Investor's note
Finding Fintech
I stumbled into the world of fintech. I spent years studying how to be a lawyer, convinced that I wanted to learn the ins and outs of how to navigate the legal world. That changed when I went to the IncMty conference and met the two co-founders for Clip, a Square for LATAM providing new payment infrastructure for local merchants. They sold me on a vision of being able to empower small businesses, like a taco shop, to accept cards using simple, affordable technology, changing the financial lives of SME owners in Mexico.
When I joined Clip I had no idea what product was and found myself doing everything, from risk chargeback to tinkering with the hardware to looking through our data analytics dashboard. As I eventually began to get myself out of the weeds, I developed a great relationship with the CTO and co-founder, who began to introduce me to three pillars of what great product people focus on: Business Development, Engineering, and Design.
As I was upskilling as a product manager, the emphasis on what made a great product manager helped highlight why I was drawn to the intersection of finance and technology. To me, Financial Services are completely outdated. When you bring user design, consumer thinking, and first principles to the space, you understand how you could build cheaper, more effective products, unlock financial services to more people and automate processes to make complex solutions simple.
However, I would place a heavy emphasis on the complexity. Whenever I get asked what I do or where I work, I never go in-depth on what Checkout does and especially not what products I am specifically leading. I know from experience it’s the fastest way for their eyes to slowly glaze over.
Joining On Deck To Expand My Fintech Bubble
Before joining ODFintech I had small fintech bubble - consisting of co-workers, friends, and online acquaintances that would occasionally talk about the space. However, I often found that we formed similar perspectives from working at the same company or being in the same geography.
I joined the On Deck Fintech Fellowship to get outside of my bubble, staying within the fintech ecosystem getting access to a curated community to ensure a high degree of experience. I wanted a community where I could get on a 1:1 with someone knowing they would be interested to discuss why Visa Mastercard is so big or what we could learn from the newest fintech startup that just raised.
The other reason I joined the fellowship was to see how other builders were operating in fintech. I’ve learned how fintech companies operate in the US and UK and what the predominant theories driving the space are, but I welcomed the different perspectives someone in Asia or Africa. I wanted to learn how they were thinking about payments, or crypto, or what problems they were focused on solving. From these conversations, my team at Checkout is now thinking about how we can expand our product to other regions beyond the UK/EEA.
By the fourth week of the fellowship, I felt like I had developed an immediate operator network of peers from a similar background. The core group includes Hannah Zaidi at Wealthsimple and Sophia Goldberg at Adyen. With Hannah, it’s a space where both of us can brainstorm ideas, share our love for compliance and break down the components of why things work or won’t work at different companies. With Sophia, our professional positions are identical as product people at well-known acquirers. We have a regular sync where we measure our progress since the last meeting, evaluate blockers, and finally share interesting articles.
Growing as an Entrepreneurial Operator
I spend my weekends as an entrepreneurial operator, working with friends on different projects in fintech. Most recently, we’ve been building an app that serves as a baby between Foursquare and Chime, serving recommendations around your geographic location based on your friends' spending habits.
2 weeks into the cohort I had a brainstorming session with Alex Hartz from SciFi VC, who focuses on marketplaces within fintech, demo’ing the app that I had been working on. I had initially been approaching the product with the consistent mindset that this was always something that was targeted and niche, but the conversation with Alex planted the seed on what opportunity existed to expand the product. We covered everything from how we can retarget users to increase transactional value to creating viral loops to gamifying the purchasing experience.
I believe that the fastest way to grow and improve is to give your ideas, products, and models exposure to smart people. ODFintech allows you to gain this exposure in a 10x way, where one conversation changes the vision of your product and introduces you to a host of other people you should connect with.
The smaller mastermind groups served as a group of therapists helping me cope with the toll of being an entrepreneurial operator. One weekend, I spoke with multiple merchants and realized that I had no business model for the product. After having a view of the world dashed by reality, it’s often difficult to get passionate about building again. Having a group I could share this failure with and get their advice on how to bounce back served as a superpower in continuing to iterate and improve my side project.
Hosting Community Events
Even though the first cohort of the On Deck Fintech fellowship was meant to be an 8-week program, I knew that the return on investment I was going to get was through lifelong friendships and connections. When the program pivoted to a year-long model, I was thrilled to know that I would continue be able to bond with new members of the community.
As London gradually reduced COVID restrictions in the early weeks of the cohort, I began thinking about hosting a community event for the locally-based members of the community. It would finally allow us to connect as a group, expanding my bubble and finding people that wanted to nerd out about fintech.
I also presented in an online community session to the cohort on what we were building at Checkout. After doing the presentation we got an outpouring of responses from people saying, “if you ever need help on compliance, reach out!” or “if you ever want to talk through how we do payments here at x, sign up to my calendly.”
After years of working in the fintech space, I finally feel that I have found my crowd. It’s a community that pushes me both to expand my thinking and perspective, that can help me with both my projects and professional development, and a group that is always down to dive deep into the fintech topics I would never mention to my friends outside the industry.
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The On Deck Fintech Fellowship is a continuous community for founders, investors, and operators working on frontier themes in fintech. The membership combines highly curated programming with a diverse community of practitioners to help you share knowledge, find opportunities, make connections and build the next wave of innovation in financial services — together.
Note: This is part of a series where we talk to On Deck Founders alumni about the companies they’re building and what it will take to propel them to the next level. Consider joining our incredible community of founders who have launched over 1000 companies worth over $9B. Apply here.