My Story

My name is Andrew and this is my blog!

I started this to share my love for starting businesses, investments and career advice. I’ve been going on for the past 15 years. I’ve always gone all in once I’ve decided it’s something for me.

I’ve decided to go all in on helping people figure out how to start a business and what they need to do to succeed. This blog will help you figure out how to do just that and everything to help you run your business too.

I’ve also been exploring alternative investments through crypto, real estate / Qualified Opportunity Zones and some fun adventures through exploring space and precious metals (gold and silver).

This blog is bringing together my competitive nature and knowledge around starting businesses, B2B SaaS software and investments. I feel that you must have a healthy mind and body if you’re going to be competitive and win in your professional life so here it goes!

Here’s how it all started

I believe my passion for sales and competition really stems back to a challenge I was given by a family relative. Hey ‘Andy’ (that’s what I was called as a kiddo) – I’ll give you $20 bucks if you can get all the rings on that dolphin’s nose. It was one of those toys where you have water and a button that moves the rings around. It was a challenge I’ll never forget because I stayed up for hours trying to solve that crazy puzzle.

Since then, I continued to be competitive but I was always trying to find the next thing to be competitive in. Whether it was sports, making the most phone calls and being at the top of the dashboard or getting that last prospect to commit to a meeting.

Let’s back up and really get into it.

Here’s my story – I hope it really helps you understand who I really am:

The 80’s – Born into a west coast family of fun

We lived in a blue house and my very first vivid memory I remember is one that my family won’t forget. I was hiding in the house and everyone was looking for me. I thought it was funny at first but it really scared the begezzes out of my parents. Where is ‘Andy’? At the moment I thought it was funny but it wasn’t to anyone else.

I was the first born and always caused problems for the parents. I never wanted help with anything and thought I could do everything by myself. Maybe that’s why this blog exists. I wanted to always do it on my own without help from an early age and until now – where at the time of writing this – I’m about to turn 40 (June 2022).

1992/1993 – We moved out of California and up to Oregon

I can’t recall the specific age but I will come back and update this later when I get the specific age but we moved to Oregon when I was in 6th grade. I specifically remember the drive up in our blue Toyota Corolla which happened to be my first real car which is another story for another time. My dad got a new job in Portland and we all moved up to a new state with a new big adventure for all of us. It was a scary time for a 10-11 year old kid moving up to a new state and starting at a new school in sixth grade – the first year of middle school.

Trying to fit into a new school was hard at first but over time I went through it. It was hard enough having to move but a new school was also challenging at this time in my life.

I am grateful for the move up to Oregon and the life that transpired after continues to allow me to thrive but in the moment it was a challenging time.

The middle years were full of fun and challenges but they formed me for who I am today. Whether it was golfing, hiking or hanging out in the Portland rain – it was a fun time.

The 2000s – Graduating High School & Growing up

One thing I always remember was having the tag line of the ‘Smoke Free Class of 2000’. I recall it being a logo something like Smokey the Bear which was ironic considering we are the Smoke Free Class of 2000!

When you graduate high school the first thought I had was getting to college. I thought I knew exactly what I wanted to do. I wanted to be an electrical engineer and build bridges… That was what I thought I wanted to do so I headed down to Oregon State University. During that first year, it became very apparent to me – that was not my calling. I almost ended up in ROTC because I was always primed and ready to go in the morning for a good workout – and you got some college credits for going early AM for a workout I was doing anyway.

I really wasn’t sure what I wanted to do so I took the summer and started working at this company called Spot Security. At the time I didn’t realize how much that first job really formed me into what I’m doing today. I was given a phone book and phone numbers to call – to set appointments for outside sales reps to go and sell home security systems.

At the time I thought it was the best thing in the world. Looking back, it reminds me of that episode of The Office where Michael Scott has two jobs. Where he’s making calls in the evenings after his day job. That was me but without the first job.

Fast forward a few years and I am at University of Oregon (SKO DUX!) and decided to go down the path of getting a degree in Economics and a minor in Business. It would have flip flopped with a Major in Business but I would have needed to stick around for an additional year for the right credits.

It was time to move on to the next chapter….

2004 – Graduating and that first real job after you graduate

Yep – it’s true. I graduated and found a job working at a company called ChannelForce. Our job was to train retail associates how to sell manufactured products like Nikon cameras, TiVos and Adobe products at Circuit City, Good Guys and Best Buy. We would make sure they were trained correctly, the stores had the products in the right location and we’d report back to the brands we supported. Imagine having reps around the country be responsible for going to do store visits and take pictures of the end caps. My job was to compile it and make sure it was put together in a clean way so we could report back on a monthly basis.

From there, I moved into supporting SanDisk where I was a territory developer across the west coast. This meant that I was responsible for finding all the T-Mobile, Sprint/Nextel, Verizon and AT&T stores and training the retail reps on why it was so important to have a mobile memory card in a phone – pictures!

Throughout this job, I learned how to find and build relationships with people to make sure I was doing my best to build what I had set out to do.

This was my first job and it was in Oregon. I was fearful of leaving Portland and finding a new route. Fear can always hold you back and that’s what was happening to me. I was fearful of change; fearful of failing and was comfortable in my ways.

2006 – Time for a change

I didn’t know it at the time but I moved down to San Francisco after I realized it was time for a change. I loved sales and I loved being around like minded people. I’ve always had this love for networking and bringing people together.

I took my first Inside Sales tech job at Palm. Yes – the first real smartphone before the iPhone was cool. Palm and Treo were the first kids on the block and I loved it! I’ll get into why another time in more detail.

I spent a year getting comfortable in the Bay Area and found myself wanting more and found my way to I still remember the moment in time where I realized I was entering B2B SaaS Sales. I found my true calling when I jumped in.

2008 – The beginning of my B2B SaaS transformation wasn’t just a calling for me but it was the beginning of my fitness journey too. I was 26 and entering I will have to come back to this another time but my love in college for ROTC and the pain of getting up early in the morning – always kept my competitive nature thriving. I loved waking up and getting a workout in. This translated to 5am calls to the East coast from San Francisco and was crushing the sales dashboard before anyone else showed up at 8-9am Pacific. I was on fire and loved it.

During this time I really learned the best home gym was at the time. I started jumping into P90X with our favorite person – Tony Horton! If you don’t know Tony – you should check out P90X. It was a new thing back then but now we have sooo many variations of his extreme workouts.

This also led me down the path and love for figuring out different diets and nutritional habits. I was working so much and I was trying to stay fit and healthy at the same time. It didn’t help we had a ‘happy hour’ every day with the other 26 year olds trying to figure out their life.

This experience of getting more involved with fitness helped me stay focused on exceeding expectations at this job and it led me to an Account Executive role where I was helping organizations figure out their accounts. I was driving down from San Francisco to San Mateo and loved it. I will never forget the times of fun in that San Mateo office.

Starting around the summer of 2011 (the time when I should have purchased Bitcoin), I was beginning to lose deals to Zendesk. Zendesk is a customer support software and I was trying to sell our Service Cloud offering to small businesses. My customers were telling me Zendesk was just easier to use and a much lower cost. I checked it out and a few months later – I was working there.

Zendesk became one of the best decisions I made. I met some amazing people and went through a few roles that gave me the DNA and ammo to be extremely dangerous in my pipeline generation journey. We became one of Salesloft’s first clients of their Prospector tool before we moved into Cadences.

I also pulled in skills for:

  1. Building Sales Development Teams
  2. Creating the tech stack to scale from 100-1000 employees
  3. Building the sales enablement and training muscle to make sure we optimized who and what we already had.

It was a really fun time.

After the Zendesk IPO and the adventure of being on that rocketship, I wanted to find a new adventure and that’s when Mr. Pipeline was born.

I got a call to come join this small company based out of Ann Arbor, MI called Duo Security.

My mission if I were to choose to accept it would be to help solve two things:

  1. Determine how much pipeline was needed to hit revenue targets
  2. Build the programs to make up the gap

Seems simple when you read those lines but simple isn’t necessarily easy.

It’s similar to building muscle. It’s simple – not easy. Eat more of the right stuff and give your muscles a reason to grow by pushing them to the max. We’ll get to that part a bit later.

2015 – Mr. Pipeline (aka Doctor Pipeline) is born

Joining Duo Security and living out West was challenging but who doesn’t love a good challenge. I was able to help manage a team remotely and actually login to a robot that I could spin around and talk to people in a ‘pit’ of desks remotely from 5am PT. It was a change but a good one.

This was also the time when I started Shawn T.’s Insanity Workouts because I was just that insane. I loved my extreme workouts and I started my crazy workouts here. Intermittent fasting has picked up steam recently but I started this back in 2015 trying to figure out how to hack my way to 165lbs and 9% bodyfat. For the record, I’m still trying to crack that code but I have a lot of adventures and stories for you we’ll be talking about throughout this blog.

I spent almost six years at Duo Security and was able to really learn more about myself during this six year period than any other. Many life changes happened during this time. I may come back and edit this another time and add more personal stories but for now – just know that life changes quickly and you need to live in the present. Take it one day at a time and focus on living your best life.

If you want to know more about who or what the Mr. Pipeline role is just click on over and see what I’m sharing. It’s simple – not easy. Building a team is not easy and doing it remotely is even harder. I was doing it before we were all forced to by a global pandemic.

Everyone should have a role that’s dedicated to sales to helping your organization focus on building pipeline. Without that you’ll end the quarter and if the team missed the revenue target – typically you’ll start pointing fingers. Avoid that by giving it to someone who can help you figure out what to do and where to go.

2022 – Today & This Blog –> Starting your business

This blog is an extension of me and I’ve started my own business. This blog is it’s own business and I’m here to share everything I’ve learned on how to start your own business. As you go through your journey, I’d love to hear more about what you’re doing and what you need.

There will be plenty more to talk about and I’ll always come back to this story page and update as there is more to share.

If you made it this far I really appreciate you landing here and learning my story.

Thank you for reading.

I hope this story brings you some motivation, happiness and joy.


Andrew McGuire