Archive for Business

My First Real CaboPress

Written by Lindsey Miller

I just got back to work after a great week at CaboPress and thought I’d share some memories as well as takeaways and highlights of this year’s awesome event.


I attended my first CaboPress in 2014. I was able to join my husband, Cory Miller, who was a host, as a guest as Chris Lema the host and creator of CaboPress asked us our whole family to attend. We brought along our son, Caloway, and as luck would have it found out the night before we left that I was pregnant to what would become, our daughter.

So, my first CaboPress, although amazing, was one filled with kids and relaxing and not as much connecting with anyone else in attendance. Cory raved about it for another year before he could attend the next one, until this year.

Each morning I woke up early for this view.


For CaboPress 2017, Chris asked me to co-host and after he assured me that he was not joking I couldn’t stop thinking about attending my first CaboPress and actually getting to take part in all of the discussions and connecting with so many WordPress business owners.

The first day of talks I was eager to hear from Tony Perez about hiring lessons. If you haven’t had the chance to hear Tony speak or talk to him at a conference then you are missing out! He is someone I know I can listen to and will always walk away with something to implement or change about myself. He has a way of being funny which helps people like me not be intimidated by how remarkably intelligent he is.

During his hiring lesson it inevitably turned to firing as well. I walked (or swam) away afterwards really thinking hard about those decisions and their place in a good productive business. I think it takes awhile to get really good at hiring the right people and that leads to having to let go of the wrong hires, but because we are new and probably really nice people we have a hard time with those difficult choices.

Listening to Tony and others share their stories really made it more of a decision of practicality and also helping those who entrust us with their employment. I will never look at those choices the same again.

Next I went to Cory’s talk on mastermind groups. I am not going to do all of us a disservice by telling you all how wonderful and brilliant he is, because we all know it. I also am not going to go over the many insights he gave us about belonging and how being a part of a forum group as part of Entrepreneurship Organization has shaped his life. Nor will I tell you how many of the people who attended his talks belong to such groups or are looking for one to be a part of and that Cory really helped shape those new groups with some of the insights he has learned, such as accountability rules and the law of Gestalt talk. I won’t mention those things since I am married to him and you may not realize that I am unbiased and he really is fantastic to listen to and learn from. 

Wednesday brought talks by Sherry Walling on mental health, which I attended and Syed Balkhi on retreats. Sherry’s talk was well attended and as always brought many thoughtful answers to all of the questions she fielded. I was really moved by all of the questions that others asked, worried for and about their own actions and how they could potentially impact their employees. It shouldn’t come as a surprise when I find so many kind people in one place, but it still does every time.

Next up was a talk I led, “How to Build a Network,” and as is the custom at CaboPress I tried not to just talk at everyone, but lead a discussion amongst those gathered. I leaned on my knowledge of the political arena I am so familiar with and drew parallels between my skills there and now in the sphere we are in. We all got to laugh a little and also heard from some of my friends who know a lot about building strong networks, like Jennifer Bourn and Mendel Kurland.

On Thursday I attended talks by Tony, again, because I never miss an opportunity to learn from him and Jennifer Bourn, for the exact same reason. These are the types of hosts that everyone comes to CaboPress to be around. I personally just wanted to be near them hoping to gain knowledge by osmosis if nothing else.

Jennifer led a talk on “Branding,” and I am not lying when I tell you that I heard multiple people say it was THE TALK of the week. We all walked away with actionable intelligence for our businesses and future growth. I asked so many questions that I felt like I should just have set up a separate meeting. Jennifer (not unlike any other host), isn’t afraid of sharing her vast knowledge. She will tell you everything that she does or thinks if you simply ask. I was not the only one in her talk that tried soaking everything up that she had to say.

It is these talks and discussions that make CaboPress so amazing. I went in to this year viewing it really as my first time, so I felt a little wide-eyed and bushy-tailed for most of it and just tried to learn as much as I could.

It’s All About Relationships

But that isn’t all that makes CaboPress the conference everyone raves about.

It is the relationship building that is the most impactful for me.

Each night, Chris gave us topics to discuss and guidance on how to choose new dinner mates and restaurants. As there are many choices of each. I tried dining with new people each night and the conversations ranged from the personal to the professional. I feel like it was during the meals where I made really strong connections with people who I hope will be friends for a long time to come.

Not only that, but during the afternoon free time, I had so much fun and made some amazing friendships. The first day Cory and I ended up at a pool where Cori and Phil Derkson, from WP Simple Pay, were hanging out.

Soon we were joined by Carrie Dils and Katie Elenberger and we had a blast! We hung in the pool for a long time and then ended up on the beach catching fish with our hands and (some of us) body surfing. It will definitely be an afternoon I will remember for awhile.


On the shuttle in I sat with Erin Flynn, and we connected immediately and talked all week long. She has become someone I want to learn from and hope to continue to build a friendship with. David Payette and I didn’t get to connect and promised at the next conference we would, until we ended up on the shuttle home together and had an incredible talk with Katie during the ride.

Another night I told everyone about my theory of “Pretending Fancy,” and how I often live my life this way. And it resulted in much laughter and teasing the rest of the week.

The last night I stayed up way to late playing board games with Marc Gratch, The Ninja’s and Melissa Lema. At times I was laughing so hard I was crying. For a quiet night I snuck away with a few friends for a quiet evening of talking about our histories, our families and why we are who we are.

It is these types of experiences that make CaboPress the amazing conference that it is. No matter where you turn you are around incredibly smart, kind people who are looking to gain knowledge, but also want to help others. There wasn’t a meal shared or a drink poured that didn’t include great conversation and idea building.

For me, my takeaway is I left the week feeling much more empowered than when I came. I really did feel like Chris was joking with me when he asked me to co-host. But as the week went on and I really did have value to provide for other attendees it didn’t feel like such a joke anymore. I felt like I did have a place there. I was there to learn, for sure, but I also had experience to give.

I only made one huge mistake this year and that was not taking a ton of notes. I tried jotting things down when I got to my room at the end of the day, but I know I missed so much. So if I get invited back another year I will definitely be bringing my waterproof paper and pen with me!

Chris says CaboPress is the best business conference in Cabo San Lucas, I beg to differ. I think it is the best business conference anywhere in the world.


Why BackupBuddy Gold?

In the past I’ve been openly against “unlimited” and “lifetime” options, particularly in WordPress. (Don’t get me started on hosting.) You can check out my previous post on Sustainable Business Models in WordPress here for background.

This week though, we launched BackupBuddy Gold … which grants customers lifetime updates to all current and future features of BackupBuddy, our extremely popular WordPress backup, restore and migration plugin that is now 4 years old.

So you might be thinking, “Did you change your mind?”

Not really.

And I’ll unpack that below.

I’m sure there will be plenty of discussion, debate, and [gasp] criticism, so I thought I’d do a post sharing some thoughts about why we’re rolling this out. (I’m sure there will be comments that I don’t address here, so I’ll try to answer in the comments or by updating the post.)

First things first — we did NOT roll this offer this new package for BackupBuddy because sales were slow, declining or even plateaued. iThemes is financially healthy and strong, BackupBuddy is doing great, and our team of 20+ people is looking toward our next 6 years in business!

OK, so here are some answers to the question you probably are wondering about, “Why open the box?”

1. The real issue with unlimited is ….


Support is extremely expensive.

Particularly with what we’ve seen supporting commercial WordPress themes and plugins. That’s what I said about “compounding debt” in my previous post. (I use the word “support” about 15 times in that post.)

For instance, if someone buys the first BackupBuddy tier (2 site updates and support) and has to post in our forum, we’ve likely lost money. Compound that loss if Dustin, our lead dev, has to weigh in on the issue, which he does regularly.

That’s why we capped support at one year for BackupBuddy Gold.

For this conversation (one particularly debated within WordPress), it’s all about support.

Thus, BackupBuddy Gold does not give unlimited, forever, or lifetime support. We capped it at one year.

2. Renewal rates

We have some very loyal customers (who renewed every year and who we also offered generous discounts to for this offer — THANK YOU!). But the majority of people did not renew over the last four years of BackupBuddy.

Now we’re getting paid upfront for the equivalent of what we would have gotten paid over several years of renewals.

As the veteran and leader in the backup and restore space for WordPress, now those loyal customers will get a great deal to keep using BackupBuddy to back up their sites.

3. It’s a much higher price point.

We didn’t roll this out at $80 … we rolled it out at an introductory price of $297. That can and will probably change.

At $80, we wouldn’t offer one year of support plus lifetime updates. We think we’re giving it away now … so I couldn’t imagine doing it at a lower price point.

BackupBuddy has grown so much over the years and become such a more awesome product. Offering Gold at this higher price is more than justified because BackupBuddy is going to get even better and even more valuable over the years our customers will have access to it in the future.

4. We can always shut Gold offer down.

(… and of course grandfather in customers who bought it.)

We could be wrong. This could be a flop and a failure. And I’m ok with that.

That’s the thing with learning. But if we don’t try, how will we know if it’s good or bad? Without action, it’s purely an academic pursuit.

And I’m about action.

I’m tired of getting hung up in what ifs. We did plenty of that before launching this. We evaluated and debated this for several weeks and decided it was worth the potential risk to offer.

But I’m not afraid to fail. To step into the light and see if our thoughts and ideas have merit.

That’s why I reserve the right to be wrong about all the above and change my mind about any and all of this. 🙂


[Hat tip to Syed Balkhi for helping me think through offering what we now call BackupBuddy Gold.]

How to Eat an Elephant (Or Tackle Most Any Big, Huge, Enormous Project)

How to Eat an Elephant

Illustration by William Warren

In my late 20s I went back to school to finish my undergraduate degree. As a working adult, the daunting task of finishing that degree (I had at least 40 hours left) was overwhelming.

But I quickly found an accelerated adult completion program that allowed me to do it once a week for around 18 months. And in the first weeks of the program as we started getting ready to tackle our first class and tidal wave of homework, I started getting nervous, big time.

I hadn’t been in school in 5 or 6 years and even then I rarely did any homework or showed up for class. So needlessly to say, I was getting that sick feeling in my stomach again.

And that’s when one of the instructors gave me a piece of advice that changed everything:

“How do you eat an elephant? One bite at a time.”

It was odd advice at first. I didn’t know elephants were on ANY menu. But as the truth and practicality of that advice sank in, it changed me forever and my approach to big, huge, blistering projects.

Of course eating whole elephants in one bite isn’t just gross 🙂 – it’s delusional, stupid, and impossible.

But in our naivety or arrogance, we’ve all attempted to tackle projects that were actual elephants – monstrous skyscraper-like projects that simply swallowed us in the size of its scope.

Here’s what happens with big, huge elephant projects:

We bite off more than we can chew and we get choked up.

We get lost, overwhelmed, frustrated and impatient. We want instant results, but we haven’t counted the investment or cost, and thus we lack the commitment necessary to finish right.

We’re unclear of the goal, or don’t know what results we’re working toward.

We run out of energy and time or mismanage both.

We get sidetracked and distracted, bogged down and lost in the details, minutiae as well.

We give up too soon or hang on too long.

And to sum it up: We fail. We don’t finish. The project flops. And everybody is disappointed.

Sound familiar?

On an almost weekly basis I run into someone having the same elephant-eating problem I was once had … so I want to share how I tackle big, huge, insane projects and coach others to do the same.

Whether you’re tackling a project solo, or working on a team … doing something for yourself, or delivering it for someone else … you’re likely to be tackling the eating of an elephant.

So with that, here are the steps to eating an elephant:

1. Chill out.

Take a deep breath and calm down.

At this point, you’re just stressing yourself out needlessly. Emotion and adrenaline typically make things worse. So simply taking a moment to get some composure is going to help a TON.

2. Step back and get some perspective.

Review and clarify the results you’re seeking.

Ask yourself:

  • What outcome / goal are you trying to achieve?
  • What does success look like?
  • What are the benefits?
  • If you’re delivering it for someone else – what are their expectations?

Oftentimes, simply knowing why you’re doing something helps tremendously.

3. Start breaking it into small pieces.

This is the awesome part because I see all the neat parts that I’ll get to do.

To help figure out how to dice up the elephant, ask yourself:

  • What’s really needed to accomplish this? People, tasks, timelines.
  • How can I chop it up into small digestible bites?
  • If it’s still too mammoth and overwhelming, how can I chop it up further?
  • How long is each piece going to take?
  • What are the tasks I can do quickly?
  • What’s the most efficient way to tackle this? (Meaning which items should come first?)
  • If you’re delivering it for someone else – what are their expectations? And how does it differ from your own?
  • Is it collaborative project? Which pieces will each person take on?
  • Do you need someone else’s help?
  • Which task(s) will make the most impact?

4. Now, review the investment and the journey. 

Which your smaller bites in mind, figure out how long the journey is really going to take … or how long you’ll be at the table eating your elephant meal. This means count the cost in terms of time, money, energy, momentum, etc.

5. Start eating the elephant. One bite at a time.

Oh, and be sure to chew your food with your mouth closed.

And with that … here is some general advice for managing big projects:

5 More Big, Huge, Ridiculous Project Tips:

  • Don’t ever take on big freakin’ projects. In fact, the less of them the better. You only have time and energy for a few HUGE projects in your lifetime … so pick carefully. My big huge project is iThemes. I don’t have time for other huge projects, and I only have time for small bites of other’s big huge projects.
  • Think of all the ways you’ll fail. Shocking advice, right? It’s good advice though. Know your big bottlenecks, challenges, and obstacles ahead of time. You WILL hit roadblocks, or fall into ravines, and if you don’t think about it ahead of time, you won’t know how to get around or across it.
  • Report in regularly. Rangers at big national parks typically ask hikers and campers to report in as they make a big journey. Along the way, measure and report your progress. See what’s working and what’s not, or celebrate small milestones along the way. Accountability is a very good thing, ESPECIALLY for big, huge projects. Accountability also helps us prevent blind spots.
  • Have deadlines and milestones. And then HIT them consistently, religiously. Don’t give yourself much slack if any. You’d be surprised how pushing just one deadline or milestone creates a snowball effect, turning into much bigger problems and delays for your project.
  • The final bites of the elephant are ALWAYS the hardest. When you’ve been eating the elephant for a long time, you will inevitably grow weary and burned out. But that’s when you need to push hardest … to finish the last 10% of the project and ship and deliver.

By the way, I ended up completing my degree program. It was a great accomplishment … and I ate the elephant, one bite at a time using the steps and advice above.

How to Make Your Software Sacred

Just posted this over at Entrepreneurship Lab titled 11 Striking Traits of Sexy, Sacred Software. 

But here are the 11 S’s of Sacred Software with some examples:

  • Sync — Software should be available everywhere I want it to be, like my iPhone, then my laptop and yes, even at the public library I just used this week. (Dropbox)
  • Social — Software should connect me to others. (TwitterFacebookLinkedIn, yada yada)
  • Share — Software should help me easily share my life (or stuff) with others (WordPressPinterestSwap)
  • Stats — Software should help me measure and analyze everything I do. (Google AnalyticsNike+ Running App, or FitBit)
  • Sell — Software should help me sell my stuff (EtsySquareUpStripe)
  • Spend — Software should help me buy the stuff I want. (Amazon’s one-click payments, iTunes, [insert any app store])
  • Smart — Software should help me find and figure out stuff faster and easier. Yes, software should think for me. (Google’s autofill or shortcuts, Netflix recommendations)
  • Simple — Software should be easy to understand and use. Super bonus points if you don’t need a manual or have to ask questions. (TumblrUber)
  • Spam — Software should sift out the spam and noise in my life. (AkismetGmail)
  • Speed — Software should make things faster and streamline life for me. (CDNs, caching services, Mint, but let’s share the worst example of speed: Facebook Mobile)
  • Secure — Software should make everything safe and secure (1Password)

Read and comments on the full post at the EntreLab here.

How to Bootstrap Your Business: 7 Ideas

Over at my Entrepreneurship Lab, I just shared 7 keys to bootstrapping your business, which are:

  1. Start part-time
  2. Ditch the financial baggage
  3. Raise social capital
  4. Build your name & fame
  5. Pour solid foundations
  6. Dial in the experiment
  7. Just keep pushing the snowball

Go read the full blog post here and get the MP3 audio recording and slides in the member’s area here.