This is my evaluation of what I call the Oregon Public Employees Retirement Fund1 / USV paradox. Oregon committed ~$260M across all vintages to USV which returned 6.7x TVPI on contributed capital, yet this was a tiny fraction of the $64.5B total PE book. This quantifies the “needle in a haystack” problem, even legendary GPs can’t move the needle when diluted across a massive portfolio.

The USV numbers are genuinely extraordinary. The 2004 fund alone turned $22.3 million contributed into $307.4 million distributed — a 13.82x multiple with a 66.9% net IRR, powered by early bets on Twitter, Zynga, and Tumblr. The 2012 fund, driven by Coinbase, produced a 23.78x TVPI and a 53.5% net IRR. Even USV's worst mature fund (2008 vintage) delivered a 4.35x multiple. By any measure, USV has been one of the greatest venture capital performers of all time for Oregon.

Sadly, even including USV, Oregon’s PE book underperformed a plain vanilla stock index by over 3 percentage points annually. Even generating $1 billion+ in distributions, USV represented perhaps 2% of total PE distributions. The other 98% included plenty of mediocre and outright terrible performers—funds like Novalpina Capital (-34.9% IRR), Lion Capital Fund II (-7.3% IRR), First Reserve Fund XII (-16.4% IRR), and dozens of others visible in the OPERF PE holdings data. The “2 and 20” fee structure means every one of these underperformers still extracted significant management fees, creating a systematic drag. In essence, approximately 415,000 current and future retirees, teachers, firefighters, police officers, state agency workers, and other public-sector employees across Oregon, were paying PE managers billions in fees to deliver returns worse than a free index fund.

Another portfolio-level observation is that Oregon’s PE overweight (peaking at 28.4% vs. the 20% target) forced the treasury to sell public equities to meet benefit payments and maintain liquidity. This created a perverse dynamic where Oregon was effectively selling its best-performing asset (public equities, up significantly in 2023-2024) to hold its worst-performing one (PE). Divest Oregon calculated this misallocation cost $3.7 billion since 2023. The illiquidity trap of PE—you can’t easily reduce exposure when you need to—turned a return problem into a compounding structural problem.

The math of scaling venture & the institutional LP trap

This is what makes USV so instructive — not just their returns, but their discipline. USV has deliberately maintained small fund sizes throughout its history. Their first fund in 2004 was $125 million; their most recent core fund in 2022 was $275 million. Fred Wilson has written openly about staying small: if you have a fund in the $500 million to $1 billion range, you need many large exits to return the fund even once, but your LPs expect 3x. USV's approach — small teams, high conviction, early-stage focus with check sizes of $1–20 million — is structurally designed to produce the kind of outlier returns Oregon actually received.

The problem isn’t that Oregon chose badly with USV. The problem is that institutions of Oregon’s size — managing $100 billion for 415,000 beneficiaries — face structural constraints that make concentrated venture allocation nearly impossible. A $100 billion fund that allocates even 2% to venture commits $2 billion. Deploying $2 billion into sub-$300 million funds like USV requires an unmanageable number of GP relationships. Each relationship requires due diligence, monitoring, and governance. The staffing, infrastructure, and consultant fees to manage that program eat into returns before the first dollar is invested.

So what happens? The pension gravitates toward larger, easier-to-deploy commitments — $200–500 million checks into mega funds. These are efficient to manage but structurally unlikely to outperform public markets after fees. The pension gets “private equity exposure” on paper. What it doesn’t get is venture-grade alpha.

What this means for family offices

This is where the Oregon story becomes directly relevant to how families should think about building a venture portfolio. I wrote previously that venture is truly an access class, shaped through community — not a box to check on an asset allocation spreadsheet. The Oregon case proves why.

An average family office deploying $5–20 million into venture every 2-4 years has a structural advantage over a $100 billion pension fund. Not despite its size — because of it. A smaller LP can concentrate in high-conviction high-touch GP relationships rather than managing a large portfolio. It can efficiently access sub-$300 million funds where the return data is strongest. It can co-invest alongside those GPs to increase exposure to breakout winners. And it can do all of this without the bureaucratic overhead, consultant layers, and rebalancing pressures that forced Oregon to sell public equities at the worst possible time.

The irony is that the families who feel they’re “too small” for venture are actually the right size for it. The question is not “can we commit $500 million to private equity?” — it’s “can we earn the access to the right 3–5 managers and stay disciplined over multiple fund cycles?” That’s a relationship problem, not a capital problem. And it’s a problem that scales with trust, not with check size.

Does venture scale? The returns say no. But access to venture — earned through conviction, community, and showing up over time — compounds in ways that a pension consultant’s spreadsheet will never capture.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

When my cousin and I started GEX in 2015, we didn’t set out to build a traditional venture capital firm. We were a family office, rooted in multigenerational values, backed by family capital, and driven by a simple conviction: that the best way to participate in innovation was through relationships, not transactions.

A decade later, the data has caught up with what we experienced firsthand. Family offices are no longer passive allocators sitting on the sidelines of venture capital. They are becoming its most consequential participants.

The Numbers Tell the Story

According to PwC’s Global Family Office Deals Study 2025, venture capital and private equity now account for half of all family office deal activity. Club deals — families co-investing alongside other investors — represent nearly 69% of transactions. J.P. Morgan’s 2026 Global Family Office Report shows that high-return-targeting family offices allocate over 40% of their portfolios to alternatives. And the average single-family office deploying capital into venture now manages close to $1 billion in assets.

These aren’t marginal shifts. Family offices collectively control more than $14 trillion — exceeding the combined assets of the global private equity and venture capital industries. When that much capital changes its behavior, markets move.

Why Now?

Three forces are converging:

• Companies are staying private longer. I’ve written about this before — 87% of U.S. companies with revenues over $100 million are not publicly traded. If you want access to the fastest-growing companies in the world, you have to go private. Family offices understand this intuitively. They’ve been making long-duration, illiquid bets for generations.

• The next generation is showing up differently. Most family offices today were established after 2001. Three-quarters benefit from the entrepreneurial involvement of their founders, and only 12% are run primarily by heirs. This is not old money sitting still. UBS reports that 31% of U.S. entrepreneurs plan to create their own family office. The line between founder and family investor is disappearing.

• Traditional fund structures aren’t enough. Family offices are increasingly favoring direct investments, co-investments, and custom structures over blind pool fund commitments. They want control, alignment, and the ability to invest according to their values — not just a slot in someone else’s portfolio construction.

GEX: A Case Study in the Shift

Our evolution tracks this macro trend almost perfectly. We started as a family office making angel investments and supporting Persian entrepreneurs between London and Silicon Valley. Over time, we refined our approach — moving from direct deals to a fund-of-funds strategy, partnering with leading and emerging VC managers, and co-investing alongside them at the early growth stage.

In 2025, we crossed an important threshold. With the support of trusted limited partners, we officially transitioned from a family office investor to an independent venture capital firm. We didn’t abandon our family roots — we institutionalized them.

Today, GEX invests in top-performing VC managers while securing co-investment rights into their breakout companies. We screen hundreds of opportunities each quarter. We invested in a tiny fraction of the managers we reviewed in our last fund cycle and we did it all while building a community of values-aligned families and investors who believe that how you invest matters as much as what you invest in.

Looking Ahead

The family office boom is not slowing down. PwC projects continued growth in club deals, direct investments, and innovation-led sectors like AI, SaaS, and healthcare. As more families make this transition, we’ll see a new generation of venture firms — firms built on family values, community trust, and multigenerational thinking. GEX was built on these principles before they became a trend. We plan to keep it that way.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

One of the greatest luxuries family office investors possess is time. Unlike institutional VCs, they do not have a 10-year fund clock ticking in the background, nor do they have capital calls on a rigid schedule. They have the ultimate freedom: the ability to wait for the perfect pitch.

However, this “superpower” can often become a trap.

Total flexibility frequently leads to what institutional investors call “style drift.” An investor might aggressively fund three startups in Q1 due to optimism, then disappear for nine months because of other business demands or market shifts. The result isn’t a portfolio; it’s merely a collection of deals.

The strategic challenge for family offices is balancing the flexibility of direct investing with the discipline of a programmatic fund strategy. The goal isn’t to choose one or the other, it’s to use them together to build something durable.

The Framework: Funds as the Anchor

To build a venture portfolio that generates consistent returns, a “base load” of exposure is essential. This is where fund commitments play a critical role.

A fund portfolio acts as the “pace car.” By committing consistently to high-quality managers—whether established firms or emerging specialists—investors ensure they are in the market every single year. This solves the “vintage risk” problem. Since no one knows which year will produce the next generational outliers, having funds deploy capital ensures the family doesn’t miss out simply because they were focused on other operating businesses.

Funds also provide the discipline of professional due diligence and long-term relationship building that is hard to replicate with a small team. They are the “training log” of the strategy: consistent, repetitive, and foundational.

The Freedom: Directs and Co-Invests as the Alpha

If funds provide the beta (market exposure), directs and co-investments are where investors hunt for alpha—and express their values.

This is where judgment and specific convictions come into play. With the “safety net” of a fund portfolio, a family office can afford to be highly selective with direct checks. There is no pressure to do a deal just to put money to work.

Co-investments allow families to double down on winners emerging from their fund managers, effectively paying lower fees on their highest-conviction bets. They can back founders who align deeply with community values or specific industry expertise, offering patient capital that institutional funds cannot match. This flexibility allows the family office to be a “sniper” rather than a “shotgunner.”​

The Balance: Governance as a Shield

The danger, of course, is allowing the “freedom” bucket to cannibalize the “framework” bucket. It is easy to get excited about a flashy direct deal and drain the liquidity meant for a capital call.

This is where governance—and a clear Investment Policy Statement (IPS)—becomes the most valuable tool.

An IPS shouldn’t be a constraint; it should be a decision-making filter. It defines the ratio—for example, allocating 60% of the venture budget to core funds and 40% to opportunistic directs.

When a deal arrives that doesn’t fit, the IPS allows for a “No” that protects relationships.

• “The 2026 governance policy limits direct exposure to [Sector X].”

• “The allocation for direct checks is fully committed this quarter, but an introduction to fund partners is possible.”

Governance protects the strategy from enthusiasm. It ensures that direct deals remain high-conviction “freedom” plays, rather than impulsive distractions.

Doing It Together

Balancing these two engines—funds and directs—is complex and requires constant calibration.

This highlights the value of building a community of aligned investors. The goal isn’t just to swap deal flow, but to help one another maintain that balance. Peers can share notes on fund managers to build the “Framework” and syndicate their best “Freedom” opportunities to trusted partners.

The opportunity is to stop choosing between being an LP and being a direct investor, and instead build portfolios that possess the discipline of a pension fund but the soul of a family office.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

When a family has already won the game of business, the focus inevitably shifts from accumulating capital to defining its deeper purpose. Wealth, once a unifying force in the early days of building the enterprise, can gradually become a source of complexity, different branches, geographies, generations, and perspectives pulling in separate directions.​

In such moments, capital allocation alone is no longer enough. Business (and now venture capital investing) has to evolve into something more: not just a vehicle for financial returns, but an organizing force that reconnects the family around shared meaning, decision-making, and entrepreneurial mission.

This has played out in my own family. I routinely connect with uncles and cousins from different branches; we lead separate lives and follow different rhythms, yet venture, due to its entrepreneurial nature, quietly became our common ground.

Venture for a Higher Purpose

The moment an uncle mentioned a “higher purpose” for our family’s investing practices, it stopped being a lofty concept. When we evaluated an investment in a promising technology, the same questions surfaced naturally: Is this the kind of future we want to support? Does it match who we are as a family? That simple, shared act of evaluation did what years of standard family conversations never could.

We have explored many asset classes (art, real estate, small businesses, even digital assets) but venture remains distinct. It holds a much deeper capacity for what we believe is worth achieving over generations.

Venture is the most fundamental way to practice delayed gratification, values-aligned investing, and relationship-driven sourcing. What makes it unique is that it forces us to articulate what we actually believe in. Every investment is a small declaration. Over time, those declarations add up to a portfolio that reflects who the family is, not just what it owns.​

I was pleasantly surprised to see the J.P. Morgan 2025 Principal Discussions report capture this sentiment so well: many of the world’s wealthiest families now describe their goal not as “beating a benchmark,” but as backing founders and technologies they would be proud to tell their grandchildren about.​

I have also been actively seeking venture-focused family office communities, like Family VC, that reinforce this pattern. When family offices come together around venture, the conversation naturally moves beyond deal terms to something deeper: How do we support entrepreneurs beyond capital? How do we invest with patient, flexible capital that reflects our values? How do we navigate family dynamics while building a portfolio we’re proud of?​

At the outset of 2026, I wanted to write a post that is deeply meaningful to me. I have used venture for more than a decade as a way to bring my own family together, and I am now at the cusp of expanding that circle to include friends and other values-aligned investors. It is a big step, and one I take very seriously.

The fact that I am motivated by duty and love beyond just reward, is the reason I am doing it. I truly believe I can help families and investors, especially the next generation, find a reason to talk regularly about something that is both financially real and emotionally safe. I draw from my own experience with my uncles and cousins to say that this regular cadence—reviewing a deal, debating a thesis, celebrating a milestone, or learning from a loss—creates the connective tissue that keeps families and communities aligned across generations.​

Ultimately, venture capital and financing entrepreneurs gives us a concrete way to live out a higher purpose together. Instead of measuring success only by IRR, we can measure it by the quality of our conversations, the founders and technologies we choose to stand behind, and the stories our grandchildren will one day tell about what we did with the advantages we were given.​

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

In 1978, Dan Bricklin sat in a Harvard Business School classroom, staring at a chalkboard crammed with numbers. When professors changed a single assumption, students scrambled to recalculate everything by hand. It was error-prone and slow. Bricklin dreamed of a “word processor for numbers,” a tool that would let anyone model ideas and instantly see results. VisiCalc was born; soon after, Mitch Kapor steered Lotus 1-2-3 to become a household name, and spreadsheets changed number crunching for non-coders forever.

Today, we’re watching history repeat. The revolution isn’t about numbers anymore. It’s about code.

The First Wave: Spreadsheets for All

Before the spreadsheet, efficient computation was reserved for coders and technical users of computers. VisiCalc and Lotus 1-2-3 broke down the barriers, letting accountants, marketers, and teachers create their own spreadsheets with no coding required. Sales boomed, venture capitalists saw wild returns, and IBM’s $3.5 billion Lotus buyout redefined what software could mean for Wall Street.

But the real impact was outside boardrooms: teaching assistants tracked grades, theaters optimized showtimes, families managed budgets, the spreadsheet software application still to this day empowers untrained users wield computational power. In finance, spreadsheet is still a highly desirable skill with all macros and integrations extending the power through web data.

The Vibe Coding Era

Jump to 2025. AI is the multiplier, ”vibe coding” is a new catchphrase coined by Andrej Karpathy, a deep learning pioneer and highly respected AI practitioner. He put forward a bold claim: software is now written in English. Want an app? Describe it. See an error? Paste it in, AI will fix it. No classes, no syntax, no gatekeepers.

Both moments, spreadsheet creation and vibe coding’s rise, were fueled by a democratizing vision: put creative control in more hands.

• Spreadsheets let domain experts, business leaders, scientists, teachers, become number crunchers.

• Vibe coding gives designers, marketers, entrepreneurs the power to build software, unleashing creativity with the friction gone.

Investor Observations from Spreadsheets to understand Vibe Coding

• Don’t just build for experts. The product that wins will put usability and creativity over unnecessary complexity.

• Be ready for explosive scale. Lotus’ early revenue flew past forecasts. Vibe coding is seeing the same.

• Partnerships matter. The right collaborative models are key for sustainability.

• Distribution is still king and will outlast the first movers. Spreadsheets are everywhere and the dominant player is not the first mover. Vibe coding will follow a similar path.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Venture capital’s roots, and the unique role private wealth plays, are most clearly understood by tracing the evolution of “alternative assets” across centuries. In the 18th century, short-term merchant credit was the original alternative asset. This innovation, referenced in Tom Nicholas’s VC: An American History, offered families higher yield and risk than traditional holdings, underwriting bold commercial and political ventures of their time.

Primer: The Evolution of Alternatives

• 18th Century Alternatives: Merchant lending and private notes, exemplified by Robert Morris and the Bank of North America, allowed families and traders to finance trade, expeditions, and enterprises outside public markets. This marked the earliest “alternative asset” class in America, where private wealth enabled innovation and national development.

• 19th & 20th Centuries: The growth of industrialization saw alternatives shift to railroad bonds, private industrial finance, and direct equity stakes in transformative ventures.

• Modern Alternatives: Today, the alternatives spectrum includes PE, VC, hedge funds, credit, infrastructure, and emerging niches like crypto or impact investments, each reflecting shifts in technology and investor appetite.

Family Offices: Shaping and Creating Niches

Family offices have always been nimble adopters—and even architects—of frontier opportunities. Their principal mindset, deploying personal wealth rather than outside capital, empowers them to move quickly, support contrarian ideas, and create new markets. Just as Robert Morris channeled family and merchant capital into nation-building ventures, modern family offices continually seek new edges within the expanding universe of alternatives.

Principal vs. Agency Mindset

The distinction between principal and agency mindsets is foundational. Family offices act as principal investors—deploying their own assets, with a focus on mission, wealth preservation, and generational stewardship. Institutional VC, by contrast, operates as agent, investing on behalf of third-party capital—prioritizing fund cycles, scale, and short-term performance metrics.

Stewardship vs. Performance

Stewardship underpins many family office strategies, aligning investment with values, generational continuity, and education. Performance-driven models, prevalent among institutional VCs, deliver speed and scale but may favor immediate exit options over broader impact or legacy.

Always a New Frontier

History shows that alternatives are in constant flux: short-term credit gave way to industrial finance, then to private equity and VC, and now to digital assets and new frontiers. Family offices, given their independence and multi-generational focus, remain ideally positioned to discover the next wave of alternative investments.

Blending Principal Mindset with Agent Rigor: A New Breed of VC

Increasingly, I’m observing—and fortunate to support—a growing niche of family office spinouts and venture funds that blend the best of both worlds. These initiatives are led by families and principals who retain the values, flexibility, and conviction of the principal mindset, but hold themselves to the disciplined standards, transparency, and accountability usually found in agency-driven firms. This hybrid approach results in funds and allocators that can invest with purpose and agility, yet benchmark themselves against the highest performance criteria.

Furthermore, next-generation principals and capital have become more ambitious, taking a keen interest in VC as allocators or as champions of new models. They’re forging collaborative platforms, spearheading innovation, and redefining what it means to steward capital for both impact and returns. As these trailblazers enter the venture space with both conviction and professional rigor, I believe they are shaping the future of alternatives, building a culture that truly marries legacy and leadership with results and reputation.

UPDATE: Historical Roots and Modern Shifts in Human Capital

An astute reader pointed out that iconic VC firms such as Bessemer and Venrock were originally backed by family offices, highlighting that this “new breed” of VC spin-out actually has a storied legacy stretching back several generations. Bessemer traces its roots to the Phipps family office, managing assets after the sale of Carnegie Steel, while Venrock was explicitly formed as the venture arm of the Rockefeller family, building on decades of direct investment activity by the family itself.​

Historically, family offices acted as both capital providers and architects of early alternative asset markets, but the human capital was often professionalized externally. What’s notably different in this cycle is the rise of family office spin-outs and funds where next-generation family members themselves are actively leading, investing, and building VC platforms. This direct participation of principal talent alongside principal capital creates a powerful mix: combining generational values, deeper alignment, and fresh entrepreneurial drive as family offices transition from passive capital allocators to active shapers of the venture ecosystem.​

More recent data and trends confirm that next-gen family office principals increasingly view themselves not only as stewards but as ambitious participants and innovators—allocating capital, building collaborative platforms, and embedding their own talent into venture initiatives and emerging funds. This mirrors, and in many ways advances, the legacy families have had in venture investing since the industry’s earliest days, but with a modern twist: human and financial capital coming together within the family office continuum, fueling the next wave of impact and performance in alternatives.​

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

We believe that specialist venture capital fund-of-funds represents one of the most significant ways in which private wealth management will shape the markets in the near future. This belief is primarily driven by a human capital perspective as it provides an alternative path for next gens instead of 1) continuing to operate in the family business, 2) starting new operating businesses/startups from scratch, and 3) launching direct VC strategies.

According to Deloitte, the number of family offices has grown from 6,130 in 2019 to 8,030 in 2024, with projections reaching nearly 11,000 by 2030. Similarly, aggregate family office AUM is expected to grow from $5.5 trillion today to $9.5 trillion in 2030, a massive $4 trillion increase in just the next five years!

The Paths Available to the Next Generation

An institutionalized fund-of-funds structure creates a unique career path that combines entrepreneurial ambition with professional investment management while preserving family values and long-term orientation.

• Path 1: Traditional Family Business Continuation
  Working within existing family enterprises, often facing constraints of established culture and limited autonomy.

• Path 2: Independent Entrepreneurship
  Starting new operating businesses from scratch, requiring significant operational expertise and capital investment.

• Path 3: Direct VC Strategy
  Building internal VC capabilities through direct investments, demanding extensive resources and specialized expertise that many family offices lack.

• Path 4: Institutionalized Specialist Fund-of-Funds
  Becoming a professional investment platform rather than a generalist allocator that leverages network advantages while accessing institutional expertise, governance, and specialization. Multiple research reports point to a 4-11 percentage point increase in returns for specialists over generalists, likely due to the long-term compounding effects of networks and relationships. This is known as the Performance Premium of Specialization.

Path 4: Pros and Cons

Many family offices will choose to invest directly in companies, akin to building a direct VC strategy. However, recent research demonstrates several challenges family offices face with direct VC investments:

Direct Investment Challenges:

• Only 50% of family offices making direct investments have trained private equity professionals on staff.

• Only 20% of family offices investing directly take board seats and actively engage in portfolio management.

• Deal sourcing remains a primary concern, with family offices struggling to access proprietary deal flow and facing significant adverse selection.

Pros

1. Superior Pattern Recognition and Deal Selection
   Domain expertise enables fund-of-funds managers to identify emerging patterns before the broader market recognizes value creation opportunities. Early pattern recognition manifests in:

   • Enhanced due diligence capabilities through deep understanding of sector-specific value drivers and risk factors.

   • Ability to distinguish between sustainable competitive advantages and temporary market dislocations.

   • Recognition of which fund managers possess genuine operational expertise versus those merely riding sector momentum.

   • Specialized managers consistently demonstrate better capital preservation, with only 14-25% of specialist capital invested below cost, compared to 28-31% for generalists.

2. Privileged Access and Network Effects
   Specialization creates a powerful network flywheel that generalist allocators cannot replicate. Top-tier sector-specific funds increasingly prefer limited partners who understand their strategy and can provide strategic value beyond capital. This leads to:

   • Priority access to oversubscribed funds that regard specialist fund-of-funds as strategic partners rather than passive capital.

   • Co-investment opportunities in flagship portfolio companies, providing additional returns without incremental fees.

   • Early visibility into emerging managers who will define the next generation of sector leadership.

3. Value Creation Through Operational Expertise
   Unlike generalists who primarily focus on portfolio construction, specialists actively contribute to value creation by:

   • Facilitating portfolio company introductions across their specialized ecosystem.

   • Providing access to a talent network for critical executive hires.

   • Offering strategic advisory during pivotal moments such as international expansion or platform acquisitions.

   • Enabling cross-pollination of best practices from concentrated domain expertise.

Cons

While the specialist fund-of-funds model offers multiple advantages, it comes with some inherent challenges that families and investors should consider:

• Narrower Focus Risk: Specialization limits diversification across sectors, which can expose portfolios to sector-specific downturns or regulatory shifts that adversely affect entire industries.

• Dependence on Manager Quality: The model heavily relies on the curation ability of specialist allocator to maintain superior insights and operational expertise. If this declines, performance may lag.

• Potential for Higher Fees: Funds-of-funds will often have layered fee structures, which can erode net returns unless performance substantially exceeds benchmarks.

• Liquidity Constraints: The longer-term nature of private equity and VC may reduce portfolio liquidity, creating challenges for investors seeking flexible capital deployment.

• Scaling Challenges: As family offices grow their specialist fund-of-funds investments, the scarcity of top-performing specialist managers and deals may limit scalability and put pressure on maintaining performance premiums.

Built-in diversification

Counter-intuitively, fund-of-funds provides superior risk-adjusted returns compared to single VC investment yet provides built-in diversification. Additionally, specialists allocators achieve:

• Deeper understanding of sector-specific risk factors, enabling proactive mitigation.

• Ability to distinguish between systematic sector risks and idiosyncratic manager risks.

• More effective portfolio construction within their domain, balancing stage, geography, and strategy while maintaining focus.

In an increasingly complex and competitive investment landscape, the evidence is clear: depth of expertise trumps breadth of multi-asset coverage. Path 4 enables next-generation wealth holders to build professional investment platforms that can compound value for future generations.

Shared Learnings in Firm Building

This transition—from a Family Office to a Venture Capital Firm—is deeply meaningful to me, and I’ve been engaging with peers who aspire to take similar steps. I’m committed to sharing my learnings, highlights, and challenges with the wider community. As part of this commitment, I will continue publishing under the Firm Building Series and welcome reader comments with open arms.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Early stage venture isn’t about spreadsheets or chasing trends. It’s about showing up, building trust, and recognizing that access is the foundation of every meaningful opportunity. At GEX, we treat venture as a network-driven business, not just an investment decision.

The difference-maker for us is simple: access. The best deals don’t circulate in broad emails or on public forums. They move quietly, through trusted introductions and relationships built over time. Reputation means everything. Our commitment to being a value-add partner, acting with honesty, and supporting founders beyond the check, ensures that our network puts us in the right rooms at the right moments.

We don’t see ourselves as passive capital providers. We invest in community, nurture alliances, and share conviction with those who care about long-term impact. The early stage world is small, and trust compounds. Our approach is to invest deeply in relationships, because the power law rewards those who continually earn access to rare, competitive opportunities.

At GEX, sourcing, structuring and selection are not random acts of luck. They’re the outcomes of years of capital deployment, genuine connection, shared values, and relentless curiosity about where we can be most useful. Venture is not just an asset class for us; it’s a community and a platform for multiplying value among those who operate with trust and vision. The real returns are relational. The long game is everything.

If you share our mindset, we’d love to collaborate and build together, because the greatest opportunities always start with a conversation.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

In venture capital, we celebrate the wins, and rightly so, but the real story is rarely told in the opening bell or the final sale price. It’s forged years earlier, in the intricate mechanics of a deal and the trusted relationships that bring it to life.

The recent IPO of Omada Health, our first-ever co-investment with a VC partner, was a major milestone for GEX. More than that, it was a masterclass in how a strategic co-investment, from a Series C entry to a public market exit, truly works. Here are the key lessons from that eight-year journey.

Lesson 1: The Magic of the First Check

Our journey with Omada didn't start with our Series C investment in 2017. It began with a relationship. The opportunity came to us through one of our VC network partners, a manager we had intentionally backed just eight months prior, specifically because of their specialist access and collaborative approach.

This manager wasn't just another investor in Omada; they were the first check in as an angel investor. They had backed the company six years before our investment, establishing a rare and powerful bond with the founders. There’s a certain magic in that first check. It signifies pure, early conviction and creates a level of trust that a company never forgets. When the oversubscribed Series C round came together, it was this trusted partner who brought us the opportunity, validating our strategy of aligning with managers who are true partners to their founders.

Lesson 2: Structure for Alignment, Not for Fees

The mechanics of a co-investment reveal everything about the motives behind it. In a market where many managers see co-investment vehicles as another way to generate fees, this deal was a lesson in true alignment.

The financing was oversubscribed, with participation from strategic players like Cigna, Quest Diagnostics and the world's largest diabetes drug vendor, Sanofi, alongside a roster of top-tier existing investors like Andreessen Horowitz, Norwest, and USVP. Our VC partner committed $5M to the round and offered us a portion of that allocation through a side vehicle. Notably, this vehicle had no management fees and no carried interest for the manager. We were responsible only for our pro-rata share of legal and administrative expenses. The manager wasn't being greedy by monetizing the side vehicle; their goal was to show continued support for the company. They would only win if the company became a breakout success. This is a critical lesson we carry forward: the best partnerships are built on shared success, not fee generation. It’s a principle that seems to be reversing in the current market, making us even more steadfast in our approach.

Lesson 3: Selection for the Long Haul

With sourcing and structure aligned, the final piece was selection. We saw a company hitting its stride, bolstered by our own interest in digital health and the tangible IoT angle of its connected scale, which created a powerful data-driven feedback loop for users.

Our diligence confirmed Omada's strengths: a clinically-validated product, explosive revenue growth, and powerful strategic buy-in. The round was led by Cigna, a major healthcare player, whose decision was driven by outstanding feedback from their own employees using the platform. As part of the investment, Cigna also entered into a large partnership to dramatically expand Omada’s reach across its network of covered lives, providing significant upside beyond the company's already impressive organic growth. With a roster of top-tier existing investors also participating, the signal was clear: this was a category-defining company on a path to a major exit.

This journey, from a 2017 co-investment to a 2025 IPO, has been a testament to our strategy. It reinforces our belief that the best opportunities are sourced through trusted, long-term relationships and that the soundest investments are built on a structure of shared success.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Let’s begin with a status check:

June 2025 may go down as the month when autonomous vehicles (AVs) finally crossed the psychological chasm from “promising tech demo” to “everyday infrastructure.”

• Waymo’s Multi-City Reality: The company is quietly expanding fully driver-out service in four additional metros and growing its coverage in existing ones, pushing its annualized run-rate to >400 million robotaxi miles. Even San Francisco’s new mayor, Daniel Lurie, hailed a Waymo on Market Street and livestreamed the ride.

• Tesla’s First Self-Delivering Car: A Model Y rolled off Gigafactory Texas, drove 30 minutes on public roads, and parked in its new owner’s driveway—no human intervention, first insurance-approved autonomous delivery ever.

The trajectory is clear. Just as smartphones transformed from luxury gadgets to essential infrastructure in less than two decades, AVs will become a daily reality by 2040. The same psychological shift that made us forget how we navigated cities before Google Maps will happen with autonomous transportation.

From AVs to GenAI

AVs were the first commercial arena that demanded all of AI’s pieces: perception, prediction, planning, high-performance computing, advanced software tooling and hardware integration that needs to be safe and work flawlessly 24/7. That pressure forged several breakthroughs that now power today’s broader AI boom:

• Perception at the edge: billions of annotated camera, lidar, and radar frames built the world’s largest real-world vision datasets, forcing innovation in neural-network compression, low-latency inference, and specialized silicon.

• Synthetic data & large-scale simulation: AV teams pioneered photorealistic simulators to generate rare or dangerous scenarios safely, a technique now standard for robotics and embodied AI which is now extending to “world modelling”.

• Continuous learning in the wild: maintaining a fleet taught engineers how to collect, label, and re-train models on petabytes of fresh data every day, laying the blueprint for modern MLOps.

• Regulation & safety: nobody faced a tougher regulatory and liability bar than companies putting 4,000-pound robots on public roads. The resulting processes of safety cases, formal verification, redundancy engineering are becoming the gold standard for any AI product.

AV Talent

One of the most remarkable outcomes of the AV revolution is the caliber of talent it has cultivated. Because AVs sat at AI’s bleeding edge, they magnetized elite engineers, roboticists, and product builders. The decade-plus commercialization slog, full of dead-ends, opaque regulations, and brutal capital cycles, left this cohort with hard-won judgment and plenty of scars. Now, as the industry matures, many of these leaders are channeling that experience into fresh challenges, becoming founders, investors, and builders:

• Founder-to-Founder Transitions: Cruise Automation founder Kyle Vogt is already applying AV know-how to humanoid robots, raising $150 M on day one .

• Investor Migration: AV alumni are launching venture funds and backing the next generation of ambitious startups. GEX is actively investing in these funds, such as LMNT Ventures (founded by a core Uber ATG member) and Reasons to be Optimistic (led by Oliver Cameron, founder of Voyage).

• Cross-Pollination: The skills and mindset honed in AV to solve complex, high-stakes problems at scale are now being applied to cognitive AI and beyond.

For GEX, the investment thesis is clear: follow the talent. Whether these AV veterans become founders of the next breakthrough companies or investors backing the next generation of entrepreneurs, their involvement signals opportunities worth pursuing.

I’ll leave you with some background material. For a definitive insider history, pick up Autonomy: The Quest to Build the Driverless Car—And How It Will Reshape Our World by Lawrence D. Burns, former GM R&D chief and early Waymo adviser. The book traces the field from the DARPA Grand Challenge through the 2016 stampede into commercial development, profiling the maverick engineers and unlikely thinkers who pushed the technology forward. If you’d rather watch than read, Burns distills the same story in a lively, hour-long Talks at Google session.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Companies are opting to stay private longer (SPL). 87% of US companies with revenues greater than $100 million are not traded on public stock exchanges such as NYSE or NASDAQ.

In this post, we examine some stats, potential reasons for SPL, and what it means for non-institutional investors.

Facts and Trends

• 6 vs 11 years: In 1980, the median age of a company at IPO was 6 years; by 2021, it was 11 years.

• $100m vs $1.3b: In 1980, the median market value at IPO (inflation-adjusted) was $105 million; in 2021, it was $1.33 billion.

• 6.5k vs 3k: From 1980–2000, there were over 6,500 IPOs. From 2001–2022, fewer than 3,000—even with the 2021 frenzy.

The number of public companies in the US has fallen from 7,500 in 1997 to under 4,000 today, while the average age at IPO continues to rise. The result: the bulk of innovation and value creation is happening off the public markets, behind the velvet rope of private capital.

Why Are Companies Staying Private Longer?

Company Side

• Regulatory burden: Sarbanes-Oxley and other rules have made public company life more expensive and distracting for management.

• Abundant private capital: Private equity and venture funds now manage trillions in assets. In 2023, private equity funds managed $8.2 trillion, more than double 2018’s total. Companies like SpaceX, OpenAI, and Stripe have raised billions privately and reached valuations that would place them among the largest public companies—if they chose to list.

• Control: Staying private allows founders and early investors to retain control, avoid quarterly earnings scrutiny, and focus on long-term strategy.

Market Side

• Investment bank economics: IPOs are expensive—banks charge 7% fees on gross offering, though large deals sometimes negotiate down to 1–3%. For a $1 billion offering, that’s $21 million in fees.

• Risk aversion: Banks used to underwrite (“firm commitment”) IPOs, taking on risk. Now, they’re more conservative, and direct listings or SPACs have emerged as alternatives.

• Private market liquidity: The rise of secondary markets means early investors and employees can cash out before an IPO, reducing pressure to list.

What It Means for Investors

The implications are stark:

• Missing the growth curve: The most explosive growth now happens before IPO. By the time companies go public, much of the upside has already accrued to private investors.

• IPO risk: The data is sobering—80% of IPOs are unprofitable at debut, and two-thirds underperform the market within three years. Recent high-profile IPOs like Uber, SmileDirectClub, and Robinhood saw their shares fall sharply after listing, often never recovering to private market valuations.

• Liquidity gap: With fewer IPOs and longer holding periods, public investors have less access to innovation and growth. Meanwhile, private market investors must navigate longer holding periods and more complex exit dynamics.

What It Means for VC LPs

For us, as allocators, this means adapting to a new reality. We see two scenarios:

1. Continuation of the SPL trend (80% probability): Private markets continue to dominate, with public markets becoming less accessible for new companies and investors seeking innovation.

2. Regulatory reversal (20% probability): A shift in regulation makes going public easier, swinging the pendulum back and opening the door for earlier IPOs.

Our strategy is shaped by these probabilities. The late-stage private and pre-IPO markets are crowded, expensive, and often deliver subpar returns for new entrants. Uber is a textbook case: by the time it went public, the exponential growth was over, and public investors bore the brunt of the risk while early investors had already cashed out.

“What seemed like a great opportunity to invest in a huge company turned out to be a case of getting on the elevator on the top floor.”

Therefore, we focus on the early stage, where value creation is greatest—but sourcing and access are the real challenges. We solve for this by investing as a fund of funds, partnering with specialist managers whose sole job is to find and back the best opportunities as early as possible.

The Evolving Private Market Playbook

Private markets themselves are evolving. The rise of the secondary market means that liquidity options are improving for early investors, founders, and employees—even as companies stay private longer. This is changing the venture capital model from “buy and hold” to active portfolio management, with secondaries and continuation funds now an essential part of the toolkit.

Meanwhile, LPs are increasing allocations to private markets, especially in technology and healthcare, and are seeking exposure through co-investments, secondaries, and sector-specific microfunds. The innovation supercycle—driven by AI and digital transformation—means the best opportunities will continue to emerge privately, not on the ticker tape.

The New Center of Gravity: Silicon Valley

This shift is part of a larger secular move away from traditional financial centers like New York and London toward Silicon Valley. Not only is the Valley the epicenter of company formation, but it’s also become the capital market for growth businesses. The culture, capital, and networks for scaling technology companies are all here, and the role of venture capital in driving innovation has never been more pronounced.

For family offices investing in VC funds, the path to top-tier opportunities increasingly runs through strong relationships and showing up! By pairing fund commitments with selective co-investments and SPVs, family offices can access high-conviction deals and deepen their exposure to innovation.

The key: build trusted networks with leading managers, stay disciplined in diligence, and bring your unique expertise or connections to the table. In today’s private market environment, those who are engaged, connected, and nimble will capture the best opportunities—well before they ever hit the public markets.

This is an educational post about GEX Ventures family office. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Every Challenge Is a Teacher: Choosing to Live Above the Line

In conscious leadership, being above the line means approaching life from openness rather than defensiveness, curiosity rather than judgment, and a deep commitment to learning rather than complacency. It means seeing emotions and challenges not as obstacles but as signals-inviting us to grow. This mindset is the key to feeling truly present and appreciating the unique value of each moment.

Practicing this shift has transformed how I face adversity. When I encountered some of the toughest challenges in my life-moments I once saw as setbacks or even endings-I learned to pause and ask, “What is this teaching me?” Choosing curiosity and openness turned those very challenges into launchpads for deeper fulfillment and meaningful work. Moving from resistance to learning changed everything.

At 27, I had methodically checked off every goal I set for myself-but I wasn’t happy. Something was missing. That’s when I faced a difficult question: Should I settle for the good I had, or give it up to pursue something truly great?

Rockefeller’s Wisdom: Don’t Be Afraid to Give Up the Good for the Great

John D. Rockefeller famously said, “Don’t be afraid to give up the good to go for the great.” This isn’t just about business or success-it’s about mindset. It takes extreme curiosity and a commitment to learning to let go of what feels safe and “good enough,” trusting that something greater awaits.

This leap demands courage, humility, and a willingness to embrace uncertainty. But it’s precisely this mindset-being open, curious, and committed-that turns every person and situation into a teacher and every challenge into an opportunity.

My Decision: Resetting the Bank and Rebuilding with Purpose

I made the difficult choice to return the money my family had provided me, effectively resetting the bank-and maybe the clock. I decided to rebuild not for myself, but for my family and community first. This decision gave me more than reward or duty-it gave me love and purpose.

I began to love my work every day because it was rooted in serving others through investing. That single choice to give up the good for the great became an evergreen source of energy that propels me forward and keeps me motivated.

If you haven’t experienced a similar voluntary (or even forced) loss, it’s hard to fully convey the feeling. But this mindset of conscious leadership gave me a practical framework to navigate it, and I’m deeply grateful for that.

If you’re curious about this approach, I’d be happy to share more about my journey and how it shaped me into a stronger, happier, and more fulfilled person. Feel free to email me. I welcome the conversation.

This is the sixth in a series of posts about my experience with Conscious Leadership. Here are the previous ones: 1, 2, 3, 4, 5. Email me at mk@gex.vc or leave a comment if you’d like to discuss further.

In previous posts, we discussed the idea of GEX and what it stands for: Generational Entrepreneur Experience as well as founders who’d like to re-create wealth after a win. In this post, we’d like to explore the philosophy behind winning and how to transfer the experience of winning across generations through investing in value creation.

Experience has always been the cornerstone of the firm we’re building. In an era increasingly shaped by AI, understanding the depth and nuances of human experience is more critical than ever. Experience is multifaceted and uniquely personal, shaped by historical context, family legacy, practical learning, and evolving values. By acknowledging these dimensions, investors can better understand how founders adapt to challenges and seize opportunities.

Experience differs fundamentally from memory: while memory is a collection of past events, experience is a collection of sensations. It is this sensation that drives performance and sustains it day after day.

We’ve spent considerable time reflecting on how to capture and transfer this sensation across generations. While direct experience is irreplaceable, stories often serve as a bridge to convey its essence. Yet, the closest we’ve come to replicating this sensation is through the feeling of winning, investing in winners and sharing in their success. These sensations and victories translate into value delivered via a venture capital network, a federated ecosystem of top-performing investors, and often former founders themselves, united by a singular mission: to help the next generation of founders succeed.

As part of this journey, we’re also refining our tagline to encapsulate this philosophy. One promising option is "Learn, Live, Lift." This phrase captures a powerful progression of growth and impact:

• Learn it: The foundation of growth lies in curiosity, the drive to acquire knowledge, skills, and insights. Successful investors and founders are often the most curious individuals you’ll meet.

• Live it: Learning comes alive through action. Embodying knowledge by putting it into practice creates transformative experiences. The act of starting something from scratch while embracing uncertainty and risk is irreplaceable.

• Lift it: The culmination of learning and living is using that experience to elevate others. This means sharing knowledge, inspiring peers, empowering communities, and raising standards for those who follow.

This cycle of learning, living, lifting is what makes Silicon Valley extraordinary. It’s woven into the fabric of its culture: the relentless drive to innovate while uplifting others has created a self-sustaining ecosystem that feels magical in its impact.

We’re applying this concept within the context of families and individuals investing in Silicon Valley with an elevated purpose: creating value today while recreating the experiences that fueled past successes for future generations. This encapsulates the essence of generational entrepreneur experience—building a legacy that not only endures but thrives across time.

This is an educational post about GEX Ventures family office. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

I previously wrote about the move away from globalization. Here we'll explore our evolving view of entrepreneurship from a global perspective to a generational one, reflecting on key events that have shaped this transition and its implications for the future of business and innovation.

From global to generational

The world has witnessed a significant shift away from the globalization paradigm that dominated economic thinking in the past few decades. Three major events have catalyzed this change:

1. Brexit: The UK's decision to leave the European Union

2. COVID-19 Pandemic: Global shutdowns and supply chain disruptions

3. Russia-Ukraine War: Geopolitical tensions and economic sanctions

These events have fundamentally altered our perception of free trade and the unrestricted movement of people and ideas, which were once considered unassailable pillars of economic growth.

In May 2017, two years into startup investing, I wrote about GEX’s belief in the global nature of entrepreneurship:

While we still believe in the above statement, our approach has evolved. GEX, originally standing for "global entrepreneur experience," now represents "generational entrepreneur experience." This shift reflects a change from a geographic focus to one of stewardship and ambition, emphasizing entrepreneurial success and the resulting experience across generations.

Replicating Silicon Valley

After China cracked down on its consumer internet startups back in H2 2020, I wrote a piece about the type of startups we should be funding and how a very different lens on entrepreneurship versus that formed in Silicon Valley changes outcomes. In that piece, I wondered what should be considered “real tech” and urged the reader to check whether the $288b that had been invested by VCs in H1 2020 was going to create lasting value.

Contrast that period of excess and different type of entrepreneurial outcome to what a16z coined American Dynamism later in 2022. In that piece they concluded that “American dynamism is the belief that the values upon which the country was founded are real and worth defending.” Many people have taken American dynamism at face value which could be seen as defense-tech but in my opinion it is about building companies aligned with what makes Silicon Valley (and the US) the center of generational entrepreneurial success. Behaviorally, it means “optimism and a belief in growth and opportunity”. It could also be seen as what Peter Thiel dubbed Determinate Optimistic vs. Indeterminate Pessimistic Futures, i.e. The American Dream vs. blindly replicated startup ecosystems.

Generational Entrepreneur Experience

By reframing GEX as the "generational entrepreneur experience" we aim to:

1. Promote fundamentally positive and optimistic values for future generations

2. Move away from an absolutist view of global entrepreneurship and create a network of like-minded innovators, regardless of their physical location

3. Attract self-selecting entrepreneurs who resonate with the "American Dream"

I’ve personally been working towards this alignment for a decade, a journey I deeply cherish. I feel lucky that this journey is allowing me to contribute to the success of generational entrepreneurship and better understand the resulting experiences.

This is an educational post about GEX family office. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

During a recent dive into Albert Wenger’s The World After Capital, I learned why attention—the intentional allocation of our time—has become humanity’s ultimate scarce resource. This isn’t just philosophical musing; it’s an urgent economic reality. Wenger’s framework dovetails strikingly with Peter Diamandis’ Abundance, a book I read years ago that argued technology could turn scarcity into plenty, as it did with aluminum post-electrolysis. Today, we’re witnessing a parallel revolution: the plummeting cost of cognition through AI. Yet unlike aluminum, attention resists abundance—and its mismanagement threatens to derail progress.

Social media’s rise exposed this vulnerability. From the mid-2000s onward, platforms weaponized attention, monetizing every scroll and click. The consequences—fragmented discourse, eroded mental health, algorithmic radicalization—linger like digital hangovers. Now, as AI turbocharges productization of cognition, we’re entering an era of mass cognition monetization. This is where value systems clash openly because cheap cognition lets groups amplify their ideologies through endless attention channels.

Yet the stakes transcend culture wars. Gaia Vince’s Nomad Century—next on my reading list—warns that climate-driven migrations will redraw maps and test societies. We’re already seeing microcosms in front of our eyes: Los Angeles neighborhoods displaced by wildfires and people stranded but their attention fractured between survival and sustainability. This mirrors Wenger’s broader thesis: To navigate existential risks (climate collapse, AI ethics, synthetic biology), we must transition from an Industrial Age mindset to a Knowledge Age paradigm—one where automation frees 80% of human attention for creativity and problem-solving.

The inflection point is here. Technology now evolves faster than our ability to govern it or even harness it without side effects. Therefore, focused attention isn’t just valuable—it’s existential. The challenge? To harness abundance without losing our humanity to the very tools we’ve built.

The path forward demands rigor: audit where your attention flows, align it with ethical systems, and remember—every click, every hour, every mental investment shapes what abundance means.

This is a post about ecosystem resources which was also posted on Medium. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

One year ago, I shared my plan to replace certain functions of LinkedIn using a combination of AI tools, personal networks, and event-based networking1. At the time, I identified several areas where LinkedIn seemed to fall short—especially in generating genuine connections or deal flow—and I became increasingly skeptical of its actual value to my workflow. This past year has been an ongoing experiment to find more targeted ways to engage with my community, share content, and discover new relationships. Here is what I’ve learned so far.

Networking

While I haven't found a direct, one-to-one replacement for LinkedIn, my exploration has led me to a diverse array of tools and strategies that have collectively enhanced my professional networking and information gathering.

I've experimented with services like People Data Labs, which offer robust APIs for accessing professional data. These tools have provided a more targeted approach to finding and connecting with relevant professionals in my industry.

Perplexity AI has become an invaluable resource, offering deeper, more contextual insights than traditional search engines. This AI-powered tool has helped me gather comprehensive information on companies, trends, and individuals more efficiently than scrolling through LinkedIn feeds.

Surprisingly, X.com (formerly Twitter) has proven to be a powerful complement to my networking strategy. It offers a more dynamic, real-time view of professionals' thoughts and activities, providing fuller context beyond the static career timelines typical of LinkedIn.

Content sharing

I've completely migrated my professional writing from LinkedIn to Substack. This move has allowed for:

• More in-depth content creation

• Direct engagement with a dedicated audience

• Better control over content distribution

To manage the influx of information without LinkedIn's feed, I've implemented a new system:

• Created specific folders in my email inbox for topics of interest

• Curated a selection of high-quality newsletters

This approach has resulted in more focused and relevant information consumption, eliminating the noise often found on social media platforms.

Reflections and Future Outlook

The area where I've made the least progress is recruiting. As I didn't have to hire directly in 2024, I haven't fully tested AI-driven alternatives for this crucial function. This remains an area for future exploration and development.

One of the most rewarding aspects of this experiment has been the renewed focus on personal networks and face-to-face interactions. Over the year, I took 24 business trips to meet with people I wanted to work with in person. This enabled me to attend more in-person meetings, which led to deeper and more meaningful connections. Additionally, I intentionally leveraged close personal networks, resulting in high-quality introductions and partnerships.

This year-long experiment has reinforced my belief that professional networking and information gathering can be more effective when personalized and decentralized. While LinkedIn served as a valuable tool in the past, this new approach has led to:

• More meaningful professional relationships

• Higher quality, targeted information gathering

• A more balanced approach to online and offline networking

I will keep refining this approach. The integration of AI and APIs will continue to evolve as these technologies advance, while personal connections will remain at the heart of my professional endeavors. For anyone considering stepping away from traditional platforms like LinkedIn, I encourage you to explore alternatives that align with your specific needs—and don’t underestimate the power of offline relationships.

Thanks for following along on this journey! If you have thoughts or questions about these experiments—or if you’re navigating similar transitions—I’d love to hear from you. Let’s keep the conversation going!

This is a post about ecosystem resources which was also posted on Medium to benefit founders and investors. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

When I first wrote about the concepts of motivation and ikigai in 2018, I couldn't have predicted how they would shape my entrepreneurial and investing journey. Finding purpose by applying this framework to my work has not only provided immense satisfaction but also guided the evolution of our strategy at GEX. Today, I want to share how these insights have culminated in our fund of funds approach.

Revisiting the Four States of Motivation

In my original exploration, I identified four states of motivation: fear, reward, duty, and love. These states, when considered through the lens of ikigai, offer a powerful framework for understanding what drives us and how we can achieve true fulfillment. In my 2022 update, I reflected on how these motivation states presented themselves at that point in my journey.

Fear: The Catalyst for Change

Fear can be a powerful motivator, especially in entrepreneurship where the fear of failure often propels founders to take their first leap. However, to create something truly meaningful, it is essential to move beyond fear and embrace more sustainable motivators.

Reward: The Double-Edged Sword

The pursuit of success and material rewards aligns with the ikigai aspect of "what you can be paid for". Yet, true fulfillment arises from balancing financial success with personal satisfaction and societal contribution.

Duty: The Bridge to Purpose

Duty resonates strongly with ikigai, embodying the idea of contributing to society and fulfilling responsibilities. It is about finding purpose in serving others and doing what's right, stemming from a place of self-awareness and the unique value one can bring to the world.

Love: The Heart of Ikigai

Love is perhaps the closest motivator to the essence of ikigai. It encompasses passion for what you do and a desire to make a positive impact on others on a sustainable basis.

The Importance of Each Ikigai Element

Passion: What You Love

Without passion, our efforts lack energy and enthusiasm. A strategy devoid of passion feels mechanical and uninspired, failing to ignite the drive needed for innovation and perseverance.

Mission: What the World Needs

If mission is missing, our work lacks direction and purpose. A strategy that doesn't address real-world needs can feel irrelevant and disconnected from broader societal goals.

Profession: What You Are Good At

Without leveraging our strengths (profession), we risk inefficiency and mediocrity. A strategy that doesn't align with core competencies may struggle with execution and fail to achieve desired outcomes.

Vocation: What You Can Be Paid For

If vocation is absent, sustainability becomes an issue. A strategy that isn't financially viable may falter over time due to lack of resources or support.

Overlaying Ikigai on to The Fund of Funds Approach

The fund of funds approach, when viewed through the lens of ikigai, offers a powerful framework for creating meaningful impact in the venture capital ecosystem. By aligning passion (what we love), mission (what the world needs), profession (what we're good at), and vocation (what we can be paid for), we can create a strategy that not only generates strong financial returns but also fulfills a deeper purpose: solving problems for entrepreneurs on a suitably long-term basis amplified through a network of VC networks. This overlay allows us to select funds that resonate with our values, support entrepreneurs who are driven by meaningful missions, leverage our expertise in fund selection and management, and create sustainable value for all stakeholders involved.

Long-Term Vision

Venture capital is not just an investment; it's a commitment to a long-term vision that seamlessly integrates all elements of ikigai. It's a journey where the passion for innovation meets the unwavering mission of founders. This approach fosters professional competence and ensures that financial success becomes the foundation for sustained growth and lasting impact. Imagine a future where your investments are not just financial transactions but profound partnerships that shape the world.

Problem Solving Mindset

At its core, our fund of funds strategy needs to solve problems for entrepreneurs. By investing in multiple venture capital funds, we gain access to a diverse array of insights and expertise that allows us to address the multifaceted challenges faced by startups, from Silicon Valley to the farthest reaches of the globe. Our approach, adaptable and responsive to emerging trends and needs, enables us to support innovative solutions tailored to the unique challenges of each entrepreneurial venture.

Network of Networks

At the heart of our strategy lies a commitment to fostering connections within the most impactful people in the tech community. With a renewed focus on Silicon Valley, we're not just creating a network; we're building a high quality network of VC networks. In a world where entrepreneurs, investors, and visionaries come together in a well structured legal and financial mechanism, sharing knowledge and insights on a broad scale becomes practical and quite powerful. This is our vision, and through our fund of funds approach, we're making it a reality.

Conclusion: Finding Your Ikigai in Entrepreneurship

As we continue our journey at GEX, we remain committed to fostering an alignment for entrepreneurs and investors worldwide. Because when we find our ikigai in business—and ensure all elements are present—we don't just build successful companies; we create meaningful change and lasting impact.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

Over the past decade, I've been deeply immersed in the world of global entrepreneurship, both as an investor and as an immigrant founder myself. Having lived across three continents and five countries, I've gained unique insights into the challenges and opportunities that come with building businesses and networks in new environments. While the narrative around immigrant entrepreneurship has gained traction in recent years (I’ve spoken to 20 VC funds with this thematic approach in the last 6 months), I've come to realize that simply focusing on this theme as an investment strategy is no longer enough to provide a meaningful edge in today's competitive landscape.

Beyond the Immigrant Entrepreneur Narrative

When we launched GEX in 2015, we were driven by the conviction that entrepreneurship propels humanity forward and that we could play a part in empowering global entrepreneurs. However, as the ecosystem has evolved, it's become clear that investors need to demonstrate a more nuanced understanding of how immigrant entrepreneurship translates into tangible advantages. After numerous conversations and deep analysis of the immigrant-focused investor-founder landscape, coupled with my own lived experience, I’m boiling down the investable theme of immigrant entrepreneurship to three key constituting factors:

1. Market and Capital Access: The Real Competitive Advantage

Traditionally, a key area where immigrant entrepreneurs have provided unique value is in building corridors for market access, especially for large market pairs such as US-China and US-India. I have observed that successful immigrant-led startups often leverage their dual cultural understanding to bridge markets. However, in a world where cross-border opportunities are becoming more difficult to assess and access, VCs who want to support immigrant entrepreneurs need to clearly demonstrate their edge in providing market and capital access opportunities to their portfolio companies.

2. Talent and Geographic Arbitrage

Another critical factor is the ability to tap into global talent pools and leverage geographic arbitrage for capital efficiency. Immigrant entrepreneurs often have access to high-quality, cost-effective talent in their countries of origin. Investors who can help startups navigate the complexities of building distributed teams across borders will be well-positioned to capitalize on this trend. At the same time, founders who have been successful in their countries of origin may bring cultural nuances to their destination market that are not necessarily conducive to their success. A successful VC will be aware of these differences and will handle them upfront. Here, generalist immigrant investors are at a disadvantage since diaspora communities are becoming stronger. See my next point.

3. The Rise of Diaspora Tech Communities

Perhaps the most exciting development I've witnessed is the growth of diaspora tech communities. These networks are becoming powerful engines of innovation and collaboration, transcending traditional geographic boundaries. In spite of the challenging political currents against global entrepreneurship, we've seen firsthand how these communities can accelerate startup growth and provide invaluable support systems. Therefore, as backers of immigrant entrepreneurs, VCs should really ask themselves why they are the top choice for entrepreneurs when much more specialized diaspora communities exist.

A New Paradigm for Investing in Immigrant Entrepreneurs

As we move forward, investors focusing on immigrant entrepreneurship need to evolve their approach. It's no longer enough to simply identify talented immigrant founders or cite statistics showing that more than half of unicorns have been founded by immigrants. The real edge lies in understanding how to:

1. Facilitate U.S. market entry

2. Optimize global talent strategies

3. Tap into and amplify diaspora tech networks

GEX: The Global Entrepreneur Experience

Our approach at GEX goes beyond surface-level thematic investing to provide deep, actionable support for entrepreneurs via a network of investors. We are carefully selecting top U.S.-based VCs who can clearly show their edge in at least two of the three areas mentioned above.

I wanted to wait for the much-anticipated U.S. election results before publishing this post. We still believe that the future of global entrepreneurship is bright and that successful founders and startups are default-global, but it requires a new level of sophistication from investors who want to truly empower immigrant entrepreneurs. Those who can rise to this challenge will be well-positioned to capitalize on the immense potential of immigrant-led innovation in the years to come—and it will be our privilege to partner with them.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

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A few years ago, I wrote a post about the economics of AI depicted through a value Seesaw seen below (the post was for a company that was eventually acquired by Applied Intuition, a pioneer in applying AI in the automotive industry).

It’s incredible to see how AI adoption has increased and changed perceptions of its impact in the near future but I believe that the fundamental value drivers remain the same. The economics of AI continue to revolve around the concept of prediction as a key input in many business activities and our daily lives. As AI technology advances, it's causing a significant drop in the cost of prediction, which in turn is reshaping various industries and creating new opportunities.

Three main AI complements that are becoming increasingly valuable are:

1. Data

2. Judgment

3. Action

As AI improves its predictive capabilities, the value of human prediction decreases, while the importance of data, human judgment, and human action increases. The above graph from the folks at Forerunner shows where the value of such human judgment will increase whereas the processes of applying human knowledge can be automated. This shift is particularly evident in knowledge-based industries such as legal, financial, and healthcare services.

The "Selling the Work" Model

Initially, many AI companies focused on "selling the work" - providing AI-generated outputs to service providers, think labelling and annotation of images which is essentially replacing human perception to automated legal document review which is replacing human information processing.

However, this model faces challenges as AI technology becomes more accessible and commoditized. As a result, the arbitrage opportunity that currently exists between AI-generated work and human labor is likely to collapse. The most successful AI-powered services firms will be those that prioritize the human element alongside AI capabilities, the good old augmented intelligence rather than artificial one. You’d need fewer people to do the the task but it will still require human touch.

These firms recognize that while AI can handle a significant portion of knowledge work, many industries still require human judgment, trust, and credentialed individuals to deliver services effectively. To assess AI-readiness and how it can affect a certain organizational process, think about various factors, including:

1. The intended use of AI in the business

2. The nature of the business

3. Organizational workflows and tasks

4. Potential return on investment

For businesses scoring high on AI-readiness, the next step involves breaking down workflows into tasks and identifying those with significant prediction components that could benefit from AI implementation. If the budget assigned to prediction can be substantially reduced using AI, then the company is 100% ready. It then becomes a buy vs. build decision. Since the speed of development in AI is blazingly fast the answer to that question is buy in almost all cases.

The Future of AI-Powered Services

As AI technology continues to advance, we can expect to see more AI-native services firms emerging. These firms will likely:

1. Prioritize AI implementation at every stage

2. Organize expert employees to focus on work that AI can't replace

3. Align business model incentives more productively

4. Establish cultures that are risk-tolerant and aspirational

The most successful AI-powered services firms will not just sell AI tools to existing companies but will become the next generation of industry leaders in their respective fields. Perhaps we will see the first billion-dollar solo-entrepreneur building such a business.

This is an educational post about GEX Ventures investments. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.

At some point, most successful entrepreneurs start to think about setting up a family offices to manage their wealth. However, they often face a unique challenge when it comes to wealth "re-creation" and not just preservation. Here, we examine the difficulties successful entrepreneurs or wealth creators face in replicating their initial success after exiting their primary business venture and explore optimal strategies for overcoming these challenges.

The post-exit doldrum

I had previously wrote about the struggles with post-exit decision making. Adding to that post-exit doldrum, a wealth creator faces several unexpected setbacks that adds to the struggle:

• Identity Crisis

Many entrepreneurs struggle with a loss of identity after exiting their business. The company that once defined them is no longer a part of their daily life, leading to a period of uncertainty and self-reflection.

• Changed Market Dynamics

The business landscape is constantly evolving. Strategies that worked in the past may no longer be effective, requiring entrepreneurs to adapt and learn new skills.

• Risk Aversion

With financial security achieved, some entrepreneurs become more risk-averse, making it challenging to take the bold steps necessary for creating another successful venture.

• Shifting Priorities

As wealth creators transition from building businesses to managing family wealth, their priorities and risk tolerance often shift dramatically. The responsibility of preserving wealth for future generations can lead to more conservative investment strategies, contrasting sharply with the high-risk, high-reward approach that defined their entrepreneurial journey.

• Time Allocation

The demands of family life can significantly reduce the time and energy available for new ventures. Entrepreneurs who once worked around the clock may find themselves prioritizing family time over business pursuits, making it challenging to recreate their initial success.

Succession planning: balancing wealth re-creation and family demands

Succession planning is a critical aspect of family office and family wealth management, ensuring the continuity of wealth growth and family values across generations. Starting succession discussions well before significant decisions need to be made is crucial. This allows for a smoother transition and reduces stress on family members when unexpected events occur.

Effective succession planning in family offices involves much more than just deciding who takes over when the sensitive subject of retirement comes up. It encompasses:

1. Identifying and Preparing Future Leaders: This includes pinpointing potential leaders within the family and preparing them for their roles through education, mentorship, and gradual involvement in decision-making processes.

2. Legal and Financial Structuring: Setting up trusts, wills, and other estate planning tools to ensure a smooth transition of assets.

3. Family Governance: Establishing clear roles, responsibilities, and decision-making processes to prevent conflicts and ensure smooth operations.

4. Wealth Transfer Strategies: Implementing tax-efficient methods for transferring wealth to the next generation.

5. Family Education: Preparing younger family members for the responsibilities of wealth management and fostering a shared understanding of the family's values and mission.

6. Addressing Generational Differences: Creating opportunities for the new generation to gradually participate in investment management and decision-making processes, especially when older family members are reluctant to delegate responsibilities.

Strategies for Successful Wealth Re-creation and Succession

1. Redefine Success: Embrace a broader definition of wealth that includes not just financial capital, but also human and social capital.

2. Set New Goals: Establish clear objectives for both business and family life, revisiting them regularly.

3. Implement a Bespoke Operating Model: Design and implement a target operating model that aligns with the family's vision, purpose, and generational needs.

4. Leverage Technology: Utilize software and technology solutions to optimize family office operations, from portfolio management to governance and document management.

5. Continuous Learning: Stay abreast of the latest trends, best practices, and regulations through specialized courses, conferences, and networking events.

6. Seek Expert Advice: Engage with family office advisors who can provide strategic guidance on wealth management and legacy preservation.

By addressing these challenges and implementing comprehensive strategies, wealth creators and family offices can better navigate the complexities of wealth re-creation and succession planning, ensuring the preservation and growth of family wealth across generations.

In future posts, I'll share some of our experiences with these topics.

This is an educational post about GEX Ventures family office. It is for informational purposes only and may not be relied on as legal, tax, securities or investment advice and does not constitute an offer to buy or sell interest in any products offered by us or others. Email me at mk@gex.vc or leave a comment if you’d like to exchange ideas.