“Know that bad news never gets better with time; Transparency with your stakeholders is critical” with Dennis Cail and Mitch Russo

Know that bad news never gets better with time. I am a huge fan of transparency and I have learned that if you want your stakeholders (i.e. investors, employees, users, etc.) to trust you, you have to trust them with the bad news as much as you trust them with the good news. Just have a mitigation plan and always be willing to ask for help when you need it. Leadership pride and ego is the death of most high potential companies.

I had the pleasure of interviewing Dennis Cail, CEO and co-founder of Zirtue. Dennis is a technology entrepreneur, executive and the driving force behind Zirtue, a relationship-based mobile lending app. Dennis also serves as the managing partner of Covince Capital Partner. Past experience includes serving as managing director of PwC and other enterprises, and is a graduate of the Stanford University Graduate School of Business.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I started my technical career in the Navy as a Systems Engineer setting up ship-to-shore and ship-to-ship communications configuring routers, transmitters, receivers and couplers with a top-secret clearance. After leaving the Navy to complete my undergrad in Computer Science, MBA in Finance and first job with IBM building ecommerce platforms and custom ERP solutions before moving over to their Corporate Development Team leading mergers, integrations and carve-outs. This gave me the skills and confidence I needed to launch my own boutique M&A Advisory firm with some proprietary software that I ran for several years while traveling to over 40 countries before successfully exiting that business. I’ve been a recovering entrepreneur for the last few years, before we founded Zirtue in 2018 and launched in the App Stores in 2019. It’s been a great ride, a lot of work, a lot of fun and there is so more to come.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

The aha moment came several years ago after a few family members borrowed money from me, on a regular basis and I had very limited success getting that money back. So technically speaking, I had multiple eureka moments. Most of these loans to friends and family were situational loans for things like rent, auto loans, travel, utilities and medical expenses. Like most of us, I don’t mind helping those close to me if they need help and if I am in a position to help. We all need a financial lifeline from time-to-time. My thought process was simple in that there should be a way to help your friends and family when they need a little help, while removing any relationship awkwardness. From there the ideation phase of Zirtue was born.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

I came from very humble beginnings on the other side of the tracks growing up in public housing during the better part of my early childhood. I know first-hand what it’s like to grow up poor and to not have access to money for your basic needs. This experience gave me an early and hard lesson on how to do a lot with a little. There was not a bank in the neighborhood I grew up in. Paychecks were cashed in the local grocery store, liquor store or pawn shop and subsidized by food stamps. We still have a large working poor population today as we did then, whose income falls below the poverty line. I am extremely grateful for where I am today financially, but I know where I am from and I know what it’s like to need and not have. I believe in the power of communities and what they can do to lift you up. I am living proof of that. Like most of us, my childhood shaped me and gives me the drive and determination I have today to create a more financially inclusive world by mobilizing loans between friends and family.

So, how are things going today? How did your grit and resilience lead to your eventual success?

We’re hiring! Things are going great — we’re scaling quickly and there’s a lot of excitement around the Zirtue office. We’re growing over 50% month-over-month with over half of that growth coming from organic growth. That’s exciting for us because that means our registered users are actively sharing Zirtue with their friends & family as a new and refreshing way to lend or borrow money.

With respect to my grit and resilience, an entrepreneur has to have grit if he or she is going to have any chance of succeeding. Entrepreneurship is not for anyone with a weak stomach because your resilience will be tested daily in ways you are not thinking about today. For me personally, I have a high tolerance for failure, but I never accept anything less than success.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I don’t typically use the words funniest and mistake in the same sentence. However, when I made the mistake of thinking I could still code like a pro, as I did 20 years ago was actually my funniest mistake when we launched the company last year. Let’s just say that some things are not like riding a bike, more like use it or lose it and the re-learning curve was longer than planned. I spent a lot of late nights laughing at myself, but a little determination and open-source code goes a long way.

What do you think makes your company stand out? Can you share a story?

There are a few key things that make us stand out, including the fact that Zirtue is the first relationship-based lending application to simplify and formalize loans between friends, family and trusted relationships. Essentially Zirtue allows you to request and automatically repay unsecured personal loans with friends & family. The number one comment we hear from our users is “I wish I had this app years ago.”

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Follow your instincts, admit when you’re wrong, course correct and move on quickly. There is no value in delay, always have a bias towards action.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There are so many people (friends and family) from my childhood to present day who have played a key role in my success and helping me along the way and continue to help me today. I would not be where I am without them. I am always humbled by all the love and support I’ve received from others my entire life. That said, I am most grateful for my wife Annika. I would not be able to do all that I do today if she wasn’t here to do all that she does for me and our family.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Approximately how many users or subscribers does your app or software currently have?

Zirtue is currently trending towards 100,000 active users with a 50% month-over-month growth rate

Can you share with our readers three of the main steps you’ve taken to build such a large community?

We launched Zirtue with a three-step plan — Focus on user experience, stay lean and hire the right people. We are obsessed with all three and believe this has allowed us to scale quickly.

What is your monetization model? How do you monetize your community of users? Have you considered other monetization options? Why did you not use those?

Zirtue makes money by charging a 5% service fee for each loan. We have considered other monetization options, but like most apps our monetization models is highly connected to user experience. It’s impossible to separate the two. FinTech companies like Zirtue come with baked in friction points due to Know Your Customer (KYC) and Anti-Money Laundering (AML) laws, so go out of our way to avoid adding any new or additional friction points by way of a complex revenue model that may create a less than optimal user experience.

Based on your experience and success, what are the five most important things one should know before one wants to start an app or a SAAS? Please share a story or an example for each.

1. Know why you are starting your app before you start. I’m a huge fan of Simon Sinek’s book, Start with Why. The premise is you have to start with the Why to get to the How and What. The Why for Zirtue is to create a more financially inclusive world by mobilizing and digitizing loans between friends and family.

2. Know your blind spots and solve for your gaps. This requires you to part ways with your ego and admit your weaknesses. A good example of this is my decision to partner with my co-founder, Michael Seay. Michael is a strong financial engineer and I am extremely efficient as a technical engineer. This brings immediate value and traction to our FinTech company and that combination of skillsets has allowed us build and scale quickly.

3. Know that you can’t do it alone. This is an extension of know you’re your blind spots. I couldn’t do anything I do without a strong team around me.

4. Know your market and if you don’t know it, learn it fast. An example of this would be all the research we did prior to launching Zirtue to understand the market we were seeking to disrupt. Simple premise being you don’t have a business unless you have a clear market to support that business.

5. Know that bad news never gets better with time. I am a huge fan of transparency and I have learned that if you want your stakeholders (i.e. investors, employees, users, etc.) to trust you, you have to trust them with the bad news as much as you trust them with the good news. Just have a mitigation plan and always be willing to ask for help when you need it. Leadership pride and ego is the death of most high potential companies.

Thank you for all of these great insights!


“Know that bad news never gets better with time; Transparency with your stakeholders is critical”… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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