Thanks for being here and taking a sip from the Fountain.

This week, we're diving into the art of crafting a compelling pitch, essential for any founder navigating conversations with investors, customers, or teams. I'll share personal insights I've honed through years of experience, ups, downs, and jewels learned along the way, along with a killer conversation with one of the brilliant minds behind Dragons’ Den.

⏳️ Estimated Read Time: 8 minutes

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FOUNDER LESSONS

I want to share some insights that have shaped how I pitch and communicate ideas. Whether it was speaking with investors, customers, or my own team, these guidelines helped my approach and were framed through years of peaks and valleys.

Just like stepping onto the basketball court, getting on stage, or preparing to go into the operating room as a doctor you need to be ready for your moment. Take that critical time before your pitch to mentally prepare. The next 4-5 minutes could be the most important of the company’s history.

Confidence (and success) begins with consistent preparation.

Make people feel the problem. Transport them directly into the scenario:

Clearly framing the problem helps your audience feel the need for a solution with genuine empathy and understanding. It’s also important to have a frame for your target demographic or potential investors that aren’t necessarily customers.

Your solution needs to stand apart:

Steve Jobs famously said, "connect the dots looking backward." Your past experiences, skills, and passions creates your special sauce. Draw from them authentically. You don’t have to have 25+ years of experience in the textiles to be the right person for the job. I had zero. (Watch for a future Fountain dedicated to Your Special Sauce!)

Economics matter. Investors trust founders who deeply understand their numbers. Know the implications of the investment you are or are not seeking. Clearly communicate when and how you'll break even. Understand your key ratios, and why they aren’t where they should be.

You need to be the person that has the best understanding of these numbers.

Master your elevator pitch by developing multiple versions:

Yes have a 1 second pitch. Mine was “Have you heard of Saxx?” My 30 second pitch got into the problem, and then my 30 minute pitch had a slide deck, financials, and everything that I needed to paint an entire picture.

Practice delivering your message quickly and clearly. It’s not impossible, you just need to practice and refine.

Think of explaining your favorite book or show—concise, clear, and passionate.

Make the logistics of someone joining your journey straightforward.

You’re going to need at least 10 different pitches. One for investors, one for customers, one for talent you’re trying to convince to join your team, and so much more that can be industry specific. Be ready to tailor the message to the audience.

Stack your unique experiences and talents—they make you irreplaceable. My own special sauce came from confidently and humorously discussing sensitive topics like your balls sticking to your leg. People didn’t want to talk about it, my ability to made me unique. Embrace what sets you apart.

Entrepreneur: Tara Bosch. An amazing entrepreneur.

Ask: 100k for 10%. Didn’t get investment (Dragons’ have to be kicking themselves for this one) Loss Porn for all the Dragons.

Entrepreneurs: Brian & Corin Mullins

Ask: 120K for 20%. They got what they asked for.

I’ve given a lot of pitches in my life. No matter where I was pitching, one thing always held true: you don’t just sell a product, you sell the problem, the story, and the opportunity.

Recently, I caught up with Molly, a senior producer at Dragons’ Den, someone who’s spent nearly two decades watching founders walk into the Den and was my producer when I went through in 2007. We went back and forth, and with pencil in hand I got a bunch of great jewels from her.

I was already a fan of Dragons’ Den from season 1 when I got invited to audition from someone that saw me compete at a pitch competition. At this point, it was still technically a school project and had done a few thousand in sales.

There's a moment before you go pitch where, as an entrepreneur, you have to obviously hope the preparation that you've done to that date will prepare you for any of the questions you're going to get in the den, because I knew it would be a tough environment. But at the same time, you have to take the ball and know that's your time.

I was asking for 250k for 10% and couldn’t get a deal done with Arlene Dickenson, but after the fact, she made key introductions for me and I ended up winning the Armchair Dragon Award, for the best pitch that didn’t get a deal which came with $50k. Even though I didn’t get a deal the Den gave me so much, including these lessons with Molly almost 20 years later.

I also got to pitch to Laurence Lewin, the founder of La Senza. He was actually the key to my pitch going well because in his beautiful British accent described my prototype as “a well performing garment”. Once he gave the nod of approval the other Dragons were more into Saxx.

If you can’t say what your business is in one sentence, you’ve already lost.

Open yourself up for more questions.

Entrepreneurs get so deep into their own business that they assume people care as much as they do. They don’t, not until you make them care.

We then talked about after that initial elevator pitch you need to have a proper business pitch.

Although my “you got your nuts stuck to your leg when you're fishing” sentence was a little absurd I had proper business plan to back it up once you get through the first door.

Molly emphasized that public speaking can be challenging for some, but the more you practice your pitch, the more confident and effective you'll become.

Before I went into the Den, I was lucky enough to have a ton of pitching experience and feedback from the Canadian Angel Network under my belt.

Doing it in front of the mirror is one thing, but getting in front of people, audiences, or competitions helps you get those reps in.

I was probably most nervous about knowing my numbers. I saw people get grilled, and it was very emphasized so that’s what I was ultimately the most worried about.

I asked Molly how entrepreneurs coming up should position their ask. She said:

Molly explained that another key ingredient to great pitches and businesses, is knowing what you don't know and then bringing in people who can help with that.

Some people isolate themselves in the innovation. They're just so dead set on perfecting something and not being able to admit what they don't know and where they need help.

That's something that that people don't consider, is that you have an idea, but it's going to take other people's ideas and thoughts and skills to be able to execute that.

A lot of pitching comes with a lot of feedback. I personally weigh heavily people who have done it before. Absorb all the information, but stick to your guns and filter it with your business and direction. I also like to get arm’s length experts to weigh in on the advice, and the answer can oftentimes lie in the disagreements.

Thanks to Molly for having that conversation, reminiscing about the pitch, and giving invaluable insights to The Fountain.

This is a great time to audition for Dragons’ Den. Canada has a proud sentiment about us right now, and I encourage everyone to audition.

Molly explained that sometimes people are worried about going on and getting their idea stolen. But as Naval Ravikant says please steal my idea, executing is brutally hard, don’t be worried about sharing.

Applications are open for Season 20. So give it a shot - changed my life.

DD will be hosting in-person auditions across the country. Here is a list of cities and dates.

We can’t wait to see the incredible innovation and great ideas our Canadian entrepreneurs have to present! Here are some tips for a successful audition.

You can apply here!