Modern Investing Podcast

Message the Host

In this episode, we sit down with Todd Sullivan, serial entrepreneur and CEO of ExitWise, to explore the art and science of successful business exits. With four successful exits under his belt, Todd shares what most founders overlook—and what makes the difference between a mediocre and a life-changing M&A deal.

Todd reveals:

• Why professional representation is non-negotiable in maximizing valuation
• How to prepare your financials and story to stand up to intense buyer scrutiny
• Why knowing your “number” (your ideal exit goal) is critical—and how to align it with post-tax, post-sale life
• The common pitfalls founders make when entering M&A too casually
• His personal playbook for creating wealth and meaning after the exit

If you're scaling a company, thinking about selling, or planning for long-term wealth after an exit, this episode delivers essential guidance and hard-won insight from one of the top experts in the game.

About Todd Sullivan:

Todd Sullivan is the founder and CEO of ExitWise, a tech-enabled platform that helps entrepreneurs navigate business exits with expert M&A representation. With experience building and selling four companies, Todd understands the emotional, strategic, and financial complexities of letting go—and doing it well.

He created ExitWise to ensure founders no longer enter M&A processes blind. His team assembles custom-fit advisory groups of seasoned M&A professionals to help entrepreneurs get the right deal, with the right partners, at the right time. Todd’s work is trusted by startup founders, private equity firms, and business owners nationwide who are preparing for high-stakes liquidity events.

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’re joined by AJ Bubb, fractional product and innovation leader, former CTO of Lion Rocket Entertainment, and experienced real estate investor—to explore what it takes to invest and build with confidence during challenging market conditions.

AJ shares:

• How he live-streamed a 25,000-person NASA event from a remote airfield—and what it taught him about innovation under pressure
• His transition from tech to active real estate investing, and why he prefers profitable assets over fixer-uppers
• Advice for entrepreneurs managing post-exit wealth, including developing a personal investment philosophy
• The importance of having a trusted, local network when investing in out-of-state markets
• Why rapid but calculated decisions—and clarity on risk tolerance—are crucial for wealth preservation and growth

This episode is a must-listen for business owners, founders, and investors who want to level up their thinking around wealth, risk, and execution—especially in volatile times.

About AJ Bubb:

AJ Bubb is a fractional product and innovation leader with a rare blend of experience across technology, entertainment, and real estate investing. Formerly the CTO of Lion Rocket Entertainment, AJ led large-scale, cutting-edge projects—including coordinating with NASA JPL to broadcast live from remote field locations.

Now, AJ helps entrepreneurs and operators scale their impact and strategically invest across asset classes. He specializes in identifying pragmatic, cash-flowing real estate opportunities and provides a grounded perspective on managing wealth in uncertain environments. AJ is known for bridging bold vision with disciplined action—making him a sought-after advisor for those navigating transitions, exits, and long-term wealth planning.

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 Nathan Creswell—Head of Product, angel investor, and syndicate lead at Swell Ventures—to explore how deep product expertise can drive smarter, more strategic early-stage investments.

Nathan shares:

• His journey from early product roles at Bay Area startups to leadership at Salesforce and Zuora
• How product thinking informs his angel investment thesis—especially in B2B SaaS
• Insights on vetting early-stage companies through team, timing, and technical readiness
• His take on AI, Web3, and the technologies poised to reshape modern business
• How he balances full-time leadership with investing—and why network quality matters more than deal quantity

Whether you’re building a startup, investing in one, or scaling both career and capital, Nathan’s perspective will help you think more clearly, move more strategically, and stay ahead of the curve.

About Nathan Creswell:

Nathan Creswell is a product executive, angel investor, and syndicate lead at Swell Ventures, where he focuses on early-stage B2B SaaS opportunities and emerging technologies. With a strong foundation in product management, Nathan built his career in tech with roles at Salesforce, Zuora, and multiple startups in the San Francisco Bay Area.

As an investor, Nathan combines strategic product thinking with market analysis to back founder-led, high-potential companies—especially in sectors being reshaped by AI, Web3, and enterprise innovation. He’s passionate about helping teams grow thoughtfully, and about empowering investors to align their expertise with their capital.

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 Israel Suero, a seasoned investor and Limited Partner at Dash VC, whose journey spans Wall Street, tech leadership at Uber Eats and DoorDash, and bold investments across real estate, crypto, angel deals, and venture capital.

Israel shares:

• His evolution from stock trading with family to strategic VC and angel investments
• How he leveraged career transitions—from Wall Street to scaling in tech—to sharpen his investing edge
• The power of making asymmetric bets: high-upside, calculated-risk decisions that changed his life
• His approach to building a diversified portfolio that balances bold moves with long-term stability
• Reflections on legacy, family, and how to win without losing your why

Whether you’re navigating your first angel deal or optimizing a multi-asset strategy, Israel’s story offers hard-earned insight, tactical wisdom, and deep personal clarity.

About Israel Suero:

Israel Suero is a dynamic investor, operator, and LP at Dash VC, with hands-on experience across venture capital, crypto, real estate, and public markets. His professional path spans from Wall Street finance to impactful roles at Uber Eats and DoorDash, where he honed his strategic lens on high-growth tech.

Known for his conviction-driven investing style and dedication to financial education and legacy building, Israel is passionate about empowering others to bet smart—while staying grounded in their values. His current focus includes supporting transformative tech, especially in AI, while maintaining a balanced approach to risk, reward, and meaning.

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 Ronald Flores, CEO of Curious Finance, to explore how personalized, team-based financial strategies are reshaping wealth management—especially for business owners and high-achievers navigating today’s fast-changing economy.

Ronald shares:

• Why goal-based planning outperforms one-size-fits-all financial advice
• How business owners can build wealth management teams to handle taxes, insurance, investments, and risk
• The growing importance of alternative investments and diversification
• His thoughts on how technology empowers clients while keeping advisors relevant
• Why holistic planning is the future of financial freedom and confidence

This episode is a must-listen for entrepreneurs, executives, and anyone ready to move beyond reactive investing and into proactive financial leadership.

About Ronald Flores:

Ronald Flores is the Founder and CEO of Curious Finance, a modern financial advisory firm that specializes in comprehensive wealth planning for business owners and high-net-worth individuals. With a deep background in financial services, Ronald focuses on building integrated teams around clients—combining expertise in investments, insurance, tax strategy, and tech-enabled tools.

A strong advocate for client empowerment, Ronald believes the future of finance lies in personalization, transparency, and systems that evolve with the complexity of people’s lives. He helps clients design not just portfolios—but financial ecosystems that reflect their goals, values, and legacy.

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 explore the intersection of technology, strategy, and entrepreneurship with Guy Reams, investor, tech executive, and member of New Fund Venture Group.

Guy shares:

• His journey from computer science professor to tech executive and founder of a non-profit chess club
• Lessons from transitioning between academia, corporate roles, and startup investing
• His approach to identifying early-stage opportunities in B2B SaaS, with a focus on team dynamics and traction
• A behind-the-scenes look at how he manages personal investing, balancing risk while planning generational wealth
• Why his love of chess strategy mirrors his disciplined investment mindset

If you're curious about early-stage investing, startup evaluation, or how personal values inform portfolio construction, this episode is packed with wisdom from a leader who blends logic, heart, and foresight.

About Guy Reams:

Guy Reams is a technology executive, angel investor, and partner at New Fund Venture Group, where he supports early-stage tech companies with a focus on B2B SaaS and scalable solutions. With a background that spans computer science education, corporate tech, and entrepreneurship, Guy brings a unique blend of analytical rigor and real-world insight to his investing.

Outside of his professional pursuits, Guy is the founder of a non-profit chess club, reflecting his lifelong love for strategy, teaching, and community-building. He’s deeply committed to helping startups grow with integrity, and to building a financial future for his family rooted in long-term thinking and values-driven 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 

Message the Host

In this episode, we’re joined by Kris Mathis—entrepreneur, author, and creator of Let’s Help Her Win, a new reality series aimed at empowering women entrepreneurs through capital, mentorship, and visibility.

Kris shares:

• His personal story of resilience, reinvention, and rising above setbacks
• What pushed him to leave a traditional path and step boldly into full-time entrepreneurship
• Why he believes in investing with both head and heart—especially when backing underrepresented founders
• The vision behind Let’s Help Her Win and how it’s creating transformative opportunities for women-led startups
• His philosophy on life, risk, and timing: “If you don’t move on life, life will move on you.”

This episode is a deeply human, highly motivating conversation about turning purpose into power, and how investing in people and potential can lead to profound, lasting impact.

About Kris Mathis:

Kris Mathis is a renowned speaker, entrepreneur, and author known for inspiring others through his story of personal transformation and business leadership. After overcoming early failures and a serious health challenge, Kris emerged with a mission: to use his voice and vision to empower others to rise.

As the creator of Let’s Help Her Win, Kris is building a platform that supports women entrepreneurs through capital, mentorship, and media exposure—helping founders who are often overlooked access the resources they need to succeed. His work blends business strategy with heart-centered leadership, making him a powerful force for equity, innovation, and impact in the entrepreneurial world.

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 Mike Clark, a financial advisor with a bold background in investment banking, capital raising, and alternative strategies. From selling medical devices to raising millions and guiding clients through self-directed IRAs, Mike brings a unique, tactical approach to building and protecting wealth.

Mike shares:

• His non-traditional path into finance and why it gives him an edge
• How self-directed IRAs unlock new investment opportunities—beyond just stocks and bonds
• Why the “wealthy investor” playbook should be more accessible to everyone
• How to build goal-oriented, diversified portfolios that reflect personal expertise and values
• His thoughts on restoring trust in financial strategy through transparency and education

Whether you’re looking to diversify your retirement funds, take control of your investment decisions, or simply learn from someone who’s made the leap from Wall Street to Main Street, this episode is packed with insights and empowerment.

About Mike Clark:

Mike Clark is a financial advisor with a distinctive background in investment banking and capital markets, where he helped raise millions for private deals and emerging opportunities. Today, Mike works directly with clients to develop custom financial plans, with a strong focus on leveraging self-directed IRAs, alternative investments, and long-term wealth strategies.

He is passionate about making elite-level financial knowledge understandable and actionable for everyday investors—helping them break free from outdated models and move toward clarity, autonomy, and sustainable success.

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’re joined by Austin McCulloh, a former financial advisor turned tech entrepreneur, to explore how innovation is reshaping both the financial advisory industry and personal wealth-building.

Austin shares:

• His journey from financial advisor to founder of Reply Assist, a tool built to help advisors scale meaningful client conversations
• Why he left the traditional finance world to solve problems with technology and automation
• How today’s economic landscape demands adaptability, creativity, and vision
• His evolving investment philosophy, including why he favors business building over passive income in the early stages—and why angel investing is on his radar
• A compelling perspective on how investing can create freedom, not just returns

This episode is a compelling listen for financial professionals, aspiring founders, and anyone exploring the intersection of entrepreneurship, investing, and personal autonomy.

About Austin McCulloh:

Austin McCulloh is the founder of Reply Assist, a tech solution designed to help financial advisors grow their business by streamlining and scaling client outreach. Before launching his startup, Austin worked as a financial advisor, where he developed a deep understanding of both the industry’s limitations and its potential.

Driven by a passion for entrepreneurship, innovation, and financial empowerment, Austin is committed to helping others take ownership of their financial path. His investing strategy focuses on long-term value through business ownership, with plans to expand into angel investing and venture capital following future exits.

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 Nick Larson—Silicon Valley investor, CRO of Unity Central, and host of the top 5% globally ranked podcast Silicon Zombies—to explore how to stay ahead of the curve by aligning values with vision.

Nick shares:

• His journey from startup founder in supply chain tech to active investor in deep tech and agrosonics
• Why he believes in "skating to where the puck is going" and spotting early macro and micro trends
• How platforms like Sidepocket are making institutional-grade strategies available to everyday investors
• Insights into AI, biomimicry, and democratized investing models
• The importance of investing as a journey of narrative and intention, not just returns

This episode is a must-listen for investors, technologists, and impact-driven thinkers who want to do well by doing good in a world rapidly shaped by innovation.

About Nick Larson:

Nick Larson is a Silicon Valley-based tech executive, investor, and podcast host known for his unique ability to spot and act on emerging trends. As Chief Revenue Officer at Unity Central, he leads growth strategy for innovative enterprise solutions. He’s also the host of Silicon Zombies, a globally ranked podcast exploring the intersections of tech, humanity, and the future.

A seasoned startup founder turned angel investor, Nick has backed innovations in fields ranging from agrosonics to AI infrastructure, with a focus on technology that serves both profit and planet. He’s passionate about tools that democratize sophisticated investing, and his collaboration with Sidepocket reflects a belief in long-term, transparent, and intelligent financial growth.

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