30 Conversations | Conversation #1 | The Lawyer Mindset

30 Conversations | Conversation #1 | The Lawyer Mindset

 

This week, I had the privilege of sitting down with Teslim Ogundiran, Investor at BDC, as part of my 30 Conversations project—a personal research initiative exploring the intersection of finance, strategy, venture capital, commercial law, innovation, and leadership.

One of the reasons I was particularly excited for this conversation was Teslim\’s academic background in law and working experience in finance. His shift from law to finance offered a perspective I hadn\’t yet explored in this project.

A little about Teslim Ogundiran

Teslim is trained in law, but is anything but a lawyer. During his academic journey, he quickly learned that law was not for him after his first internship, which led him to pivot into finance. Rather than viewing that experience as a detour, he leveraged the skills and mindset he developed through legal training to build a successful career in finance.

His story reminded me that our greatest competitive advantage often comes from combining experiences that, at first glance, seem unrelated.

Three ideas that challenged my thinking

1. More alike than I thought

Before this conversation, I viewed venture capital and commercial law as two very different professions. Teslim helped me see the overlap.

Both require strong risk management, attention to detail, critical thinking, relationship building, and the ability to navigate ambiguity. The best investors aren\’t just financially strong—they also possess commercial judgment, humility, curiosity, and an eagerness to learn.

Reflection: Sometimes the most valuable skills aren\’t industry-specific—they\’re transferable across disciplines.

2. It goes beyond numbers

Financial models and spreadsheets are essential, but they don\’t tell the whole story.

Investing requires understanding the people behind the business just as much as the business itself. It\’s about evaluating character, leadership, resilience, and vision alongside financial performance.

Reflection: Strong investors read both financial statements and people.

3. You win some, and you lose many. But when you win, you win big

One insight that stood out was the reality that many investments won\’t succeed—and that\’s expected.

Success isn\’t about avoiding failure altogether; it\’s about learning from each investment, maintaining a long-term perspective, and building a portfolio where the winners more than offset the losses. We also discussed the importance of creating strategic synergies across investments rather than evaluating each opportunity in isolation.

Reflection: Long-term thinking is often the greatest competitive advantage.

My biggest takeaway

Every conversation in this project has reinforced that careers are rarely linear, but they are intentional.

The lesson I\’ll be taking with me from this conversation is:

Your unique experiences become your competitive advantage when you learn how to connect them.

That idea has changed the way I\’m thinking about graduate school and positioning myself in the marketplace.

How I\’m applying this

Learning only matters if it changes how we think or act.

After this conversation, I\’m committing to:

 

• • Better understanding what truly makes me different.

• • Identifying how my experiences across finance, entrepreneurship, leadership, and strategy complement one another.

• • Embracing future pivots as opportunities to build, rather than dilute, my career story.

I\’m excited to see how these small changes shape my own career journey.

A thank you

Thank you, Teslim Ogundiran, for your generosity, openness, and willingness to share your experiences. I truly appreciate your time and the wisdom you shared. Conversations like these remind me how generous people can be when it comes to helping others grow.

Help me reach 30 conversations

This is Conversation #1 of 30.

My goal is to speak with professionals across:

• M&A & Corporate Law
• Venture Capital
• Investment Banking
• Corporate Development
• Corporate Strategy
• Innovation & Entrepreneurship
• Family Offices
• Economic Development

If you work in one of these areas or know someone whose perspective would add to this project—I would love an introduction.

My hope is that these conversations not only shape my own career decisions but also provide valuable insights for anyone exploring a future in business, finance, law, strategy, or innovation.

Who do you think I should speak with next?

#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MandA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship

One conversation down. Twenty-nine more opportunities to learn.