Episode Overview

In this episode, Roland Howard sits down with John Kingma of Old Glory Bank to explore what it takes to build a digital-first bank in a rapidly consolidating financial industry. As traditional institutions move upmarket, small businesses and everyday Americans are increasingly left behind.

Old Glory Bank was built to serve that gap, launching nationwide and reaching customers in all 50 states within just two weeks. The conversation dives into the realities of starting a bank, from regulatory pressure to operational scale, and why so few new institutions are entering the market.

John shares how Old Glory approaches digital transformation differently, treating it as the core experience rather than a secondary channel. The bank’s flexible technology strategy enables faster innovation, while its distributed workforce allows access to top talent across the country.

The discussion also covers the future of banking through embedded finance, including crypto and stablecoins. Old Glory is building a fully integrated experience where customers can move seamlessly between fiat and digital assets, enabling faster payments and greater flexibility for small businesses.

Finally, the episode highlights the importance of financial health and education, with upcoming tools designed to help consumers and business owners better understand their financial position, improve outcomes, and grow over time.

Episode Timestamps

[00:00] Introduction

[00:18] Banking consolidation and market gaps

[01:23] Why small businesses are underserved

[02:13] Scaling to all 50 states in two weeks

[03:06] De-risking and politicization in banking

[04:32] The challenge of starting a bank

[06:22] The shrinking future of banking options

[07:09] Why fintechs underestimate banking

[07:35] Personal motivation and small business roots

[08:08] Building a flexible tech stack with Q2

[09:11] Crawl, walk, run approach to innovation

[09:48] Talent strategy and distributed workforce

[11:23] Hiring outside traditional banking

[12:38] The emotional nature of switching banks

[16:14] Where digital transformation fails

[18:00] Entering crypto and stablecoins

[19:16] Why invest in crypto now

[20:08] Avoiding fintech disintermediation

[21:47] Financial health and wealth tools

[23:02] Customer feedback driving product decisions

[23:54] Crypto in business payments

[25:12] Business insights and financial tools

[26:21] Closing and where to learn more

Want to work with Propagate Fintech? Fill out a contact form at www.propagatefintech.com

Nearly 40% of Americans can’t cover a $400 emergency expense. That statistic alone explains why financial stress has become one of the biggest hidden issues in the workforce today.

In this episode of the Propagate Fintech Podcast, Roland Howard sits down with Rachel Fox of Sunny Day Fund to unpack the growing problem of financial precarity and why emergency savings is emerging as one of the most important new employee benefits.

Sunny Day Fund helps employers offer payroll-deducted, employer-incentivized emergency savings accounts that allow workers to build liquid savings for unexpected expenses. Instead of relying on credit cards, payday loans, or 401(k) withdrawals, employees can create a safety buffer that reduces financial stress and improves workplace stability.

Rachel explains why traditional financial wellness programs often fail to change behavior, how employers can meaningfully support workers who are living paycheck to paycheck, and why emergency savings and retirement savings need to be treated as two different financial tools.

The conversation also explores how banks and credit unions fit into the ecosystem, the role fintech plays in financial inclusion, and why storytelling has been critical to Sunny Day Fund’s growth.

If you’re interested in fintech, financial wellness, HR technology, employee benefits, or financial inclusion, this episode provides a practical look at one of the fastest-growing categories in workplace benefits.

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Chapters

00:00 Introduction and financial precarity in the workforce
00:49 What Sunny Day Fund is solving in the market
03:42 Why emergency savings matters more than most people realize
06:27 Breaking down the employee benefits stack
09:03 The hidden cost of employee turnover
12:43 The psychology behind saving behavior
15:03 Real employee success stories and impact
24:22 Why financial engagement is changing in the workforce
26:01 How storytelling helped Sunny Day Fund grow
28:23 Using social media and content to build awareness
30:31 The role of banks and credit unions in the model
35:12 Fintech partnerships vs disintermediation
37:53 Advice for founders building in financial inclusion
45:31 Legislative momentum and the future of emergency savings

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Key Topics Discussed
• Emergency savings as an employee benefit
• Financial stress in the workforce
• Financial wellness programs that actually work
• Payroll-deducted savings accounts
• Employer-matched emergency savings
• Retention and employee engagement
• Fintech partnerships with banks and credit unions
• Financial inclusion and economic mobility
• The future of workplace financial benefits

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About Sunny Day Fund

Sunny Day Fund is a fintech platform that helps employers offer emergency savings accounts through payroll deduction. By combining employer incentives with automated savings, the platform helps employees build financial resilience while helping organizations improve retention and engagement.

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Connect

Follow Rachel Fox on LinkedIn
Learn more about Sunny Day Fund

Subscribe for more conversations with leaders across fintech, banking, and financial innovation.

Want to work with Propagate Fintech? Fill out a contact form at www.propagatefintech.com

What actually drives digital transformation in banking?

In this episode of the Propagate Fintech Podcast, Roland Howard sits down with Justin Dunmyer of ICBA to unpack what community banks, fintech founders, and banking leaders often get wrong about innovation, automation, and data strategy.

Justin previously spent over a decade inside a community bank working his way from teller to Chief Digital Officer, leading digital strategy, analytics, partnerships, and marketing. Today he works with the ICBA ThinkTECH Accelerator, helping fintech companies connect with community banks across the United States.

This conversation cuts through the buzzwords around AI, fintech, and banking innovation to focus on what actually works.

If you’re a fintech founder, banking executive, or fintech operator, this episode explains:

• Why most digital transformation initiatives stall

• How banks should start with automation and data

• What fintech founders must understand before selling to banks

• How the ICBA fintech accelerator works

• Why community banks may be uniquely positioned for the AI era

• Why digital transformation is more about culture than technology
• The most common mistakes banks make when adopting fintech
• How automation should start inside community banks
• Simple ways banks can use data without hiring data scientists
• Why fintech founders struggle to sell into banks
• What makes a fintech truly bank-ready
• How the ICBA ThinkTECH Accelerator connects fintechs with banks
• Why AI may strengthen community banking relationships rather than replace them

Timestamps

0:00 From Community Banking to Fintech Innovation

0:48 Community Bank Career Journey: Teller → Chief Digital Officer

2:16 What Digital Transformation in Banking Really Means

3:20 Why Digital Transformation Often Fails

4:34 Building a Culture of Innovation in Banks

5:54 Quick Wins for Banking Transformation

7:03 Customer Onboarding and Digital Banking Adoption

7:31 Why Innovation Projects Stall in Banks

9:00 Change Management in Financial Institutions

9:51 Avoiding Death by Committee in Tech Decisions

10:29 Chief Digital Officer vs CIO vs CTO

12:16 Building the Business Case for Technology

13:36 Where Community Banks Should Start with Automation

15:02 Why Data Is a Bank’s Most Valuable Asset

17:17 Practical Data Use Cases in Banking

18:09 Avoiding Analysis Paralysis with Data

20:40 Mentorship and Career Growth in Banking

21:37 What ICBA Does for Community Banks

22:32 Inside the ICBA ThinkTECH Accelerator

24:13 How Fintechs Get Real Feedback from Bankers

25:35 Why the Accelerator Matters for Fintech Distribution

26:06 How ICBA Selects Fintech Companies

27:55 What Makes a Fintech “Bank Ready”

32:27 Why Selling to Banks Is So Hard

34:48 Biggest Mistakes Fintech Founders Make

37:03 How Banks Actually Evaluate Vendors

37:38 Partnerships and Fintech Distribution Strategy

39:37 AI in Banking: The Next 3–5 Years

42:42 Why Community Banks May Win the AI Era

44:21 Advice for Community Bank CEOs

45:11 Advice for Fintech Founders

46:32 ICBA Innovation Programs and Accelerator

47:58 Closing

Want to work with Propagate Fintech? Fill out a contact form at www.propagatefintech.com