Aspirational Investing

Conventional wisdom in the financial sector suggests a compromise exists between above-market returns and impact. We aspire for more. In this series, we speak to fiduciaries at the vanguard, who refuse to compromise between these two objectives, innovatively pursuing top-quartile performance inclusive of their unique missions.
E007 | Jonathan Goldberg
In this episode of Aspirational Investing, Mike Miller, CIO of Crewcial Partners, sits down with Jonathan Goldberg, Chair of Crewcial’s Investment Committee, to unpack the real risks in today’s market hiding in plain sight. This isn't about short-term headlines or dramatic forecasts. It’s about long-term discipline, structural misalignments, and how a passive investing boom could be setting investors up for disappointment. And it raises a more fundamental question: Could the greater risk to long-term capital be complacency, not volatility?
Insights
- Certainty Is a Red Flag, Not a Comfort: A critical blind spot in today’s markets is that investors aren’t afraid. They’re too certain. Certain that the S&P 500 will always deliver. Certain that a handful of dominant companies will remain untouchable. Certain that owning the index is the safest option. But this sense of safety is often built on concentration. When 40% of an index is tied to just a few mega-cap names, it only takes one narrative shift to create permanent capital impairment.
- The Market’s Structure Is Working Against Long-Term Investors: The makeup of today’s market is structurally different. Passive flows dominate over the medium term, while firms oriented towards short-term trading dominate the rest. Neither is allocating based on long-term fundamentals. This has created a pricing environment where dislocations are more common and where being early, or simply patient, often looks like being wrong. Fundamental investors are no longer setting the tone. That has consequences.
- Diversification Must Be Functional, Not Cosmetic: Most portfolios today are diversified in name only. Holding hundreds of line items doesn’t protect you if most of them depend on the same macro narrative playing out. A functional portfolio needs real diversity in sources of return across geographies, sectors, styles, and sizes. Smaller-cap companies with stable cash flows, international equities, and out-of-favor businesses offer differentiated risk profiles that are underrepresented in typical allocations.
- Liquidity Is a Strategic Asset: Liquidity isn’t just about daily pricing. It’s about flexibility. In today’s environment, when private market liquidity is tightening and secondaries often trade at discounts, illiquidity can quickly become a constraint. When liquidity dries up, investors lose the ability to rebalance, to capitalize on dislocation, or to exit broken theses. That lack of optionality becomes a risk in itself.
- Returns Don’t Show Up on a Schedule: Most of the return in fundamentals-driven investing doesn’t accrue slowly, but arrive in short, sharp windows after long periods of inaction; many managers and committees aren’t structured to survive those lags. The ability to stay with a position while it looks wrong, even for years, is often the difference between long-term outperformance and missed opportunity. Patience, on its own, isn’t enough; it has to be backed by conviction, alignment, and governance that can support it.
- “Safe” Portfolios May Be Failing Their Missions: A common assumption is that sticking with the S&P 500 is the safe move. But for long-term institutions with 5% spending needs and 2-3% inflation, the math on a 5-6% return simply doesn’t work. This slow erosion of purchasing power is often overlooked because it feels safer than being wrong on something different. But for stewards of capital, avoiding embarrassment can come at the cost of fulfilling an institution’s purpose.
Core Takeaways
- Certainty is a red flag. When conviction becomes complacency, permanent capital loss isn’t far behind.
- Passive is not neutral. The structure of passive flows reinforces existing trends and ignores valuation or fundamentals.
- Diversification means exposure to different narratives. If 70% of your portfolio is tied to one story, you're not diversified.
- Liquidity = flexibility. Whether it’s seizing an opportunity or cutting a mistake, you need room to move.
- Patience requires structure. Investors need the infrastructure and support to hold through discomfort and reap the reward.
- Optics aren’t outcomes. Committees focused on short-term optics risk eroding their institutions' long-term impact.
- Being different is the job. Stewards must prioritize long-term health over comfort in a crowd.
The message is clear: long-term capital requires long-term thinking and the ability to act (or patience to not) when it matters most.
- Permanent capital is an investment structure without fixed timeframes, unlike traditional private equity funds, which require selling assets within set lifecycles. This flexibility allows investors to hold onto assets as long as they find it beneficial, avoiding forced sales regardless of market conditions. By removing these time constraints, permanent capital fosters more strategic, uninterrupted partnerships, focusing on long-term growth rather than the pressure of achieving short-term gains.
DISCLAIMER
This podcast is for informational purposes only and does not constitute financial, legal, or investment advice. The opinions expressed are those of the speakers and do not necessarily reflect the views of Crewcial Partners LLC. Listeners should consult with a qualified financial advisor before making any investment decisions. Past performance is not indicative of future results, and all investments involve risk.
What were some of the main successes of Crewcial Partners last year?
Summary: Most importantly, we maintained our long-term posture through an unfriendly market. Markets have a way of overreacting to events; however, our clients stayed on track and kept their public equity exposure at high levels. Our process ensured we never faced liquidity challenges or any issue that demanded we act in a short-term matter.
Lesson: A long-term bias works but requires discipline, diversification, and an understanding of expectations. Fundamentals and valuation—the price you pay for something— ultimately matters. Crises and difficult times have winners and losers. The winners are ultimately those with the strongest balance sheets, best business strategies, and the most capable manager teams; they win over the longer term because they're better than their competition.
What are your thoughts on sizing in the current environment?
Summary: It can seem contrary to human nature at times; the stuff that does well, you want to see become a bigger and bigger part of the portfolio. However, you should be adding money to managers that have struggled but are poised to rebound, keeping in mind your longer-term return profile. Sizing is important and depends on a deep understanding of diversification and manager volatility profiles.
Lesson: Take advantage of the natural cyclicality within markets, selling at the peaks and buying the bottom is the way to long-term sustainable success. Be proactive when managers have a great year. When Crewcial has a manager that's up 100%, we ensure that we trim back 25-50% so the capital is ready to redeploy into out-of-favor managers with even stronger future prospects.
What are some of the areas that could be improved from 2023?
Summary: We are still trying to wrap our heads around the way markets are actually functioning; the gap between price and fundamental value seems as if it's become unbounded. This creates a problem of balance. If you're constructing a diversified portfolio, one of your underlying assumptions is that it will moderate volatility and some of the short-terms concerns; this should allow you to play offense when things are bad and a little defense when things are really good. But that falls apart if markets are creating high correlations that shouldn't exist between strategies. We’re still learning to better understand which conditions can and will create more of these correlation issues, so that we don't end up constructing portfolios that require truly extraordinary levels of patience to see through.
Lesson: Cultivate a better understanding of correlation among managers. Thinking about managers based on the way they behave in different market climates is important. Prepare for various environments and build portfolios that are not going to have several seemingly distinct strategies reacting to the same market environment. Diversification is ultimately always your friend.
What are some of the insights you’ve gained from your latest year of travel?
Summary: Being back on the road has been one of the great events of 2023. It’s rewarding to physically sit down with people, whether in Europe, Asia, South America, Africa, or the United States, and really hear what they’re seeing on the ground, what they’re doing in their portfolios, and the real-world implications, because markets aren't necessarily the real world. Being reminded how different people see the world differently is immensely important as an investor.
Lesson: Preferable options exist outside indexation; opening up to a global perspective broadens one’s ability to consider truly impactful diversification. The goal is to find differentiated thinking wherever it is. We're not looking for investment managers, we’re looking for thoughtful, engaged people who invest.
What does history tell us for “Magnificent Seven” index funds going forward?
Summary: The index has reached a very high level of valuation concentrated in a group of unbelievably dominant companies. However, while no one is arguing that Apple is a bad business, there is a price for everything and this price seems too high right now. From the 60s through the 00s, people felt the same about many companies that didn't prove to be very good investments. One way to illustrate this is to look at the top five in late 90s, which included Cisco, Intel, General Electric, Microsoft, and IBM. If we exclude Microsoft from the equation, these are all still pretty powerful businesses but they have not been good stocks to own. It’s the inevitable nature of impermanence. We can almost guarantee ten or 20 years from now, the current names will be around, but they probably won't be the most popular or dominant names in the market.
Lesson: Design portfolios to capture the broader economy; while well-constructed portfolios will always have allocations to bigger names, entire swaths of the economy are growing at a much faster rate than these brand-name businesses and are currently being overlooked by investors. Capture long-term opportunities today cheaply.
What is Crewcial excited about for 2024?
Summary: First, ESG, which has unfortunately become a very controversial subject. However, at the end of the day, it's a powerful risk framework; from our perspective, we need to be able to arm both our clients and our research team and consultants with better information on this subject and approach, as it’s a complicated topic. We can't make it simple, but we can identify very specific variables at the portfolio company level to transparently consider which managers and portfolios have a higher level of risk around material environmental, social, and governance issues that affect their viability as good investments.
Second, another big change at Crewcial was our formation of an investment committee. We’re doubling down on our approach, allowing talented team members to focus on what they understand best and follow their passions as investors, but we’re now taking those passions and directing them into somewhat of a more formalized process. It's based on tracking, monitoring, and ensuring individuals get the training they need to scale and fully capture the bigger picture to find the best managers, no matter their initial backgrounds upon entering the firm, while pairing complementary skillsets to bring out the team’s full potential.
Lesson: Don’t be afraid to be different while embracing the fundamental rules of finance. Identify the full scope of everyone’s areas of strength and play off each to build a greater whole. Embrace idiosyncrasies and preferences while being open and honest with feedback and assessments. We do not treat our investment team members as analysts, rather as investors cultivating an owner’s mindset. We're trying to find ways to capitalize on differentiated perspectives to ultimately uncover the difference between market price and fundamental value; seeing things differently, and cultivating an environment in which such perspectives can range openly, is a critical element of that.
We don’t just want the usual suspects from the same handful of schools, we want to expand our collective perspective to include more women, ethnically diverse individuals, and people of all persuasions from different parts of the country or with different educational or experiential backgrounds—talented people come in all shapes and sizes. A diverse team of diverse perspectives is intended to capture the overlooked points of view necessary to uncover the next great idea.
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Crewcial Partners LLC is a Securities and Exchange Commission registered investment advisor. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any securities. Past performance is not indicative of future results, and investments involve risk and are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed here.