Business Unchained

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Fill out the form and be one of the 50 listeners who can get a FREE copy of Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance: https://bobbymascia.com/reach-out-and-connect/. Here’s how: Comment Unchained and add your address in the MESSAGE field. Open to those residing in the continental United States only.

Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD

Reference Links: 

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Episode Highlights

Business Unchained is taking a short recording break for the summer, with a new season returning in late fall. Before stepping away, Bobby Mascia has a special gift for entrepreneurs, family business owners, and loyal listeners.

In this special episode, Bobby explains how leaving Wall Street to join his family’s Dunkin’ Donuts franchise business exposed him to toxic workplace culture, family business conflict, and the dangers of becoming the bottleneck in your own company. After walking away and rebuilding from scratch, he created a wealth management firm and a practical business playbook for entrepreneurs who want to build companies that work for them, not the other way around.

“If you can’t step away from your business without everything falling apart, you didn’t build a company, you built a job.” – Bobby Mascia [01:50]

Built a successful business but feel trapped inside it? Bobby is giving the first 50 eligible listeners a free copy of Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance. The book is a practical playbook for entrepreneurs who want to stop being the bottleneck, navigate family business conflict, and build a company that creates freedom instead of consuming their life.

The giveaway is available to listeners in the continental United States. Click the link at the top of the show notes, submit your name and shipping address, and include the word “Unchained” to claim your copy before all 50 are gone.

“Unchained is my story, but it’s also a playbook. I’m not giving you theories. I’m giving you what I learned bleeding, building, failing, and getting back up.” – Bobby Mascia [02:27]

In This Episode

• [00:00] – Introduction
• [01:12] – Business Unchained’s summer recording break
• [01:50] – The danger of building a job instead of a company
• [02:08] – Walking away from a toxic family business
• [02:27] – Building wealth and businesses that serve the owner
• [02:59] – How to request a free copy of Unchained

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About Jeff Savlov

Jeff is a trusted advisor to business families, families with legacy wealth, and entrepreneurs navigating moments of transition. He helps them strengthen family relationships, prepare rising generations, and build the emotional and structural foundations that allow both the family and the enterprise to thrive over time.

Drawing on his background in his own family’s commercial printing business, years in sales and marketing, and clinical training as a family therapist and psychoanalyst, Jeff brings a rare blend of strategic insight and psychological depth. His work sits at the intersection of family dynamics, leadership development, and long-term stewardship.

He is especially known for helping parents raise grounded, capable children in the context of wealth, and for guiding families through the complex emotional terrain that accompanies succession, ownership transitions, and shared decision-making.

At the heart of Jeff’s approach is a belief that healthy relationships are the most durable form of wealth — and that with the right support, families can turn transitions into opportunities for connection, clarity, and continuity.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Jeff Savlov

• LinkedIn
• Website

Episode Highlights

In this episode of Business Unchained, Bobby Mascia sits down with Jeff Savlov, a family business and family wealth consultant, to unpack one of the biggest challenges successful entrepreneurs face: how to pass down wealth, ownership, values, and opportunity without creating a sense of entitlement. Jeff shares practical insights on family business succession planning, raising responsible children in wealthy families, building a work ethic in the next generation, and why family wealth should strengthen a family rather than quietly damage it.

“Optimal frustration means a parent's job is to make life the right amount of challenging and frustrating for a kid. It's not to make it as easy as possible.” – Jeff Savlov [10:48]

Bobby and Jeff explore what separates families that successfully transition a family business from one generation to the next from those that fall apart under poor communication, unclear expectations, and unearned roles. They discuss why children should often work outside the family business before coming in, how to avoid giving the next generation responsibility they have not earned, and why family governance, meritocracy, advisory boards, and honest conversations are essential for long-term family business survival.

“It's about being intentional about giving kids those experiences.” – Jeff Savlov [39:13]

This conversation is a must-listen for entrepreneurs, business owners, wealth creators, and family business leaders thinking about legacy planning, succession, raising non-entitled kids, and preparing the next generation for ownership. Jeff also shares his personal story of growing up around a family business, how therapy changed the course of his family, and why the most successful families do not wait for conflict to explode before talking about money, values, leadership, and the future.

“Families need governance. How do we pick leaders? How do we distribute ownership? What are the rights of owners?” – Jeff Savlov [51:21]

In This Episode

• [00:00] Introduction
• [01:38] Why Jeff’s work is not just about “fighting families”
• [04:29] Proactive vs. reactive conversations around family wealth
• [05:36] The Purposeful Legacy Family Project
• [06:56] Teaching kids values before teaching them about money
• [07:50] How good intentions can create entitlement
• [10:48] Why “optimal frustration” matters in raising responsible kids
• [12:57] Teaching children accountability through real-life consequences
• [14:23] Why the next generation should work outside the family business first
• [17:01] The danger of giving family members roles they have not earned
• [18:40] What happens when family wealth planning is proactive instead of reactive
• [21:57] Why expectations must be clear before kids enter the family business
• [24:39] Warning signs that family conflict is threatening the business
• [26:13] How advisory boards and outside advisors can help family businesses
• [28:40] What to do when the “chosen” successor is in the wrong seat
• [30:24] Bobby’s honest question about whether his kids should join his business
• [33:33] Family business conversation starters for kids and parents
• [35:16] How to build hunger, hustle, and gratitude in wealthy families
• [39:21] Balancing luxury, privilege, and real-world perspective
• [44:02] Why family business survival statistics do not tell the full story
• [47:25] Building a family culture that lasts beyond one generation
• [49:30] How prenups and married-in family members complicate family wealth
• [50:52] Conflict, meritocracy, and governance in family-owned businesses
• [52:03] Knowing which “hat” you are wearing: parent, owner, leader, or trustee
• [53:49] Jeff’s personal story and what led him into family business consulting
• [58:09] Why entitlement is not only a wealthy-family problem
• [60:00] Where to find Jeff Savlov

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About David Genova

David Genova is the Founder and Principal of Greenwood Development, a community-focused real estate development company behind nearly 20 redevelopment projects in Montclair, New Jersey, and the surrounding area. With a career rooted in adaptive reuse, downtown revitalization, mixed-use development, and neighborhood-first real estate strategy, David has built his business around one core idea: development should strengthen the community it serves.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

David Genova

• LinkedIn
• Instagram
• Website

Episode Highlights

In this episode of Business Unchained, Bobby Mascia sits down with David Genova to unpack the business of invigorating a town through thoughtful real estate development, local economic growth, and long-term community investment. David shares how his early internships at Jones Lang LaSalle and a Jersey City family office shaped his love for deal-making, urban development, and building projects that last for generations. From there, he explains why Montclair became his “product type” and how local knowledge, patience, reputation, and community trust can give developers an edge that big capital alone cannot buy.

“My product type is Montclair. My product type is community and the community behind Montclair.” – David Genova [14:35]

David also breaks down the redevelopment of the iconic Wellmont Theatre, the strategy behind using arts and entertainment as an anchor for downtown Montclair, and why adaptive reuse can be one of the smartest ways to bring old buildings back to life. He shares honest lessons on real estate partnerships, project-by-project financing, gaining community support for development projects, navigating zoning challenges, and balancing profitability with responsibility when building in the town you call home.

“When you communicate with people, it’s a lot harder to get angry at them.” – David Genova [31:10]

This conversation is a practical and thoughtful look at what it takes to build a real estate development business that is not just focused on maximizing returns, but on creating sustainable community growth. David reflects on Montclair’s changing demographics, the tension between revitalization and gentrification, and how success for him means leaving the town better than he found it while preserving the culture, creativity, and weirdness that made people want to be there in the first place.

In This Episode

• [00:00] – Introduction
• [02:10] – David Genova’s entrepreneurial mindset and early career path
• [05:19] – Why real estate development became David’s passion
• [08:09] – What makes Montclair, New Jersey a unique redevelopment market
• [12:14] – The early revitalization of the Wellmont Theatre
• [14:35] – Why David’s product type is community, not buildings
• [16:18] – Adaptive reuse and giving old buildings a second life
• [18:12] – Using the Wellmont Theatre to help revive downtown Montclair
• [20:03] – How David builds a wishlist of future real estate opportunities
• [24:18] – Funding development projects one deal at a time
• [25:36] – What makes a good real estate investment partner
• [29:47] – How developers can gain community support early
• [31:47] – The swim school project and working with local stakeholders
• [36:06] – Navigating zoning, parking, and historic district challenges
• [42:23] – Reflecting on gentrification and community responsibility
• [46:05] – Preserving the culture and character of Montclair
• [48:08] – How David defines long-term success as a developer
• [50:02] – Why outside investors need local knowledge to succeed

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About Elina Greenstein

Elina Greenstein is an entrepreneur, technology strategist, cybersecurity advisor, and business owner who spent nearly two decades in corporate technology and B2B sales leadership before leaving the traditional “safe” corporate path to build her own business. Today, as a CMIT franchise owner, Elina helps growing companies strengthen their IT infrastructure, reduce cybersecurity risk, improve operational security, and build more scalable, less owner-dependent businesses.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Elina Greenstein

• LinkedIn
• Website

Episode Highlights

In this episode of Business Unchained, Bobby Mascia sits down with Elina Greenstein to unpack why the traditional corporate career path no longer guarantees stability, freedom, or long-term financial security. After years of climbing the corporate ladder, earning strong performance reviews, and building a successful career in tech, Elina realized she was trading too much time away from her family for a system where the goalpost reset every year. Her story is a powerful conversation for corporate professionals, executives, and business owners thinking about entrepreneurship, franchise ownership, work-life balance, and building an asset that compounds beyond a paycheck.

“I spent almost two decades doing the safe thing, the thing that everybody expected you to do.” – Elina [02:00]

Bobby and Elina also dig into the business side of technology strategy, cybersecurity for small businesses, managed IT services, operational risk, AI-driven cyber threats, and how weak technology infrastructure can quietly hurt business valuation. Elina explains why growing companies need repeatable systems, clear IT ownership, cybersecurity processes, and scalable operational structures long before they are ready to sell. From outsourced CIO support to cyber insurance readiness, device management, phishing scams, and exit readiness, this episode shows why technology is no longer just “the guy with the cords” fixing Wi-Fi; it is a critical driver of business growth, risk management, and enterprise value.

“Strong technology and operational security builds valuations rather than just being another line item.” – Elina [25:18]

This conversation is also about redefining success. Elina shares how becoming a business owner changed the way she thinks about income, family, time, risk, and legacy. Instead of asking how to replace a corporate salary, she reframed the question around how to build a valuable business asset, create more control over her time, and design a life where her work is visible to the people who matter most.

“What seems to be stable can actually have hidden risks.” – Elina [50:39]

In This Episode

• [00:00] – Introduction
• [02:00] – Why Elina left the “safe” corporate path after nearly two decades
• [06:02] – Growing up with immigrant parents and the pressure to follow the traditional path
• [10:49] – How Elina discovered franchise ownership beyond restaurants
• [13:16] – The “killer question” to ask when evaluating a franchise opportunity
• [14:31] – Why Elina chose technology, cybersecurity, and managed IT services
• [16:48] – What growing businesses actually need from an IT and cybersecurity partner
• [18:12] – Why IT infrastructure is more than tech support
• [22:24] – Why AI will make scams, phishing, and voice fraud more dangerous
• [24:41] – How structure creates clarity, consistency, and business value
• [27:06] – Why scalable businesses cannot depend on one owner or one person
• [28:33] – How Elina’s kids changed her definition of ego and success
• [31:52] – The biggest challenges in educating business owners about modern IT risk
• [35:04] – Why the highest-value work still has to come from humans
• [41:35] – How Elina had to unlearn the W-2 mindset around money and investing
• [45:00] – Why building a business asset is different from replacing a corporate salary
• [48:30] – Why staying still in corporate can become its own hidden risk
• [50:39] – Elina’s top three lessons for business owners and professionals
• [52:11] – Why not every client is worth taking
• [54:17] – Building family discipline by choosing time with your kids
• [56:34] – Final thoughts on corporate life, entrepreneurship, and taking control

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About Kevin St. Clergy

Kevin St. Clergy is the author and founder of Blind Blaming, a business coach, speaker, mastermind leader, and entrepreneur who achieved an eight-figure exit in 2022. After building and selling a successful digital marketing company serving audiology practices, Kevin turned his focus toward helping business owners identify the real root causes behind stalled growth, leadership frustration, team dysfunction, burnout, and recurring business problems.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Kevin St. Clergy

• Beyond Blind Blaming Book
• Website
• LinkedIn

Episode Highlights

In this episode of Business Unchained, Bobby Mascia sits down with Kevin St. Clergy, author and founder of Blind Blaming, to unpack why so many business owners stay stuck by fixing the wrong problem. Kevin shares the personal story that shaped his framework, from being blamed as a kid for poor performance in baseball to later discovering he simply needed glasses. That experience became the foundation for helping entrepreneurs identify hidden blind spots in leadership, mindset, health, team performance, marketing, sales, and business growth.

“The adults in my life never stopped blaming me for something that was out of my control.” – Kevin St. Clergy [04:46]

Kevin breaks down how blind blaming shows up when founders assume the issue is marketing, employees, motivation, or organization, without diagnosing the real root cause. Through his RCD Method, Reflect, Connect, and Decide, he explains how entrepreneurs can step outside their own perspective, use coaching and masterminds to see what they cannot see alone, and make stronger decisions that move the business forward. This episode is a must-listen for business owners who want to build a company that does not depend entirely on them while improving leadership, culture, decision-making, and long-term growth.

“If you want something different, you have to do something different.” – Kevin St. Clergy [27:46]

In This Episode

• [00:00] Introduction
• [02:11] The question Kevin faced after selling his business: “What’s next?”
• [03:30] The childhood baseball story that inspired Blind Blaming
• [04:46] How being blamed for the wrong problem created years of self-doubt
• [10:52] The three fatal flaws that keep business owners stuck
• [12:04] Kevin’s RCD Method: Reflect, Connect, and Decide
• [15:18] Why business owners often sacrifice health while scaling their company
• [17:35] The power of taking breaks, protecting energy, and sharpening the saw
• [20:59] How Kevin structures mastermind groups to encourage vulnerability
• [26:40] Why “make a decision” means execution, focus, and follow-through
• [27:04] Why business owners need an outside perspective to diagnose blind spots
• [29:12] The danger of trying to make decisions on too many goals at once
• [32:27] What Kevin would tell himself before selling his company
• [38:48] Why great leaders should stop answering every question for their team
• [43:04] How Kevin’s definition of success shifted from money to balance to impact
• [46:24] Kevin’s take on imposter syndrome, ambition, and never quitting
• [48:50] Why people buy outcomes, not services
• [52:20] Where to find Kevin St. Clergy and Blind Blaming

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About Siamak Namazi

Siamak Namazi is a seasoned strategist with an MBA from London Business School, whose career spanning the private and nonprofit sectors was dramatically interrupted in 2015 when a four-day trip to visit family in Tehran turned into 2,898 days of captivity in Evin Prison—making him the longest-held American in Iran. Even in captivity, he never stopped problem-solving, turning every interrogation into a negotiation, building networks, and achieving historic firsts such as giving a landmark CNN interview to shine a light on the plight of hostages in Iran.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Siamak Namazi

• LinkedIn

Episode Highlights

In this episode of Business Unchained, host Bobby Mascia sits down with Siamak Namazi for a powerful conversation about leadership, resilience, and strategic decision-making under extreme uncertainty. Siamak shares how his life went from corporate strategy and business consulting in Dubai to solitary confinement in Iran, where he had to rely on mental frameworks, routines, humor, and decision models to survive years of captivity without losing his identity.

“Right now I'm trying to convey lessons about how to manage times of great uncertainty and how to make decisions when the world shifts from under your feet.” - Siamak Namazi [03:12]

Siamak breaks down the mindset shifts that helped him endure interrogations, false confession pressure, isolation, and the emotional weight of his father being imprisoned alongside him.

Siamak also shares how he used strategic risk assessment to conduct a historic CNN interview from inside an Iranian prison cell, helping bring global attention to his case before his eventual release.

“I decided to live the best life that I could regardless of the circumstances.” - Siamak Namazi [36:43]

For entrepreneurs, CEOs, business owners, and leaders navigating crisis, this episode offers a rare look at how to make better decisions when you have incomplete information, limited control, and everything feels stacked against you.

In This Episode

• [00:00] Introduction
• [02:06] Why Siamak's message matters for business leaders
• [03:12] Teaching corporations how to make decisions under uncertainty
• [04:17] How a four-day trip to Iran became eight years in captivity
• [05:10] The moment Siamak was stopped at the airport
• [07:07] Using humor during interrogations and high-pressure moments
• [13:35] Rebuilding his life after being held hostage
• [19:14] The beginning of solitary confinement and the pressure to confess
• [22:19] Understanding power, incentives, and information asymmetry
• [23:33] How Siamak became his own strategic consultant in prison
• [30:29] The strict routine that helped Siamak stay centered
• [32:27] The darkest moment of his captivity
• [39:05] How business decision models helped him survive extreme uncertainty
• [40:49] Seeing the best of humanity after experiencing the worst
• [41:46] The risk framework behind Siamak’s CNN interview from prison
• [42:55] Turning trauma into leadership lessons for business and life
• [43:28] Where to find Siamak Namazi

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About Phil Barone

Phil Barone is the founder and editor-in-chief of Wayne Lifestyle Magazine, a publication dedicated to showcasing the best of Wayne, New Jersey, and surrounding areas. With a passion for storytelling and community engagement, Phil has built the magazine into a go-to source for local culture, events, businesses, and inspiring individuals. Through his work, he highlights the stories that make the community unique, providing a platform for local businesses and personalities to shine.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Phil Barone

• LinkedIn
• Wayne Lifestyle Instagram
• Wayne Lifestyle Website

Episode Highlights

In this episode of Business Unchained, host Bobby Mascia sits down with Phil Barone, publisher of Wayne Lifestyle Magazine, to discuss resilience, creative marketing, and the power of empathy in business. Phil shares his incredible story of rebuilding his life after a traumatic accident and stepping in as a hero in a dangerous domestic dispute. He also reveals his unconventional marketing strategy of stepping into the ring for a professional wrestling match to promote his magazine, Wayne Lifestyle.

“You don’t have control over what happens, but you do have control over how you respond to it” - Phil [07:12]

Phil's journey is filled with ups and downs, including overcoming setbacks from a failed partnership and the challenges of launching a business during COVID. His story is a testament to perseverance, and his insights on how to build meaningful relationships and create a lasting impact in the community are truly inspiring. Whether you're a business owner, entrepreneur, or someone looking for motivation, this episode is packed with valuable lessons.

“It’s not about avoiding failure, it’s about learning from it and using it as fuel for growth” - Phil [14:45]

Tune in to learn more about how Phil Barone transformed adversity into success, why empathy is his superpower, and how he plans to grow Wayne Lifestyle into a national brand.

“Leadership starts from within. If you’re not taking care of yourself, you can’t effectively lead others” - Phil [23:30]

In This Episode

• [00:00] Introduction
• [02:03] The shocking moment that changed everything
• [06:08] How one act of courage shifted his entire perspective
• [07:00] Why a wrestling ring became the ultimate marketing move
• [12:03] Behind the scenes: what really happens in a wrestling match
• [14:00] The unexpected exposure that changed the game for Wayne Lifestyle
• [17:25] From freight to fame: the story of a business reborn
• [21:43] How a moment of self-reflection transformed his sales strategy
• [24:00] The secret to connecting with people (and it’s not what you think)
• [27:07] Empathy: the superpower that fueled his success
• [30:53] What’s next for Wayne Lifestyle? Big plans ahead
• [34:00] Why community is the secret ingredient to building a brand
• [36:27] How to connect with Phil Barone

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About David Schnurman

David Schnurman is the CEO of Lawline, the leading online continuing legal education platform that has delivered more than 5 million courses to 150,000+ attorneys, as well as a bestselling author, TEDx speaker, and entrepreneur focused on growth, learning, and intentional leadership. Known for helping leaders expand beyond their comfort zones, David combines business strategy with personal transformation, most notably through his bestselling book 11 Suitcases, which chronicles his family’s move from Brooklyn to Barcelona and the life-design lessons that came from it.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

David Schnurman

• LinkedIn
• Instagram
• Lawline Website
• Eleven Suitcases: How Moving Abroad Changed a Family Forever

Episode Highlights

What does it really look like to design a business that gives you more life instead of less?

In this episode of Business Unchained, Bobby Mascia sits down with David Schnurman to unpack the story behind moving his family to Barcelona for two years with just 11 suitcases while continuing to lead Lawline. What begins as a conversation about travel quickly becomes a deeper discussion on visionary leadership, family values, writing down goals, founder courage, and creating operational systems that allow a business to thrive without constant founder presence. David breaks down the “little yeses” that turned a distant dream into reality and explains how intentional decisions compound into life-changing outcomes.

“When you write something down from what’s in your mind, and you put it in writing, it’s more likely to turn into something.” - David [04:52]

The conversation also explores the psychology behind growth: how entrepreneurs can stay outside their comfort zone longer, why most people retreat too quickly after taking action, and how frameworks like journaling, consistency, and “don’t break the chain” habits create long-term momentum.

In This Episode

• [00:00] – Introduction
• [01:55] – David introduces 11 Suitcases and the Barcelona move
• [04:52] – Why writing goals down changes your future
• [06:29] – David’s midlife rut and the catalyst for change
• [07:16] – How he structured Lawline to run while living abroad
• [11:11] – The unexpected gift of the expat community
• [12:24] – The “cargo ship” metaphor that inspired the book
• [16:22] – Landing in Spain: the emotional reality vs the dream
• [20:36] – The school dean’s advice: say yes to everything
• [22:23] – How the kids adapted faster than expected
• [25:33] – Keeping the travel mindset alive after returning home
• [30:37] – The Fast Forward Mindset framework for fearless action
• [34:14] – Why most people crawl back into their comfort zone
• [36:10] – The Jerry Seinfeld “don’t break the chain” lesson
• [39:31] – ADHD, dopamine, and thriving in entrepreneurial chaos
• [44:27] – David’s next chapter: family transitions, third book, and speaking

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About TJ Bongiorno

TJ Bongiorno is the founder of The Outgoing Co, a fast-growing supplement and nootropic brand focused on alcohol alternatives, functional beverages, and modern wellness products. Before going full-time as an entrepreneur, he worked in mortgages, learned to code through a bootcamp, and built a career in tech as a sales engineer. By building in public and testing demand early, TJ built a multi-seven-figure brand without employees.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

TJ Bongiorno

• LinkedIn
• Instagram

Episode Highlights

In this episode of Business Unchained, Bobby Mascia sits down with TJ Bongiorno to break down how he built The Outgoing Co. into a multi-seven-figure e-commerce brand without employees. TJ shares his path from mortgages to tech sales to launching a supplement company on the side while still working full-time. He explains why testing demand before scaling was one of the smartest moves he made, including using a pre-sale to validate the idea before fully investing. The conversation also highlights how building in public helped him grow an audience and create momentum around the brand.

Bobby and TJ also get into the messier side of entrepreneurship, including product missteps, formula changes, supply chain issues, and trademark headaches. TJ opens up about what it took to stay lean, use AI and outside support, and keep moving even when things got complicated. They talk through raising capital, evolving the brand vision, and why modern founders need to think bigger than just getting a product to market. The episode also explores TJ’s mission to create a real, socially acceptable alternative to alcohol through functional wellness products like Audi and Yapper.

“I went from like, hopefully I can make a million dollars to, I wanna sell this for 200 million.” - TJ [34:00]

In This Episode

• [00:00] Introduction
• [04:16] Starting the business on the side while working full-time as a sales engineer
• [05:29] Building in public on X and the mindset of “figure it the fuck out ability”
• [07:55] The article that demystified how to start a supplement company
• [12:21] The first year of growth and using influencer marketing to reach $100,000 in sales
• [18:45] The core idea behind creating a real alternative to alcohol
• [24:56] Tariffs, customs delays, and the supply chain nightmare that nearly broke fulfillment
• [29:12] Launching Yapper and why beverages can create massive exit potential
• [32:51] Why founders need entrepreneurial peers and real operator networks
• [34:00] How TJ’s vision grew from making money to building toward a massive exit
• [37:24] Leaving a high-paying job, building a financial safety net, and taking the leap
• [40:40] Finding the right investor and avoiding the wrong money
• [46:35] Why IP and trademarks matter if you want a clean exit
• [51:25] Running a multi-seven-figure business with no employees
• [59:21] TJ’s best advice for founders: marketing, consistency, X, and content
• [01:02:00] Who buys The Outgoing Co. and where customers find the brand

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About Rob Wolcott

Rob Wolcott is a venture investor, professor, and author of Proximity. He teaches at both Kellogg and Chicago Booth, has invested in roughly 30 startups directly, and spends his time studying where technology, AI, innovation, and the global economy are headed next.

Reference Links: 

• Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance:  https://a.co/d/dSwUruD
• Linkedin
• Green Ridge Wealth Planning
• BobbyMascia.com
• Instagram - Bobby Mascia
• Instagram - Business Unchained

Rob Wolcott

• Proximity: How Coming Breakthroughs in Just-In-Time Transform Business, Society, and Daily Life
• LinkedIn
• TWIN Global Website

Episode Highlights

What if the companies that win next are not the biggest, but the ones that can create value closest to the exact moment a customer needs it? In this episode of Business Unchained, Bobby Mascia sits down with Rob Wolcott for a sharp conversation on venture investing, founder judgment, AI-driven entrepreneurship, and the future of business strategy.

“I allow myself occasionally to take a flyer. And what I mean by that is that there are no red flags. I think it could be really big, and I wanna be in for the ride a bit. That's my $10,000 ticket.” – Rob [10:42]

Rob also breaks down how he evaluates startups, what makes a founder worth betting on, and why trust, follow-through, and coachability matter just as much as the idea itself. He unpacks the core concept behind Proximity and explains how digital technologies are moving products, services, and experiences closer to real-time demand.

“This is proximity. Digital compels the creation of value ever closer to the moment of actual demand and time and space.” – Rob [19:20]

The conversation also goes deep on AI, the future of entrepreneurship, and why the next wave of winners will come from people who stop forcing new technology into old frameworks. Rob shares why he believes we may see billion-dollar companies run by just one or two people, and he gives business owners a simple but powerful question to ask: What would your customers want in the future if they could have absolutely anything?

In This Episode

• [00:00] – Introduction
• [01:53] – Rob’s portfolio, startup exits, and what he has learned as an investor
• [03:30] – What makes a business truly exit-ready
• [05:12] – When a company evolves from a high-growth startup to a mission-driven business
• [07:22] – The founder traits Rob looks for before making an investment
• [12:12] – Why brilliant founders still need coachability and business builders
• [14:33] – The origin story behind Proximity
• [19:20] – What proximity means and why value is moving closer to demand
• [36:22] – Rob’s next idea, post-virtual reality and the future of human experience
• [40:03] – Why the next 20 years may be messier than people think
• [47:27] – The key question every business owner should ask about the future
• [56:09] – What students should study to prepare for the future
• [01:00:19] – Why Rob says there will be no robot apocalypse
• [01:01:18] – Where to connect with Rob Wolcott and find Proximity