CaboPress 2018

The view from just outside my room at CaboPress 2018

It was the last night in Cabo. There I was, sitting on the patio after dinner, breathing in cigar smoke, listening to snippets of a conversation, then jumping into another, laughing hard with the group as we shared stories, enjoying drinks, and just taking it all in. It felt surreal and perfect. It was clear that we’d all had an incredible experience.

I had added my name to the CaboPress waiting list just the week before. It turns out I had stumbled into perfect timing. Chris Lema sent me an email – there had just been a cancellation and he had an extra room. He invited me to join and I booked my flights. I’d heard good things from former attendees, but I didn’t really know what to expect. I’ve never been to Mexico and the idea of sessions held in a pool was intriguing, but it seemed like it could also be terrible.

It was perfect.

Reflecting back on the past few days, a few highlights stand out to me.

A great host makes a big difference

13 years in WordPress and this was actually my first time meeting Chris. I’d heard good things and had positive expectations, but I didn’t know what to actually expect. I’m a bit of an introvert and being in a new environment where I don’t know folks well is a stressor.

On Monday evening, Chris called us together in the lobby to welcome us. As we pressed in to the group, I fought with my fears.. “Wow, I don’t know most of these people.. Do I really belong here? Do I have anything to offer?” After a few moments of light introductions, Chris cut right to the chase. He encouraged us clearly and directly – “You all belong here.” He reminded us that we each have much to offer and that we’re all here to learn and grow together.

I felt comfortable again and as Chris explained how the next few days would play out my fears transformed into excitement.

A great host makes a big difference. Chris Lema is a great host.

The benefits of “different”

Chris designed CaboPress to be inherently different. On Tuesday morning, we kicked off the first session on “High Value Courses”. By itself, it would have been a great session. Jennifer Bourne set the stage and then lead us into a focused discussion covering a range of strategies and tactics for thinking about and offering high value courses to our customers.

But having that session in a pool, introduced an entirely new dynamic. With no laptops, no presentation, and each of us in our swimming suits with various degrees of sunscreen applied, it was clear to our brains that this was different.

The environment made it hard to not be relaxed and engaged. As a result, I found the sessions more memorable and more impactful. When I think back on Allison’s session on writing a book or Brennan’s session on personalization, I have a whole additional range of senses and context that deepen the message’s resonance.

In a world with increasingly strong pulls at our time and attention, it was great to go to event that required less time (only two sessions a day) and gave more because it chose to be different.

The benefits of giving

Chris had set the stage for us on the opening night. He reminded us that we were each invited because we have something of unique value to give. Our hosts, each extraordinary and remarkable in their own right, were there to lead discussions, not lecture. Accordingly, we would each get out of the sessions what we put in.

I took the message to heart and focused my energies on leaning in, on listening, and on looking for ways that I could contribute my own experience and expertise.

As I did so, I discovered new questions to ask myself and began seeing the answers to questions I didn’t know I’d been asking. There is incredible inherent benefit to giving and the context and environment of CaboPress provides rich opportunity to do so.

What I received

On a personal level, I made new friends. Over lunches, dinners, and pool side chats, I got to know new people and deepen my context / relationship with folks I’d already known. Life is so much better with friends and I look forward to growing friendships with the folks I met in the months and years to come.

On a professional level, over the sessions and through personal and group conversations I developed a broader perspective, a deeper context, and a richer appreciation for the diversity of our open web ecosystem. I love WordPress even more : ).

I look forward to developing partnerships and creating new opportunities around the values we’ve identified individually and collectively.

CaboPress 2018 was excellent. Chris has created an extraordinary experience that will stick with me for years to come. If I get the privilege of being invited back I look forward to returning and if I don’t (Chris tries to keep alumni to less than 50%) I look forward to hearing the experiences of the new folks!

How To Write Proposals Via Email – Creating Clients Episode #4

In this episode we start with a recap of episode #3 (How To Start Conversations With Potential Clients) and then dive right in to the two principles of writing proposals via email. Then we look at the 7 elements of a proposal and explore each element in detail.

Episode Highlights

  • Anything that can be misunderstood will be. Work hard to make sure that the details of your proposal are as clear as possible. Keep context and the knowledge-level of the decision maker in mind.
  • Less is best. While working to include all the important details work just as hard to cut out anything that’s not really needed. Keep the process, your recommendations, and the “next steps” you suggest as simple as possible.

Episode Notes

First off, here’s the outline for your review:

  1. Introduction – Make a personal connection.
  2. Objectives – Your re-stated understanding of their objectives
  3. Recommendations – Based on the objectives.
  4. Scope – Based on the recommendations.
  5. Price – Based on the scope, with options as applicable.
  6. Timeline – Based on the scope and time constraints on your end / theirs.
  7. Next Steps – Your conclusion and guidance on the next steps.

Next are the examples I shared during the episode.


Example #1

Hi Robert!

Good afternoon to you! Thank you for your time and the additional details you’ve provided. They’ve been very helpful and I’m excited about the opportunity to work with you!

Example #2

Hello George!

It’s getting colder here in North Idaho and as beautiful as our winters are I’m going to miss the summer. Thank you for that link you sent over – there sure are some beautiful places to visit there in Florida. Enjoy the winter!


Based on our conversations so far I understand that your objectives with this project are as follows…


With those objectives in mind, here’s what I recommend be done..


With those objectives in mind here’s the scope of work I suggest we focus on together..

Next Steps

Do my recommendations, the scope of work, the price, and timeline sound like a match for your needs? If so, I’m looking forward to working with you! The next step is to let me know which package you’d like to start with and, from there, we’ll schedule a start date and I’ll send an invoice your way for the initial deposit.

If you have any questions or if you’d like to go over any of the items in more detail just let me know. I look forward to hearing from you!

Example Proposal

The following example is loosely adapted from an actual proposal I worked with one of my students to prepare. Enjoy!

Hi William!

I was talking to my wife last night and I realised where I know you from! We met you at the Georgetown small business meet-up back in August. It’s great to connect with you again!

Based on our conversation yesterday I understand that your objectives for this project are as follows:

  1. Keep things simple
  2. Get up and running as quickly as possible (you’ve already been waiting awhile)
  3. Keep the costs down in the beginning

Based on my understanding of your objectives I recommend the following:

  • WordPress Theme – WordPress is a highly popular tool that offers high quality designs (called “themes”) that look great and are optimized for mobile devices from the beginning. I recommend we choose a theme and implement some very basic customizations (adding in your logo, customizing the color scheme, etc)
  • Google Places Optimization – Using WordPress puts you on a good foundation for SEO. Building on that, I recommend that we start small and optimize your business listing on Google Places, which helps to ensure that your business shows up for local search results.
  • (Optional) Content Development / Photography – For all sites good content is the key to helping customers make the decision to contact you. I can schedule an interview to get all the relevant information from you and then write the content for the website on your behalf. I would also work with you to schedule a photo shoot to add high quality photos of your work / equipment / yourself to the website, which goes a long way towards increasing credibility.

As far as pricing goes, here’s what I can do:

  • Website + Google Places Optimization – $2500
  • Content Development / Photography Session – $1000
  • Website Maintenance – $1500/year – Includes free hosting + domain registration and unlimited minor updates throughout the year.

If budget allows, I recommend going with all three items (total cost $5000 for the first year, then $1500 thereafter). If you want to keep costs as tight as possible in the beginning you can provide your own content / photos and I can give you instructions on how to setup your own website hosting and register your domain, plus a short guide on making updates to your site.

As far as schedule goes, the good news is that by keeping things simple we’re able to cut down on time by quite a bit. Depending on which route you go I’d expect to have the project completed and online within 3-4 weeks.

Does that sound like a match for your needs? If so, just let us know whether you’d like to go with the whole package ($5000) or if you’d like to just go for the Websites + Google Places Optimization ($2500) and handle part or all of the rest yourself.

I look forward to hearing back from you!

Jonathan Wold

And there you have it! Notice that it’s simple yet conveys the relevant details and offers a clear path for decision making.

I have many more actual examples where that came from and I’d love to share them with you! Be sure to take a look at my new product / service opening today on

Next Steps

Share your questions / thoughts in the comments below or connect with me via email at I look forward to hearing from you!

How To Start Conversations With Potential Clients – Creating Clients Episode #3

In this episode we start with a recap of the last episode and cover the three principles of connection in further detail. Then we look at three different strategies for starting conversations with potential clients.

Episode Highlights

  • As counterinuitive as it may seem, our motive in starting conversations should not be about getting new clients.. After all, you have no way of knowing whether or not you and the individual you’re connecting with are a match for each other! I suggest that your only motive should be being of service.
  • Put conscious thought and energy into the conversations you start.
  • Take your local region, find interesting businesses / organizations, interview them, and post the interviews on a website you’ve created specifically for your local region.
  • Use business lists (local or market specific) and the phonebook to find interesting businesses and connect with them with the purpose, not of selling something, but connecting for the sake of connecting and being of service.

Episode Notes

We’ll explore the “Local Interviews” idea itself in a future episode. To get you started now, though, here are some examples of questions you can use in an interview, organized into three categories:

About Their Business

  • So tell me about your business.. What do you do?
  • How did you get started?
    • Ask further questions based on what they say.. e.g. “Oh, that’s really interesting! What inspired you to..”
  • What do you enjoy most about the business?
    • Look for opportunities to ask additional questions based on what they share..
  • What have you found to be the most challenging?
  • Are there any mistakes that you’ve made that you’d be willing to share?
  • Are there any successes you’re particularly proud of?
  • If you were to start all over again, is there anything you would do differently?

About The Region

  • Why did you choose [region] as your business base?
  • What do you like most about [region]?

About Other Businesses

  • What are some of your favorite businesses (besides your own) in the area?
  • What do you like most about them?
  • What advice do you have for other businesses wanting to start up in [region]?

Next up, introducing yourself to new businesses! First, here’s the format I suggest you follow, particularly when initiating contact via email:

  1. Introduction – A few short words introducing yourself and giving some context to what you do, particularly as it might relate to them.
  2. Interest – Something you noticed about them / their business that you’re genuinely interested in.
  3. Question – A genuine question you have about their business / work they’ve done, etc.

Here’s an example I’ve created:

Hi George!

My name is Jonathan Wold and I’m a business consultant here in North Idaho, specializing in web development / Internet marketing.

I found your business on the list of new businesses in our area and took a look at your website. You have a really interesting line of work! We’ve driven by your llama farm on multiple occasions and my son has been wanting to take a closer look.

Do you offer tours of the farm? Your website didn’t mention anything about it but I figured it would be worth asking!

I look forward to hearing back from you as you’re able!

Jonathan Wold

Last, let’s say you found a business with a website that is clearly broken. Here’s an example email you might send introducing yourself, pointing out the problem, and offering a fix:

Hello LouAnne!

My name is Jonathan Wold and I’m a local business consultant / web development specialist.

I came across your website today and I’m really interested in what you do! I’ve been a piano hobbyist for some time now but have been wanting to get more serious about my skills. Are you still taking on new students?

While I was on your site I noticed that the contact form on your “Contact Us” page wasn’t working! You’re using WordPress to manage the site and it looks like you were using a plugin called Contact Form 7 to setup the form. My guess is that the plugin was recently deactivated (perhaps during an attempt to update it) and that would explain why you’re contact page is displaying a shortcode instead of the actual form.

Are you working with someone to manage the website for you or are you doing it yourself?

To get it working again all you or your service provider should have to do is reactivate Contact Form 7. That can be done from the “Plugins” page within WordPress.

If you have any trouble or if I can be of any help in the process please don’t hesitate to let me know!

I look forward to hearing back from you!

Jonathan Wold

And that’s that! I hope those examples are helpful!

Next Steps

Share your questions / thoughts in the comments below or connect with me via email at

Creating Great Client Relationships – Creating Clients Episode #2

In this week’s episode I pick up from last week, recap the four steps in creating great client relationships, then explore the first step – connecting – in greater detail. I review the three principles of connection and share several examples from my own experience.

Episode Highlights

  • A connection is the intentional first spark of a long-term mutually beneficial relationship.
  • Place a high value on the connection, the relationship and let your motive be service. Ask yourself, “How can I be of help? What can I do to make their lives (their business) better?”
  • Connection requires conscious, directed effort. Listen intentionally. Take notes. Be 100% engaged.
  • Great relationships take time. Don’t rush anything. Don’t be quick to talk about prices.. Ask questions, listen.. Take as much time as needed. It’s worth it.

Special Thanks

  • Joshua Wold – For the great cover art!
  • Joslyn Wold (my wife) – For keeping the house quiet while I recorded (no easy task with a 1-year-old girl who’s teething!).

Next Steps

Share your questions / thoughts in the comments below or connect with me via email at

Introduction – Creating Clients Episode #1

This week’s episode serves as the introduction to the “Creating Clients” podcast. In this first episode I introduce myself, share a bit about my experience, and then dive right into explaining the concept of “creating clients”.

Episode Highlights

  • The best clients are those that are created in meaningful, impactful conversations that get to the heart of what they’re trying to accomplish and begin working towards solutions.
  • The first step towards creating “great” client relationships is to intentionally connect with an individual / organization with an attitude of service.

Special Thanks

  • Joshua Wold – For encouraging me, strongly, to start a podcast : ).
  • Nick Peterson – For letting me borrow his podcasting microphone and for dragging his feet on the ice bucket challenge.
  • Brennan Dunn – For tuning in to last week’s hangout-on-air and recommending a great book, which re-inspired me.

Next Steps

Share your questions / thoughts in the comments below or connect with me via email at