The Refined Introduction

Over the last decade, I’ve watched a lot of tech companies come and go. Some fail because the market isn't ready; others collapse because they can't solve the scaling puzzle. But the most frustrating—and honestly, the saddest—failures I see are the ones where a brilliant idea is killed by a broken legal structure.

I’ve seen it time and again: a founder has an incredible vision and the drive to execute, but they neglect the formal proceedings that actually protect that value. I was fortunate; in my first venture, I had experienced partners who insisted we get the legal work right on Day 1. From the moment we incorporated, we set a precedent for doing things the 'proper way'—a standard that still defines the Fello Agency today.

I am a relentless advocate for moving fast. I believe in momentum. But there are 'bare minimum' foundations that must be in place if a company is going to survive its own success. To dig into what those look like, I’m honored to interview Matthew McLeod. As a veteran in the legal space, Matt has seen it all. Today, we're cutting through the noise to discuss the essential principles every founder needs to master before they launch.

The High-Growth Architect: Who is Matt McLeod?

Most founders see legal as a hurdle to clear. Matt McLeod sees it as the blueprint for an exit.

As a Partner at Dickinson Wright and leader of the firm’s High-Growth Companies Group, Matt brings a rare triple-threat perspective to the table. He is a graduate of the Royal Military College of Canada with an engineering degree, a former Officer in the Canadian Forces, and a former executive at a private equity-backed SaaS company. Matt doesn't just practice corporate law; he understands the mechanics of building, scaling, and selling a business from the inside out. His background in the defense industry and his experience in the New York and Toronto tech corridors make him one of the most sought-after advisors for companies navigating Seed and Series A rounds. When Matt talks about "legal foundations," he’s talking about building a company that is engineered to be acquired.

The "Matthew McLeod" Top 5 Legal Pillars

1. The Day 1 Documentation: Why founders shouldn't wait for a "serious" conversation to have share issuances, director consents, and shareholder agreements in place.

2. The "Under the Hood" IP Check: The simple steps to ensure your company name and product IP are actually yours before you spend a dime on marketing.

3. The Shareholder Stalemate: How the absence of a shareholder agreement turns a simple disagreement into a company-killing legal battle.

4. Investor Readiness: Moving beyond a "disorganized cap table" and ensuring employment and loan docs are "buttoned up" for due diligence.

5. Proper Contracting: Why the era of "generic terms and conditions" is over, and how professional customer contracts protect your long-term scale.

The Founder’s Brief: An Interview with Matt McLeod on De-Risking High-Growth Startups

What are the most common legal mistakes you see early-stage founders make before they launch — and why do they keep happening?

I hate to say it, but putting off the legal documentation. I’ve dealt with 3 disputes this year already where founders started a business, didn’t enter into proper documentation and then had a falling out – what transpires is a costly fight that could have been avoided for a few hundred dollars. I think it happens, because people don’t want to pay legal fees, as they’re too expensive and not deemed “essential”

What's the minimum legal foundation a tech startup should have in place before going to market?

Basic documentation, share issuances, director appointments/consents, shareholder agreement, shareholder loan documents and employment agreements. You can probably get away without shareholder loan docs and employment agreements, but every investor is going to want those buttoned up (and/or paid off) by the time they invest.

How does a disorganized cap table or missing shareholder agreement actually show up and create problems later?

I’m actually less fussed about a “disorganized cap table”, if there’s 30 shareholders each holding a different class prior to any raise then it’s likely a challenge, but under 10 holding the same class, or a second class is usually not too challenging – generally investors are going to want to tidy it up a bit and simplify it (to give themselves the best position), but that’s usually not a massive hurdle. A missing shareholders agreement rears its head in really ugly ways – not being able to remove a problematic shareholder, former employee, or no documented way to break a stalemate in the business push it into the statute and generally litigation.

What IP mistakes do tech founders make early on that come back to haunt them during due diligence?

Not taking a peak under the hood at what’s possible. If you have a name that’s core to your business, or a product that is the basis of your business it behooves you to look and see if the product exists or name is taken. You don’t have to go crazy and patent everything, but you should look and see

What's something founders think is a "later" legal problem that is actually a Day 1 problem?

I think having everything in the company – IP should be done in the company (domains, etc. registered to company rather than individuals), Banking arrangements (same comment), and then the legal foundation described above. Separately, customer/client contracts should be properly documented, rather than just using an invoice or purchase order with generic terms and conditions.

What should a founder have ready from a legal standpoint before their first serious investor conversation?

I think the legal foundation described above is really the starting point.

Fello's thoughts

Over the last decade, I’ve watched a lot of tech companies come and go. Some fail because the market isn't ready; others collapse because they can't solve the scaling puzzle. But the most frustrating failures I see are the ones where a brilliant idea is killed by a broken foundation.

I’ve always been a preacher of moving fast. At Fello Agency, we focus on velocity and market traction. But as I’ve grown in my career, and through my own first business ventures, I’ve realized that you can only drive as fast as your chassis allows. If your legal structure is a mess, you’ll shake apart the moment you hit high speeds or try to raise a Series A.

I am honored to interview Matt McLeod. Matt is unique because he’s lived the founder's journey as an executive and an engineer before becoming a leading M&A lawyer. He understands that bare minimum legal isn't about red tape. It's about protecting your equity and ensuring your company is exit-ready from Day 1.