30 Conversations | Conversation #10 | Reculer pour mieux sauter
What if moving forward doesn’t always mean moving faster?
This week, I had the privilege of sitting down with Ayo Aiyeleye, Executive Director, Entrepreneurial Capital at Alberta Innovates, as part of my 30 Conversations project—a personal research initiative exploring the intersection of finance, strategy, venture capital, commercial law, innovation, and leadership.
I was particularly excited for this conversation because Ayo’s career has taken him through several different parts of the financial ecosystem, including investment banking, stock exchanges, commercial banking, and capital deployment.
His journey offered a perspective I hadn’t yet explored in this project:
What can happen when you learn to understand capital from multiple angles?
A little about Ayo
Ayo loves money—not necessarily to spend it or save it, but to understand how it moves, how it changes, and how it influences.
His career didn’t begin in finance.
He initially set out to become an aeronautical engineer, but by his third year of university, he began questioning whether science was where he wanted to build his career. An internship at an insurance company became an unexpected inflection point.
From there, his career would take him through different parts of the financial system, eventually leading to his current work in entrepreneurial capital.
And throughout our conversation, I kept coming back to two ideas:
“An object in motion stays in motion.”
And the French expression:
Reculer pour mieux sauter — sometimes you have to step back to jump further.
Three ideas that challenged my thinking
💡 1. Sometimes you have to slow down to speed up.
When Ayo first arrived in Canada, he had his sights set on the Toronto Stock Exchange. With experience in investment banking, stock exchanges, and commercial banking, he expected his previous experience to translate more directly into the Canadian financial ecosystem.
It didn’t.
Instead, he found himself working at the CRA call centre as a business advisor.
Not exactly the trajectory he had imagined.
But rather than treating the role as a detour, he used it as an opportunity to understand how businesses and the financial system operated in Canada. He eventually pursued an accounting diploma as another way to deepen that knowledge.
What looked like a step backwards became a training ground.
And that made me rethink what “moving forward” actually means.
Sometimes progression isn’t about getting the next title, salary, or position.
Sometimes it’s about building the knowledge, context, or perspective you didn’t know you were missing.
Reflection:
I think we can become so focused on momentum that we forget that momentum without direction isn’t necessarily progress.
Maybe there are moments in our careers when the right move isn’t to accelerate—but to reposition.
💡 2. Approach opportunities like an analyst.
One question Ayo shared from the world of capital deployment really stuck with me:
“Is there any reason why we shouldn’t invest?”
Behind that question is an entire process of research, analysis, risk assessment, and due diligence.
An analyst isn’t simply looking for reasons to say yes. They’re looking for the information that helps determine whether the opportunity makes sense.
And I started wondering:
What would happen if we approached our own opportunities this way?
When we’re considering a new role, business idea, academic path, relationship, move, or risk, we often ask:
“Why should I do this?”
But what if we also asked:
“Is there any reason why I shouldn’t?”
What information am I missing?
What risks am I overlooking?
What assumptions am I making?
What would make this a bad investment of my time, energy, or resources?
That doesn’t mean saying yes to everything.
It means replacing fear with due diligence.
Reflection:
Maybe some opportunities don’t need more signs telling us to go.
Maybe they need better questions.
💡 3. Follow the money—but don’t forget the people.
One of the recurring themes in Ayo’s career has been understanding where capital is moving and what those movements reveal about the broader economy.
Technology changes. Markets change. Industries change. Consumer behaviour changes.
There isn’t a shortcut for knowing exactly what comes next.
But there is a way to stay curious about it:
Keep learning. Study the market. Follow the money.
What I found equally interesting was his emphasis on relationships.
Expertise can create opportunities, but relationships and stakeholder management can determine what happens once you’re in the room.
When I asked what he would focus on if he were starting again at 25, his answer centred around three things:
Build relationships.
Carve out your niche.
Study the market.
That combination really stayed with me.
Because understanding where the world is going is one thing.
Understanding where you fit into it is another.
Reflection:
I’m increasingly realizing that career development isn’t just about becoming more qualified.
It’s about becoming more useful—to the right problems, in the right environments, at the right time.
My biggest takeaway
Every conversation in this project has reinforced that careers are rarely linear—but they can be intentional.
Ayo’s conversation left me with one question:
“Is there any reason why we shouldn’t…?”
Not as an excuse to take every risk.
But as an invitation to investigate the risks standing between me and an opportunity.
Instead of waiting for certainty before moving, I want to become better at doing the research, understanding the downside, learning from the information available, and making an informed decision.
Maybe the goal isn’t to eliminate risk.
Maybe it’s to become better at understanding it.
How I’m applying this
Learning only matters if it changes how we think or act.
Because of this conversation, I’m going to:
- Take strategic steps back when I need more knowledge or perspective—not automatically interpret them as failure or regression.
- Approach opportunities like an analyst by asking better questions, understanding risk, and doing the due diligence.
- Build relationships intentionally rather than treating networking as something separate from career development.
- Pay attention to where capital and opportunity are moving so I can better understand where I can create value.
A thank you
Thank you, Ayo, for your generosity, openness, and willingness to share your experiences.
I especially appreciate the way you connected the technical world of finance and capital deployment to the much broader questions of career development, relationships, learning, and opportunity.
Conversations like this are exactly why I started this project.
Help me reach 30 conversations
Conversation #10 of 30.
A third of the way there!
Thank you to everyone who has offered their time, connected me with someone, followed along, or simply supported this project so far.
I’m speaking with professionals across:
- M&A, Corporate & Commercial Law
- Venture Capital, Investing & Private Capital
- Investment Banking & Capital Markets
- Corporate Development & Strategy
- Innovation, Entrepreneurship & Strategic Partnerships
I’m also exploring perspectives across family offices, corporate venture capital, economic development, higher education & innovation, luxury/consumer strategy, media, entertainment, tourism, founder success, and business design.
The goal isn’t simply to understand what people do—but how they build careers, navigate change, recognize opportunities, and create meaningful value.
If you work in one of these areas—or know someone whose perspective would add something meaningful to this project—I would love an introduction.
Every conversation is helping me better understand how organizations and individuals create value through capital, strategy, governance, relationships, and innovation.
And hopefully, these reflections are useful to others asking some of the same questions.
Who do you think I should speak with next?
One-third down. Twenty more opportunities to learn.
#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MAndA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship
