Josh Ackerman, CFP®
Financial Life Planning for Owners of Family Businesses
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Serving Clients Nationwide
Financial Life Planning for Owners of Family Businesses
Areas of Focus
- Financial Life Planning
- Insurance
- Investment Management
- Owning a Business
- Retirement Planning
- Taxes
About Josh Ackerman, CFP®
Hi, I'm Josh Ackerman. I joined my father Tom's financial planning practice in 2006 after spending nine years at Lexmark in supply chain and sales, work that taught me valuable business skills but left me searching for deeper purpose.During a pivotal lunch conversation with my dad, I realized I needed to be doing something that had a more positive influence on the world than selling printers. By that Friday afternoon, I had closed one last deal and signed up for my first Certified Financial Planner course, earning my CFP® designation in 2009. What began as curiosity became a lifelong commitment to helping business owners navigate the most significant financial transitions of their lives.
At Context Financial, I've built my practice around values-based financial planning that treats planning as an ongoing process, not a one-time product.
I specialize in working with family-owned businesses and entrepreneurs who are preparing for succession, sale, or retirement, transitions that require both technical expertise and deep emotional intelligence.
I often tell people that financial planning is "the most liberal arts career ever created" because it blends math, psychology, and communication to help people align money with meaning. My approach focuses on transparency and fit above all else, if a prospective client and I don't connect, the worst thing I could do is convince them to work with me anyway.
As a member of the Financial Planning Association and partner at Context Financial, I'm committed to what I call "speaking financial": translating complex concepts into language everyone can understand. I also serve as an adjunct instructor in the Certified Financial Planner Certificate Program at the University of Kentucky's Gatton College of Business, where I share my passion for relationships-first, numbers-second planning with future advisors.
I host the "Transition Talks" podcast, exploring everything from maximizing business value to preparing emotionally for life after exit. My educational background includes a degree from Macalester College and a Master's degree from the Patterson School of Commerce and International Diplomacy at UK.
Growing up in a household with two polar opposite approaches to money gave me unique insight into how our emotional relationship with finances shapes every decision we make. I help clients identify whether they're operating from scarcity or abundance and find the balance between fear and optimism that creates both security and growth. For me, success isn't measured in assets, it's measured in the confidence my clients feel when they can see the full picture of their financial future and feel truly prepared for what's next.
Professional Designations
- CERTIFIED FINANCIAL PLANNER ®
Affiliations
- Financial Planning Association
Primary Location
120 Kentucky Avenue, Suite 120, Lexington, KY 40502
Video
Meeting Options
- Video Conference
- In-Person
- Phone
Compensation Methods
- Hourly Rate
- One-time Financial Plan
- Percentage of Assets Managed
- Subscription
What to expect in the first meeting
Are you ready to stop worrying about how to pass on the business and receive enough money to live on? Click the 'Book Intro Call' button above and take the first step to feeling confident you have transitioned the company in the best way possible for you and your family. We'll get to know each other and I'll listen to understand your unique circumstances so we can determine the best way to proceed. I look forward to speaking with you.Offers Investment Management
Yes
About Context Financial
Context Financial is a Lexington, Kentucky-based financial planning firm that my father Tom founded back in 1980 when he started in the insurance business. He quickly realized that insurance and the peace of mind it offers is only one component of a healthy financial plan, so he expanded into investment management in the late 1980s.I joined the practice in 2006 and earned my Certified Financial Planner™ designation in 2009. Today, my father and I work together as partners, along with Brittany Hamilton, our financial administrator who brings her passion for finances and helping others stay organized to everything we do.
What sets our firm apart is our commitment to Financial Life Planning, a holistic process that considers your entire life, not just your financial life. I help you clarify your values, priorities, circumstances, and aspirations before designing a plan for the future that makes sense for you specifically.
Our philosophy is liberating for those of you who are disillusioned with using your lives merely to make money. Instead, I ask what would bring meaning to your financial life beyond traditional discussions of assets and net worth.
My approach centers on applying expertise with empathy and caring deeply about you as a person. I understand that your goals are more than financial health, I seek to understand your holistic goals and apply our decades of experience to meet them. I'm committed to putting your needs first, treating our relationship with the passion and dedication I'd give to family.
I know who I am and what I stand for, but I'm also open-minded, asking questions and listening intently so I can craft the right plan for you.
When you work with me, you can count on me through both the highs and the lows. I strive to do good work, take responsibility when times get tough, and always maintain a positive outlook. As your partner for the journey, I'll help you find the right questions to ask and guide you toward clarity as you write your own story. Because ultimately, you deserve peace of mind.
Education
University of Kentucky, Patterson School Masters, International Commerce | Macalester College Bachelor of Arts (B.A.), Political Science and Government
Hobbies and Interests
- Family
SEC Lookup
View DisclosureWho We Serve
- Baby Boomers
- Business Owners
- Dual Income Family
- Entrepreneurs
- Gen X
- Intergenerational Families
- Living in Retirement
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