Last Updated on 13/02/2025 by Carl-Peter Lehmann
As a financial advisor and wealth manager, it’s not necessarily in my interests to encourage DIY investing – after all, professional financial advice exists for a reason. However, I also recognize that many people choose to take control of their own investments, whether out of interest, cost considerations, or a belief in their own ability to manage their portfolios effectively. Given this reality, it’s worth exploring both the opportunities and challenges of DIY investing, particulary DIY Share or Stock Investing.
DIY investing can take several forms, depending on how hands-on an investor wants to be. At the simpler end, it involves selecting unitized funds – either actively managed or passive index-tracking ETFs – allowing investors to take control of their portfolio construction while still benefiting from professional fund management. A step further is directly selecting individual securities such as shares and bonds, where investors take full responsibility for research, allocation, and risk management. Many adopt a hybrid approach, using funds for broad diversification while holding individual securities to capture specific opportunities.
The rise of DIY investing has been fueled by the democratization of information and the increasing accessibility of investment platforms. It has never been easier – or cheaper – to invest directly, with vast resources available to help individuals make informed decisions. However, with this opportunity comes responsibility. Successful DIY investing requires discipline, emotional control, and the ability to filter vast amounts of information to make sound, long-term decisions.
My Journey as a DIY Investor: From Unit Trusts to a Global Offshore Share Portfolio
About ten years ago, I made a significant pivot in my investment approach. Rather than continuing with unitized funds—whether actively managed or index-based ETFs – I decided to invest in shares directly. Somewhat arrogantly (and probably naively), I believed I could achieve better results myself than through professionally managed funds. At the same time, I moved all my discretionary life savings offshore, shifting my focus toward building a globally diversified offshore share portfolio (as a South African for obvious reasons). I set my benchmark against the S&P 500, using it as my yardstick to measure performance and hold myself accountable.
Thankfully, the results have been pretty good. Not only have I been able to ‘outperform’ the S&P500 (which as we know very few professionally managed funds do), but I’ve also built a portfolio that suits me – one that aligns with my needs, risk appetite, and long-term financial goals. Managing my own investments has given me a level of control and flexibility that I wouldn’t have had otherwise, and if all goes well, this approach should get me to where I want to be, faster. That said, DIY investing isn’t without its challenges. It requires ongoing learning, emotional discipline, and a willingness to accept that mistakes will be made along the way. But for those willing to put in the effort, it can be an incredibly rewarding way to invest.
The Pros and Cons of Professional Asset Management
There’s no denying that the professional asset management industry is filled with exceptionally smart people. You don’t get a job at a top asset manager today unless you’re highly intelligent, well-educated, and analytically sharp. Fund managers have access to vast resources, sophisticated research tools, and teams of analysts dedicated to dissecting markets and identifying opportunities. Theoretically, this should give them a clear edge over individual investors.
The Downside of the Asset Management Industry
However, the democratization of information and the ease of investing have significantly eroded the advantage that professional fund managers once held. Decades ago, asset managers had privileged access to data, company management teams, and in-depth market intelligence that wasn’t readily available to the average investor. Today, much of that information is in the public domain. Retail investors have access to company filings, earnings calls, professional-grade research, and real-time market data at the click of a button. As a result, the traditional information asymmetry that once favored professionals no longer applies in the same way.
Despite their intelligence and resources, professional fund managers face a harsh reality – investing is an incredibly tough job, and results are ultimately binary. Either you outperform or you don’t. And statistics consistently show that very few active managers are able to outperform their benchmarks over long periods. Even among those who do, the persistence of outperformance is rare. The structural challenges of managing large pools of money, dealing with inflows and outflows, and maintaining career risk considerations mean that many fund managers struggle to take the same high-conviction bets that a DIY investor can for example.
The Pros of Professional Fund Management
That being said, professional asset management still has clear advantages, particularly for investors who lack the time, interest, or expertise to manage their own portfolios. A well-chosen fund manager can provide disciplined risk management, rigorous research, and the benefit of experience navigating complex market environments. The challenge is identifying those rare managers who can genuinely add value – rather than simply charging high fees for index-like returns (or worse).
Ultimately, while professional fund management plays a vital role in the investment ecosystem, it’s no longer the only path to success. For those willing to take on the responsibility, DIY investing can offer a viable alternative – one that provides control, flexibility, and the potential for strong long-term results
Why I Chose to Invest in Shares Directly
One of the biggest reasons I shifted to directly investing in shares was the ability to build a portfolio exactly how I want it. Unlike a fund manager constrained by mandates, liquidity requirements, or career risk, I can invest in companies that may not be on the radar of professional portfolio managers – either because they’re too small, too niche, or don’t fit within a predefined investment style. This gives me the flexibility to back businesses I truly believe in, rather than being limited to what’s in favor at any given time.
Beyond that, there’s the obvious appeal of greater control and cost savings. By eliminating the fees associated with actively managed funds, I can reinvest more of my returns over time. But perhaps one of the most underrated benefits of managing my own portfolio is how much it sharpens my understanding of investing as a whole. The asset management industry is filled with jargon, and it’s easy to be swayed by a compelling narrative or an impressive-looking chart that supports a fund manager’s view. Having firsthand experience picking stocks makes me far more critical in assessing what fund managers are actually doing, and whether they’re genuinely adding value.
At its core, investing is often more about common sense than the ability to build sophisticated discounted cash flow (DCF) models or apply complex quantitative techniques. Of course, professional investors have skills and tools that retail investors don’t, but the reality is that much of investing boils down to identifying good businesses, buying them at reasonable prices, and having the discipline to hold them for the long term. This is what makes stock investing unique – unlike most fields where professionals hold a near-insurmountable edge (whether it’s sports, medicine, or engineering), ordinary investors can and do outperform the professionals. It’s not easy, but it’s far from impossible.
Further Reading: 15 Key Investment Principles to Increase Your Odds of Success
How I Think About Portfolio Construction
One of the hardest parts of managing a portfolio isn’t necessarily deciding what to buy – it’s figuring out how much to allocate to each investment and understanding the role each company plays in the bigger picture. The best analogy I can think of is that building a stock portfolio is like constructing a sports team. In most team sports, you have defenders, midfielders, and attackers, each serving a different but complementary purpose. I think about my share portfolio in a similar way, where each investment has a defined role, though sometimes those roles overlap.
Defensive holdings are like the backbone of the team—the reliable players that provide stability and consistency. These are typically high-quality, blue-chip companies that generate strong cash flows, pay growing dividends, and have resilient business models. They can be found across various sectors, from consumer staples (like McDonald’s or Coca-Cola) to healthcare (such as Johnson & Johnson) to industrials (like Honeywell, Deere, or Rockwell Automation). Even certain tech companies, like Apple, can be considered defensive in today’s world, given their massive cash flows, entrenched market position, and pricing power.
Midfielders are the versatile players that help connect the defensive base with the attacking front line. Because I primarily view myself as a growth investor, my midfield tends to be composed of high-quality companies with a growth bias. Many of these are found in sectors like technology, communication services, financial services and healthcare—companies like Microsoft, Alphabet, Meta, Visa or Eli Lilly, which have strong growth potential but are also well-established enough to offer a degree of resilience. These stocks balance stability with upside potential, making them a key part of the portfolio’s overall composition.
Attackers (the current obvious play being the seminconductor ecosystem) are where I take more aggressive bets – high-growth (sometimes speculative) names that have the potential to shoot the lights out (or fail miserably). These are the stocks where I ask myself: Could this company 10X? They are typically found in emerging industries or disruptive sectors, where the growth runway is significant but comes with heightened risk. Whether it’s a fast-growing software company, a biotech innovator, or a next-generation clean energy firm, these are the players that can make a major impact—but only if they deliver.
By thinking about portfolio construction in this way, I aim to create a well-balanced team—one that can defend when needed, control the game in the middle, and capitalize on high-growth opportunities when the timing is right.
Position Sizing and Managing Risk
Beyond just selecting the right mix of stocks, position sizing is crucial in building a successful portfolio. How much capital I allocate to each investment is as important – if not more – than what I invest in. My approach to position sizing varies depending on whether a stock falls into my defensive, midfield, or attacker categories.
For defensive and midfield holdings, a full position is typically 5% (cost basis) of the portfolio. These are the companies I have the highest conviction in—businesses with strong fundamentals, competitive advantages, and the ability to compound over the long term. Generally, my strategy here is to let winners run. If a quality company is performing well and continues to execute, I don’t want to cut off its potential upside prematurely.
On the attacker side, position sizing is more conservative because these stocks come with higher risk. A full position here might range between 1% and 2.5%, depending on the company, its volatility, and the conviction I have in the investment case. These are the names where being disciplined about taking profits or cutting losses is essential – if the thesis doesn’t play out, it’s better to exit rather than hold on and hope for a turnaround.
Another key principle I follow is layering into a position rather than going all-in at once. Instead of buying a full 5% position in one go, I might scale in over three separate purchases, particularly in volatile or uncertain market conditions. This helps manage risk and allows me to take advantage of price fluctuations – buying more if the stock drops (provided my thesis is still intact) or adjusting my allocation as I gain more conviction.
This structured approach to position sizing ensures that my portfolio remains balanced—giving enough weight to my highest-conviction ideas while managing risk effectively in higher-growth, more speculative opportunities.
The Best and Worst Investments: A Rollercoaster Ride
Like any investor, I’ve had my share of big wins and horrible losses – some that make me feel like a genius, and others that make me wonder what I was thinking. The reality of investing is that you won’t always get it right, but as long as the winners outshine the losers, you’re in good shape. Here are a few highlights (and lowlights) from my investing journey.
The Big Winners
AMD – The Ultimate Turnaround Story
When I first bought AMD, it was a struggling semiconductor company hanging on for dear life at around $10 a share. It had a compelling turnaround story, but let’s be honest -turnarounds don’t always turn. Fortunately, this one did, and then some. I took some profits when it soared over $200 (a 20X return), but I’ve continued adding and trimming over the years as the company solidified itself as a real competitor to Intel and Nvidia. This one remains one of my best investments and an example of why sometimes, the underdog is worth betting on.
Microsoft – The Cloud Pivot Masterclass
I first picked up Microsoft at $60 when Satya Nadella was steering the ship away from its legacy Windows focus and toward cloud computing and data centers. It had all the ingredients of a great investment—strong fundamentals, a visionary CEO, and a business model shift that was just getting started. Watching it climb past $400 has been a masterclass in why backing great companies with durable growth drivers pays off in the long run.
Visa – The Cashless Revolution
Some companies don’t need to be exciting to be great investments—Visa is one of them. A pure quality compounder, I first bought it well under $100, and today it sits around $350. The business model is simple: more digital transactions, more revenue. It’s a tollbooth on global commerce, and as long as people keep swiping, tapping, and clicking, Visa keeps making money.
The Painful Losers
Of course, not every stock pick has been a masterpiece. I also got caught in the post-COVID high-flyer momentum trade for a while – luckily, position sizing kept the damage in check.
ROKU – The One That Got Away (and Then Came Right Back)
I first bought ROKU at about $60, then watched it go vertical, shooting up to almost $500. At that point, I was patting myself on the back for spotting a future streaming giant. Unfortunately, I then proceeded to watch it collapse all the way back down to where it started. Classic case of “should’ve sold at the top.” The business still has potential, but this one taught me a hard lesson about momentum stocks and taking profits when valuations start looking ridiculous.
FUBO – The Momentum Darling Turned Dumpster Fire
I bought FUBO around $25, watched it double to $50, and for a brief moment, I thought I had found the next great sports streaming play. Then reality hit. It dropped like a rock, I eventually sold in the high single digits, and it’s since sunk into the $1 range. This one was a pure lesson in hype vs. actual sustainable business models.
Boeing – A Wall Street Darling Turned Trainwreck
Boeing was once a core holding of mine, a classic blue-chip industrial with a long history of dominance. That was until their safety issues became headline news. After the first crash, I put a rare stop loss in place, and by the time the second crash happened, the stock fell through the floor. While I managed to minimize my losses, Boeing served as a reminder that even the most established companies can fall apart when leadership and execution go wrong.
Lessons Learned
Investing is full of ups and downs, but the key takeaway is this: winners need to run, losers need to be cut, and discipline is everything. Some of the best stocks I’ve held have been those I simply allowed to compound over time, while some of my biggest mistakes have been getting caught up in hype cycles. At the end of the day, it’s all about stacking the odds in your favor and playing the long game.
My 3 Biggest Investment Regrets
No investor gets everything right, and sometimes the biggest mistakes aren’t the bad investments—it’s the ones you didn’t make or the ones you bailed on too soon. If I had to pinpoint my top three investment regrets, they’d be Bitcoin, Nvidia, and Tesla.
Bitcoin – The One That Got Away
Like many investors, I heard about Bitcoin over a decade ago. I even considered buying some, if only as a speculative bet. But I never pulled the trigger—chalk it up to skepticism, a lack of understanding, or just the fact that at the time, it seemed more like a niche tech experiment than a real asset class. If I had thrown just a little money at it, the returns would have been life-changing. Instead, I watched from the sidelines as it went from a quirky internet currency to a mainstream financial asset.
Nvidia – The AI King I Should Have Held
I actually owned Nvidia back in 2018, well before the AI boom. But at the time, it was facing inventory issues, crypto-mining headwinds, and overall market uncertainty, and I let myself get scared out of my position. Fast forward to today, and Nvidia has become the defining company of the AI revolution, with its stock delivering astronomical gains. If only I had held on, I’d be sitting on a monster winner instead of just watching from the sidelines.
Tesla – The Wild Ride I Couldn’t Stay On
I’ve also been in and out of Tesla, buying shares around 2018, when the company was in one of its many “this could go to zero” moments. Between production delays, Elon Musk’s Twitter antics, and endless short-seller attacks, it felt like a company constantly on the edge of collapse. So, I exited. And then, of course, it went on to become one of the most valuable companies in the world, delivering one of the biggest stock runs in modern history. Hindsight is 20/20, but this was a classic case of underestimating the power of a visionary company with a cult-like following.
These three missed opportunities serve as a reminder that sometimes, the best investments aren’t just about getting in—they’re about having the conviction to stay in.
The Ultimate Investment Portolio: My Dream Team Stock Portfolio
If the market went into a 50%+ bear market and valuations weren’t an issue, this is the portfolio I’d love to build—a collection of best-in-class companies that reflect where I think the future is going. Given my bias toward growth and secular trends, it would be heavily weighted toward industries driving technological, healthcare, and industrial innovation, with a mix of defensive moats for balance.
This “dream team” portfolio isn’t just about picking great companies—it’s about assembling a portfolio with a strong foundation, high-growth potential, and resilience. Here are 25 names from the 100+ stocks I track that would make the cut in a market reset:
1. Microsoft (MSFT) – AI, cloud dominance, enterprise software juggernaut
2. Google (GOOGL) – AI, search, digital advertising, cloud expansion
3. Visa (V) – Cashless payments, a tollbooth on global commerce
4. Nvidia (NVDA) – AI and GPU king, essential for the next wave of computing
5. Tesla (TSLA) – EV, energy storage, self-driving, humanoid robots
6. Eli Lilly (LLY) – A leader in diabetes, weight loss, and biotech innovation
7. Intuitive Surgical (ISRG) – Robotic surgery pioneer, the future of healthcare
8. Stryker (SYK) – Orthopedics and medical technology, a healthcare staple
9. TSMC (TSM) – The world’s most advanced semiconductor manufacturer
10. Rockwell Automation (ROK) – Industrial automation and smart manufacturing
11. Caterpillar (CAT) – A core infrastructure and construction play
12. Deere (DE) – The future of precision agriculture and automation
13. Lockheed Martin (LMT) – Defense and aerospace leader, geopolitical hedge
14. LVMH (LVMUY) – The ultimate luxury brand powerhouse
15. S&P Global (SPGI) – Data, analytics, and financial intelligence
16. The Trade Desk (TTD) – Programmatic advertising and digital media shift
17. Broadcom (AVGO) – Critical semiconductor and infrastructure tech
18. CrowdStrike (CRWD) – Cybersecurity leader, securing the digital world
19. ServiceNow (NOW) – The backbone of digital workflow automation
20. MercadoLibre (MELI) – The Amazon + PayPal of Latin America
21. Sea Limited (SE) – Southeast Asia’s e-commerce and gaming growth engine
22. Vistra (VST) – A key player in the energy transition
23. Enovix (ENVX) – Next-gen battery technology, energy storage game-changer
24. Kraken Robotics (KRKNF) – A leader in marine technology and underwater robotics
25. Amazon (AMZN) – E-commerce, AWS, logistics powerhouse
This portfolio would offer a mix of core defensive moats, secular high-growth winners, and a few asymmetric bets. It reflects my belief in the continued dominance of AI, automation, cloud computing, digital finance, and healthcare innovation, while also keeping exposure to essential industrials and infrastructure plays.
Of course, markets don’t always give us the perfect entry points – but if we got a true reset, this would be a pretty interesting long-term portfolio to build and hold.
Why no China names? I used to be bullish on (and own) various Chinese companies – they have some truly world-class businesses serving the world’s largest population. But over time, the political landscape has become so fraught that it’s hard to feel confident, even when valuations seem compelling. The combination of regulatory unpredictability, government intervention, and geopolitical tensions makes investing in Chinese stocks more of a wild card than I’m comfortable with right now.
The Ups and Downs of Investing
Investing challenges you emotionally in a way that few other things do. Seeing a position deep in the red can make you question everything, while watching one soar massively in the green can tempt you into overconfidence. This emotional rollercoaster is why self-awareness is critical—staying level-headed through both drawdowns and euphoric rallies is what separates good investors from those who get shaken out at the worst times.
If you’re going to do it properly, investing takes time and effort. It’s not just about picking stocks—it’s about understanding businesses, managing risk, and continuously refining your approach. And it’s easy to confuse investing with speculating. When markets move quickly, it’s tempting to chase momentum, but true investing requires patience and discipline. The best returns often take years to materialize, and not every stock will be a winner. Even legendary investors—Buffett, Lynch, Druckenmiller—have made mistakes and held duds that never worked out.
But despite the challenges, investing can be incredibly fun, stimulating, and ultimately rewarding. There’s a thrill in spotting a great company early, a deep satisfaction in seeing a long-term thesis play out, and a sense of empowerment that comes from growing your wealth through informed decisions. The key is understanding the odds—you won’t always be right, but if you get enough big decisions correct and manage risk effectively, investing can be one of the most rewarding long-term endeavors out there.
Further Reading: Understanding Risk and Volatility When Investing
Good DIY Investing Resources
One of the key parts of being a successful DIY investor is having the right tools and resources at your disposal. Whether you’re tracking watchlists, monitoring the stocks you own (and the ones you’re considering), or researching valuations and company fundamentals, having a solid setup makes a huge difference. There’s no one-size-fits-all approach—it’s about finding the mix of tools that works best for you.
Valuation and Research Tools
A good starting point is watchlist and portfolio tracking platforms. Basic options like Yahoo Finance and Google Finance allow you to track price movements, news, and basic financials in a user-friendly way. If you want deeper insights, Seeking Alpha is great for stock analysis and investor commentary, while platforms like Morningstar provide high-quality research reports, fund insights, and long-term investment ratings.
For valuation-focused investors, Fast Graphs is a fantastic tool that helps visualize a stock’s historical valuation trends against earnings and growth rates. If you lean toward technical analysis, there are platforms that incorporate Fibonacci Pinball and other charting techniques to identify potential support and resistance levels. While I personally lean more toward fundamental investing, I recognize that technical analysis has its place, especially in managing risk and understanding market sentiment.
Beware the 'Expert' Opinion - Because Everyone Has One
One of the trickiest parts of DIY investing is filtering through the noise. Everyone has an opinion—and more often than not, those opinions are wrong (even from so-called experts). You can watch two incredibly smart analysts—both armed with extensive research, data, and experience—give completely opposing views on the same stock, the direction of the market, or the broader economy. One will argue why a stock is an absolute buy, while the other explains why it’s overvalued and doomed. The same happens at a macro level—one economist forecasts a recession, while another predicts a roaring bull market.
This is why you need to be careful who you listen to. Just because someone sounds intelligent or has a good track record doesn’t mean they’re always right. Even the best investors in history make mistakes and misjudge situations. The key is to use expert opinions as input, not gospel. Instead of blindly following anyone, focus on developing your own framework for making investment decisions.
That said, it can still be useful to follow a handful of analysts who specialize in specific sectors that interest you. The trick is to find people who provide genuine insight—not just those who confirm your biases. Listening to both bullish and bearish perspectives can help you stress-test your own thinking and avoid getting caught in an echo chamber. But at the end of the day, it’s your money on the line, so learning to think independently and trust your own research is what ultimately matters.
Managing Information Overload
That said, information overload is real, and just because data is available doesn’t mean you need to consume all of it. The goal isn’t to drown in research—it’s to build a structured process for decision-making. If you want to be a good DIY investor, you need a strategy and a set of tools that help you execute it. Whether that means focusing on fundamental data, technical indicators, or a blend of both, the key is finding an approach that gives you clarity, confidence, and the ability to act decisively when opportunities arise.
Final DIY Investing Thoughts: A Lesson in Humility
At the end of the day, these are just my own views and experiences—investing is deeply personal, and what works for one person may not work for another. If there’s one thing I’ve learned over the years, it’s that investing is humbling. No matter how much research you do, how many expert opinions you weigh, or how confident you feel in a thesis, markets have a way of surprising you. What you anticipate will happen rarely unfolds exactly as expected—or if it does, it’s usually in a way you didn’t foresee.
That’s why long-term focus, discipline, and emotional control are the real keys to success. It’s easy to get caught up in short-term noise, react impulsively, or second-guess yourself when things aren’t going your way. But investing isn’t about being right all the time—it’s about making good decisions consistently, managing risk, and letting time do the heavy lifting. The reality is that even the greatest investors in history have made plenty of mistakes, but what sets them apart is their ability to stay patient, adaptable, and rational when others aren’t.
Ultimately, DIY investing can be one of the most rewarding things you do—not just financially, but in the way it forces you to think critically, challenge your own biases, and continuously learn. It’s not easy, and it takes time and effort, but for those who enjoy the process, it’s an incredible journey—one that, if done well, can lead to both financial success and personal growth.
Carl-Peter Lehmann
I'm a Certified Financial Planner (CFP®) and investment nerd with over 20 years of industry experience, specializing in wealth management and offshore investing. When I’m not analyzing markets, I enjoy trail running and spending time outdoors. These are just my own opinions and don’t reflect those of my firm - so always do your own research before making investment decisions! (Seriously, don’t just take my word for it. Even the best investors get it wrong sometimes!)
