In this Deep Dive I chat to my friend and entrepreneur Cliff Weitzman about Life Planning, coding and success. Some of the highlights from our discussion can be found below, as well as time-stamps if you fancy listening to us talk :)

Cliff Weitzman is the founder / CEO of Speechify - the #1 text-to-speech-audiobooks app - and top #10 grossing on the AppStore. In 2017, Weitzman was named to Forbes magazine's 30 Under 30 list. A senior at Brown University and Google Student ambassador, Weitzman is a dyslexia advocate. He is one of the CEOs discussed in the book The Great CEO Within.

πŸ‘±πŸΌβ€β™‚οΈ Cliff Β πŸ“Έ Instagram / πŸ“šFacebook / β›“LinkedIn / πŸ₯©Medium / 🎧Speechify

Books Mentioned


Fantasy Books

Historical Fiction


00:10 – Cliff’s Background
03:00 – Getting Started In Business + Speechify
09:30 – Ideas For Products and Businesses
12:05 – Learning to Code
15:25 –
19:10 – On Audiobooks and Listening
20:50 – Speechify Introduction + Demo
33:45 – Listening at 2x Speed
41:00 – How can we actively engage with the material when listening?
45:30 – Finding PDFs to Create Free Audiobooks
46:15 – More Advantages of 2x Speed
47:30 – Personal Growth and Self Development and Life Planning
01:00:00 – The Value of Travel
01:16:30 – Happiness or Adventure?
01:20:25 – Wider Purpose
01:29:00 – On Goals
01:34:00 – β€˜Life Is Like A Video Game’
01:36:30 – Advice To Younger Self
01:39:50 – On Health, Fitness + Exercise
01:48:40 – Fantasy Books

Highlights From Our Discussion

Background History

  • One of the youngest people on the Forbes Under 30 list.
  • Obsession with audiobooks born out of learning English through listening to Harry Potter aged 13.
  • Initially found it difficult to do all the readings when he started college due to dyslexia which led to him building the app that turned text to speech to help manage school life.
  • Went on to build 36 different products whilst he was at college.

On Entrepreneurship

  • Important to be intellectually curious and be confident about asking questions – this means that you learn more about the world than other people do, making you more confident to pursue your own projects as you get older.
  • Use books to continue to fuel your intellectual curiosity – Cliff talks about the 4-Hour Work Week which changed his life.
  • Learning to code is essential – it’s so much easier to make a product by coding than it is by making a physical product. Without tooling costs, it’s much more efficient.
  • Look to create something that you know you would’ve found helpful in your own personal life but you know that other people would benefit from as well.

On Ideas

  • You can see Cliff’s TEDx talk about ideas here.
  • Two key things that you can do:
Consistently ask yourself – β€œThis sucks, how can I fix it” whenever you encounter a problem – in other words, train yourself to reflexively think how you could fix an issue when you encounter it in society.
  • Search for opportunities based on what is trending in society more broadly.

On Learning To Code

  • Learning to code gives you an idea of what is possible AND it gives you the skills to build something when you encounter a problem.
You cannot be a founder in 2020 without knowing the basics of coding.
  • To code, you don’t need to know maths or have a computer science degree. There’s a difference between computer science and programming – programming the front-end interface of a web app or an iPhone app is the same level of difficulty as learning how to use Google Sheets or Google Docs.
  • Everyone can learn – it’s a matter of perseverance.
It’s like learning a new language that allows you think in an algorithmic way.

On Audiobooks

  • Every person has about two hours of passive time in the day when they are doing other stuff such as cooking, driving, when you could be listening.
  • It’s one of the very habits that you can develop and incorporate into your life.

On Listening 2x Speed

  • Movies used to be much slower than they are today. Movies today are oriented to be so much faster because we are used to faster applications – our minds have become faster.
  • Our brains adjust to faster speeds the more we listen at those faster speeds – it’s a case of getting used to the faster speed.
  • Speechify has an automatic speed ramping algorithm that increases your listening speed by 3 words per minute every 1,000 words – you don’t notice the incremental increase but overall your listening speed will increase.
  • Always challenge yourself to listen at the fastest speed whilst still comprehending and not being 100% comfortable. By being just slightly uncomfortable you can increase your listening speed over time.
  • Reading is a very active activity – when you read 70% of your brain is dedicated to decoding the words on the page, 30% is dedicated to actually comprehending. When you listen the ration is more akin to 5% : 95%.
  • You shouldn’t expect to be a good listener immediately – it takes practice. But once you get to your 11th audiobook you’ll start to see the benefits. You’ll be able to comprehend more, your speed will increase and you’ll be able to multi-task whilst listening.

On Speechify

  • Outsourcing the cognitive workload of computing the words so that you can focus more on the content as opposed to the computation of the words.
  • If you can find a PDF – open it in Speechify, you then have a free audiobook.

On Personal Growth + Self Development

My only fear in life is not living up to my potential. So my number one passion is to make myself the best person that I can be.
A little bit of slope makes up for a lot of y-intercept.

On Relationships + Confidence

  • Reading How To Win Friends and Influence People by Dale Carnegie changed Cliff’s approach to relationships and has had measurable benefits in how he interacts with people.
  • β€œRelationships are the most important part of life – the most important decisions that you make is who you marry, who you spend all your time with, who your friends are”.
  • Practising the β€˜Comfort Challenges’ from Tim Ferris’ 4 Hour Work Week provides you with the confidence to engage with anyone – reducing your inhibitions and enabling you to feel confident talking to anyone of any status.

On Travel

The only reason I travel is to meet new people – people should use travel as a means of making friends and contacts around the world.
If there is an opportunity, I’ll book a flight and go there. My work still comes before everything but all I need is my laptop and an internet connection.

On Happiness

Be ruthless about cutting the things that are not important to you and invest everything in the things that you care about.
  • Identify the pillars in your life that make you happy and work on them and those goals first.
I optimise only for the things that I want and I’m ruthless about cutting everything else.
  • Long term happiness can be achieved through working on your pillars but you can add spice and joy in the middle which usually come from adventures.

On Purpose

  • Essay by Emerson called On Wealth – talks about humans have ability to apply their thoughts and matter, rearrange atoms in a certain way and create value that is greater than the sum of its parts.
I wanted to build a billion-dollar business but I thought to myself that I want to build a business that does good in the world already. I don’t want to build a financial company etc – it took me a long time to figure out what that thing was. The reason I built Speechify was because when I was 10 years old, the most difficult part of my life was being dyslexic which was preventing me from being what I wanted to be. Eventually I found a way round it with audiobooks and text to speech and it completely changed my life.
The line that I live is – β€˜above all else, the most important thing is to be the person that you needed most when you were young'.
  • Recommendations for working out what you want to do in life:
  • Write out short term goals and identify the resources that you’ll need to hit them.
  • Think about what your goals are going to be when you’re 30/35/40.
  • Everything after that should be working out how you can add value to the world and help people.

On Goals

You are not tied to your goals – your goals are not weights that you are responsible for or you have an obligation to.
  • Goals should only be there to help you accelerate something – it’s not about measuring anything it just helps you along the way there.
  • Pick a goal in order to set the direction but focus on the system that gets you there but in a way that is not just flailing around without a purpose.

On Advice To Younger Self

Knowledge is a tree – you build your baseline trunk at school and every time you have an interaction or read a book, it’s like a new leaf of information and if you’ve got a branch to hang it on, it’ll stay. So you want to build the most fleshed out tree possible.
  • The other way to think of it is in terms of Google Maps – you want to try to make sure there are fewer areas that are pixelated and so from the youngest age possible you want to make an accurate map of the world and the best way to do that is to consume as much information as possible which is easiest to do through books.