Startup Inspiration

Having a start-up is hard work. And it can be lonely too. Even when you have partners in the business. Even if your friends and family are giving you moral or financial support, or both. Upstarts shares inspiration for founders.

Having a startup is hard work. And it can be lonely too. Even when you have partners in the business. Even if your friends and family are giving you moral or financial support, or both. 

Seriously, if you don’t have doubts you’re not trying hard enough! 

So I’m sharing some of the startup focused books, essays, podcasts, documentaries and television series that help me stay positive and pragmatic about the ecosystem.

What inspires you? Contact Upstarts.


How to Start a Startup by Paul Graham (2005)

It is 2022. How have I never heard of Paul Graham before? I wish I had read his brilliant article “How to start a startup”, adapted from a talk he gave to the Harvard Computer Society in March of 2005, before I started my business. 

Written with great good humour and common sense, Dr. Graham’s insights can assist any member of the Upstart community. I already knew why my journey did not conclude as I had hoped, but Dr. Graham shows the inevitability of my outcome.

How I Built This

“How I Built This ”, a podcast hosted by Guy Raz, is engaging and informative.

When things get dark as a founder it is helpful to find inspiration from people who have succeeded. Guess what? Most Founders “confide” that they had problems to overcome before realizing their dreams. The classic hero’s journey narrative arc makes these stories gripping. 

I have been surprised to find that I am just as inspired by people running businesses that I thought I had no interest in, as I am by those founders that created products and services that I am familiar with.

Good news! Guy’s experience interviewing founders has been made into a book. How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs by Guy Raz, was published March 2022 by Harvest. 


General Magic

This is a fascinating documentary about having the right ideas at the wrong time. The film documents a company that emerged from Apple, that was imaging visionary products that would eventually be realized as the iPad, the iPhone and various other now ubiquitous technologies. Unfortunately, their imaginations were ahead of what the tech could do. Many of people involved in this company went on to do amazing things.

The Inventor (Documentary) and The Drop Out (TV series and Podcast)

The story of Theranos founder Elizabeth Holmes is a cautionary tale of taking “fake it til you make it” to dangerous extremes. Ms Holmes was once revered as a unicorn, young female founder with a clear vision. Earlier this year she was found guilty of three counts of wire fraud and one count of conspiracy to commit wire fraud, as a result of claims she made to investors.

By misrepresenting the effectiveness of its tech, Theranos compromised the health and well-being of patients and mislead her customers. Still, I cannot help but feeling some sympathy for Ms. Holmes who found herself trapped in the start-up paradox and appears to me to have been completely convinced by her mission.

Silicon Valley

HBO’s “Silicon Valley” is a hilarious send-up of the the self-referential nature of the start-up industry. I especially like seasons 1 and 2.  It can be vulgar, but it is nice to laugh at an industry that takes itself too seriously.  Not everyone is “making the world a better place”, most founders really just want to make money. The ups and downs of the fictional Pied Piper team actually resonate with me, even though I’m a non-technical founder who doesn’t live in one of the magical tech hubs. “Silicon Valley” is available to stream in most markets.