Nov 28, 2022

Pinwheel’s Kurt Lin: Build Your Operating System Early, But Know Product-Market Fit ‘Is Like Falling in Love’

Pinwheel cofounders Kurt Lin, Anish Basu, and Curtis Lee came to fintech as outsiders, and their journey to building payroll connectivity APIs was one of iterative discovery. Curtis and Kurt first worked together at Luxe, an on-demand parking company that Curtis founded and was acquired by Volvo; Anish and Curtis connected at social gaming company Zynga. When the group came together to start something new, they were drawn to the idea of an automated HSA (health saving account) to serve the 63 percent of Americans living paycheck to paycheck and therefore unable to prefund them. 
“While building that, we uncovered that there was nothing connecting apps like ours to the massive ecosystem of payroll and HRIS providers that we relied on for our product to exist,” Kurt says. So they talked to other entrepreneurs encountering similar problems and decided to pivot to building the infrastructure that would connect any app to payroll and HRIS providers. 
“Growing up the child of two immigrant parents, I saw firsthand how hard it is for many Americans to access affordable products,” Kurt says. Now, Pinwheel is helping consumers unlock payroll systems data and access better, cheaper financial products and building a fairer financial system for those who need it most. Here’s how he and his team are doing it, and Kurt’s advice for others in the space. 

What’s a key piece of early advice you’d want to give a new fintech founder on day one? 

Hiring well is the most critical thing you can do to increase your probability of success as a founder. Great talent gives you leverage—each new hire should not just double output, they should triple it, quadruple it, or more. When you make a hire, one of two things happens: They have either raised the average of the company or they’ve lowered it. Never ever settle despite the immense pressure you have to fill a role. You will always end up regretting it. Take the extra time early on to be thoughtful about your culture and what type of person will be successful at your company and then design interviews to suss those traits out so you end up making the right hires. You want to bring on missionaries, not mercenaries—people who care about the why more than the what. Those early hires will be your culture and everyone who comes in after them will look to them as models for success. 

What’s the biggest challenge you’ve overcome as a founder so far and how did you do it / what did you learn?

Managing my own psychology. I should start off by clarifying that I’m nowhere near “overcoming” this challenge because I don’t think that’s actually possible—the best I can hope for is to continually make progress. Being an early stage founder and especially CEO is an experience unlike anything else. You feel the highs and lows more than everyone, and it’s impossible to entirely remove your emotions from the journey (nor is that a good thing). The biggest unlock for me was being consciously aware that my emotions were affecting my ability to be a great leader and learning to not live and die with each win or loss. The practice of daily meditation has really helped me establish clearer emotional mindfulness, which has helped me grow my muscles of empathy, both with my own team and with our customers.

What are a few key documents and/or processes you’d suggest founders focus on at early stages? Tips for making them most effective?

Build your operating system and set your operating principles early on. I’m a big believer that people’s actions are the byproducts of their environments. If you want to eat a healthy diet, you can build that habit by removing all the junk food from your home. Likewise, when building a company, you should be intentional early on with the systems you implement. How are goals set, who sets them and how do you hold people accountable to them? How often are meetings and who leads them? What do you want the team to focus on and how do you ensure that they do? If you build the right systems early on, you can engender the right behaviors you want your team to exemplify and thus create the culture you want.

If you want to be fast-moving, tighten your check-in loops and pull in deadlines (e.g. daily standups create faster teams than weekly or biweekly check-ins because you have to show results sooner). If you want accountability, assign DRIs to every project and communicate their ownership to the whole team. If you want the team to prioritize speed over quality, or growth over retention, or whatever X over Y, establish those operating principles clearly so people know what to prioritize. 

What kinds of early hires are most important in this industry? What kinds of characteristics and backgrounds should they have? And how did you approach finding them? 

As I mentioned above, it’s critical that you hire people who care about what the company cares about. If you want a team that has a bias for action, that is scrappy and resourceful, that thinks with first principles, that will run through walls to achieve their need to filter specifically for those types of people. After all, at the end of the day, what you do is who you are. 

As it relates specifically to APIs or fintech companies, I would argue that the character of your early engineers is existentially important. Fintech is a highly regulated market and having builders who understand that and have experience building with those constraints is critical. With a product as technical as ours, it’s also vital that your early tech is not only excellent, but that it’s also designed with a high level of empathy for the customer. We actually interviewed over 80+ engineers before making our first few hires because we found a lot of people who were technically excellent but simply didn’t fulfill the cultural values we were looking for.

What was a key turning point in discovering your product-market fit? What kinds of questions do you suggest fintech founders ask themselves to get here? 

The pursuit of product-market fit is a lot like falling in love. You know it when you have it but it’s hard to truly quantify or measure it accurately. Much like love, you can also lose it despite once having it, so it ends up being an endless pursuit that requires constant hard work. The guiding question we always ask ourselves is: How essential are we to the customer? In other words, could they live without our product? Everything we do is to become more and more essential to our customers, which is best done by solving their great pain points and problems. As long as that’s the north star driving our decision making, we know we will always continue to get closer to perfect PMF.

What tools, resources, and communities should startups in this space know about?

We use Notion as a central wiki for everything. It makes onboarding a breeze and also ensures that anyone in the org can stay abreast of what’s going on across the team without needing to message others. We are also huge fans of Remotion, especially given the transition to remote-first work with COVID. There are endless communities and resources for fintech founders given how hot the space is, I’ve listed a few newsletters below that are good entry points!

Fintech Today - Ian Kar / Julie Verhage

Fintech Takes - Alex Johnson

Fintech Brain Food - Simon Taylor

This Week in Fintech - Nik Milanović

The Business of Fintech - Jason Mikula

The Fintech Blueprint - Lex Sokolin

Continue reading