Flyover’s Fireside Chat with Snappy Kraken Founder and CEO, Robert Sofia

Below is the first edition in a series of interviews with the Founders and CEOs of Flyover portfolio companies. Every quarter we will sit down with a Founder/CEO to learn more about their company, their personal background, the industry they operate in, their thoughts on entrepreneurship, and maybe even some fun facts!
To kick off our new series, we spoke with Robert Sofia, Founder and CEO of Snappy Kraken

Snappy Kraken

Robert Sofia
Founder and CEO of Snappy Kraken

About Snappy Kraken: Automated content marketing for financial advisors and enterprises that support financial advisors.
HQ: Ormond Beach, Florida
Industry/Vertical: Operating at the intersection of MarTech and FinTech

Flyover: Robert, tell us a little about yourself and your background.

Robert: I was a terrible student in high school, and I didn’t go to college, but I’ve always loved working. I started working in our family business as a laborer when I was 11 and went into sales as soon as I could drive. I discovered my passion for marketing financial services in my early twenties and I started my first company in 2009 at age 27. I exited that company in 2016 and launched Snappy Kraken later that year.

Flyover: What was your inspiration for founding Snappy Kraken?

Robert: It wasn’t my inspiration at all, actually. My business partners, Brad DeLoatche and Angel Gonzalez came to me with the idea and asked me if I would partner with them. We had already been working together for five years at my previous company so I trusted them and knew we could build something great together.

Flyover: Operating in financial services marketing for years now, what do you believe is the biggest misconception about the industry?

Robert: There are a lot of people who think automated marketing is impersonal. They equate it with things like spamming, pop-ups, and cold calling. This is largely because there are so many companies doing it wrong. Executed correctly, automated marketing is extremely personal because it is tailored to the right audience, sent at the right time, and personalized in just the right way.

Flyover: How has Snappy Kraken evolved since its formation?

Robert: Snappy Kraken has evolved in both expected and unexpected ways. In some ways, we are just fulfilling our original vision to build the best possible marketing platform for financial advisers by continuously improving our product and service. In other ways, we have adapted to market forces. For example, our initial model was freemium based, but that didn’t work because the perceived value was too low. Then we went to $39 per month, but revenue wasn’t growing fast enough. Long story short, we charge a setup fee and over $200 per month today, but we’re growing faster than ever. We’ve learned many lessons like that.

Flyover: For many, maintaining a strong culture during the transition to remote work amid the COVID pandemic has been a struggle. However, Snappy Kraken has operated remotely since the very beginning. How would you describe the culture at Snappy Kraken? How do you reinforce it remotely?

Robert: I’m obviously partial, but I think the culture at Snappy Kraken is incredible. Words like supportive, energized, fun, adaptive, and visionary all come to mind. Maintaining a strong culture while working remotely takes concerted effort, but having the right technology stack (Slack, Asana, Zoom, 15Five) and hiring the right personalities, has ensured our success in this area. We were actually ranked as one of the top ten FinTech companies to work for in 2020 and I know we owe that to our outstanding leadership team.

Flyover: What is the most valuable lesson you’ve learned since founding Snappy Kraken?

Robert: Just because you’re the founder or CEO doesn’t mean you have to be involved in every decision. Hire motivated people with integrity and relevant expertise, and then trust them to do the job you hired them for. Stay informed, but don’t slow things down by inserting yourself into every project.

Flyover: Who or what has had the most influence on your leadership style?

Robert: I attribute my leadership style primarily to three people and two personal qualities. I learned how to be an empathetic and generous businessman from my grandfather, and I learned scrappy creativity from my parents. But I’m also an avid reader and keen observer of others. When I read something I want to apply, I get to work on it quickly. When I see something I like or dislike in another leader, I try to learn from their example.

Flyover: What frameworks or mental models do you regularly lean on when making an important decision?

Robert: With endless competing priorities, I rely heavily on the Eisenhower Matrix. I used to have a visual representation of it on my desktop, but now it’s an automatic part of my thinking process. I’ve been relying on it for years to help me prioritize tasks by urgency and importance, sorting out less urgent and important tasks for delegation, deletion, or postponement.

Flyover: What has been the most satisfying moment for you as a founder?

Robert: When I get messages from our employees telling me how much they value their opportunity to work at Snappy Kraken and how it has changed their life. Or when I get notes of appreciation from our clients who thank me for how we have transformed their business — those are my most satisfying moments. And thankfully, they keep coming.

Flyover: What excites you the most about the future of Snappy Kraken?

Robert: That’s an easy one: The possibilities. The foundation we’ve laid with the current version of our software is merely that — a foundation. We have virtually endless integration, content, and automation potential ahead of us. Furthermore, what we’ve built can be applied to so many new vertical markets. Financial services is just the beginning.

Flyover: What three tips would you give aspiring entrepreneurs?

Robert: Don’t listen to the haters. Lots of people will tell you that you can’t succeed. They’re wrong. Don’t listen to your own negative thoughts. Sometimes your inner voice will tell you that you can’t succeed. It’s wrong. Everything will take longer and cost more than you expect. Keep grinding.

Flyover: What is the best way for readers to learn more about Snappy Kraken or connect with you?  

Our website:

On Twitter

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