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Benchmark is thrilled to announce Miles Grimshaw has joined the firm as our newest General Partner.

At age 29, Miles has emerged as one of the world’s great venture capitalists, embodying the early-stage focus and company building purpose that defines Benchmark.

Miles’s fiercely independent thinking has allowed him to identify the early potential of some of the breakout companies of this era, including Segment (acquired by Twilio for $3.2B), Benchling, and Airtable, investing in each of these companies before they had 30 employees. Miles cold-emailed Benchling CEO Saji Wickramasekara when the company had zero revenue and a few hundred users. As Saji said, “When everyone else was hung up on market size, Miles saw the expansive possibilities and energized us to go after them.”

Miles has learned from the team at Thrive Capital, one of the great venture firms of this era, how to partner in radical support of CEOs and the teams they lead. Through Benchmark and Thrive’s joint investments, we’ve been able to witness firsthand as Miles built the deep relationships we view as essential to helping entrepreneurs achieve their biggest aspirations.

Intensely competitive, Miles channels this energy into 100-mile races on weekends. Born in the United Kingdom, raised by an entrepreneurial Korean stepfather, and having attended schools in England, India, China, and the United States, Miles will bring a global breadth of perspective to the investments he’ll make. Lastly and perhaps most importantly, we’ve been awed by Miles’s maturity and rate of growth as we’ve served as board members together on Benchling, Airtable, and Supergreat. Miles exhibits the judgment of someone with decades more experience.

As other venture capital firms have scaled their partnerships and infrastructure, adding junior or role-defined staff to help their partners scale to more boards, Benchmark has stayed true to our beginnings. A small, equal partnership of now five General Partners, we remain focused on serving the extraordinary founders with whom we work. To do this and continue to perform at the level we aspire to, each person we add to our partnership must raise the bar and make us all better. We have the highest conviction Miles will not only excel at the complex craft of early-stage venture investing but also push all of us in our thinking. …

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A successful framework distills the complex, and in that synthesis, gets to a timeless insight. That’s always my aspiration, to varying degrees of success.

Here’s a running list of frameworks I’ve written on a range of topics.

Recipes to build enduring, mass-market businesses:

  • 10x and Cheaper — What do Airbnb, Amazon, Netflix, Uber, and WhatsApp all have in common? They created a 10x better product and made it cheaper by recasting cost structures of incumbents.
  • Saving people money — Fintech edition for 10x and Cheaper. It’s not just about being able to buy something better for less. …

The #1 question I got after publishing my Hierarchy of Marketplaces series is how to know if you are on the right track in Level 1 as you wait for your cohorts to mature, and whether you can use Net Promoter Score (“NPS”) to measure happiness. Honestly, I’m skeptical of NPS’s utility. Instead I recommend measuring your funnel to what I’ll call “Happy GMV”. Below I describe what that is, and then elaborate on why I’m over NPS.

Happy GMV

As you wait for your cohorts to mature, start by asking yourself “what is my best guess at the buyer and seller experience that will lead to retention?” and then measure the percentage of your potential buyers and sellers that get that experience. …

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If you’ve read Level 1 and Level 2 of my Hierarchy of Marketplaces series, and are biting at the bit to go big, Level 3 is for you.

Level 1 and Level 2 were all about single-threaded focus. If reaching Minimum Viable Happiness is hard enough, reaching the second happiness threshold that gets the market to “tip” in your direction is even harder. You need incredible focus to achieve both.

If you’re ready for Level 3, your cohorts are performing stronger and stronger, and you are seeing more and more organic growth. Congratulations, the market is tipping towards you. …

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In the Introduction and Level 1 of the Hierarchy of Marketplaces, I laid out the core insight that drives the hierarchy: that the tireless pursuit of happiness (not GMV) is ultimately what distinguishes the marketplaces that endure.

This is not to say that you shouldn’t pursue growth when building a marketplace. Indeed, to increase happiness marketplaces need to grow. But the growth must be in service of increasing happiness. This is what Level 2 is all about.

If your goal in Level 1 was to kickstart transactions and reach “Minimum Viable Happiness”, Level 2 is about reaching a new happiness threshold where you are just so much better than any substitute that the market “tips” in your direction. …

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A few years ago, I published a framework I called The Hierarchy of Engagement (Version 1, and updated “Expanded” Version) which synthesized my thinking on how to build enduring consumer products. The Hierarchy of Marketplaces synthesizes my thinking on how to build enduring marketplaces.

Marketplaces that are able to scale the hierarchy build dominant “winner take most” value. What is required to get there is a focus not on GMV, but on creating happiness.

The marketplace that wins is the marketplace that figures out how to make their buyers and sellers meaningfully happier than any substitute. …

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Social distancing has dramatically changed how we spend our time. With all in person gatherings canceled, people suddenly have a lot more free time on their hands. New and incumbent consumer internet companies are racing to claim that time.

As an investor in and lover of consumer products, I’m incredibly excited by the opportunities this window represents. But I’ve also asked myself what distinguishes a consumer startup that will not only thrive during a time of social distancing, but after? This is how I think about it, and some advice to consumer founders out there.

Introducing a Rocks, Sand, and Water Framework for Attention

We always talk about consumers’ attention as being finite, but how is it divided? …

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One of the questions I get a lot is, “Is there any white space left to build a consumer marketplace?”

I get it. Name a category or vertical and you can probably think of a company that is either a) already there, or b) seemingly in a better position than you are to capitalize. Which is why, if you define “white space” as a big, wide-open, untouched area of opportunity, it will seem as though every “space” is already taken.

What so many people forget, however, is that many of our current incumbents actually disrupted the prior incumbents. Airbnb launched years after HomeAway (2005) and VRBO (1995!). GOAT was founded more than a decade after eBay. …

In 2011, Grubhub* was one of the most innovative companies in the world.

The company had just successfully raised $20 million to expand its operations all across the United States, and a year later they would raise another $50 million. By 2014, the small food delivery startup would merge with SeamlessWeb and hit the NYSE with a valuation of $2 billion and go on to seemingly secure its dominance of a category of dining that hadn’t existed before: technology-driven food delivery.

Five short years after Grubhub’s iconic rise to becoming a public company, Vox reported at the start of 2020 rumors the company may soon be up for sale. …

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Gartner Hype Cycle

Many years ago, Gartner created the Hype Cycle to provide a “graphic representation of the maturity and adoption of technologies and applications.” Although many people have since picked apart the Hype Cycle and pointed out all the examples of technologies that did not follow this cycle, there is an undeniable wisdom to it, one that I believe is also relevant to product.

When I was at Pinterest and now, in many conversations with founders and product leaders, I notice that many features go through their own hype cycle:

First, there would be the “Trigger”. It might have been a brainstorming idea, a hackathon project, an insight from user research, or a strategic decision from someone. Whatever the catalyst, the idea would start to gain internal momentum and visibility. Documents would be written, designs perfected, prototypes built. And expectations would quickly rise. I’ve written about my own experience here — the rush of feeling like something you were working on was going to be the most. important. feature. you’ve. ever. shipped. TRANSFORMATIVE!

And then… you ship it. For the rare feature, the adoption is immediate and impactful. I always think of Instagram Stories as a perfect example of this. But most times, the enthusiasm for a feature plunges into the Trough of Disillusionment. Users aren’t discovering the feature, or they discover it but don’t try it, or they try it but don’t keep using it. And far too often, a product org and company move on to the next idea ascending its own peak of inflated expectations.

Of course, sometimes this is the right call. You had a hypothesis for a product, and guess what, you were wrong. But most times, this ends up meaning that the feature never has a chance to climb the Slope of Enlightenment and get to the Plateau of Productivity.

Just like not all consumer startups have the right-from-the-start launch of Facebook, not all features are Instagram Stories. It takes iteration — playing with how users discover the product, building and tuning the growth loops, adding additional depth to the feature, tweaking the copy, etc., to really give a feature a chance.

So before you move on, it’s worth asking yourself: are you giving up in the trough of disillusionment? And what would it take to climb the slope of enlightenment?

And don’t forget: It’s also worth taking a look at the features you already have that have been coasting in the plateau of productivity and ask yourself whether any might be worth replacing or even removing? …


Sarah Tavel

native new yorker, SF-resident. general partner @benchmark. formerly product @Pinterest. originally blogging at

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