This next chapter is titled “Rise” – so how do I start this? The idea behind the next three chapters is to walk you through the last five years of my life. Pretty cool, right? Chapter 5 = The Last 5 Years. Ok! High-Five! Let’s do this. 

The last five years of my life have definitely been some of the most challenging years. Some of the most? No! Definitely the most challenging years of my life to date. So let me unpack this and try to help some of you see some significant road markers, or as we like to call it in the business investor community – Red Flags! You MUST pay close attention to the Red Flags, or you will get Fucked! Period. This is why these next three chapters are in the following order: Rise, Fuckup, and Comeback. These chapters will reveal the Red Flags all along the way. My hope for you is that you will take notes on these experiences – specifically the Red Flags, and you won’t make the same mistakes. 

I was at a startup event last year, and one of the founders was speaking at a Founder Fuckup session. I literally laughed out loud (LOL) when I saw the sign on the outside of the conference room. I saw this on the speaker’s schedule, but until I walked up to the door and saw the sign on the wall, it never actually hit me. I was celebrating inside because I knew this was going to be Real Talk. As an entrepreneur, – we crave these conversations so much. It confirms we aren’t alone in our crazy stories. 

So there was this one Founder and CEO of a “now” very successful company. This wasn’t always the case. There was a time where he had failed and failed miserably to the tune of over 450 million dollars. His company was fined millions of dollars for business practices that were called into question. So what would you have done? Most would have curled up in a ball and said: “I am done!”. No. Not this entrepreneur. He got back up off his ass and became a Billionaire within three years of taking that hit. I love his story! When you get up close and personal with these crazy Founder Fuckup stories, you don’t feel as bad with your storm report. Most entrepreneurs, especially Founders, have crazy stories. Stories that, when told, can save other entrepreneurs from much much pain. So pay attention to these stories. These are very expensive lessons. In my case – it cost me millions.

So let’s rewind back to 2014, specifically around the fall of 2014. My wife Amy had just finished battling Kidney Disease. It was during my initial startup that my wife had been getting quite ill. She had some crazy, unusual symptoms, and none of the Doctors we had taken her to could figure it out. She has quite a complicated medical history to start as she has Epilepsy and also Lupus. So this was one other fight that she just didn’t need, but God had different plans. 

So during her Kidney Disease treatments, Amy had become allergic to the chemo-hybrid medication she was on. It was literally killing her. She was “that one” out of hundreds of cases where this treatment was successful, but her body was rejecting it. Her blood cell counts started to dive and dive quickly. I wasn’t sure she was going to make it through. It was the scariest time of our life together. So the long story short – it took a team of Doctors at the Foothills Hospital in Calgary, Alberta, Canada to figure this thing out. They stopped treatment and pulled back on all her meds to see if they could get the blood cell counts to rise. They did. It worked! It took a while, but she eventually stabilized. She wasn’t out of the woods yet – but we were making progress.

So during this crazy time in our life – I end up talking to one of my investors who happens to be in BC (“British Columbia, Canada”). I discussed the possibility of moving to the Vancouver area and opening an office there and launching a Beta Pilot. I had been working on trying to get my startup off the ground for almost two years leading up to this point. We needed to raise some bigger money and get a focused pilot going for this project. My big idea, going back to 2012, was building a social commerce platform where we could create the ultimate loyalty program for product brands in the world. This would lead me to invent shoppable tags with my app. A tag that would literally appear on an image, and you could touch the tag and purchase the product in the photo. There was a lot to the platform and our product. I won’t go into detail about that now and how it actually worked – but it was a crazy cool story of new technology and how there are really no limits when it comes to our imagination. 

So back to this investor in BC. He expressed a lot of interest in increasing his current investment commitment to a much larger number and helping to get us up and running with our Vancouver operations. So I jumped and jumped quickly! Amy was barely out of the hospital, and I was loading her into our Audi A7 and heading to Vancouver to look at houses and office space for rent. At this point, we had no money. Startup life is lean. Very, very lean. So we would have to live outside of Vancouver in the suburbs and then have our office closer to downtown. So we ended up finding a place in Maple Ridge, BC. It was a nice two-story home in 

a quiet family community. This would be great for the girls. So we headed back to Calgary, and I rented the moving truck and went to get our stuff packed and loaded up for our move to BC.

It was just a few days later, and we were back in Maple Ridge, moving into our new home. Amy was still in Calgary as she wasn’t doing very well with her Lupus and Kidney Disease. So now we had to get her a referral to a Kidney Doctor in Vancouver and try to get her out there once she was stable. We were very blessed as she was referred to the top Kidney Doctor in Vancouver. He was the lead Doctor behind the Kidney program in Vancouver and was promoting a new drug that was on the market. He was convinced based on all the medical data he had on Amy that this would be amazing for her. He discussed this treatment option with her Doctor back in Calgary, and they both agreed this would be a good option for her. So she went on it, and within just a few weeks, she was in remission with her Kidney Disease. To this day, she is still on that drug, and her labs are normal every checkup. It has been a real blessing for her.

So we had barely unpacked the boxes, and I was heading over to the island to meet this investor in Victoria. I only had about $200 left in the bank. So everything was on the line. I got into my car and drove to the Ferry terminal. It was approximately $80 to get on the Ferry with my car one way. That means after getting back home, I would now be down to $40 in the bank. So I drove off the Ferry and headed over to my investor’s office. He was busy dealing with staff, so I had to wait a few minutes to get into his office, but then the moment came. This was it! I had to make this happen for my family. So I went into the updates – showed him where I was at with everything, and went through the plan for moving forward with the office and pilot in Vancouver. I asked him for his new commitment amount. Then the words you can’t afford to hear end up coming out of his mouth – something like this. “My family and I recently made some large investments and acquired a couple of businesses out east, in Ontario. I have put all my money into these investments. We have also had some complications with one of the properties, and it’s going to cost us even more money now. So now I am trying to find the money for that. I’m sorry, Jeremy, but I just can’t do anything for you right now. Maybe in the new year, but right now, I’m tapped”.

*Mind Talk: 

Fuuuck! Whaaat??? Is this really happening right now? My mind is about to explode! I am going to be down to $40 when I get home tonight. My mind is racing. What am I going to do? What am I going to say to Amy when I get home? This makes no sense.

My mind was right. This was making no sense. I was making no sense. This was stupid. This was the worst play of my life. So there I was – looking into his eyes wondering what to say next. I mean, what do you say? He just said no, I’m tapped. So then I made the decision to go full exposure. I was literally about to show all my cards. I told him I was down to my last $200 as of this morning. With the Ferry ride over here and then back – I will be down to $40. Is there anything you can do? Any ideas you have? I need help. I am out of options. He looked shocked. It was hard for him to believe that I was this low. So he offered me $1,000. At that moment, it felt like One Million Dollars. So he gave me the money, and I headed home.

I can still remember the feeling as I pulled up to the Ferry terminal to go back to Vancouver. I felt so sick. I had nothing here for me. Nothing! Why the hell did I just move my whole family to BC? I mean, there was no next move. No play. Not even a well, let me get a couple of investors together, and we will figure this out Jer. No. Nothing. So I drove onto the Ferry and headed up to the restaurant to get something to eat. I guess I could afford a cheeseburger. Well, not really – but the thought of some comfort food at that moment was good. I remember sitting at the table and eating, looking out the windows at the beautiful ocean, and thinking I have no plan. This is an absolute mess. After eating, I went back down to my car and just sat there. No 

music. No audiobooks. Just the sound of the Ferry moving across the water and the humming of the engines. I had to prepare my mind for the conversation I was about to have with my wife. This was not a good update.

I got back home late that night, and Amy was resting on the sofa watching TV. I sat down with her and broke the news. She was happy I managed to get some grocery money out of the trip but definitely disappointed. The one thing my wife has been able to get good at over the years is not getting excited until the deal is done, and the money is in the bank. I wish I could be more like her that way. 

I started to panic a bit the following week and was making phone calls trying to get some other commitments closed so we could stay put. The timing wasn’t right. I was getting all No’s. I started to hustle some of my web design and consulting business to close some deals, but nothing was happening. This wasn’t good. I was on the phone one evening with my Mom back in Alberta and was telling her everything that had happened. I told her I just didn’t know what I was going to do. I was starting to feel really down and what was starting to be my first experience of being depressed. I began to focus only on the problems. In my mind, at this point, there were no solutions. I was starting to become a victim in my mind. It was a terrible mindset. I started laying around a lot, sleeping throughout the day, and I had a hernia problem from all the heavy lifting the past couple of weeks with the moving. I could barely walk. At one point, the pain was so bad, Amy had to carry me to the restroom physically. It was crazy painful. A couple of days later, my Mom called me back and suggested we move back to Alberta. I told her that it was impossible as I had no money to go anywhere. I called one of my best friends and asked him if there was any way I could borrow enough money to get back to Alberta and do some work with his company while getting back on my feet. It sounded promising, but nothing confirmed. I was running out of time. There was no rent money, no money to pay any bills. 

My mom started talking to some friends at church privately about what we were going through and managed to get some money together to help us move back to Alberta. So the next day, we started packing, and the following week we moved back to Alberta into my parent’s basement. Yes, my parents’ basement. Here I was 35 years old, married with two daughters, and moving into my parent’s basement as a startup entrepreneur. How did I feel? I felt like shit! A complete failure.

We arrived at my parents on a Friday evening, and the next day they are asking us if we want to go to church with them. Do I want to go to church? Hell no! Where is God in all of this? What about the scriptures that say, “My God will supply all my needs’? Really? Church? No thanks! I was not in a good place, spiritually. I guess you could say I was spiritually dead at this point. I had no faith. Well, Sunday morning came around, and we did end up going to church. Mostly because I would feel guilty taking the help to move back to Alberta from people from this church and then not show up to share my appreciation. So we went as a family on Sunday morning to my parent’s church. This was November 2014. I remember seeing everyone smiling and looking so happy, and it made me so upset. I put my plastic smile on and just smiled right along with everyone else. 

After the church service, my Dad wanted to introduce me to a couple of his friends. The first friend he introduced me to was Robert. His name isn’t really Robert, but for the sake of his privacy in my book, and the fact that this is a very litigious man, we will call him `Robert”. So Robert asks me what I am doing for work? Great question, next question. Like, come on, man. The last thing I want to talk about at this point was my startup, but I did. I explained my idea and what I was working on and how I needed to get some work lined up. This was why I had moved back to Alberta. Robert started giving me some free friendly advice on what I could do as there was a lot of demand for this type of work in Alberta at that time. He also offered to let me use his truck if I needed to. This Robert guy seemed very friendly and was genuinely interested in helping my family and me.

Another man walked up to my Dad and I while we were standing there talking with Robert. He introduced himself as Dan. Once again, his name wasn’t really Dan, but for the sake of his privacy in this story, we will call him “Dan.” So now I have Dan asking me what I do. What kind of software are you developing? It turns out Dan is a technology geek as well. He got what I was talking about and later explained to me that the company he worked for was looking for someone like me. They had a technology company in the insurance benefits space. This sounded interesting. We exchanged numbers, and on Monday, he scheduled a lunch meeting with me. 

We met for lunch and discussed the opportunity with his company. He wanted me to meet the owner and president. So within a couple of days, I was at their office sitting with the Boss. It was a formal first interview. Tons of questions, and I started to ask myself – do I want to go down this road? This sounds a lot like a “Job.” It was a job, but a job is exactly what I needed. A job was exactly what my wife and my family needed. A job was a paycheck on the 15th and the 30th, something I wasn’t used to as an entrepreneur – especially a startup entrepreneur. So the first interview led to a second interview, which led to an official job offer. We negotiated on the terms a bit, but it was a deal. We came to terms, and I was officially starting my new job the following week. I explained my current financial situation in detail, 

and they gave me a signing bonus to start. Immediately I started to feel alive again. I remember getting into my car with that signing bonus check and driving up the driveway and feeling like a RockStar again. This was a Huge Win!!!

I came walking in the door, ran downstairs to see Amy, and threw the check on the table. Look, Babe! I got the job, and we have some money again. Now we can get our own place. So we started looking for a home we could rent, and found the perfect place that weekend. It was already vacant and available for immediate possession. We applied and got the keys the next day. We were so excited! We were going to be in our home just in time for the Christmas holiday. 

I guess I can go back a few lines and take that scripture I was referencing and confirm the fact that my God does supply all my needs. I am personalizing this verse, but at this moment, it was my truth. It was my reality. God came through BIG TIME! I was so incredibly thankful for this opportunity. I felt like a whole new man. So we moved into our new home that weekend in Sherwood Park, Alberta. Amy was so excited, she unpacked every single box that weekend, other than my boxes and the ones that were in storage. My two daughters did the same. We settled in quickly, and I was ready for the next week to start my new hustle.

The Job

So I rolled into the parking lot of the office early. Too early. There was no one there yet. I sat in my car and was listening to an audiobook and then the COO drove up. Here we go! Day one – let’s go! Let’s do this. My desk and office were all setup. I just had to move my personal things in and get settled. I was ready to hit this hard. I wanted to show them what I could do for the company in my first week. I was on a mission. I was the VP of Sales and Marketing. The first thing that needed to be dealt with was the company brand. It was weak! I later found out they paid a local agency a small fortune for re-branding them just months before I arrived. They got scammed! It was terrible. 

So I started working on some branding ideas, which included a new logo. I got a new logo and brand together right away. It came to me so quickly. I hand drew the logo icon with my design software, Adobe Illustrator CC. It was sexy. The colors I was proposing were Bold. Strong. I couldn’t wait to introduce this new brand to them. They were either going to love it or hate it. So I called a meeting with the executive team to present my ideas. I will never forget the look on their face when I presented the new logo and the branding samples. They were shocked! Minds Blown!!! This was a good first week on the job.

We made some minor adjustments to the logo and the colors, but it was a Home Run. I had the approval, and we were off to the races implementing this new brand into all their creative and corporate communication tools. They immediately started to update the website with the new colors and brand. It was Hot! It was Sexy!!! 

As I am writing this book now – I just went to their website to see how they’re using the brand. Yes, it’s live, my baby. It still looks so new and fresh, even almost five years later. I was really proud of that work, and I still am. Sitting here looking at their website right now and in one of my open tabs, you can see the logo icon in the color I created. I am not trying to brag here, but only showcase how quickly your life can change, how you can go from being so depressed and hopeless – to being on top of the world in just days, weeks. I was on top of the world. My creative juices were flowing again, and I was doing what I was good at. I was using my talents, and it made me feel like a million bucks.

The company I worked for was Ross Benefits Group. You can see the brand I created here on their current website > http://www.rossbenefits.com/

It was just a few weeks in, and I was starting to feel the entrepreneur itch coming back. The bills were getting paid – and getting paid on time. The stress was starting to disappear. It felt amazing. I started to think about my startup again. I had set up an office at home with my iMac on my desk, but I hadn’t done anything with my startup project in weeks. I will put a picture below of my home office exactly how it was when I took the app idea from just some digital wireframes, a PowerPoint presentation, and some screenshots – to a fully developed working prototype so I could start raising money again. There are many benefits to designing and building a working prototype model for a mobile app project, but the main pro is to work through what you will actually need to code and what can be road mapped into the project at a later time. This allows you to separate Needs from Wants so you can get to market quickly. 

Pay very close attention as we prepare to move into the next chapter titled “Fuckup.” You will see how fast we take my idea and prototype, fully code, and develop the technology and publish it to the app store. “It was nothing short of a miracle,” as one of our investors put it days before our official launch.

So are you ready for some more of the “Rise” story? I could keep writing into this chapter, but it’s getting pretty long. I don’t like books that have L-O-O-O-N-G chapters, so we will save some rise content for the next chapter. Since the Red Flags are so important for this book and to my startup story, I am going to do a Red Flag Review Checklist at the bottom of each chapter so you can use this as a reference point. So here is your first Red Flag Review Checklist below.

Red Flag (“RF”) Review Checklist: RISE

RF1: A deal with an investor (current or potential investor(s)), is not a deal until all details of the deal have been negotiated, all legal documentation has been signed, and the money is in the bank and available – literally showing up as “Available Funds” or “Available Balance.”

RF2: DO NOT move your family to another State/Province, or drag them across another country until the money is in the bank. Once again – literally showing up as “Available Funds” or “Available Balance.”

RF3: Don’t blame God for your mess. Period.

RF4: Manage the itch. When the Entrepreneur itch comes back – remember not to put your family at risk. Don’t quit your job too early. Keep your personal stress to an absolute minimum and under management, or you will burn out quickly.