The Startup Mentality: Knocking on the Doors of 100-Million-Dollar Software Companies

Caleb Avery is the CEO and founder of Tilled, a 4-year-old payments company known for coining the term “PayFac-as-a-Service”. Tilled brings a unique offering to the payments space, empowering software companies to enjoy the benefits of being a PayFac without the upfront investment or ongoing overhead. While the PayFac industry is full of complexity and nuance, Tilled’s unique approach provides their partners with a white label, turn-key process for seamlessly entering the PayFac space.


Caleb Avery is the CEO and founder of Tilled, a 4-year-old payments company known for coining the term “PayFac-as-a-Service”. Tilled brings a unique offering to the payments space, empowering software companies to enjoy the benefits of being a PayFac without the upfront investment or ongoing overhead. While the PayFac industry is full of complexity and nuance, Tilled’s unique approach provides their partners with a white label, turn-key process for seamlessly entering the PayFac space. Prior to the launch of Tilled, a company could expect the PayFac onboarding process to span six to nine months. With Tilled, this process has been streamlined and shortened to mere weeks for better offerings and flexibility to merchant bases.

Innovation Begins with Vision, and Asking the Right Questions

“I think people can be scared to ask themselves, is this actually a business that’s worth building?”

The entrepreneur’s life overflows with tasks, ideas, and vaguely connected responsibilities and roles often spanning from the copywriter to the technologist steering the build of a new product. Lists like these can grow quickly and distract any business founder from the important foundational choices they need to make.

In Episode 2 of SeerCast, Adwait and Caleb consider together the influences that have led to their choices and the questions they faced along the way.

Founders often must start with the questions,
“Do I have the energy and commitment to go build this business?”
“Am I willing to take the personal risks in the investment?”

The more important question however is,
“Is the business actually worth building?”

Caleb Avery couldn’t answer the question from his own intuition or reflection, but only through his own action. Tilled started with on-the-ground customer discovery. Caleb asked potential stakeholders directly, is this something the industry needs? is this a solution you would pursue? After these questions are answered, a founder can move in a direction with confidence and focus on the ground-level work needed to build out their vision.

 

Defining the Mission and Strengthening Vision

“Here’s our flag, this is where we fit into the ecosystem. Once that was clear to folks, the ISV and software companies knew exactly what the value prop was.”

Tilled’s success started with planning and messaging. As conversations with potential customers continued, the demand for their product became even more clear. Businesses consistently lamented the drawn out and complicated process of entering the payment facilitator space. When a solution like Tilled, based on simplicity, was brought to the table, it solidified the confidence to actually pursue the business. With each step in the founding, Tilled planted its flag deeper into the market.

Like most other startups, Tilled approached the next important question,
“How do we get funding?”

Talking to Investors and Being Comfortable in the World of Rejection

“There’s plenty of articles out there saying you have to get warm introductions to VC’s but you don’t have to. Pre-seed round started with cold emails to investors.”

Tilled sought initial funding much differently than most startups. Even with excited potential clients, venture capitalists weren’t lined up waiting to invest in Tilled. Unlike many well-connected entrepreneurs, Caleb didn’t have numerous contacts of angel investors or firms who were willing to take a risk based on their past relationship. Instead, the approach was cold emailing.

While plenty of people use cold-calling as a numbers-driven approach where the length of the recipient list dictates the success of the campaign, Caleb didn’t deviate from the strategic and detailed approach he had used from the beginning. Instead of blasting an email to every firm they could find information on, Caleb delved into the research to determine the firms who would be most interested in Tilled’s value proposition. He looked for investors that appreciated the industry, appreciated the stage of the company, and understood the space that Tilled was trying to enter. His message carefully explained his background, his vision for the product, why that specific firm was a good fit for the particular round of funding. The time and energy Calen invested was clear to the reader, and it established him further as a founder with a vision.

Another small yet important element of investor interactions was the upsell. As each conversation closed, whether with a deal or without, Caleb would ask, “Is there someone else that I should be talking to about this round.” Through this, he learned that while plenty of firms may not be interested in a specific product at a particular time, they are often happy to pass on half a dozen other beneficial contacts. The first firm may not be the right fit, but they know the benefits of starting a relationship and returning some value. Caleb knew too that when Tilled was ready for that Series A or future round of investing, he could look back to the firms with a relationship already in place.

Building a Team Through Values and a Mission

“Are they aligned on the mission? Do they share the values of the organization? Do they actually have a passion for the problem?”

The common depiction of a “successful team” is of a highly experienced individuals with different skill sets all performing unique functions. They usually have many years of technical training and offer insights only a seasoned veteran of an industry would be able to acquire. Adwait Joshi and Caleb Avery both challenged this paradigm with their startups. Early on, Caleb

Caleb recalled asking early team members, “Why are we going to win against Stripe?” The responses to this question were not all technical, and when he went deeper into those conversations, the passion and fire to pursue that mission was what stood out. Adwait agreed, “You can teach technology, you can teach payments, you can teach programming, but you can’t really teach passion. You either have it or you don’t.”

The Life of an Entrepreneur and Founder

“I’ve carved out my Tilled time, I’ve carved out my time with the kids, how much is actually left over for me to focus on myself?”

Of course, it is no surprise that all startup founders lack one thing: Time. Especially in the early stages, and often throughout the life cycle of a company, founders are the last line of defense for a number of issues. CEO’s must learn to focus on balance and time management. Caleb has a direct answer to these problems…

“For me, I had a couple of things that I just said, these are non-negotiable. I am going to take my kids to school every day… I try to be home to put them to bed, which can mean limiting traveling and late-night events. And so, it’s setting those boundaries.”

The process of balance doesn’t have to originate from some high-level philosophy, rather it’s in successfully managing the time you are given each day – some days you will be more successful with balance, and some days it will feel like nothing is working.

Taking the Leap

Founding a business is a daunting task, filled with pitfalls, exhaustion and stress. The feelings of uncomfortability and unknowingness can sink even the most well-built ships. The desire to handle all the details and check all the boxes before taking those first steps forward can paralyze a truly valuable idea.

There is always value to be found, despite the uncertainty and turmoil in entrepreneurship. “Should I or shouldn’t I?”

Caleb answers, “Take the leap and go build it out. You can always go get another job, and you’ll probably be a more valuable employee down the line. Because whether you succeed or fail, it’s an incredible learning experience.”


Written originally for the DataSeers blog by Robert Klasen based on an interview of Caleb Avery by Adwait Joshi. Edited by T. McLauchlin.


About DataSeers

DataSeers is an Atlanta-based B2B SaaS company that helps banks and fintechs take control of their data via onboarding, ACH processing, BSA/AML and consumer compliance, anti-fraud, reconciliation, and analytics. Its flagship product, FinanSeer® is a global enterprise solution that can help organizations across 150+ countries operate efficiently remain in compliance and have global oversight into their data.

DataSeers was built with a team of experts that understand the value that clean and homogenized data brings to enterprises to increase operational efficiency through workflow automation machine learning and AI.

DataSeers is a “One-Stop Shop” that allows API connectivity for growth, innovation and movement.  “DataSeers has thought of everything. They’re kind of like a Goldilocks solution for banks, credit unions and fintechs.” The enterprise nature of DataSeers solutions uniquely empowers BaaS banks and community banks branching into payments innovation.

Since its founding in 2017 at the humble beginnings of Adwait Joshi’s home, DataSeers is now in its fifth office in the US with nearly 100 employees worldwide.

DataSeers has 25 recognitions from their six short years in business, some of which are listed below:
2021 100 Fastest Growing Private Companies (Atlanta Business Chronicle)
2021 12 Best and Most Innovative Alpharetta Payment & Fintech Startups (Daily Finance)
2021 Most Innovation Payments Tech Company (IPA)
2021 Best Data Aggregator/Bank Partnership (Tearsheet Data)
2023 Top 10 Innovative Technology Company in Georgia (TAG)
And with a three-year revenue growth of 427%, DataSeers received ranking No. 1503 among Inc.’s list of America’s Fastest-Growing Private Companies in 2022.

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