Why you do not need to conquer every mountain (or raise that fund)

This week I came across a Wall Street Journal article about climbers inhaling xenon gas to summit Everest in record time.

It reminded me of a recent hike up Grouse Mountain in Vancouver, where I overheard fellow hikers bragging about hitting 190 bpm heart rates as they sprinted past. My companion and I took a different approach — steady, calm, and surprisingly effortless (OK, maybe that’s a bit of hyperbole).

We reached the top with energy to spare and noticed a sign inviting people to take a photo next to their finish time.

I found it odd.

In all my hikes — from Zion in Utah to Lion’s Head in Cape Town— I had never seen such a performative relationship with nature. I was usually too busy taking in the spectacular sights and sounds to think about conquering them.

It made me wonder: are we missing the point?

Just because you can run up a mountain does not mean you should.

The same holds true for startups.

Just because capital is available does not mean you are ready to take it, or that it is the right kind of fuel. That is what we are exploring in this week’s newsletter.

💥The New Venture Playbook: Why Fund I Might Be Your Last

In my recent conversation with the COO of Sydecar, a platform powering SPV (special purpose vehicle) infrastructure behind the scenes, we dug into a quiet shift reshaping early-stage venture capital.

12 years ago, he was writing about companies staying private longer. That part has not changed. What has?

It’s not only the bar for IPOs that’s getting increasingly higher. “The higher bar and expanded timeline to go public has put pressure on liquidity - for founders, employees, and early investors,” he shared. “As a result, we've seen these stakeholders increasingly turn to the private secondary markets as a pressure valve."

So what does this mean for the venture capital and startup industry overall? Let’s dig in.

💡 The new Fund I is… no fund at all?

Raising a debut VC fund is harder than ever. Emerging managers are on track to have their worst raising year in recent memory.

This affects me personally, since I work at a fund that is a considered an emerging manager.

But for those with audience and access, SPVs have become a scalable alternative.

Emerging managers are skipping traditional fund structures altogether, building track records and LP relationships deal-by-deal. You can thank (or blame) the high cost of fundraising and the power of online distribution.

The rapid pace of tech innovation drastically compressing costs and removing barriers to entry can’t be understated. Much like Vanguard powered a revolution in retail investing, SPVs are emerging as tool that democratize access to private asset classes like venture capital.

💸 Liquidity defines strategy

VCs used to count on IPOs to deliver returns. Today? That door is basically closed.

Founders continue to keep their companies private for longer. Before, the common wisdom was 7 - 10 years before an IPO.

Now?

Good luck going public, especially with the recent underperformance of high flying companies. Even Hinge, whose IPO was recently feted by the LinkedIn gliteratti, had to face the realities of a public markets down round.

(💡Side note: when I worked with emerging markets public equities, one common “risk” highlighted was the small number of publicly traded companies on exchanges in Latin America and the African continent, driven partially by the lack of IPOs. With developed markets like the US and especially Europe failing to deliver new entrants…is this distinction between emerging and developed becoming more murky? Food for thought.)

Less dry powder, fewer opportunity funds, and constrained follow-on capital mean GPs need new ways to monetize their pro rata or founder relationships.

Enter: secondary sales.

Whaty kinds of implications does this hold?

1. Traditional VC Metrics May Be Misaligned
   I was trained to believe that top-tier VC managers should (1) lead rounds and (2) take meaningful ownership to generate outsize returns. But this model assumes the exits will come — and often, they do not.

2. Illiquidity Creates Real Risk
   When those exits do not materialize, you are left holding a $500K–$1M stake with no clear path to liquidity. I recently spoke with a founder who has been operating for 7 years — his earliest investors are still stuck on the cap table with no return.

3. Smaller Initial Checks + Secondary Sales May Offer a Smarter Path
   A model of sub-$250K investments in pre-seed/seed stages, with a strategy to exit through secondaries at Series A or beyond, may offer more realistic, distributable returns — especially for emerging managers.

4. This Approach May Also Reintroduce Discipline
   Smaller check sizes could encourage founders to be more self-sufficient and capital-efficient, rather than assuming large checks are a given.

5. Too Much Early Capital = Misaligned Incentives
   Many founders today use their $1M–$4M raises to pay themselves and fund bloated marketing budgets. This capital use often precedes real product traction.

6. Reaching Product-Market Fit Is Cheaper Than Ever
   With free tools like email platforms, Instagram, and Canva, building an audience and testing demand costs little more than time. If yours truly can bootstrap a content platform on <$100/year, technical founders should be able to do even more with less.

7. Expect More From Founders
   Founders with real technical skills should be able to ship, test, and scale basic products without relying heavily on paid ads or bloated headcount. Capital should be a lever — not a crutch.

The landscape of private asset investing is changing dramatically.

I think there will be a pardigm shift in opportunities for investors allocating smaller checks. But only time will tell!

 📊Stat of the Week

Courtesy of the Economist:

I was pleased to see this stat in this week’s Economist, after I had already written this newsletter draft. Private equity and VC distributions as a % of NAC are at historical lows, which ties right back to the case for SPVs and the shifting venture capital landscape.

🎙 Content Recap

There really will be a new Money Memories episode this week featuring the founder of Sonar, a mental health startup focusing on children. Tune in on Wednesday wherever you listen to podcasts, and don’t forget to download and subscribe!

In Forbes, I talked about the challenges that Europe is facing in catching up to the US in terms of innovation.

📍 Where I’ll Be

If you are attending any of these upcoming events, let me know. I would love to find time to connect:

• June 10: I’m hosting my own networking event for founders and investors in Los Angeles. Sign up here to attend and / or share with a friend!

• June 11: I’m paticipating in a virtual panel on term sheets for founders. If you’ve ever wanted to know the nitty grity of raising money, don’t miss this session. Sign up here.

• June 25 - 27: I’ll be back in San Francisco for the Wharton Global Forum. If you’re in in the Bay Area, let’s meet up!

🔗 Other Interesting Reads & Listens

📌Roland Garros Night Slot Drama: I’m a huge tennis fan, and the perennial discussion abot what’s “fair” for women’s vs. men’s players is exhausting. Put women on night matches, Roland Garros.

As always, I would love to hear your feedback. Is there something you want to see more (or less) of? Just hit reply and send me your thoughts—or DM me on IG.

Till next week!
💛 Ilona