As a young adult, budding with ideas and romanticizing the startup life, a favorite genre of TV for me was startup shows like HBO’s Silicon Valley and Amazon’s Startup, among others. What did these shows have in common? They portrayed startup life as an unpredictable adventure that ranged between comical and life-threatening. But at the end of the day, it wasn’t necessarily about the destination, but the team.
This presents two problems:

1. Focus. If startups are about giving solutions, and the focus is on doing something cool with buddies all the time, then what are you actually solving?
2. Team. The same way a team can lead you to unimaginable success, it can lead you to unimaginable pain.

Moving away from often romanticized ideas and adventures of startup life, the themes of competence, trust, loyalty, and betrayal, value, and belief systems that form these storylines will also impact you heavily. And there’s no script writer to draft a happy or seemingly acceptable ending that makes the journey worth it. No, some journeys aren’t worth it. And the end doesn’t justify the means.

Why have cofounders?

I’m sure you’ve heard of that popular proverb that says if you want to go fast, go alone; if you want to go far, go together. There’s value in teamwork. But this heavily assumes that it’s the right team.

Cofounders are meant to be partners who operate under the same vision you have and offer resources crucial to the venture you want to bring to life. However, this is a marriage of purpose.
Any misalignment that’s left unchecked is a ticket to divorce.

Why would you need a cofounder?

The only valid reason → as a force multiplier. To fill critical execution gaps, you cannot bridge by yourself.

If so, then why do you have cofounders?

If it’s to address a need in your team and to bring balance to your startup, thumbs up. But…… If it’s only to meet VC preferences, you’re already making a very expensive decision. An example is deliberately and performatively having founders who share culture with VCs, which is quite the talking point in African ecosystems. Kenya is an example with the Mzungu-as-a-Service (MaaS) satirical critique, which translates to foreign-founder-as-a-service, detailing that you need a foreign founder to make headway with foreign investors.

Setting up teams to satisfy external requirements as opposed to internal needs is like a rushing into a marriage to a stranger, for optics. And you’re likely to experience at least one of the following kinds of cofounder archetypes.

• The promiser: Highly enthusiastic and quick to volunteer, but they struggle with execution and capacity planning. While their optimism is great for team morale, their tendency to overcommit creates bottlenecks. To work with them effectively, you must implement strict accountability frameworks and translate their enthusiasm into clear, measurable deliverables.
• The carte blanche founder: Highly ambitious but disconnected from early-stage financial realities. They operate under the assumption that resources are infinite, focusing on scaling or acquiring tools before validating the need. Working with them requires setting rigid budgets and tying every proposed expense directly to a clear, near-term ROI.
• The panelist: Excellent at identifying flaws but reluctant to build the solutions. They often act more like a board member or an industry critic than an early-stage operator. To make this dynamic work, their analytical skills must be redirected from mere critique to active problem-solving, forcing them to own the solutions to the problems they point out.
• The grafter: They might lack highly specialized expertise on day one, but they make up for it with extreme adaptability and a willingness to learn. They are the ultimate utility players. While they require patience and guidance early on, their resilience and work ethic often make them the operational backbone of the company in the long run.
• The consultant: Highly strategic but hesitant to get their hands dirty. They provide excellent high-level frameworks but struggle with the messy, tactical execution required in the trenches. They need to be pushed out of the advisory seat and assigned direct, operational KPIs to ensure they are building, not just theorizing.
• The face: Naturally charismatic and exceptional at networking, pitching, and customer-facing roles. While they are invaluable for fundraising and sales, they can easily become disconnected from the product’s reality. They must be continuously tethered to the operational team to ensure that what they are selling aligns with what is actually being built.
• The newbie: Often battling imposter syndrome, they underestimate their own value and may initially hold back in strategic discussions. They require strong mentorship and an environment that builds their confidence. Once they find their footing, their fresh perspective and eagerness to prove themselves make them incredibly dedicated partners.
• The MVP: The rare balance of strategic thinking and relentless execution. Whether technical or non-technical, they understand what the business needs at any given moment and deliver it reliably. They are self-managing, highly accountable, and adapt seamlessly to the unpredictable nature of startup building.

What do we learn? Personalities play a huge role in the success of a team where you’re expected to wear many hats. An imbalanced team is ripe for failure.

The problem

You don’t truly know who you’ve gotten into bed with. And so you go learning along the way. Quickly, it dawns on you that, as proficient as they are with their work, it’s the much-overlooked aspects like character that drive a wedge between you the most.

Technical brilliance cannot outrun a character deficit, as the consequences are legal and financial ruin at the very least.

In the Kenyan ecosystem, the case of Pawa IT Solutions is a glaring example. The Employment and Labour Relations Court ordered the company and its CEO to pay a former employee about $10,000 after finding that the company failed to protect her from sexual harassment and assault.

The court ruled that the CEO’s conduct, combined with the company’s inadequate internal response, forced the employee to resign, amounting to constructive dismissal.

The CEO’s defence claimed that his conduct represented an “informal, fun” workplace culture that relied on jokes and innuendo.
“By all means, making fun and using joke innuendos should not have included sharing sexually explicit material and texts with the Claimant, who was his junior colleague and direct report,” the judgment read. “ That was conduct that was simply not acceptable in the workplace.”
The court also examined an alleged sexual encounter, which the CEO claimed was consensual. The judge cited the claimant’s immediate hospital visit and post-rape care form as strong evidence that it was not. Ultimately, the founder’s toxic character instantly became a severe liability for the entire company.

We see this pattern constantly. Across the continent, Nigerian fintech giant Paystack had to dismiss its co-founder and CTO, amid public allegations of workplace and sexual misconduct—triggering a massive governance crisis just after their acquisition by U.S. giant Stripe.

Globally, the ultimate example of character contagion is the Jeffrey Epstein scandal. Top-tier executives and billionaires learned that proximity to compromised character permanently destroys credibility. Apollo Global Management CEO Leon Black and Barclays CEO Jes Staley were both forced to step down from their empires, while tech titans like Bill Gates suffered severe, irreversible reputational damage simply for taking meetings with him. Who you build with becomes your permanent record.

But wait, there’s more….

Here are more examples of how poor character plays out in the boardroom:

Temper and impulse

The impulsive cofounder who publicly berates employees or snaps aggressively at investors during a stressful pitch. Their temper creates a toxic, fear-based culture, leading to high talent churn and blown funding opportunities. You eventually get trapped in their blast radius.

Steph Korey (Away Luggage)

Korey became infamous for her explosive temper and intimidation tactics. She would publicly berate her customer service team in company-wide Slack channels at 3 AM, aggressively canceling their paid time off as a punishment for perceived slights. Her temper trapped her team in a blast radius of anxiety, eventually leaking to the press and causing a massive PR disaster that forced her to step down as CEO.

Saboteurs and thwarters

These come in at least two ways;

→ The cofounder with a hidden agenda who does a bait and switch on the company’s foundational vision.

This creates a new cofounder archetype: The politician. Highly charming to the public and investors, but internally relies on manipulation to maintain control. They operate by information asymmetry…saying one thing to one person and the exact opposite to another.

Rather than leading through clarity, they consolidate power by pitting executives against each other and sowing deliberate chaos. Working with them means you are constantly double-checking their words against reality. This drains the team’s operational energy into internal politics.

Elon Musk vs. Sam Altman (OpenAI)

This is the crux of the May 2026 trial. Musk testified he was a “fool” who was swindled into funding OpenAI with $38 million under the strict, foundational promise that it would be a non-profit dedicated to open-source safety for humanity.

Musk alleges that once Altman and Greg Brockman used his money to build the technology, they thwarted that path—sneakily flipping the script, converting to a closed, for-profit model with Microsoft, and unjustly enriching themselves.

→ The cofounder who torpedoes a massive acquisition deal or a crucial enterprise partnership behind your back.

Driven by ego, jealousy, or a hidden personal agenda, they secretly kill the company’s biggest breakthrough right at the finish line.

Manish Maheshwari (Invact Metaversity)

After raising millions, Maheshwari and his cofounder fundamentally clashed on the company’s vision. When the board attempted to orchestrate an acqui-hire to save the failing company, Maheshwari reportedly held the startup hostage, refusing to step down unless he was given a massive cash payout and more equity than he had vested. His ego stalled the negotiations, effectively killing the company’s exit strategy at the finish line.

Aesthetics

The aesthetics-only cofounder. They are entirely enamored with the startup lifestyle:the networking events, the title, the aesthetic, but they lack a product roadmap, a customer acquisition strategy, or the grit to execute. A company cannot survive on a recreational atmosphere. Minus a concrete vision for solutions, the startup perishes.

Ja Rule & Billy McFarland (Fyre Festival)

As one of the most widely documented startup failures in modern history, Ja Rule was the ultimate aesthetics-only partner. He was entirely focused on the aesthetics—the supermodels, the Instagram marketing, and the luxury lifestyle pitch.

However, there was absolutely zero operational vision, product roadmap, or logistical execution in place. The company famously perished on a Bahamian beach.

Stench of bad company

The cofounder who normalizes cutting ethical corners. It starts small, but soon they are faking user metrics, lying to VCs on due diligence, or misusing customer data. Their lack of integrity eventually corrupts the company’s baseline ethics and exposes you all to legal ruin.

Charlie Javice & Olivier Amar (Frank)

Javice normalized a culture of deceit by enlisting her Chief Growth Officer, Amar, to help fabricate a list of 4 million synthetic users. They used this faked data to secure a massive $175 million acquisition from JPMorgan Chase. Their shared lack of integrity corrupted the entire deal, eventually leading to their arrests and convictions for securities, wire, and bank fraud, and conspiracy to defraud.

Talent over character

When a principled founder turns a blind eye to a toxic cofounder or employee simply because that person is a 10x developer, a top salesperson, or deemed too valuable to lose. By compromising your values to accommodate their character deficits, you pollute the entire company culture, making the well undrinkable for the rest of your team.

Sam Altman’s Reinstatement at OpenAI

In May 2026, former CTO Mira Murati and cofounder Ilya Sutskever testified under oath that Altman exhibited a “consistent pattern of lying.”

Mira Murati testified that Altman explicitly lied to bypass the internal safety review committee for a major AI model release. The board originally fired him for being “not consistently candid.” Yet, because Altman was the face of the AI boom and held the keys to Microsoft’s billions, the investors forced the board to surrender and reinstate him.

By giving way to a documented pattern of deception to save their valuation, they soured the atmosphere of the organization, leading to a mass exodus of the company’s top safety researchers.

Uber’s early engineering culture

During Travis Kalanick’s tenure, leadership explicitly turned a blind eye to severe misconduct by “high-performing” engineers. When engineer Susan Fowler reported severe sexual harassment, HR told her they wouldn’t punish the manager because he was a “top performer.” Compromising baseline values to accommodate wicked behavior triggered a mass exodus of talent and an eventual total overhaul of the board.

Zero financial restraint

The financially reckless cofounder. The moment the seed funding hits the bank account, they burn through it on premature scaling, expensive PR retainers, or luxury software tools before the startup has even achieved product-market fit.

Domm Holland (Fast)

The 1-click checkout startup raised an astonishing $120 million from Stripe and immediately burned through it. The CEO spent wildly on NASCAR sponsorships, expensive PR stunts, and heavily bloated payrolls before the core product even worked properly. They blew through hundreds of millions of dollars while generating a mere $600k in revenue, spectacularly collapsing the company.

The unreliable partner

The unreliable partner in a crisis. Startups are a series of fires. When a major server crashes, a key client churns, or the runway drops to zero, this cofounder goes AWOL or crumbles under the pressure. You are left completely alone in the fight, proving that having the wrong partner is far more dangerous than fighting alone.

Antje Danielson & Robin Chase (Zipcar)

In the early days of Zipcar, the two friends split equity 50/50 based on a handshake. But when the grueling reality of building the startup set in, Chase threw herself entirely into fighting operational fires, while Danielson refused to quit her day job, barely contributing from the sidelines. Chase was left completely unsupported in a crisis, leading to intense resentment and a brutal, relationship-ending split.

The solution

Based on the previous sections, you may be tempted to think that I’m against having cofounders. But I’m simply championing thoroughly evaluating the fitness of your prospective cofounders for the role.

When forming a team, focus on people you have something to learn from. And people who are willing to learn from you as well. Lessons don’t have to be limited to business. This is how you sharpen each other, not only as professionals, but as effective people. This also sets a healthy base for correcting and challenging each other.

Additionally, there’s a greater ROI from such a base. When the testing days in the life of your startup come (and they will), you need your warriors in your corner. When it’s all hands on deck, you need your team to be part of progress, and not a problem you need to add to the growing list of things to fix.

It’s wise to evaluate your prospective cofounder beyond their professional qualifications. Learn who they spend time with. The sentiments they share online. What they do in their free time. Get to know who you’re getting into bed with. Should you think this is an unnecessary step, boy oh boy, just wait for when your cofounder’s closet skeletons become yours by association. And the time, effort, and resources to be sunk into convincing other stakeholders that you had no idea, had no concerns, or no ties to such.

Simply, ascertain character. That’s what the world needs more of. Leaders of character. Skills change, requirements change, personalities shift. Character is an absolute; it’s either good or bad, and either side is infectious.

What brings you together? Why did you form your team? Evaluate why you’re coming together. Having a collective purpose that’s much greater than just making money is ideal. Remember, if it’s just money, that’s a pretty decent template for greed and distrust. We see internal contention for equity ever so often.

Look at the genesis of Facebook, where Eduardo Saverin’s shares were controversially diluted behind his back to push him out, leading to a bitter, highly public lawsuit. Or consider Snapchat, where early cofounder Reggie Brown was ousted by his friends and had to wage a massive legal battle, eventually settling for $157.5 million just to disappear.

When the mission is just money, your stake in your entity becomes fair game for enriching someone. Internal politics end up overshadowing the purpose.

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Here’s a simple team formation checklist to help you do a simple evaluation of prospective team members.

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“If you’re like, ‘Really, I’m gonna need a vacation to recover from my vacation,’ it might be the wrong choice.”

Daniela Amodei

Also, when circumstances like market fit, funding, and reputation change for the worse, if you can’t count on your team to weather it out, these expected tremors become a death knell for your venture, as mindsets shift to self-preservation of individuals.

However, with a genuine desire for impact, money becomes a by-product. And when circumstances, such as the aforementioned, change, the now doesn’t threaten the long-term goal. The project becomes much bigger than you and your founding team. It’s a reminder, a commitment, and a solid base for organizational culture that goes beyond the founding team to stakeholders, including the consumer.

Anthropic co-founder and president, Daniela Amodei, puts it impeccably, “Instead of starting a company together, go on vacation together,” she recently declared during a talk at the Stanford Graduate School of Business. “Share a room with them. Be like, ‘How did that go?’ And if you’re like, ‘Man, all I wanna do is spend more time with you,’ great.”

“If you’re like, ‘Really, I’m gonna need a vacation to recover from my vacation,’ it might be the wrong choice.”

I’m on the wrong team

All the above solutions sound so doable when you’re in the team formation stage. But what happens when you suspect that the boat sailed and that you’re on the wrong team?

Talk

Evaluate your team through conversations. Exercise wisdom, of course. This isn’t an opportunity to arouse suspicion or trigger premature defensiveness. Test the current motivations, convictions, intentions, and alignments of your team. You may realize that they’re not the wrong team, but just a bit misaligned.

The structural carrot and stick

After talking, you’ve now determined that you’re in the wrong team. You have decisions to make at this point. Whether to retain the team, bin the team and start a new one, or leave the team and venture entirely.

All these decisions, aside from leaving the startup, assume that you have the authority to make such moves. Implement mechanisms that reward long-term vision (the carrot) and heavily penalize mediocrity or bad faith (the stick).

I am neither encouraging nor supporting mutiny, but founders must protect the entity.

Should you see it fit to retain the team, depending on your legal setup, get legal counsel on how to legally and ethically insert and amend clauses to reward commitment, character, and selfless long-term vision. Conversely, add those that punish lack of character, mediocrity, and a lack of ingenuity, as this is a founding team; some sort of a legal carrot and stick approach. Examples of these alignment structures are:

Vesting

This is a standard defense mechanism. Founders do not get their equity upfront; they earn it over a standard schedule (typically 4 years).

• Reverse vesting with a cliff: The cliff (usually 1 year) is the ultimate stick: if a founder leaves or is ousted before the 12-month mark, they walk away with zero equity. However, if they hit that 12-month mark, you’re vulnerable to founders executing what we’ll call a cliff-and-run, in which partners are comfortable looking elsewhere when they receive their stock options.
• Milestone-based vesting: Instead of time-based equity, tie a portion of vesting to concrete execution goals (e.g., shipping the MVP, hitting revenue targets). This rewards actual ingenuity and penalizes those trying to critique from the sidelines.
• Back-Loaded Vesting (The Amazon/Snap Model) Instead of vesting an equal 25% every year, back-loaded schedules heavily weight the equity toward the later years. A common structure is 10% / 20% / 30% / 40%. Why it works? If a co-founder tries to jump ship after Year 1, they only walk away with a measly 10% of their allocation. To get the real payoff, they are forced to stick around for years 3 and 4. It naturally repels the quick cash-out archetypes.

Mira Murati’s highly anticipated startup, Thinking Machines Lab, has lost a third of its founding team to rivals. Despite securing billions in funding and offering massive long-term equity, various founding members walked away from the one-year-old startup just months after receiving their stock options.

Why? I acknowledge that there are a variety of factors, but a major one is simply that competitors offered immediate, massive cash payouts.

The long-term equity structure worked exactly as intended→it filtered out those who weren’t in it for the long haul. Furthermore, Murati reportedly had to execute the ultimate stick, terminating a key leader over unethical conduct (who then joined OpenAI), triggering a messy, public unraveling of the initial team.

Lesson? Quite stark. You can draft the tightest vesting schedules in the world, but if your partners aren’t aligned with you, the team will conform to market pressure.

Still, wise practice would be to explore different types of vesting best suited to you and your setup. Learn more about vesting schedules here.

Good leaver vs. bad leaver provisions

These clauses define what happens to a founder’s shares if they exit. A good leaver (e.g., leaving due to illness or mutual agreement) might retain vested shares. A bad leaver (e.g., fired for fraud, gross negligence, ethical breaches, or going AWOL) forfeits both unvested and vested shares. This directly punishes character deficits.

Shotgun clauses (Buy-sell agreements)

If the team is completely deadlocked, this clause allows one founder to offer to buy the other’s shares at a specific price. The second founder must either accept the buyout or buy the first founder’s shares at that exact same price. It forces a swift, fair resolution to toxic team dynamics.

Keep in mind that contracts still cannot fix character. That’s a market reality. Legal architecture is mandatory, but it is not a cure-all for a misaligned team. Additionally, we’re in an age where fierce talent wars are the norm, especially for AI talent.

The reset: Retain, bin, or leave

If neither the operational carrot nor the legal stick corrects the behavior, you cannot let the situation fester. A toxic or unproductive founder is a hole in your venture’s bucket (these holes are character, wisdom, vision, purpose, and belief systems, too), and that leak will eventually drain the capital, culture, and vision of the entire company.

A couple of clinical questions should dictate your next move: Setting sentimentality aside, is this specific venture worth the immense friction of cleaning house? Furthermore, do you possess the legal authority to actually do so?

If both answers are yes, consult your legal counsel on the most honorable, amicable, and airtight way to substitute the outgoing members. Candidly explain your position to the outgoing team. Meanwhile, you should have identified the replacements using the formation frameworks we’ve already covered. But it’s worth noting that exits are rarely as clean as they sound on paper; none of these should be unilateral decisions without legal backing.

If the answer is no—if the venture simply isn’t worth the trouble of defusing a ticking time-bomb of a team—you may be better off leaving and starting entirely afresh.

Never be afraid, discouraged, or embarrassed to walk away from a broken cap table. Your venture is not your life. It is simply a scalable expression of your capabilities and productivity. You can always build other scalable expressions, but you cannot build another life.

Alliances are the currency of the modern builder. Before seeking external alliances with investors or the market, ensure the internal ones that matter most are absolutely rock-solid.