2012. Hard Lessons Learned.

# Written mostly after Thanksgiving. Wrapped up sporadically for whatever reason, on whatever flight, or on whatever couch I seem to find myself on. Today it’s a couch in Denver after a day in the mountains… In a rented Jeep. #

Dwolla is coming up on its 2 year anniversary. There are a million huge milestones for us to celebrate—hundreds of millions in some cases.

I believe the most value I can offer you this week is not giving you a list of everything I want you to know about the last few years and only sharing what is beautifully perfect and what was apparently predictable only to us. I don’t believe there’s value in that.

The last two years, and the two before, weren’t easy. Very few things just happened. There are more than a few times I wondered if the sun would come up, and I’ve had more than one person come up too fast, or didn’t have relevant knowledge and give me really bad advice. I own each decision I made. Polling people for their thoughts has helped me make better decisions.

There are a few things I want to leave with my team and my community. We’re riding a wave, but the wave isn’t big enough yet. We have much work to do and much to learn. So as we enter this next phase, the best thing I can do is be honest about the harder lessons I’ve learned as a founder this year.

The apparent timelines to building companies are more often than not complete fallacies. I think my contribution can be more honest than leading you to believe otherwise. Building a company is lonely and much worse in the beginning. Reading about all the breakthroughs everyone else has (who live somewhere else) doesn’t make it any easier.

So here are some of my harder lessons learned. More than one has come close to costing me everything once or twice over. Some I had to relearn this year.

Most people will not tell you when they are pissed off at you. Value those who do.

Passive aggressive people suck, and they’ll cost you a fortune—metaphorically, emotionally, and literally. Start appreciating the people who tell you what they think from the get go. Learn to question those who are always complimenting you.

Compliments don’t teach you much. Unless you’re Prince William,  Ashton Kutcher, Justin Bieber, Elon Musk, or a very humble Ben Silberman … you’re just not that great, and you have a lot of work to do.

Even then, I’d put every dollar I’ve ever earned in this lifetime  on the fact that every one of those people I mentioned know the difference between ass kissing and necessary feedback. The more successful you become, the more you have to say no and proactively surround yourself with people who contribute to your company’s goals, don’t burn time talking about yesterday or plans they’ll never act on.

Find the doers who tell you the truth. Then find more of them. When you recognize passive aggressive behavior, point it out. If it doesn’t get resolved, end the relationship.

People will make promises. When they don’t keep them, it’s on you.

Advice and promises will come in like a river once you start hitting milestones. Initially, you’ll want to hold those promises and favors until you need them. The easiest way to manage that, in my mind, is never rely on them. Most promises and favors aren’t as genuine as you’d like them to be. Remember, this isn’t personal for the other guy. It’s not their company. It’s yours.

The right people will respond when you need them, but most people won’t. There’s nothing wrong with that. People get busy. Don’t beat yourself up about it.

You’ll be wrong most of the time. Try to make the right decisions all of the time.

As a team member in an early stage company, you’ll astound yourself by the number of times your assumptions are complete garbage. You’ll make the wrong decision only to have to redo it later.

Recognizing mistakes and acting on them are more important than being perfect.

The more times you’re right, the faster the company grows and the better off everyone else is as well. Pretty simple.

Appreciate when you’re right, but don’t think it’s a common theme. Tomorrow you’ll be wrong about something. Assume it was a fluke and push yourself to be right again and again.

Everything really does cost twice as much. no matter how good you are.

All your assumptions are garbage (like your business plan), and recognizing that early will keep you humble. It’s unlikely your spreadsheet is right three years from now.

  • Someone will cost more to bring on.
  • Someone will cost less.
  • You’ll get sued.
  • You’ll end up refiling patents.
  • Healthcare costs will rise.
  • You’ll misunderstand a software license that will cost a fortune.
  • One machine you budgeted for won’t cut fast enough, so you’ll need two and more space.

This will all happen at virtually every moment when you’re awake. You can control product, and a lot of other things, but there’s more you can’t control.

You typically plan for the best scenario in your head. Most of the time it doesn’t go that way.

Life isn’t as linear as a business plan.

be careful who you sell your company to

This was the most brutal lesson for me, because I couldn’t do anything about it once it became obvious things were borked. It has cost me months of sleeping and countless hours wondering what I did wrong.

I spent ages 19 to 25 building my first company.  While most of my friends were in college, I had employees to pay.

When I left the company, I rationalized it this way:

I had grown up and it was time to do something bigger. It was a part of life similar to when you enter school as a college freshman and come out a doctor or lawyer. You’re not the same person on the other side. I figured why couldn’t the same be said for being an entrepreneur?  I went in green and came out a much better person.

It is amazing what you learn.

I put everything into building the parts of that company. Anyone close to me can attest to that. It’s taken me months to realize it’s not mine anymore. There are no next steps for me there. My heart might be in what I built, but the day I signed that contract I had no power to change anything.

Learn to let it go the day you sign it over, or else you’ll be forced to let it go when you least expect.Be thoughtful about how you do it, and even if you think it’s done perfectly, you’ll probably find the new owners do a lot of things you don’t love. That’s life.

Just because someone has more money than you, It doesn’t make them smarter

The earlier you are in the process of founding companies, or having some huge breakout, (measured differently where you’re living) the more harmful this can be. You run the risk of taking advice from people who know absolutely nothing about your business.

I can’t count the number of times a wealthy individual gave me advice that I couldn’t wait to hear and put straight to work. In retrospect, most of it was really bad advice, but there were a few golden nuggets that changed my life.

Truth is, they probably know more than you about something, but you know a lot more about your company. Have the confidence to push on their advice. You’ll be amazed how fast they’ll sit up and dig in. Many times, the advice will change the more context you give, and you walk away better off.

Feedback with no context is a bullet into a dark room full people. I don’t see how it ends well.

middle men are expensive

In many situations there are moments where someone says “I don’t know, but I’ll go find out”. These personalities should be applauded given they actually do what they say. These folks typically don’t make things up, and they get to people with answers. There are two things to be self aware of…

  1. Do they come back with a solution in an acceptable amount of time?
  2. Is the answers always “I don’t know, but I’ll go find out”?

These two things are indicative of much bigger problems. If you cater to it, you’ll end up doing the work yourself. Nip it quickly.

When in doubt. Ship.

Which is what I’m doing with this post after weeks of pondering it’s relevance.

If you’re not shipping, you’re dead.

That’s it. You’ve reached the end of my mini novel. Hopefully one of these results in one or two people having a “ah-ha” moment that saves them some time in 2013!


38 thoughts on “2012. Hard Lessons Learned.”

  1. Felt the gut-wrenching from here… Lived this and the post resonated… And as you probably know despite all these insights gleaned in 2012 there’s no doubt tons more that “ain’t right” that you haven’t seen yet… But maybe you’ll see it sooner this time around.. Bad advice is legion. Flattery is pernicious. Txs for sharing this

  2. Would be even a better read if you could give real examples to all those points. It feels a bit like empty generic advices when you don’t know the specifics.

      1. My life is the context for this entry. You can take the pieces that may be relevant to you and leverage them or ignore them. That’s 100% up to you.

  3. Excuse me good sirs, but what is it this Dwolla you are speaking of? It is a word that is not known to me.

    — Pranab

  4. Ben,

    This post is the best piece of writing I’ve read in a while. Your honesty is brave and powerful. So proud to know you!

    Liz Taub

    1. Ship means go live, deploy! Stop pondering and put your stuff on the market, in the real world!

  5. Perfect timing to find this. year one done and year two pow-wow begins tomorrow. It’s refreshing to hear insights from the mid-coast after a decade on the east. Keep up the good fight!

  6. Ben,

    Nicely articulated. I like that much of the post emphasizes the need to identify, own, and learn from one’s mistakes. And even if advice is great and specific, you’re the one who has the make the decisions and live with them. Following up and keeping promises are highly underrated!

    – John

  7. Hey Ben! I found this via Mr. Parr the other day. I met you back in March 2012 at Startup Weekend. You were supportive and that meant a lot to our team. Thank you, seriously.

  8. Ben, thanks for sharing your thoughts. I don’t how I stumbled upon your blog post, but I am glad I did. At least 4 scenarios or situations apply to me in my company building process as an entrepreneur going into 7th year. And some of my realization and conclusion on what I should be doing in those situations got reaffirmed after reading it.

    Thanks again.

  9. May the path you take during the coming new year be one that takes you farther than ever before.

  10. Sage advice. And if you’re not making enemies, you’re not trying hard enough. Cheers to a great 2013 for you and for Dwolla.

  11. Ben, great insight. I could feel your pain and anguish as I read your post. Your lessons learned center around the loss of time. Money, traction and opportunities can be lost and earned back one step at a time, but time is lost forever. I try to keep that in perspective every single day as I build my own business. Don’t waste time.

  12. Ben this is a powerful and a very genuine post a must read for any entrepreneur. With those lessons learned I’m sure 2013 will be a fantastic year for you! thanks for sharing!

  13. Ben, All true and very crisply stated, based on my work with hundreds of entrepreneurs since 1981

  14. Ben…very well spoken and geniune article. I especially hold close the fact that transparency and honest feedback are absolutely paramount to successfully building a business.

  15. I want to see people write more texts like these! A great article, indeed! I really liked: “PEOPLE WILL MAKE PROMISES. WHEN THEY DON’T KEEP THEM, IT’S ON YOU.”

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