Our Associates

Jason Lettenberger
Financial Services Professional, CFBS
Wauwatosa, WI

Jason Lettenberger

  • Small Business and Family Financial Representative
  • MassMutual 2019 Top of the Council Qualifier (recognizes top 125)
  • MassMutual’s Agents Association Committee Chair

Helping You Make the Appropriate Financial Decisions, Based on What Matters to You.

“Asking hard questions gets people talking about subjects they’ve been avoiding or haven’t even considered, Jason says.”  “It’s an important aspect of helping people arrive at good financial decisions for them, and it’s guided me since the day I started as a financial representative.”

If there is a conventional path to becoming a financial representative, Jason didn’t follow it. He went to technical school to build a working skillset, but discovered what really drove him was his entrepreneurial mindset. “At 23 years old, I shifted gears and partnered in a mortgage company,” Jason recalls, “and over several years helped build a thriving business. Then 2008 hit me with two life-changing events: the premature birth of twins and the biggest mortgage crisis in history.”

That double-dose of reality changed Jason’s family and his business. It also fueled his willingness to outwork anyone. A financial industry veteran recognized Jason’s potential and recruited him. “I’ve been fortunate to have great mentors and supportive family and friends,” he says. “I put pride and joy into what I do, and it’s no secret that I work best with people who like and trust me. That’s how I have built my practice organically, almost entirely by referrals. Everyone on my team is up front with clients about being hands-on. It’s about being transparent.”

One area Jason emphasizes with clients is risk management. “It can take different forms depending on whether a business needs to protect the contributions of key individuals, fund a buy/sell arrangement or develop strategies for business succession to the next generation. It’s not that different with families, and my help comes from a position of experience and understanding. You have kids? So do I. You have a budget? Me, too. But do you have a strategy for retirement, and do you have life insurance? I do. So does my wife. So do my kids! I can create a custom strategy to help you get where you want to be. After the hard work is done, I can only suggest what you should do. My role is to help you make the best decisions for you, based on what matters to you.”