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The Era of Easy $ Is Over

September 27, 2022
Written By
September 27, 2022
Written By
Tom Chavez

The era of easy money - or at least, easy returns for VCs - is over. Tom Chavez is calling for VCs to show up in-person at August board meetings, get off the sidelines, and start adding real value and hands-on support for founders.

Earlier this month, we had a board of directors (BOD) meeting for one of our super{set} companies. I was a little astonished to see one of our directors – the only VC in the room, in person.

His presence was conspicuous. Anyone who has been around the block knows precisely why: VCs take a good amount of the summer and all of August off. Several in attendance joked that it was lunacy to call a BOD meeting in August at all.

The lone VC present knew this, too. In fact, that’s exactly why he showed up. He told me that during his 30+ years as a successful VC, he'd made a point of always working during August, November, and December – precisely because he knew all of his VC peers would be on vacation then. He wanted to be known as the hard-working contrarian, and he was rightfully proud of it.

I had another conversation last month with a VC friend who is earlier in her career and hustling for deals. Recently, she’s been wondering if she’s too late to the party. Did she miss the relatively easy gains in software investing over the prior 25 years? The secular trend for software investing has been so abundant and huge that she wonders if any investor of just average intelligence with access to a reasonable deal flow could've made outsized returns.

Both encounters led me to reflect on my dealings with VCs over the last 25 years and what prototype of VC I’d like to work with for the next 25. It's a profession with a wealth-to-work ratio that outstrips any other career on the planet. That is why you never see VCs responding to emails or joining BOD meetings in August (or November or December, for that matter). But I’m starting to see many more VCs lately who are intuiting that the good times might be coming to an end.

Easy returns have been competed away. The era of easy investing is over.

Markets are efficient. There’s too much money and too many VCs competing for quality deals that are growing somewhat but not nearly at the same rate as the volume of capital sloshing around. Softbank's recent $23B loss points to the same general malaise of too much money and too many professionals chasing a market creaking under the weight of the caffeinated expectations hanging over it.

Just as management consulting enjoyed its heyday in the 80s and investment banking enjoyed its run in the 90s and early aughts, it's possible we’re approaching a similar turning point for VC.

There are a few who've earned big perches at established funds who will continue harvesting outsized monetary gains for a while longer. But most recognize they need to work harder, and they must usher in and deliberately battle-harden the next generation.

So what does the future look like?

VCs need to add real value – beyond $$$.  

Increasingly, VCs recognize they need to specialize. There was a time in the late 90s and early 00's when hedge funds could earn outsized returns by making fairly simple long-short bets and exploiting arbitrage opportunities. But again, markets are efficient, which is why all those gaps and price discrepancies have mostly been traded away. The easy money has already been made.

The same applies to VC. When I got into the game in 1999, VCs would read vapid Morgan Stanley reports and score points at their Monday meetings by quoting the bullets at the beginning of the report. They gave entrepreneurs inane advice like, "You need to focus," "You should fire your sales guy," and 'You need more revenue." You still get stupid comments and questions from some VCs when pitching a new project, but generally, they're all smarter simply because they have to be.

The days of easy, outsized VC returns are over. The VCs we're lucky to work with are showing up with meaningful insights about the markets we're chasing and the products we're building. They're more like investigative reporters than traditional financiers and asset allocators. That's a good thing for entrepreneurs in general, as it reflects the requirements and dynamics of the broader market.

VCs need to develop a more precise framework for making investment decisions.

The Accel approach pioneered by Arthur Patterson called for a 'prepared mind,' following Lavoisier's dictum that 'chance favors the prepared mind.' The idea was that by preparing and going deep in a particular sector (networking, vertical SaaS, etc.), a VC could discern the winning elements of a venture opportunity by pattern-matching from past data points and thinking deeply about the competitive advantage and market movements markets in a particular space. Other frameworks for specialization include Mike Maples at Floodgate’s two-pronged consideration of what he calls 'Inflections' and 'Insights'; Clint Korver at Ulu’s application of decision analysis to uncertain venture opportunities; Peter Wagner at Wing’s approach to the Data-Driven Enterprise; or super{set}'s data-driven thesis, which we use to structure product-centric, data management companies in markets ripe for cloud+data+AI disruption.

VCs need to offer more hands-on support for entrepreneurs.

Another way to differentiate is to become more useful to entrepreneurs. The VC industry refers to this as ‘platform’ capabilities. SignalFire touts its recruiting capabilities in helping newly formed companies staff their teams; A16Z brings outsourcing help to a company's marketing, technology, product, recruiting, and HR operations.

In general, I'm a little skeptical of these methods, first because it's just hard for a VC, however well-meaning, to engage with matters as critical as these without having their hands on the steering wheel. The related complexity is that, if they are successful, they might inadvertently disempower the CEO, who ultimately needs to have control and accountability for everything. But it's also possible that I haven't experienced those models firsthand, so perhaps they're more valuable than I know. At the very least, entrepreneurs should have high standards for them.

We started super{set} to provide the most direct hands-on support possible in early stage formation. Rather than chase outside ideas, we ideate in-house and then recruit and empower world-class product leaders as we build out the initial team and product. Just like they taught you when you had your learner’s permit: our hands never leave the steering wheel - 10:00 and 2:00 the entire time. Of course, not every VC can do what super{set} does, nor should we expect them to. However, the ecosystem needs the capital and the selection acumen VCs provide to enable scale and growth.

If a VC can’t be more useful – or doesn’t want to take that path – they should be giving out easier money with fewer terms.

Let’s call this the Tiger model. No board seats, just money – with minimal terms. It works great during the go-go times, even if it declines along with the business cycle. No board seats, just money with minimal terms. I think we’ll see the spigot open again, but even as it does, it's not clear to me that this is a durable approach for a true venture investor (as opposed to a big money allocator) to survive and differentiate.

So what’s the bottom line for entrepreneurs and the VCs that serve them?

Entrepreneurs deserve more – and they have every right to expect it.

Entrepreneurs have more agency than they think they do. So I’m telling every founder in my network and the co-founders and leadership teams within super{set} that it’s time to start asking and expecting a whole hell of a lot more from our VCs. In an industry that thrives by demanding founders work round the clock to earn their keep, it seems those skimming so much off the top should bring much more to the table than money and weak platitudes. Where are the VCs who will stick with you through thick and thin and stand shoulder-to-shoulder with you when the going gets rough? Where are the VCs who come to BOD meetings in person in August? I’m pretty sure I’m not the only entrepreneur taking stock of the rare VC who shows up for my company, however inconvenient or arduous the circumstances.

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Written By
Written By
Tom Chavez
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The Four Types of Startup Opportunities

In our last post, we discussed how data is the new general-purpose technology and that is why at super{set} we form data-driven companies from scratch. But new technologies are a promise, not a sudden phase change.

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VCs Write Investment Memos, We Write Solution Memos

When a VC decides to invest in a company, they write up a document called the “Investment Memo” to convince their partners that the decision is sound. This document is a thorough analysis of the startup...

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Q&A with Accel Founder Arthur Patterson

Arthur Patterson, founder of venture capital firm Accel, sits down for a fireside chat with super{set} founding partner Tom Chavez as part of our biweekly super{set} Community Call. Arthur and Tom cover venture investing, company-building, and even some personal stories from their history together.

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Four Tips for a Distributed Workforce

This month we pass the mic to Sagar Gaur, Software Engineer at super{set} MLOps company MarkovML, who shares with us his tips for working within a global startup with teams in San Francisco and Bengaluru, India

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High-Velocity Personal Growth

What's the price you put on personal growth? In his most recent note to founders, super{set} Founding General Partner Vivek Vaidya outlines 7 points of advice for startup interviews and negotiations. Vivek explains his compensation philosophy and the balance between cash and the investment in personal and career growth a startup can bring. Here’s the mindset you need to reach your zenith at a startup.

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Navigating Juneteenth

Considered by some to be “America’s Second Independence Day,” Juneteenth has only recently entered the national zeitgeist. Celebrated on the third Saturday in June, it became a federal holiday just last year under President Joe Biden. Many companies are left wondering how to acknowledge the holiday. We sat down with Eskalera’s co-founder Dr. Tolonda Tolbert to get her take.

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Why I Left Google To Co-found with super{set}

Gal Vered of Checksum explains his rationale for leaving Google to co-found a super{set} company.

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From Chords, to Code, to Chords Again: The Story Behind Boombox.io

super{set} founding general partner Tom Chavez wasn’t always set on a life of engineering and entrepreneurship – music was his first love. For a time, he was determined to make a career out of it. With boombox.io, Tom has combined the best of both worlds into a product that inspires and delights both the engineer and the musician.

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Why I'm Joining super{set} as Chief Commercial Officer

Announcing Jon Suarez-Davis (jsd) as super{set}’s Chief Commercial Officer: jsd tells us in his own words why he's joining super{set}

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An Intro to Product-Led Growth from MarkovML

Want to grow your product organically? This blog post breaks down understanding costs, setting up starter plans, and pricing premium features using MarkovML as an example. Learn how to engage new users and encourage upgrades, enhancing user experience and fueling growth through actionable insights.

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Jamming with Habu’s Matt Kilmartin on Partnership Strategy

Discover how Habu, a trailblazer in data clean room technology, utilizes strategic partnerships with giants like Microsoft Azure, Google Cloud, and AWS to expand its market reach and foster the potential of an emerging category. Learn from CEO Matt Kilmartin's insights on how collaboration is the secret sauce that brings innovation to life.

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7 Ways to Turn an Internship Into a Job at a Startup

Chris Fellowes, super{set} interned turned full time employee at super{set} portfolio company Kapstan, gives his 7 recommendations for how to turn an internship into a job at a startup.

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Horizontal Scaling at super{summit}

Vivek gives us the rundown on what the hive is buzzing about after super{summit} 2023: how to 'horizontally scale' yourself.

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Diamonds in the Rough

Obsessive intensity. Pack animal nature. Homegrown hero vibes. Unyielding grit. A chip on the shoulder. That's who we look for to join exceptional teams.

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Silicon Valley’s Greatest Untapped Resource: Moms

This post was written by MarkovML Co-Founder, Lindsey Meyl, as part of our #PassTheMic series.

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The RevOps Bowtie Data Problem

Go-to-market has entered a new operating environment. Enter: RevOps. We dig into the next solution space for super{set}, analyzing the paradigm shift in GTM and the data challenges a new class of company must solve.

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We don’t critique, we found and build.

The super{set} studio model for early-stage venture It is still early days for the startup studio model. We know this because at super{set} we still get questions from experienced operators and investors. One investor that we’ve known for years recently asked us: “you have a fund — aren’t you just a venture capital firm with a different label?”

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Data Eats the World

The wheel. Electricity. The automobile. These are technologies that had a disproportionate impact on the merits of their first practical use-case; but beyond that, because they enabled so much in terms of subsequent innovation, economic historians call them “general-purpose technologies” or GPTs...

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The Balancing Act For Women in Tech

This post was written by Ketch Sales Director, Sheridan Rice, as part of our #PassTheMic series.

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Tom Chavez in The Information: "TikTok Is Not the Enemy"

Tom writes a nuanced take on the TikTok controversy and outlines ethical data principles that will restore people’s sense of trust and offer them true control over how and when they grant permission for use of their data.

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The super{set} Entrepreneurial Guild

Has someone looking to make a key hire ever told you that they are after “coachability”? Take a look at the Google ngram for “coachability” — off like a rocket ship since the Dot Com bubble, and it’s not even a real word! Coaching is everywhere in Silicon Valley...

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How Boombox Nurtures Customer Collaboration for Success

In a conversation with boombox's co-founder India Lossman, the discussion pivots to the art of fostering customer collaboration in music creation. Lossman unveils how artist-driven feedback shapes boombox's innovative platform, with a glimpse into AI's empowering potential. Understand the synergy between technology and user insights as they redefine the independent music landscape.

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Navigating the Startup Journey from Launch to Finish Line

Are you a launcher, or a finisher? The balance of conviction, a guiding vision, and the right team to execute it all make the difference between entrepreneurial success and failure. Tom Chavez delves into his journey as a first-time CEO and the invaluable guidance he received from a key mentor.

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Founder and Father: A Balancing Act

Making It Work With Young Kids & Young Companies

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Good Ideas, Good Luck

Coming up with new company ideas is easy: we take the day off, go to the park, and let the thoughts arrive like butterflies. Maybe we grab a coconut from that guy for a little buzz. While this describes a pleasant day in San Francisco, it couldn’t be further from the truth of what we do at super{set}. If only we could pull great ideas out of thin air. Unfortunately, it just doesn’t work that way.

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How To Avoid Observability MELTdown

o11y - What is it? Why is it important? What are the tools you need? More importantly - how can you adopt an observability mindset? Habu Software Architect Siddharth Sharma reports from his session at super{summit} 2022.

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Too Dumb to Quit

The decision to start a company – or to join an early stage one – is an act of the gut. On good days, I see it as a quasi-spiritual commitment. On bad days, I see it as sheer irrationality. Whichever it is, you’ll be happier if you acknowledge and calmly accept the lunacy of it all...

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Not Just On Veterans Day

This post was written by Ketch Developer Advocate, Ryan Overton, as part of our #PassTheMic series.

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Lessons of Grit from my Immigrant Parents

This post was written by Ketch Solutions Engineer, Sahiti Surapaneni, as part of our #PassTheMic series.

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Building Tech on a Moving Regulatory Target

In an interview with Ketch co-founder Max Anderson, the focus is on data privacy laws and AI's role. Anderson discusses the global privacy landscape, highlighting Ketch's approach to helping businesses navigate regulations. The conversation also emphasizes data dignity and Ketch's unique role in the AI revolution.

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How Engineers Should Talk to Customers with Empathy

Do you get an uneasy feeling anytime you get added to a customer call? Do you ever struggle to respond to a frustrated customer? Peter Wang, Product lead at Ketch, discusses how customer feedback can help drive product development, and how engineers can use customer insights to create better products. Learn best practices for collecting and interpreting customer feedback.

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The Era of Easy $ Is Over

The era of easy money - or at least, easy returns for VCs - is over. Tom Chavez is calling for VCs to show up in-person at August board meetings, get off the sidelines, and start adding real value and hands-on support for founders.

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Thick Skin, Tech and Black History Month

This post was written by Ketch Data Privacy & Compliance Specialist, Jocelyn Brunson, as part of our #PassTheMic series.

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When Inference Meets Engineering

Othmane Rifki, Principal Applied Scientist at super{set} company Spectrum Labs, reports from the session he led at super{summit} 2022: "When Inference Meets Engineering." Using super{set} companies as examples, Othmane reveals the 3 ways that data science can benefit from engineering workflows to deliver business value.

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