Jason R. Hill discovered the entrepreneurial spirit at a young age. In his childhood, he helped his dad at his shop, sold candy on the school bus, ran a lemonade stand, and during his high school and college years, he worked as a sailing instructor.
He graduated from the University of Delaware with a finance degree and landed a job at ADT Security that helped him hone his sales skills. This experience assisted him in securing a job at John Hancock Financial Network, where he would learn valuable lessons to become an independent financial services professional. Later he went on to found his first company, Client Focused Advisors, and he heads it as its Financial Advisor, President, and CEO.
His next big entrepreneurial idea struck him when he was on his way to the office during the early stages of the COVID-19 pandemic in 2020. He realized that we’d gotten so deep into social media that we put our guard up, creating so much friction to get in touch with someone. This was a big problem, especially during the COVID-led lockdown when people craved human connection. He founded Owwll to break the conversation barrier and facilitate 1:1 private audio calls, whether it’s personal or business.
We recently caught up with Jason in an interview, where he delved into his entrepreneurial journey, and the Owwll story, and shared invaluable advice that would help budding entrepreneurs in their own journey.
- Walk us through your entrepreneurial journey.
My journey really began in childhood, with the early influence of my father and mother as my mentors. Back in the 80s, my father, a successful entrepreneur, played a significant role. He owned a store called Captain Hooks in New York City, located at the South Street Seaport, a major tourist attraction. This was where my lessons in entrepreneurship began.
At a young age, I would assist in the store, managing the cash register, providing change, and interacting with customers. These experiences taught me the ropes of entrepreneurship. As I progressed through my early years, I even ventured into selling candy at my elementary school, displaying my early entrepreneurial spirit.
Later on, I pursued higher education, attending college. After completing my studies, I dived straight into the financial services industry, becoming a financial advisor. Even now, I maintain my registration as a financial advisor. Starting out, I had to build my business from the ground up, focusing on marketing to develop a client base. The financial service sector gives you two paths: a salaried position or building your independent practice. Naturally, I chose the entrepreneurial path.
Being intrinsically entrepreneurial, I aimed to carve a niche market and grow my business steadily, one client at a time. Networking, effective communication, and education were the key elements that helped me expand. Educating consumers was crucial; an informed client was more likely to collaborate. Gradually, I succeeded in building and scaling a robust financial service business that still stands strong today.
- Please shed light on the Owwll story.
It all started during my daily car commute to work. This routine began during the COVID-19 pandemic, around April and May of 2020, when everyone was confined to their homes.
During these times, with the shift toward digital communication through text messages and social media apps, it struck me that this mode of communication was somewhat limited. Driving to work, I realized I could only listen to music, a podcast, or an audiobook. If I glanced at my phone and its extensive contacts list, I couldn’t just call anyone spontaneously.
It seemed odd that with so many contacts, there was no easy way to initiate a conversation. People were craving connections and conversations, especially during a time of limited human interaction due to the pandemic.
Around the same period, we witnessed a surge in the popularity of podcasts, indicating a growing need for meaningful discussions. However, there was no platform facilitating impromptu conversations among like-minded individuals. This realization motivated me to put pen to paper and start developing the concept that would later become Owwll.
I reached out to Oz Digital Consulting and proposed the idea: could they develop a specific technology? Amjad Shamim, the CEO, and his son Sam Jafri, the Client Advisor at OZ Digital Consulting appeared on my podcast, Boca Raton Shrimp Tank. Knowing their background in app development and that they were working on a COVID app at the time, I shared my concept with them.
Sam had this unique idea: to build an app allowing people to make in-app calls on demand without revealing their phone numbers. Privacy in conversations was a key aspect.
The pivotal moment happened in August 2020. We engaged in a rigorous 3-4-week Minimum Viable Product (MVP) session with OZ Digital Consulting. Daily, we brainstormed and created different elements, envisioning what Owwll is today.
At the end of this immersive experience, we had an extensive 100-page document outlining Owwll’s potential, complete with various wireframes. A significant decision lay ahead. I had invested a few thousand dollars in the MVP. I could have compiled this into a PDF PowerPoint and tried to secure funding, or explored other options, getting competitive quotes.
So, I got multiple quotes to better understand the potential costs and what others thought of the project. After evaluating all options, I was impressed with what OZ had to offer. Around 2-3 months after the original MVP was completed, we reached a business agreement in November. Legalities were settled in November and December, and development commenced in January 2021. We made it happen.
- Any hurdles you encountered to make Owwll a reality?
One major hurdle was committing to building it. Often, entrepreneurs get caught up in the costs of app development and hesitate, hoping someone else will fund their idea. In my case, I recognized that this was my moment. I had worked hard throughout my career to reach this point and had saved up a substantial amount of money. While everyone was cautious about spending, I saw the potential and dove into the project.
It was a time when the world was dealing with the pandemic, wearing masks, and no vaccine yet. Despite the uncertainty, I pushed forward because I believed in the project. Through my podcast, The Shrimp Tank, I sensed a shift in human interaction. People were expressing the “you only live once” sentiment. The “great resignation” was becoming more apparent, with business owners signaling change. With over 300 shows between The Shrimp Tank and the Owwll Podcast, I had a good grasp of the entrepreneurial landscape.
I foresaw a growing need for networking and quick access to advice as more people embarked on their entrepreneurial journeys. Owwll was conceived to address precisely that. It’s a platform where you can instantly network and collaborate, fostering opportunities. Additionally, it provides a way to seek advice swiftly, which is crucial in today’s challenging entrepreneurial environment. People often need advice promptly, and Owwll bridges this gap, connecting all the essential dots.
- What are the traits of successful startup leaders?
Leaders often rely on their intuition amidst a cacophony of critics and well-meaning mentors. Specifically in the realm of mobile apps, there are numerous pathways to success. As a leader, trusting your intuition is crucial in decisions regarding marketing strategies or feature deployments. Analysis paralysis is a common pitfall—overthinking and excessive research can hinder progress. I prioritize feedback from our platform’s users and our community, valuing their input greatly. Less weight is given to advice from individuals who haven’t engaged with the platform themselves.
A significant aspect of leadership involves keeping a close eye on the financial aspect. Many fail due to not managing their finances effectively, especially in the context of app development. Often, startups exhaust their funds building the MVP and fall short when it comes to marketing or sustaining the product. Understanding the true costs of development and maintenance is essential. It’s vital to budget for marketing as well, considering the highly competitive nature of app markets. The failure of most apps can be attributed to a lack of a robust go-to-market strategy and inadequate funding to implement it. The conventional approach of creating an MVP and then seeking capital isn’t always sufficient in the current landscape flooded with millions of apps.
The reality is that angel investors and venture capitalists often steer clear of investing in apps. Many apps struggle to generate revenue and gain traction, making it a risky investment. Startup founders frequently envision their app becoming the next big thing like Instagram, but investors have heard this narrative countless times. Investors seek more than just bold claims; they want a solid plan.
My advice is straightforward: prospective entrepreneurs need to meticulously plan their finances before taking the leap. Personally, I carefully evaluated my financial situation, ensuring I had a substantial runway even if things got tough. It’s worth noting that my journey was far from easy. I had underestimated the challenge of persuading people to download yet another app. There’s a prevailing sentiment that new apps won’t endure, dissuading potential users from engaging. This skepticism is akin to my early days as a financial advisor when people doubted the longevity of my practice. In both cases, building trust and overcoming skepticism were pivotal.
In the app world, marketing is incredibly challenging. However, building a strong community has proven to be a successful strategy. Engaging with early adopters, fostering their belief in the platform, and encouraging them to spread the word has been crucial. It’s not always about monetary incentives; genuine engagement and support go a long way. Success in the mobile app space now hinges on cultivating a passionate community that genuinely believes in the leader and the platform’s potential impact on millions of users.
- What were some of the key milestones or achievements that you personally marked as signs of improvement or checkpoints in your entrepreneurial journey? How would you correlate those with taking the app forward in parallel?
One of the most remarkable aspects is observing the unsolicited reviews people post on various social platforms. I never encouraged these, but if you visit LinkedIn, Instagram, or even Threads today and search for #Owwll, you’ll find numerous posts by people. Reading these positive comments is incredibly heartening.
This positive momentum started over a year ago during the beta phase when individuals began predicting that this would be the next major platform. Their enthusiasm and support inspired me to persevere. As an entrepreneur in the realm of mobile apps, you experience extreme highs and lows. It’s akin to riding a roller coaster.
On a Friday, you may feel confident and optimistic, believing everything is falling into place. Yet, by Monday, when you review the data, doubts can flood your mind, making you contemplate throwing in the towel, convinced that your efforts aren’t yielding the desired results. However, what keeps me going is the influx of messages I receive every week.
Most people are unaware, but I personally reach out to each person who applies to become an Owwll expert, connecting with them on LinkedIn and extending a warm welcome to our community. Their responses are overwhelmingly positive, expressing their love for the platform and their belief in its long-term impact and value. I keep these messages as a constant reminder.
Whenever I encounter criticism, be it a negative review in the App Store or a critical response on Instagram, I glance at these encouraging remarks. They motivate me to persist, especially during those times when I’m scrutinizing my bank account and assets, feeling a wave of anxiety.
You know, the things I’ve had to do to keep Owwll where it is today. Some of the motivations behind proceeding and some of it is just looking down at the app and seeing people on calls. One thing I’m certain of in my life is that amidst all this crazy technology with the Metaverse, ChatGPT, and AI, one thing will never fade away: human connection. People will always want to go to that local bar and have a drink. People will always want to attend that local networking event and chat, and Owwll is as simple as that. It is creating human connections to help people connect better—it’s a connection tool in their toolbox.
- How well did people receive Owwll?
Two people went live on the platform and were talking when we had under 100 downloads, very early in the beta environment. Both of them reached out to me, telling me how cool it was that Owwll connected them. They had never met before. What keeps me going is seeing these stories. One person flew to Iceland to speak, getting a public speaking opportunity after speaking to someone on Owwll. When you look on socials this week, you’ll see everyone joining up and doing podcasts. They had never known each other before Owwll, but they connected on the platform, and now they’re podcast swapping for Owwll week. It’s incredible to see people running clubhouse rooms without me, talking about why people should leverage this platform for their expertise and their business. It’s just absolutely amazing. And of course, the biggest thing that people leave out: everyone thinks about this platform as a way to connect and help your business, but people forget it also helps on a personal level.
When you look at how many people are lonely in this country and just want to speak with someone, especially considering the mental health of young males in their 20s, it’s clear this platform can be a tremendous help. It provides an avenue for those who feel lonely to engage in conversations, fostering human interaction. On the personal side, we’ve witnessed individuals chatting privately in a secure place, enhancing their personal lives. This could range from discussions about physical fitness and nutrition to sharing insights on managing diseases like multiple sclerosis.
- What advice would you give to an entrepreneur or leader who is treading a similar path to yours?
In your journey, anticipate numerous failures and challenging days during your initial 12 to 24 months. This is completely normal. Being a solo entrepreneur can be lonely; it’s a quiet space where you’re striving to scale a brand, and although people are supportive, they don’t always comprehend the entirety of your experience. Maintain the confidence that, behind the scenes, they aren’t privy to everything you’re going through. Don’t take comments personally; instead, keep your end goal in mind and have a flexible plan in place. It’s crucial to be able to adjust from that plan as needed.
Often, we become fixated on our initial expectations, and our egos hinder us from changing directions. It’s important to follow your intuition and embrace the direction you want, even if it means discarding work or investments. Always prioritize effective communication, integrity, punctuality, and delivering excellent service. This ensures you never have to constantly watch your back and can invest your effort with confidence, avoiding the need to fake success. Authenticity and integrity should always be at the core of your business approach.
Read more:
Wearable Technologies Inc. – Preventing Preventable Accidents, Saving Lives
Elevating the Everyday Hero with AI – The Power of WageUp Inc.
OZ Digital Consulting – Get Ahead of the AI Curve
As a visionary Business and Technology Leader, I bring a proven track record of driving innovation, fostering collaboration, and delivering exceptional results in fast-paced and dynamic environments. I have honed outstanding skills in articulating a compelling vision and rallying active support from internal executives, development teams, and client business and IT leadership. I am proud to be a member of both the Forbes Technology Council and HITEC (Hispanic Technology Executives Council), which underscores my commitment to being at the forefront of industry trends and developments.
My special talent is demonstrating value to clients at all touch points – I instill these concepts in my teams.
