Three Pivots in One

My story of switching job functions, sector focus, and lifestyle in the past year

Massimiliano Hasan
11 min readAug 4, 2023

In the last 12 months, I made three major life changes: I switched job function, sector focus, and lifestyle all in one go. These changes came at the heels of a transformative professional sabbatical wherein I fully took a career break in order to attend graduate school at MIT (you can read more about that decision here).

The common thread between these three pivots is BFA Global & Catalyst Fund. After cold emailing one of their executives whom I had met in passing at a conference six years prior, I was fortunate enough to have received an offer to work for them. Also serendipitously, their Cambridge office was a mere T stop away from my apartment in Kendall square. I will forever be grateful to David and Maelis for giving me the opportunity to work for this uniquely impactful organization. Oh and by the way, they’re hiring in case you’re interested, so take a look and don’t hesitate to reach out by email at with a brief background and role in question.

I will use the following three sections to break down how I’ve adapted to each respective change to share my learnings and potentially inspire others how they might do the same:

  1. From Startups to VC
  2. From FinTech to Climate
  3. From Physical Distance to Digital Nomad
Me, at a crossroads in life with a literal zebra crossing!

From Startups to VC

While I’ve dabbled in a variety of roles throughout my career, my primary function has been operating and scaling FinTech startups, typically with a data analytics specialization. From Kiva to Oportun to Gojek to Pintek, I was in the trenches building data warehouses, developing dashboards, deploying underwriting models, running A/B tests, writing SQL & Python code, debugging data governance issues, and analyzing mind-numbing amounts of data. As the go-to person on all data matters, I would at times have interactions with investors — even though they were not my main focus area — so I had a high-level understanding of what their work entailed. I also had some experience at Kiva in underwriting loans to social enterprises so understood the process of capital deployment to growing businesses, albeit from a debt perspective. Thus, when I joined Catalyst Fund and was initially tasked with sourcing new startups to invest in, including owning the end-to-end due diligence on a couple of potential portfolio companies, I certainly felt a bit of impostor syndrome.

The harder

The toughest part for me was the initial stage of sourcing because I lacked experience in understanding what initial signals to look for in order to determine which pre-seed stage startup would be worthwhile shortlisting for further due diligence. Moreover, I lacked familiarity with some of the business models because I had been so steeped in the FinTech world; regenerative agriculture, direct air carbon capture, clean cookstoves, solar microgrids… you may as well have spoken a different language to me!

In all, our team went through around 2,000 pitch decks in order to find ten to invest in, which represents an acceptance rate of 0.5% (and I thought getting into MIT was tough enough!). I was so accustomed to making decisions only after analyzing large amounts of data, studying a dashboard, or running an experiment, that I found it quite tricky to make decisions on the fly based on pitch decks with less than a dozen slides.

The easier

There were 2 areas in particular that came quite naturally to me: financial modeling and understanding the underlying technology.

When it came time to create projections on the startups’ financials, I felt my coursework on accounting and finance from a decade ago, as well as my years of working closely with FP&A teams at FinTech startups, kicking in. To me, the numbers in their balance sheets, income statements, invoices, budgets, etc. were far more tangible decision-making drivers. However, one thing that I eventually came to realize is that financial models are far less accurate at earlier stages of startups and thus less emphasized in the final decision making. If you are a pre-seed or seed stage startup that has yet to find product market fit, by definition your financials will not be in a steady state so any assumptions made in order to project future months or years of cash flows will be shaky as a result. As such, there tended to be more of an emphasis on the team and the market opportunity over and above financials to drive a decision during the due diligence process.

The other area that came quite naturally to me was on understanding the underlying technology of the product. As part of my prior responsibilities, I tended to work most closely with product managers (PMs) and engineers amongst other functions. This is because PMs tended to be the most demanding stakeholders of our outputs, while we tended to work closely with engineers on the technology architecture as well as data governance & security matters. One of the most interesting conundrums that continuously emerged in conversation was around the build vs buy dilemma. This decision can really be life or death for early stage startups, especially those in emerging markets. It was a common theme across pretty much the entire cohort of portfolio companies. I am glad to have had not just colleagues like Ken & Kevin to discuss this topic with, but also external thought leaders like my former colleague, Ajey (check out this great piece from him on this topic), who was also kind enough to advise one of our Kenyan portfolio companies on this topic.

The bottom line

To be honest, the most important way to move up this learning curve for me was to simply shadow and emulate my colleagues with much more experience than myself. While I did of course consume content from the likes of YC, Sequoia, and a16z, as well as read a couple of memoirs from high-impact startups in emerging markets (Let There d.light by Dorcas Cheng Tozun & Failing to Win by Mike Quinn); I would say that my learning was 80% informed by my hands-on, on-the-job work rather than passive reading of content. I had the pleasure of working with incredible founders on the African continent building across the InsurTech, HealthTech and AgriTech verticals, respectively (shout-outs to Paddy Cover, Eight Medical and Farm to Feed).

With the Catalyst Fund team and founders last February in Nairobi, Kenya

From FinTech to Climate

Growing up with plenty of outdoor activities like surfing, climbing, and kayaking (see below for a neat kayaking experience in mangroves, one of the most potent nature-based carbon sinks we have!), our planet has always been fascinating to me. In fact, the first AP class that I took in high school was AP Environment! Throughout my career, I’ve also had some opportunities to gain exposure to the climate and sustainability space through serving on the board for my brother’s sustainable hat startup Topiku, investing in my friend’s waste-to-value tech startup Sampangan and advising the waste management organization Bank Sampah through Ashoka. However, I’ve never truly worked in a full-time role dedicated to climate, sustainability, and/or the environment.

Kayaking with my dad in a mangrove reserve in — believe it or not — Jakarta, Indonesia

I joined BFA Global & Catalyst Fund at an interesting time; similar to me, the organization and fund were at an inflection point in pivoting their focus from FinTech/financial inclusion towards climate resilience. It became apparent that I needed to upskill quickly, but unlike the more on-the-job learning from a functional perspective, this time I actually relied heavily on consuming books, articles, papers, and one podcast in particular, as there weren’t too many in-house experts to turn to. Below is a selection of the content that I found particularly informative:

It’s worth mentioning that the term “climate” may mean different things to different folks. I find it useful to generally think about the climate finance space in terms of climate mitigation and adaptation. Climate mitigation solutions are geared towards decarbonization and/or offsets, whereas climate adaptation solutions are focused on bolstering the resilience of communities in the face of ongoing climate risks. The aforementioned resources tend to discuss more climate mitigation solutions, of which there is indeed a larger funding gap: $3.4T needed annually between 2020–2025 vis-à-vis $160–340B needed by 2030 for adaptation and resilience, an order of magnitude difference. At Catalyst Fund in particular, the investment thesis is more focused on climate adaptation and resilience, which is why I worked with startups operating in verticals as diverse as HealthTech, InsurTech, and AgriTech; while their models were quite different, they shared a focus on delivering value to underserved, climate vulnerable users.

For instance smallholder farmers are amongst the most climate vulnerable populations across the developing world, so building solutions that protect their livelihoods and boost their incomes help drive their resilience to climate change-linked shocks. That’s why Catalyst Fund has backed startups like Farm to Feed who are solving food waste to boost the incomes of smallholder farmers in Kenya, and Agro Supply who are supporting smallholder farmers with savings, inputs and insurance in Uganda. It’s crazy to think that this time last year, I knew almost nothing about the intersection between climate resilience and agriculture, yet I just published an article last month on this very topic (read more here). As data from this past record-breaking summer heat has shown, it is important for us to not neglect climate resilience as an area to invest resources, so I’m proud of the work that Catalyst Fund has done so far and happy to see others like Radical Fund and Mercy Corps Ventures tackling the issue as well.

Enjoying a break at Hell’s Gate National Park in Kenya with my colleagues, Ken and Javi. Fun fact: it’s supposedly this very rock that inspired the famous opening scene in the Lion King!

From Physical Distance to Digital Nomad

At the end of June 2022, I moved out of my apartment in Cambridge, Massachusetts. This was only a mere 2 months after MIT removed COVID testing mandates and masking on campus. In the 12 months between July 2022 to July 2023, I traveled to 5 continents: spending 4 months in Asia, 4 months in North America, 2 months in Africa, 1 month in Europe and 1 month in South America.

While I’ve always been an avid traveler having grown up between 3 countries (USA, Indonesia, Singapore) I’d never quite lived a lifestyle that was so mobile — with the average tenure spent in each city amounting to 1–2 weeks. What’s interesting is that only about 20% of this was for work, with a larger chunk actually due to weddings… of which I attended no less than 9!

Here are some tips on how I was able to survive digital nomad life:

  • Computer: invest in a portable screen to save your eyes and lightweight laptop to save your back! I use ViewSonic VG1655 for my portable screen and ASUS ZenBook as my laptop (see photo below from my work set up on a trip to Bali this past May).
My typical working set up during a trip in Bali, Indonesia (I had 6 separate trips to the island in 12 months!)
  • Audio: MIT students & alumni get exclusive Bose discounts so I use that exclusively, specifically the QuietComfort 45 noise-canceling headphones for all of my Zoom calls, the QuietComfort Earbuds for working out or listening to podcasts, and the SoundLink Flex portable speaker for small group gatherings. Noise-cancellation is very necessary when you’re either in a plane filled with crying babies or a cafe filled with loud chatter.
  • Phone: I initially used Google Fi but the service grew worse over time so I switched to a dual sim Pixel 7 where I use my US number and have the option of changing the other eSIM slot to get a local number wherever I travel; while I haven’t yet used it, there’s a startup based out of Singapore worth looking into called Airalo that facilitates eSIM purchases.
  • Credit card: Chase Sapphire Reserve, the travel-related point multipliers make the annual fee worth it and you also get other perks like travel disruption insurance, automatic lounge access, etc.
  • Travel loyalty: loyalty programs are super worth it for both airlines and hotels; given the amount of globalization and consolidation lately, it actually is fairly easier to stick with one hotel group and airline association as you book travel. I find Marriott Bonvoy and Singapore Airlines (Star Alliance) cover a lot of bases.
  • Reading: Kindle is the way to go, as much as I love physical books they get heavy fast! See the prior sections for the books that were on my reading list.
  • Publications: I relied heavily on the Rest of World, The World, The Economist newsletters to stay up-to-date on the latest on global affairs.
  • Bags & suitcases: Away, Ethnotek and Eiger are my go-to brand choices (see below photo for how I typically look with all my luggage).
Just finished picking up baggage in Soekarno-Hatta airport in Tangerang, Indonesia
  • Shoes: Allbirds for my single pair of casual shoes (see above photo), Vivobarefoot for my single pair of running/workout shoes, and a pair of Chelsea boots for fancier occasions.
  • Beating jet lag: I have a bit of a caffeine addiction so definitely relied on a lot of coffee throughout, but to get real serious shuteye I would pop a melatonin and use a sleeping mask, neck pillow and earplugs. Also, in order to reboot circadian rhythms, sunlight exposure is crucial, so I try to maximize that upon waking as soon as possible. Finally, maintaining a healthy fitness routine can be tricky while being on the move but I always made sure to squeeze a run, yoga, or climb (I actually visited 2 dozen climbing gyms around the world during my travels!) before going on with my day. Such habits can help you feel a bit more grounded and conquer the jetlag faster. See below for my first ever triathlon finish, a race that I did in the midst of my digital nomad lifestyle.
First Olympic distance triathlon completed in Batam, Indonesia in May 2023. This was actually supposed to take place in May 2020 but the pandemic had other plans…

Whether you’re considering switching functions from tech startup to VC investor, transitioning sectors from FinTech to climate, and/or wanting to become a digital nomad, I hope that my story can serve as some inspiration. I’m always to discuss any of the above further. Feel free to contact me via email at with any questions, happy to chat :)