This is post #2 in my 365 Writing Challenge.

If you’re a founder, leadership is probably a topic that runs through your head every single day.

The success of your company is directly related to your ability to lead. We’ve seen companies live and die by their leadership. We’ve also seen all different kinds of leaders…good, evil, outgoing, soft-spoken etc.

So it begs the question, what makes a great business leader?

There are a lot of models, books and theories around leadership. Today I’m going to refer to this recent post from Mark Suster that really inspired me, Some Thoughts on Leadership Going into 2016.

Like the title states, this isn’t a research backed leadership model, they’re just based on Mark’s opinion based on his experience. Mark is a seasoned entrepreneur who has sold two companies and is now a well respected investor who has seen a lot of CEO’s go through the trials of building a startup. So I trust his perspective when it comes to identifying leadership.

In his post, he lays out 7 elements of a great leader:

  1. Sense of Purpose
  2. Conviction
  3. Relationships
  4. Team Building
  5. Communications
  6. Empowerment
  7. Presence

In this article I will:

  1. Do a really quick review of each one with a quote from Mark’s post and my quick interpretation
  2. Share how I’m making this model actionable

Let’s start with the quick reviews…

1. Sense of Purpose

“If people don’t know the mission there is no way to achieve the objective and you end up with a team pulling in 100 different directions – even if only by small amounts.”

This is the “why” behind why you’re building your company. It’s your vision, mission and values. It’s your culture.

Your purpose is your north star that acts as a lens through which you make decisions, and the guide rails that keep your team aligned and on track.  Most experts, Mark included, would recommend you codify your sense of purpose. Write it down, make it specific, and revisit it regularly.

2. Conviction

“Great leaders have deeply held conviction in their strategy and plans. Codifying what you believe is one thing but sticking to your plans is another.”

This is your ability to stick to your sense of purpose and your plan.

If you think of any great leader, you can see their conviction very clearly. They have their set of principles and they stick to them. That’s why people respect them, even if they don’t agree with them. It’s their conviction that allows them to make hard decisions.

3. Relationships

“People will accept being overruled or will accept compromises or will live through cut-backs and downsizing or whatever else is thrown their way when they trust and respect you. And this comes from hours and hours of investing in personal relationships.”

If you’re a people pleaser like me, you want everyone to like you. That’s not what Mark’s talking about here. In order to make everyone like you, you have to make everyone happy and that isn’t always possible. Leaders are faced with incredibly difficult situations every day. What’s important is that people respect you so that when you do have to make a hard decision, they trust that you’re making the right choice even if it doesn’t positively affect them. Respect is built on trust. Trust is built by putting in the time with people and really understanding their needs.

4. Team Building

“The hardest thing as a leader of teams is to know when it is time to “hire above” your existing team and when it’s time to let your team members try to develop into the next role.”

Great leaders surround themselves with great people. They know they can’t do it all alone and they’re aware of their own weaknesses. Building the right team is critical to building a successful business.

Mark describes one of the hardest decisions when building a team is whether to hire above your existing team, or give existing members an opportunity to grow into the role.

5. Communication

Great leaders tell people what they’re doing and why. They are transparent about the goals and objectives of the organization and they’re willing to tell people how the company is doing against those goals.

Communication is at the core of any healthy relationships, business or community. “Communicate early and often” is the rule of thumb you’ll hear in the startup world. This can be a tough one for a lot of leaders because they want to take the weight of the challenges on their own shoulders. It’s hard to communicate bad news. Communication also isn’t one of those things you can do reactively. It has to be a habit, building communication systems into your business routine. People can’t help you if they don’t know what the problem is, and you’re not doing your team any favors by not telling them the good and the bad.

6. Empowerment

You may have a strong sense of purpose, a great and differentiated product or service and a great team surrounding you but if you don’t learn to empower your team you’ll never be as effective of a leader as you should be. Empowerment is exactly what leadership is: It’s about setting the direction for the team, assembling talented players and then letting them execute to their fullest abilities.

Founders are used to controlling everything. So when it comes time to build a team around you, it can be hard to give up that control. In some ways I struggle with this too. Pretty soon I’m going to have to give up owning the core offering of our business (our conference) so I’ll be put to the test again. Empowerment isn’t just about giving people ownership over a specific area of the business though. It’s also about creating an environment where people feel like they have a voice, that they play an important role in the organization and that they have a level of autonomy.

7. Presence

“…great leaders are present. They show up in the office. They respond to email. They get involved in laborious staff meetings. They get involved in hard product decisions. They give good news and bad news personally. They know when morale is down because they are living it. They lead from the front…”

This isn’t a hard one for those of us who are bootstrapped or working with extremely limited resources. But eventually, once you build a team, it may be tempting to take your hands out of the day to day operations. There are a lot of entrepreneurs who like to travel and take extended periods of time off. That’s fine if you need that to be happy (to some extent I do too) but it won’t help your leadership. A leader is putting in the time as much or more than any other member of the team.

Making the Model Actionable

I was really inspired by these 7 elements as I felt they aligned well with my own beliefs around leadership. I often think of leadership as this one singular thing, but seeing it broken down like this made it easier to wrap my head around.

If these are the 7 elements that determine the strength of a leader, I started wondering how good I was at each one. So I rated myself. For each of the 7 elements, I gave myself a rating of 1-5. Here’s what I came up with:

Sense of Purpose: 3
Conviction: 2
Relationships: 2
Team Building: 4
Communications: 3
Empowerment: 4
Presence: 4

Average: 3.1 out of 5

Not great eh? I know I’m my own harshest critic but it definitely looks like I have a lot of room for improvement. So I also wrote down what I’m currently doing well and how I could improve in each area:

1. Sense of Purpose (3):

We have a very clear vision and mission at CMX and we’re really good at sharing and applying it regularly. This has come naturally to me because it’s something that’s so deeply rooted in our culture and purpose. Where we need to improve is in the specification and application of our values. We’ve had values but they’ve felt more like vague platitudes than something we really live by. It’s up to me as a leader to get very clear about what our true values are, write them down and make them actionable. I’ve done the first two parts…making them actionable is still something we have to figure out.

2. Conviction (2):

This is one of the areas where I need the most improvement. It’s not because I have trouble committing to my beliefs or plans, it’s because I struggle with planning. You can’t commit to a plan that you don’t have. So the first step is to get a clear plan down, based on the vision I have for the company, and then work with my team and advisors to refine that plan. Once we have something specific, it becomes much easier to commit to it, and practice conviction.

3. Relationships (2):

This is the second area where I need the most improvement. If you know me, you might be surprised by this. Most would say that relationship building is one of my best skills. In many ways it is, I’m really good at putting time in with people, I’m highly empathetic and I’m good at making friends. But as Mark says, relationships isn’t just about getting people to like you, it’s about respect. It’s about making the hard decisions when you need to. My nature and need for people to like me gets in the way of this regularly. I end up becoming friends with people rather than someone they respect as a leader. This is an area I strongly need to improve.

4. Team Building (4):

Right now our team is small but strong. Everyone working on CMX, advisors, employees, volunteers and contractors, have a deep passion for our mission. They’re here for the right reasons and that’s a standard I never want to sacrifice. They’re also highly talented and ambitious. In the future, team building will be harder as we grow but right now, I couldn’t be happier with the squad we’re running with.

5. Communications (3):

Transparency is something that comes naturally to me. I enjoy sharing and being open about learnings (as you can see in my writing). Where we really need to improve is in our system for communicating regularly so that we can get things out of our heads and in a place where we can take action on it. This also ties back to the need for more specific plans. By having a specific plan we can have measures of how we’re performing against that plan and have open conversations around how to improve it.

6. Empowerment (4):

This is something that comes to me naturally as well. I enjoy seeing the people around me succeed and I want them to feel real autonomy and ownership over their work. This will be put to the test when I hand off ownership of our conference to the person we hire to run all CMX events soon.

7. Presence (4):

Again, we’re so early and such a small team that there aren’t many challenges here. We’re all executing and have our hands in a lot of projects. I’m highly present with our team. If there’s one area I want to keep in mind as we move forward is to stay present with our community as well. I don’t want to get so heads down on work that I forget to stay present with the people we’re serving.

So with this, I have a good measure of where I’m at now as a leader and the specific areas where I’d like to improve.

My plan is to go through this process every quarter to track how I’m improving as a leader, and prioritize where I need to improve in the future.

I’d love to hear if any of you give yourselves a rating and how you think about improving your leadership. Also share any other books or articles about leadership that have inspired you. Comment below.

Here we go… new year, new challenges.

One of my areas of improvement for 2016 is to improve my focus. But I haven’t improved it yet so I decided take on a whole bunch of challenges this year. They are:

  1. Write (and publish) every day
  2. No alcohol for all of January
  3. Wake up at 6:30 on weekdays (and stick to my daily plan)
  4. Meditate every day
  5. Cook 2+ times per week
  6. Read every day for at least 15 minutes

Easy right?

Well the writing challenge might be the one I’m most excited about. I love writing and when I’m writing consistently, life seems to move in the right direction. It brings me clarity, it holds me accountable and it allows me to share my mistakes and lessons with others which has always been extremely rewarding for me. I once wrote about why you should build a habit of writing every day. Time for me to recommit to my own advice.

The last time I did a writing challenge it was for 100 days. Lets see if we can make it a 365 thing.

I’ll be mostly publishing here, but will also be writing on Medium and CMX. Maybe some occasional guest posts for others too.

I’ll be writing about:

  • Community building
  • Leadership
  • Productivity
  • Entrepreneurship
  • Whatever else inspires me at the time

It may not always be long. It may not be pretty. There may be some cussing and typos. I may even write some of these drunk (after January). But the most important thing is that I’m consistent. Every day, I will write, and hit publish. I promise you that much.

If you want to follow along, subscribe right over there in the sidebar —>

Want to join me in the writing challenge? Join the fb group where we can hold each other accountable (brought from the dead from the 2013 challenge).

You can see a full list of all the posts I write during this challenge here.

scissorsThere are two kinds of people.

There are people who rise you up, give you energy and make you feel like you can accomplish anything.

Then there are people who do the opposite. They drain you of energy, they make you feel like you’re not good enough and take away your clarity.

I’m a people pleaser. Or said another way, I’m addicted to making friends. I really want people to like me. As a result I end up spending way too much time with that second kind of person.

And they LOVE hanging out with me, because the energy that drains from me fills them up. They talk about themselves a lot, they brag, they flaunt and they use you as a way to make themselves feel good.

Do you find yourself spending time with people like that?

I recently decided to cut out one of my relationships like this. It was really hard because I consider them a good friend. But I realized that every time I spent time with them, I’d leave feeling worse about myself. So I stopped spending time with them.

I immediately felt better once I made that decision.

I realized it let me focus my time on developing relationships with the people that rise me up, and that I rise up. When it’s mutual, it’s magical. Those are the people you should focus on.

You can apply this same approach to your team. You can choose who you get to work with. Great teams are built of people who help each other succeed. When you hate your job, it’s almost always because you’re surrounded by people who bring you down.

Same goes for social media. Do you follow people that make you feel like crap every time you see their posts because you get jealous? Unless you have a massive paradigm shift, you’re not going to stop being jealous any time soon. Just unfollow them.

Cut out the people who bring you down. Spend more time with the ones who rise you up.

I’m constantly experimenting with different ways to improve my productivity.

For a long time in my career I was consistently, horribly distracted. I didn’t have any systems in place to keep myself on track and my productivity ebbed and flowed from week-to-week and even hour-to-hour.

I can’t say I have it all figured out. I go through phases where I’m really productive and phases where a fall into a rut. But lately I’ve been able to keep myself consistently productive and when I see a rut coming, my systems help keep me on track.

The entire CMX team works remotely and we often work different hours, so it’s really important that we develop the individual discipline to stay productive and get our work done.

Here are a few simple changes I’ve made that helped me become more productive in the last year.

1. Limit and condense meetings

I love meeting new people. As a result, I have a hard time saying no to meetings.

I used to just accept all meeting requests that came my way and I’d let the other person choose the time and place. This caused a lot of issues as I’d find myself hopping from meeting to meeting throughout the day, running all over the city with just small chunks of time in between to actually do work.

I realized I needed to gain some control over my meetings. I did this in three ways:

1. I try (sometimes I bend the rules) to book all of my meetings from 12-2pm every day. That’s it. I’ve been doing this for several months now and it’s completely changed the game.

2. I started saying no to meetings when I feel that we can accomplish the same goal over email. So if someone wants to grab coffee to ask me questions, I might ask them to send questions over email instead.

3. I started controlling the time and place by…

2. Using

In order to control the timing of your meetings, it’s important that you can be the first one to offer up potential times.

This app,, has been the best new tool I’ve discovered in years.

Basically whenever someone emails me asking for a meeting, I can say “Sure, let me know if any of these times work”. With just a few clicks, plugs in the times I have specified are available (12-2 every day) and the other person can simply click on one of the times to book the meeting and have a calendar invite sent.

It looks like this:

Screen Shot 2015-01-16 at 5.30.30 PM

That means I control the times that we can meet. It also means I can often control the location since lets you put in a location.

As a result I spend less time going back and forth on scheduling, I have better control over the timing of my meetings and I don’t have to travel to meetings as much.

3. Organizing my emails into buckets (inspired by Andreas Klinger)

I’ve admittedly only been experimenting with this for a couple weeks but it’s already been working out really well.

I was inspired by Andreas Klinger’s article about how to use gmail more efficiently. I tried his system and the format didn’t work perfectly, but I was able to adapt it to work for my needs.

This is what his system looks like:

klinger email

I basically adapted this by putting the buckets below my inbox instead of the side and I changed the purpose of each bucket to fit me needs.

As emails come in I can sort them into 4 different buckets:

  • Needs a response that will take more than 2 minutes
  • I need to follow up on this later
  • This has information I need later (travel plans, event tickets, etc)
  • Reading list (articles or links I want to check out later)

The unique thing I learned from Andreas is using stars or other symbols to organize the emails instead of folders, which really streamlines the process.

4. Optimized my todo list using a notebook and my own system

I’ve tried SO many todo apps in my career and nothing has ever really stuck. Eventually I started just using a simple notebook and over time adapted my system for keeping track of everything.

I’ve now been using this system for about a year and I love it. It’s perfect for me.

Here’s what it looks like:

todo list

  • Every time I want to add a new task, I just add it to the bottom of the list
  • I add an empty circle to the right if I intent to do it today
  • I can only have 3 empty circles at a time (this is the most important part)
  • When I finish a task, I fill in the circle (feels great!) and cross out the task
  • If I need to prioritize the circles, I can fill them in with numbers
  • Sometimes if I have a lot of tasks and I want to wrap my head around how long everything will take, I’ll write a little number all the way to the right making how many minutes it will take (like where I wrote 30 in the picture)
  • Every Monday, I take all the tasks that haven’t been done and I start a new sheet in my notebook (always on the left side….the right side is used for goals, reflection and planning)

5. Writing down my ideal daily schedule and keeping it in front of me at all times

This is something new I’m trying this year that has worked as well. I wrote out my ideal daily schedule on a sheet of notebook paper, along with my goals for this year.

I keep it on my desk in my room so I see it every morning when I wake up. I need to make another copy to keep at my desk at work.

Basically, it’s my default.  I don’t always keep to that schedule exactly but when I feel overwhelmed with the day, or I’m not sure what to do next, I can refer back to that daily schedule.

Here’s what it looks like:

daily schedule

6. Taking time to reflect and plan, every day

As you can see in my schedule, every morning I take 15 minutes to just review my todo list, my goals, and set a plan for the day.

I make sure to do this before I open my computer, before I start responding to emails and before I start doing any real work.

This way, I take a proactive first step in my workday, I can identify the things I know I definitely want to get done above all else, and I don’t start my day catering to other people’s needs.

7. Start every week fresh and revisit goals

As I mentioned earlier, every Monday I take all my tasks that weren’t completed and I move it to a new sheet in the notebook.

I’ll also revisit my goals for the week and write them down. These goals are what set the priority for my tasks. So every time I add a new task to my list and I have to decide whether to do it today or put it off, I look at the goals I wrote down and ask myself if this task will help achieve that goal.

I think this is really important, starting every week with a fresh mind.

Often, I end up just crossing off tasks because I realize they weren’t that important. Or I’ll find that my goals have changed since the last week and I need to adjust my priorities.

By looking at every week as a fresh start, I’ve been able to focus on the right things instead of just doing things because they were on my list last week.

8. Write down everything looming in your head

There will *always* be something looming.

That task that you just don’t want to do. That hard talk that you’ve been putting off with someone. That big decision that you have to make but you don’t have a strong opinion either way.

It’s these things that just loom over us throughout the workday that can really drain our mental energy and cause an incredible amount of stress.

One way that I’ve been able to deal with this is to just write down everything that’s on my mind. Sometimes I’ll actually write down “What’s looming?” on the right side of my notebook and try to think specifically about the things that have been bothering me.

This way, it’s out of my mind and onto the paper. And once it’s on the paper I have the choice to face it right there or put it off longer. Either way, I can address it instead of keeping it as this vague ongoing struggle in my mind.

9. Using Slack to communicate with my team

Slack has been a huge productivity booster for our team. It’s greatly cut down the amount of email we send each other.

And if there’s any way to improve productivity, it’s to reduce the amount of email you have to sort through.

I highly recommend using slack or some sort of simple chat application for your team to discuss the smaller things that come up throughout the day. We only use email to discuss larger projects that we need to plan and structure in depth.

10. Got a consistent desk at a coworking space

For most of my career I’ve worked from home or from coffee shops. I’ve had a lot of fun with it and I’m actually really productive at coffee shops.

But recently we got a couple desks at Galvanize, an amazing new coworking space in SF. I have to say, I really enjoy working at an office.

It all comes down to creating routines and consistency. If I had to boil down all productivity advice into two words, it would be those two.

So having the same office and desk to come to every day, having a space where you can focus and not having to make a decision every morning about where to work can be a huge boost to productivity.

The CMX team has the option of working remotely and we can all work whenever we want. So for me it’s not necessarily about having to have your team in the same office. It’s more about creating consistency for yourself.

11. Meditate every day

I’ve experimented with meditation for a long time but only recently did I make it a part of my daily morning routine.

I can’t say enough about how helpful it’s been. When I wake up, my mind immediately starts racing. All the tasks I have in front of my, the decisions I’m facing, the challenges ahead all come rushing in at once. It’s a tough way to start the day.

Meditation has really helped manage that. I only take about 10 minutes to sit quietly in my room after doing a quick workout and rest my mind. I let each of those thoughts come, I acknowledge them, then I let them settle.

The best meditation advice I’ve read in a long time came in this really short story (read the last two paragraphs of that page). That’s how I think of meditation now, letting my thoughts all settle to the bottom so my mind can be clear and address them in turn.

If my mind is really going crazy, I turn to to help guide me through meditation exercises.

Those are just some of the things I’ve recently been doing to improve my productivity and mental health.

What have you tried? What worked? What didn’t?

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 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.