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Serving Mid-Market Businesses

Serving Mid-Market Businesses

This is a summary post about what I learned from 100 conversations with owners/CEO’s of mid-size businesses.

Here’s the structure of this post:

  • Background on why I did this

  • Defining a midsize company

  • Who are the people I spoke with

  • Common challenges during transition (from small to mid size)

  • Common challenges at midsize

  • Tips to their younger selves

So let’s get started!

Why did I do this?

Around 2015, it started to become apparent to me that there is abundant resources/expertise available for large global enterprise companies and small local/hobby businesses. They are thus very well served for nearly all of their business needs by available in-house talent and professional services. But what about those companies in between? Those mid-size/mid-market companies you her about? How does one journey from being small business to becoming a global enterprise?

This question niggled at me for a long time, until finally in the spring of 2016 when I couldn’t take it anymore. Folks I’ve mentored will smirk at this next bit. Yes, I followed my own advice that I’ve given to every one of you that you’re tired of hearing: I hustled to arrange 100 deliberate conversations with people who understand this better than me and I learned from them.

Thus, I set out to learn more about the challenges of companies in this growth/transition phase. Maybe I would discover there’s already a solid solution available on the market (spoiler: there wasn’t) or gather enough insight to be able to propose a solution for this market segment.

But before we move on…

What’s a mid-size company?

Here we know there’s this glaring gap in available resources/expertise to serve the segment of mid-size / mid-market companies, but what exactly are they?

Blog Refresh - Jan 2019

It’s been three years since I put this Blog into the public sphere. A lot has happened.

Here’s how I’m currently thinking of my relationship with the content published here.:

  • Categories - the types of content on this

  • Tags - short descriptions about the quality of content, so I can revisit it at a later date

Categories

Health & Wellness 2019

Health & Wellness 2019

Through this post, I want to:

  • Stay accountable to improving my Holistic Fitness pillar (currently my #1 investment area) by publicizing my efforts

  • Analyze the state of my Holistic Fitness: where it currently is, what got it here, why it is as it is, and how to hack it better

  • Document a progression so I can revisit this in the future if/when relevant

This (now very public) post is an exceedingly scary thing for me.

It pains me to so openly admit what I perceive to be a weakness and character flaw (working on this), but this is important and I’m committed to being better…

Bookmarks Clearing 2018

Bookmarks Clearing 2018

Note for any readers: this is written to myself for future reference.

While going through the exercise of year-end cleaning, the process includes checking bookmarks for what will be highly relevant going forward. These are a few I’ve kept throughout 2018, which are now lower priority but which I may like to reference again in the future.

Frameworks and Tools:

Dec 2018 - What is Joshua reading?

Dec 2018 - What is Joshua reading?

Having recently attended a number of events this autumn to speak with university students, young professionals, and small business owners, I’ve fielded many questions about what reading I would recommend to them.

While I’ve previously shared my thoughts on this topic, my journey has taken me down many paths and through many hoops in the three years since then. I have a few more thoughts to share.

The big one is that everybody should learn Sales. > Cue groans <

Listen, I get it: ‘selling’ is thought of as something dirty… but that’s such an outdated notion. The reality is that we are all selling, all of the time. Selling is the art and science of…

DEF CON 26 - My Thoughts and Reflections

DEF CON 26 - My Thoughts and Reflections

I was recently in Las Vegas for DEF CON, the world's largest Hacking Conference (Site, Wikipedia). For four days, 20,000+ nerds descended upon Vegas and put security professionals on edge. It was my first time participating in DEF CON, and it won't be my last.

Over the course of my week in Las Vegas, I caught up with old friends, met new people, learned about the Hacker world, was exposed to novel ideas, had fascinating and thoughtful discussions, lived it up Vegas-style, explored the famous city's culture, and ate too much unhealthy food (*cough* Typical West Coast).

I've been left with a lot to ponder since coming home from DEF CON…

Worthwhile Pursuits

Worthwhile Pursuits

As I've been pushing hard on pursuing new opportunities lately and working through a handful of challenging projects, I've been pondering the question, "What is truly worth striving for?" in considering how to allocate my limited resources of time and energy.

This is the list of things I keep circling back to:

  • Excellence

  • Integrity…

On the topic of direction.. as a young person

On the topic of direction.. as a young person

This is a Shitty First Draft post that I never got around to completing. Coming back to it now cause I've been having mentoring calls every week for a while now. Same things KEEP coming up. So, here I am, writing a post about it so I can point to it.

1. Brain Dump about Expectations + Learning

Are you doing what you do to meet your personal expectations, or the expectations of your parents/society/tribe? It's your life, dude. Live it as you see fit.

It's great to be excited ("passionate") about a particular industry, but how much do you really know about it? I hear far too many people who were sold on the 'sexy' of a particular field of work, where the majority of their understanding came from marketing efforts by industry associations or people who've themselves been sold on an idea…

Universal Checklist for Presentation Delivery Prep

Universal Checklist for Presentation Delivery Prep

Ever since I went to university, I've been thinking about writing more in a public manner. Finally pulled the trigger in 2016 after years of deliberating. Here's a post I found that I'd written an entire draft for back in August of 2013.

I enjoyed reading this because it offered me an interesting look into how I've developed concepts and workflows since then. Sharing this in all of its original glory because it's rather funny and still pretty relevant!

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This post is an ongoing attempt to create a universal checklist for the preparation of presentations. Note that I am assuming that the presentation deck and demo product are already complete after considering objective, available time, time of day, audience, and so on. This checklist is a combination of actions and reminders with some definitions included after the checklist...