Steve Negri has started four fintech companies, sold one to Jack Henry, and helped build the modern payments rails most of us use every day. But in 2025, after burying his best friend of 38 years, everything looks different.

This is the most honest founder interview we’ve ever recorded.

You’ll hear:

• Why “doing everything right” is no guarantee of success
• The moment he realized he was raising money from family 401(k)s during the 2008 crash
• How death at 50 rewrote his definition of winning
• The daily habits that keep a 30-year fintech veteran sharp
• Why community banks are about to beat the giants (and how Next Moves is making it happen)
• The uncomfortable truth about getting “comfortable being uncomfortable”
• His non-negotiables: integrity, long-term friendships, and never forgetting who believed in you first

I

f you’ve ever wondered what entrepreneurship actually costs when the confetti settles, this is the episode.

Connect with Steve & Next Moves: Website → https://nxt-moves.io

LinkedIn → Steve Negri

If this one hit you, share it with one founder who needs the reminder that relationships > revenue.

00:00 – Intro: Four exits, one heartbreaking year 01:04 – From corporate sales to four-time founder 02:55 – The mentors who turned a 22-year-old into a sales monster 05:53 – Why “sell yourself first” is still the only rule that matters 07:52 – The moment he knew corporate wasn’t for him 10:29 – Raising money from family 401(k)s during 2008 – the real founding story 15:10 – “You can do everything right and still fail” – the lesson age teaches 16:48 – It takes a village: why founders who go alone usually lose 19:02 – Daily habits of a 50-year-old founder who refuses to slow down 21:57 – The evolution of fintech from “financial technology” to trillion-dollar industry 25:26 – The origin of Next Moves (and why the rook is the chess piece) 28:20 – Why Gen-Z wants experiential rewards, not points 33:28 – AI in payments: what’s real vs. hype in 2025–2026 35:14 – Losing his best friend at 50 – the conversation that changed everything 41:07 – Final words: integrity, reinvention, and never retiring

Steve Negri, Next Moves fintech, fintech founder interview, founder grief, losing best friend at 50, fintech journey, payments innovation, community banking 2025, founder mortality, entrepreneurship cost, relationships vs revenue, 4x exited founder, fintech exits, death and entrepreneurship, founder mental health, experiential rewards, Gen Z credit cards, raising money 2008, founder integrity

Drop this in and watch it become one of your most shared episodes of the year. This is the one people will still be texting their friends about in 2027.

Summary

In this engaging conversation, Randy Tate, CEO and co-founder of iFlip, shares his remarkable journey from a farm in Northern California to leading a fintech revolution with AI-driven investing. He discusses the values instilled in him from his upbringing, the challenges and triumphs of entrepreneurship, and the innovative approach iFlip takes to democratize investing. Randy emphasizes the importance of leadership, team culture, and the impact of AI in transforming wealth management, all while advocating for a future where everyone has the opportunity to grow their wealth.

Keywords

Randy Tate, iFlip, fintech, AI investing, entrepreneurship, leadership, wealth management, problem solving, team culture, financial services

Takeaways

Randy's upbringing on a farm instilled values of grit and resilience.

Transitioning from teaching to entrepreneurship was driven by a desire to solve problems.

iFlip aims to make investing smarter and more accessible through AI.

AI in investing can adapt and learn, unlike traditional algorithms.

The importance of minimizing losses in investing is crucial for long-term success.

Leadership requires a like-minded team and the ability to disagree and commit.

Randy emphasizes the need for open communication within teams.

The future of iFlip includes expanding services for independent advisors and small businesses.

Randy believes in the power of entrepreneurship to create positive change.

He wants to be remembered for helping others and promoting opportunity.

Titles

From Farm to Fintech: Randy Tate's Inspiring Journey

Revolutionizing Investing: The iFlip Story

Sound bites

"We stepped out of the market."

"Missing the downs is far more important."

"This country is about free opportunity."

Chapters

00:00 From Farm to Fintech: Randy's Journey

02:57 The Values of Grit and Resilience

05:44 The Leap into Entrepreneurship

08:40 The Birth of iFlip: Solving Investment Problems

11:40 AI in Investing: A Game Changer

14:39 Understanding the Algorithm: AI vs. Traditional Methods

17:40 The Future of Investing: Direct to Consumer Model

20:29 Breaking Down Barriers: Affordable Investment Solutions

26:14 The Role of AI in Investment Strategies

29:51 Leadership Lessons from Coaching

35:19 The Importance of Mentorship

38:26 Future Aspirations for iFlip

43:08 Advice to My Younger Self

44:36 Legacy and Impact on Society

Desert Storm veteran Robert R. Wilson grew up in the shadow of his WWII Ranger father (Omaha Beach). Today he runs R2C — a 140-person defense-tech powerhouse that still moves at battlefield speed to save American lives.

From the beaches of Normandy (his father’s D-Day landing) to the sands of Desert Storm and now leading one of America’s most respected veteran-owned defense contractors — Robert R. Wilson reveals the non-negotiable principles that took him from enlisted soldier to CEO.

In this powerful episode you’ll discover:

• How a napkin sketch in Afghanistan saved dozens of Black Hawks (and lives) in under 75 hours
• Why he tells every employee R2C is only their #4 priority (God, family, country come first)
• The leadership secret he stole from the best officers: “Tell capable people WHAT, clear obstacles, then get out of the way”
• How defense contractors have been using AI for target recognition and rapid prototyping for 15+ years (long before ChatGPT)
• Why “get up, suit up, show up” wins 85 % of every battle — in war or business
• The mindset shift every person under 30 needs if they’re going to live to 150
• His personal motto: “Work like it all depends on you; pray like it all depends on God”

This is patriotism, leadership, and legacy at the highest level.

Connect with Robert & R2C: Website → https://www.r2c-inc.com LinkedIn → Search “Robert R. Wilson R2C”

If this episode moved you, share it with one leader who still believes in service over self.

00:00 – Intro: A legacy born on Omaha Beach 01:03 – Growing up the son of a WWII Ranger (Saving Private Ryan connection) 02:53 – Desert Storm lessons that still drive R2C today 04:30 – The napkin sketch that saved Black Hawks in Afghanistan (75-hour miracle) 07:29 – Why he left corporate to start R2C: “God’s plan beats my plan” 10:14 – The only 4 priorities he allows employees to have 12:17 – Why Space Force was inevitable (and critical) 14:24 – How to scale to 140 people without killing family culture 16:40 – Best leadership advice from an NCO: empower, delegate, get out of the way 19:35 – Defense contractors have been using AI for 15+ years (the real story) 24:22 – Staying grounded: God, family, country, work — in that order 26:06 – Who Robert Wilson is when you strip away the titles 27:34 – Best book + mindset advice: “Get rid of the stinkin’ thinkin’” 29:44 – His two life mottos (you’ll quote these forever) 32:20 – Advice to the next generation: Plan for 100+ years of life & contribution 38:45 – Legacy, closing thoughts & how to connect 41:07 – Outro

Robert Wilson, R2C Inc, Desert Storm veteran, Omaha Beach, WWII Ranger legacy, defense contractor, veteran owned business, military leadership, defense tech, AI in defense, Space Force, Black Hawk Afghanistan story, veteran entrepreneur, patriotic leadership, service before self, God family country work, Huntsville Alabama defense, rapid prototyping defense, AI in defense, leadership lessons from war

40-year supply-chain titan (UPS → Walmart → billions transformed) left corporate to fix humanitarian logistics full-time. Now building “Angelic Intelligence” AI that asks “should we?” before “can we?”

Steve Robinson spent four decades mastering global supply chains — starting on the warehouse floor at UPS in 1976 and eventually running transformations worth billions at Walmart.

Then he quit everything to dedicate 100 % of his life to one mission: closing the gap between peak waste and peak need in humanitarian aid.

This is the rare conversation that combines world-class operational mastery with profound moral purpose.

You’ll discover:

• How UPS in the 1970s taught him “details decide everything”
• The untold story of building Walmart’s legendary supply-chain machine
• Why supply chains are living ecosystems, not just pipelines
• The napkin-to-reality story that saved lives are still being saved by today
• Introducing “Angelic Intelligence” – AI that doesn’t just solve problems… it asks whether we should
• The one question he wants every leader to answer: “What do they say about you at your funeral?”
• Why the world is simultaneously at peak food waste and peak hunger — and how he’s fixing it
• The Supply Chain Project: 100 % nonprofit, 100 % focused on humanitarian efficiency

If you’ve ever wondered what a life of total alignment looks like when the titles and money no longer matter — this is it.

Connect with Steve & The Supply Chain Project Website → https://thesupplychainproject.org LinkedIn → Steve Robinson / The Supply Chain Project Email → [email protected]

If this episode moved you, share it with one leader who still believes profit and purpose can coexist.

00:00 – Intro: From UPS loading dock to global impact 00:56 – 1976 UPS: Standing 4 hours for a seasonal job & learning “details matter” 02:10 – Supply chains as living ecosystems (not pipelines) 04:30 – Inside Walmart’s legendary machine – the untold stories 07:15 – The moment he couldn’t unsee: peak waste + peak need 10:45 – Why he walked away from corporate glory 14:20 – The Supply Chain Project: 100 % humanitarian, zero ego 18:40 – Real stories from disaster zones – where minutes save lives 22:30 – Introducing “Angelic Intelligence” – AI that asks moral questions first 28:10 – “Nobody talks about your balance sheet at your funeral” 32:45 – The one leadership principle that survived 40 years 36:00 – Legacy talk: What he wants said when he’s gone 40:47 – How to get involved & final words 41:35 – Outro

Steve Robinson, Walmart supply chain, UPS veteran, humanitarian supply chain, world hunger solutions, Angelic Intelligence, AI ethics, supply chain waste, global logistics, disaster relief, purpose driven leadership, nonprofit supply chain, peak waste peak need, legacy leadership, operational excellence, corporate to nonprofit pivot