When I first started my MBA, I knew I didn’t just want to study business — I wanted to be in it. In the mess, the momentum, the ambiguity. I wanted to earn relevance, not just read about it. The best way to do that, I figured, wasn’t to wait for an opportunity or beg for one at a happy hour. It was to ask for it.
So as a personal finance writer and LinkedIn fan, I reached out to the founder of a fintech startup: Plenty, a wealth management app for couples. I didn’t know exactly how I could contribute, but I had a strong curiosity for this space, a bias toward action, entrepreneurial experience, and opportunity to shape a new product.
Fast forward about a year later, Plenty was acquired by Wealthsimple in April 2025. But the most valuable part of the experience wasn’t the most exciting moments — it was what I learned by stepping into a fast-moving startup and figuring out how to build and scale our value in real time.
The Power of a Cold Message
Most of the meaningful opportunities in my career so far haven’t come through polished channels. They’ve come from genuine curiosity and direct outreach. Cold messages are underrated — and often misunderstood here.
You’re not asking for a job. You’re starting a conversation.
With a startup like Plenty, I didn’t wait for an opportunity or wonder if I was qualified. I reached out, shared why I cared about what their product , and asked how I could help. I had written hundreds of articles on personal finance, built a strong LinkedIn audience that spoke for itself, all while working full-time in big tech and pursuing my MBA part-time.
I’ve learned that knowing what you want often starts with knowing the value you already bring to the table.
That led to a few calls. Then a small project then a broader role in strategy and marketing. I didn’t walk into a defined position — I grew into it by asking the right questions and showing I could deliver.
There’s something powerful about betting on yourself, especially when you don’t have all the answers yet.
Finding My Place in the Chaos
Startups aren’t neat. There’s no manual, no perfectly scoped role, no roadmap with guaranteed outcomes. But that’s exactly why they’re such fertile ground for growth.
At Plenty, I jumped into marketing, content, and go-to-market strategy. I helped define the brand voice — moving away from feature-heavy messaging and toward emotional storytelling. Couples don’t want another budgeting app. They want to feel aligned. They want peace of mind. That insight drove how we positioned ourselves, how we create content, and how we built trust.
From there, I moved into marketing experiments and strategy, working closely with the founder to surface user insights, prioritize initiatives, and build what actually mattered.
There was no playbook I stepped into — but that was the point. The value came from helping build one, and that experience ultimately led me to my current role at a new startup, Inspirr, where we’re democratizing access to venture capital by investing in people as the asset.
5 Real-World Takeaways
1. You Don’t Need a Title to Be Valuable
Startups reward momentum. No one’s going to hand you a roadmap. You create value by identifying problems, taking ownership, and executing before being asked. That mindset — “How can I make this better right now?” — will serve you anywhere.
2. Marketing Is Human Psychology, Not Just Tactics
When we reframed our messaging from “track your expenses” to “build your future together,” engagement improved dramatically. People saw themselves in the story. Good marketing doesn’t just explain the product — it reflects the customer’s aspirations and anxieties.
3. Strategic Thinking Is Mostly Just Clear Thinking
Strategy isn’t about complexity — it’s about clarity. I learned to filter noise, prioritize what moved the needle, and have the discipline to say no to good ideas so we could focus on the great ones.
4. Speed > Perfection (If You’re Paying Attention)
We didn’t have the luxury of long planning cycles. We worked fast, tested everything, and iterated based on the market and sentiment of our audience. Speed matters — but only if you’re listening closely and adapting quickly.
Startups stretch you. They force you to do things you’ve never done before, with more ambiguity than structure. That’s exactly the point. You learn by doing, not by theorizing. You learn by failing fast, solving real problems, and collaborating with people who are too busy building to waste time on fluff.
I joined these startups not knowing what I’d end up working on — and ended up contributing to brand strategy, marketing initiatives, community engagement, user insights, and more. It was uncomfortable at times. And that’s how I know it was valuable.
Final Thought: Never Hurts to Ask
Whether you’re an MBA student, a career switcher, or just an aspiring entrepreneur — don’t wait to be handed the next opportunity. Reach out. Show up curious. Offer to help.
Sometimes all it takes is one thoughtful message to unlock the experience, growth, and confidence you’re looking for.
Because the best way to gain relevance… is to create it.