term sheet
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One of the most exciting moments in the life of every newly christened founder is the sweet relief of seeing a term sheet come in from an investor. After weeks, perhaps months (but hopefully not years!), of work fundraising and pitching, there is nothing like getting that email with a PDF attached to it laying out the terms and conditions of the VC relationship going forward.
Of course, that rejoicing dampens quickly as all the specific nuances of the deal suddenly come to the forefront. It’s one thing to get the valuation you want, or the amount of capital you are seeking, but what about the setup of the board of directors? What should you do about deal terms that may shape your startup for a decade or more?
The reality of term sheets, as our guest Lior Zorea discusses, is that the terms you agree to early on at a startup tend to be the terms that will carry through for the life of the company. That means getting that first term sheet right is critical for ensuring the financial and capital success of your business.
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Over the past two decades, the venture capital industry has exploded beyond anyone’s wildest imaginations.
What began as a sleepy industry in Boston and Menlo Park has now expanded to dozens of cities the world over. The National Venture Capital Association estimates that VCs deployed more than $130 billion in 2018 and 2019, and thousands of new investors have joined the ranks in recent years to find the next great startups.
All that activity, though, poses a dilemma for founders: Who actively writes checks? Who is a leader in a specific market or vertical? Who has the conviction to underwrite pathbreaking investments? Who, ultimately, do you want to have by your side for the next decade as your startup grows?
There are lists that rank VCs by their exit returns. There are lists that rank young VCs by their potential. There are lists of VCs who claim investment interest in various sectors. There are lists that try to ferret out deal volume, impact and other quantitative metrics. There are internal lists at accelerators that share collective wisdom between founders.
Who actively writes checks? Who is a leader in a specific market or vertical? Who has the conviction to underwrite pathbreaking investments? Who, ultimately, do you want to have by your side for the next decade as your startup grows?
All those lists and rankings have an important function to serve, but for all the compilations of investors out there, we couldn’t find a single one that publicly answered a simple yet vital question: Who are the VC investors who are leaders in specific verticals who should be a founder’s first stop during a fundraise?
Today’s venture industry is made up of thousands of investors with varying specialties, and far too many passive investors that are willing to participate in rounds but don’t actively participate in deals unless other investors have committed. Many don’t actively push to get deals done or don’t actively lead the charge to build a syndicate of investors.
With all that in mind, we’re excited to launch a new initiative that we hope will help answer those questions and help founders find that first check — The TechCrunch List.

Over the next few weeks, we’re going to be collecting data around which individual investors are actually willing to write the proverbial “first check” into a startup’s fundraising round and help catalyze deals for founders — whether it be seed, Series A or otherwise (i.e. out of your Series A investors, the first person who was willing to write the check and get the ball rolling with other investors). Once we’ve collected, cleaned and analyzed the data, we’ll publish lists of the most recommended “first check” investors across different verticals, investment stages and geographies, so founders can see which investors are potentially the best fit for their company.
Founders are used to being specialized; after all, they have to live and breathe their startups every single day. So it can be jarring to start talking to generalist investors who know little about a category and ask shallow questions only to render a judgment with irrelevant advice. One of the greatest impetuses for us to put together The TechCrunch List is that like founders, we also struggle to cut through the noise around the interests of individual VCs.
We’d argue that’s close to impossible. There is more spend on technology than ever before in history. Verticals are getting more competitive — market maps that used to have 10 to 50 companies have expanded to hundreds. The only way to compete today is to specialize, and that has never been more true for VCs.
In all, The TechCrunch List will publish the most recommended “first check” writers across 22 different categories, ranging from D2C & e-commerce brands to space, and everything in between. Through some data analysis around total investments in each space, we believe our 22 categories should cover the entirety or majority of the venture activity today.
To make this project a success and create a useful resource for founders, we need your help. We want to hear from company builders and we want to hear from them directly.
To make this project a success and create a useful resource for founders, we need your help. We want to hear from company builders and we want to hear from them directly. We will be collecting endorsements submitted by founders through the form linked here.
Through the form, founders will be asked to submit their name, their startup, the stage of company, the name of the one “first check” investor they want to endorse and a couple of minor logistical items. We are asking founders here for their on-the-record endorsement. We ask that you limit your recommendations to one (1) person per fundraise round.
While many investors may have helped you in your journey, we are specifically interested in the person who most helped you get a round underway and closed. The one who catalyzed your round. The one who guided you through the fundraise process. The one investor you would ultimately recommend to other founders who are trying to find their VC champion.
Our main goal is to help founders, dreamers and company builders find investors who will invest in them today, and with your help, we think we can. The TechCrunch List is not meant to identify every possible investor under the sun who might make an investment within a space, nor just the big household-name VCs whose reputations can sometimes seem more linked to their follower counts on Twitter as opposed to their bold term sheets.
Our hope is that this can be a go-to resource for founders looking to fundraise going forward, and with that in mind, we are very determined to improve the glaring representation gaps in the venture industry. It’s no secret that the world of VC still looks like a country-club membership roster, dominated by white men with strong opinions and loud voices. Looking at the data, it’s clear that there are groups that are particularly underrepresented, with only a small portion of the industry made up of Black, Latinx and female investors, for example.
We want to amplify these voices and we want to hear particularly from founders of color, female founders and other underrepresented groups. We also want to make sure our recommended investor lists are sufficiently representative and highlight underrepresented investors who might not have had equal opportunities in the past.
We want to help builders wade through the BS politics and fundraising annoyances that founders complain to us about on a daily basis, and help them identify qualified leads that are actually active, engaged and specialized and are the best fit to help founders raise money and grow now.
Thank you for your support. We’re excited to build The TechCrunch List with you — and for you.
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When we launched in 2016, we took the unusual approach of saying we’d buy common stock in startups. We believed then, and still do, that alignment with founders was more important than covering our downside in investments that didn’t work as planned. Said differently, we wanted to enhance our upside through alignment, rather than maximizing our downside through terms.
The world has changed a lot since that time. While we are actively making investments, and still buying common stock, we know that many entrepreneurs may be trying to raise money now — and it is very hard.
Fred Destin wrote a great piece about the ugly terms that can creep into term sheets during difficult times. If you have a choice between a good term sheet and a bad one, of course, you’ll take the good one. But what if you have no choice? And how can you compare term sheets in the first place?
To this end, we developed the term-sheet grader, a simple way to compare different term sheets or help characterize whether a term sheet is good or evil.
Let me first point out that none of this has anything to do with the valuation of the round (share price), the amount of capital, the likelihood of reaching a closing, the quality of the firm or the trust you have with the individual leading the investment, all absolutely critical pieces of the puzzle. Here, we are just looking at the terms and conditions, the legal structure of the investment.
We’ve listed nine key terms below — five that have to do with economics and four that relate to control and decision-making:
FWIW, the Pillar common stock standard deal earns a +8 (shown below).
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The increase in activity in the pre-IPO secondary market means that founders, early employees, and investors are receiving liquidity much sooner in a company’s lifecycle than ever before. For most startups and privately-held companies, liquidity is often an issue for stockholders, as no market exists for selling shares and/or transfer restrictions can prevent their sale. Secondary stock transactions, however, are a way to work around this problem.
Here’s a quick look at how they work and what to keep in mind, especially if you’re going through the process for the first time. (If you’re not familiar, secondaries are transactions in which an existing stockholder sells their stock for cash to third parties or back to the company itself before the company undergoes an exit; traditionally, an exit refers to an M&A or an IPO.)
Offering secondary transactions to founders is a tool VCs have been using to win deals. For example, if a VC promises that the founders will receive $1,000,000 in cash through a secondary sale from a $15,000,000 venture financing round, the founders will likely prefer that VC’s term sheet to a term sheet from a VC that does not offer that deal.
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Founders need to get smart quickly about the many nuanced aspects of building a company, from understanding weird language in a big term sheet to hiring a key software developer.
But the best practical advice is scattered across blog posts, podcasts and books, and it gets outdated quickly as industry norms evolve. Even experienced founders spend a lot of time searching and still end up with the wrong information.
Holloway has an ambitious solution: Today, it’s launching a library of book-length online guides about work, written and regularly updated by teams of industry experts.
The flagship title is called Raising Venture Capital, which features 340 thoughtfully organized pages in 15 sections and three appendices on all aspects of the funding process. Designed for easy reading and easy searching in spite of the information density and length (it has a 14-hour total read-time), the guide could become a go-to resource for the startup world.
Some sections will be most appealing to newer founders, like the part on whether to raise VC in the first place. Other portions are relevant to even the most experienced serial entrepreneurs — like how to think through potential drag-along and pay-to-play provisions, full-ratchet anti-dilution clauses and other tricky terms one might find. Did you know that investors can include more than 20 types of conditions in a term sheet? Do you know how to handle each one?
With $4.6 million in seed funding from a combination of top tech investors and The New York Times that it is also announcing now, Holloway intends to expand to cover the wide variety of work-related topics about startups and technology, and beyond. The next guide, currently in progress, will be on technical hiring and recruiting. A relatively shorter sample guide on equity compensation is already available for free.
The goal is to democratize access to how the best are doing business today (and take on traditional publishing).
“We didn’t just do this for Silicon Valley and New York,” and other startup-heavy cities, co-founder and chief executive Andy Sparks tells me, “we did this for people in cities like Columbus and Atlanta where startup communities are growing, but knowledge is harder to come by.”
The lawyers and other experts who author and edit the guides could otherwise cost more than $800 an hour, he explains, and won’t have time for many clients in the first place. (The company estimates there are $40,000 worth of legal fees in the VC guide.)
Sparks, previously the co-founder of analytics platform Mattermark, is also the lead author on “Raising Venture Capital” — along with another 20 or so contributors, like Brad Feld of the Foundry Group, and Darby Wong, co-founder of the popular legal document startup Clerky . The lead author of the technical recruiting guide is Ozzie Osman, former head of product engineering at Quora, and a main contributor to it is Aditya Agarwal, the former CTO of Dropbox.
The current pricing is $100 per guide forever (including future updates), with a discount available if you pre-order. Sparks says this may change to ensure the guides stay affordable, as well as cover the very real costs of producing this quality of content.

The big-picture bet is that the startup market is large enough to create strong demand for the initial guides, in the same way that many successful tech startups of this decade have started out serving companies like themselves. Some of the topics that Holloway is working on, like tech recruiting, naturally blend in with the rest of the business world and those wider audiences. Eventually, through expansion into broader work-related topics, Holloway’s online-first approach could compete against the existing book publishing industry at a bigger scale.
This is why the company is investing heavily in its software, in addition to its content. The interface was inspired by the experiences of co-founder Joshua Levy, a veteran technologist who found himself writing popular third-party guides on GitHub about how to use common services like AWS. Features in the software include search results that break out sections and sources, a detailed left-hand index view, a hyperlinked in-house glossary of hundreds of key terms, notes of warning and importance from experts and numerous links to third-party sources.
“We decided to invest in a digital reading experience that makes reading book-length content in a browser a great experience,” Sparks said, “which also means you will land on the right guide when you go hunting for answers on search engines like Google .”
Holloway co-founders Joshua Levy (left) and Andy Sparks (right)
You’ll even see a number of links to TechCrunch and Extra Crunch articles in the guides. Sparks tells me that the company plans to continue to link to a wide variety of sources in the future — so when guest columnists write something great and practical on Extra Crunch, we will help them to get this work featured in Holloway as well. The company is also accepting a variety of contributor types for its guides going forward, which you can find more details about here.
(On that note, we’ve published an excerpt from Holloway’s “Raising Venture Capital” guide, about pro rata terms and issues, on Extra Crunch. Subscribers can go check it out here, and find a special discount to Holloway inside.)
Sparks is careful to say that the current guides are not literally finished, despite all the effort put into them so far. And indeed, they will never be. Holloway is named after the “hollow ways” seen in the European countryside, where well-used roads have gradually sunk through hundreds of years of regular use. The company intends for its guides to be the paths that people who build companies tread year after year, where the knowledge that accumulates from the usage of many forms the clear direction that those in the future take.
The company’s investors include NEA, South Park Commons, The New York Times Co., Precursor Ventures and Comcast Ventures as well as Day One Ventures, Social Capital, Abstract Ventures, 415, Royal Bank of Canada, Lightspeed Ventures, & Full Tilt Capital. Angels include Leo Polovets, Lee Linden, Raj De Datta, Neil Parikh, Mikhail Larionov, Danielle & Kevin Morrill, Srinath Sridhar, Dennis Phelps and Kevin Lee.
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Three years ago, I met with a founder who had raised a massive seed round at a valuation that was at least five times the market rate. I asked what firm made the investment.
She said it was not a traditional venture firm, but rather a strategic investor that not only had no ties to her space but also had no prior investment experience. The strategic investor, she said, was looking to “get their hands dirty” and “get in on the ground floor.”
Over the next 2 years, I kept a close eye on the founder. Although she had enough capital to pivot her business focus multiple times, she seemed to be at odds, serving the needs of her strategic investor and her customer base.
Ultimately, when the business needed more capital to survive, the strategic investor didn’t agree with the founder’s focus, opted not to prop it up, and the business had to shut down.
Sadly, this is not an uncommon story as examples abound of strategic investors influencing startup direction and management decisions to the point of harm for the startup. Corporate strategics, not to be confused with dedicated funds focused on financial returns like a traditional venture investor like Google Ventures, often care less about return on investment, and more about a startup’s focus, and sector specificity. If corporate imperatives change, the strategic may cease to be the right partner or could push the startup in a challenging direction.
And yet, fortunately, as the disruptive power of technology is being unleashed on nearly every major industry, strategic investors are now getting smarter, both in terms of how they invest and how they partner with entrepreneurs.
From making strong acquisitive plays (i.e. GM’s purchase of Cruise Automation or Toyota’s early-stage investment in Uber) to building dedicated funds, to executing commercial agreements in tandem with capital investment, strategics are getting savvier, and by extension, becoming better partners. In some instances, they may be the best partner.
Negotiating a term sheet with a strategic investor necessitates a different set of considerations. Namely: the preference for a strategic to facilitate commercial milestones for the startup, a cautious approach to avoid the “over-valuation” trap, an acute focus on information rights, and the limitation of non-compete provisions.
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