10 Hard Startup Lessons from Year One of Building CMX

It’s been almost one full year since we started CMX.

It feels like it was yesterday, and yet when I look at where we’re at, I can’t believe how much we’ve accomplished in just a year.

This is my third business, and the most successful so far both financially and in terms of clarity of direction. I feel like we’re doing a lot of things right but of course, I’m constantly learning hard lessons about startups and entrepreneurship as I go.

In this post, I want to quickly share some of the bigger personal lessons I’ve learned in 2014:

1. Conferences are a tough business to run and maintain

When we first started, it seemed really simple. Find great speakers, choose a venue, sell tickets and boom…you have yourself a successful conference.

What we’ve learned is that conferences are an incredibly difficult business to get off the ground. They’re unpredictable and there are a ton of factors that you can’t control like other conferences that launch around the same time, unexpected venue costs, speaker cancellations and unpredictable sales rates.

On top of that, the actual event has a thousand details that you have to pay attention to. And if you mess up any one of them, you will hear about it from your attendees.

If you’re going to run a conference:

  1. Hire a great event manager to run the show. We couldn’t survive without Leah
  2. Realize that the conference will probably not pay the bills for the full year unless you get a ton of sponsorship money, host a lot of events every year or are able to charge a lot (more than $1k) for tickets…so you need other forms of revenue throughout the year (which is why we started doing consulting)
  3. Be prepared to dump a significant amount of time into organizing and promoting the event

2. Transparency is powerful, but complicated

We recently sent a letter to our community, honestly sharing how the company is going, the challenges we’re facing and what we’re planning to do to overcome those challenges.

The response was tremendous. We got loads of comments, responses and business leads out of that one letter.

Some companies choose to fake it until they make it. They always want to put out the perception of success and that everything is great. That works for some companies. But for others, transparency will have a much bigger impact and frankly, it feels good to just be honest and not feel like you have to hide things from your community.

That said, transparency isn’t black and white. There are many shades. When writing that simple letter we ran into questions like:

  • How honest should we be?
  • Should I share everything? Just some things?
  • What should the tone be?
  • Should we try to sound strong or vulnerable?
  • Who should we send this letter to? How should we send it?

Ultimately, we will be following in the footsteps of Buffer and always defaulting to transparency because it’s right for the kind of business we’re building.

But as you can see here, transparency can take many forms and you have to figure out what true transparency looks like to your company.

It’s not as easy as just being honest and open. There’s a spectrum of transparency.

3. Create decision filters based on your core values

As a founder, you will face big and small decisions every day.

I’ve struggled with decision making in the past. It’s something I continue to work very hard to improve on. Here’s something that’s worked well for me recently…

By being clear about our company’s core beliefs (write it down if you have to) you can create a filter for making decisions. So every time you’re faced with a decision, you can simple ask “does this align with our values and goals?” If not, don’t do it. If yes, do it. Simple as that.

For example at CMX quality is everything. We hold all of our content to as high level of quality as possible. It’s the #1 factor when choosing speakers, writing content, choosing partners and everything we do.

So whenever I face a decision related to our content, we can look at it through that lens and ask, will doing this result in the highest quality content possible? If not, then we won’t do it.

At events, our goal is both high quality content and creating a powerful interactive experience for attendees. So every time I have to decide if we should spend money on something, I ask “Will this make the quality of our content better? Or will this help our attendees connect with each other in a meaningful way?”  If it’s not a clear yes either way, then we cut it.

4. Decision making isn’t about making the right choice, it’s about making the best choice with the information you have

This is another lesson around decision making and it’s something I learned from one our speakers and my role-models, Scott Belsky. He recently tweeted:

That really stuck with me. Basically, you’ll never have all of the information you need to make a decision, you just have to make a decision with the limited information you have. Over time, with more experience, you have more reference points to guide your decision.

It takes the pressure off of making the perfect choice because there’s no such thing. So you might as well just go with what you know and feel, then see what happens.

5. Some people (me) are good at a lot of things and not great at any one thing 

I’m a good juggler. I’m an extremely fast learner. I can get from novice to pretty good at most skills really quickly. Better than most. As a result, I’m good at a lot of things but not necessarily great at any one hard skill.

I think a lot of founders are this way. I was talking with another CEO friend recently who saw himself in the same way.

It’s why we’re good at getting things off the ground since we can wear a lot of hats and do a good job at everything (but usually not a great job).

This was a good learning for a couple reasons:

  1. It reinforced the importance of building a great team around you of people who are great at specific aspects of the business.
  2. I sometimes see other people who are really good at something and my first thought is “wow I really need to get better at that”. The truth is I don’t because ultimately I’m not the person who needs to be great at that skill.

Weight lifted.

6. It’s better to say exactly what’s on your mind, right away

One of my biggest flaws is I often care too much about what other people think.

As a result, I often don’t say what’s on my mind. Or I’ll beat around the bush without really saying it. I get worried that I might offend the person or they won’t like me.

As a result, I end up avoiding small important issues until they become big important issues and they’re a lot more difficult to handle.

I recently started doing what one of my old bosses, Loic LeMeur used to do when I was running community at LeWeb. If there was something bothering him, even if it was confrontational, he’d immediately send me an email with 1-2 sentences expressing his thoughts.

He told me that he’d rather just say what was on his mind than keep it to himself because it forced us to talk about it and move passed it. As a result it was one of the best working relationships I’ve ever had. There was no bullshit.

Say what’s on your mind. Be as blunt as possible. If there’s any awkwardness, it passes quickly and ultimately, everyone’s better off.

 7. Building a business is much easier when you stick to what you know

Community building is my thing. It’s what I think about all the time and I’ve done and written about enough in the space that all my professional friends have been calling me “the community guy” for as long as I can remember.

My last company, Feast, was a food/cooking business. I had no background in food or cooking, I wasn’t even a good cook. We just had a good idea around a pain-point that we ourselves felt. But with no deep understanding of the space, no real connections in the food space and a lack of true passion for food, it proved to be an extremely difficult business for us to build.

CMX has been the opposite. I understand the space on a deeper level than most and can talk about this stuff all day. As a result, things just move more naturally.

It’s a huge difference, like swimming upstream vs downstream.

If life is pushing you in a specific direction, going with the flow will come make life much easier, as long as you like the direction.

As a founder, look for opportunities to build something in the area that you truly care most about. A lot of things can click into place if you do.

8. There is no ultimate state of happiness or success

I’ve written about this before, but it’s a lesson that I’m constantly reminded of and wanted to reiterate here.

When anyone tells you how to become a successful or happy person, ignore it. There’s no such thing as a happy person or a successful person. There is no point in life where all of a sudden you will be permanently successful or happy.

Life is an ebb and flow of happiness, sadness, success, failure, high energy, low energy etc. You can be any one of those things at any given time, regardless of your overall situation.

When you realize that, you can stop trying to reach this ultimate mythical state of happiness and you can focus on the present. Are you happy in this moment? Are you successful in this moment? Where do you want to be right now and how can you get there?

9. Ignore people who tell you how to win the lottery

I absolutely loved this talk by Darius Kazemi at XOXO. It was a comical take on what we hear from so many speakers when they get on stage and tell their story of how they succeeded.

Darius sums it up with this line that really stuck with me:

“There’s two kinds of creative advice. There’s ‘How to buy more lottery tickets’ and there’s ‘How to win the lottery’. I think the former can be really useful and the latter is nonsense.”

What he’s saying is that “experts” will often tell you “here’s how to achieve X goal”. We see those kinds of articles and talks all the time. “How to get 10000 emails” “How to make $10Mil” “They key to building a successful startup”

That advice won’t help you. It’s nonsense.

So many factors will go into whether or not something works at any given time that it’s impossible for someone to tell you what will work. The element of luck is too large. They’re basically telling you, “Here’s how to win the lottery”.

So ignore that kind of advice and instead focus on the advice that helps you buy more lottery tickets. Focus on the advice that teaches you the process for taking shots, experimenting and learning.

Don’t try to learn from someone’s results.

Instead, learn from their process for experimenting with different approaches that ultimately led them to find an approach that worked.

10. Money is important

Anyone who tells you that money isn’t important has never been broke and has never bootstrapped a business.

I had a shift in mentality recently around money. I realized for my entire career as an entrepreneur I chose not to take on opportunities to make money if it took time away from building my companies.

I’d make financial sacrifices in the short run in the hopes that a company would take off and pay off in the long run.

Then I’d justify being broke by thinking, “the pressure of being broke will make me work harder to succeed.”

That was dumb. You need money.

You need it to eat. You need it to pay other people to work with you. You need it to fly to see your family. You need it to keep clean clothes from The Fifth Collection on your back.

I will always work hard to build successful businesses with long term value that makes the world a better place. But if I have opportunities to make money in the short run, I will strongly consider taking them. Money will enable me to do more, to build more and I won’t be distracted by constantly not having it.

Business shouldn’t be all about money. But it should be a little bit about money.

Stop Asking “Am I Happy?”, That’s Not How it Works


I’ve always had this vague idea in my head that happiness is this point in life that I can reach.

If I work hard enough, make lots of friends, make money, travel, check off all the boxes…then I’ll be a “happy person”.

Other people seem to think the same way because I’ve been asked many times “Are you happy?”. I always struggle to answer them. Happiness just doesn’t seem to work that way. I start thinking…

  1. It’s not that black and white. There’s a spectrum of happiness
  2. What is happiness? Is it excitement? Is it being motivated? Is it laughing? Is it finding meaning?
  3. In this moment, I can be happy about some things and unhappy about others. I can be happy with my life in general, but unhappy about the gum I stepped on that day.

What I realized is that I don’t think happiness, however you define it, is a point in life that you can reach. There’s no one in life who’s achieved level 5 happiness and now they’re just happy all the time. Even the ones who seem to have it all, or always seem positive…they aren’t always happy.

Actually, if I was happy all the time that might not be so great. The moments of sadness in life are tough, but they make the moments of happiness that much better. There’s a spectrum of human emotion and happiness isn’t the only one that’s okay to have. You’re not broken if you’re not happy.

Whenever I feel stressed, angry or sad I try to accept it. They’re normal human emotions. Life is a crazy adventure and your emotions will ebb and flow with it.

So instead of thinking about how much I hate being stressed, I think about why I’m stressed and realize that given the situation this is a perfectly normal reaction.

And instead of asking myself, “Am I happy?” I try to ask myself things like…

  • Why am I doing what I’m doing?
  • Am I proud of what I’m doing?
  • Who do I want to be and am I working toward that goal?

Happiness isn’t a phase in life you can reach. Happiness is in the moment. And when it’s not there, that doesn’t mean you’re doing it wrong. It just means you’re human.

Thanks to Mike Hrostoski for inspiring the post.

Photo cred: Angelo González

Just Hit Publish

I’ve struggled to keep up with my writing lately.

I started writing a post every day for over 100 days. I accomplished that goal and things were humming along.

Then all of a sudden, I started to falter.

What happens when you write that much is a lot of awesome stuff:

– I started being asked to contribute to other publications

– I had a few post really explode, driving a lot of traffic to the blog

– I actually built a following of people who read most of my posts

Now all of these are really good outcomes, but the problem is when I started writing, I was just doing it for myself to get my thoughts out. I could whip up a post quickly and just get those ideas out there. Now after these outcomes, I’ve felt a large amount of pressure to write really epic posts every time.

Posts like this where I can just write and hit publish have become much harder for me to publish. They’re not good enough because they may not reach the heights of some of my other posts.

I feel like my posts have to be thorough, compelling and super high quality in order to publish. But that feeling is wrong unless you’re writing for another publication or you’re writing for a living.

Here on this blog, I can write whatever is on my mind and hit publish without feeling like I have to make it perfect. If people like the post, great. If they don’t, I still get value out of getting the words flowing.

Sometimes, you just have to hit publish. It’s more important that you keep the flow of ideas going than to make sure every idea is perfect.

That probably applies to other parts of business too. Everything doesn’t have to be perfect or epic. It just have to be something, anything to keep things moving forward.

Plus, you should keep in mind that you have no idea which topics will hit a nerve and explode, and what will fall flat. I’ve had posts that took me 5 minutes to write reach tens of thousands of people. I’ve also worked on posts for hours just to have 50 people read it.

You never know, so just hit publish.


Learned from Failure – Why You Should Never Send Negative Emails

I’ve learned a lot about what makes for good communication in business.

I’ve also learned about what makes for really poor communication that results in anger, drama and failure.

There’s one philosophy that has consistently proven true for me, in multiple jobs, over multiple years with many different kinds of people.

Negative emails make for very poor communication and should always be discussed in person (or at least on the phone) instead.

I’ve learned by making the mistake several times (I still do today). And I’ve learned from other people making the same mistake with me.

Every time I’ve sent an emotional email, I’ve regretted it. Every time someone sends me an emotional email, I get stressed.

It’s not because they’re emotional. I think it’s absolutely essential that when you work closely with people, that everyone feels comfortable sharing their feelings, both good and bad. I have just found that email is the wrong place for it when it’s bad.

If you’re sending negative feedback, that might be okay as long as it’s presented in the positive light of your mutual goal to be better and improve. But as soon as emotion comes into it, take it off email.

This post is based on my own personal experiences so maybe others would respond differently. But in case you’re like me, I figured it’s worth sharing.

Here’s why negative emotional emails are bad news bears…

1. Lack of tone, body language and eye contact

Are they being sarcastic? Angry? Sad? I have no idea.

What often happens is I’ll end up assuming the worse. I assume they’re livid, full of anger and disgust.

It doesn’t matter how descriptive you are or how many emoticons you use, when you write something emotional, how the other person perceives that emotion is completely out of your control.

2. It can create a battle to win out

Written debates are brutal. You can pick apart every single word and phrase of the opponent and you read over your response 17 times before sending it over.

That’s not a conversation, that’s a battle to win out. You’re just trying to shoot down all angles of the other person’s argument rather than come to an understanding and move forward.

I can’t speak for others but when I used to receive emotional emails, I’d overanalyze that thing until I turn blue. Then I’d overanalyze my response, trying to cover every angle.

As a result, everyone loses, the problem never gets settled and it can cause bad juju amongst teammates.

3. Ready, Set, DWELL!

Emails also leave a lot of space between messages. Unlike a conversation where you keep working through the issue together live in real time, an email just sits there, festering.

When I receive emotional emails, I dwell. For days or until I finally talk to the person, I obsess over the email, what it means, how the other person is feeling and how I’ll deal with it. It’s depressing, really.

Passive communication like that is great for coordination and general information exchange. But when you start bringing human emotions into the mix, save it until you can actually have a live conversation about it.

4. We can be irrational in the moment

Most emotional emails are written in the moment of emotion.

Our emotions are strong and can make us say or do things we regret. Forcing yourself to take it offline and talk it out in person will also give you time to reflect and approach the situation rationally.

At the very least, save it as a draft and come back to it later after you’ve had time to calm down, reflect and think rationally.

So here’s what you can do instead of sending emotional emails:

1. Just take it offline

When I want to send one, I’ll write out the draft and then not send it. Then I’ll send something like, “hey, can we hop on a call, had something on my mind” and set up a time to talk through it.

When someone sends me a negative email now, I simply respond with something along the lines of “let’s get on skype and talk this out”.

That simple change in how I deal with communication has vastly improved both my sanity and my ability to work well with others.

2. Set up a regular time to share emotions

Another good strategy that has worked for Nadia and I is to set a specific meeting up at the same time every week that’s dedicated to sharing your thoughts, feelings, fears, excitements etc. We’d go for a walk, go get bubble tea, sit in a park, away from computers, and just talk. This way, if we had something weighing on our mind, we knew we’d have the chance to share it at the meeting and didn’t have to email to bring it up.

Turns out when you have conversations like that, you gain a lot of perspective about yourself and your company as well. Some of our biggest decisions for Feast have come from these talks.

3. Write it out but don’t send it

A friend of mine does this every time he feels angry. He’ll write out the email but never send it. Writing it out makes him feel better and lets him think through the situation. Then he just deletes the draft.

I’ve done the same, sometimes actually writing letters to people in my private journal. Just writing things out can make you feel much better.

If you have no other option than to email, then do that. It’s better than not expressing your feelings at all. But if you can, hold it until you can talk it out live in real time.

Photo Credit: Anita Robicheau via Compfight cc

How to Make Other People Feel Good About Themselves

piggybackrideWant to make friends and build a strong network?

Want to be the person that people want to spend time with?

Want to earn someone’s trust and respect?

Want to be that manager that everyone loves and enjoys working with?

There are a few people I’ve met in my life that I have a deep respect for, more so than anyone else I’ve met. They’ve proven their ability to do all of those things above time and time again. Everyone loves them, they’re incredibly successful and they just seem to live a good life.

Some time ago I noticed there’s something very consistent about what makes them all so successful and well thought of.

They make other people feel really good about themselves.

Every chance they get, whether with friends, strangers, in public, in private, whatever…they make you feel awesome.

There are a number of ways that I’ve seen them work their magic. Some are simple and very obvious. Others take a little more work and aren’t so obvious.

1. Compliment people even if it feels awkward

The simplest most obvious thing you can do it compliment them.

Complimenting can feel awkward and take some willpower sometimes. I catch myself wanting to compliment people but then feeling embarrassed and just keeping it to myself.

I learned from watching these people who are really good at complimenting how effective it can be.

If you like someone’s shoes, you think they’re funny, you respect them…anything good, tell them! By keeping it to yourself you’re missing an opportunity to make someone else feel really good about themselves. That in turn will make you feel good for making them feel good. And your relationship will strengthen.

Take Action: Think about someone you know and care for. What’s one thing you like about them? Have you ever told them that? What’s stopping you from texting it to them right now or telling it to them next time you see them?

2. Make other people successful

This one is harder but more powerful.

I haven’t been so great at this in my career. I remember the first time I was put in a managerial position, this concept didn’t even cross my mind. Instead of focusing on making others successful, I thought they were there to make me and the company successful.

It was a shallow understanding and one that resulted in a brilliant failure, but a memorable lesson.

I’ve tried to adjust my thinking to a new idea: I work for everyone else in my life. My job, is to make them successful. If I can do that, we all win.

Take Action: Look at your todo list for the next week. Look at each item and think about who it’s helping. Is it making someone else successful or just you? Are there other things you can add in there that will make someone else successful?

3. Shine the spotlight on other people

Make sure credit is given where it’s due every chance you get. This is another thing I haven’t been so great at in the past. Turns out I’m decent at finding spotlights and I haven’t always thought about pointing it at the people around me.

There’s a difference between internal and external recognition as well. Just because you’re very grateful and tell the person that all the time, that won’t have the same effect as recognition in the public eye. If you can give them both, that’s ideal.

Take action: Look at your twitter feed. When was the last time you bragged about someone else? When was the last time you put the spotlight on someone else? Who can you tweet about right now to put the spotlight on them?

If you focus on those three things, you’ll make people feel good about themselves. When they win, you win.


Photo Credit: Fujoshi via Compfight cc