We just want to invite really good people into the organization, treat them well, and give them the opportunity to be successful. Hopefully, they find this environment is one they can grow in.
Michael S. Sheppard, CFP®
Managing Partner/Founder
IronwoodDrive Financial Group, LLC

Michael Sheppard, Managing Partner, IronwoodDrive Financial Group, LLC
Michael Sheppard, a servant leader, carefully built into IronwoodDrive Financial Group (IFG) many of his core values: opportunity, engagement, diversity, optimism, compassion, and growth for everyone—clients and staff. His style of leadership, most likely, is what enabled IFG to navigate the pandemic and achieve even greater success.
For those unfamiliar with the term, “servant leadership,” here, according to Indeed.com, are some of its characteristics: listening, empathy, healing, awareness, persuasion, conceptualization, foresight, stewardship, a commitment to the growth of people and building a community within one’s company.
In the many anecdotes Michael provided during a recent conversation with Small Business Milwaukee, it’s easy to pick out those very characteristics. It’s also fun to imagine how much better other work environments could be under such guidance.
Diversity is integral to IFG. “I’ve been a part of a lot of diversity and inclusion initiatives, and a lot of them remained initiatives and didn’t really turn into results. I’m a results-oriented guy,” said Michael. He added, “I wanted to build an organization where nobody feels like they’re the only one. Here we believe that all people are beautiful and all people are smart and all people can work hard together. I’ll either go bankrupt trying to do that or, hopefully, have a solid team live the life they dream.”
In all recruiting and team meetings, he stresses the importance of being just as big and just as profitable as the other financial services firms around while reflecting the market. In fact, that’s part of IFG’s mission statement. A look at IronwoodDrive’s “Our Firm” page shows the diversity Michael has been able to achieve.
Here’s something interesting. While he cautions that time always adjusts, IFG has a 100% retention rate for advisors who enter his residency program and 67% overall.
The group’s first full calendar year as a business was 2020. Michael says, “It was extremely scary and hard for us in the midst of Covid because a lot of people don’t trust you with their money or running their benefit plans without shaking your hand and meeting you in person.” That did not deter IFG.
“We found that a lot of people wanted more financial wellness education and guidance than a specific product. We dug deep into that void,” explained Michael. Here’s what they did: for all the companies whose 401(k) plans are managed by IFG, Michael and his advisors saw over 1,200 employees by screen. “We sat there in front of the camera and talked about risk and reward. We talked about the pros and cons of tapping into retirement funds. We asked how much they needed as opposed to taking it all. Sometimes people just need to talk it out and we gave people that space. It really helped all of us.”
Michael elaborated, “That’s one of the things that differentiates us in the marketplace. A lot of my peers solely want to talk to the people who run the company, but they don’t necessarily want to go on a shop floor and shake someone’s hand that has oil on it. We are exceptional with the employees and we make everyone feel comfortable.”
Was all that hard work worth it? Michael stated, “A lot of those plans have grown significantly because now we have more people making better decisions for their financial future.”
How else did IFG benefit from the tumultuous 2020? They were able to tap into a pool of talent the larger companies couldn’t keep due to necessary layoffs. It meant IFG was able to hire talented individuals they otherwise might not have had access to.
There are no quotas at IFG. Instead, Michael explained, “We’re all revenue based. Their only quota is to do good work and generate enough revenue to meet the potential I saw in them when they came into the organization.”
Towards the end of the conversation, Michael was asked if there was anything he wanted to add. He asked that this be part of his message:
We don’t sell products. We advise clients. The tools we use are driven by who those people are. We just want to do what’s in our clients’ best interests at all times.
IFG has a ribbon ceremony coming up soon to celebrate their new office at 111 E. Kilbourn Avenue. Here’s another sign of their success—they plan to add more employees during 2021.
IronwoodDrive Financial Group provides the following services:
- Comprehensive, fee-based financial planning
- Retirement plans and qualified plans
- Employee benefits
- Investments and asset management
- Insurance protection
- Estate planning
IronwoodDrive Financial Group, LLC, is independently owned and operated. Certified MBE by the NMSDC. Certified DBE by Milwaukee County.
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