Archive for Entrepreneurship

Entrepreneurship is …

Cheers to the Little Guys

In January, it’ll be 9 years of doing business in WordPress at iThemes.

So crazy to think we’re nearing a decade of work.

And I’m thankful for every minute of it, even the toughest parts.

Today, for a couple of reasons, I’m feeling a bit nostalgic.

Almost 9 years later now, one of my best friends isn’t even in WordPress anymore, others who started the same year as I did have now gotten acquired, while a couple of others are struggling this very week.

Additionally, there are now some big shadows being cast by big companies who play by different rules. 

But I always root for the underdog, the little guy, the small guy, the underfunded, outmanned team … the Davids … because, well maybe, I’ve always felt like I will always be that guy too.

So …

Cheers to the little guys (and gals), who still scrape and struggle each day, while continuing to invest in the community, build great products, support and value their people and relationships and seek to do business the right way.

Even though I am one of you, I am also your fan.

Do It For Them Or Let Them Figure It Out

One of the best pieces of advice (experience share, OK, OK) I got as a rookie entrepreneur trying to build our team was:

“If you want to see how good your team is and the health of your business, take two weeks off with minimal, if any, contact and see how they do.”

I’ve done it that now several times now over the last couple of years and have been so impressed with our team and their ability to do what we need to do, without me standing over them.

Too often I see entrepreneurs, particularly those with high levels of skills (particularly with tech), struggling with control and delegation. They simply can’t let go of certain things.

And I often struggle with delegation myself.

You know you’re struggling with delegation when you say:

“But it’s just easier, faster, better for me to do it.”

The key question is: “Should I do it for them, or should I let them do it and figure it out on their own?”

Sadly, what happens when we don’t choose to delegate, and them simply do it ourselves, is a whole host of negative things.

Sure, you might get YOUR ideal quality and result when you do it yourself every time … but you also become the bottleneck when you don’t train and delegate to others on your team. And you’re certainly not leveraging your team’s strengths and skills wisely.

Additionally, I know a lot of entrepreneurs who struggle with constant burnout and frustration (that often leads to anger and bitterness — been there, done that) because of this core challenge.

To make the scenario even simpler …. this recently hit home with me as a parent.

We have two young children. As infants, we had to do every thing for them for obvious reasons. But now as they are becoming toddlers, we’re realizing that they can become more autonomous in many ways and we definitely want to encourage them to do so.

I mean, I can’t imagine having a teenager who can’t go to the bathroom by themselves, or fix themselves a drink or a snack, but rather have us scramble to their every whim or need.

In fact, the goal isn’t that we don’t love and care for them … it’s that eventually when they are older and adults and go into the world, we want them to be fully functioning, healthy, happy and autonomous adults. (Even if we follow them around the world because we miss them.)

Back to business though ….

Delegation is probably one of the toughest things I do. It takes continual refinement, practice and communication.

It means letting go and empowering others to do their best. 

But I think there are numerous benefits to Letting Others Figure It Out Versus Doing It For Them.

Here is a graphic to illustrate what you typically get with each of those options:


As Dan Pink said in his bestseller “Drive,” it’s all about offering your team, your people, “Autonomy, Mastery and Purpose.”

Here are naunces, caveats, keys to empowering others: 

  • It doesn’t happen overnight — it takes time, effort and communication.
  • We all still make mistakes and that’s OK — that’s called learning. It’s only failure if we don’t learn from them.
  • Give more WHY than HOW — it’s tough at first to not give only the how. But if you know the strengths of your team and can clearly
  • Trust but verify — it should be known that although you trust your team, you have a responsibility to verify too. Checking up and in is part of that process. It’s also part of the coaching, teaching, training, mentoring part too.
  • Editing is improvement, not criticism — One of the toughest aspects for me in delegation is offering feedback at the end or delivery of a project or task. It should be about coaching and teaching, not blame, so that we improve all we do. [See No Blame Necessary] That’s why I like the word “editing” better for this. (ht Jon Acuff).
  • Teach values, more than practices — A couple years ago, one of my most trusted and valued team members made a decision. It didn’t turn out well. In fact, it kind of blew up in our face. When we started reviewing what happened together, particularly why she made that action, I smiled … because in her words I knew she had approached it with the values we hold dear first and foremost, and felt empowered and trusted to make the decision, even if it didn’t turn out well initially. If I had instituted a rigid system of practices for her to follow, it would have been worse — and likely we would never had taken action. But instead I sought to help her find any takeaways and reinforced that she took action based on our values (all good), instead of waiting on me or someone else.
  • They get the credit; I take the blame — It’s not that we don’t find out what happened and why. But I want my team to get credit for the awesome, values-focused autonomous work they do. And when mistakes happen, as the leader, I take ultimate responsibility. It’s my team. (And by the way, I get way more than my fair share of credit for what we do too.)
  • Have the end result in clear view — The best example of delegation was with my COO, Matt Danner. When we named him to that role, we paired him with a leadership coach (aka Smitty). But before they met, Smitty was so good to say, “What do you want the end result to be? What are your goals?” so that he could help train and shape Matt to be that person for me. It turned out rather well.

OK, now I need to get back to work on improving my delegating and empowering.

5 Things Great Leaders Do Daily

As Matt and I have been doing our Leader.Team business podcast, I’ve been thinking more and more about leadership.

I don’t do these perfectly every day, but reflecting back on what’s worked, and essential, to do consistently, here are the 5 things I believe great leaders do daily:

1. Shows up.

Leaders have to simply show up, do the work, alongside their team.

This should be assumed, but it isn’t always.

I said “daily” instead of “every day” because you can’t possibly show up 365 days a year, never taking time off, and show up for the long haul.

There are times you can’t or shouldn’t show up. We all need rest and recharging.

There are times when you’re not right or healthy (see next point) and then you shouldn’t show up, but you should as best you can, explain why you aren’t showing up. But if you’re “on the clock,” you gotta show up, be available and do the work.

Showing up says, “I’m with you. Let’s do this.”

2. Shows up healthy.

You have to tend to your own happiness and health first as a leader because if you’re not healthy, your team won’t be either. And I’ve shown up very unhappy and very unhealthy.

I know though that when I walk through my office door I need to be healthy. If my mood is terrible, it cascades to the team.

So I take my health and happiness seriously. Thus, I see my counselor several times a year, and in between when I am struggling through something. And try to maintain health in all areas of my life, not just for myself, but for my team.

A happy, healthy leader permeates through a team … it helps raise everyone up.

3. Cares.

If leadership had a one-word definition, it would be: Care.

Or three …. Genuinely, consistently cares.

It is all about empathy — “understanding and sharing the feelings of another.”

When I don’t take the time to listen and understand others, I make mistakes.

I know every decision I make affects people. If I don’t care about people, I make stupid, selfish, team-eroding decisions.

4. Communicates.

Put communication on repeat. The more I clearly, consistently communicate the better we are together.

Most good communication I’ve found is more about the why, then the how.

And honestly — sometimes I get really tired of saying the same things over and over and over again, even if it’s to different people. But good, consistent communication is the key to leading people. It’s an essential part of the gig.

I can always tell when I’m not communicating because that’s when rumors and conspiracy theories begin to fester.

In the absence of good communication, we, humans, will make things up. When we’re left to create stories that too often end up as horror, “end of the world” stories.

I can instantly recount numerous past experiences on teams where the leader didn’t communicate adequately with their team and I/we went straight to making it up for them. And in the process, it destroys morale and motivation.

5. Partners.

The better word might be “collaborates” but I like partner better.

People are not cogs in a machine. We are a group of people on the same journey together.

It’s one of the reasons I don’t ever use the word “employee” for our people. I go to great lengths to say, “my team” or “team members” whenever I speak about them to others.

Using this kind of verbage is more positive, more respectful and view them as people and care about who they are on our team and to me.

It says: “We’re in this together. And you’re invaluable to us and to me for reaching our shared goal together.”

Bonus: Consistency.

There’s been a theme throughout these 5 things great leaders to daily — it’s consistency. In fact, I shouldn’t have titled this post with the word “daily” but “consistently.”

I can simply set and forget it. They need to be tended to continually.

To become and remain a great leader, I have to do all these things over and over and over and over again.

If I don’t, it withers trust and respect for those who have signed up for our team, and can seriously jeopardize the journey we’re all on together.


Check out our Leader.Team business podcast for more thoughts and experiences Matt and I have had building and growing our team at iThemes.

Find Your Own Path

Find Your PathBe careful when you expect or demand someone else do it your way.

And be careful attempting to do it someone else’s exact way.

One size rarely fits all. And mileage always varies.

Especially in business but also in life.

I’ve actually found that it’s the quickest way to disillusion and then misery.

Your path might be the one true way for you, but not for me.

Your experience is likely not mine.

Your situation or setup is not mine.

Your beliefs, values, perspective are not always mine.

However, if I ask for yours, I’ll put it in the spreadsheet of my mind I use to make my own decisions, on my own path.

Yes, I may fail and make mistakes, but I’m determined to learn something from them.

I’ve often learned making my own mistakes is the key to unlocking what my happiness and joy is, for me.

When someone asks me my opinion or advice, I consciously try to default to what EO preaches in our forum groups … and simply share my experiences, and not advice.

Yes, sometimes I want your advice and you might want mine. Sometimes, I may ask you to tell me exactly what you think, or how you’d do it in my shoes.

With folly, I too often ask though, “If you were me, what would you do?”

But you’re not me. You’re you.

And if I do it exactly like you, I’m living your life, through the lense of your decisions, beliefs, philosophies and past … and not my own.

I will listen intently though and ask clarifying questions. I do that but it’s not to live your life, it’s to inform mine.

I weigh that input with what else I’ve learned to make the best decision for me.

And that’s helped me stay on the right path, my path.

I’ve been guilty of much of this though. When I blog (like this), tweet, take a call or do a talk, I say it all with deep conviction of belief … but it’s ALL based on my unique experiences. That’s my constant asterisk and disclaimer though as it should be.

And some of those experiences have, can and will change as I experience new things, ways, approaches and paths.

But many of us DO want to be told and directed what to do and I’ll admit, sometimes, I do too, especially with someone with more experience than me.

But knowing that I’m truly asking for experiences in deciding my own path, however they may come out helps in truly finding my own, is essential to sorting yours from mine. So now I know when I ask someone to share their opinion, advice, experiences or conviction, and they do so rather passionately or forcefully with me, it is merely their experiences baked in a crust of advice.

The best gold nuggets and informative, enriching experiences I’ve heard though is down in the deep core of it — the memories, experiences and stories, without me ever being a character in it. I’m simply hearing a good story.

When someone shares their experiences and emotions and reasons behind their path, without that deep-fried advice, it should sound more like, “I did X, because of Y, and Z is what happened.”

When it comes out like this, I can take my own truth from it and apply it appropriately.

This has given me immense freedom to be and do me. And to find the right path for me.

Only then, can I safely say:

I found and choose my own path …

… one that was mostly informed, sometimes guided, by all the experiences of others who graciously shared theirs with me.

Happy trails.

How We Do Recruiting and Hiring

We’re often asked by rookie leaders, managers and entrepreneurs how we do recruiting and hiring. We’ve had our share of misfires as well as excellent hires in the last 8+ years at iThemes.

In Episode 5 of our new Leader.Team podcast, Matt Danner and I talk about ins and outs of how we do it, even though we readily admit it’s more art than science. It’s a big subject so we broke it up into two parts.

Go download or subscribe to Episode 5 here