Archive for Entrepreneurship

Entrepreneurship is …

Entrepreneurs: Your Companion Guide to Maintaining Good Mental Health

Finally …. a tool, a resource has arrived for entrepreneurs on maintaining good mental health is here, written by my friend, psychologist and fellow entrepreneur Dr. Sherry Walling and her serial entrepreneur husband Rob Walling.

It’s called “The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You.”

I wish I had had this book 10 years ago when I started iThemes. It would have helped me better navigate the ups and downs of entrepreneurship.

So I’m buying a dozen of them as gifts to my entrepreneur friends this week.

This book was written BY two of us, FOR all of us.

If you’re just starting on the entrepreneur journey or already deep on it, this book is FOR YOU (and me). Whether you’re going through a tough season of life and business … or just humming along gracefully … this book is for YOU (and me).

I think of it as a companion guide to entrepreneurship, like a survive handbook for entrepreneurs climbing their own K2s.

It’s written by a true experienced expert, but in intimate human speak, with studies and stories abounding that brings what we all know and feel out in the open, with actionable help. It hits all the big issues we deal with … from depression and loneliness to family, stress and procrastination.

Right now, it’s $3.99 on Amazon Kindle. But it’s an invaluable investment in your mental health, which makes a chill $4 seem like they’ve given you no reason not to go get it right now. (In fact, I’ve got it in paperback and Kindle versions.)

And by the way … I’m not just shilling my friend’s book. And I don’t get anything from it, other than to help other entrepreneurs know about a key guide in the often lonely, often misunderstood entrepreneurial journey.

Sherry and I met last year and we instantly hit it off. Not only is she an amazing human but she’s extremely experienced and talented professional.

We connected over our common interest in the mental health of entrepreneurs. Then we worked together on several initiatives for entrepreneurs (and their spouses) through her work and I hope to work with her again very soon.

So when she told me she was writing a book for entrepreneurs last year, I all but begged her to get it out as fast as she could as I knew so many entrepreneurs are hurting and in need of her work and help, just like I have.

In fact I recall saying to her, “We (entrepreneurs) need this in the world.”

When I started sharing My Iceberg a couple years ago, I longed to have a practical tool and resource to share with others to navigate their own Icebergs day by day.

And today … it is here.

Go get it. Use it. Reference it.

I have, I am and I will be doing the same.

P.S. — Thank you Sherry and Rob for opening up your lives and sharing your stories, experiences and expertise with your fellow entrepreneurs. Today, we’re better for it.

A Decade In Business: 10 Things That Got Us Here

In honor of our 10 year anniversary at iThemes this month, I looked back and reflected on what I’ve learned, that has made the most impact to our success and longevity in business.

Here goes:

1. It’s all about people.

The real reward in business is people.

Profit is awesome and kind of essential. But the people make it fun, joyful and special.

None of this would have happened without people, beside me, behind me, often in front of me. The ones who’ve done the overwhelming bulk of the work to get us here.

And it can’t just be any people … they have to be really, really, really good, committed, passionate, talented people.

The ones who care. The ones who love what they do and who they do it with and for.

When you get people like that the thing you must do is find out how to set them free and get the hell out of the way.

So invest in people. They will invest in you. Richly.

When you invest in people and they blossom and bloom before your eyes …. that’s what has made these 10 years so incredible.

In 20-30 years from now, when I look back at this decade at iThemes, the things I’ll remember are the people I’ve walked with, fought with (and for) and the things we did together.

Caring for, protecting, loving on, coaching, mentoring people is a big investment but one of the best I’ve made. It also makes you a magnet for more good people.

And frankly, it’s just the right thing to do.

2. Find your sidekick, fast.

For the first couple years of business, I didn’t have a sidekick. One who would make me better. One who was strong where I was weak, weak where I was strong. One that completed the picture for me as a leader and manager.

And truly I’ve learned … having a sidekick means you don’t walk alone. You don’t shoulder everything on your own. You don’t make decisions in an echo chamber. You don’t fight alone. And that person just makes you better. And what you’re doing together exponentially better.

Matt is my sidekick. I couldn’t have dreamed of a better partner. He is the definition of the ideal sidekick.

We met each other over 12 years ago now as friends. Then he started working with me … and eventually I named him the Chief Operating Officer.

Looking back, one of the smartest decisions I’ve made in business that has translated to our success and my happiness.

He’s not even 30 years old … but he’s an incredible leader, manager, all around Swiss Army knife. Those who know him and what he can do are jealous I have him. Those who hear about him, want to meet him. For good reason.

For years, we’d simply would use the hashtag #pals in our chats or texts to summarize our friendship and partnership when the going got tough (and it often has).

In the most recent season of time, we’ve got a new one … #backtoback.

Back to back is when you’re surrounded by an overwhelming force. You’re outgunned. You’re outmanned. It’s just you two against the world … you go back to back and fight your way out. Together.

He’s had my back. I’ve had his back. And I can’t imagine getting him without him.

3. Be early.

When I stated iThemes in January 2008, we were one of the first commercial WordPress product shops out there (starting with WordPress themes). We launched at a critical time in WordPress. The right moment. The right time. And we were EARLY.

I can’t overstate the momentum that gave us for the last 10 years. Mostly, I’ve just tried to keep riding that and using that momentum, adding more to it, to become a force that helped us arrive here.

It means more people know us, like us, trust us because we’ve had a lot of time to do it all and we were, yes, EARLY.

Being early was crucial for us, although so many others were not “early” and still have had great success too.

For us, though, we have used it and keep using it.

4. Be lucky.

I like to think of myself as a smart guy … but I know I’m a very lucky guy too.

I’ve joked with our team that if I wrote a book about the history of iThemes it would be called “Stumbling Successfully.”

We’ve made a ton of mistakes. But we’ve also been lucky and then made our own luck by doing good, working hard, taking care of people and not giving up.

We want to keep being lucky, which means we’re open to opportunities and will pursue them backed by hard work.

5. Email marketing was/is our secret sauce.

It feels weird to throw this in here, but it’s so true. We have used email marketing since the beginning, and only amped up how we do it every year to be better and better.

But if you were to see a chart of our sales over 10 years … I could show you when we sent out emails.

We used it when others neglected or thought it was vile black magic. But we did it right, respectfully and to the max.

6. Try not to puke on the ride, OK?

I got on this roller coaster 10 years ago. And so many times just when I think I got the ride down and know where all the big curves and drop-offs are … I find new ones.

I think of one of the key characteristics or strengths required as an entrepreneur is simply: resilience.

Being able to take a gut punch … and get up and keep fighting.

Sometimes the punch is in the face. Sometimes you’re lying face down on gravel and being dragged.

And so many times, I’ve thought, “Maybe the next action I’ll take is to just go throw up now.”

But you gotta keep going. One foot in front of the other.

Looking back at 10 years worth of key events, moments and crises, somehow I just kept going. Somehow we just kept going.

And try not to puke.

7. Seek out and cherish the people who run in, while others run out.

I’ve talked about this at length during my talks over the last couple of years.

I call my people my Life Support Team. (I talked extensively about this in the Iceberg of Life.)

They are the people who run into your life when everyone else is running out.

When you’re down, you’re crying, at your worst and maybe just want to quit …. they are ones who say, “I got ya, bro.”

So many times as the leader you’re the person charged with reassuring everyone else that “it’s going to be ok.” But sometimes, when you’re at the bottom, it really helps to hear someone else say to you …. “everything will be ok.”

There is a tomorrow. There is hope. Let’s pick you back up, brush you off and get you going again.

A huge part of that team, beyond my wife (who is my first and most critical partner) and family and friends, is my entrepreneurial peer group. Other entrepreneurs who are on a similar path, sharing the same values, and just want your best.

In times of troubles these people stand out … they stay. Right by your side. And vice versa.

8. Always be tweaking, experimenting, trying new things.

For years business friends asked, with a very puzzled looked, why we kept venturing into new products and even areas. Often failing.

Part of the answer is it’s how I’m wired. I like experimenting. I like new challenges. I like new projects. And I like diversifying.

I know how fickle this game can be. I don’t want all my eggs in one basket.

But it’s also about making sure we’re continuing to experiment, to improve so that we can keep this thing going for a long, long time.

So we try new things and fail. Mistakes are learning though and we’ve tried to learn better from those mistakes.

I think the opposite choice here is complacency.

And that’s too often the easier choice. Just to coast, put things on automatic pilot and think nothing will ever change.

Just like our sales related to emails, I can probably show you the times we got complacent and put things on cruise control. It’s very dangerous.

9. Adapt and innovate or wither and die.

If we had kept doing only what we did in 2008 … we would not be here today.

If we hadn’t adapted and innovated, stepped out, took risks, made mistakes, lost money on experiments, I firmly believe we’d be out of business.

Year after year we’ve tried to look on the horizon and see where things are going and position ourselves to stay relevant.

It’s not easy. It’s often painful. But it’s necessary. And it’s the reason why we’ve lasted 10 years.

It’s often a hard pill to swallow, especially after you’ve been through a particularly rough patch and things are going well.

But if we were watching on the horizon and sensing the changes, we could have easily gotten consumed by them.

10. Just be good people.

This one is epicly simple: Just be freakin’ nice, generous, gracious, humble, helpful people!

I think it’s wired into my DNA and how I was raised … but I’ve always wanted to just be the good ole small town Oklahoma boy to everyone around me.

Ready to help. Ready to listen. Open to possibility. Open to sharing. Open to connecting.

And I think it’s been a huge part of our success here.

When others stirred up controversy, or choose to be the antagonist … I simply choose to be who I am — a good, generous guy to others (including many of our competitors).

I believe it’s the reason people want to do business with us today, whether that’s partnering with us, promoting us or coming to work with us.


So there’s my ten. The same ten I’d bet on to get us to through to the second decade.

Quality Time Is So Critical With Your Most Important Partner

This week my wife and I have been on vacation in Jamaica with some good friends. It’s been an incredibly relaxing week so far. Lots of pool time, great food and drinks, laughs, reading, and yes, for me, trying to attempt something close to this on this Red Slide here.

But most of all — it’s the quality time with my most important partner — my wife Lindsey.

This week came at the right time for us. Even though we do weekly “day dates” together, we both acknowledged we needed some extended time away, from the busyness of life and the craziness of toddlers, just for us.

Early on in our relationship, we realized that regular, consistent, dedicated times to spend alone together was vital to our marriage and our health and happiness.

Just quality time together talking, reconnecting, holding hands, dreaming, reflecting, watching movies, reading books side by side next to a pool …

This week has been such an incredible reminder of the importance of quality time together.

As entrepreneurs, sometimes carrying what seems like all the worries and concerns of the worlds on our shoulders, I think it’s too easy to forget that and to set time aside just for you and yours. I know it’s true for me.

But the other thing is … realizing that importance for our most important partners — our spouses and significant others.

So a couple months ago, Dr. Sherry Walling and I started dreaming and planning a Couples Retreat just for entrepreneurs and their spouses/significant others. It’s coming in a couple of months.

It’s a time for you to reconnect with each other … in the company of other couples who get you and the often-challenging life you lead together.

Tickets are on sale now. We’re capping it at 15 couples, along with 3 host couples.

I think it’s a great excuse to put something on the calendar and to invest in your relationships.

Go check out more details about the ZenFounder Couples Retreat here. And whether you decide to join us or not for this retreat, I hope you’ll schedule some extended quality time together very very soon.

OK, now I’m heading back to the pool!


Find Belonging, Support With An Entrepreneurial Peer Group

In 2010, I was going through a tough divorce (aren’t they all) while my business was starting to really take off.

Despite the outward facing business success, I was also battling what I now know is pretty typical of the entrepreneurial experience: conflict, pain, stress, and perhaps burnout INSIDE my business.

It was the first time in my journey as an entrepreneur I thought maybe I’d rather work anywhere else.

And in so many ways I felt like my entire life was in full reboot mode. Or perhaps all my systems felt like they were crashing on me.

I can still recall sitting in my new little apartment, with sparse furniture (think an Ikea couch and bed), only Gatorade and cookie dough in the fridge, and feeling the empty longing of loneliness.

Not many people in my life at that time could come close to relating to what I was going through as a human combined with being an entrepreneur.

I was suffering in solitude.

And I was craving authentic relationships with like-minded people on a similar path who knew what living the entrepreneurial life — with its sometimes drastic ups and downs — meant and who were walking it every day, like me, and wanted to walk together with others too.

To be frank I wanted deep, committed friendships with people who just got me, who were willing to open up their otherwise much guarded lives to another human being, and to be myself with them, and to get support and encouragement.

I desperately wanted to share my life — the successes AND the struggles — with those who got the unique demands, responsibilities, pressures, stresses, worries and pains of entrepreneurship.

I wanted a bond. I wanted to take off my mask and be real, even if for a few moments or hours.

I wanted to know … I was not alone.

I also wanted to know my struggles weren’t any different than others. I wanted to hear their stories of struggle and triumph.

I wanted to use those stories to find my own truth in order to make my life better.

(Here are 5 Ways Entrepreneurial Peer Groups Improve My Life.)

The next year, I found that in a group of entrepreneurs meeting in Oklahoma City, where I live.

(Six years later, I’m still with that group every month for three hours …. and in a couple of days we’ll be heading out on our annual retreat.)

They were water to my thirsty soul. And now, years later, I know how crucial they’ve been to my health and happiness as an entrepreneur, husband, and father … and just human being.

If you’re like me … you need that too. Right now.

It wasn’t just this one isolated season of time, either, that showed how desperate I was for this genuine companionship … it’s every day since that time I’ve realized how much I NEED it.

I naively thought I could just keep walking by myself (yeah, Superhero Syndrome still has remnants in me) … but the truth I realized fully was that:

I NEVER WANT to walk alone on this journey as an entrepreneur again.

It’s a people and a place to belong.

We talk about riding the roller coaster of entrepreneurship, yet don’t surround ourselves with the team of support people for when the tough times come. (These are the rush in, while others run out people.)

We also say “work on our business, not in it” but we don’t often take time to work on and invest in OURSELVES.

Through my experiences, I believe we were as humans and as entrepreneurs meant to live and breath in community.


Not alone.

Together is so much better.

And as I’ve traveled and talked openly about how these types of small groups of entrepreneurs have had such a profound effect on my life, one key question ALWAYS pops up:

How do I get into one of those groups?

And until now, I didn’t have a good answer or solution to offer, and I’ve been on a mission to find a good answer.

Now I do.

I’ve partnered with Sherry Walling, a Ph.D. experienced psychologist who works regularly with entrepreneurs to start a new entrepreneurial peer group called ZenTribes.

We’ve taken the best of what I’ve gotten from my entrepreneurial groups, along with Sherry’s wealth of experience helping others in her practice, as well as working with entrepreneurs, to offer something tangible and good and impactful.

We recorded an entire podcast episode to talk all about entrepreneur groups and their benefits here.

We’re taking applications now for our next groups. Go check ZenTribes out and see if it’s time for you to take the next step in investing in yourself.

5 Ways Entrepreneurial Groups Have Improved My Life

Since 2011, I’ve been a part of 3 formal entrepreneurial life groups. Although that’s not their names, that’s the way I see them.

And the impact of those groups, the time I’ve spent in them, and the relationships I built through them have been priceless.

They have had a profound positive impact on my life and business.

In fact, I don’t think I’d survive without them. They have exponentially increased my health and happiness … and yes, my business has grown because of it too.

Increasingly I believe every entrepreneur should have some sort of small group of entrepreneurs to be able to do life together with.

Entrepreneurship is one of the toughest, most demanding and lonely jobs out there … and too often we try to go it alone.

Here are the most profound benefits I get from these entrepreneurial groups:

1. I’m Not Alone.

Entrepreneurship is one of the toughest, most demanding and yet loneliness jobs there is.

Having a group of people on the same or similar journey to share life and experiences together is one of the most profound, deeply impactful times of my life.

Every time I’ve met with these awesome entrepreneurs, I say to myself, “I am not alone. Everybody has the same problems, with different names attached to them.”

There’s a special hope that comes from knowing the universe hasn’t singled you out for misery.

My struggles aren’t as unique as I thought. Other people are often dealing with the same things as me, or will.

And through that experience, I have found unparalleled camaraderie and friendships that I couldn’t get anywhere else.

We, entrepreneurs, are a special breed, we deal with certain life situations, pressures and stresses that most don’t.

But these fellow entrepreneurs get me, are there for me, walking with me, sharing their life and experiences with me and vice versa.

It’s a place and a people to truly belong … and to never suffer in secret or solitude again.

2. I Learn and Grow and Improve My Life

Every time I meet with entrepreneurs I learn something new that benefits and improves my life.

There is no competition or judgment, but it helps me see areas I need to develop more and their example helps me model new behavior, especially in unknown territory (like becoming a dad for the first time).

Hearing others share their experiences over just giving advice allows me to know the full story, not just 140-character glossy version of it … and I get to draw my own takeaways from that.

3. I Can Take Off My Mask and Be Me

I can be open ….. and let down my guard and share things I can’t or don’t or won’t with others in my life (or business) in a safe, confidential people, without judgment.

Whether it’s a key struggle I’m wrestling with, or a huge success that I can’t otherwise share, I can in these groups.

Too often we simply bottle things up and then they inevitably end up blowing up in us. Or we check off a dream from our list … yet have no one to share that with.

I can be open, let my defense down and feel safe and embraced doing so.

4. My Life and Experiences Can Help Others Too

It’s tremendously rewarding to get help from others, but also to give help too.

By being part of these groups, I also help and support others to improve their lives and work on their struggles by sharing my own life and experiences.

It’s not about giving advice, or telling them what to do … it simply saying, “I’ve been through a similar situation and here are the details of it all.”

Being generous with my life and experiences is an incredible reward. We’re in this together.

5. Investing In Myself Benefits Everyone Around Me

So many times, we hear the advice — “Work on your business, not in it.”

But when are we encouraged to work and invest in OURSELVES.

These groups allow me to set aside time to invest in myself that benefits everyone in my life.

I hate booking my schedule full of things so I have a limited number of repeating events. But I also know I need a set, fix, recurring time. If I don’t have something on my calendar (fourth Tuesday of every month) I’ll come up with every excuse to miss meeting with other people.

This is a focused, set and consistent time that gives me a great dose of camaraderie as well as time to invest in ME and to give to others.

And my wife, my team, my partners and my customers feel the difference when I do.


Ready to Find Your Group?

Every time I’ve talked about the entrepreneurial groups I’ve been a part of, a number of people always say — How can I find one like that?

If you’re interested in these kinds of groups, I’m excited to share that I’m collaborating with Dr. Sherry Walling of, an experienced psychologist who works extensively with entrepreneurs, to start something new called ZenTribes.

It’s the culmination of several months of conversations and planning that we’ll be launching very, very soon.

If you’re interested in ZenTribes and what we’re rolling out … be sure to hit the link below to subscribe for our launch and upcoming groups.

Get Updates about ZenTribes