If you’re reading this, chances are you’re interested in financial literacy, already an investor, or thinking about getting started. My name is Taavi Ilves, and my investment journey began in 2014 with a portfolio worth exactly zero. Fast forward to today, and my portfolio has grown to nearly half a million euros.
But how did I get here? Let me take you through my story—from my first side projects to my investing strategies and biggest lessons learned along the way.
From Early Tech Enthusiast to Investor
I’ve always been passionate about technology. My career in IT started early—I was coding by the time I was 16, and by the end of high school, I had developed a social networking platform that gained 30,000 users, with some even becoming paying customers.
My professional journey led me to work in various tech companies, and today, I work four days a week as a software engineer at Bigbank. The rest of my time? I dedicate it to my family, hobbies, and of course—investing.
Since 2014, I have tracked every income, expense, and investment decision I’ve made. Every month, I analyze my numbers with enthusiasm because, honestly, I love spreadsheets, charts, and financial data.
How I Found My Way to Investing
While I started actively investing in 2014, my first exposure to the stock market happened earlier. I remember being in military service in 2010, placing a sell order for Tallinn Vesi stock at night, hoping it would be executed by morning.
The real turning point came when I read Jaak Roosaare’s book, “How to Get Rich”, and attended one of his first investing workshops. Fun fact: That event also led to the creation of the now well-known Financial Freedom Facebook group, which has since connected thousands of investors.
Why Investing, Not Just Spending?
At that time, I was a university student working part-time, receiving scholarships, and living a modest lifestyle—sharing an apartment with fellow students. This meant I had extra money left over every month.
I realized that instead of letting it sit in my bank account, I could put my money to work and make it grow.
At around the €20,000-€30,000 portfolio mark, I had an “aha moment”—I no longer needed to stress about money. I understood that if I continued growing my income and making smart investment decisions, my portfolio would keep expanding, and I could focus my energy on self-development rather than financial worries.
The Turning Point: Growth Through Community
Starting my investment blog and sharing insights on Facebook connected me with other investors. Some were just starting out, while others were already far ahead of me.
Attending conferences, investment club events, and workshops helped me meet people like Kristi Saare, Tauri Alas, and Kristjan Liivamägi. Eventually, we formed a private investment group that has now grown into a 12-person mastermind, including some of Estonia’s most prominent financial influencers and investors.
This group has been invaluable—a fast track for both knowledge and portfolio growth.
My Portfolio Today
My investing philosophy has always been about building a diversified and liquid portfolio so I can adjust asset allocations based on market cycles.
Here’s how my portfolio looked in early 2023:
- 40% – Stocks
- 23% – Loans & Bonds
- 22% – Startups
- 9% – Cash
- 5% – Private Companies
- 1% – Crypto
Unlike many investors, I don’t currently own real estate, as I prefer flexibility and liquidity. My portfolio has evolved significantly over time—from focusing on loans in the beginning to a much larger share in stocks and startups today.
Biggest Lessons Learned
Start Now – Take the first step by saving, then the next by investing. The sooner you start, the better.
Keep Learning – Read books, blogs, and case studies. Learn from other investors’ successes and mistakes—but also from your own experiences.
Surround Yourself with Like-Minded People – If your current circle doesn’t support your financial goals, find a community of ambitious, finance-savvy people. You’ll progress faster together.
Ask Questions – You’d be surprised how willing experienced investors are to share knowledge when approached the right way.
Take Calculated Risks – Whether in investing or life, risk and reward go hand in hand. Understand risk management and make informed decisions.
Set Goals – Define clear financial and investment goals with milestones and action steps. Writing them down increases your chances of success.
Increase Your Income – Whether by climbing the career ladder, negotiating better salaries, switching jobs, or even starting a business—higher earnings accelerate portfolio growth.
Why I Started Sharing My Journey
Together with Marko, I launched Off The Record (OTR) to provide more value to the investment community—raw, unfiltered, and numbers-based insights.
We wanted to create high-quality investing content, free from unnecessary fluff. While we could share everything on personal blogs, a closed platform allows deeper discussions without unwanted distractions.
Our goal? Building a real investing community—where people can exchange ideas, ask questions, and learn from each other.
