Archive for Entrepreneurship

Entrepreneurship is …

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

Two Things I’ve Learned Being an Entrepreneur and Parent

I was five years into starting and running iThemes when I added a new title to my resume: Dad.

Being an entrepreneur and a father is a very interesting combination. It brought up new issues, challenges and questions for me. In fact, it was one of the questions I went to my business group about before our first child was born, as many of them were already fathers and entrepreneurs.

My friend Ben Welch-bolen (and new father) has started a great new site called Entrepreneur Parents to share advice and experiences for those of us who are both. He asked me to chime in and I gave two answers, which you can also read here, but I wanted to share my thoughts to the questions here as well, so here goes:

With kid(s) and a business, what do you do to maintain your relationship with your spouse?

This has been our biggest struggle — simply making time for each other.

We quickly realized, no matter the cost, we had to do weekly dates. We found early on that night time dates (especially with infants) did not work well for us. We’d end up falling asleep on the date.

So now we do Day Dates, typically on Saturdays.

We can tell the difference when we skip a Day Date or simply don’t get one for a week or two. And continue to realize that it’s an investment in US, and we know the better we are together, the better we are for our children.

Plus, my mentor warned me …. we spend 18+ years raising kids and all the time-consuming activities and focus that includes … then one day they are gone, and we’re left with an empty house and a stranger.

We heeded that warning.

By the way, one huge benefit of having a physical office is we use it to get sushi and wine for lunch, watch movies, and talk on a couch while our kids are under the care of someone else at home. In the past, we would bounce around to different restaurants or places and spent more time, energy and money wandering like nomads than sitting and talking and enjoying quality time with each other. We still go out, but we know we have another “home base” to go to, something many others don’t have the benefit of.

What is the #1 piece of advice you would give an entrepreneur who is about to be a parent on how to balance those two worlds?

When I became a father, my business (my first baby) was in a good place. I tell people my busiess is now in kindergarten and under “adult supervision.” So the timing was really good to be able to focus less time and energy on my business than I did in the startup years and to shift that focus more to my children and family for a nice balance.

I have more time and energy constraints now as an entrepreneur and father, which I think is actually a very good thing. I have obsessive and workaholic tendencies and now I simply can’t (or won’t) do the things I did in the beginning, which gives me such a better perspective on life.

I’ve been able to focus on empowering and mentoring others in the business to do some of the things I frankly shouldn’t have been doing. I prioritize my time and energy so much better now.

The biggest thing I struggle with now is taking off my CEO hat when I get in the door at night and putting on the “Daddy” hat. It’s been a frustrating struggle, honestly. I’ve spent so much of the last 9 years being the leader, the one people look to, working with a team of adults and professionals, being able to give direction and know it’ll be done, that I have to reset my mindset when I’m home. I’m so much more of a caregiver, a teacher, a listener at home, but it’s also helped with business.

Patience is truly a virtue. And one I’m continually working on.


Go share your thoughts over at Entrepreneur Parents too! 


Bros, It’s Time To Hang Out More Regularly

Last weekend, I went on a quick but epic roadtrip with my youngest brother, Matt. On short notice I needed (and let’s be honest, wanted) someone to go with me to our New Mexico cabin (about a 9-hour drive each way) starting on Friday night and getting back on Sunday night.

Matt and I are seven years apart in age. He’s a police officer and I type for a living. We didn’t grow up in the same home, but we’ve always had a brother bond that even if we didn’t see each other for months, we would start where we left off.

So for 18+ hours on the road and all the in-between time when we weren’t sleeping (barely), there wasn’t 5 minutes of quiet between us. We talked about everything from children, marriage to politics and career … and of course our hopes and dreams and thoughts about the future. We toasted and drank some excellent Balvenie. We grilled veggies and steaks. And yes, there were plenty of pranks, shenanigans and laughs.

After the trip, although we were both exhausted I could not wipe the grin from my face if I wanted to.

And then after the trip, I read this article titled “The biggest threat facing middle-age men isn’t smoking or obesity. It’s loneliness.” And it got me thinking …

It’s true. At least in my life.

Yes, I have an incredible, supportive wife who is my best friend and amazing children that give me so much meaning and purpose and joy and love. Yes, I have a lot of close friends. But because of the busyness of life — career (running a business) and family (chasing two kiddos around and prioritizing my marriage), I see it’s truth.

In fact, I think you can walk the halls of many nursing homes and see this truth:

Loneliness kills.

Here’s a couple of quotes that stuck out to me from the article:

“Loneliness has been linked to an increased risk of cardiovascular disease and stroke and the progression of Alzheimer’s.”

“In 2015, a huge study out of Brigham Young University, using data from 3.5 million people collected over 35 years, found that those who fall into the categories of loneliness, isolation, or even simply living on their own see their risk of premature death rise 26 to 32 percent.”

As I read further in the article, I saw more truths:

Men need an activity together to make and keep a bond.”

“That’s why Schwartz and others say the best way for men to forge and maintain friendships is through built-in regularity — something that is always on the schedule.”

The key takeaway from the article hit home with me: We, men, need a regularly scheduled activity, especially in mid-life. 

So it got me thinking about how I’ve tried to find that male bonding time …. and here are my thoughts.

My Goals for Guy Time

Just replacing on the activities with other friends, here are the most valuable values I have for those relationships that maximize those times:

  • Go deeper — the older I get the less I care about small talk. I want to get to the deeper issues of life. My best friendships are the ones where we skip the surface and talk about the iceberg of life — both the struggles and successes.
  • Be more open — my most valued friendships are the ones where I don’t have to wear a mask or a costume. I’m just me, being me. And vice versa. This is all about trust and respect. And no judgment. We all have skeletons in the closet. The most incredible experiences I’ve had is two humans being human together. Recognizing we all have emotions and feelings, hopes and dreams, whether they seem trivial to us or not. I’ve found I’m my worst critic and whenever I’ve been more human and open, I get open and human back.
  • Make lifetime memories — have fun and enjoy each other’s company. The best times are when we’re doing something fun, whether it’s white water rafting in Idaho (or New Mexico) or simply enjoying a drink while telling stories that become our legends. Life is so much about the moments you share.

Some Ways I’ve Found That Bonding

Here are a couple of ways I’ve found that CONSISTENT and ongoing time with my dude friends:

  • Monthly Mastermind Meeting — although it’s not a mastermind (and we have females in the group), for the last 5+ years, I’ve been meeting with a group of 8-9 Oklahoma City entrepreneurs (via Entrepreneurs Organization) every month for three hours. They’ve been my lifeline of sanity as well as success. It’s been so incredibly impactful on my success and sanity that I’ve also started another forum group in the past, and am in the process of seeding another one this year. I’ve found nothing like it in the world. Like-minded people, in similar stages of life, with the same values and goals, setting aside a block of time each month to work on our icebergs and share our lives with each other. The other one I’ve been a part of like this is one with five other WordPress peeps, but is mainly focused on work/career accountability.
  • Once a Year Retreat — Our Entrepreneurs Organization Forum group also does a retreat once a year for 3-4 days, typically in the summer around June. We’ve done some fun stuff together like fly fishing in Montana to flying jets in Vegas, but it’s always the times around the campfire that mean the most to me. I also look at PressNomics and CaboPress (conferences I try not to miss) as times for bonding with my business friendships. I shouldn’t even label them as ‘business,’ they are friends I’ve made through business.
  • Team Sports — I just recently returned to indoor volleyball, a sport I’ve loved since college, after the urging and push from my wife. In the past, Lindsey and I have also played softball and relished those new friendships and times. Although the team was co-ed, I enjoyed the camaraderie and bonding and looking to playing volleyball again in the summer season.

Filling in the Gaps with One-Off, Somewhat Random Opportunities

  • Roadtrips — my brother Matt and I are already planning our next roadtrip over the weekend. Watch out Moab, we’re coming for you in Jeeps! In August, we’ll be joining our dad and other brother and friends to go hunting in New Mexico. (I don’t hunt or like to hunt, but I won’t miss another trip with these awesome men.)
  • Lema/Miller Slumber Parties — my buddy Chris flew to Dallas to hangout with me for a couple of days and because we’re kids like this, we said it was our Slumber Party. We talked until way too early in the morning and had to force ourselves to go to sleep as it was so much fun. Slumber Party Party Deux is in a couple of weeks. I know, we’re geeks, but proud of it!
  • WordCamps — the Hallway Track is my favorite, especially at WordCamp US. It’s hard to get 5 feet before you’re talking and catching up with some awesome WordPress community friends. Some of my favorite memories are hanging out (and getting lost on subways) with guys like Michael Torbert way back at WordCamp Boston, or sharing one-on-one time with guys like Karim Marucchi over a good meal.
  • Portugal Pals — one way my COO and buddy Matt Danner and I stay close and in sync is through regular trips together. There’s something about flights and hotel rooms without much distractions that are always a blast. We just returned from a once-in-a-lifetime, epic trip to Portugal. #pals
  • Dad Dates — my buddy Jesse and I have children the same age AND gender. He graciously went with me to see the latest Star Wars movie recently. I also had dinner and got to see the OKC Thunder play (courtside, holy cow!) recently with my buddy Jeff. It’s awesome when you are in parallel life stages, and going through similar things.
  • Coffees and Lunches — I enjoy catching up with my buddies and making new ones (like I did recently when John reached out to me as he was traveling to OKC for a wedding).
  • Traveling — on our personal trips, Lindsey and I have a motto and mission: Make friends everywhere. And we have. I love making new friendships with those in new cultures and around the globe. It’s entirely changed the way I do traveling now. My goal isn’t just to see new places, but to meet new people. It’s so mind expanding and special. Our friend Marco and his family, on Father’s Day, took us on a full-day tour of Lisbon, Portugal. So much fun memories — made even more special when his mother gave us tiles that goes on her house (a very cool Portuguese tradition).
  • Partner Pals — some of my best memories of my business partners, Scott and Jay, have been on our trips, whether it was to visit the campus of Google and Yahoo or the White House. I want for more trips with these awesome men and role models.
  • Skype, Slack, iMessage chats, Facebook — it’s never a substitute for face to face, or elbow to elbow bonding times. But the article says men aren’t great at talking on the phone (I hate it) yet throughout the year my buddies and I seem to stay in touch via these text chats. My friend Jason is great at keeping up like this.
  • Reunions — after 20 years of not going to my high school reunion, I went a couple years ago and thoroughly enjoyed catching up with old friendships, although I have not kept in touch beyond liking their posts on Facebook.

Ideas for More Consistent Hang Out Times:

  • Once a Month In-Person Coffee or Breaking Bread — like every third Wednesday. It’s way easier for me to do lunches or daytime meetings than nighttimes with kids.
  • Once-a-Quarter Weekend Trips — very short roadtrips that get us away from the distractions of life with a focused activity — like watching a football game, or
  • Once-a-Year Retreats — as I mentioned I already do this with my Forum group … but another in a year would be super nice, like 2-3 days away.
  • Movie Night — whenever a new movie comes out, we go see it on Thursday night — if we can stay up that late!

Additional Thoughts and Caveats:

  • Spousal/significant other support is essential — My wife is my top relationship priority. Without the support of my wife, I wouldn’t do the things I already do, but thankfully she sees the value for my life, health and happiness, and I do for her retreats as well. We try to do regular checkins to communicate and see how we’re doing, one of the many reasons I’ve tried to winnow my business travel down drastically this year.
  • Too much time away — I realize with all these ideas, at some point, you can spend WAY too much time away from your family, which ain’t good. It’s all about time budgeting and again talking it through with your spouse and family. It’s interesting to note that Lindsey and I try to do these kinds of spousal retreats and getaways as often as possible. She comes first, always and forever.
  • Getting overscheduled — I try to have as few regularly scheduled meetings in my professional life as I can (let alone personal), and if I were to add too many things above, I’d get way too booked up, which would mean less time for family and family travel.
  • Prioritizing relationships — I realize there’s a limit to how many close relationships one person can build. Proximity is often the prioritizing factor just because it’s easier. Lema talks about how he approaches that here.
  • Gal Pals are just as awesome — over the years I’ve had so many special relationships with some awesome, wickedly smart, incredibly supportive ladies. I’ve found just as much joy with my gal pals and don’t want to leave them out in any way. In fact, looking over my Instagram feed for pics showed me how much time I have spent with these awesome awesome women.

OK, what are your ideas?