduring some exciting times.
I hope you do as well.
What’s Your Story?
Have you ever thought about this question?
“What’s my story?”
I attended an event last night where the speaker talked about startups and creating a story around them as you build. He then had a slide that simply said “what’s your story?” meaning what’s the company’s story you will be telling others, such as future employees, investors, and customers. His whole point was a major differentiator between your company and all the others is the story behind it. I liked where he was going with it but I think it can be taken to a much deeper level.
What’s your story?
Do you know the meaning of the life you are living right now?
Why are you doing what you are doing?
Does company you are starting or the job your are current in have a strong story and purpose behind it?
Why does the company exist?
Does it connect with people on an emotional level and add value to their life?
Are you doing something just to make money or are you also creating value in the world?
Yes, these are deeper and more serious thoughts than revenue models and exit strategies but they need to considered or one day you’ll wake up wondering what the hell you have been doing for the last decade or two.
I don’t know about you but I don’t ever want to have that feeling. I’m not perfect and nowhere near where I want to be in this department but I am glad I am reflecting on thoughts like these. They are definitely influencing my next moves. I hope they help you as well.
If you need some help in this area, listen to Scott Harrison tell his story about Charity: Water.
Who Inspires Me?
You might wonder who inspires me as an entrepreneur and a writer.
There are many, but one person is Mark Suster. He is a previous two time entrepreneur – sold his last company to Salesforce – and is now an investor and has been with with Upfront Ventures for about 6 or 7 years.
He’s great because he views startups from both the investor AND the founder perspectives, hence he writes at Both Sides Of The Table. His straightforward tone and no BS attitude is something I have taken to my own words. Like him I feel truth, honesty and controversial topics should be embraced by an influencer. Ya’ll deserve it.
To get an idea of who Mark is, here’s a recent interview with Sarah Lacy of PandoDaily.
If you are an entrepreneur I suggest sitting back and taking some notes. It’s long, but chock full of gems.
5 Tough Questions To Ask When Starting Your Company
So, you want to start a company?
Awesome. That’s a very exciting decision but first you must make sure it’s the right decision.
Startups are hard and have been referred to as “a full contact sport” by others so deciding to be a founder is only the right decision if you are ready and willing to except what comes with founding a startup.
Coincidently I am going through this same thinking process right now. Even though I have started a few companies before, I find myself at the starting line once again evaluating a new “dent in the universe” idea with a fellow co-founder. Here are five questions I am asking myself right now to help determine if it’s the right decision. I believe they can that help you too along your path to starting your next company.
Am I really an Entrepreneur?
Risk is the heart of entrepreneurship — which is defined as “the pursuit of opportunity without regard to resources currently controlled.” Your relationship with risk is the sole determinant whether you will succeed or fail as an entrepreneur.
Are you ready to take a risk? I encourage you to think of yourself as an entrepreneur in the adjective form, not a verb. What do I mean? Well, during my first startup I struggled – a lot, and for a long time – and it really bothered me because I didn’t really know why I was struggling.
Then it finally hit me.
It all changed when I re-thought what the dream actually was. I realized my dream wasn’t about what I was working on at the time, but more about the person I was becoming in the process. The dream is about being an entrepreneur – the adjective – not the noun.
Entrepreneur – noun. A proprietor who owns their own business. A title.
Entrepreneur – adjective. A person who embodies the qualities of being Courageous. Risk Taker. Innovative. Persistent. Agile. Intelligent. Savvy. Strong. Personable. Creative. Excellent. Fighter. Winner.
Once I realized all I needed to do is change me perspective of who I was, everything changed. Also, I realize being an entrepreneur was all about how I viewed and embraced the world of risk.
Fellow entrepreneur and billionaire Sir Richard Branson follows a principle called “protecting the downside,” which means that by looking at any situation and determining all options before making a decision, one can identify the worst case scenario and work backwards from there to find the optimal route forward. Protecting the downside is really just identifying and understanding risk.
So your first step is all about asking if you can handle a world full of risk.
Am I ready?
Once you determine you are cut from the entrepreneurial cloth, you must ask yourself if you are actually ready. Is it the right time to embrace a life of high risk and high reward?
Question yourself on things like: Do I have more important responsibilities, such as family obligations, debt to repay, volunteer work, coaching youth sports, or things that require your time and energy?
The reality is startups take pretty much all of your time and energy. They are like rockets going to space – it takes A LOT of energy to take off but based on physics it takes less energy to keep going as it gets higher and farther away from earth.
Step 2: sideline some of these major responsibilities if you are to start a high growth company, and then pick them back up once things really get going.
Am I passionate about the idea?
Once the commitment has been made and you believe you are ready to take the plunge, you should ask if this is something you are really interested in, passionate about, and willing to give it 5-10 years of your life.
This is somewhat of a controversial topic. Some say founders need not be passionate about a startup, simply because only possessing passion for a subject does not guarantee success. And I agree. Just being fanatic and uber-excited about something is not a shoe-in for startup success. But consider the opposite: if a person is not particularly interested in a subject and not emotionally driven to solve a particular problem in the world, will they be able to make it through the trough of sorrow?
I think not.
Step 3 requires asking yourself if you posses energy, curiosity and passion about what you are doing so you can withstand the inevitable challenges and be able to push through the hardships you will face.
Is it a big and growing market?
Startup fact: Investors are looking for home runs, not singles.
One of the biggest mistakes first time founders make is not evaluating markets correctly and picking a market with low potential for growth. Most investors and potential acquirers evaluate startups on the recipe of future potential. A founder who desires a successful outcome for their company should look for solutions to problems in growing markets.
What is a growing market?
Growing markets are ones with an accelerating rate of competitors, users, revenue potential, and aligned with emerging technologies/platforms. Founders should build their solution with forward thinking perspectives on technology and societal norms. (ie: mobile usage vs desktop usage, network platforms vs non viral sites, portable vs non portable tech, etc…)
Even if a founder is not planning to accept outside investment and wants grow from a bootstrapped position, it still makes sense to look for market that is big and growing.
Step 4 requires one to ask themselves, “no matter the size of my ambition, am I building for tomorrow, not just today?”
What are my unique gifts?
Startups are difficult and require one to utilize their unique talents and gift in ways they may have never imagined before. When a founder starts their company, it’s important they take some time and take into account their naturally gifts. Are you uniquely technical and have the ability to quickly whip together a simple prototype? Or are you more social, amazing with people, a natural salesman and can easily work a room full of investors? Are you a visionary or an operations person?
This is probably the hardest question of the bunch, but the most important because the answer to these questions will point to your next phase of the company – recruiting others. If you are non-technical and (most likely) better with leading people, you will need to find a technical person to balance your founding team out and help you build products. If you are highly technical and can easily hack together websites and mobile apps, you will need to find someone who is less technical but more gifted in the business and people operations.
The last step pulls you inward to understand yourself, what your talents are, and who you should look to bring on and join you in your new venture.
Asking yourself these 5 tough questions should not only help determine if this decision is a good one, but if it is the right one for you at this time.
So Entrepreneurial 