Advice from Jonathan Kennedy | Value Propositions & Delegating Weaknesses

Last time we talked with Jonathan, we wrote about how HeyCarson and Storetaster got started (Storetasker has recently been sold to Lorem Technologies). Today, we dive deeper into Jonathan’s advice for Shopify entrepreneurs, and it’s a gold mine. With his experience helping thousands of Shopify stores around the world he’s seen it all. Read on for incredible insights about the value of value propositions and why learning to delegate your weaknesses could become your greatest strength.

A Strong Value Proposition Makes Business Easy

As you might recall from our last article about him, Jonathan is the creator of the Shopify Entrepreneur’s Facebook Group. That group is the largest and most active Shopify entrepreneurs group on Facebook. As such, it receives a lot of posts requesting advice from experts in the community. And it’s through that particular lens that Jonathan has identified the most common issue with Shopify stores today.

“I see dozens of questions coming into the Shopify Entrepreneurs group every day,” Jonathan told me. “Most of them are about getting traction or about struggles with marketing. And when you dig down and you look at the store that they're running, there's one fundamental piece always missing: a strong value proposition related to the product that they're selling.” 

Jonathan argues that too many stores fail to think about the things that do or could differentiate their store from possibly dozens of others selling similar products (often the exact same product). What’s more, while Jonathan says the problem is easy to solve, it’s an all-too-easy problem to end up with in the first place. 

Can you guess the unique value proposition of this marker (4th in from the left)? Hint: it's different than the other markers in one critical way.

“It can be a half day exercise, creating a value proposition,” Jonathan said. “There are checklists and exercises available online. But one possible problem is that, because Shopify has made it so easy for people to build a store and plug in products, a lot of people don’t think about value proposition. They just add products and that’s it.”

According to Jonathan, nailing your value proposition makes building a successful business easy as pie, akin to rolling a boulder downhill instead of up. On the other hand, missing this crucial step in your store’s development is tantamount to lighting a pile of money on fire. 

“If you get this step right, it makes your ongoing marketing so much easier and it makes your go to market strategy simpler to execute,” Jonathan told me. “Sadly most people are not putting the time in to create a really good value proposition for their Shopify stores. And that's why they all struggle. That's why they're all spending and losing money on Facebook. That’s why it's an uphill battle to get a conversion. Because, after all, why wouldn’t somebody just buy the product on Amazon? Why wouldn’t they drive over to Walmart and buy something that solves the same problem?"

It was at this point in our interview where I noticed an interesting parallel between how customers choose to purchase a product and how I select Shopify entrepreneurs to interview for the blog. In essence, they are one in the same.

Website-stalking recent interviewee, Kenny Azama of The Wander Club.

Here’s my process for identifying potential interviewees. Notice if you can spot the similarities between that and how your customers might interact with your brand before making a purchase.

First, I identify shops with which we already have relationships. Then I review their site for ‘positive story indicators’. These indicators are:

  • A discernible brand
  • A compelling brand story or founder story
  • An active community (e.g., blog, social media, etc.)
  • A unique product

Finally, I test their receptiveness via multiple communication channels (Facebook chat, Instagram DM, on-site emails).

All of those things essentially add up to or overlap heavily with the concept of a unique value proposition. I don’t think that’s a coincidence, and I think Jonathan would agree.

“Every successful story that you see, the common element you’ll find is value proposition,” Jonathan said. “You'll almost feel it right away when you load the homepage.” 

That last line from Jonathan is incredibly powerful, because we all know it’s true. We do feel it when something is right or wrong, almost instantly. 


  • Schedule a day this week to outline your unique value proposition.
  • If you’re not sure whether or not you have one (you probably don’t), bring in a few semi-critical friends to dissect your website, brand, and business model.
  • Value proposition isn’t only about having a unique product. It’s the combined effort put into delivering a unique experience for a target customer. (Headphone Zone is a great example here because they don’t create their own products. However, their customer service and community building experiences are incredibly unique.)

Identify your Strengths and Outsource Your Weaknesses

As entrepreneurs, we love being in control. For most, that’s why live this life in the first place. And yet, as we grow our businesses, we must sacrifice ultimate control in order to scale. 

“To have a successful store, you need to deal with at least 25 to 30 different areas of expertise and there's no way you're going to be able to solve all the problems on your own,” Jonathan told me. “So the faster you can identify your strengths and make sure that you're putting your time as a store owner into the right things, the better. What I mean by that is understanding what's core to a business versus what are satellite skills that you can delegate.” 

For example, Jonathan told me he sees a lot of Shopify entrepreneurs that are proficient at bookkeeping, and so they hang onto the bookkeeping or accounting themselves. But Jonathan argues that skill isn’t core to the growth of your business. 

Yeah, you could code the next version of your store, but should you? According to Jonathan: no.

“I think even if you're good at something like accounting, you need to let it go,” Jonathan said. “Even if you're good at design and development of a website, you need to let that go. There are too many people who are really good at web design and trying to run a store. So their stores are beautiful, but that's the wrong place to be putting their time.” 

Jonathan believes core tasks–tasks which should be handled by the store owner–include designing your product offer, driving partnerships, and driving vision. And in the early days, at least, doing your own hiring is critical. 

Moreover, both Jonathan and I agree that this lack of delegation largely comes down to a lack of trust.

“I think people have to overcome the trust issue,” Jonathan told me. “It’s not a big problem when you’re launching the store, but when you’re growing the store. That’s when you really have to start relying on people. And entrepreneurs often, if they've gotten traction with the first part of their business, they have a hard time trusting people and they have a hard time managing others because they think other people can’t do as good of a job as they can themselves. And so overcoming that trust barrier is all about accepting that trust is a core part of being an entrepreneur. Otherwise you're always going to stay small.”

Lack of trust aside, there’s one other major reason that entrepreneurs fail to delegate: their own talent. In other words, founders with development skills or accounting skills may put off outsourcing those things for far too long to save money or to retain quality control.

“I can't write a line of code and I can't open Photoshop,” Jonathan said. “And I think that's what kept me away from the things I shouldn’t be doing, other than answering customer service emails and writing content for the first little while. Many entrepreneurs love to jump in and solve customer problems on their own. But I couldn't. So I was forced to find and trust other people to do those things. Ultimately, that was a really cool method for having me back off the stuff I shouldn’t be doing and for giving me time to focus on what was truly important: growing my business.”

Jonathan advises others to start this trust development by delegating to one person who can do about 70% of your output in the areas in which you excel. From there, your job is to mentor, lead, and to mold your new colleague into a much better version of you in regards to those same tasks.

“I love being surprised by people’s talent,” Jonathan concluded. “I took some risks early on with people and some mistakes of course. But now I like to say that I suck less and less over time at hiring people. And I believe that's a big lesson to learn. You have to take risks if you want to trust people, and sometimes they surprise you.”

Ryan Chatterton Editor, Content Strategist, Digital Nomad, Coworking Influencer, Lover of Wine & Tacos