146: Ben Filkouski – Finding Your 'Why'

Guest: Ben Filkouski

Guest Bio:

​Ben graduated from the University of Wisconsin – Madison in 2018. Upon graduating, Ben worked for Goldleaf Development, a Multi-Family Developer in Dane County, where he obtained his Real Estate License. In September of 2019, Ben joined Madison Commercial Real Estate. Since joining Madison Commercial Real Estate, Ben has become a Partner with the firm, obtained his Real Estate Brokers License, and earned his CCIM (Certified Commercial Investment Member) designation.

Ben currently serves on the board of Commercial Brokers Group Inc. (CBG) a CRE Organization based out of Madison, WI. CBG recognizes top deals completed annually, and Ben has won Land Deal of the Year in 2021 & Overall Deal of the Year in 2021, Industrial Deal of the Year in 2022, and Land Deal of the Year in 2024. Ben is also an active member in the Commercial Association of Realtors Wisconsin (CARW) where he was formerly on the NextGen Committee and was runner-up for Industrial Deal of the Year for the State of Wisconsin in 2022. Ben is also an active member with Smart Growth Greater Madison, a real estate development lobbying & networking organization.

Key Points:

Entry into Real Estate:

Ben initially resisted going into real estate despite a family background in it. He became interested after experiencing different aspects like construction, deal-making, and sales. Ben fell in love with real estate during a brokerage role, especially the dynamic nature of the work and helping clients grow.

Unexpected Career Path:

Ben originally considered a career in the arts due to a love of creative thinking and writing. He found that creativity and communication are actually essential to being successful in real estate sales.

Natural Networker:

Networking comes naturally due to a talkative personality and curiosity about people. Ben enjoys building relationships, whether or not they lead to direct business. He learned the value of strategic networking, focusing on a few meaningful conversations rather than quantity. He uses networking as a way to stay top of mind for real estate opportunities.

Team Growth & Hiring Philosophy:

Ben recently grew the team by hiring two new associates. Hiring isn't based solely on experience, personality, drive, and communication skills are more important. Ben looks for self-motivation, competitiveness, and professionalism. He emphasizes the long timeline before new brokers become profitable, so cultural and personal fit is essential.

Screening New Hires:

Ben created a detailed training portal designed to take 50–60 hours. He doesn't tell new hires how long it should take—completion speed reveals attention to detail and commitment. He uses early performance during training as a key indicator of long-term potential.

Managing Associates:

One challenge is frequent interruptions that break focus. Ben implements short, scheduled check-ins (10–15 minutes) instead of ad hoc questions. This structure improves efficiency for both managers and associates. Ben believes some level of independence should be expected after the initial learning phase.

Culture and Success Metrics:

Culture encourages brokers to "live the lifestyle"—be self-driven, schedule smartly, and network. The firm has seen improved success rates and retention since implementing more structured onboarding and evaluation systems.

Guest Links:

Connect on LinkedIn

Connect on Instagram

https://madisoncommercialre

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