
Leaving a $500k job to build a portfolio of small bets - Daniel Vassallo
11/08/21 • 16 min
In 2019 Daniel Vassallo left his $500k salaried job at Amazon to go indie. In the 2 years since he left Daniel has placed many small bets, something he's become known for. In particular Daniel has seen success from his Info Products and building his audience on Twitter, which has grown from 0 to 91k. He wrote a short book on the good parts of AWS, which has made $126,000, then following the Twitter growth, wrote a book called Everyone Can Build a Twitter Audience, which has made $244,000. He shares all of his revenue reports in his Profit and Loss community, which in itself has made over $30k in the past year. In total, and in just over 2 years, Daniel has made $570k in revenue and $306k in profit since leaving his job at Amazon. But he's gained something he didn't have while working for someone else, freedom.
➡️ Get the uncut, 80 minute recording with Daniel on the Indie Feast membership here.
What we covered in this episode:
- Leaving a $500k job at Amazon to go Indie
- The trap of judging your life based on financial value
- Why the initial focusing on one product didn't work out for Daniel
- Where the small bets mindset originated
- How to deal with context switching with small bets
- Dealing with an uncertain income
- Why info products work well for a small bets strategy
- How book publishers work and how we can apply their methods
- The importance of the "small" in small bets
- How you can build a twitter audience like Daniel
- Why Daniel started making wooden cutting boards
- How he made $2,600 from one tweet
Recommendations
- Book: Anti Fragile by Nassim Taleb
- Podcast: Indie Hackers
- Indie Hacker: Peter Askew
More on Daniel
Follow Me
Sponsor - Fathom Analytics
For the longest time, website analytics software was seriously bad. It was hard to understand, time-consuming to use, and worse, it exploited visitor data for big tech to profit. I've spent countless hours in Google Analytics dashboards trying to figure even out the most basic metrics.
This is exactly why I signed up for Fathom as soon as I heard Paul Jarvis and Jack Ellis were building it.
Fathom is simple website analytics that doesn't suck. It's easy to use and respectful of privacy laws, with no cookies following your users around the web. They're also a bootstrapped, sustainable business so I love supporting them. Yes, it might feel strange paying for analytics at first, but once you realise the real cost of free Google Analytics and realising how easy to use Fathom is, you won't go back. You can install the lightweight code on as many websites as you want and quickly see the performance of all your sites.
Link → https://usefathom.com/bites
In 2019 Daniel Vassallo left his $500k salaried job at Amazon to go indie. In the 2 years since he left Daniel has placed many small bets, something he's become known for. In particular Daniel has seen success from his Info Products and building his audience on Twitter, which has grown from 0 to 91k. He wrote a short book on the good parts of AWS, which has made $126,000, then following the Twitter growth, wrote a book called Everyone Can Build a Twitter Audience, which has made $244,000. He shares all of his revenue reports in his Profit and Loss community, which in itself has made over $30k in the past year. In total, and in just over 2 years, Daniel has made $570k in revenue and $306k in profit since leaving his job at Amazon. But he's gained something he didn't have while working for someone else, freedom.
➡️ Get the uncut, 80 minute recording with Daniel on the Indie Feast membership here.
What we covered in this episode:
- Leaving a $500k job at Amazon to go Indie
- The trap of judging your life based on financial value
- Why the initial focusing on one product didn't work out for Daniel
- Where the small bets mindset originated
- How to deal with context switching with small bets
- Dealing with an uncertain income
- Why info products work well for a small bets strategy
- How book publishers work and how we can apply their methods
- The importance of the "small" in small bets
- How you can build a twitter audience like Daniel
- Why Daniel started making wooden cutting boards
- How he made $2,600 from one tweet
Recommendations
- Book: Anti Fragile by Nassim Taleb
- Podcast: Indie Hackers
- Indie Hacker: Peter Askew
More on Daniel
Follow Me
Sponsor - Fathom Analytics
For the longest time, website analytics software was seriously bad. It was hard to understand, time-consuming to use, and worse, it exploited visitor data for big tech to profit. I've spent countless hours in Google Analytics dashboards trying to figure even out the most basic metrics.
This is exactly why I signed up for Fathom as soon as I heard Paul Jarvis and Jack Ellis were building it.
Fathom is simple website analytics that doesn't suck. It's easy to use and respectful of privacy laws, with no cookies following your users around the web. They're also a bootstrapped, sustainable business so I love supporting them. Yes, it might feel strange paying for analytics at first, but once you realise the real cost of free Google Analytics and realising how easy to use Fathom is, you won't go back. You can install the lightweight code on as many websites as you want and quickly see the performance of all your sites.
Link → https://usefathom.com/bites
Previous Episode

From $500k to $1m in 6 months with a podcast agency - Harry Morton, Lowerstreet
Harry Morton is the founder of Lower Street Media, a podcast production agency that specialises in premium podcasts for ambitious companies. Lower Street are the agency behind top shows such as Secret Leaders, Technology Untangled and WFH Daily. Harry's business has skyrocketed since COVID, doubling in size of revenue and headcount in the last 6-months as more companies start to realise how effective podcasting can be. Harry also runs Single Track Conf, a 3-day mountain-biking founder retreat.
➡️ Here's my course on starting a podcast in 2 hours or less (use "bites" for $10 off)
What we covered in this episode:
- Why start an agency? it's not exactly a dream business to start.
- How Harry grew Lowerstreet through cold outreach
- 1st client, Ultimate Leadership Podcast
- Why the productising model didn't work out for Lowerstreet
- What Harry did in the early days for growth
- How losing 30% of revenue was a catalyst for growth
- Doubling the agency revenue in 6 months
- Quitting his job with no savings to start Lowersteet
- Not knowing what to do when starting the company
- Addressing shiny object syndrome
- Why focus vs portfolio of projects argument is BS
- The secret sauce for making a sh*t hot podcast
- How to make a show that stands out
- Starting a mountain bike community
Recommendations
- Book: Out on The Wire by Jessica Abel
- Podcast: Startup
- Indie Hacker: Andrew Wilkinson
Follow Harry
Follow Me
Sponsor - 2 Hour Podcast
Yes, that's right, I'm sponsoring my own show 🤯
After producing hundreds of podcasts for myself and clients, I've been pouring all of my knowledge into my new course, 2 Hour Podcast, which shows you how to start, grow and monetize a podcast that takes you less than 2 hours per week.
I know lots of people who want to start a pod and reap the rewards, but struggle to find the time, which is exactly why I made this course.
I've taken a three-pronged approach to making a podcast efficiently. The first is a step-by-step video guide to creating your show, covering everything from branding, to editing to hosting. The second part is a 90 minute tutorial where I make a my own podcast completely from scratch, recording the first episode with Arvid Kahl, using the tips from part 1. The final prong is my full Notion system for creating my show, including my episode CRM, guest and outreach templates, plus an episode briefing doc.
Head to 2hourpodcast.com to get the full course and get $10 off with the code "bites" at checkout.
Next Episode

From lifelong bootstrapper to raising calm funding - Brian Casel, ZipMessage
Brian Casel is a veteran of the bootstrapping game, having left his full-time job back in 2008. You might have heard him on the Boostrapped Web podcast where he shares his journey starting and building software products. Over the years Brian has pretty much done it all, built software businesses, courses, productized services and even sold some along the way. Most recently, Brian has been working on ZipMessage, a new way to communicate asynchronously.
➡️ Get the uncut, 60 minute recording with Brian on the Indie Feast membership here.
What we covered in this episode:
- Where did the idea of ZipMessage come from?
- How Brian validated ZipMessage
- Brian's unconventional approach to validation
- Why Brian raised funding from Calm Company Fund
- How can people go from freelancer to productized service
- The importance of building processes in productized services
- Why Brian didn't follow his passion for music
Recommendations
- Book: Shoe Dog by Phil Knight
- Podcast: Smartless
- Indie Hacker: James McKinven (errm...)
Follow Brian
Follow Me
Sponsor - Fathom Analytics
For the longest time, website analytics software was seriously bad. It was hard to understand, time-consuming to use, and worse, it exploited visitor data for big tech to profit. I've spent countless hours in Google Analytics dashboards trying to figure even out the most basic metrics.
This is exactly why I signed up for Fathom as soon as I heard Paul Jarvis and Jack Ellis were building it.
Fathom is simple website analytics that doesn't suck. It's easy to use and respectful of privacy laws, with no cookies following your users around the web. They're also a bootstrapped, sustainable business so I love supporting them. Yes, it might feel strange paying for analytics at first, but once you realise the real cost of free Google Analytics and realising how easy to use Fathom is, you won't go back. You can install the lightweight code on as many websites as you want and quickly see the performance of all your sites.
Link → https://usefathom.com/bites
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