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In this episode, we sit down with Mark Willis, Certified Financial Planner™ and owner of Lake Growth Financial Services, to explore a radically different path to building wealth—by transforming debt into financial freedom.

Mark shares his personal story of paying off six figures in student loans and how that challenge led him to question conventional financial advice. Now a nationally recognized expert on alternative wealth strategies, Mark walks us through:

• Why 401(k)s, IRAs, and deferred taxes may not serve entrepreneurs as well as promised
• How management fees and market volatility quietly erode long-term gains
• The mechanics behind the “Bank on Yourself” strategy using dividend-paying whole life insurance
• How to access capital for your business while building predictable wealth
• Real client stories that prove safe, liquid, and tax-efficient strategies can outperform the norm

“Don’t just park your money and hope—make it move, and make it work for you.”

Whether you’re an entrepreneur looking to escape debt, invest in your business, or avoid the traps of traditional retirement plans, this episode is a must-listen for rethinking how to grow and protect your wealth.

About Mark Willis, CFP®:
Mark Willis is a Certified Financial Planner™, bestselling author, and the founder of Lake Growth Financial Services, a financial firm helping thousands of clients nationwide rethink their relationship with money. He specializes in alternative wealth-building strategies that prioritize liquidity, stability, and control. As co-host of the Not Your Average Financial Podcast™, Mark has become a go-to resource for entrepreneurs seeking smarter ways to manage debt and achieve long-term financial success.

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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 Shridhar Swaminathan, Co-Founder and CTO of Sidepocket, to explore how automation, quantitative investing, and behavioral risk management are reshaping the future of wealth management.

With 20+ years of experience spanning data science, technology startups, and financial strategy, Shridhar shares:

• His transition from tech consulting to quant investing and fintech innovation
• Why Sidepocket was built to solve the “drawdown problem” for everyday investors
• How automation eliminates emotional decision-making and supports portfolio resilience
• Tactical advice for entrepreneurs selling their businesses and reallocating capital
• Why systematic investing, diversification, and risk modeling matter more than ever

“Don’t be emotionally attached to your money—be strategic. Let the system do the heavy lifting.”

Whether you're building a business or exiting one, this episode offers powerful insights into preserving and growing wealth without needing to be hands-on with the market. Learn how Sidepocket’s data-driven platform empowers investors to make smarter, more stable decisions for the long haul.

 About Shridhar Swaminathan:
Shridhar Swaminathan is the Co-Founder and CTO of Sidepocket, a fintech platform pioneering accessible quant investing. He brings over two decades of experience at the intersection of startup technology, data science, and portfolio risk management. Shridhar’s approach blends rigorous modeling with a human understanding of how entrepreneurs and investors behave under pressure—leading to tools that help users stay the course and build long-term financial security.

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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 Anmol Singh—veteran trader, investor, and founder of LiveTraders—to explore how mastering the psychology behind trading can lead to long-term investing success.

With 14+ years of experience and over 10,000 students coached, Anmol shares:

• How he began trading at 18 and built a successful career through discipline and mindset
• Why coaching and mentorship are essential for new traders
• The importance of risk management in both short-term trading and long-term investing
• His “two-bucket” strategy for balancing income generation and wealth building
• Why trading psychology matters just as much as technical analysis
• How tools like Sidepocket support disciplined, diversified investing across asset classes

“If you don’t have a risk management plan, you don’t have a trading plan.”

This episode is a must-listen for aspiring traders, active investors, and anyone looking to elevate their financial strategy through proven techniques and psychological resilience.

About Anmol Singh:
Anmol Singh is a professional stock trader, investor, and the founder of LiveTraders. Since launching his trading career in college, he has trained thousands of students and built a reputation for coaching high-performance traders across asset classes. He is also an angel investor, real estate investor, and a vocal advocate for tools that bring structure and discipline to personal finance. Anmol's work focuses on helping others master the mindset needed to achieve financial success in dynamic markets.

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 Evan Shubin, a 6x founder, 3x exited entrepreneur, and angel investor in over 25 startups. Now leading Candlelight Partners, LLC, Evan offers a rare window into what it takes to build, scale, and exit successful ventures—and how he now invests full-time across multiple asset classes.

With 25+ years of experience, Evan shares:

• How he bootstrapped Exhibitor Invites into a million-dollar trade show marketing firm
• Why he now works as a fractional C-suite leader in exchange for equity
• His investing playbook across startups, real estate, and public markets
• Key lessons from three exits—and what founders often overlook
• Why understanding customer pain points is the most underutilized growth strategy

“If you're building something great, the market will tell you—if you're listening.”

This episode is packed with firsthand insights for founders preparing to scale, exit, or start investing themselves. A must-listen for anyone balancing entrepreneurship and long-term wealth creation.

About Evan Shubin:
 

Evan Shubin is a veteran entrepreneur, investor, and strategic advisor with over 25 years of experience building, scaling, and exiting companies. As President of Candlelight Partners, LLC, he now serves as a fractional C-suite executive for startups, taking equity in exchange for his leadership.

A 6x founder with 3 exits under his belt, Evan has invested in over 25 startups while maintaining a diversified portfolio that includes real estate and public equities. His expertise spans marketing, operations, and go-to-market strategy, making him a sought-after partner for early-stage companies navigating growth or preparing for acquisition.

Evan’s career reflects a deep belief in listening to the customer, building around market pain points, and maintaining disciplined business fundamentals—even in fast-moving sectors.

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 James Fellus, a veteran investor and owner of one of the largest private Merchant Cash Advance (MCA) funding firms in the U.S., facilitating over $1 billion in deals each year.

With more than 30 years of experience in financial markets, James shares a behind-the-scenes look at how high-yield fixed-income opportunities can be found through MCA syndication and alternative lending. He unpacks:

• The mechanics of MCA investing—and how it differs from traditional lending
• Why MCA syndication can generate double-digit returns
• How his firm evaluates a business’s cash flow and credit profile in real time
• Risk management principles that have helped his firm grow in volatile markets
• Why diversified portfolios that include real estate, equities, and private credit are essential for long-term wealth

“If you're looking for real returns, you've got to be willing to look beyond Wall Street.”

This episode is a must-listen for investors exploring passive income strategies, and for entrepreneurs considering non-traditional funding to support growth.

About James Fellus:
James Fellus is the founder of one of the largest private funders of Merchant Cash Advances in the U.S., with over $1 billion in annual funding volume. With three decades of experience across asset classes—including equities, real estate, and alternative lending—James brings deep expertise in both investor strategy and small business capital deployment.

Known for his rigorous underwriting, operational acumen, and ability to scale high-yield investment vehicles, James is a sought-after voice in the alternative finance ecosystem. He’s passionate about helping business owners access working capital fast—and enabling investors to share in the upside of this growing asset class.

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 Zecca Lehn, General Partner at Responsibly Ventures, a California-based VC firm investing in U.S. PreSeed startups that align with the UN Sustainable Development Goals.

With a background as an Environmental Economist, Data Scientist, and Nonprofit Board Member, Zecca brings a rare blend of analytical rigor and human-centered investing to the venture world. He shares:

• His journey from living off-grid on a remote island to launching a mission-driven fund
• What it means to invest at the intersection of purpose and profit
• How Responsibly Ventures selects startups tackling climate, equity, and global wellbeing
• Why he believes early-stage investing is a lever for long-term systems change

“If we’re funding the future, we better be funding one that works—for people and the planet.”

This episode is a compelling listen for anyone passionate about aligning capital with conscience and investing in a better tomorrow.

About Zecca Lehn:

Zecca Lehn is the General Partner of Responsibly Ventures, a PreSeed VC firm backing mission-driven U.S. startups across social impact and sustainable technology sectors. With over 15 years of experience spanning environmental economics, data science, and entrepreneurship, Zecca brings deep insight into what it takes to build ventures that are both scalable and regenerative.

His upbringing in an off-grid, Japanese-style home in the Pacific Northwest—and later travels through Scandinavia—shaped a lifelong commitment to equity, ecology, and innovation. Through Responsibly Ventures, Zecca continues to champion founders building a more inclusive and sustainable 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

Message the Host

In this episode, we sit down with Justin Dixon, founder of Hire Tomorrow, who shares his journey of leaving the corporate W2 world to launch a recruiting firm and build a diversified investment portfolio—all during the height of the COVID-19 pandemic.

Justin shares:

• How he prepared financially to make the leap into entrepreneurship
• The importance of spending discipline and savings before leaving a stable job
• His strategy for strategic networking, including landing consistent business from a private equity firm
• Insights on building wealth through multifamily real estate and angel investing
• How to approach risk with clarity and confidence, especially during uncertain times

“Before I made the leap, I got really intentional about money. That gave me the freedom to take the risk.”

This episode is a must-listen for anyone considering a transition from employee to founder—or anyone looking to build financial independence through smart, intentional investing.

About Justin Dixon:

Justin Dixon is the founder of Hire Tomorrow, a boutique recruiting firm that connects top talent with high-growth companies. After spending years as a recruiter in the W2 world, Justin made the leap into entrepreneurship during the COVID-19 pandemic—relying on strong financial preparation and sharp business instincts to build a thriving firm.

Justin is also an active investor, with holdings in multifamily real estate, angel deals, and alternative assets. He’s passionate about helping others navigate the journey from financial security to entrepreneurial freedom, and believes deeply in strategic risk-taking, disciplined saving, and networking with purpose.

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 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

“Selling your business is not the finish line—it’s the starting point for the next chapter of your life.”

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

“Have a playbook, know your edges, and don’t chase deals that don’t match your risk profile.”

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

“Great investors think like great product managers—they ask the right questions before building anything.”

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