Caleb Avery | Tilled

April 11, 2023 What I Found

What Is Tilled? Tell Us About Payfac-As-A-Service And Your Overall Mission.

Tilled empowers ISVs to monetize the payments flowing through their platforms with our PayFac-as-a-Service offering. Tilled was the first to offer PayFac-as-a-Service, turning what used to be a line-item cost into a revenue stream. With Tilled, software companies are no longer forced to rely on Stripe, Square, or Braintree for quick processing solutions, or spend the months of time and hundreds of thousands of dollars required by PayFac-in-a-Box providers. Through Modern APIs and SDKs, Tilled's turnkey system allows software companies to be set up and running in a matter of weeks, with no upfront costs or additional headcount required. A company with $100M in annual transaction volume can add $500K in net revenue to their business each year working with Tilled –– that’s what PayFac-as-a-Service is all about.

What Is Your Background? What Led You To Starting Your Own Company, And How Did You End Up In This Space.

I first started working in the payments industry while I was in college, co-founding a credit card processing independent sales organization, or ISO, with a few of my friends. Beginning with very traditional credit card processing customers including restaurants, salons, liquor stores and other brick and mortar businesses, we expanded into processing services for e-commerce businesses and software companies, and now Merchant Services Done Right operates in 22+ states across the country.

Over the years, I also consulted for larger software companies processing anywhere from $100 million to over a billion in annual payments volume. These clients needed a payments expert to help them negotiate agreements, develop new pricing models, and maximize their revenue from credit card processing.

It was while working with these businesses that I had a realization: software companies wanting to optimize their integrated payment processing solution were really looking for two key things. One, an instant digital sign-up experience for their customers. And two, to maximize the revenue they could earn.

I wasn’t able to find a solution that didn’t require my clients to compromise on either technology, user experience, or economics, so I decided to build my own. That’s how I was led to create Tilled and PayFac-as-a-Service.

What Have Been Both Your Favorite And Least-liked Parts Of Your Entrepreneurial Journey? What Have Been Your Most Challenging And Most Exciting Moments For You And The Company?

My favorite parts of my journey have been witnessing the incredible growth of Tilled, and watching the company go from three people all working in our respective basements to now over 50 employees around the country in just a few short years.

At the same time, that level of hyper growth and scale has created challenges that have been some of the less favorite parts of my journey. Every day I’ve strived to evolve and change to meet the needs of our organization, and it pushes me every day to be the best version of myself.

The most exciting moment — so far! — was the day we closed on our $2.15 million Seed round for Tilled. We closed in November of 2020, after a tough year for basically everything. Those were some of my most challenging moments – trying to fundraise during COVID, working from home with two young kids. It was something I hadn’t anticipated. At the time, we had a pitch deck for Tilled, but not much else. We didn’t have a product, or even a website. That round was really just investors betting on me and my vision, and their validation and willingness to come on board meant a lot. It showed they had faith not just in me, but in the vision for Tilled and PayFac-as-a-Service.

Tell Us About What Starting A Business Is Like In Boulder, Colorado. How’s The Startup Scene? Do You Have An Office Or Is The Company Remote?

Our company is remote-first. We do have an office in Boulder, which is an exciting place to start a company. It’s an attractive place for employees to both live and visit. There are so many exciting startups here, and a great scene of local entrepreneurs that were helpful to me early on. But we have also worked hard to build our culture for a remote-first environment, and while that has created challenges, it’s also how we’ve built and scaled since day one. We’ve planned and optimized for it. Recently, we’ve also focused on doing more in-person traveling, getting the team together at different events and opportunities around the country.

What Was The Fundraising Process Like For You? Tell Us About Your Investors And How You Use The Funds You’ve Raised.

When I founded Tilled in 2019, I fully expected to have to travel frequently to New York and Silicon Valley, meet investors in person, and hope the airfare was worth it. Instead, COVID hit, and I sat on Zoom in my basement all day. In many ways it was a good thing, because it allowed me to meet with investors I would have never had the opportunity to speak with otherwise, and I was able to do it much more efficiently. At the same time, there was a lot of hesitancy to invest in anything at the beginning. But, over the past two years, I’m proud we’ve raised $34 million in a variety of market environments, from investors I am happy to have as partners including Canvas Ventures, G Squared, Peterson Ventures, Abstract Ventures, UPC Capital Ventures and more.

How Has Growth Been Over The Last Year? What Does Growth Look Like Over The Next Couple Of Years?

Over the past year, Tilled has grown 30%+ month over month and signed over 80 software companies ranging from startups to publicly traded companies. This next year, we’re hoping to sign 100 more and continue our explosive growth.

Who Are Your Co-Founders Or People Who You Work Very Closely With? How Do Their Skills Supplement Yours?

While I don’t have a co-founder, I’m very proud of the leadership team we have at Tilled. All of their personalities are very different than mine, which I think is unusual for most founders. I took time to recognize what I’m good at and what I’m not, and then found people who could complement those weaknesses and fill in the gaps. It was a very intentional process all the way to find people who could truly help me scale the business, not just people I liked, which I think is a mistake a lot of founders make.

What Was The Inspiration Behind The Company Name?

To be completely honest, it’s very difficult to find a decent URL in the payments space that’s available at a reasonable price. There are so many companies, and so many of them are named pay-something. Personally, I think most of the names are boring. I wanted something that didn’t have “pay” in it, and that had an available URL for a price a brand new startup could afford. I really liked the idea of a till, and was going through iterations of that when I found www.gettilled.com. I got really excited about that, it seemed playful and the price was right. So that was our original URL, and the inspiration behind our name. During COVID, a South Korean payments company that owned www.tilled.com gave up the domain, so we were able to secure that URL for a reasonable price as well.

Tell Us About Your Typical Workday Schedule. What Are Your Morning And Evening Routines? What Are Some Tips You Have For Staying Productive?

With two young children, I’m not sure there’s any such thing as a typical schedule. Every day, I wake up somewhere between 4:30am and 7:00am, whenever the kids decide it’s morning time. I block off time each morning to take my kids to school, and then I’m back at my desk by 9 am and settling in for eight hours of Zoom meetings. When I do go through my inbox, it’s usually early in the morning or at night after the kids are asleep. I couldn’t do any of this without the help of my assistant, Stephanie. She’s my number one productivity tool – and the key to my sanity!

What Are The Top Qualities or Skills You Believe Entrepreneurs Need In Order To Be Successful? Also, What Advice Do You Have For Entrepreneurs Who Are Just Starting Out?

Three skills for entrepreneurs…. sales, sales, and sales? But seriously, sales are that important. I also think it’s important for entrepreneurs to know the importance of content generation and also how to fundraise.

As for advice, I often say the most valuable thing I did when starting Tilled was also simultaneously growing my own personal brand through LinkedIn. I was never a big social media guy, but during the pandemic I made an effort to build my presence on LinkedIn and connected with anyone and everyone I could in the payments industry. Eventually I moved from engaging and connecting with others to posting my own thoughts and ideas. Today it is still a big driver of leads into Tilled and accelerates our sales process. I can’t emphasize enough how important and worthwhile it has been.

Tell Us A Story Of Something That Happened To You That Taught You An Important Lesson.

I think one thing that has been surprising and certainly taught me the importance of building my own personal brand is when I get on the phone (or Zoom!) with customers, potential partners, investors, or anyone really and realize how much they already know about me from following me on LinkedIn. Right off the bat they’ll ask me detailed questions about my family or my life outside work, and it’s taught me the value of authenticity and how memorable it can be for people to get to know me beyond just being the CEO of Tilled. For anyone who hasn’t experienced that, it’s hard to quantify the impact. But it’s impossible to understate how valuable it’s been for me and for Tilled, and how it makes an impact every single day.

If You Can Have A One-Hour Meeting With Someone Famous Who Is Alive, Who Would It Be And Why?

Even though I consider them direct competitors, and the meeting might come to an abrupt end when one or all of us walk out, I’d be very interested in a conversation with the Collision Brothers who founded Stripe. If we could get past our differences in opinion about how embedded payments should work, I think we could have a very interesting conversation about the future of payments and how our industry can have a positive impact moving forward.

What Do You Do In Your Free Time?

To be honest, I don’t have a lot of it. But I do enjoy golfing and skiing when I can, and I recently bought a golf simulator for my garage. I also consider myself a bit of a pool shark, and have a pool table in my basement you can find me at every so often. I definitely aspire to do more, but with kids and a business it can be difficult. I really enjoy spending time with my kids, they are absolutely my priority.

What Are Some Things You Incorporate Into Your Schedule To Maintain Health And Wellness?

I still have blocks on my calendar to go to the gym, see a chiropractor, and I also enjoy cryotherapy. I don’t have a ton of time, but I have built them into my daily routine. As far as eating healthy, I’ve found that Uber Eats delivery of healthy food is key. I also spend a lot of time with my kids, and they keep me active and outside chasing them around.

What Does Success Mean To You?

To me, success looks like revolutionizing the payments industry for the better. There are too many companies out there that operate in darkness and play games with their customers, and unfortunately they’ve gotten away with it for far too long. At Tilled, we not only have a revolutionary product with PayFac-as-a-Service, but we offer it in a revolutionary way – transparently, with honesty and integrity towards all of our stakeholders. In my opinion, we can’t have success in one area without the other.