Too many investors use pattern-matching or financial models as their main approach, and don't consider other ways of deploying capital. With AI and technology opportunities changing fast, new approaches are needed. A CEO, author and thought leader addresses the issues.

The following article comes from Jason Ma, founder, chief executive and chief mentor at ThreeEQ. Ma advises principals at single family offices (SFOs), ultra-high net worth individuals and rising Next Gen figures. He discusses technology and AI investing – topics of obvious relevance right now. The editors are pleased to share these comments; the usual editorial disclaimers apply to the views of guest writers. To comment or provide suggestions and feedback, email tom.burroughes@wealthbriefing.com and amanda.cheesley@clearviewpublishing.com

Legendary venture capitalist Vinod Khosla recently remarked, in a conversation with OpenAI CEO Sam Altman, that 90 per cent of venture capitalists add no value to startups and 70 per cent even harm them. While some may not fully agree, the comment reflects truths I have long observed across the entrepreneur–investor ecosystem from global Silicon Valley.

Khosla’s bluntness might sound provocative, but for those of us who have spent decades in the trenches of innovation and entrepreneurship, his critique resonates. Too many investors rely on pattern-matching or financial models alone, failing to recognise that early-stage company-building is non-linear, deeply human and ultimately talent-driven. The best investors elevate, not inhibit, that process.

In my view, around 90 per cent of a startup's success stems from its founders and early key teammates. This underscores the irreplaceable value of visionary talent, grit and leadership at the earliest stages – factors that even sophisticated capital often underestimates. Yet far too many investors miss out on transformational industry impact and exceptional multiples on invested capital (MOIC) and return on investment (ROI) potential because of ego, greed, fear, flawed assumptions or a fixed mindset – rather than a visionary growth mindset.

Roelof Botha, Sequoia Capital’s managing partner, recently said: “My biggest mistake as an investor is the failure of my imagination.”

That line stayed with me. Years ago, Roelof and I served as two of three judges at a Stanford student entrepreneurship panel. His reflection reveals how imagination – often dismissed in traditional investment thinking – is in fact critical when evaluating frontier opportunities.

In my speaking engagements and business dealings with principals and chief investment officers of single-family offices (SFOs) and UHNW private investors, I often highlight a trend: more entrepreneurial investors are shifting from being passive limited partners in VC funds to pursuing direct, intelligent investments in AI and technology ventures – from early stages onwards.

Structural limitations
While many investors still allocate to select established or emerging VC funds with multiple LPs, the shift towards direct investing is being driven by clear structural frustrations and the potential for better returns in shorter timeframes.

Most VC funds underperform relevant benchmarks, restrict flexibility with seven-to-10-year (or longer) lockups, and charge management fees regardless of outcomes. They also often follow the herd – chasing familiar themes, crowded cap tables and overplayed categories or geographies.

Astute single family-offices and UHNW individuals realise that they no longer need to accept these limitations. They are exploring a more dynamic approach: intelligent direct investing in high-impact ventures, where they can back exceptional founders directly and retain strategic control.

Smart direct AI/tech investing: a mindset-driven advantage
This approach is not about writing opportunistic cheques. It is about SFO principals, CIOs and UHNW individuals who possess the mindset, skills and network to source and back transformative ventures – and who understand the nuances of emerging, high-impact technologies and business models.

Based on what I have observed, smart direct investing offers strategic advantages unavailable through fund structures:
-- Closer relationships with founders and senior executives;
-- Greater alignment with long-term values and personal objectives;
-- More control over deal terms, entry timing and exposure management; and
-- Early access to category-defining innovation while competitive noise is still low, before the market crowds in.

We are entering a moment when some AI-native companies are not just reshaping industries – they are creating entirely new categories. The convergence of compute power, capital efficiency and global tech talent makes it possible to build billion-dollar companies with lean teams and clean cap tables faster than ever before. (A “clean cap table” refers to an organised, accurate and up-to-date record of a company’s equity ownership, including founders, employees and investors.)

For entrepreneurial investors who can navigate this landscape with discernment and vision, this represents a generational opportunity – not just to earn, but to build and help shape the future.

And the upside? Returns of 100x to several hundred times in multiples on invested capital (MOIC) – or even higher in exceptional cases – are realistic for those wise enough to attract and invest in the right top deals, some of which may still be pre-revenue yet category-defining.

I believe that high-margin growth and high-MOIC opportunities are especially found in impactful, well-executed and new categories within Applied AI – part of the broader AI solution stack and ecosystem, which also encompasses enabling layers such as Edge AI, Cloud AI, and the underlying compute infrastructure including GPUs and data centres. These are precisely the kinds of opportunities that some traditional VC firms, institutional family offices and gatekeepers often overlook – or dismiss too early.

Fixed mindset vs visionary growth mindset
Despite this window of opportunity, I continue to be surprised – if not shocked – by how common fixed mindsets and linear (and often small) thinking still are, even among experienced investors. These manifest as rigid thought patterns, fear of uncertainty or overdependence on outdated validation metrics.

In contrast, a visionary growth mindset is marked by humility, curiosity, strategic imagination and adaptability. These qualities are rare but essential – both in founders and investors.

I have coached high-achieving students, leaders and entrepreneurs one-to-one. For example, one such young leader went on to identify a promising AI venture opportunity. Most institutional investors passed – focused on benchmarks or the lack of comparables. But the founder kept building. Within a few years, his still-private company became a unicorn and one of the two most recognised in its category. That is what imagination and resilience can achieve. I would not be surprised if the company is acquired for billions soon.

Having served as a mentor at the Thiel Fellowship – which has supported young adult founders and produced multiple centimillionaires and billionaires – I have learned to recognise these intangibles early. And I have seen how the right capital, paired with the right mindset and skillsets, unlocks non-linear or exponential outcomes.

From passive allocators to strategic co-builders
The smart direct investor does not merely allocate capital. They build relationships, support founders and contribute to value creation – both tangibly and intangibly.

Some of the most astute SFOs I know are actively evolving from passive LPs into strategic co-builders. They are:
-- Investing with patient capital, conviction and clarity of purpose;
-- Collaborating with peers, operators and trusted advisors to source proprietary opportunities;
-- Focusing on fewer, higher-quality deals with founders capable of driving meaningful impact – and generating exponential upside; and
-- Mentoring Next Gen heirs and leaders to think critically, act boldly and lead wisely.

This approach requires time, discernment and courage – but the upside is not measured solely in outsized returns. It is measured in influence, legacy and contribution.

Smart, strategic and human
Too many family offices remain held back by structures and habits designed for a different era. For those with the wisdom to lead or act rather than to just follow, smart direct AI/tech investing presents a timely and transformative opportunity to rethink what wealth – and influence – can mean in this decade and beyond.

It is not about chasing shiny trends. It is about thoughtful engagement – investing in impactful solutions to real problems, backing extraordinary talent, generating outsized returns and bringing a human dimension to innovation.

If this perspective resonates – whether you are an SFO principal, CIO, UHNW investor or someone who thoughtfully advises them – I would welcome a private, nuanced conversation.