Founder Friday is a weekly guest post written by a founder who is based in or hails from the Silicon Prairie. Each month, a topic relevant to startups is presented and founders share lessons learned or best practices utilized on that topic. July’s topic is about scaling your startup.
About the author: Ben Milne is the founder and CEO of Dwolla, a payments startup based in Des Moines. This post originally appeared on Milne’s personal blog and has been posted here with his permission.
2013 was one of the hardest years of my life. It wasn’t the hardest but it was challenging. The hardest, was one year as a kid when my dad got Parkinson’s, my mom got sick, my mom’s best friend died and the grandparent who helped raise me withered away like ash with cancer right in front of my eyes.
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That’s a different kind of hard. This year was not hard in that way. I’ve been humbled more times than years I’ll live and I’ve been fortunate just as many times. This image of Forrest Gump seems to incapsulate my life countless times this year.
I meet someone I don’t know. They’re telling me nice things and I’m confused about what I’m doing there and I just have to pee. I realize I drank too much water and then look over and realize that’s a Clinton at the other table and everyone seems to have a story that starts with MIT, Harvard, or Stanford. This is life in 2013. It was a weird one.
2013 ironically, was also one of the happiest years of my life. Life is challenging but this year has also taught me the value in continuing to find opportunity in good people, great ideas, and simply doing the stuff that you said that you’d do.
There’s a lot of people in the world with real problems and running a venture funded startup isn’t a real problem… It’s a privilege… That doesn’t mean it isn’t mentally, socially, emotionally and economically hard as hell. Running a venture funded startup with high stakes is a bipolar roller-coaster with hundreds of millions of dollars in the balance before you have any of it. It’s kind of awesome but it makes very little rational sense in the context of what I believed normal life to be as a kid.
In the last year I found myself in a different city and I’m trying to wrap my head around the shift between $1M and $1B in responsibilities over the last 10 years. I’ve made peace with the fact that I may never fully adjust and I’ve seen more people come and go in my life this year than I’ve ever known possible.
I’ve also been humbled in ways I didn’t know possible. Some of my idols started giving me time and advice… Some of my enemies set me free and even showed me love when they didn’t need to (I liken this to that Here Comes The Boom movie when the real fighter gives the big dude a hug at the end).
This is the life of building a company and it’s one that I’m not the first to take on… I know that. I try to do better every day and there is no shortage of things to do better. Life can, at times, be a futile effort in trying less to be perfect and more to simply be better.
At times, I reflect wondering what I did wrong but mostly I’m excited about the future. So this year, while I had plenty of times to feel like I’m a moron, I feel great and I’m excited. I also want to keep with tradition.
So here it is. 2013. Hard Lessons learned.
Get a great lawyer and get annoying about the contracts
The second your word is questionable it’s worth very little. With lawyers and most of the world, if it’s not in writing… It’s worth nothing.
I touch on the importance of lawyers while speaking every once in a while and most of the time it comes up in the context of finding the right help when starting a company. My primary gripe about my lack of legal attention has been when selling one. When I sold my first company I took people at face value time and time again. At a time when I was incredibly excited to move on and build something else great, I should have been harder on people. A few years later basically everyone who I took at face value has owned me or put me in a really weird spot.
If I had it to do over again I would have spent significantly more time and money on protecting myself through the sale of that company.
My advice would be that after you get a great lawyer you should get another one. Keep in mind you don’t replace the first lawyer… You build a team around them and they’ll all teach you valuable things.
If you’re afraid… You’ve lost. If you’re cynical… You’ve lost.
I have no idea where it came from but I heard this repeated somewhere. Something along the lines of: “When you’re afraid you lose the confidence to walk through walls.”
When I heard it, it was made to sound like Mark Zuckerburg said it but when I Google it his name doesn’t show up so we’ll just give him credit regardless.
Whether or not Mark said it or not doesn’t matter. What matters is that the moment your view of things changes so it is full of fear, you can’t act. The moment your view is too cynical to see what’s good, you’re nothing but a paperweight that processes food and drink to simply deposit it in holes along life’s depressing way.
Some people are just born cynical. They’re rocking Eeyore’s tone wherever they are in life and hearing them laugh is virtually impossible unless it’s at someone else’s expense. While in social situations you sometimes see this attitude held as the one worth following, where arguments are won by who can be loudest like a trailer park fist fight over whose dog shit in whose yard… The unfortunate who are stuck in this circle of behavior have already lost. In all ways. Just stay out of it.
If you find yourself sounding a bit like Eeyore and being afraid to ship, it’s not time to convince other people of why you’re right. It’s time to work with them to make things better and if you refuse to… It’s time to leave.
Don’t be Eeyore. Be awesome.
Learn to laugh at yourself
Let me tell you a short story. I’m not the world’s greatest speaker but I’m decent and I’m getting better. You can put me in front of 1,000 people and I’ll black out and most of what I say I don’t remember. It typically makes more sense than not though and most of the time I can’t help but laugh as soon it’s over and I’m comfortable.
However. When I order a sub at Subway, I freak out. I black out just the same and get so nervous I’m going to hold up the people behind me I always instantly order the same thing like some sort of savant recall (where being a savant is defined by my ability to order the same thing at subway every time because I’m panicking about holding up the line): A 6-inch seafood sub, on white, with provolone cheese. If I plan ahead I might be able to order it with flat bread without stuttering.
It’s not that the seafood sub is really that great and it’s not that I’m so socially awkward I should be nervous about ordering at Subway but when I get to that counter my mind goes blank. That’s why I’m the guy standing in the back of subway looking at the menu for 10 minutes before I get in line. I’m planning ahead.
I think that is hilarious and there is no part of me that thinks that’s a normal thing for an adult. At this point I should be able to order whatever I want at Subway like a pro but it’s just not my strong suit. Whatever, it’s funny.
You will never stop getting sued if you’re taking big swings
That’s just how it is. I’m constantly surprised by how it happens but it will not stop. You should just expect it. I’m not saying that you should try to make it happen to get it out of the way because if you do that you’ll just make it happen way more than it should… But frankly it’s just going to happen because you won’t always agree with people and you won’t have much of a startup if you agree with everyone.
Getting sued doesn’t necessarily mean you’re doing something wrong it just means that you’ve got the attention of some people you’d prefer not to have the attention of. Sometimes it works out in your favor and sometimes it doesn’t. Welcome to the real world. You can’t control everything. It’s also the same world where you end up suing some of your friends even though you don’t want to and that sucks and it shouldn’t happen.
The first time it happens it’s a little uncomfortable. The ninth time… Well. It still sucks but it’s not as bad.
Respect others, especially when you don’t understand
I can’t imagine there is a single person who will read this that has not had a moment in their life that left them speechless. News or a discovery in a park that just left nothing in your brain but astonishment.
Sometimes those moments are psychotic and the effects if you don’t act are catastrophic but typically it’s just when people do really weird shit you can’t rationalize. One day, when I’m old and I’m not responsible for anyone but my wife, my dogs and keeping my lawn mowed, I’ll tell those stories.
Most people are really good. That is to say that the large majority of people are really fucking fantastic when you get down to the core of what makes them tick and even if you don’t agree with someone, there’s virtually nothing to be gained from disrespecting someone because you simply don’t agree.
Don’t be a troll. Be the human that opens the door once in a while, even for people you don’t know. It’s far more impressive to be kind when you don’t have to be than it is to be terrible when the opportunity presents itself. If you’re just running around being an anonymous jerk to people… Well then… You’re a troll.
The value in the world isn’t created by trolls. It just gets trolled.
Make people show you. Especially the bank.
If I got hit by a car this year and my tombstone said “Should have gotten it in writing more often” then my tombstone would get a smile from my hovering soul.
I told one attorney this year that I felt like I needed to start wearing an attorney on my back everywhere I went. He laughed. Probably because he billed me for his time to listen to the bad joke.
In the back of my head I was envisioning something like I’m Master Blaster and I’ve got this killer attorney on my back keeping me in the clear making sure everything is in writing, all the time. Then I realized I’m not ginormous, don’t wear a metal helmet and my imagination had gotten away with me.
Look though… Regardless of my Master Blaster reference, the fact that we’re not in Barter Town, and the tangental departure in my train of thought, my statement remains the same. Don’t take people’s word for it… Ask them to show you. You’ll be surprised at how often people will show you really amazing things and every once in a while you’ll find out those really beautiful words were kind of empty. Especially in the contract that was supposed to change your life.
The reason I call out the bank is for the following reasons. Banks are built on paperwork and if it’s not in writing it didn’t happen regardless of whether it’s good or bad. They’re built on systems that reinforce the strength of paperwork even if you don’t know it exists and their protected by systems on top of the paperwork to protect the interests of the paperwork, not you.
There are good bankers and there are bad bankers. Most are good but every once in a while you find a bad one and you can protect yourself from doing one simple thing. Don’t take their word for anything, make them show you everything.
Speak with your feet
I hate to make this as simple as saying you can’t be everywhere at once but it’s just so hard to argue with. Wherever you physically put yourself is where others will perceive to be the most important location for you to be.
We know that’s not always true but every “they wanted to be here, but…” is following by someone else thinking “well they’re not here so what you just said doesn’t matter at all…”
This one isn’t complicated. Maybe just a heads up. Wherever you physically put yourself is where those around will perceive is what is most important to you. If there is any possibility where you are will be misunderstood, try to be crystal clear and transparent all the time about where/why/when you’ll be somewhere.
You’ll communicate poorly but try not to
Even if you say something a thousand times, it’s going to be heard differently by a lot of different groups. Don’t get mad at others for what they don’t understand. Take it upon yourself to get clearer about what you’re trying to say.
It’s no one else’s job to figure out what you’re trying to say. It’s your job to be an effective communicator even on complex subjects. Respect the audience.
When you know, you know. When you don’t, admit it.
This might as well say trust your gut. You’ll be wrong a lot but if your gut doesn’t completely suck you’ll be right more than you’re wrong and that’s a good average.
One of my favorite questions in this life is and will likely forever be “what does ______ mean.” You see, I don’t know what every word means and I constantly ask people what something means if they use a word I don’t understand. That or I file it for later.
Someone not too long ago informed me that I had a “rather nihilistic” view of identity on the internet. I had to look up nihilist to understand his context. So what.
Charise Flynn, Dwolla’s COO, has a glorious propensity to awkwardly laugh and say “I have no idea what that means” from time to time and it’s amazingly effective. Sometimes people get caught using words they don’t actually understand the meaning of and other times (and more often) they have a smile on their face and share some wisdom.
Trust. Win. Trust. Win. Trust. Lose really huge. Trust again.
No great relationship or product is built without trust. Without trust, I don’t understand how you can build something great.
Early on in relationships I’ve continually found it healthy to intentionally select to trust someone or not based on my experiences with them. When I don’t trust them I cut the relationship promptly, but when I do, I invest heavily in them and try to help in whatever way I can.
No matter how many times you have someone stab you in the back or say something you can’t believe, the only time they’ll ever win is when you choose not to try trust anybody at all. Brush it off and let it be what it is.
It’s normal from someone to walk away from a problem they created
This is one that has helped me see the value I otherwise may have missed in a lot of people only because I started to see who sticks around with the shovel to clean up the mess and take another swing every time which is what you continue to do in a startup every time something happens that doesn’t shoot you into the stratosphere.
It’s also the same thing you do in life until you’re swimming in the perfect existence you see in your head. Better lives and companies take work and time and both are full of a gaggle of failures.
Some personalities do this:
- Insult people for not fixing the problem months after they could have helped.
- Over-promise on everything and don’t show up when it’s time to make it right.
- Convince themselves it’s anyone’s fault but their own. They get defensive that “it just sucks” or “never should have been done that way” or my favorite “I can’t do anything with this.”
- Completely shut down and just stop contributing in a helpful way.
Step 1 – Give them the benefit of the doubt and work to motivate and inspire them.
Step 2 – If that doesn’t work and it’s obvious they could care less, the time you put in is a net(-) and will always be that way.
Some people do this when a problem pops up:
- They rally.
- They ask what can go better and how they can help.
- They poll for solutions, they clean up, and they swing again.
You need a lot of people in your life who are in the second camp on this one. Without it, you’ll die and quite frankly you’ll never be able to realize the value unless you understand this… The people who keep showing up, who rally, who ask questions, and keep swinging are the rare ones. Not the complaints, the giving up, or all that other crap.
Most people will be happy to let other people clean up and that’s ok but when you find those other people that keep showing up even when it’s really hard, cherish them. If you can find enough people like that you’ll find yourself in a very non-traditional environment that eats problems and jumps at opportunities.
I’m damn lucky. I work with a lot of people in Camp 2. We have one of the most unique technologies in the world and we’ve been swinging for the fences for 3 years and tomorrow we’ll swing again. I’m one fortunate man.
The easy road is a fallacy for most of us.
If you swing and you’re from the Midwest, most people will never stop thinking you’re a little weird
It’s just that way. Success is never guaranteed and most folks will understand the decent more than they will the ascent. The reason for that being, the general population probably knows more people who are battling cancer than people who have built meaningful companies. It’s just not a common thing around here and it’s hard for a lot of people to wrap their head around. There’s nothing wrong with them at all, they just don’t know.
If you’re anything like me, which you probably are if you’re still reading this, you probably have this borderline unhealthy itch to create something. I don’t know what it is for you but for me it’s typically solutions to things that really piss me off.
Each stage of growth and every opportunity comes with a few basic and predictable trends. At first, you’ve got nothing to risk because you’ve actually got nothing. Then, you’ve got more to protect including other people, so you don’t want to be too risky. Then, you’ve got this weird risk of complacency just sustaining what you’ve built.
You’ve got to keep swinging and with each swing you’ll find a few more people that wish you would stop. Keep in mind… If you’re a founder, it’s your job not to stop swinging until the thing you’re building is what it’s supposed to be. You’ll probably fail along the way but your distinct ability to keep going makes it much more plausible you’ll be successful in the pursuit.
Ask more questions than seem appropriate
Our generation has a gift that no other living generation in humankind has ever had. An index of the world’s knowledge at the tips of our fingers accessed through a resource which is now commoditized to the point that accessing the internet is probably easier than owning a copy of Hamlet for some people.
That means, whatever separation of economic and social knowledge which happened throughout humankind due to status or access has been almost completely eradicated. Our generation has the ability to learn almost anything we want on any subject, almost instantly.
There is an exception to this and an inherent danger. We’ve become so accustomed to knowing things because we can Google anything we want that we stop asking people questions face to face and attempt to research them later. There’s a lot of knowledge about why things are the way they are in the moment that you can’t find on Google.
For example, I can probably find a rather accurate series of events about Mike Tyson’s fall from grace but I can’t find what series events actually happened in back rooms to stop SOPA.
The world’s direction can happen due to massive pressures of opinion but more often than not it happens based on information that you can’t google and the context it’s delivered in. If you truly believe your project can change the world, it’s necessary to start asking more questions about things that you can’t Google.
Your enemy is probably your best teacher
The most brutal moments of the last year for me personally were when someone I absolutely couldn’t stand made a good point, and I was wrong. Those moments where someone points something out and you know they’re completely right, regardless of how much being in their presence makes you want to vomit.
One of my greatest strengths is that I truly believe I can admit when I’m wrong and hearing me apologize for something is probably something people close to me are used to. I learn new things all the time and I’m constantly baffled by how foolish I was a week, a month, a year, 3 years, 10 years ago.
Sometimes corrections come from people you don’t like. It’s not constructive criticism and many times it’s someone or something that wants to simply cut you down because it perceives you to be a threat to something, anything, or just generally to a status quo.
Take your beatings and while the dude who just kicked your ass is busy celebrating… put what you learned to work. Even Muhammad Ali took a punch once in a while but thankfully for the rest of us, our life isn’t measured by 3 minute spurts of glory. It’s measured by what we create over the span of our entire life.
As a good friend once told me:
“It’s a marathon, not a sprint.” – Christian
Most of us learn the hard way… And that’s ok.
Now get back to work and create something.
