In this episode of The Grit Mindset, host Matt Rosen sits down with entrepreneur and investor Ray Larson. Ray shares how he built his career from launching a print management company to running a family office today. He opens up about the challenges he faced early on, the tough pivot from print to search, and the realization that he needed to reinvent his IT shop to keep moving forward. Along the way, Ray reflects on whether he always knew he wanted to be an entrepreneur and what keeps him driven.

This conversation is all about grit, perseverance, and the hard-earned lessons that come with building and rebuilding in business.

Stay Gritty!

From boy scout to Green Beret, Daniel Elkins has dedicated his life to service. As the Founder and President of the Special Operations Association of America (SOAA), Daniel created the organization to fill a critical gap—advocating for Special Operations Forces (SOF) and their families in the halls of power on Capitol Hill.
In this conversation with host Matt Rosen, Daniel opens up about:
-The unique challenges he faced as a Green Beret and why SOAA was born to give SOF veterans a voice in policy and legislation.
-His early dream of military service and path through the National Guard.
-The fall of Afghanistan, his first combat experiences, and the life-changing moment when he thought his career might be over.
-The impact of watching a fellow soldier survive being shot, and the mindset shift that led him to adopt his “be a shark, keep moving forward” mantra.
-What grit truly means to him—from combat zones to tough advocacy decisions, including the harrowing moment of helping choose who would live and who would die during interpreter evacuations.
-The challenges of transitioning from military life and why building SOAA was essential for the future of the SOF community.

👉 Watch as Daniel shares his story of resilience, leadership, and grit—on and off the battlefield.

🔗 Learn more about Daniel and SOAA: soaa.org
Timecodes:
00:10- 4:30: Special Operations Association started by Daniel Elkins, Daniel Elkins is the Founder and President of SOAA, He is a Green Beret and has served in Special Operations roles
When he became a green beret he shares unique challenges he had on advocacy for veterans
There was a huge gap under represented, SOAA was created to give a voice to Special Operations Forces (SOF) in the domain of policy and legislative affairs
4:30 Daniel shares as a young boy he wanted to be in the military and why he chose the national guard. He was in boy scouts and loved being in the woods and ultimately he wanted to serve his country.
8:30 Host Matt Rosen asks Daniel about challenging times he has endured in his life as a green beret. Daniel shares about the fall of Afghanistan and his first real experience in combat
12:14 Daniel shares when he thought his career was over and had a difficult decision to make to talk to his Sergeant.
14:09 Daniel shares the rest of his deployment and the repercussions he faced
15:00 Daniel shares when his friend was shot in the face and survived and how it effected Daniel with how to have a mantra and mindset of being a shark and not being a failure and moving forward
16:30 Matt asks what does grit mean to Daniel
20:00 Daniel shares remembering getting a call from a prominent member from Capitol Hill crying with the interpreters and making decisions for who would live and who would die
23:00 Host Matt Rosen asks what the challenges have been for Daniel starting Special Operations Association, he shares the day you take your uniform off what happens after a military career

https://soaa.org/team/daniel-elkins/
Daniel is the Founder and President of the Special Operations Association of America (SOAA), a Green Beret, a graduate of the Harvard Kennedy School of Government, and a member of the Atlantic Council’s Counterterrorism Project.

What does it take to step into the CEO seat—and stay there?

In Episode 29, host Matt Rosen sits down with Mark Sinatra to unpack the grit behind leadership. Mark reflects on when he first knew he wanted to be a CEO, the types of businesses he gravitated toward, and the hard truth that finding people who share your vision is rare. His advice? When you find those people—keep them.

Matt pushes the conversation deeper, asking Mark to share his most challenging leadership story. Mark opens up about building culture and relationships inside a remote company. While remote work has its advantages, fostering connection and alignment from a distance has been his toughest challenge yet.

At the heart of their discussion is what it means to embrace The Gritty Mindset: keeping an open mind, avoiding defensiveness, asking for help when needed, and creating a culture where leaders and team members alike feel safe to show vulnerability.

It’s a powerful reminder that grit isn’t just about pushing through—it’s about building trust, connection, and resilience in the face of challenges.

In this inspiring episode, Matt Rosen sits down with Sunny Vanderbeck, entrepreneur, investor, Army veteran, and author of Selling Without Selling Out. Sunny takes us on a journey of resilience, grit, and the lessons learned from building and rebuilding companies.

From starting college at 16, earning an engineering degree, serving in the U.S. Army, and launching his first company in his 20s—Sunny’s path is anything but ordinary. He candidly shares the highs and lows of entrepreneurship: selling his business, facing a devastating setback, and ultimately buying his company back after bankruptcy.

Sunny reflects on how grit—simply just keeping going—carried him and his team through uncertain times. He opens up about the importance of empathy, leadership under pressure, and breaking down vs. breaking through. Along the way, he shares stories of lessons learned at Compaq, the impact of 9/11, and how he built his next venture, Satori Capital, over a meal at Chili’s with a vision to reshape the future.

Key Highlights:

• 🎓 Started college at 16, Army service, and first entrepreneurial ventures

• 📠 The fax machine story and a major business setback

• 💪 What “grit” means in entrepreneurship and leadership

• 🌍 Building Satori Capital and its purpose-driven origin

• 🥂 The “Gratitude Dinner” tradition

• 📖 Author of Selling Without Selling Out, helping entrepreneurs exit with integrity

Sunny’s journey is proof that setbacks don’t define you—your grit does.

🔗 Learn more about Sunny and Satori Capital: satoricapital.com
📘 Get his book Selling Without Selling Out: Amazon link

Stay Gritty!

In this episode of The Grit Mindset, host Matt Rosen sits down with longtime friend and former co worker Vimal Vachani, founder of Crex Software—a SaaS company revolutionizing real estate technology. From his early passion for data and analytics to building software that now serves the entire real estate vertical, Vimal shares how Crex empowers property managers whether they oversee 10 buildings or 1,000+.

Vimal opens up about his journey as a first-generation American entrepreneur, the two-year grind of putting pen to paper before launching Crex, and the challenges of starting a company just as COVID hit New York City. He recalls the reassurance of landing his first client, the balancing act of becoming a dad while running a startup, and the perseverance it takes to push through tough times with grit and hustle.

With honesty and humor, Vimal admits: “Had someone told me how hard this would be, I don’t know if I would have done it.” But his story is proof that grit, family, and an unshakable belief in data’s power can build something truly impactful.

🚀 On this episode of The Grit Mindset, Matt Rosen sits down with entrepreneur Chaitan Fahnestock, founder of Sportsmo, the “gamified giving” app changing how fans support their teams. From growing up in Wichita and working in the family heating & air business to building a his own companies, Chaitan shares his biggest lessons, setbacks, and what grit really means to him. 💪 Discover how patience, tenacity, and the love of building led him to launch Sportsmo.
Stay Gritty!

Timestamps:
0:00 Intro
0:30 Matt intros Chaitan Fahnestock the founder of Sportsmo
1:00 What is Sportsmo explainer "it is gamified giving"
1:30 Examples of the Sportsmo app and how to use it play by play
2:30 Host Matt Rosen is ready with rooting on his Aggies!
2:45 With Oklahoma State in mind, Chaitan was problem solving in his own mind with Universities calling on their wealthiest donors to be successful. Chaitan says this is the "easy" button
4:00 Host Matt Rosen asks "What led you down the path through your life to become an entrepreneur"
4:10 Chaitan grew up in Wichita Kansas and he had a desire to take a high school entrepreneur class and it got his wheels turning of what could be
6:00 Chaitan was a worker at an early age! He worked in heating and air, golf corse, restaurant and a family business Fahnestock Heating and Air
6:30 Fahnestock Heating and Air details working for family and how one particular summer taught him what he didn't want to do.
7:15 Chaitan's College days at Oklahoma State, minor in French and major in Accounting.. happily falling into accounting.
8:00 Ernst & Young (EY) was his first firm, he describes being on site with clients and the excitement of this real world experience as a young man in business for 5 years
10:00 Chaitan's Accounting to Sales story, managing teams and he shares the skills that were different with rolling up his sleeves.
11:30 The changing business landscape
12:00 In 2005, Chaitan is approached to start a business and this was a wonderful decision. Chaitan had quite the journey building a company to 300 million!
13:00 Host Matt Rosen asks Chaitan about his greatest adversities he has faced in business. Chaitan shares moments of grit from the earliest days such as collecting invoices to make payroll. Growing pains as a small company are much different from the larger company problems. Chaitan shares moments of everyone getting checks and illustrates angst in digging the company out of the earth with blood sweat and tears.
14:58 Chaitan shares a story about recruiting faster than selling and becoming overstaffed. This was a business issue that caused pain and suffering for Chaitan. Business growth was put on hold and this was not his favorite chapter of his story.
16:00 Matt asks what Chaitan would "do over" and Chaitan shares he would have tapped the breaks on hiring and would have avoided this pain all together however his perspective is
17:00 Host Matt Rosen asks his famous question: What does Grit mean to you? Chaitan's response is heartwarming about his daughter's team is named Grit. He shares his personal perspective on grit means patience and tenacity.
18:00 Matt asks Chaitan what adventure he is on now in business, Chaitan shares there was some freedom however he is not built to play golf everyday. He loves the beach but he has aspirations of building.... and that is why he started the Sportsmo app!
20:00-25:00 Matt asks Chaitan about his personal hobbies. Chaitan surprises us with mountain climbing! He has climbed the snow capped mountain of Mt. Rainier. He shares an incredible story about the challenges along the way of hiking and climbing a variety of mountains like Mount Kilimanjaro which was 6 nights on the mountain along with the journey to get there. "You get to learn more about yourself than you thought you needed to know"
25:00 Chaitan has a revelation about the adventure of the climb and he starts thinking about the first Fahnestock from the 1700's and the grit to get to America. He has flashes from his past and the grit of his parents who he says are the ultra adventurers. He shares where his name came from.
27:35 Matt asks in closing Chaitan's words of advice to listeners, Chaitan says "do your homework but JUST DO IT"

In this episode of The Grit Mindset, Matt Rosen welcomes Eli Goldaris, Managing Director at Isagani Yorke Capital Partners. With years of experience guiding businesses through complex deals, Eli has built a reputation for helping owners position their companies for growth and long-term success as a seasoned entrepreneur.

Eli shares why so many businesses and M&A deals fall apart, what strategic buyers are really looking for, and how his firm supports companies through these high-stakes transitions. He also opens up about his personal journey into entrepreneurship—why questioning whether you should be an entrepreneur usually means it’s not for you, and the defining moment he knew he had to take the leap.

In a powerful story, Eli recalls leaving his corporate role to start his own company—only to suffer a stroke two weeks later—and how that life-altering experience reshaped his mindset, resilience, and commitment to forging his own path. Matt and Eli also dive into the biggest challenges entrepreneurs face today and how politics ripple through the economy, impacting business strategy and deal-making at every level.

In this episode of The Grit Mindset, Matt Rosen takes us back to 2002, when the tech bubble burst and he traded IT sales for bar ownership in Dallas’ Lower Greenville. He shares the wild ride of opening Dirty Daves—from build-out headaches, parking problems, and too many free drinks… to debt before opening day, missing daiquiri machines, and hiring the DJ as manager.

Matt gets real about the mistakes, the lessons learned, and how those early challenges shaped his move into consulting. Along the way, he reflects on working with his brother, why personal guarantees can be risky, and the dos and don’ts of going into business with friends. It’s an honest, entertaining, and educational look at grit, risk, and finding the silver lining when things don’t go as planned.