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In this episode, we welcome Matteo Costa—angel investor, Techstars startup mentor, and ETF strategist—for an inside look at how to blend long-term investing with entrepreneurial impact.

Matteo shares:

• His path from consulting and corporate innovation to angel investing
• How working with Techstars shaped his mentoring philosophy
• The structure behind his ETF portfolio for long-term wealth creation
• His passion for impact investing in food tech, sustainability, mental health, and psychedelics
• How he evaluates early-stage companies across sectors of personal and global significance

“You can build wealth and still stay aligned with your values—if you're intentional about where your money goes.”

If you’re exploring the crossroads of entrepreneurship, capital, and conscious investing, this episode delivers clarity, heart, and actionable wisdom.

About Matteo Costa:

Matteo Costa is a startup mentor, angel investor, and ETF strategist with a multidisciplinary background spanning consulting, corporate innovation, and startup co-founding. He serves as a mentor for Techstars, where he supports founders in navigating the startup journey, and actively invests in early-stage ventures across sectors that include climate tech, food innovation, mental health, and psychedelics.

Matteo brings a long-term lens to investing—building a values-aligned ETF portfolio while championing purpose-driven innovation. With a unique ability to bridge institutional thinking and startup agility, he helps founders and investors alike align strategy with mission.

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About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we sit down with Silvia Lupu, one of the youngest independent female fund managers ever nominated for Fund Manager of the Year (2023), and the visionary currently leading Jevan Capital.

With over a decade of experience across real estate, private equity, tech, and financial markets, Silvia shares:

• Her unique framework for diversified, cross-asset investing
• Why cutting through the noise is critical to spotting undervalued opportunities
• The investing principles that have guided her through cycles and volatility
• What she sees as key shifts in 2024 and how investors can stay ahead
• Her mission to bring clarity, rigor, and long-term thinking into a fast-moving space

“In a noisy world, the edge goes to those who can isolate the signal.”

This conversation is a masterclass in modern portfolio construction, disciplined decision-making, and strategic foresight—from someone reshaping the landscape of investing for the next generation.

About Silvia Lupu:

Silvia Lupu is the Fund Manager at Jevan Capital, a trailblazer with over 10 years of experience spanning real estate, technology, private equity, and traditional financial markets. In 2023, she was nominated as the youngest independent female Fund Manager of the Year, recognizing both her results and her influence in shaping the future of capital.

Known for her precise, disciplined approach to identifying under-the-radar opportunities, Silvia is passionate about creating portfolios that stand the test of time. She leads with conviction, clarity, and a firm belief that successful investing is equal parts art, science, and leadership.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we sit down with Patrick McCarthy, Fractional CFO and angel investor in over 200 startups, to explore the intersection of public markets, private equity, and mission-aligned investing.

Patrick shares:

• How a stock trading game in middle school ignited his passion for investing
• The long-term mindset that guides his diversified portfolio
• Why he's bullish on platforms like Sidepocket to democratize access to private markets
• Insights from working with over 50 startups as a strategic financial advisor
• His bold mission: to help 1,000 startups scale and thrive in the next decade

“You guys are bringing access to something your everyday investor can’t get today—and that’s critical to changing how wealth works in this country.”

Whether you're a founder raising capital or an investor expanding your exposure, Patrick’s grounded wisdom offers a roadmap to navigating today’s financial frontier with purpose and precision.

About Patrick McCarthy:

Patrick McCarthy is a seasoned Fractional CFO, startup advisor, and angel investor with deep experience across finance, fundraising, and startup operations. As former VP of Finance at SpokenLayer, he led critical initiatives from cap table management to revenue strategy.

He’s advised over 50 startups and invested in 200+ companies across tech, media, and SaaS, all part of his mission to support 1,000 startups in the next 10 years. Known for his blend of value-based investing and hands-on financial leadership, Patrick brings both analytical depth and heart to every founder relationship—and every investment he makes.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we sit down with Robert Schneider, a veteran entrepreneur and angel investor, to trace his journey from paper routes to leading success in the cannabis industry—and to explore the mindset that’s guided his evolution along the way.

Robert shares:

• How his early entrepreneurial instincts grew into multi-industry success
• The principles behind his angel investing strategy, including his investment in Sidepocket
• His belief in investing not just for returns, but for beauty, impact, and legacy
• Why he’s bullish on founder-led businesses, including his support for his brother’s restaurant venture
• His experience using Sidepocket, praising its user-friendly onboarding and adaptability in volatile markets

“I want to leave something behind that adds to the beauty of the world.”

This episode is a grounded, insightful take on what it really means to invest with intention—from cannabis to tech to family.

About Robert Schneider:

Robert Schneider is a seasoned entrepreneur, investor, and operator with deep experience in the cannabis, retail, and hospitality industries. From launching businesses in his youth to building thriving companies in regulated markets, Robert brings a blend of strategic discipline and creative vision to everything he does.

As an angel investor, Robert focuses on startups that align with his values and long-term vision—supporting platforms like Sidepocket and founder-led ventures, including his own family’s restaurant business. His investment philosophy centers on purpose, resilience, and contribution, with a legacy-minded approach that balances financial performance with positive impact.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we meet Aharon Herbert, co-founder of CENO AI, whose journey from Bay Area tech student to investor and entrepreneur is a testament to what’s possible when passion meets purpose.

Aharon shares:

• His path from scholarship student to a role in corporate IT at Visa, where he works on projects involving AR/VR and Microsoft integration
• The inspiration behind CENO AI, a platform designed to help users achieve personal goals using generative AI and adaptive planning
• His approach to investing as a young professional: learning, staying conservative when needed, and always staying curious
• Why uplifting others is his deepest motivation — in both tech and life
• How sports, discipline, and community have shaped his entrepreneurial mindset

“Build what you want to see in this world… That’s why I’m building the future I want to live in.”

This episode is an inspiring look at how the next generation of entrepreneurs is blending technology, emotional intelligence, and innovation to create tools that empower people—not just profit.

About Aharon Herbert:

Aharon Herbert is a tech-focused entrepreneur, investor, and corporate IT professional based in the San Francisco Bay Area. He currently works at Visa, where he supports innovation through internal partnerships with teams like Microsoft.

He’s the co-founder of CENO AI, a startup that uses AI-driven goal planning to help users take control of their careers and personal growth. Outside of work, Aharon is a passionate athlete, a student of investing, and someone deeply committed to building products—and communities—that reflect a better future.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we sit down with Cara Macksoud, FBS®, CEO of Money Habitudes, to explore how your relationship with money shapes your financial outcomes—and what to do if it’s holding you back.

Cara shares:

• How her experience as a Wall Street ETF trader and nonprofit CFO led her to the psychology of money
• The hidden beliefs and behaviors that affect your ability to build wealth
• Why understanding your financial “habitudes” is key to better decisions
• How she helps individuals and professionals reprogram money mindsets
• Tools to improve financial wellbeing through awareness, not just strategy

“People don’t fail at money because of math—they fail because of emotion, identity, and fear.”

Whether you're managing wealth, advising clients, or navigating your own financial healing, Cara offers practical, compassionate insights into how to align your habits with your goals—so money can work with you, not against you.

About Cara Macksoud, FBS®

Cara Macksoud is the CEO of Money Habitudes, a Financial Behavior Specialist®, and one of the youngest women to earn a trading seat on the NYSE. Her career spans over a decade in ETF trading, leadership roles in the nonprofit sector, and a deep commitment to financial psychology and education.

She holds a BS in Finance from NYU Stern, completed a graduate certificate in Financial Therapy from Kansas State University, and is an active member of the Financial Therapy Association and AFCPE. Cara now empowers individuals and advisors to understand the emotional side of money—helping people shift not just what they do with money, but how they relate to it.

She lives in Florida with her husband and five kids, where they enjoy warm weather and shark tooth hunts.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

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In this episode, we talk with Clay Risher, Director at boutique investment bank True North Capital Partners, about what it means to be a true fiduciary in an age of algorithms, influencers, and AI-driven hype.

Clay shares:

• His personal evolution from emotional trading to research-backed investing
• Why regulatory ethics matter more than ever (including lessons from celebrity crypto endorsements)
• How value investing and long-term thinking still outperform the noise
• His views on AI in investing — and why he still believes in human judgment
• Why Sidepocket’s model of access + integrity caught his attention

“For me, life is just a curiosity shop every day... I don't really want my inner or outer world interpreted for me by a machine.”

This episode offers a grounded take on modern investing — where data meets wisdom, and technology supports, not replaces, discernment.

About Clay Risher:

Clay Risher is a seasoned investment banker, entrepreneur, and Director of Business Development at True North Capital Partners, where he focuses on M&A, capital raising, and valuation services across finance, tech, and private equity.

With a career spanning executive roles in both public and private companies, Clay has led transformative transactions and strategic initiatives. He’s also an award-winning author and a contributor to REIT Magazine, where he interviews industry leaders and shares insights from the frontlines of modern capital markets.

Clay studied literature and economics at Boston University and completed advanced coursework in finance at Fairfield University. Off the clock, he’s an avid outdoorsman and curious observer of life, always chasing both beauty and truth — whether in architecture, nature, or investing.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

Message the Host

In this episode, we sit down with Kamil Czubacki, CEO of AumBio Wellness Center, to explore how he transformed skepticism into belief—and belief into business success—in the world of alternative wellness and smart investing.

Kamil shares:

• How a breakthrough experience with German wellness tech changed his father’s life
• His evolution into a wellness entrepreneur and community leader
• Why financial education and diversification are critical to long-term success
• His approach to creating multiple income streams and balancing risk
• How tools like Sidepocket helped him automate growth and reclaim time

“Just remember, go for it, put everything in you can, and get financially educated.”

This is a must-listen for anyone seeking inspiration at the intersection of purpose, wellness, and financial freedom.

About Kamil Czubacki:

Kamil Czubacki is the CEO and President of AumBio Wellness Center, a pioneering alternative wellness hub based in Chicago. Once a skeptic, Kamil became a passionate advocate for innovative bioresonance and holistic therapies after witnessing their life-changing effect on his father.

Today, Kamil blends his entrepreneurial drive with financial insight, emphasizing the importance of education, multiple asset classes, and accessible investing. His journey serves as a blueprint for those looking to grow their impact and their wealth—without compromising values.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

Message the Host

In this episode, we talk with Nate Bailey — U.S. Army veteran, entrepreneur, and leadership coach — about what it takes to develop a championship mindset and lead with purpose in business, investing, and life.

Nate shares:

• His transition from the military to entrepreneurship
• Lessons from real estate investing and his curiosity about day trading
• Why intentionality and personal integrity are non-negotiables for leaders
• His thoughts on tools like Sidepocket that automate smart investing
• How he helps men step into strong, grounded leadership in today’s world

“Why would you not?” — Nate’s challenge to anyone avoiding growth and alignment

Whether you're building wealth, building muscle, or building discipline, this episode is for anyone ready to compete, grow, and lead from within.

About Nate Bailey:

Nate Bailey is a leadership coach, Army veteran, author, and founder of the 5-Day Unleash The Leader Within Challenge and the Championship Leadership 24-Hour Experience. He hosts the top-rated Championship Leadership Podcast and is the author of 100 Mile Mindset: Discover the Power of Being Your Word.

Nate works with former athletes, veterans, and driven men to help them avoid the setbacks he faced and step into lives of purpose, integrity, and impact. Through his coaching programs and mastermind community, Nate is redefining what it means to be a strong leader in business, relationships, and personal development.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com

Message the Host

In this episode, we speak with Marc Cohen, executive advisor and founder of Buy Direct Development Companies, about the mindset and strategy behind building lasting wealth and leading through values.

Marc breaks down:

• The 5 core traits every successful business and investor must cultivate: Integrity, Accountability, Diligence, Perseverance, and Discipline
• Why early financial education is crucial — and how it’s tied to emotion and energy
• How to align your finances with your family values and future goals
• His path from humble beginnings to advising multi-billion-dollar enterprises

“The planning of your finances at a young age and getting educated is crucial—and it's all interconnected with emotions and energy.”

If you're a founder, executive, or parent seeking to grow wealth while staying grounded, this episode delivers timeless insight on how to lead, plan, and build with intention.

About Marc Cohen:

Marc Cohen is a visionary business strategist and top-level executive with decades of experience advising multi-billion-dollar companies. As the founder of Buy Direct Development Companies, he combines financial acumen with a passion for emotional resilience and family-focused planning.

Marc is known for helping leaders create generational wealth through integrity-based strategy, a wide-ranging professional network, and deep wisdom drawn from his own rise from humble roots. His mission: help others build not just financial success, but meaningful, sustainable lives.

Click Here to Check Out Our Upcoming Online
Investing Events

About Sidepocket:

If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.

Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss.

That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.

To learn more, visit www.sidepocket.com