Ricky Shah is the Director of Kumon Chesterfield, a high-performing education franchise known for its strong enrollment and operational discipline. A former Kumon student who completed both the math and reading programs, Ricky’s story comes full circle as he eventually acquired and now leads the same center where he once studied and taught. His background spans teaching, nonprofit work, statewide political campaigns as a field organizer, and entrepreneurship through operating UPS Store franchises with his family before transitioning fully into the Kumon business.

In this conversation with Raj Tut, Ricky breaks down what it takes to scale a people-driven business: redefining delegation as a strategic growth tool, identifying the “1–3 tasks only I can do,” and systematizing everything else through hiring, training, and clear accountability. The episode also explores family business dynamics, the challenge of separating work from home life, and lessons learned from leading through disruption—especially during the COVID transition and operational crises like severe weather. Key themes include building trust through consistent communication, training for real-world scenarios, maintaining standards through culture, and leading calmly when the team looks to you for direction.

Connect with the Host

Twitter: ⁠twitter.com/ItsRajTut⁠ ⁠

LinkedIn: ⁠https://www.linkedin.com/in/rajtut/

⁠Instagram: ⁠instagram.com/ItsRajTut⁠

TikTok: ⁠https://www.tiktok.com/@itsrajtut

Kumon (National Website): https://www.kumon.com/

Email: chesterfield_mo@ikumon.com

Phone: (636) 537-5522

Timestamp:

00:00 Delegation philosophy and focusing on tasks only the owner can do

01:35 Introduction to Ricky Shah and Kumon Chesterfield

02:19 Early journey as a Kumon student and love for math and learning

04:17 Post-college path through nonprofits and burnout from red tape

05:42 Transition into statewide political campaigns

07:50 What campaign work actually looks like and the role of a field organizer

09:32 Extreme work hours, pressure, and leadership lessons from politics

12:42 Shift into entrepreneurship and family business roots

15:06 Operating UPS Store franchises as a family-run business

18:29 Pros and cons of working with family and taking work home

20:46 How a Kumon center operates day-to-day

22:37 Individualized learning, fluency metrics, and student progression

25:32 Director influence vs standardized curriculum across Kumon centers

27:44 Full-circle story of acquiring the same Kumon center he grew up in

30:22 Taking over during COVID and adapting operations

32:40 Leading through disruption and maintaining calm in crises

34:22 Diagnosing learning gaps and adapting to post-COVID students

36:13 Leadership presence and why the team looks to the leader in emergencies

38:44 Hiring, training, and building accountability through systems

40:38 Transitioning from instructor mindset to director mindset

42:36 Working on the business instead of in the business

45:56 Passion, trust, and long-term student success

50:08 Deciding what to delegate and what to keep

54:20 Why Ricky personally handles parent meetings and sales conversations

55:56 “Hole in one” advice on delegation and scaling a business

This podcast is brought to you by Storyboard Living.

If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email deals@storyboardliving.com

Connect with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/

Connect with the Guest

In this episode, we sit down with Rob Zeitler, President and Co-Founder of FLEX Payment Solutions, a family-owned B2B fintech company specializing in payment processing for niche and highly regulated industries. With over 20 years in the electronic payments space, Rob has helped build FLEX into a direct-payment processor serving sectors like consumer lending, CBD/hemp, tribal and native-owned businesses, and emerging cannabis markets, while earning a spot on the Inc. 5000 list for multiple consecutive years.

Rob walks Raj through his entrepreneurial journey—from funding legal settlements and building custom software without being a programmer, to exiting that first venture, joining his family’s lending business, and eventually launching FLEX to solve real-world payment pain points. He explains how FLEX built a moat around compliance and regulation in “high-risk” markets, why they’ve leaned into hyper-focused niches like tribal lending and cannabis, and how EOS-style systems have allowed him to stay in the visionary seat instead of doing everything himself. Along the way, Rob shares his philosophy on hiring people smarter than you, preparing the next generation of his family to join the business, the future of compliant cannabis payments, and his “hole in one” advice: don’t be afraid to ask for help, give without expecting something in return, and surround yourself with people who make you better.

Connect with the Host

Twitter: ⁠twitter.com/ItsRajTut⁠ ⁠

LinkedIn: ⁠https://www.linkedin.com/in/rajtut/ ⁠

Instagram: ⁠instagram.com/ItsRajTut⁠

TikTok: ⁠https://www.tiktok.com/@itsrajtut

Connect with the Guest

Rob’s Linkedin: https://www.linkedin.com/in/rob-z-9524273/

Company LinkedIn: https://www.linkedin.com/company/flex-payment-solutions

Email: rob@flexpaymentsolutions.com

Timestamps for Key Segments

00:00 Opening & Introduction to Rob Zeitler

05:10 Rob’s First Business and Early Entrepreneurial Lessons

10:20 Transition to the Family Lending Business

15:30 Discovering Payment Innovations & The Spark for FLEX

20:40 Entering Regulated & Niche Markets (Lending, CBD, Hemp)

25:50 Working With Native American Tribes

1:00 Technical Challenges, Compliance & Operating in High-Risk Industries

36:10 Hiring the Right People & Learning Not to Do Everything

41:20 Implementing EOS and Stepping Into the Visionary Role

46:30 The Future of FLEX & Cannabis Payments

51:40 Rob’s “Hole in One” Advice

56:50 How to Connect With Rob & Episode Closing

This podcast is brought to you by Storyboard Living.

If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email deals@storyboardliving.com

Connect with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/

Jason King is the Director of Real Estate and Impact Investing for Lewis and Clark Holdings, the Hillman family office, where he oversees investments across real estate, clean energy, affordable housing and tax-related strategies. Over his career, Jason has invested close to $1 billion across more than 4,000 multifamily units, student housing, industrial, and medical office properties. He shares how his path from rural Michigan to urban planning, affordable housing development in Chicago, and ultimately landing in St. Louis shaped his empathetic, community-focused approach to capital allocation.

In this conversation, Jason and Raj dive into how family offices think about risk, partners, and long-term holds; why tax credits and clean energy are powerful but complex tools; and how Lewis and Clark evaluates deals across multifamily, industrial, senior housing and solar. Jason unpacks a case study in innovative skilled nursing (“cottage” model vs legacy facilities), explains why reputation and alignment with partners are non-negotiable, and talks candidly about the challenges and opportunities in St. Louis—transit, density, regional collaboration, and downtown perception. They also explore where development still pencils, which asset types look compelling over the next 10–20 years, and Jason’s “hole in one” advice: there’s no such thing as a good deal with a bad partner.

Connect with the Host

Twitter: ⁠twitter.com/ItsRajTut⁠
LinkedIn: ⁠https://www.linkedin.com/in/rajtut/
Instagram: ⁠instagram.com/ItsRajTut⁠

TikTok: ⁠https://www.tiktok.com/@itsrajtut

Connect with our Guest

LinkedIn: https://www.linkedin.com/in/jason-king-1239244/

Timestamps for Key Segments

00:00:00 How Jason approaches research, expertise, and networking when entering new asset classes

00:01:03 Jason’s background: rural Michigan, urban planning, affordable housing, and career path before St. Louis

00:07:05 Early real estate lessons: managing zoning hearings and navigating diverse stakeholder interests

00:10:19 Jason’s perspective on St. Louis: strengths, challenges, and regional collaboration

00:14:32 What Lewis & Clark Holdings is and how a family office operates

00:16:09 Understanding tax credits, affordable housing finance, and the move into clean energy

00:23:35 Real estate strategy: acquisitions vs development, long-term holds, partner selection, and risk

00:27:17 Case study: the “cottage model” skilled nursing investment and how COVID validated it

00:38:34 Asset classes for the next decade: multifamily, shallow-bay industrial, data centers, and solar

00:56:29 Jason’s hole-in-one advice: there’s no such thing as a good deal with a bad partner

This podcast is brought to you by Storyboard Living.

If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email deals@storyboardliving.com

Connect with us at our Website: https://storyboardliving.com/

LinkedIn profile: https://www.linkedin.com/company/storyboard-living/