Combatting mental health stigma through digital technology, growing awareness and entrepreneurship-by-necessity mindset

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As an angel and a VC, I’m driven by curiosity and passion for advancing innovative ideas that tackle pressing issues in essential sectors such as healthcare, focusing on often-overlooked emerging markets. I’m always on the lookout for new markets with untapped (or under-tapped) potential, broadening my scope beyond the usual industry and regional suspects to spot unique opportunities for growth. …

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Designing a sophisticated, focused fundraising strategy is a stepping stone towards a startup’s success

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One of the luxuries I have as a cross-border generalist VC and angel investor is the ability to see what works — and doesn’t work — for startups across a very broad range of industries, from wine (Vinebox and USUAL Wines) and wellness (ClassPass) to cybersecurity (Tortuga Logic), future-of-work (Gable), and healthcare (Nyquist Data).

Most great entrepreneurs I see are singularly focused on addressing customer pain points through delivering a new product or service to the market that is 10x superior to whatever competitors have to…

Ways to think about portfolio construction and reserve allocation when you launch your first pre-seed / seed fund

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‘All I can tell them is pick a good one and sock it. I get back to the dugout and they ask me what it was I hit and I tell them I don’t know except it looked good.’

- Babe Ruth

Contrary to the general wisdom of venture capital, successful pre-seed and seed investing from a sub-$50m fund is a lot about initial portfolio construction. Of course, in ideal world, you want to get as much ownership percentage as early as…

Why betting on a founder’s persona is a better strategy to deliver venture returns

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Watching the continuing IPO galore and Series A valuations uptick got me thinking about two central approaches I see to early-stage venture capital investing, and where my own investment philosophy fits in: momentum-based vs value-based investing.

While the former represents a dominant and attractive strategy on a surface, its effectiveness can prove illusory, with overblown successive valuation generating unrealistic growth expectations and disappointing returns. …

An essay on trust, commitment and straightforward relationship with failure

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During deal negotiation process, it can be easy for venture capitalists to hyper-focus on codifying contractual covenants between ourselves and entrepreneurs, putting substantive relationship-building on the back burner. While tempting, this approach is a grave mistake: to succeed as a portfolio manager long-term, it’s critical to strike the right balance between control and trust, investing in relationships as much as in companies themselves.

Indeed, no information rights can substitute great relationships built on trust and transparency. While less immediately tangible than formal control mechanisms, good cooperative VC-founder relationships deeply affect…

And thoughts on radical change, geniune gratitude and freedom to iterate and experiment

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After spending the last couple of weeks talking to entrepreneurs who are raising money in the pre-product/pre-revenue stage and seeing the common challenges they are facing, I want to re-visit this article about early stage fundraising and expand on it.

The ‘zero to one’ stage of tech companies’ lifecycle is the most lucrative from a venture capital economics perspective (higher equity ownership at a lower valuation, assuming a 1.5x-2.5x valuation step up in each of the subsequent investment rounds), but also the hardest at which to raise…

The emergence of new early-stage venture capital firms is critical for the inclusive and diverse future of tech innovations

It’s not a secret that angel and seed investments were jeopardized the most when the whole world went remote as a result of COVID-19.

As an emerging independent fund operator with 15 companies in my early-stage portfolio that have successfully raised over $650 million — as well as a longtime mentor at industry-leading accelerator Techstars, which has accelerated over 2,500 startups and raised close to $12 billion — I’m well-acquainted with the unique challenges and opportunities that come with this stage of investment.

In my experience, the earlier the stage of a company’s development, the more we rely on meeting…

Recession is an accelerant to innovation on the markets where founders have to bootstrap their way to profitability and focus on solving major existing market inefficiencies.


With the most recent $400M Series G raise Nubank got to a whopping $25B valuation, up from $10B in 2019. Beyond becoming the fourth-most valuable financial company in LatAm, Nubank is the largest challenger bank in the world: its user base has nearly tripled from 12M in 2019 to 34M today. That news made me re-visit the post I published here just before graduating from Stanford GSB earlier this summer.

As Latin America’s role…

Olga Maslikhova

Stanford GSB alum, early stage VC in consumer and SaaS, angel investor in ClassPass and Vinebox

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