Tech in Africa
Meshack Alloys shut down Sendy in 2024 after raising millions and failing to find sustainable unit economics. By late 2025, he was back. This time, he’s launching TABB, a fintech building trade credit infrastructure for African SMEs.
William McCarren watched Zumi, his Kenyan e-commerce startup, collapse after $20M in sales and 5,000 customers. Now he’s building again.
They’re not alone. 2025 has seen an unusual wave of high-profile founder comebacks. Founders who burned through investor capital, shut down their companies, and are now asking for second chances.
The question nobody’s asking: Should they get them?
According to Launch Base Africa, 68.3% of African founders who experience a shutdown never start another venture. Only 31.7% try again.
This makes 2025’s comeback wave statistically significant, and worth examining closely.
The 2025 Comeback Class
Let’s look at who’s actually coming back.
Meshack Alloys built Sendy, a Kenyan logistics startup that raised significant capital but ultimately couldn’t solve the unit economics puzzle. The company shut down in 2024. Now he’s in Silicon Valley building TABB, an “instant-acceptance trade credit network” that allows banks to issue revolving credit lines to SMEs. That’s a complete sector pivot: from logistics to fintech infrastructure.
William McCarren co-founded Zumi, a Kenyan B2B e-commerce platform that hit $20M in sales and acquired 5,000 customers. It raised venture funding and built a team of 150 people. But by March 2024, Zumi couldn’t secure the follow-on investment it needed and shut down. McCarren has since started exploring new ventures.
Notice something? These aren’t small failures. These are founders who had scale, traction, and investor backing, and still couldn’t make it work.
Now they’re back, often in completely different sectors, promising they’ve learned from their mistakes.
The African ecosystem is watching. And investors are facing an uncomfortable question.
If you’re a VC, here’s the dilemma:
On one hand, these founders have battle scars. They’ve navigated fundraising, hiring, scaling, and shutdowns. They know what NOT to do.
On the other hand, they already had their shot. And they lost investor money.
So what should you do when a previously failed founder shows up in your inbox?
The African VC ecosystem has typically been unforgiving. Unlike Silicon Valley, where failure is a badge of honor, African investors have historically been more conservative about backing serial entrepreneurs after a shutdown.
But 2025’s comeback wave suggests something is shifting.
The question is: Should it?
Why Second Chances Make Sense
They’ve Already Paid Tuition
There’s a saying in Silicon Valley: “The most expensive education is your first startup.”
These founders have already learned how to raise capital. They did it once. They know how to build teams because they’ve hired before. They understand what kills companies because they lived through it. They know how to shut down gracefully because some of them actually returned capital when possible.
That knowledge is worth something. A second-time founder doesn’t need to learn the basics. They can focus on execution from day one.
They’re Self-Selected for Resilience
Remember: Only 31.7% of failed founders try again.
The ones who come back? They’re the resilient ones. The ones who could’ve walked away, taken a corporate job, and collected a salary, but chose to build again instead.
That’s a signal. Starting a company after a public failure takes courage. You’re rebuilding your reputation from scratch. You’re facing skepticism from investors who remember your last venture. You’re carrying the psychological weight of having let down your team, your investors, and yourself.
The fact that someone chooses to do it again means something.
Pattern Recognition
A founder who failed once is less likely to make the SAME mistake twice.
Alloys won’t make Sendy’s unit economics errors again. McCarren knows where Zumi went wrong operationally.
The question isn’t whether they’ll make mistakes. It’s whether they’ll make new ones.
Look at the data globally. Many successful entrepreneurs had failed ventures before their breakthrough. The difference between first-time and second-time founders isn’t just experience. It’s pattern recognition. They’ve seen what breaks, and they know how to build around it.
Why VCs Should Be Skeptical
Past Performance Predicts Future Results
If a founder couldn’t build a sustainable business the first time, with capital, team, and traction, why will the second time be different?
Especially if they’re pivoting to a sector they don’t know. Logistics to fintech is a massive leap. You’re not just starting over. You’re starting over in unfamiliar territory.
Pattern recognition cuts both ways. Sometimes failure is a signal of poor judgment, not bad luck.
The uncomfortable truth is that some people are better at raising money than building businesses. Some founders are exceptional storytellers who can sell a vision to investors but struggle with operational execution. If that’s what killed the first company, there’s no reason to believe it won’t kill the second.
Opportunity Cost
Every dollar invested in a comeback founder is a dollar NOT invested in a first-time founder who hasn’t burned capital yet.
The African ecosystem has LIMITED capital. Should it go to proven failures trying to rebuild credibility, or untested founders with fresh ideas?
It’s a zero-sum game.
When a VC writes a check to a previously failed founder, they’re making a bet that this founder’s second attempt will outperform a first-time founder’s first attempt. That’s a high bar. And in an ecosystem where 64% of funds are under $50M, every bet matters more.
Reputation Risk
VCs who back previously failed founders take on additional scrutiny.
If the second venture also fails, LPs will ask: “Why did you fund someone who already showed they couldn’t execute?”
That’s career risk for the GP.
LPs don’t get romantic about second chances. They want returns. And when a GP has to explain why they backed the same founder twice for two failed companies, that’s a conversation nobody wants to have.
The stakes are higher for comeback founders because the downside isn’t just financial. It’s reputational, for both the founder and the investor.
Founders love the “fail fast, learn, iterate” narrative. But investors are playing with OTHER PEOPLE’S MONEY.
5 Questions VCs Must Ask Before Re-Backing a Failed Founder
Here’s what due diligence needs to look like if you’re considering funding a comeback founder.
Question #1: What ACTUALLY killed the first company?
Don’t accept “market timing” or “funding winter.”
Dig into the specifics. Were unit economics fundamentally broken? Did operations fall apart? Were there co-founder conflicts, scandals, or fraud allegations?
If the answer is governance or unit economics, be VERY careful. Those are founder-level failures, not market failures.
Market timing is when you build a great product but the market isn’t ready. That’s forgivable.
Unit economics failures mean the founder didn’t understand the business model. That’s a red flag.
Governance failures mean the founder couldn’t manage relationships, power dynamics, or organizational culture. That’s a deeper problem.
Question #2: What did they learn, specifically?
Ask: “What would you do differently?”
If they say “raise more money,” that’s a RED FLAG. More capital doesn’t fix broken fundamentals.
If they say “I would have validated unit economics before scaling,” that’s a good sign. It shows they understand the actual problem.
The answer reveals whether they’ve done the hard work of introspection or whether they’re just looking for another shot.
Listen for specifics. “I should have been more careful” is too vague. “I should have hired a CFO at $2M ARR instead of waiting until $10M ARR, and here’s why” shows real learning.
Question #3: Did they return capital or burn it all?
How a founder shuts down tells you about their character.
Okra returned $4-5M to investors when they shut down. That’s exceptional. It means they managed the burn carefully and prioritized investor outcomes even in failure.
Thepeer allegedly spent $50K on cars while generating less than $1K in revenue. That’s catastrophic judgment.
If a founder burned every dollar and left creditors unpaid, that’s not someone you want handling your capital again.
Question #4: Why THIS sector and idea now?
If they’re pivoting completely, they need to prove sector expertise.
Don’t let them learn on your dime twice.
Pivots are risky. You’re betting not just on the founder’s ability to execute, but on their ability to understand a completely new market, new customers, new competitive dynamics, and new regulatory environments.
If Alloys is pivoting from logistics to fintech, he needs to show he’s spent serious time learning fintech. Has he worked in the sector? Does he have co-founders with domain expertise? Has he built relationships with banks and regulators?
Otherwise, you’re funding a learning curve.
Question #5: Have they de-risked this one MORE than the last?
Look for evidence of customer validation BEFORE building. Pilot contracts or letters of intent. A co-founder with complementary skills they didn’t have last time. A smaller initial capital ask that says “let me prove it works first.”
If they’re asking for a $5M seed again, that’s a red flag. It suggests they haven’t learned that capital isn’t the solution.
The best comeback founders come back with less ambition and more proof. They bootstrap longer. They validate harder. They ask for smaller checks until they’ve demonstrated traction.
If they’re swinging for the fences again on day one, be skeptical.
The Verdict: Nuance Over Ideology
Here’s my take as someone transitioning into VC:
Blanket rules don’t work.
Some failed founders deserve second chances. Others don’t.
The difference? What killed them the first time.
I’d fund again if:
The market timing was genuinely wrong. They built a great product too early, or macro conditions crushed their sector. That’s not a founder failure.
They returned capital when possible. It shows integrity and good judgment under pressure.
They’ve de-risked this venture MORE than the last. They have customer validation, pilot contracts, co-founders with new skills, or proof of concept before asking for serious money.
They have NEW co-founders or advisors. If the same team is trying again, you’re betting on the same judgment that failed before. New blood brings new perspectives.
They’re building in a sector they KNOW. Domain expertise reduces risk massively.
I wouldn’t fund again if:
Unit economics were broken. This should have been caught early. If they scaled without sustainable economics, that’s poor judgment.
There were governance issues. Fraud, co-founder conflicts, or organizational dysfunction are founder problems, not market problems.
They’re pivoting to a sector they don’t understand. Learning a new industry while building a company is too much of a risk.
They’re asking for MORE money than last time without more proof. Capital doesn’t fix bad fundamentals.
The shutdown was messy. Lawsuits, unpaid vendors, or burned relationships tell you how they handle pressure.
The bottom line:
Failure isn’t disqualifying. But HOW you failed, and WHAT you learned, absolutely is.
2025’s comeback founders will test this thesis. Some will prove skeptics wrong. Others will validate why VCs should be cautious.
The question isn’t whether to fund failed founders. It’s WHICH failed founders to fund.
If You’re a Failed Founder Reading This
If you’re planning a comeback, here’s what you need to do:
Own what went wrong. Don’t blame the market. Don’t blame your co-founder. Don’t blame investors. Take responsibility for your part. Investors respect honesty about failure more than deflection.
Return capital if you can. Even if it’s a small amount, it builds enormous goodwill. It tells investors you prioritized their interests when things went wrong.
Take time. Don’t rush into the next thing. Spend six months to a year actually learning what went wrong. Talk to customers. Talk to former team members. Do the post-mortem properly.
Build in public. Show traction BEFORE fundraising. Start a newsletter. Share your learnings. Build a prototype. Get pilot customers. Prove the idea works before asking for money.
Bring new perspectives. Don’t rebuild with the same team or the same thesis. If your last CTO couldn’t execute, find a new one. If your go-to-market didn’t work, hire someone who’s done it before.
And remember: The ecosystem is watching.
Your second venture is your reputation’s redemption arc or its final chapter.
Make it count.
The Data Will Tell the Story
68.3% of failed African founders never try again. The 31.7% who do carry a burden: proving that second chances aren’t wasted chances.
2025’s comeback class has something to prove. We’ll be watching to see if they do.
The data on second-time founders in Africa doesn’t exist yet because the ecosystem is too young. But we’re about to generate it. In three to five years, we’ll know whether this wave of comebacks produces success stories or validates the skeptics.
