The case for having a portfolio of small bets

Abha Malpani Naismith
4 min readJul 22, 2023


A path towards time and financial independence

Photo by Markus Winkler on Unsplash

For the last two years I have been thinking about how I can design my work around my life, rather than my life around my work.

Dependency on my employer for a salary, lack of schedule flexibility and lack of extrinsic motivation, accelerated my decision to resign from my current job.

Consistent news of massive layoffs, be it during Covid or more recently, have only made my conviction to not have all my eggs in one basket, stronger.

Small Bets: A path towards time and financial independence

Seeking time flexibility and financial freedom over the last two years, I have been exploring my options and placing my own ‘small bets.’

Coined by Daniel Vassallo, ex-Amazon engineer turned solopreneur who now makes almost $500K, ‘small bets’ means working on multiple small, no risk projects at the same time, to see what has potential before deciding on which one to invest more in. In 2019, Daniel quit his $500K job at Amazon to live life on his own terms.

Today, “Small Bets” is also the name of Daniel’s community of over 2400 amazing individuals from all walks of life with the same goal: to design a life where they can thrive on their own terms.

My Small Bets so far:

I launched this newsletter.

I launched a free email course on how to make your first dollar online.

I launched a cohort for mums interested in exploring the creator economy.

I’ve published 17 books on Amazon KDP.

I’ve started affiliate marketing.

I’m in process of launching my own digital course for women in business — more on that soon!

And I’ve decided to launch another newsletter and perhaps a niche site.

And, now that I am finishing up at my job, I will open up to freelance assignments.

“When we’re not certain of the right answer, the best approach is to have a portfolio, a range of bets that reward us with resilience and significant upside,” says Seth Godin in his blog on portfolio thinking. “An example can be something as simple as what to put on the buffet–if you’re not sure who’s coming to the meeting, it makes sense to have a variety of options, because the chances you’ll get it right go way up.”

On being open to randomness and serendipity

Do I know what will work? No.

Am at attached deeply to any of my small bets? Not really.

Am I open to following my curiosity if something random comes my way? Absolutely.

“Business is more random than it seems. It’s very hard to predict (or imagine) what will work and what won’t. It’s not even easy to imagine what we’ll like doing or dislike. We just have to try many things. Many small, safe-to-fail experiments. We learn by trial and error; not only what works as a business, but also what business works for our preferred lifestyle.” — Daniel Vassallo

What needs to matter the most is:

  • Enjoying what we do
  • Our resilience to the ever changing environment
  • Maintaining your intrinsic motivation, as extrinsic motivation doesn’t last (eg motivation that is linked to salary and position)

I wrote a post a few months ago on choosing your focus where I reference Warren Buffett’s 25/5 rule — basically choosing only 5 things to focus on at a time.

Placing multiple small bets might seem contrary to this way of thinking, however if my focus is the above three points, that would be another way to eliminate everything that doesn’t align with them.

On staying motivated and inspired

“If you want to work for yourself, my best recommendation for you is to find your own inspiration generator. Something that on a daily basis exposes you to random things that you would have never thought of on your own. Over time, you will improve your selection criteria, and get better at choosing what things are worth trying. But the very first thing to do is to find your inspiration generator.” Daniel Vassallo

Photo by CJ Dayrit on Unsplash

My inspiration generator is the 50+ newsletters I subscribe to. Going through them is the highlight of my day and I am always left with so many ideas to keep me learning and bursting with inspiration. Thanks to Notion, I am able to save them somewhere on the go!

On planning your own insurance

If you are looking to transition out of your corporate job, or perhaps looking to better navigate inflation, pay off debt or save up for a dream holiday, having a portfolio of small bets can serve as an insurance of sorts.

Do you have any small bets? Has this article given you an ideas for small bets?

Join the Small Bets Community

If you are interested in learning more about Daniel Vassallo’s Small Bets Community, you can sign up through this link. Membership is a onetime fee for lifetime access and I highly recommend it if you are looking to experiment with some small bets.

*This post contains some affiliate links which means that if you make a purchase from any of them, I get a small commission at no extra cost to you. I only share products, tools and solutions I truly believe in.



Abha Malpani Naismith

Communications professional. Digital strategist. Writer. Mum. AI enthusiast. Newsletter for working mums.