Somewhere right now, a founder who raised a decent round, built a real product, and had people genuinely rooting for them is in the middle of making a decision that is going to age very badly. They do not know it yet. And the people who were supposed to know it are nowhere to be found.
I have watched this story play out enough times that the shape of it has become familiar. Smart person, good company, real momentum, and then something completely avoidable blows it all up. There is even a running joke in venture circles that landing on Forbes 30 Under 30 is really a jail sentence waiting to happen. Obviously that is an exaggeration, most people on that list worked hard and deserve to be there. But the joke has survived long enough to mean something.
The question I keep coming back to is why these founders mess up, and where everyone who was supposed to be in their corner was when it mattered.
When I reflect on my own career, from being a young person still figuring out how professional environments worked, to eventually sitting on boards myself, one pattern keeps coming back to me. Many of us who occupy board seats are actively failing the founders we are supposed to be leading. By no means are we incompetent in our own fields, we have sadly redefined the role into something much smaller than it is supposed to be.
The board is the adult in the room
There is a formal answer for why companies have boards. Fiduciary responsibility, shareholder oversight, strategic guidance, all of that exists and matters. But underneath the governance language, a board is also meant to be a room full of people who have already made the expensive mistakes and are in a position to help the people in front of them avoid repeating the same ones. That part seems to have secretly been dropped from the job description.
I know what a board can do for a person’s development because it happened to me, and I can trace almost every meaningful thing I understand about leadership back to specific people and specific rooms.
The first time I found myself on a board that carried real weight was at SystemSpecs, right after returning from Dubai. I walked into a room with Christopher Kolade and Ernest Ndukwe, the man who effectively delivered telecoms to Nigeria at a time when every other infrastructure effort was crumbling under its own weight. These were not accomplished people in the conventional sense alone. They were men whose names meant something, whose conduct meant something, who had clearly decided long ago what kind of people they were going to be and held to it ever since.
Nobody lectured me or handed me a manual. But as I sat in that room, my brain just reset itself. Because when I was in banking, my idea of team bonding involved taking my colleagues to places I absolutely cannot describe in writing. That version of me was not compatible with the room I had entered, and I knew it without being told. The presence of people I deeply respected did the work that no training program ever could. Nobody needed to catch me being careless, because the thought of it was already unbearable.
What I learned, and from whom
From SystemSpecs I moved on to start Trium, the corporate venture arm of the Coronation Group, and went back to work with my former boss, Aigboje Aig-Imokhuede. When I was eventually leaving after four years, I told him he needed to formally issue me a PhD certificate, because what I received during that period was more rigorous than most structured programs could have delivered. And I was not the only one who benefited from being in that orbit. The board around Aigboje was its own institution.
Segun Ogbonlowo was the first person who ever showed me what it looked like to carry oneself properly in a boardroom. Early on, I was in a meeting with Aigboje and I was making my case for something, probably with more confidence than I had earned at the time, and Segun pulled me aside afterward, pulled my ears like an errant school child. He walked me through how a board member is supposed to conduct themselves with their chairman, how you prepare ahead of a meeting, how you listen before you push, how the room functions when everyone is playing their role well. It was direct, private and it changed how I showed up from that point forward.
Bunmi Lawson did something different for me. She laid the foundation of how I think about risk and compliance, in a way that was practical and grounded rather than theoretical. That understanding has traveled with me to every seat I have held since, and I still draw from it more than she probably knows.
What Aigboje himself gave me is harder to compress. It was exposure, full stop. He took me to meetings with the Vice President. He brought me into rooms with the SEC. He let me watch how a person of his standing navigates high-stakes environments, which turned out to be a long and irreplaceable masterclass in how power, preparation, and restraint work in combination. My ability to engage at senior levels on something like open banking did not come from reading about it but came from standing in those rooms and paying close attention.
Paying it forward, one board room at a time
When I was involved in setting up the board for TeamApt, which most people now know as Moniepoint, I tried to apply what I had absorbed. We brought in Professor Yinka David-West, Chidi Okpala, and Boye Ademola from KPMG. At the time, people seemed to think I was working from some careful, deliberate framework. Mostly I was translating what Aigboje and others had given me into a new context and hoping it would hold. It did, and watching that board find its footing confirmed something I had already begun to suspect.
I saw this up close at Paystack recently, when one of the bright people there was stepping away. When they called me, they spent a good portion of that conversation talking about their experience working with me and how it made them sit up. When I think about the time I have spent on the Paystack board alongside people I respect enormously, and when I hear from those inside the company about what it has meant to work with board members who genuinely show up for them, it confirms the same thing.
Now, Paystack is already heads and shoulders above most African fintechs. But what that conversation showed me is how much what we bring to a board room, myself and the other board members I deeply respect there, matters. We navigated extremely difficult times together, and I believe some of what we built, the decisions, the process, the discipline, will end up becoming playbooks taught in MBA classes somewhere down the line.
Too many board members have made peace with doing the minimum
Too many board members have turned their role into a supervisory checkbox. They arrive for quarterly meetings, review decks, approve budgets, and leave. That is compliance cosplaying as leadership, and it leaves out entirely any real investment in the human being sitting across the table. That gap is where founders eventually get into trouble.
Founders, especially first-time founders, are often technically brilliant. They understand their product, their market, their users. What they frequently do not have is the kind of institutional wisdom that only comes from navigating complex organizations over time, from making expensive interpersonal mistakes and surviving them, from watching how seasoned leaders carry pressure without letting it crack their judgment. That wisdom is not available online. It lives in the people around them, specifically in the people on their board, and when those people are not actively transferring it, the founder learns it the hard way. Sometimes very publicly.
This is also not a problem that belongs only to early-stage companies. Governance failures and leadership implosions happen at every stage of growth and in every market. WeWork burned through billions with a board that watched Adam Neumann operate like a one-man religion and said nothing useful until the IPO was already on fire. Theranos had a board full of decorated names who apparently never thought to ask whether the machine actually worked. The geography and the industry keep changing but the shape of the failure stays the same. What matters is whether the people in oversight positions are actually doing the work, or collecting fees and updating their profiles.
Who you put in that room is a decision you will live with
If you are an investor and you place people on a board primarily to protect your equity and represent your interests, you are doing just a measly 10% of the job. The people you send into that room need genuine experience, real standing in the market, and the willingness to do the unglamorous work of developing the people they are serving.
A founder with nobody in their corner doing real mentorship will eventually make a decision that costs everyone. Maybe it is a regulatory misstep or a culture failure that becomes a public mess. Perhaps it is a board blowup that turns into a cautionary story told at panels for years. These things happen on a predictable schedule at companies whose leadership has not been adequately developed, and the investors who placed inadequate board members into those seats share the outcome whether they acknowledge it or not.
The compounding benefit of doing this well is equally real. Founders who receive genuine development grow into leaders who can eventually sit on someone else’s board, contribute meaningfully, and extend the same investment to the next generation of people coming up.
Mentorship on a board should be mandatory
One-on-ones between board members and founders should be standard practice. Mentorship with specific developmental intent should be part of how a board operates, not an afterthought nobody budgets time for. Where a board does not have the bandwidth to do this internally, it should actively mandate that the company bring in executive coaches or external mentors who can fill the gap. For a founder navigating the role for the first time, that kind of support is infrastructure, and treating it as optional is how you end up reading about them in a forwarded article six months later.
The downstream effects of getting this right show up in measurable ways. Organizational drama decreases, distractions thin out, board meetings become more productive because the people presenting have been developed well enough to hold the room properly. Reports arrive in better shape and investors deal with fewer surprises. The whole system runs cleaner, and the money is considerably safer.
The inverse is equally predictable. If you are on a board right now and you are not doing this work, you are managing a countdown. The founder may be technically sound and working hard, but experience cannot be improvised under pressure, and at some point, that gap will surface in a way that is difficult to reverse after the fact.
I owe everything I understand about how to carry myself in positions of leadership to people who chose to invest in me when it would have been far easier to let me find my own way. Aigboje Aig-Imokhuede deserves the most credit for that, without any qualification. I also owe a great deal to Segun Ogbonlowo, Bunmi Lawson, Christopher Kolade, and Ernest Ndukwe, each of whom gave me standards worth keeping, through direct intervention or through the simple example of how they showed up. I hope I never get to disgrace any of them.
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