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

Every week, I try to pour something into the mental cup, a story, a jewel life lesson, or a little spark that might help you build a better life of business. This weeks fountain blends adventure, mother nature, and some practical takeaways for raising capital or strategizing your next big move.

Here’s what’s inside this week:

  • Another near drowning deep in the Caribbean Sea (a lack of a good plan, a storm, a broken compass, and a bucket of KFC)

  • When I started speaking, and how it’s become one of my favorite things I do - humbly getting great reviews

  • Different types of startup funding — bootstrapping to venture debt

Estimated Read Time: 7.5 minutes

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FOUNDER STORIES

Day 1.

It was a beautiful day in the harbor of Nassau, Bahamas when we set away on our 33-foot double engine boat on what was meant to be a 3-day journey of island hopping, beautiful sunsets sipping Piña Coladas and Kalik’s .https://en.wikipedia.org/wiki/Kalik

Our captain was John, a construction superintendent and commercial fisherman who was deaf in one ear. The crew was myself, my dad, a construction mechanic named Sean and we set out with alot of beers, a few fishing rods, and a last minute bucket of KFC.

We were not the best crew headed out on the ocean that day but what we lacked in experience we made up for with naive optimism.

The Bahamas, an archipelago of approximately 700 Islands range south like pieces of pepper in the sea to Turks and Caicos. As we left the harbour we had already engaged in a near fatal mistake. We left without a plan. We unfolded our map and knew the destination was Providenciales, Turks and Caicos.

The ocean was calm as an ocean can be and we had a satellite phone to communicate as cell coverage wasn't going to exist on the small Islands we were going.

Ogopogo is the name of a lake monster from the lake I grew up on in British Columbia, Okanagan Lake. We took the name off the boat we bought in Nassau and renamed her Ogopogo. We came to learn that renaming a boat is bad luck - and were reminded constantly of this in the following days.

Day 2.

We set sail toward what we hoped would be another nice day. The waves started the day larger and the wind was light as we set on toward the destination. We fished and took turns at the wheel, watching the way-points and the manual compass on the bridge, floating calmly.

As the afternoon began to set onto night the waves grew larger, and the wind was picking up.

We thought we would have made better time throughout the day but the currents (which we knew little about) and the open ocean (no islands in sight for hours) was starting to move our little boat like a toy. We all understood we were not in the best situation but as the sun set and it got dark, the real storm started on us.

The waves picked up and the boat began to slam into the next wave. Jon the captain who always wanted to hear the conversation would look to the side to listen with his good ear, which kept turning the boat and not keeping it straight. The motor rod seal was letting in some water after two days of constant running, the compass was bobbing all around now, and for the first time in my life, I saw my Dad pray.

One of the cabin windows broke and water would come in with each wave. Shaun was bailing from the engine compartment and I was bailing from the cabin.

We could see a lighthouse in the horizon and tried our best amongst the waves to reach what we hoped was safety. We believed it was White Island - but we were unsure if we were going to be boating in or swimming for our lives.

Our boat and our bodies limped around a point and we made into into a small bay. Beside a real shipwreck, we dropped anchor and no one slept on land that night. We were soaked with seawater from the mist and spray and that hardened like marble on our hair.

After a rough sleep and a “thank you” to the lord for not putting me, my dad, or any of us into the ocean, we awoke with the hope of calmer seas. But that was not the case.

Day 3.

We were supposed to be pulling into Turks by this day, but we were still many nautical miles and islands away.

Learning from the lessons of the day before, we stayed put on the deserted island for the day. On the horizon we saw a boat; it was the Bahamian Coast guard and the US Coast Guard drug trafficking monitoring ship. The inflatable arrived at our boat, asked for our identification and if we had any drugs on board.

They boarded the Ogopogo for a look around. Serious officers with large guns who did not fuck around. Once they were satisfied were were not drug runners, they warned us about the size of our boat in the sea. They de-boarded and motored off into the horizon - we felt a little safer and less safe at the same time. 

My dad and I walked the island and found old high heeled shoes and other examples of when the island had people living on it, flashes of a lighthouse keeper and Caribbean life.

It was a great day looking back - spending time with my dad, checking out the shipwreck, the lighthouse, and calling my worried mom, his worried wife, on our satellite phone. We made a fire on the island and the four of us lived like castaways for a day. The beers and Kentucky Friend Chicken which were once in abundance had now run low.

Day 4.

We were ready to sail on. The Caribbean sea was nicer to us this day and the currents and waves gave us a confident window to proceed.

After a long day of sailing, we came to the realization we were not going to make Turks by nightfall. So we altered course slightly and set for Mayaguana - an island not well known, but we came to learn famous for its air strip for drug cartels and as a stop for the “Mail Boat” which keeps many outer islands running with diesel, food, and supplies.

So as we neared the island, a small tin boat with a motor approached. Smokey announced himself to greet us and inquire about who we were and our intentions.

We said we were amateur sailors who were running low of fuel, beer, and chicken. We threw anchor and rode with Smokey to shore. Mayaguana was a very uninhabited island with very few residents, a store, and a hotel with about 5 rooms. They were down to (1) bar of soap for us to break into 4ths and had one coca cola to drink and mix with some rum. The hotel’s only shower did work and when I tried to get the soap into the statue which was now my hair, the strands barely moved.

My dad had called my mom and she was glad we were alive. That being said, we were marooned on this island as the storm prevented the mail boat from arriving on schedule and was now the mail boat was at least another week away.

So, as my Dad did (and taught me to do in my life), he thought outside the norm, and instead of trying to find another boat, captain, or resources, he used the remaining battery on the satellite phone to call the Provo airport and booked a private small prop plane to pick us up on the dirt runway built by Pablo. We gathered our things, hopped in the back of the truck, left Ogopogo in the harbour, and went to the airstrip.

Our plane came into the horizon and we all smiled with relief, thankful for the adventure, wiser, and happy it appeared we made it through. 

As we flew on the small plane, I looked out the window and saw the little pieces of pepper that were the islands we were hopping from - realizing our boat was but a spec out there and we were lucky that we didn’t end up in the Caribbean sea. 

So the motto of this story is: its great to adventure, but dont leave the harbour without a plan. Metahor - what harbours of life are we coming and going from and do we have the right plan and resources for mission success.

The sea can easily take you down and it was more powerful and immense than I knew before that voyage. Also, it now ,my lucky charm to take a little KFC when one goes fishing.

Life is for giving it a go, but I have danced too close with Neptune a few times and lived to tell about it. 

Value life and the adventure.

As my mentor Jim Rohn says were not guaranteed next spring, on average a North American male gets 81.6 springs, so enjoy the short time we have on this ball spinning and floating through space.

I can still see the lighthouse in my minds eye and hope you find some adventure. 

What did you think of the story

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Different types of startup funding

In future sections of the legal beagle we’re going to go through the specific details of various deal structures and what terms to look out for but today we’re just going to start with the foundation of raising money, and tips on how to pitch in each scenario.

Bootstrapping

Bootstrapping refers to self-funding your startup without external capital.

When it makes sense:

  • Early-stage startups validating their business idea.

  • Founders wanting maximum ownership and control.

  • Businesses with minimal initial capital requirements.

How to approach:

  • Use personal savings, revenue reinvestment, or loans from friends and family.

Angel Investors

Angel investors are high-net-worth individuals investing personal funds for equity, often providing guidance and mentorship.

When it makes sense:

  • Early-stage startups needing capital to prove market viability.

  • Businesses requiring strategic guidance or industry connections.

  • Founders comfortable sharing ownership.

Venture Capital (VC)

VC firms provide institutional funds to startups with high growth potential, typically in exchange for significant equity stakes.

When it makes sense:

  • Companies with proven product-market fit and substantial growth potential.

  • Businesses needing significant capital for rapid scaling or market entry.

  • Founders comfortable with strategic oversight from investors.

Pitch tips:

  • Clearly outline your market opportunity, competitive advantage, and growth strategy.

  • Showcase traction, customer testimonials, or revenue growth.

  • Highlight your team's capabilities

  • Be clear and honest with your numbers. Stay away from broad estimates and overly optimistic projections.

Debt financing specifically for startups, typically requiring repayment with interest, reducing equity dilution.

When it makes sense:

Pitch tips:

  • Demonstrate consistent revenue streams or receivables.

  • Present clear financial projections and repayment plans.

  • Highlight existing backing from reputable venture capitalists or investors.

Debt Financing

Traditional loans or credit lines provided by financial institutions that must be repaid with interest.

When it makes sense:

  • Revenue-generating startups seeking funding without equity dilution.

  • Financing short-term cash flow needs or capital expenditures.

Pitch tips:

  • Provide clear financial statements demonstrating ability to repay.

  • Explain the specific use of funds and anticipated return on investment.

A hybrid between a loan and an investment, investors provide funding as a loan, but instead of repayment, the debt can convert into equity in the company later.

When it makes sense:

  • Early-stage startups that need funding but want to delay setting a valuation.

  • Founders looking to raise capital without immediately giving up equity.

  • Investors seeking downside protection with upside potential.

Pitch tips:

  • Clearly outline the trigger events for conversion (e.g., next funding round)

  • Explain the discount rate or valuation cap to show investor upside.

  • Demonstrate a path to growth that justifies conversion into equity.

Raising funds from many individual supporters through online platforms.

When it makes sense:

  • Consumer-facing products seeking early market validation and exposure.

  • Founders aiming to leverage community engagement for brand building.

Pitch tips:

  • Develop a compelling narrative and engaging video.

  • Clearly communicate the unique value of your product or idea.

  • Offer attractive rewards or early-bird incentives to motivate contributions.

Each funding source requires a tailored approach, aligning your pitch with the expectations and interests of investors or lenders, ensuring clarity of purpose, strategic planning, and a compelling case for investment is key.

Why I Started Public Speaking

I have always found it easy to share ideas with people. I didn’t setout to be a public speaker, but I have been asked to share my story and over time my philosophy. Most of my time has been spent building, and problem solving, and adventuring. But along the way, people started asking me to share the story of Saxx or how I think about Branding and behind it all: the values, the risks, the lessons, and the mindset that helped carry me through the ups and downs.

I have recently been doing more speaking and have meet some incredible people at events across North America in the past few months, my Alma Mater Western University, EO - Entrepreneurs Organization Canada, EO - Vancouver (Austin Retreat) or last week at Cactus Club AGM in Vancouver. I share my failure to make the big leagues in baseball, and a few W’s and remind people to beleive in themselves.

I remind you to believe in yourself and you can do anything in the whole wide world.

Cactus Club 2025 AGM (Vancouver, BC, Canada)

When I speak, I try to connect with companies and people trying to find their next gear, a team looking for ideas, or a group gathering around a strategy of shared purpose.

Last time I spoke I tried to make the room

I’ve had the honor of receiving happy clients and reviews and I always prepare and work hard to do a great job. Thanks especially to my Mom for always being genuine and showing me first how to communicate with and also listen to people. Also thanks to Mike Sider - my professor at Ivey - who taught me so much about public speaking and continues to coach me today.

If you're putting together an event reach out to me and we can see if their is a fit.

Reply to this email with the subject line “Speaking” and let’s chat!

Thank you for the referrals. We are continuing the roll out of our referral program.

(1) Refer one person and I’ll send you my Personal Net Worth Template.
(20) Refer 20 and Ria and I will give you a 30 minute advisory meeting.

Please send and share your link to anyone in your network that might enjoy a sip from The Fountain.

Thanks for being part of the Fountain community. Thanks for the emails and questions. Thanks for sharing with others who could use some positive ingredients in their mental factory. Until next Tuesday - here’s an air hug and positive energy.

~ Trent

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