Biola Alabi has seen early-stage investing in African startups from all sides. She began as an angel investor, with her first cheque going to Big Cabal Media, TechCabal’s parent company. She later led angel syndicate deals with other angels before moving into venture capital, investing with firms like Acasia Ventures, and now at Delta 40.
Before she began backing African startups, Alabi worked as a regional marketing manager at Bigwords, an American startup that raised $80 million to build an online textbook marketplace before shutting down during the dotcom crash of the early 2000s.
That experience left a lasting impression—she and her colleagues only learnt the company had lost its funding through news reports—and later inspired her investment in Big Cabal Media, driven by a belief in the importance of transparency and resilience in startup building.
In 2003, fuelled by a desire to work on the continent, she took up the position of Africa Regional Director for Sesame Workshop, creators of the popular children’s show “Sesame Street”. But it was her next job as a managing director for Multichoice, the largest pay-TV operator on the continent, that brought her popularity as an operator. It was during this time that she began investing in startups.
Throughout her investment journey, Alabi’s thesis has consistently rested on a few key pillars. She places strong emphasis on founders and assesses their experience, commitment to the problem they are solving, and resilience in the face of challenges. As she once put it to a founder: “Why should I not expect you to leave in a year if a $2 million a year offer from Google comes along?”
She also looks for early signs of traction, valuing real-world use cases, actual users, or references who can testify that the product is solving a real problem. “There’s no business without a customer,” she told TechCabal over a call.
Given her background in subscription businesses and media, Alabi prefers to fund companies with multiple income streams and expects any startup she backs to demonstrate that it operates in a large, scalable market.
TechCabal spoke to Biola Alabi to understand her investment approach, thesis, and her advice for angel investors.
This interview has been edited for length and clarity.
You had a successful media career. At what point did you realise you wanted to start doing angel investing?
I’m not sure you actually realise you want to do angel investing. I think, a lot of times, angel investing comes to you. I was looking at different types of investments, and around that time, I started meeting founders through mentorships and other engagements. Then people just started pitching me. I’m not even sure exactly how it happened.
It started with setting up a meeting with me and telling me what they’re working on, and asking for my support. That’s how I wrote my first cheque and how I started angel investing.
Big Cabal’s founders came to me for an angel investor who can also mentor and invest. I loved what they were working on. I felt it was really important—especially for the ecosystem—so I invested.
And then from there, someone else said, “One of our angels…” and more people started pitching me. I eventually started joining angel groups, and that’s how I became a member of the Lagos Angel Network.
How were you able to put yourself out there to even be in a position to mentor people, and in a position where people could pitch to you?
Because I’d been in the media, people already knew me as a leader. I had been doing a lot of speaking engagements. I was also very interested in how I could support entrepreneurs, especially in the creative sector. For me, that was really one of the main things I was working on at the time.
There were a lot of people creating content, but the question was really, how do we monetise this content? I was helping people understand monetisation from a broadcasting perspective, the opportunities available, and why they should license their content to us as a broadcaster.
Because I was leading conversations on the continent about creating opportunities in the creative economy, I was already visible. There were quite a number of people I was either mentoring through work or through my office, and then the word just got out. People who were starting new companies began reaching out to me. I think it was just a natural evolution in my leadership journey.
Can you walk me through your experience as an operator, as someone who has worked in the media space and across different sectors? How did that shape the way you evaluate startups?
For me, when I’m looking at a company, the first thing I focus on is the customer because without a customer, there’s no business. Someone has to be willing to buy what you’re offering.
I’m always trying to understand how the customer thinks, why the customer is buying this product instead of another, and whether there’s early traction. A lot of times, you’ll find companies that have been trying to build something, but there’s just no traction. That usually means the market isn’t responding, and they need to figure out how to pivot or what to change.
I’ve worked in subscription businesses, so I also like to understand the revenue model. In my broadcasting experience, revenue came from subscriptions, sponsorships, and airtime sales. I’m always looking to see what the multiple ways are in which the startup generates revenue.
Then I think about the people leading the company: Can they actually make this happen, and can the people building this go all the way?
That’s what I’ve seen consistently, whether it’s in the companies I’ve worked at or with founders I’ve met: to get anything done within a big organisation, you have to understand who you’re selling to, how much you’re selling, and whether you have the people who can execute and see it through. It’s the same mentality I bring to evaluating startups.
Was there a particular moment or a particular deal that made you realise that Biola Alabi could directly accelerate a startup’s growth trajectory?
After I invested in TechCabal, I invested in a few other companies. Some of them I invested through syndicates, some I invested directly, and some I even led the syndicates. But I think the moment that stood out was when Big Cabal Media was going through its leadership transition.
I held the founding team’s hand through that transition to a new CEO, and managing that process made me realise that, yes, I definitely have the ability to handle crisis management and drive a crisis to a positive conclusion.
Leading that change and ensuring we achieved an amicable separation were things that, as an operator, you deal with every day. But for a startup, it’s often the first time they are facing challenges like that.
Helping people understand how to navigate that situation gave me really good insight into how my operating experience can be extremely useful for CEOs, especially when they’re facing operating challenges.
What did your first few angel investments teach you?
They taught me a lot about transitions and also about what it takes when you’re trying to refocus a company for growth. That was such a meaningful and educational experience for me.
I think the first thing I learnt is that there has to be trust between the founder and the investor. You have to trust the team, and you have to figure out early how to get to a place of trust.
Another thing it taught me is that you can do all the analysis, you can do all the reference checks, but if something still doesn’t feel right— if there’s something holding you back about a deal— you need to pay attention to that feeling.
I’ve done deals as an angel where I felt something holding me back, but I still wired the cheque anyway, and I did end up regretting it.
Is there any specific example that comes to mind? You were mentioning how you had initial doubts and eventually went ahead—anything you can share?
We invested in a company where we had done our due diligence. One of the angel investors who introduced the deal to us was someone highly respected. They said they had done business with the founder at their first startup, and they vouched for the founder’s integrity, especially in how the founder had transferred shares into the new entity we were investing in.
This very well-respected investor had also done a follow-on investment into this new entity that the founder was building. But something stood out to me. When I met the founder, they dropped some big names. I happened to know one or two of those names, so I called them. And while it wasn’t like they gave me a bad reference, it took them a very long time to even recollect who the founder was.
There was a misalignment between the relationship the founder had presented and the way these people actually remembered it. In one case, the person didn’t even really remember the founder at all.
I tried to brush it off, thinking we all meet so many people, maybe it wasn’t a big deal. But it gnawed at me. I didn’t like that the stories didn’t align, especially because when you’re investing so early, references become your lifeblood, your lifeline.
Anyway, we invested—me and my syndicate—and it’s definitely one of those investments you look back on and think, “I should have trusted my gut.”
What has been your most meaningful win as an angel investor?
My most meaningful win is still to come, but we’re in some really great companies that I’m super excited about—some through syndicates, and some through individual investments I’ve made.
For example, a company like TechCabal—I invested individually first, and then did a follow-on as part of a syndicate, because we needed to do a follow-on at a very critical time in the business. I think it’s a business that’s extremely impactful. I’m very proud of that investment and the work it’s doing in the ecosystem.
I also invested in an online savings and investment company. They’ve since been acquired, so we were able to have a partial exit there, but they’re still growing, and I’m still very impressed with their progress.
I’m invested in a couple of fintechs across West Africa that are growing very fast. Every time I get their monthly reports, I’m blown away. I’m very excited about a lot of my current investments—some in e-retail, some in fintech.
As for the things that haven’t done so well, I’ve also been able to learn quite a bit from them. One thing that’s becoming clearer to me is the big opportunity from a B2B enterprise perspective, and also B2C. I think B2C is coming and is going to be a huge opportunity, especially in commerce enablement. That’s something I haven’t done enough of as an angel, and I’d love to see more interesting opportunities in that area.
Almost every ecosystem starts with commerce, and then moves from there, because commerce unlocks many of the challenges in an ecosystem. Then fintech follows, because fintech has to solve the biggest commerce problem, which is payments. Those are typically the first waves.
I still think there will be big waves in health. Of course, everyone is talking about AI, so that’s obvious. But also, I think there are huge opportunities in data. Unfortunately, I have not yet found the right data company to invest in as an angel. But as a VC, we’ve been able to invest in some super interesting AI and data companies.
You didn’t mention what you would say was your toughest loss?
I don’t ever really think of them as “tough losses” because, as an angel investor, I’m not investing my kids’ college fund in these deals and I always tell people that sometimes my cheque is so small that I even tell the founder, “I don’t know if you want this check—it’s very small.”
A lot of times, when people are raising those early angel rounds and they really need an advisor, they’ll take what I like to call those “Mickey Mouse checks.”
Anytime you have to do a write-down, that’s a loss.
I think the toughest losses are when it’s fraud. I have had an experience with that, and that’s a tough loss, because it’s really an integrity issue. It makes everyone doubt themselves, who they are, and how they make decisions. You have to review your process again and make sure you are process-driven and that you are making investment decisions based on your principles and your investment thesis.
These are meaningful wins and tough losses. How did they shape your investment instinct?
They help you spot patterns, and they also help you start to build your confidence. You start to learn when to take chances, when not to, and whether you need more time. I don’t rush investments now. I know people want you to rush investments, but I think that during the 2020–2021 era, there were so many rushed deals.
There was an investment I made in a well-known founder who was starting something new.The valuation didn’t make sense, but we were sort of banking on this being a repeat founder. In the end, it just didn’t work—we ended up having to do a write-down.
It was done as a syndicate, and a lot of angels, especially new angels, were very upset. This was also a time when a lot of people were sitting at home, so there was a lot of idle capital being deployed, and we had many new angels joining syndicates. Helping new angels understand the real risk involved has been a big part of my learning, making sure they understand the time it takes.
Angel investing is patient capital, and having transitioned from angel investing into VC, I really understand now the importance of angels. I value angels, but I also understand the value of patient capital. Early on in our ecosystem, people thought investing in startups was going to be like investing in oil and gas deals or treasury bills, so they expected quick returns.
These experiences shaped me to understand that angel investing requires patience. It taught me the importance of having a process, trusting that process, tweaking it as needed, and also understanding that you’re making risky bets—and hopefully, high-risk, high-reward bets.
How do you approach conviction when you’re writing small personal cheques? What are you optimising for, and what conviction are your investments based on when you’re writing these small cheques?
Team and traction. Number one is, who is the team? Is it a one-woman show, a one-man show, or is it a team of really interesting characters solving a very important problem?
Another thing with angel checks is that I’m always asking: what are you solving for, and why is it important? I also ask people hard questions. For instance, there was a founder I was talking to—a PhD from an Ivy League school—and I said: “Why should I not expect you to leave in a year if Google calls you with a $2 million-a-year job?” because that’s the kind of person they are.
How they answer that question—and what they tell me about why this problem matters to them—really helps me understand if this is the right horse to back because that’s what you’re doing: you’re figuring out who to back.
Then traction. I want to see that people are using the product, that there’s some form of traction. It doesn’t always have to be paid traction—it could just be users. If I can talk to one or two users and hear how the product is really making a difference for them, that’s enough.
I also ask: who are these people? What have they done before? What kind of insight or unfair advantage do they have? Sometimes, it’s not that they were the number one engineer at their last job—it’s just that they have a unique insight into a problem that no one else has. I’ve seen that often with founders who leave startups: they spot a real gap they experienced firsthand, and now they’re solving it.
Another thing I look at is: who’s on the cap table? For example, if your former boss invests in you, I always think, “Okay, this is huge.” That brings a lot of credibility to the table. This is someone who has worked with you closely, who knows how you operate, and who still believes in you enough to invest.
I’ve seen that happen a lot—where either former bosses put in a cheque or even join as advisers. To me, that kind of endorsement early on is a very strong signal.
You moved from investing alone as an angel to leading angel syndicate deals. What inspired that decision?
I didn’t actually set out to lead a syndicate. It happened almost deal by deal. The reason I did deal-by-deal syndicates was because, after I made a personal investment commitment to a founder, a couple of angels would reach out to me. They’d say, “Hey, I hear you’re investing. Can you tell me more about this founder?”
Since I already had the network with the team and I had either been part of a syndicate or had seen how it worked, I kind of knew how to structure it. We would prepare the papers, share them with a few other people, and that’s how I ended up leading a few deals.
Once you do something once, you learn how to do it better the next time, and it becomes easier.. Later, I also wanted to lead a syndicate that brought together investors from across the continent. And the reason for that was simple: If a company wanted to expand across Africa, it would be really helpful for them to already have angels from different countries on their cap table.
What’s the biggest operational or mindset shift when you’re investing your own capital versus when you’re guiding others to invest alongside you?
I think when you’re guiding others, you’re advocating for the deal—you’re championing it, and that’s actually how I learnt that being a partner at a VC fund is very similar: someone has to champion a deal internally too.
It’s very difficult for people to get excited about something they can’t immediately see or touch. In some of the products I worked on—like Sesame Street—you could see the Muppets and what they do. Or when I worked with a telco like Econet, you could feel and interact with the product. But when you’re investing early in a startup, it’s very esoteric. You have to help people envision what this could become.
So when you’re leading a syndicate, you’re almost another voice on behalf of the founder. You’re saying: “I see something here. I believe this team can pull this off. I’m putting my check in—and I think you should too.”
Then there’s the operational side. You have to figure out the right legal structure for the group, figure out who’s helping you lead and manage the syndicate because the founder can’t be sending updates to 20 different angels individually. Someone has to lead.
It’s also important to figure out who you want to co-lead with. In one of my deals, I had a co-lead with me; in another deal, there were two others.
Getting people to pay fees is another challenge. When you invest solo, you just wire your cheque and move on. But in a syndicate, there are legal fees and admin fees—there’s an extra cost that people have to be coordinated around.
You also have to think about things like how to handle disputes. For example, in one syndicate I led, someone had financial troubles and wanted to sell their stake. Managing that created a lot of additional administrative work. In one case, we managed to help them do a partial exit; in another, we couldn’t.
Also as a solo angel, you just write your cheque and interact when needed. But in a syndicate, people expect regular updates and transparency, and they expect you to have ongoing conversations with founders—even when it’s not always possible.
Honestly, leading a syndicate feels less like being an individual investor and more like running a mini-fund. It’s a lot more responsibility.
Have you been able to secure any exits, either through your personal angel investing or syndicate investing?
Yes. I’ve also been offered a partial exit in another deal, but I felt like we would be leaving too much money on the table to exit at that point. However, some of the angels that invested alongside me did take that offer.
I’ve also been offered secondaries—some I have seriously considered. I have exited two companies so far. In one, we got cash back. In the other, it was a share swap, so we now hold shares in a new, larger entity.
What type of startups do you gravitate towards nowadays?
I joined Delta 40 as a venture partner. It’s a climate tech and fintech-focused fund. What’s exciting for me is the intersection of climate tech, fintech, and AI. I think these areas will be truly transformative for the continent. They’re spaces where I wish we had even more traction as an ecosystem.
One sector I’ve always loved but haven’t been able to make an investment in is edtech. I’ve had a lot of conversations with edtech founders. I really love the space, but I think it’s a tough sector to deliver returns for investors. As an angel, you can stay in it for a long time, but as an institutional investor, it’s much harder. That doesn’t mean it’s not important—there are just so many challenges there.
Another area I believe is hugely under-represented is women’s health. Using technology to drive innovation in women’s health is a massive opportunity. I’d love to see more founders developing in that space, particularly solutions that are affordable and can deliver returns.
Sometimes, the sectors that have the most social impact also take much longer to produce investor returns. That’s where angel investors play a crucial role—we can provide patient capital. We definitely need more angel investors who are willing to do that.
I’m still super excited about fintech. There’s still a lot of friction in payments and cross-border transactions. Just the other day, I had international guests who couldn’t make a simple payment with their credit card at a restaurant. That’s still a problem, and it shows there’s still a lot of opportunity in fintech.
Climate tech is another major area. The price of diesel in Nigeria is changing the way people think about energy. We’re seeing so many new solar solutions. I believe we’ll continue to see real innovation in that space, and we’re already talking to many founders building there.
