Holloway launches in-depth startup guides, aims to rewrite publishing with $4.6M from NYT, tech VCs


holloway showcase product

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But the best practical advice is scattered across blog posts, podcasts and books, and it gets outdated quickly as industry norms evolve.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.holloway showcase guidesThe 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.

Holloway sample 3

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.


More TechCrunch

It’s a wrap: European Union lawmakers have given the final approval to set up the bloc’s flagship, risk-based regulations for artificial intelligence.

EU Council gives final nod to set up risk-based regulations for AI

London-based fintech Vitesse has closed a $93 million Series C round of funding led by investment giant KKR.

Vitesse, a payments and treasury management platform for insurers, raises $93M to fuel US expansion

Zen Educate, an online marketplace that connects schools with teachers, has raised $37 million in a Series B round of funding. The raise comes amid a growing teacher shortage crisis…

Zen Educate raises $37M and acquires Aquinas Education as it tries to address the teacher shortage

“When I heard the released demo, I was shocked, angered and in disbelief that Mr. Altman would pursue a voice that sounded so eerily similar to mine.”

Scarlett Johansson says that OpenAI approached her to use her voice

A new self-driving truck — manufactured by Volvo and loaded with autonomous vehicle tech developed by Aurora Innovation — could be on public highways as early as this summer.  The…

Aurora and Volvo unveil self-driving truck designed for a driverless future

The European venture capital firm raised its fourth fund as fund as climate tech “comes of age.”

ETF Partners raises €284M for climate startups that will be effective quickly — not 20 years down the road

Copilot, Microsoft’s brand of generative AI, will soon be far more deeply integrated into the Windows 11 experience.

Microsoft wants to make Windows an AI operating system, launches Copilot+ PCs

Hello and welcome back to TechCrunch Space. For those who haven’t heard, the first crewed launch of Boeing’s Starliner capsule has been pushed back yet again to no earlier than…

TechCrunch Space: Star(side)liner

When I attended Automate in Chicago a few weeks back, multiple people thanked me for TechCrunch’s semi-regular robotics job report. It’s always edifying to get that feedback in person. While…

These 81 robotics companies are hiring

The top vehicle safety regulator in the U.S. has launched a formal probe into an April crash involving the all-electric VinFast VF8 SUV that claimed the lives of a family…

VinFast crash that killed family of four now under federal investigation

When putting a video portal in a public park in the middle of New York City, some inappropriate behavior will likely occur. The Portal, the vision of Lithuanian artist and…

NYC-Dublin real-time video portal reopens with some fixes to prevent inappropriate behavior

Longtime New York-based seed investor, Contour Venture Partners, is making progress on its latest flagship fund after lowering its target. The firm closed on $42 million, raised from 64 backers,…

Contour Venture Partners, an early investor in Datadog and Movable Ink, lowers the target for its fifth fund

Meta’s Oversight Board has now extended its scope to include the company’s newest platform, Instagram Threads, and has begun hearing cases from Threads.

Meta’s Oversight Board takes its first Threads case

The company says it’s refocusing and prioritizing fewer initiatives that will have the biggest impact on customers and add value to the business.

SeekOut, a recruiting startup last valued at $1.2 billion, lays off 30% of its workforce

The U.K.’s self-proclaimed “world-leading” regulations for self-driving cars are now official, after the Automated Vehicles (AV) Act received royal assent — the final rubber stamp any legislation must go through…

UK’s autonomous vehicle legislation becomes law, paving the way for first driverless cars by 2026

ChatGPT, OpenAI’s text-generating AI chatbot, has taken the world by storm. What started as a tool to hyper-charge productivity through writing essays and code with short text prompts has evolved…

ChatGPT: Everything you need to know about the AI-powered chatbot

SoLo Funds CEO Travis Holoway: “Regulators seem driven by press releases when they should be motivated by true consumer protection and empowering equitable solutions.”

Fintech lender SoLo Funds is being sued again by the government over its lending practices

Hard tech startups generate a lot of buzz, but there’s a growing cohort of companies building digital tools squarely focused on making hard tech development faster, more efficient and —…

Rollup wants to be the hardware engineer’s workhorse

TechCrunch Disrupt 2024 is not just about groundbreaking innovations, insightful panels, and visionary speakers — it’s also about listening to YOU, the audience, and what you feel is top of…

Disrupt Audience Choice vote closes Friday

Google says the new SDK would help Google expand on its core mission of connecting the right audience to the right content at the right time.

Google is launching a new Android feature to drive users back into their installed apps

Jolla has taken the official wraps off the first version of its personal server-based AI assistant in the making. The reborn startup is building a privacy-focused AI device — aka…

Jolla debuts privacy-focused AI hardware

The ChatGPT mobile app’s net revenue first jumped 22% on the day of the GPT-4o launch and continued to grow in the following days.

ChatGPT’s mobile app revenue saw its biggest spike yet following GPT-4o launch

Dating app maker Bumble has acquired Geneva, an online platform built around forming real-world groups and clubs. The company said that the deal is designed to help it expand its…

Bumble buys community building app Geneva to expand further into friendships

CyberArk — one of the army of larger security companies founded out of Israel — is acquiring Venafi, a specialist in machine identity, for $1.54 billion. 

CyberArk snaps up Venafi for $1.54B to ramp up in machine-to-machine security

Founder-market fit is one of the most crucial factors in a startup’s success, and operators (someone involved in the day-to-day operations of a startup) turned founders have an almost unfair advantage…

OpenseedVC, which backs operators in Africa and Europe starting their companies, reaches first close of $10M fund

A Singapore High Court has effectively approved Pine Labs’ request to shift its operations to India.

Pine Labs gets Singapore court approval to shift base to India

The AI Safety Institute, a U.K. body that aims to assess and address risks in AI platforms, has said it will open a second location in San Francisco. 

UK opens office in San Francisco to tackle AI risk

Companies are always looking for an edge, and searching for ways to encourage their employees to innovate. One way to do that is by running an internal hackathon around a…

Why companies are turning to internal hackathons

Featured Article

I’m rooting for Melinda French Gates to fix tech’s broken ‘brilliant jerk’ culture

Women in tech still face a shocking level of mistreatment at work. Melinda French Gates is one of the few working to change that.

2 days ago
I’m rooting for Melinda French Gates to fix tech’s  broken ‘brilliant jerk’ culture

Blue Origin has successfully completed its NS-25 mission, resuming crewed flights for the first time in nearly two years. The mission brought six tourist crew members to the edge of…

Blue Origin successfully launches its first crewed mission since 2022