Make Your Dream Retirement A Reality - Oak Harvest Financial

Interested in starting your own entrepreneurial journey in finance & investment but unsure what to expect? Then read up on our interview with Jessica Cannella, Co-Founder & President of Oak Harvest Financial Group, located in Houston, TX, USA.

What's your business, and who are your customers?

Our company namesake is Oak Harvest Financial Group, Oak represents the strongest tree with the deepest roots. It represents stability in retirement, legacy, and family. Harvest is what we do in retirement. We work our whole lives to accumulate our “crop,” and then it’s time to harvest our assets to last a lifetime, hence Oak Harvest. Through our holistic approach and various financial tools and investment strategies, we build a customized plan for our clients and provide ongoing guidance and support as they navigate the unique challenges and objectives unique to retirement. Our clients are preparing for retirement or living in retirement. They’ve worked really hard and want to know that they can retire and/or stay retired. They want to maximize their full retirement potential by partnering with a team of experts to execute a comprehensive plan for income and financial flexibility in retirement.

Tell us about yourself

At 14 years old, I started working with some of my friends at an assisted living facility. That job gave me a lot of perspectives. I was working with and helping seniors and got close to many. This influenced me in terms of where I am now. Around the same time that I was working at an assisted living facility, my dad began selling long-term care insurance and eventually opened his own business. I have worked in his office on and off since I was 15. I was exposed to the opportunity and challenge that is entrepreneurship. I grew up in his company and had early exposure to alternative investment strategies in the insurance space, like life insurance, long-term care insurance, and annuities. Like many family-owned practices, I would frequently butt heads with my dad on best business practices and saw an opportunity to offer more investment choices beyond the insurance realm. I met Troy Sharpe in 2008 and quickly learned we shared a similar vision for a firm that offered a truly holistic approach to retirement. I parted ways with my dad, and Troy and I partnered in 2010 and opened the Oak Harvest Financial Group Headquarters in Houston, TX. Twelve years later, we offer services to clients in all 50 states virtually and have expansion plans to establish offices in other major metro areas.

What's your biggest accomplishment as a business owner?

Making it this far and developing a deep appreciation for all the lessons learned along the way. We started our firm with about $50k capital and just us two. Today, we manage over $500 million in assets, serve over 700 families, and employ close to 40 team members. We’ve been featured in major publications, including Fox Business, Kiplinger, Forbes, and others. We received tremendous industry accolades and recognition: Citywire recognized us for being the “Fastest Growing Registered Investment Advisor In Texas, 2020 & 2021,” and RIA Edge named us the “Fastest Growing Registered Investment Advisor” in 2021. In 2023 we anticipate we will evolve from small business to midsize and have expansion plans in place.

What's one of the hardest things that comes with being a business owner?

The people part, maintaining a positive, value-driven, and client service-oriented culture requires a high level of intention and communication as a business grows internally with your team and externally with your client base. It’s important to celebrate and acknowledge accomplishments and identify and reevaluate the failures. Failure is the mother of all success, and it’s crucial to leave space for failure to happen and cultivate a culture that seeks the lesson and has the tenacity to learn and apply that learning to beget future success. Before you can afford the people, you need the capital to make a hiring investment. Having capital is very important for keeping a business afloat. Like many other businesses just starting out, we faced financial hardships that could have ended us. Strategically finding a way out of those hardships has been one of the biggest challenges I have faced as a business owner. If there’s one piece of advice I can share, it’s to always put people first, your employees, your clients, and your working relationships. Do the right thing, be cautiously optimistic with your dollar and stay consistent in that your actions are aligned with your word. Identify and communicate your company’s values; it is the foundation on which your business is built and in your core values lies all of the wisdom you need to make critical decisions, with people first and money second.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

1. Identify, define and communicate your company values.
2. Take time alone to think. This is especially important around money decisions, hiring decisions, process development, and conflict resolution.
3. Get clear on your vision for your business. Be detailed, diligent, and consistent in the communication of your vision to your team and empower them to execute that vision. Clarity begets confidence.

Where can people find you and your business?

Website: https://oakharvestfg.com/
Facebook: https://www.facebook.com/oakharvest/
Instagram: https://www.instagram.com/oakharvestfg/
Twitter: https://twitter.com/oakharvest
LinkedIn: https://www.linkedin.com/company/oak-harvest-financial-group/

If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.