10 Things I Learned on Dragon’s Den

In May of 2024, my business partner and brother-in-law Paul and I pitched the Dragons.

 

In the countless times since that day when I’ve been asked, “What was that like?” the single word I’ve used over and over again has been “formative”.

 

It's partly a political answer; not wanting to spoil the results of the pitch, but it’s also a true answer. It has shaped who I am, the way I see things. It has altered and solidified various thought patterns, beliefs and behaviours.

“And what might those be?” you ask. Here’s 10 things that I learned while pitching the Dragon’s in their Den.

 

1. Swing For The Fences

There was a question, early on, “should we do this?” We didn’t have to pitch. We didn’t have to apply. We didn’t have to entertain the thought. And we certainly didn’t have to add the enormous cost and mental attention of preparing to be in the Den while also trying to run two businesses.

 

But there was something in me that really wanted to do it. Mostly gut feel here, not a ton of strategic thinking. After all, this is a bold play for a company with minimal profits in an industry that isn’t exactly known for huge investor returns.

So when I said to Paul, “I’m going to audition again (after failing a few years prior) I was surprised when he was cool with it.

 

So we auditioned.

 

2. Be Yourself (But… Actually)

Speaking of auditioning, we did it much differently the second time around. The first audition we over-prepared for. It was too scripted, not fluid, and I’m sure it showed. 

 

Our nerves were high.

 

The second time I simply spoke to the camera as if I was showing a friend around our business and I let the natural passion I have for it come forward.

 

No manufacturing. No trying to impress. Just passion and honesty and positivity.

 

And it worked. We got the green light and we were PUMPED!

 

3. Make A Plan

I’m not a big planner, but even I knew we needed a gameplan going in to the Den. The process of creating that gameplan was one of the most rewarding parts of the entire experience.

 

It forced us to dream big. If you’re going to ask for a lot of money, you better have a solid plan of what you’re going to do with that money.

 

And as we made plans, it caused us to imagine a future we really wanted. And of course, “Dragon Money” would help us get there, but even in these early planning days, the scrappy DIY side of us started to realize, “Hey, that’s a good plan. And we can action a lot of that ourselves…”

 

Formulating a plan in preparation for Dragon’s Den has helped shape the trajectory of our small business in big ways.

 

4. You Can’t Prepare for Everything

We wanted to excel in the Den, so we memorized figures, spoke to experts, and tried our best to sound legit. We really dug into the finer points of the pitch, especially the first 60 second bit (which producers want you to nail) and I would say we crushed it.

 

But once you’re “live” in front of the Dragons there is quite a bit of back and forth. It’s chaotic. They’re all talking over each other trying to get their question heard. And you have to pick one to respond to. We found their willingness to explore topics in any sort of depth extremely limited.

And the topics they brought up, as well as their responses to some of our perceived strengths, caught us off guard.

 

I’m not sure we could have been prepared for all of that.

 

5. It’s Okay to Get Whacked

I’m not a dispassionate person. I don’t easily separate myself from my work. I pour my heart and soul, my dreams (literal and figurative) into the projects I create. I use my hobbies and spare time and extracurricular interests to inform the things I create.

 

So when you put 8 years of your life on a platter for someone else to disregard, I’ve come to the conclusion that it’s okay to say, “that was hard”. 

 

I enjoy a good superhero tale, and they get punched all the time. That’s because they’re doing something worthwhile. And there’s opposition to that. When you swing for the fences, you’re going to miss sometimes. Maybe lots of times. But the world is constantly being re-made by those who try.

 

“Not getting whacked” isn’t a business plan. “Doing something great” interests me far more.

But what happens when you do get knocked down?

6. Get Back Up

If you ask my family, they’ll tell you, I took it pretty hard. We were in Ontario staying with my folks and I felt absolutely miserable. I needed to unpack what I had just experienced. A big pile of thoughts and words and evaluations just got dumped like a ton of bricks.

Thus began the process of sorting through the rubble.

And I did. 

I got “back up” and began to examine and reflect and unpack and process. Some of this was internal, but some of it was conversational. Speaking with people who really know me and not just a spreadsheet.

This was a long and healing process (that arguably is still happening).

And I’m happy to say that although one Dragon advised us to “quit” we indeed have not. In fact, quite the opposite.

7. God Has a Sense of Humour

Here’s a fun fact: As you’ll see on TV, we asked the Dragon’s for $100,000. Before 2024 was out, we received more than that from an alternative source and didn’t have to give up a percentage of ownership for it.

Ironic, no? I can see God just giggling to himself, “if they only knew what was coming.” 

And isn’t that always the case? Our momentary trials are just that… momentary!

The selling of Mobile Escape has both been a financial windfall as well as a freeing opportunity to focus. 

Which leads me to my next point…

8. Focus

This is a fundamental piece of advice that I’m taking out of my experience in the Den. One of the Dragons said, “You’re not focused.” I’m not sure this person had all the necessary information to come to that conclusion accurately, but the fact is, they were right.

 

We were trying to run two businesses and not giving either of them the attention deserved.

 

Since winding down and selling Mobile Escape, my eyes have been opened to the enormous amount of work it is to run one company well. With Escape Mail, we’re trying to play at the same level as the best in the world. We’re designing products from scratch that many people can’t even conceptualize while dealing with global logistics and fierce online competition.

 

Small business is not for the faint of heart.

 

And that’s one business.

 

Maybe one day I’ll be able to run two businesses at once, but for now, it’s time to focus.

 

9. Know Your “Why?”

Since Day 1, Mobile Escape and Escape Mail have existed to “awaken wonder”. The Dragons? I don’t think they have a tagline, but if they did it might be “Get a financial return”. Which is fine. That’s their thing. But it’s not our primary thing.

 

And something I’ve come to recognize since being in the Den is that I need to hold on to my reason for being and protect that at all costs.

 

Knowing why you do what you do is so incredibly valuable.

 

I love SImon Sinek’s stuff and he popularized this “start with why” notion. I’ll never forget how that shaped me early in my career and it still does to this day. I’m thankful to be in business with someone who shares similar “Whys” to me. Paul and I love being close to home, to our crazy beautiful kids, in the neighborhood we’ve grown to appreciate so much.

In my MBA program I was taught that a business making money is like a person paying rent. People have to pay rent to live, but you and I don’t exist to pay rent. Business should be the same.

 

10. Open Yourself to the Grace of Time

If you’ve read this far, you can handle a bit of philosophy. 

There’s a false notion that if you haven’t “arrived” today, you never will. That just simply isn’t true.

We exist in time, and we are carried down the river, and we evolve and change. Every experience makes us who we are, and if we let it, I believe it has the power to change us. The way in which we are changed is up to us.

 

There’s a graciousness that comes with time. Knowing that you can fail now, and try again later. Knowing that failure is never the end of the road but the start of something.

 

It’s incredibly ironic to me (once again, God has a sense of humour) that during this Dragon’s Den escapade I’ve been immersed in the story of Ernest Shackleton. If you’re not familiar, his story is one of incredible survival and overcoming of odds. But it was also a colossal failure at face value. He never reached his goal of crossing the continent. Not even close. Yet the world is okay with that. Because we all fail. But it is HOW Shackleton failed that has him enshrined in the halls of heroism. It was the way that he rose to the challenge, left no man behind, and persisted through every kind of adversity.

And so I leave you with these 10 Dragon’s Den reflections and say, thank you for reaching! If you want to know more about Shackleton, head on over and order the Series we’re just finishing. You can also check out our socials for more updates about the business sale and the new focus on Escape Mail.

 

Thanks for reading and being part of this journey with me.

 

Bye for now!

• Eric

Co-founder of The Escape Mail