The Art of The Impossible: What It Takes To Be A Founder

Welcome to The Art of The Impossible, a weekly newsletter where I unearth five pieces of content which I hope will both inspire and embolden you.

PODCAST

This week's guest is investor, founder, community builder and author Matthew Stafford and in this episode we discuss:

• What he looks for in a founder
• The pitfalls all founders should avoid when fundraising
• Why startup success and building a network are interlinked
• And the three books he recommends to ALL founders

Listen on Spotify here or wherever it is you get your podcasts from.

Enjoy!

QUOTE

INTERVIEW

Last week, I first learned about Christina Cacioppo and her billion dollar software company. In her career before Vanta, Christina has backed early-stage startups at Union Square Ventures, took Dropbox Paper to market (as Product Manager), and is now revolutionizing security monitoring at Vanta as co-founder and CEO - her billion dollar startup.

To learn more about Christina, read this interview:

Then watch this interview she did at Slush in 2021.

BOOK

Super Founders: What Data Reveals About Billion-Dollar Startups by Ali Tamaseb .

I just ordered this book so will let you know how I get on but I have heard really good things about it.

From Amazon:

Super Founders uses a data-driven approach to understand what really differentiates billion-dollar start-ups from the rest.

Ali Tamaseb has spent thousands of hours manually amassing what may be the largest dataset ever collected on start-ups, comparing billion-dollar start-ups with those that failed to become one - 30,000 data points on nearly every factor: number of competitors, market size, the founder’s age, their university’s ranking, quality of investors, fundraising time, and many, many more. And what he found looked far different than expected. Just to mention a few: 

• Most unicorn founders had no industry experience
• There's no disadvantage to being a solo founder or to being a nontechnical CEO
• < 15% went through any kind of accelerator program
• Over half had strong competitors when starting - being first to market with an idea does not actually matter

You will also hear the stories of the early days of billion-dollar start-ups firsthand. The book includes exclusive interviews with the founders/investors of Zoom, Instacart, PayPal, Nest, Github, Flatiron Health, Kite Pharma, Facebook, Stripe, Airbnb, YouTube, LinkedIn, Lyft, DoorDash, Coinbase, and Square, venture capital investors like Elad Gil, Peter Thiel, Alfred Lin from Sequoia Capital and Keith Rabois of Founders Fund, as well as previously untold stories about the early days of ByteDance (TikTok), WhatsApp, Dropbox, Discord, DiDi, Flipkart, Instagram, Careem, Peloton, and SpaceX.

Packed with counterintuitive insights and inside stories from people who have built massively successful companies, Super Founders is also an actionable guide for entrepreneurs, investors, and anyone interested in what makes a start-up successful. 

Buy Super Founders here.

WATCH

I saw someone describe this interview as a masterclass and if you watch it, you will see why.

It's Airbnb co-founder Brian Chesky (the only designer-founder in the Fortune 500) in conversation with Figma co-founder Dylan Field , discussing how to lead a company through uncertainty with stories about reorganising the company just before going public in early 2020 to surviving after losing 80% of Airbnb's business during Covid, and more.

An inspirational talk, well-worth your time.

--------------

Thank you for reading the newsletter and for listening to the podcast, and if you enjoy them, please do share with your network - my goal is to have these stories reach as many as possible so that others can be inspired too.

Until next time...

Danielle

PS Can you do me a favour? If you like the podcast, could you please leave a short review on whatever platform you use? It would mean so much to me and will help others find it too.

Thank you!