A question I get asked almost weekly: “What’s your best bet for this weekend?”
It seems like a straightforward question, but after 20+ years in this industry, I’ve learned it’s the wrong one to ask. The far better question – one that few people consider – is: “Which betting approach best matches my personal risk tolerance and financial goals?”
Back in 2013 when we first started investing our own capital in MLB opportunities, we realized something crucial: there’s no universal “best strategy” in sports investing. What works brilliantly for one investor might be completely wrong for another. This insight eventually shaped how we structure our recommendations through Optimus II and how we onboard new clients at 69Advisory.
Today, I want to share our framework for matching investors with their optimal strategy – something we’ve refined through years of working with clients from diverse financial backgrounds and with vastly different risk appetites.
Most people intuitively understand that higher potential rewards typically come with higher risks. What’s less understood is how to quantify this relationship in sports betting and find your personal sweet spot.
In traditional investing, tools like the Sharpe ratio help investors measure risk-adjusted returns. In sports betting, we need similar frameworks tailored to this unique asset class.
At 69Advisory, we map strategies along a spectrum with several key variables:
Let me illustrate with two vastly different approaches we’ve helped clients implement:
This approach focuses on finding slight edges in major markets, primarily point spreads and totals in major sports. It’s characterized by patience, discipline, and high volume. Bets typically have close to even-money payouts, but the win rate exceeds the break-even percentage.
This approach selectively targets undervalued underdogs, accepting a lower win rate in exchange for larger payouts when correct. It requires significant psychological fortitude due to longer losing streaks, but the ROI can be comparable or even superior to Strategy A.
During our client intake process, we walk through a series of questions that help determine the optimal approach. I’ve simplified these to five key considerations you can use to assess your own risk profile:
Be brutally honest with yourself. Even the best sports betting strategies encounter losing periods.
In 2017, shortly after launching Optimus II, we hit a rough patch where one particular client became extremely anxious despite being informed that such downswings were normal and accounted for in our projections. After several stressed phone calls, we shifted him to a more conservative approach with lower variance. His ROI expectation decreased slightly, but he remained committed to the strategy and ultimately succeeded because it matched his psychological comfort zone.
Another client during the same period barely noticed the downswing, viewing it as normal variance. She remained with the higher-volatility strategy and was rewarded when performance reverted to the expected mean.
Same mathematical edge, different psychological experiences.
This question is crucial but often overlooked. Someone investing 2% of their capital should approach sports betting very differently from someone investing 20%.
In 2019, we worked with two clients with similar net worth but dramatically different allocations to sports betting:
For Client X, we recommended a high-variance strategy targeting larger payouts. Even significant downswings would have minimal impact on his overall financial position, allowing him to weather variance for potentially higher returns.
For Client Y, we implemented a conservative approach prioritizing capital preservation and steady growth, given the larger portion of his wealth at stake.
Sports betting rewards patience, but some approaches require more than others.
When we expanded into Korean baseball markets in 2020, we were clear with clients that our analytical edge would take longer to materialize compared to more established markets. Some clients with longer time horizons embraced this opportunity, while others preferred to stick with markets that offered more immediate feedback loops.
Your optimal strategy might differ based on whether you’re looking at:
Longer timeframes generally allow for higher-variance approaches, provided you have the discipline to maintain course.
This seems obvious but deserves explicit consideration. Are you trying to:
Each goal suggests a different optimal approach. At 69Advisory, we’ve learned that aligning strategy with client goals dramatically improves long-term satisfaction and retention, even when raw returns might be slightly lower than a theoretically “optimal” but psychologically unsuitable approach.
Some sports investment strategies require significant time commitment, while others can be more passive.
In the early days of our service (around 2016-2017), we offered only a high-involvement approach requiring clients to place bets within specific timing windows to capture optimal lines. Some clients thrived with this active approach, while others found it burdensome.
Today, Optimus II generates recommendations across a spectrum of involvement levels, from “place within 10 minutes of alert” to “place anytime before game start” options, with expected value calculations adjusted accordingly.
Your available time and desired involvement level should influence your strategy selection.
To simplify this multidimensional decision, we developed a strategy matrix that helps match clients to approaches. Here’s a simplified version:
| Strategy Type | Win Rate | Avg Odds | Variance | Min Bankroll | Best For |
|---|---|---|---|---|---|
| Conservative | 56-60% | -120 to -110 | Low | 30x unit | Risk-averse, capital preservation focused |
| Balanced | 52-56% | -110 to +110 | Medium | 50x unit | Most investors seeking steady growth |
| Aggressive | 45-52% | +100 to +150 | High | 75x unit | Those prioritizing maximum return, comfortable with swings |
| Speculative | 35-45% | +150 to +250 | Very High | 100x unit | Investors with high risk tolerance and long horizons |
Your optimal placement within this matrix depends on your answers to the five questions above.
Over the years, we’ve observed several typical mismatches between investors and strategies:
The Impatient Conservative: Investors with low risk tolerance but unrealistic expectations about feedback loops. They want low variance but get anxious when it takes 100+ bets to see expected results.
The Undercapitalized Aggressive: Bettors who choose high-variance strategies without sufficient bankroll to weather inevitable downswings, leading to emotional decisions during drawdowns.
The Time-Constrained Active Trader: Clients who select strategies requiring rapid execution but lack the availability to place bets in optimal windows, sacrificing expected value.
The Variance-Sensitive Maximizer: Those who want maximum returns but become distressed during normal variance, often abandoning strategies prematurely.
The most successful long-term clients we’ve worked with share one common trait: they selected strategies that aligned with their psychological comfort zones, even when more aggressive approaches might have offered slightly higher theoretical returns.
If you’re developing your own sports investment strategy (or choosing a service to work with), consider these practical steps:
At 69Advisory, we formalized this process in 2024 with our custom balance sheet in the members section. This tool allows clients to track performance against expectations and make data-driven adjustments as needed.
One advantage of our approach at 69Advisory is the ability to simultaneously operate multiple strategies across different sports markets. This allows clients to diversify not just across sports but across risk profiles.
A common structure we recommend:
This tiered approach provides stability while still capturing upside from higher-variance opportunities.
The beauty of sports investing lies in its flexibility. Unlike many traditional investment vehicles with fixed characteristics, sports betting strategies can be precisely tailored to your personal risk profile.
Our most successful clients don’t chase the “best” strategy – they find the one that aligns with their goals, psychology, and circumstances. The perfect strategy isn’t the one with the highest theoretical ROI; it’s the one you’ll stick with through inevitable variance to realize long-term expected value.
After all, as we often remind our newer clients: “The most sophisticated strategy in the world is worthless if you abandon it at the first sign of variance.”
Interested in finding your optimal sports investment approach? At 69Advisory, we’ve been helping clients match strategies to their risk profiles since 2016. Explore our customized service options or contact us to discuss which approach might best suit your goals.
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