21 fintech founders their accomplishments, challenges, excitement, & predictions


Stephany Kirkpatrick : Founder & CEO of Orum, infrastructure to enable enterprises to offer automated, real-time money movement. Distributed & founded in 2019.

Anthony Strike : Founder & CEO of SteadiPay, a bank-agnostic platform that helps SMBs manage cash flows and generate higher returns. Based in LA & founded in 2017.

Gil Akos : Cofounder & CEO of Astra, a platform for money movement, turning programmatic bank transfers into an API. Based in Menlo Park & founded in 2016.

Nami Baral : Founder & CEO of Harvest Platform, a startup that helps average Americans reduce debt and build wealth. Based in NY & founded in 2018.

Ansel Parikh : Co-Founder of Finch, an API that allows applications to access data and make changes across payroll & HR systems. Based in SF & founded in 2020.

Danielle Pensack - Cofounder & CEO of Rightfoot, an API to embed student debt repayment and other debt repayments into products. Based in SF & founded in 2018.

Hooman Radfar - Cofounder & CEO Collective, the first online back-office designed to support businesses-of-one. Based in SF & founded in 2019.

Ian Mendiola : Cofounder of Doji, an app that searches the stock market for the best options to buy and sell. Based in NYC & founded in 2019.

Rachel Carpenter : Founder & CEO of Intrinio, a financial data partner that delivers high-quality data for developers. Based in St. Petersburg & founded in 2012.

Matt Wensing : Founder & CEO of Summit, a new language for financial modeling designed to replace modeling in spreadsheets. Based in Austin & founded in 2019.

Katie English : Cofounder & CMO at Harness Wealth, a startup that’s creating the next generation wealth management for builders. Based in NY and founded in 2018.

Naftali Harris : Cofounder & CEO of SentiLink, a company building technology to end identity fraud. Based in SF & founded 2017.

Rebecca Liebman : Cofounder & CEO of LearnLux, a workplace financial wellbeing platform. Based in Boston & founded in 2015.

Neel Ganu : Founder & CEO of Finch, an all-in-one account that gives you the power of investing with the flexibility of checking. Based in NY & founded in 2019.

Jessica Willis : Founder & CEO of Pocketnest, a platform for financial panning for millennials and gen-xers. Based in Ann Arbor & founded in 2017.

Bobby Matson : Founder & CEO of Payitoff, a student loan middleware that helps companies help their customers pay off debt. Based in NYC & founded in 2017.

Mitchel Scott : Cofounder & CEO at Modern Logic, a no-code rules engine to make smart decisions about compliance and fraud. Based in Berkeley & founded in 2020.

Christie Horvath : Founder & CEO of Wagmo, a pet insurance company with easy-to-understand plans and fast claims processing. Based in NYC & founded in 2017.

Travis Hedge : Cofounder of Vouch, an insurer for protecting high-growth tech companies from litigation and theft. Based in SF & Chicago & founded in 2018.

Clayton Gardner : Cofounder & Co-CEO of Titan, a mobile direct-to-consumer platform for active investment management. Based in NYC & founded in 2018.

David McDonough : Founder & CEO of Commonstock, a social investing platform for signal over noise. Based in SF & founded in 2016.

What has been your proudest accomplishment in 2020?

Stephany at Orum : I’m most proud of building & launching the first of its kind pre-authorization for ACH transactions. In less than 6 months, we have made meaningful traction with live partners in a closed beta. Seeing partners use our Foresight product to unlock instant ACH for upwards of 85% of their customers is amazing.

Nami at Harvest : Our proudest accomplishment was our ability to generate millions of dollars in refunds to our customers who needed it most. In many instances, our refunds amounted to a second stimulus check for consumers this year. These refunds helped everyday Americans put food on the table, supplemented a loss of income, and even helped some avoid eviction. We saw an 18X increase over last year’s amounts.

Gil at Astra : We are most proud of our team’s execution in 2020, specifically for our transfer orchestration technology and our API. ACH transfers have a high failure rate natively, yet we’ve achieved a 99.999% reliability rate for transfers landing as expected. We also launched our external API in just 6 weeks – the team built a developer sandbox, dashboard, documentation, and OAuth application at a spectacular pace!

Hooman at Collective : In the early months of the pandemic, the tax deadlines moved twice, a number of new government programs launched, and our customers’ future revenue was uncertain. For those members that were hardest hit, we credited their accounts with 2-3 months of free service so they didn’t have to worry about costs. It was awesome to see our team pull together and to see how our community benefited.

Ian at Doji : I'm really proud that we launched the product. Building a trading platform is not easy. There's a lot of complexity involved with trading securities (especially options), and it's a highly regulated environment. If something goes wrong, the consequences are much higher. You can't really have a "move fast and break things" or "ask for forgiveness, not permission" mentality in consumer finance.

Naftali at SentiLink : We passed 100 million identity verifications this year. These are credit card applications, bank account creations, new membership applications, auto loans, and ID verifications in other contexts where we’ve been able to protect our financial institution partners from fraud and help to identify their customers. I’m so proud of our team for being able to achieve this only 3.5 years into our company history!

Rebecca at LearnLux : Our proudest accomplishment was being able to support essential workers by providing financial wellbeing benefits to some of the top employers in the country. Some employees worked at a desk, many worked at construction sites, and all needed trustworthy guidance to get through the hardships.

Jessica at Pocketnest : We're wrapping up 2020 with 9 enterprise customers, an average of 20 percent monthly user growth, and 34 percent monthly increase in app engagement. We're proud of our team for how quickly we've grown since our Oct. 2019 launch.

Matt at Summit : We realized in January that our first product wasn’t what the market wanted. We spent March through May rebuilding it from scratch, and launched in July. We’ll be celebrating that into the new year, then get back to work!

Christie at Wagmo : In 2020, we managed to secure our insurance partner, revamp our UI/UX to accommodate insurance, and launch our new pet insurance product in our key states. We also doubled the team and put in place some new distribution partnerships.

Neel at Finch : I’m really proud of my team for bringing Finch to the market this year. We started the year with a bold vision and a prototype. We were able to navigate the challenges of developing our platform, while transitioning to remote work and transforming our brand (from Trio to Finch). I’m proud of our agility and persistence.

Mitchel at Modern Logic : We went from idea, to prototype, to seeing customer live on our platform in 2020. Watching how our first customer wanted to add new rule types and new logic, beyond what we’d considered previously – and how our rules engine was able to extend seamlessly to meet their needs – made us proud of what we’ve built so far.

Travis at Vouch : I couldn’t be more proud of how our team has come together this year. Teams either grow stronger or falter through adversity, and ours has grown stronger. We’ve more than doubled our team, grown the business faster than expected, maintained a 90 NPS along with high team satisfaction.

Clayton at Titan : I’m proudest of our success in keeping consumers invested through the vicious COVID-induced market drawdown and also changing their financial behavior for the better. We’ve delivered nearly $100 million in net gains to date and grown user engagement & retention to levels approaching best-in-class social network.

David at Commonstock : One of our users served in the Air Force & was laid off this year. He built an audience sharing his knowledge & now has over $50M following him on Commonstock. It’s opened multiple doors to jobs & has helped support his family. These types of stories keep us excited to create this new platform.

What are you most excited about on 2021 roadmap?

Ansel at Finch API : We have some major integrations on the roadmap that can open up access to millions of US employers for our developers. As we expand, we've discovered new use cases from immigration workflows to commuter benefits. There's a lot of work to do but we're seeing a whole new opportunity set heading into 2021.

Anthony at Steadipay : There’s a big gap between all the new finance platforms and the vast majority of small businesses. We’ve launched a dashboard for cash & bank-agnostic treasury services. In 2021, we will evolve into a “controller-as-a-service” with deeper insights into financial needs + a broader network of services to meet those needs.

Danielle at Rightfoot : I’m extremely excited about launching our self-service developer portal in 2021. As our Director of Engineering Will likes to tell me, “developers don’t want to chat with you, Dani!” We now enable anyone to sign up and get production keys! Our designers have done an awesome job of keeping things sleek and simple.

Rachel at Itrinio : Our financial data feeds are quantitative in nature (we sell stock prices, financial statement data, earnings estimates, and more). We’re adding qualitative data feeds in 2021. You can query our API and ask “what is Apple’s stock price” but you will soon be able to ask “how is Apple handling the COVID pandemic?”.

Katie at Harness Wealth : In early 2021, we are launching a new tool that helps our customers see their equity holdings over time as part of their larger financial picture. It will provide personalized insights on decision-making. Think of it as Personal Capital meets Carta! We have some new Employer partnerships lined up to kick off next year!

Bobby at Payitoff: In 2021, there will be a “student loan cliff” when repayments resume and ~ 24 million borrowers will be looking for assistance. The government has a program called income-driven repayment but it takes hours of research & paperwork to enroll. I’m most proud of how we have built the first, automated enrollment. Our Partners will be able to help millions manage income-driven repayment plans.

What’s something you have changed your mind on ?

Stephany at Orum : When I launched Orum, I knew that there was a major opportunity to drive meaningful change through infrastructure innovation the would enable instant & risk-mitigated money movement at scale. However, as we’ve spoken to customers, we’re seeing just how broad & acute their pain points are. Our team is committed to building products that enable the change the industry is looking for.

Anthony at Steadipay : I thought we needed to build the most accurate cash forecast for SMBs. The product ends up needing all sorts of inputs. A customer said: “Once I build the forecast, I now know my cash flow & will run the business differently...which immediately makes my forecast obsolete.” 99% accuracy was NOT the job-to-be-done. A tool that requires little or no inputs would be significantly more valuable.

Nami at Harvest : We always knew that high-interest bank fees are a hindrance to the average American’s mobility. In 2020, we realized that access to credit also needs to be democratized. We launched our own health score & ramped up efforts to improve credit & cash flow health. It has paid dividends - with increased customer loyalty and revenue.

Gil at Astra : Success is defined by how well you handle edge cases. How your technology responds to moving money outside of the median scenario can result in orders of magnitude difference for the performance of an infrastructure product. This is not sexy work but makes the difference between scalability and liability. Platforms that optimize for the edge cases are hard to build, but also represent the largest opportunity.

Matt at Summit : We originally built a forecasting engine. Users could enter their own inputs, but the model itself was fixed. We changed our minds when we heard how much flexibility users need to define their models in Summit. This required a much higher level of abstraction, such that the model itself could be designed & built by the user.

Ansel at Finch API : Through dozens of developer calls, we identified a single thread that was valuable across multiple use cases : the employee directory. In order to cater to a wide range of developers, whenever we launch new products, we tie them back to the directory to ensure those endpoints build upon the foundation of that base dataset.

Danielle at Rightfoot : It’s less about changing our minds and more about listening. We look to the market to tell us what we should or should not be building. Four out of five of our clients ask us to build APIs for auto loan repayment, mortgage repayment, medical debt repayment. We’ve now moved up debt verticals on our roadmap.

Ian at Doji : Initially, we abstracted away all the details of options and how to trade them and made it really simple to make a binary bets. We realized that users needed to understand what's happening behind the scenes to feel comfortable. Since then, we've exposed underlying details of options trading & have focused on options education.

Rachel at Itrinio : Our team sold a multitude of 3rd party data alongside our own. Data marketplaces have become commoditized in the past few years. We wanted to build valuable data sets and we needed to get back to our core competencies. This increased focus led to product advancements, happy customers, and rapid growth for us.

Naftali at SentiLink : Remote work has been surprisingly successful for us so far. Despite not being able to go into the office, we’ve been extremely productive, communicated well, and had an unbelievable 2020 on both product and business development. As a result, we’ve moved to a more remote-friendly working policy.

Rebecca at LearnLux : Financial planning is a mix of math & emotion - there’s a big element of planning that has to do with how people feel about money and financial decisions. That has to be incorporated into a product experience.

Katie at Harness Wealth : We believed our solution made sense for a wide range of individuals, but quickly found that going after what we call builders - individuals founding, scaling & investing in tech companies - was going to be the most effective starting point. They need access to better tax & financial planning advice. Since they are networked early adopters, we knew we will get strong brand awareness & referrals.

Bobby at Payitoff : As a CEO pre-2020, I felt that landing on every grenade was important and being the shield to market chaos for the team was crucial. I’ve changed my tune on this since COVID-19 began and feel self-care is critical. Leadership’s mental health, physical well-being and attitude are fundamental to the success of the company.

Mitchel at Modern Logic : We were initially focused exclusively on our core rules engine product – making it as intuitive as possible to help create & edit the logic. But our conversations with many risk leaders helped expand our focus to include the analytics layer of how that logic is performing, and what’s causing manual work for their teams. Analytics wasn’t a feature set we could bolt-on years into the future.

Travis at Vouch : I thought we would hire startup sales people and train them up on insurance, because we didn’t want to carry over the baggage from how things are done in legacy insurance. While half of our customers self-serve, the other half want to get on Zoom with an Insurance Advisor. We’ve found that startups would rather work with an insurance expert that happens to speak startup.

What is underestimated or misunderstood?

Danielle at Rightfoot : A lot of people think that paying someone’s student loan is as simple as sending money to a bank account. Student loans aren’t routable accounts like bank accounts. When an employer looks to make payments to their employees’ student loans, they often send checks to the servicers & cannot target employee’s highest interest loans. The fragmented market of student loan servicers have backends built on COBOL in the 1970s. Building & managing integrations to make payments is costly.

Hooman at Collective : Businesses-of-one benefit tremendously from an S-corp tax election if they’re making $60-70K or more in income annually. A common misconception is that realizing tax savings is as simple as setting up an S-corp. In reality, you need to run a proper back-office - banking, payroll & more to minimize FISA tax within the IRS guidelines. You can work with a company like Collective, or you can string together a solution with a lawyer, accountant, and other vendors.

Ian at Doji :Most people think the trading segment has already been won. Access is easier than ever because of mobile apps, zero commission, social, and fractional shares, but there's still a huge knowledge gap of how & what to trade & invest in. We think there's a lot of room to come up with a fundamentally different experience that makes it even easier for people to participate in the markets.

Matt at Summit : “Replacing Excel” is the siren song. We think this is because most companies attempt to treat Excel as an app, and therefore they try to replace it with their own app. We believe spreadsheets are a language, and the only way to replace Excel is to develop a new and better language. That is why our product is a development environment, not a set of charts or tables of financial data.

Naftali at SentiLink : The role of human insights in understanding fraud & identity is underestimated. “Big data” & “machine learning” have become buzzwords, but many companies in our space that use these terms quite frankly don’t even understand what they mean. We have a team of analysts reviewing cases & the whole company spends an afternoon investigating fraud together once a quarter.

Rebecca at LearnLux : It’s a major misconception that financial planning is only for the wealthiest Americans. Whether an employee is tackling credit card debt, building up savings, or investing in the stock market, they need a plan. The harsh reality is that the majority of employees lack a plan - and they don’t have the resources to create one.

Christie at Wagmo : People tend to reduce the challenges in pet insurance to lack of consumer education & customer acquisition. As a regulated industry, most companies partner with established companies on the underwriting, claims administration, and customer support. Not only do you have to acquire the customer, but you have to figure out how to service and keep that customer without full control over the experience.

Neel at Finch : The common wisdom is people don’t invest because it’s complicated. We have learned through research and by speaking to hundreds of potential users that people have the fear they won’t have access to their money when & where they need it. To avoid their money being locked away, people resort to what they’re comfortable with - checking and savings, which do not help them accumulate wealth.

Mitchel at Modern Logic : Recently, the emphasis in risk tools has been all about machine learning. But if you look at fintech companies getting started today – they have no historical data to train models on, and they need to explain their decisions to bank partners, regulators, and even customers. There is a tremendous opportunity to build rule-based, explainable, transparent decision systems for fintech companies.

Jessica at Pocketnest : I don't think people realize just how scattered an average person’s financial plans are, and how big of an opportunity they present. While 90 percent of millennials feel overwhelmed by their finances, most of them go to Facebook and Twitter for guidance. They are desperate for financial support, but their financial institutions simply don't have the technology or approach to properly meet their needs.

Clayton at Titan : Many love to point to the decades-long shift to index funds & claim that “active is dead” -- that no one can do better than average. We think this is a condescending take that misunderstands why consumers are flocking to stock trading. The desire to actively participate in markets has been evident in the spice trade several millennia ago, to whale hunting in 900 AD, to stock trading in Big Tech today.

David at Commonstock : Popular narrative about self-directed investors underestimates the reality. Majority of investors are responsible people, often with some experience, looking to improve their financial health. There’s a small but vocal minority who treat markets like a casino & get disproportionate airtime. Long term value accretes to products that optimize for expertise over entertainment.

What would be more prevalent by the end of 2021 ?

Stephany at Orum : I think we will see more progress towards fully automated money movement innovation where financial outcomes are supported by dynamic and smart infrastructure. More and more we are going to see services that calibrate toward daily liquidity and payment cycles versus monthly or longer--and where more Americans are able to do more with their money because it is automated and instant.

Anthony at Steadipay : I don’t want to bring all the crypto people to the yard, but...Crypto has gotten renewed love this year as an alternative to fiat currency, but blockchain tech seems to have lagged. I think we’ll start to see the smart contract side of things come out of its winter.

Nami at Harvest : We will see a broader commoditization of products that were reserved for higher net worth individuals, and more products will be built for average Americans. We’ll see an aggressive bundling of products. Customers will start to reject the concept of a bank as the only choice to provide financial services and will increasingly ask “How is my financial health?”.

Gil at Astra : Fintech APIs will continue to modernize an expanding set of singular modules within the banking stack, but horizontal platforms will emerge & start to grow even more rapidly. Platforms take more time to grow & need some mechanism to bootstrap scalability but outperform in the long run. Serving your customers’ customers & platforms of platforms will be next year’s mantra.

Ansel at Finch API : The impact of pandemic has forced many SMBs to adopt fintech solutions in an effort to stretch what little resources they had. We believe that this rapid shift can accelerate the SMB recovery & that SMB fintech is on the verge of a renaissance. We're already starting to see platforms that unlock government grants, forecast headcount, and open up access to alternative financing.

Rachel at Itrinio : Fintech has been responsible for great strides in payments, lending, AML, KYC, and consumer banking over the past decade. That’s old news. The larger opportunities, albeit less sexy and understood by the general public, lie in the guts of the financial services industry. Moving under the radar, and quite literally under the hood, I’m excited to see those advancements play out.

Bobby at Payitoff : I think we’re going to see API companies shiftly to an “abstraction layer” rather than focusing on use cases alone. There has been a lot of buzz about APIs but the reality is most companies don’t have the time or resources to “build from scratch” and keep re-inventing the wheel on single use cases. They want something higher level that is the default & have option to dive deep into the data & domain.

Travis at Vouch : I think Fintech is about to get unsexy because the shift to remote is exposing founders to different problems & talent. For example, I’m a big believer in emerging markets like Columbus where companies like Root & Olive have been able to blend local industry expertise with technologists. I think the conversation will be less about APIs & more about solving huge unsexy problems with full-stack solutions.

What has been your team’s biggest challenge ?

Hooman at Collective : The challenge with all-in-one solution value proposition is understanding how to best prioritize product development. The best idea we’ve had so far to tackle this is simple - we get feedback from customers in every way. I call members that gave us the lowest NPS to see how we can improve. We make consistent effort to get closer to them so we can build what they need, not what we want.

Jessica at Pocketnest : Our biggest challenge has been what we call the "three-legged stool"of launching. To secure more customers, we need to demonstrate how our product is growing; in order to demonstrate growth, we need budget for marketing & development; to build the product & afford marketing, we must raise more capital. To overcome this challenge, we've operated by a scrappy, quick-to-pivot approach.

Christie at Wagmo : The biggest challenge has been building out the team this year. I think founders take for granted the role that in-office communication plays in enforcing team dynamics, particularly in the earliest days. This year made us re-think everything from how we bond to measure performance. We’ve managed to onboard new teammates and pay particularly acute attention to the personalities we bring around the table.

Katie at Harness Wealth : Our biggest challenge has been hiring virtually during COVID & integrating new team members into our existing team culture. One idea that worked really well for us is hosting virtual game-nights and having 1:1 weekly virtual coffee chats via Donut. It was a nice way for the team to get to know one another better.

Neel at Finch : Our biggest challenge has been helping customers decide which silo of checking, savings, or brokerage account we fit into - as we redefine how you can manage your money. To tackle this, we will lead heavily with education and work with users to understand where the lines get blurred between banking & investing and how we can enhance the user experience to clearly bring our value to life in the app.

Clayton at Titan : User acquisition challenge has been our biggest focus, and fortunately we’ve begun to make huge strides here. Our secret sauce is content. Charlie Munger once described Disney as an oil company that can drill oil and then put it back in the ground to re-drill again. The market creates stories for companies every day. Our job is to refine this “oil” into top-of-funnel content that delights consumers & creates moments worth sharing via word-of-mouth and referrals.

David at Commonstock : The biggest challenge is finding a scalable way to incentivize and reward quality. Our crazy idea is to weight traditional “follow” & “like” counts based on the portfolio attached. To build a valuable following, users must share smart content, not noise. This has turned “Follower Value” into a status symbol.

Big thanks to every single person who participated and helped make intros! Part one can be found here.