Kenn KellySpeaker // Founder // SaaS // WordPress // Culture

Founding Partner of 3 Tech Startups and 2 World Causes (all profitable). Redefining entrepreneurship through culture and boundaries. Bootstrapped, Angle Funded and Venture funded companies. Remote Work, Culture, and Lean methodology expert. Product development for 25+ products with over a 1M+ combined active users.

Recent Answers

Unfortunately implicit racial bias is still very present today. However I'd encourage you to change your point of focus - take your energy, talent, and wisdom and pour that into your product and company. You should spend very little time or concern trying to win over others in your industry - your main focus as an entrepreneur is to win over your customer. The vast majority of customers will care more about your product than your personal background - build a product they cannot say no to. Lastly, you can not afford to doubt yourself. Most of the world will tell you that you can't, you cannot be one of those voices. You believe your own voice more than anyone else's on the planet so be sure that you're your biggest believer.

Yes based on the hooks and templates in WooCommerce you can customize the flow of checkout to be anything you want. I know that's a simple answer but most things you can think of can be done in WC. Even pulling in live shipping rates via an API to FedEx, USPS, UPS, etc...

There are many routes you could take this with different membership plugins or subscription based plugins which would accomplish what you are looking to do. However, the best starting point for you is probably using an LMS (Learning Management System) plugin or theme. An LMS will provide everything you need out of the box and will be scalable for your future needs as you develop more courses, integrate quizzing or surveys, award badges or certificates, etc.

The LMS will integrate the membership or subscription tools you'd find in those plugins with all the other tools you'll need to create your coaching course.

Let me know if you want to dive in more.

The quick answer is everything you're asking for is possible and fairly easy to implement. You're scenario and desire to keep things scalable on a large network is the main purpose for WPMS. We've built over a dozen client networks some with more than 700 installations on one network. We have built robust tools like the which allow you to clone, copy, update, migrate, etc. with one click inside your network.

With MS you can run an admin level codebase for all sites while maintaining unique content as well as unique functionality and design if you choose. With domain mapping you can also have a custom domain per sub-site if desired as well. I.e. instead of having and you can have and

Once you have correctly configured your network and have tools like our Cloner the possibilities are endless.


Get data! Let your customers tell you through the data what you need to build. I would start by building the one browser you know for sure you're going to support. Roll it out and review your analytics to see what browsers they are using. If you have a browser that you don't support that is providing a decent % of your traffic you can prioritize that as your next browser to be sure you're compatible with. Much cheaper and quicker to let the data determine your development path than spend too much time on assumptions. At the end of the day it ultimately is just an assumption until you have data from your audience (not competitors or similar products and services).


You're going to need to baseline technologies - something to capture membership and manage members and something to deliver the content. Even in a low budget you can either merge to services/technologies or plugins together or find an all encompassing one. There are many more options than this but to help get you started.
Tools for Membership
- PMPro
- Woo Subscriptions
- Member Mouse

Tools for Drip Content
- Aweber, Mailchimp, Constant Contact, i.e. newsletter services with marketing automation built into them ('marketing automation' will be the keyword you'll want to do searches on to find the tool thats right for you)
- Intercom (not for low budget)
- Hubspot (not for low budget)

Tools that do both:
- Agile CRM (WordPress Plugin and Integration)
- Presspoint

Biggest thing to understand is that at the core you need two pieces - the first is a way to manage members (even if free) and provide secure content only to them. The second is distribute your content on a schedule. Like all things there are many ways to approach this but hopefully this gives you a head start. If you have more specific questions let me know.

Like most things in web development there are 100 ways to slice that pie - so this answer is by no means all encompassing of all ways to do so.

Depending on what your objectives are I would recommend one of two ways:
1. Use the built in WP gallery feature tied to the WP core. No extra code and thus you couldnt get any lighter than that. It already resizes the images to different sizes. To access simply goto "insert media" and look in the upper left hand sidebar for the gallery option, select your images, determine size, press insert. If you want to customize the wp core gallery functionality to show attributions or something similar a good wp coder could knock it out in 30 min or less.
2. If you want a lot of features and customizations an display and interaction I would recommend just getting Revolution Slider. It has more features than you could ever need and it can pull images into galleries OR it can pull posts in from WP and use the featured image, title, and any other custom field you have into the slider.

There is a lot more that could be said but that is a quick - to the point - response.


I think a better question is what do you need and what is your current skillset. If you have some understanding of development and or content management architecture WordPress would be the better tool for you. If you have no background and don't have incredibly complex customization needs then Rainmaker would be a better fit. For someone with little cms background Rainmaker will win the ease of use and appearance, otherwise versatility, seo, scalability, and customization potential - WordPress would be your winner.

Disclosure: in the last 5 years my company has built 600+ WordPress sites - however we have used many of the top competing CMS platforms and have researched Rainmaker and other hosted CMS alternatives for our clients and implemented some of those alternatives.

Great question, it shows your aim is on winning the marathon not the sprint. I agree with most of the advice in this thread. For us, it came down to putting a boundary around our work hours, in my last three companies there were never boundaries and we had what we thought were sweet benefits like "take as much vacation as you want" but really it just meant longer hours before and after your time off. We did an experiment called "40 Hours a Week No More No Less" testing to see if we could meet current responsibilities, stay profitable, and beat the competition. That experiment turned into a company policy three years and has been one of the most influential things we have done as a company. There isn't enough room to provide the full background but in short, by setting boundaries around our work hours it actually increased efficiencies and created a hyper focus on prioritizing the right work each week. You can read more about it here:

Absolutely, however I would say the approach is dictated by the fact you are wanting to build an "enterprise" SaaS product. The approach for an enterprise solution is quite a bit different than an MVP for a small single web product.

Assuming you see a need/demand for the product you are wanting to build I would start by building out a high level of requirements that outline the solutions your product will be solving which aren't currently solved in the market with the existing products available - no need to write out all the things already being done right now. Then create mockups or use a simple prototyping iOS/Android App which uses images to appear as though its an interactive app to display those critical requirements you will be building.

Get in front of the customer with your solution and start engaging in finding out what the pricing and exact refinements to those requirements/solutions would be and work to get commitment entering into an engagement with those first customers that's at a discount of what the future price will be (as they are technically funding your development). Its critical not to overthink those solutions in the beginning as finding out what the customer wants and is willing to pay for is the most important piece here but to have that convo you first need a starting point to present your new solution to them.

One other note, don't oversell make sure you have the talent in house already that can deliver the solution you are offering. If someone decides to go on a long shot and enter into an agreement before the product is complete it's critical you follow through on everything you offered.

We were able to close a national retail chain on a custom Point of Sale mobile based SaaS by following the steps above, let me know if you would like more details.

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