From 9–5 to Living on My Terms | Tech, Finance & Entrepreneurship with Tobi Adekeye

Tobi Adekeye, former Shopify Product Manager, shares her immigrant journey on The Immigrant Story. Learn how to transition from a 9-5, build wealth through real estate and investing, and create a life of freedom and impact.

In this episode of The Immigrant Story, we sit down with Tobi Adekeye—a former Shopify Product Manager, licensed Realtor, and the founder and host of the Wealth on Your Terms podcast. Tobi shares her inspiring journey of leaving the traditional 9-5 to build a life defined by freedom, strategy, and impact.

From her extensive work in tech, finance, and entrepreneurship, Tobi brings powerful insights and untold stories that challenge the way we think about building wealth and creating opportunities. This conversation is a masterclass for any immigrant aiming to thrive, not just survive.

From Aerospace to Adult Gap Year: The Strategic Pivot

Tobi’s journey is a testament to strategic thinking. After studying aerospace engineering, she graduated into the uncertain job market of 2020. She quickly realized that her chosen field was too niche, limiting her location and long-term earning potential.

Her pivot into tech, specifically landing a coveted role as a Product Manager at Shopify, was driven by a desire for greater financial upside and a more dynamic work culture.

Overcoming the Immigrant’s Fear of Transition

For immigrants, career changes are often fraught with fear, especially when tied to visa status. Tobi was securing her Permanent Residence (PR) when she decided to make the leap. Her strategy was to “lean into the fear” and operate with the mantra, “do it afraid.”

She mitigated risk by knowing she could return to engineering if needed, using it as a stability plan while she pursued her ambition in tech.

The “Adult Gap Year”: Redefining Success After Securing Stability

A defining moment in Tobi’s story is her decision to take an “adult gap year.” This wasn’t a lapse in judgment but a calculated move made possible by a crucial mindset shift that many immigrants experience.

“Something switched in my brain once I got my permanent residence… In the beginning, you think about safety. Once that’s secured, you actually now need to start taking risks.”

She used this time to rest, regulate her nervous system, and strategically plan her next chapter based on new information and self-awareness, free from the “Sunday scaries.”

Wealth on Your Terms: A Mission to Demystify Finance

Tobi’s passion for financial education led her to start the “Wealth on Your Terms” podcast. The mission is to provide access to information often kept within closed circles, focusing on the intersection of tech, finance, entrepreneurship, and culture.

“Representation matters… I want to share stories that challenge the way we think about building wealth.”

The podcast explores diverse wealth-building paths—from high-income careers and entrepreneurship to real estate and the stock market—emphasizing that there is no one-size-fits-all approach.

A Costly Early Financial Mistake

Tobi shared a common immigrant financial mistake: sending savings back home to invest in local currency. When the currency devalued and she needed to transfer funds back to Canada, she lost a significant amount.

Her advice:

Educate yourself on investment vehicles in your new country first.
Only put money in your home currency that you plan to spend there.

From Survival to Thriving: A Blueprint for Immigrants

Many immigrants get stuck in survival mode. Tobi provided a clear framework to break this cycle.

1. Set a Timeline for Survival Mode

Don’t let it become permanent. Set an aggressive but reasonable timeline (e.g., 9 months) to push yourself into the next phase.

2. Strategic Networking: Lateral vs. Vertical

Lateral Networking: Connecting with peers in a similar situation for support.
Vertical Networking: Connecting with those who have already “made it.” This provides a vision for what’s possible and opens doors.

3. Manage “Black Tax” with Boundaries

While supporting family is important, your survival comes first.

Be strict by allocating a fixed percentage of your income.
Empower family members through education instead of creating dependency.

Is Real Estate the Ultimate Wealth Pillar?

As a realtor, Tobi offers a contrarian, data-driven view: real estate is not for everyone.

Her foundational advice is to focus on increasing your income first. A higher income makes real estate risks more manageable.

Her investment hierarchy for immigrants:

Become Financially Literate: Understand budgeting and opportunity cost.
Start with the Stock Market: It has a lower barrier to entry and teaches you about risk.
Then Consider Real Estate: Only after you are financially educated should you consider investing large sums.

A Call to Action: Dream Bigger and Collaborate

Tobi’s final message is a powerful call for the immigrant community to elevate its ambitions through collaboration.

“I want to see more immigrants owning things… It makes it easier for new immigrants that come in. It gives them a softer landing.”

She urges a shift from an individualistic mindset to one of collaboration—pooling resources to buy businesses, invest, and create opportunities that uplift the entire community.

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