Faces of Entrepreneurship: Wayne Chang & Jeff Seibert, Digits

Wayne Chang and Jeff Seibert are the co-founders of Digits, a fintech company on a mission to revolutionize the way small businesses manage their finances. After co-founding Crashlytics (sold to Twitter in 2013, then to Google in 2017), they set out to solve an issue they faced as entrepreneurs. Using an AI-generated dashboard, Digits has built a real-time finance engine giving founders and operators a full understanding of their business, as it happens.


What does “entrepreneurship” mean to you?
Wayne Chang and Jeff Seibert: Entrepreneurs always start with a vision for something: to build a new tool, reimagine a process, or even just bring a new perspective to an existing market. But it takes more than vision. A lot of people have great ideas, but entrepreneurs are the ones dedicated to making an idea into something real and are willing to sacrifice everything to see that vision through. It can be ruthlessly uncomfortable, but it’s also incredibly thrilling and fulfilling to build things that have never existed before. Riding ideas, following them where they take you, and pulling actual products out of the ether.

How did your company come to be?
WC & JS: We actually built a prior company together—Crashlytics (which runs on over 5 billion phones worldwide!) — But as we were building the company, we constantly ran into money questions, and we couldn’t get the answers fast enough. Either because we didn’t receive financial reports until our books were closed, or because the information we needed was scattered across several systems. As the company got bigger, these issues became even more pronounced.

We knew our next company had to focus on solving those problems, not just for us but for every entrepreneur struggling with the same challenges. Freeing them up to concentrate on what they do best is a long tail that pays off big. They didn’t get into business to wade through the swamp of numbers and financial data! They want to build, which involves knowing the numbers, but in a more nimble way than a typical report. From our own founder experience, curiosity about the financials always arises from a decision-making outlook.

If we can empower founders and small business owners with confidence in their numbers, that knocks over one helluva domino. Suddenly they have complete clarity of their money situation moment-to-moment. And we’ve built a tool that’s easy to set up, works in real-time, and delivers killer insights! As business owners ourselves, it feels almost overpowered to be able to understand our numbers without translation from our accountant. Now we just ask Digits.

How has your business changed in response to the COVID-19 pandemic?
WC & JS: Digits was founded as a remote company in 2018. So we were already working remotely from home. But when COVID hit, we knew other companies weren’t as prepared, so we supported them by releasing a guide for remote work that shared our learnings from the last 2+ years and gave companies a tool to help manage expenses.

Our how-to guide for remote work shares the key things we’ve learned building Digits that helped us not just work remotely but build an awesome, productive and inclusive culture from day one. We’ve heard from so many companies, both large and small, that have used this guide to establish their own remote work policies.

When the pandemic first hit, we were still in stealth mode so we didn’t have a product available for companies. But looking at the impact of the closures, rising PPE costs, and more were having on businesses, we quickly spun out a version of one of our products to help manage expenses. It provided some much-needed visibility to those companies at a time when they really needed it, and we continue to work with those companies today.

One of those customers is a surgeon who now uses Digits to track expenses. Last March, when the prices for PPE were skyrocketing, his team kept buying at their regular pace. The surgeon didn’t know this until his end of month report came back in mid-April and it almost put the practice out of business!

What is your proudest and darkest moment so far?
WC & JS: We are the proudest of our team. As founders, our goal isn’t to just build great products, but to build great teams that then build great products. A big part of that is making sure that everyone we work with feels valued, supported and trusted to do their best work. So seeing our team succeed in their roles at the company brings us a lot of pride. Many of the people who were with us at Crashlytics have continued to work with us for over ten years and are now at Digits, which is a huge honor.

In terms of low points, the journey has been long. We knew going in that it would be because we were taking on something no one else in the industry has even dared to try. But even so, solving it took longer than we thought. The good news is that now that we are on the other side of that chasm and we know we have an advantage over anyone trying to enter the space.

How is your company changing the landscape?
WC & JS: Our investors, our board, our customers all believe that Digits is creating a paradigm shift in the way that businesses manage their finances. Most entrepreneurs today have no background in finance or accounting. They didn’t start their company to “run a business.” They started it to offer a skilled service, build a product they love, or serve their communities.

The problem is that the tools available today make it incredibly difficult to get a full picture of your business from a financial perspective. You can see pieces in your bank account or credit card statements, but it’s been impossible for an owner to quickly access information from all of those sources (plus the ledger, payroll, etc.) in one clear picture.

Digits provides the equivalent of an MRI machine in a world that has only seen partial x-rays. Like an MRI that allows doctors to see various parts of the body and how they interact with each other. Digits put an entire business at an owner’s fingertips, in real time.

What advice/credo do you live by as you grow the business / what is your professional and personal mission statement?
WC & JS: Remember that there is a person on the other side of the screen that, in the busy world they’re in, is now about to use our product. What kind of delightful, fun, immersive experience do we want to craft for them? That question drives all of us and is imbued into the products we build. The human experience is our north star, and filters down into everything else we do. As an example of that philosophy in action, we spent a lot of time designing the onboarding process for customers. Our industry’s track record with onboarding is abysmal. It’s gotten so bad that there are entire professions dedicated to onboarding, complete with on-premise set up and training – that you pay for! What a terrible first impression and experience.

We spent incredible amounts of time, energy, and focus to refine our onboarding – an industry first for the type of software we’re building. No. Setup. Required.

Where do you find inspiration when faced with challenges?
WC & JS: We find inspiration from our broader team. Our goal as founders isn’t just to build great products but to build a world-class team that can build great products. We have a high bar in terms of the talent we work with – the team we have is incredibly passionate about our customers, deep domain experts in their respective fields, and laser-focused on the mission we’re all on. We feel lucky to be able to turn to our amazing, experienced team when challenges come up. The team doesn’t shy away from challenges – the tougher the better!

What’s it like to work alone or with your partners? What advice do you have for fellow entrepreneurs about building and leading teams?
WC & JS: With Digits being fully remote from day one, we’ve mastered a different way of working. Working remotely is fantastic, but it can also become lonely or isolating. So we deploy a working style at Digits that we call the Buddy System. It starts with the employee onboarding process, where we pair new team members with an existing one and it extends into all of the work we do, even our relationship as co-founders. The Buddy System has worked incredibly well and reduces the feeling of isolation and increases the feeling of working together.

We also believe in finding ways to connect groups beyond their day-to-day work. Those layers of connection build trust and strengthen teams. We typically all get together in person a few times a year. Because of COVID, that hasn’t been possible, but this summer, we decided to bring vaccinated team members together regionally for a series of IRL get-togethers.

We care about promoting social bonding especially in a remote working culture — we’ve made it a company policy that whenever three or more team members get together, the company will sponsor it!

Many entrepreneurs continue to perfect their daily routines to support their work and greater vision; would you mind sharing your morning routine or a regular ritual that grounds your work each day?
WC & JS: We both wake up early to get a jumpstart on the day, often even before our East Coast team is online. Outside of that, we don’t have a set schedule, but work to keep our calendars open and free of meetings so that we are available to answer questions and collaborate with our team as needed. That way we can jump in and speed-boost our team when they need it rather than them having to wait to get on my schedule.

Who are the people who have mentored or influenced you in your life or career? How has their influence changed the trajectory of your entrepreneurial journey?
WC: Growing up, I didn’t have a lot of role models or mentors to look up to. But I had a sense of what was out there in the world, so I sought it out in books. Growing up I read everything I could get my hands on about business, entrepreneurship, investment, profiles of industry titans I admired. It’s great to have mentors if you have them available to you, but if you don’t, a library card opens up a lot of opportunities. This approach gave me the opportunity to learn the ropes directly from the greats — the best of investing from Buffett, the way to build products from Jobs, the creativity from Disney. But, nothing teaches like actual experience, so putting all that into practice through many different startups and fine-tuning what delights customers, what makes a great product great, making startups into rocket ships and touching billions of people daily, has led up to our most impactful project: Digits.

JS: Growing up, I read a lot about Steve Jobs and was deeply inspired by Apple’s story, challenges, and opportunity for rebirth with the launch of the G3 iMac. Steve’s focused obsession on the user experience and his unwillingness to compromise or settle for anything less than what he viewed as “insanely great” was empowering. Of course, simultaneously he was over-lauded in the press and inaccurately idolized. I was fortunate enough to land a college internship at Apple and see the pros and cons of his approach first-hand, even (briefly) meeting him in person. This was eye-opening — and has shaped how I aim to build companies to this day with a deep focus on customer experience and product quality, while maintaining the importance of work-life balance and tight-knit team collaboration.

Do you have someone you’d like to nominate to be profiled in our Faces of Entrepreneurship series? Please let us know by emailing media@thecenter.nasdaq.org.

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