Pre-Cana

Although neither my wife nor I are Catholic, we were married in a Catholic church. Why is a story for another time.

One requirement of a Catholic wedding is participation in Pre-Cana, a marriage preparation course.

Pre-Cana comes in many formats, but the curriculum is consistent. Over a series of sessions, couples are asked to discuss and align on expectations around major life topics such as family planning, finances, careers, and roles and responsibilities.

The goal is simple. Ensure alignment on core values before standing at the altar and committing to a lifetime together.

Regardless of your religious affiliation or personal beliefs, it’s a good idea. Many couples enter marriage without fully understanding what each person expects from the relationship or even from life more broadly.

Years later, conflicts surface over things like how many kids to have or who does the laundry.

More often than not, the tension stems from topics that were never discussed at all, or conversations that felt uncomfortable in the moment and were avoided. The excitement of new love has a way of blinding people to these gaps.

I’ve both seen and experienced the same dynamic in business.

In the early stages of a new venture, founders are often so eager to get started and build momentum that they avoid anything that might slow them down. That includes the hard conversations with their co-founders, partners or spouses.

Just as avoiding these conversations can doom a marriage, they can derail even the most promising businesses.

The Cost of Avoidance

The day-to-day reality of building a business rarely sounds like, “What will I accomplish today?”

It’s closer to, “What do I have to let slide today?”

The to-do list is always longer than your time, energy, or attention. Something has to give.

In the early days, avoidance can even masquerade as progress. The product is shipping. Customers are signing up. Revenue is coming in.

So why slow things down with uncomfortable conversations about roles, equity, or long-term goals?

Because avoidance behaves like debt.

The conversation you skip today doesn’t disappear. It compounds.

If discussing your role in the company feels uncomfortable now, wait until the business forces the issue after outside investors are involved, when a crisis hits, or when real money and reputations are on the line.

By then, you won’t be having a conversation.

You’ll be negotiating under pressure.

This is how small, avoidable misalignments quietly turn into irreversible fractures.

And while every founder breakup looks different on the surface, most follow the same underlying pattern.

They fail in predictable ways.

Which brings us to the five failure points that show up again and again in co-founder relationships.

Five Failure Points for Co-Founders

Vision Drift

Businesses start with the shared idea of a product, a service, or problem worth solving. Early on, alignment feels natural because the vision is still abstract.

Drift begins when decisions are required to turn that vision into reality.

Growth versus profitability.

Speed versus sustainability.

Control versus optionality.

One founder may want to build a large, enduring company. Another may want flexibility, income, or a faster exit. Neither is wrong but they are misaligned.

Vision drift rarely shows up as open conflict. It surfaces as hesitation, friction, and second-guessing around big decisions like hiring, fundraising, and reinvestment.

What looks like a strategy debate is often a values disagreement that was never discussed.

If founders aren’t aligned on what success actually means, the business will eventually force the decision for them.

Role Ambiguity & Resentment

In early-stage businesses, everyone wears multiple hats. Some fit. Others don’t. But they get worn anyway because the business depends on it.

Founders know the importance of putting the right people in the right roles. Yet their own roles are often the least defined and the least revisited.

At first, ambiguity feels flexible. Over time, it can create friction.

Responsibilities blur. Effort feels uneven. One founder starts doing more of the work they dislike, while another avoids it altogether.

Resentment doesn’t come from working hard.

It comes from unclear ownership and unspoken expectations.

Founders need to be honest about strengths, weaknesses, and role preferences and revisit those conversations as the company grows.

Roles that work at the beginning rarely work later.

Ignoring that reality is how resentment, burnout and other maladies appear.

Equity, Compensation & Power

There’s a reason early-stage companies often raise capital without setting a valuation. Even professional investors know it’s too early to pretend the business has a clear value. At that stage, it’s mostly potential.

Founders, however, often do the opposite. They lock in equity, pay assumptions, and decision rights before roles, effort, and risk are fully understood.

Equity isn’t just ownership. It’s control.

Compensation isn’t just pay. It’s pressure.

And power determines how disagreements get resolved.

Misalignment shows up when reality diverges from the plan. One founder goes all in. Another can’t. One takes financial risk. Another needs stability. The structure, however, stays fixed.

What once felt fair starts to feel constraining.

The mistake isn’t choosing wrong but choosing too early and treating those decisions as permanent.

Once equity is set and money is involved, every disagreement gets heavier.

Power disparity always emerges.

You can design for it early but consider ways to revisit, unwind or adjust based on milestones or scenarios that would likely impact allocations.

Risk Tolerance & Decision Making

Every business runs on decisions. The problem isn’t making them, but making them together.

Founders often have very different relationships with risk. One is comfortable moving fast with incomplete information. The other wants certainty, data, and downside protection.

Early on, this difference is easy to ignore. Decisions are small. Mistakes are cheap.

As the business grows, decisions get heavier. Hiring. Pricing. Fundraising. Major bets that can’t be undone.

When risk tolerance isn’t aligned, decision-making slows. Debates replace progress. Momentum stalls while founders argue about timing, proof, or worst-case scenarios.

What looks like a tactical disagreement is usually philosophical. It’s about how much uncertainty each founder is willing to carry.

Most business can survive a bad decision.

However many drown in indecision.

If founders don’t agree on how decisions get made or how much risk is acceptable, the market will eventually choose a pace for them.

And it never waits for consensus.

Lifestyle Choices & Outside Obligations

Founders don’t just bring skills and experience into a business. They bring lives.

Family responsibilities, financial pressure, health, side projects, and personal priorities all shape how much time, energy, and risk someone can realistically take on.

Early on, these differences are easy to dismiss. Everyone is excited. Everyone is “all in.”

Over time, reality sets in.

One founder can work nights and weekends. Another can’t. One can go months without pay. Another needs income. One wants the business to scale aggressively. Another wants stability.

None of these are wrong. But they are not neutral.

When lifestyle constraints aren’t acknowledged, the company quietly bends around the most constrained founder. Resentment builds, not because priorities differ, but because they were never named.

Alignment isn’t about equal sacrifice.

It’s about clear expectations.

Ignoring lifestyle and outside obligations doesn’t make them go away.

They will surface later when the business has fewer options and less flexibility.

The Next Step

I recommend intentionally discussing all five areas with your business partner or co-founders. The goal isn’t perfect agreement but awareness. Identify where you’re aligned today and where tension could eventually emerge.

You don’t need all the answers but to align around a set of questions.

After working through the five failure points, capture the following in writing:

• What do we agree on today?

• What assumptions are we making?

• What would break our partnership?

• Which decisions require unanimity?

• What should we revisit periodically?

Your answers will change as the business grows. That’s expected.

What matters is having a shared reference point and a habit of revisiting it.

Alignment isn’t a one-time exercise. It’s an operating discipline.

And like any good relationship, the strongest partnerships aren’t defined by the absence of conflict, but by a commitment to keep the conversations going, especially when they’re uncomfortable.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.