February 2, 2022

What are the best educational resources for startup founders?

Amy Cuevas Schroeder
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What are the best educational resources for startup founders?What are the best educational resources for startup founders?
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Editor's note: 

When we asked the Unusual Ventures team – a mix of investors, technical founders, and practitioners – to share their recommended educational resources for startup founders, they responded with clarifying follow-up questions like “Can we recommend books?” and “How about events?” 

Great questions to be sure.

But instead of providing an exhaustive list of all things entrepreneurial, we’re highlighting a handful of mainly free educational resources and tools, such as websites and newsletters, that you might not have heard about yet. 


As for books, incubators, and events — those deserve their own lists! So stay tuned.

Lenny Rachitsky’s newsletter for product and tech insights

For the inside scoop

Lenny Rachitsky is an entrepreneur–angel investor–product manager whose weekly Substack newsletter is chock-full of actionable advice about product development, growth strategy, and early-stage investing. If you upgrade to a paid subscription, you’ll gain access to more content and a private community of thousands of product managers, founders, and growth leaders.

Rachitsky is currently living the self-employed Passion Economy life and teaches a product management fundamentals course. But his wisdom comes from entrepreneurial roots. After Airbnb acquired the company he co-founded – Localmind — in 2012, Rachitsky joined Airbnb as a product leader until 2019.

Suggested by Sandhya Hegde, General Partner, Unusual Ventures

TechCrunch and Business Insider pitching advice

For effectively pitching reporters, according to the reporters themselves

Getting good, relevant earned awareness through media has never been more important — and it’s never been harder to achieve. 

There are three pressures creating this perfect storm: 

1. More publications are shedding staff or closing their doors entirely.

2. The landscape for innovation is getting larger and more complex, with multiple well-funded new entrants competing to dislodge incumbents.

3. Bottoms-up and Modern GTM motions are making audience-level awareness more and more strategic for startup marketing, as leading companies are increasingly building adoption experiences that encourage users to self-serve from awareness all the way through to usage and expansion.

To address these three challenges, founders must reach their target audience through the channels that matter to them. The media gatekeepers (reporters) are increasingly inundated with more PR pitches than they can ever handle, so smart founders have to tailor their PR pitches to rise above the noise.

Fortunately, many reporters are now sharing direct guidance on how a founder or marketing lead can be best set up for success. Much of these tips can be applied to other reporters — when in doubt, look through their recent bylines and tweets to make sure they want to tell the kind of story you have to offer!

Christine Hall (TechCrunch): What I Cover & How to Pitch Me

Melia Russell (Business Insider): Why certain pitches win

Walter Thompson (TechCrunch): How to pitch Walter Thompson

Suggested by Caleb Bushner, Vice President of Marketing, Unusual Ventures

Savio Martin includes Blush – a free illustration tool – in his list of best design tools for startups.

Savio Martin’s Twitter lists

For curated lists of tools

What does a 14-year-old web developer know about building useful products? More than you might think. 

Not only is Savio Martin a frontend dev whom ProductHunt named Maker of the Year 2021, he’s also a treasure trove of resource lists, like the best design tools for startups, which he says will save you 100+ hours researching.

Recommended by Jamie Langskov, Senior Director of Community, Unusual Ventures

Y Combinator Safe Financing Documents

For early-stage investment documents

Looking for legal documents to solidify your first round of funding? Y Combinator rounds up a collection of standard SAFE documents — such as Safe: Valuation Cap, no Discount; Pro Rata Side Letter; and Safe: MFN, no Valuation Cap, no Discount

These documents are widely accepted and make the process smooth for everyone involved.

Recommended by Rachel Star, Principal Investor, Unusual Ventures

Twilio documentation

For developer documentation best practices

Great examples are fundamental to any learning experience. This is especially true when you’re in the middle of actually doing the thing you need to learn about. It’s at that moment that you realize you need some help and have all the right brain paths triggered to help you recognize and learn from a great example.

As a founder or team member in a startup software company, you’ll need to write documentation in order to make your users successful and drive adoption. When you reach the point where you pause to think, “Is this going to be helpful?”, “I don’t love this. How do I make this better?” or worst of all, “That should do it.” :-) we encourage you to look at Twilio’s documentation. 

They always manage to organize a quick win (“Send your first message”) together with onboarding (“GET STARTED”) and the other docs you’re going to need to be successful in a way that is easy to navigate and enjoyable to use. This pattern of anticipating how to make users successful persists as you drive deeper into their docs, because they care deeply about and understand the developer experience.


Recommended by Shannon Bradshaw, Education Partner, Unusual Ventures

Sketchdeck’s design for Metapack’s Delivery Conference 


For rapid design services

If you can dream it, Sketchdeck can probably design it. Logos, presentations, infographics, and landing pages are just a handful of the collateral that the San Jose–based agency designs from scratch. Sketchdeck specializes in early-stage companies that need access to 24/7 services.

Recommended by Scott Schwarzhoff, Unusual’s Operating Partner who oversees founder services team responsible for embedding alongside founders to help build their early-stage teams as they find product-market fit.

Medium startup publications

For inspiring founder stories 

If you’re a startup story junkie, you’ll love the evergrowing content curated by Medium’s slew of startup publications, including Entrepreneur's Handbook, Mission.org, Startup It Up, Startup Grind, and Marker. Here you’ll find gems like: 

Adam Grant’s favorite leadership books

How My CEO Went from $0 to $30 Million with the OKR Strategy

The greatest sales deck I’ve ever seen (Zuora’s sales deck; a lesson in strategic narrative via Andy Raskin).

If you’re looking for more tactical and technical insights, check out Dev Genius, UX Collective, and CodeX

Medium does have a paywall ($5 per month), but many of the contributors earn money from their writing — and anyone can publish on Medium — making it a moneymaker opportunity for some.

Recommended by Amy Cuevas Schroeder, Director of Educational Content, Unusual Ventures

The Beginner’s Guide to Candidate Personas on Glassdoor

For startup hiring

What are candidate personas and what can you use them for? Good question. Similar to buyer personas, candidate personas are a semi-fictional representation of your ideal job candidate. You can use candidate personas to create job descriptions, employer brand materials, and more. 

Dig into this step-by-step guide for getting started.

Recommended by Jon Volk, Talent Partner, Unusual Ventures

Jason Lemkin’s Saastr.com posts 

For early-stage SaaS advice

Did you know that 60% of Asana’s customers come from self-service, 40% from sales? Or that only 2,800 of MongoDB’s customers went through the sales team; the other 23,000 self-served? These are the kinds of golden nuggets you’ll mine from Jason Lemkin’s blog posts on SaaStr, the largest community for B2B/SaaS founders. 

Recommended reading: The Top 5 Mistakes Every SaaS Salesperson must avoid.

Recommended by Todd Busler, Sales Operator, Unusual Ventures

The Kellblog by Dave Kellog

For enterprise software GTM strategies


Dave Kellogg is a respected advisor, director, consultant, angel investor, and blogger focused on enterprise software startups. He’s served as the CEO, CMO, and independent director across more than 10 companies, ranging in size from zero to over $1B in revenues — including Host Analytics, Salesforce, MarkLogic, and Business Objects. 

Recommended by Sandhya Hegde, General Partner, Unusual Ventures

Startup Field Guide by Unusual Ventures

For step-by-step advice designed for SaaS startups

If you’re looking for tactical, step-by-step insights into how to reach product-market fit for your B2B SaaS product, you’ll likely find it in The Field Guide. You might be surprised by how open some of the entrepreneurs and experts are in sharing what works and what doesn’t. Here you can read insights from Unusual Co-Founders John Vrionis and Jyoti Bansal on scaling AppDynamics from a startup with five customers into one that Cisco acquired for $3.7 billion.

You’ll also find advice on picking the right design partners at the Seed Stage, how to create a Modern GTM for enterprise software, and one of the most detailed guides for creating effective tutorials on the Internet.

Recommended by Elizabeth Lawler, Co-Founder of AppLand

So many startup resources, so little time. 

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