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What if the greatest investment you could make isn't in real estate, stocks, or even private credit—but in yourself? Dave Wolcott, former Marine officer turned alternative investment expert, shares how studying millionaires and billionaires led him to discover a holistic approach to wealth that goes far beyond your bank account. In this episode, Dave breaks down private credit (the hard money lending of the business world), explains why he focuses on just three asset classes, and reveals how investors are achieving 20%+ returns by cutting out the middlemen.

[00:00 - 05:30] From Marines to Triplets: The Wake-Up Call

• Served as an officer in the Marine Corps, traveled the world including Israel
• Had triplets in 2000, quadrupling his family size overnight with an 18-month-old at home

[05:31 - 09:25] The Six Forms of Capital: Beyond Financial Wealth

• The greatest investment is in yourself—not just the next deal
• Defines holistic wealth across six dimensions: financial, intellectual, spiritual, human, emotional, and social capital
  
  
  

[09:26 - 15:05] Private Credit Explained: The Business World's Hard Money Lending

• Banks are tightening regulations, creating gaps in funding for growing small businesses
• Private credit fills the need for fast capital—think roofing companies with 3 years of backlogged work after hurricanes

[15:06 - 20:05] How to Access Institutional-Quality Returns

• Pooling investor capital through a fund model to bring $10M+ to sponsors
• Gets the same terms as major institutions by working directly with sponsors (no middlemen)

[20:06 - 25:10] The Three-Asset Strategy: Real Estate, Energy, and Private Credit

• Ultra-wealthy get really good at 1-3 asset classes for best due diligence and deal flow

[25:11 - 31:00] Time Is the Real Asset

• Questions the accumulation theory: why defer taxes in a 401(k) when taxes will likely increase?

[31:01 - 33:05] Final Four & How to Connect

Connect with Dave:

Website: https://holisticwealthstrategy.com (free book download)

Podcast: Wealth Strategy Secrets of the Ultra Wealthy

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What if the key to successful multifamily investing isn't just about the numbers—but about the people living in your properties? Joe Rinderknecht, the cowboy-hat-wearing founder of Cowboy Capital, shares his unconventional path from shoveling manure on a Utah ranch to operating over 1,000 multifamily units.

[01:40 - 06:15] From Ranch to Real Estate: Building on Grit

• Grew up ranching and breaking horses in northern Utah—learned that your word is your bond
• Father left the ranch for construction and cabinet making, taught Joe everything from concrete to framing

[06:40 - 10:10] Trial by Fire: The 80-Unit Section 42 Property

• Asked for a property management job with zero experience—got thrown into an 80-unit low-income housing property
• Property had no manager for two weeks, with sky-high delinquency, vacancy, crime, drugs, and cockroaches

[10:11 - 15:20] The Path to Becoming a Sponsor

• Never planned to stay in property management long-term—goal was always to learn and move on
• Admits being "unemployable" with a resume showing 6-8 month stints at various companies

[16:35 - 23:35] Impact Investing: Making Every Dollar Matter

• Lost his brother (age 20) and grandmother in a 2013 car accident—nearly died himself
• Provides four types of support: capital, food, construction/home modifications, and mindset coaching

[23:36 - 26:40] Why Treating Tenants Well Is Good Business

• Questions how slumlords succeed when they don't care about people's lives
• When tenants feel like a unit is their home, turnover drops, repairs decrease, delinquency falls

[26:41 - 32:00] Rapid Growth and What's Next

• Bought 4 deals (419 units) since September 2024, currently under contract on 117 more units
• Believes there's a great buying opportunity in the next 10-24 months

[26:45 - 32:55] Final Four & How to Connect

Connect with Joe:

Website: https://cowboycapital.us
Email: Joe@CowboyCapital.us
LinkedIn: Joe Rinderknecht
Instagram: @joe_rinder

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Key Quote:
"If you can get a tenant to feel like their unit is their home, your turno

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Sometimes the best business decision is knowing when to let go. Amy Calandrino, founder of a commercial real estate brokerage, shares her journey from hammering in her own signs during the 2010 recession to building a team of nearly 10 advisors—and why she ultimately chose to close her firm to join Cushman & Wakefield. In this episode, Amy reveals the hidden costs of entrepreneurship, the importance of aligning your work with your values, and how she's redirecting her energy toward meaningful impact through her family foundation's financial literacy programs.

[01:05 - 04:10] From Vermont to Orlando: Building a Career on Grit

• Started working full-time at age 13 and put herself through college debt-free
• Worked alongside her husband in a law office where she learned about commercial real estate

[04:25 - 07:20] The Hidden Costs of Running a Brokerage

• Founded her brokerage in 2010 during the economic downturn with a shoestring budget
• Grew from solo founder to nearly 10 advisors by 2022

[07:21 - 11:45] Making the Leap: Consulting the Best in the Business

• Sought advice from industry leaders Sarah Malcolm, Allison Weiss, and Beth Azor
• Realized she could still be an entrepreneur without owning a brokerage

[11:46 - 19:30] The Three-Month Transition and Its Unexpected Lessons

• Spent 90 days transitioning clients and wrapping up her brokerage
• Experienced grief despite making the right decision

[19:31 - 27:15] Redirecting Energy: The Aspiring Entrepreneur Program

• Founded a family foundation with her husband to give back to the community
• Created an entrepreneurship program for elementary school students

[27:20 - 31:50] Final Four & How to Connect

Connect with Amy:

LinkedIn: https://www.linkedin.com/in/amycalandrino/

Email: Amy.Calandrino@cushwake.com

Book: "From Perfect to Real" (available on Amazon)

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"Success to me is serving my clients in the best way possible and knowing each and every day that I've put forth the most amount of effort that I can. I never want to p

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What happens when a tech executive discovers she can beat her financial advisor's returns by 5%? Divya Smith, founder of Ascending Avenue, shares her journey from 20+ years in Fortune 500 leadership to managing $300M+ in multifamily assets while helping others achieve financial freedom without sacrificing family time.

[00:00 - 07:00] From Corporate Technology to Real Estate Investing

• 20+ years in technology leadership and executive roles at Fortune 500 companies
• The unsettling realization that financial advisors didn't know as much as expected
• Testing her investment skills: 19% returns vs advisor's 14% (minus fees)
• How a LinkedIn connection who quit corporate for real estate sparked the transition

[07:01 - 14:00] Learning from Single Family Rental Mistakes

• Managing one property with 5 tenants over 15 years - including police visits and drug issues
• Being $600 below market rent due to discomfort raising prices on struggling families

[14:01 - 20:00] Building a Different Kind of Real Estate Business

• Currently managing 3 investments per year (down from 4 to avoid burnout)
• The importance of in-house property management and construction teams
• Creating community through quarterly events: pizza parties, Halloween celebrations, Easter hunts
• Why Class B multifamily became the sweet spot for investments

[20:01 - 29:00] Final Four & The Real Goal of Financial Freedom

• Worst job: Asking for $9M in leftover funds for community initiatives - and being denied
• Paradigm-shifting book: "Atomic Habits" by James Clear (re-read annually)
• Skill to learn: Guitar (gifted 2 years ago, still waiting to be played)
• Success definition: Helping others define their own success and touching 10,000 lives through career coaching

Connect with Divya:

Website: https://www.ascendingavenue.com

LinkedIn: https://www.linkedin.com/in/divyasmith/

Instagram: https://www.instagram.com/investwithdivya

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Key Quote:

"The goal is not to quit your job. The goal is to do what you love to do." - Divya Smith

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What happens when a Hollywood producer trades movie sets for multifamily properties? Michael Jacobs, founder of Mar Vista Entertainment (sold to Fox Studios), shares his transition from 25 years in entertainment to building a vertically integrated real estate empire in Pittsburgh.

[00:01 - 08:05] From Hollywood Producer to Real Estate Investor

• Built Mar Vista Entertainment from a 2003 business plan to Fox Studios acquisition
• Specialized in $5M-and-under movie production for Netflix, Disney Channel, Lifetime
• The decision to transition away from Hollywood's demanding travel schedule
• Started with three duplexes to test the rental market in Pittsburgh's Squirrel Hill

[08:06 - 15:40] Building a Vertically Integrated Real Estate Business

• How frustration with general contractors led to building an in-house construction team
• The challenge of 100-year-old infrastructure: cast iron pipes, knob-and-tube wiring
• Expanding from rental properties to becoming one of Pittsburgh's premier design-build firms
• Why complete gut renovations became the standard approach for old housing stock

[15:41 - 22:10] The "Singles and Doubles" Business Philosophy

• Why avoiding the pressure for home runs and grand slams builds sustainable businesses
• The danger of social media hype and "get rich quick" mentalities
• How to test, measure, and scale gradually while watching the numbers
• Balancing tenant satisfaction with property upgrades to reduce turnover

[22:11 - 28:40] Final Four & Building for the Future

• Worst job: Cleaning motel rooms for $6/hour time-and-a-half on Sundays
• Paradigm-shifting book: "Buy Back Your Time" by Dan Martell
• Skill to learn: Guitar (joining the ranks of aspiring musical entrepreneurs)
• Success definition: Providing for family and keeping nine children and two grandchildren happy

Connect with Michael:

Website: https://marvistadb.com
LinkedIn: Michael Jacobs

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Tweetable Quotes:

"The numbers drive everything at the end of the day. " - Michael Jacobs

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What does it take to gain the trust of investors and build a business that thrives in such a relationship-driven industry?

In this episode of Weiss Advice, Yonah speaks with Julia Anderson, founder of Capital Catalyst and fractional CMO, who shares her journey from managing restaurants to becoming a marketing leader in real estate syndication. Julia explains how her early hands-on business experience prepared her to help capital raisers build credibility, manage marketing systems, and create authentic connections with investors. She also discusses the pitfalls she sees when working with new clients, the importance of CRM systems, and why personal branding often outweighs company branding when raising capital.

[00:01 - 07:30] From Restaurants to Real EstateKey Takeaways:

• How Julia transitioned from restaurant operations to real estate marketing.
• Why her early leadership roles shaped her confidence and skillset.
• The importance of seeing opportunity in unexpected industries.

[07:31 - 14:00] Thrown Into the World of Multifamily

• What Julia learned at her first Best Ever Conference.
• How she began to understand multifamily syndication from the ground up.
• The significance of asking questions and staying curious in new industries.

[14:01 - 21:30] Marketing Pitfalls and CRM Challenges

• Why CRMs often fail without proper customization.
• How messaging clarity impacts investor trust and action.
• The need to tailor marketing systems to both the business and its audience.

[21:31 - 28:30] The Power of Personal Branding

• Why investors follow people, not just brands.
• How authenticity and storytelling build trust.
• What the significance of consistency is in social media and content creation.

[28:31 - 34:47] Always Be Raising: Building Long-Term Systems

• Why raising capital isn’t an overnight process.
• How the right systems create sustainable investor relationships.
• The importance of preparation before a deal is on the table.

Connect with Julia:

LinkedIn: https://www.linkedin.com/in/andersonjulia/

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Tweetable Quotes:

“People follow a person. They don't follow a brand… So they need to know who you are as a person.” - Julia Anderson

“The systems and the processes you build in a solid marketing foundation are what keep you from ever needing to scramble to raise c

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What does it take to go from cash-advancing a credit card to building a vertically integrated, multi-state real estate empire? In this episode, Chris Hanson, the CEO and Founder of Hanson Capital Group, opens up about his real estate journey—from stumbling into trustee sales during the Great Recession to becoming a powerhouse in industrial real estate. He unpacks the lessons learned from losing deals, shutting down businesses, and redefining success beyond financial gains. He also reveals why small bay industrial is his top pick for 2025 and how he structures deals with a long-term vision and value creation in mind.

[00:01 - 07:00] A Credit Card and a Craigslist Hustle

• Why starting small can lead to scalable success.
• The importance of offering value in a crowded market
• How service-based business models can sustain early investing mistakes.

[07:20 - 14:24] When Apartments Clicked

• The significance of income-producing assets versus speculative flips.
• What can be learned from buying below market in a recession.
• The importance of persistence through uncertainty and fear.

[14:25 - 21:41] Discovering Industrial: The Quiet Goldmine

• How triple net leases create stable, low-maintenance income streams.
• Why a 7-cap with a 4% cost of debt made more sense than chasing overheated multifamily deals.
• The need to adapt strategy based on macroeconomic shifts, not legacy bias.

[21:42 - 28:19] Small Bay, Big Opportunity

• Why small bay industrial properties are in short supply and high demand.
• The significance of assembling smaller assets into institutional-grade portfolios.
• How last-mile logistics and population growth fuel tenant demand.

[28:20 - 37:49] Negotiating with Purpose & Redefining Success

• How Chris applies high-level negotiation strategies to real estate deals.
• The importance of shifting from player to coach in leadership.
• Why success is now defined by impact, not income.

Connect with Chris:

Website: https://x.com/HansonCapital

Facebook: https://www.facebook.com/carl.san12

LinkedIn: https://www.linkedin.com/in/chrishansonre/

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Tweetable Quotes:

"Success comes from... the ability to help others improve their situation." - Chris Hanson

"If somebody else just lost $600K, I could lose the $70K... I hope I can figure this out." - Chris Hanson

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Can one focused year of lead generation change your entire real estate career? In this episode, Carl SanFilippo, real estate broker, investor, and founder of a top-ranked RE/MAX franchise in New Jersey, shares how he went from a “dream job” he hated to building multiple businesses by mastering lead generation, distressed property niches, and scaling through smart investing. He dives into the transition from agent to investor, the power of REOs and short sales, and why patience and consistency matter more than flashy marketing. Carl also explains how he helps his agents build their long-term wealth through real estate investing.

[00:01 - 07:35] The Sliding Door Moment

• Why Carl left his stable job to pursue real estate with zero clients or cash
• How he used a 0% credit card to survive his first year
• The importance of treating real estate like a full-time job from day one

[07:36 - 14:58] Building a Niche in Distressed Properties

• How Carl built his business by targeting distressed property leads
• The significance of learning lead generation techniques that scale
• Why having a clear niche helps agents stand out in a crowded market

[14:59 - 21:14] From Realtor to Investor

• What mindset shift helped Carl transition from flipping to holding
• Why buying even one property can become a wealth-building strategy
• The importance of scale in reducing investment risk

[21:15 - 28:00] Coaching Agents to Think Like Investors

• Why Carl pushes agents to invest in real estate
• How being a real estate professional creates tax advantages
• What agents need to understand about marketing and data targeting

[28:01 - 35:38] Data-Driven Growth & Expanding Into Commercial

• How Carl uses data to identify seller avatars and off-market deals
• What he looks for in a commercial property investment
• The importance of reputation and networking in deal flow

Connect with Carl:

Facebook: https://www.facebook.com/carl.san12

LinkedIn: https://www.instagram.com/carlsanfilippo/reels/

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WHERE CAN I LEARN MORE?

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None of this could be possible without the awesome team at Buzzsprout. They make it easy to get your show listed on every major podcast platform.

Tweetable Quotes:

“At the end of the day, we are in the lead generation business... You could be the best realtor in the world, but if you have nobody to provide that to, it's worth nothing.”

- Carl SanFilippo

“There are opportunities for you as an agent... we live and breathe real estate every day, but when you're able to make that lea

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