When it comes to achieving true financial freedom, there’s a vast difference between chasing hype and building a repeatable, trustworthy system. On a recent episode of “Raising Private Money,” Jay Conner sits down with Lane Kawaoka—an engineer turned real estate powerhouse—who has raised over $200 million in private capital and owns more than 10,000 units. Lane’s journey isn’t just impressive in numbers; it’s a how-to guide for investors ready to scale thoughtfully, avoid rookie pitfalls, and reach financial independence.

From Corporate Engineer to Real Estate Leader

Lane Kawaoka’s introduction to real estate investing wasn’t marked by overnight success. Instead, it grew from years of disciplined learning, starting with investing in single-family homes as early as 2009. Eventually, he transitioned from his high-paying engineering job to focus full-time on real estate, not because it was easy, but because he saw the power of repeatable systems. As Lane began raising private money, he relied on building strong relationships, first with friends and family, then expanding outward, always putting trust and alignment at the forefront.

Breaking the Million-Dollar Ceiling

Many new investors gather their first million through hustle—buying rentals, flipping properties, and leveraging local relationships for their first private loans. But what gets someone to one million often won’t get them to ten million and beyond. Lane’s “Wealth Elevator” framework breaks down the journey into distinct floors.

The first floor involves building a solid base through savings and owning rentals. The second floor ushers in accredited investor status, where access to more lucrative, risk-managed deals becomes possible. The third floor is where investors with $3–4 million net worth begin to focus on preservation, shifting from aggressive growth to capital protection and diversification into vehicles like T-bills, life insurance, and private money lending.

Those in this second-floor space—the million to multi-million range—still need to take calculated risks. Simplistic “set it and forget it” strategies no longer suffice. Instead, these investors must evaluate deals with a discerning eye, balancing risk and reward as they work towards their ultimate financial freedom.

Systematic Decision-Making and Honest Conversations

Unlike many in the industry who pitch investments by inflating numbers and projecting excessive optimism, Lane prefers a system-driven, data-first approach. When considering a deal, he and his team start by examining raw financials—rent rolls, profit and loss statements, and cap rates—without manipulation. They look for conservative assumptions, such as cautious reversion cap rates and realistic rent escalators, instead of painting a rosy picture.

Importantly, Lane prioritizes transparency. He discusses not just why an investment could succeed, but openly points out possible risk factors. This willingness to “test the deal before looking at the answers” builds authenticity and long-term trust with investors. He draws a clear line: if a prospective investor requires constant reassurance or isn’t comfortable with the possibility of loss, private placements in real estate may not be the right fit.

Alignment Over Aggressive Pitching

The essence of Lane’s capital raising philosophy is simple: alignment. He treats raising money as a process of mutual fit, not of one-way persuasion. Potential investors are encouraged to think carefully about whether their personal goals, timelines, and risk tolerance align with the realities of multifamily deals, private lending, or syndications. Lane’s team offers open communication and a clear-eyed view of both the protections and limitations of their investments. Rather than pushing for a sale, they aim for every investor to go in “eyes wide open,” knowing both the upside and the possible storms ahead.

In today's fast-paced real estate market, the key to scaling your investment business often comes down to leveraging the right tools and adopting a mindset for growth. On the episode “Taking Your Business To The Next Level Through Automation,” listeners are treated to a wealth of practical strategies, courtesy of Daniel Martinez, a seasoned real estate entrepreneur who’s participated in transactions exceeding $19 million.

Daniel Martinez’s journey is a masterclass in using curiosity and grit to forge ahead in a challenging industry. Far from inheriting a ready-made portfolio or a family network of connections, Daniel Martinez built his business from the ground up, focusing on creative finance, private money, and tackling the messy deals many investors avoid. His ability to solve title issues, handle liens, and deal with heirs and complex transactions has set him apart. But what really stands out is his commitment to systematizing and automating his business processes, enabling him not only to close deals efficiently but also to scale sustainably.

Central to Daniel’s approach is the use of technology, particularly automation. By implementing customized CRM platforms like Nytfire and integrating AI tools such as Originate AI, he has streamlined underwriting, lead management, and deal analysis. Automation in these areas liberates investors from being tied up in repetitive administrative tasks. Instead, automation pivots their energy toward building relationships, finding deals, and raising capital—the activities that truly move the needle.

One clear takeaway for entrepreneurs is the importance of talking about what you do. Daniel Martinez highlights that if you’re not vocal about your investing activities, opportunities will pass you by. Private lenders and partners can only discover and trust you if they’re aware of your work and your approach. Consistent networking and sharing your business journey publicly—whether through social media, podcasting, or direct conversation—creates an ecosystem where trust and accessibility flourish.

The episode also sheds light on the reality that there’s often more money available than deals. Many would-be investors have capital but lack the time or inclination to pursue opportunities directly. A strategic investor, therefore, focuses on building relationships with these capital sources in tandem with sourcing deals. For Daniel Martinez, raising private money was never about having a deal first; it was about having open-ended conversations that built trust over time. Automation supports this by making it easier to provide information, track communications, and stay organized as your pool of potential partners grows.

Mindset emerges as another crucial element. The transition from believing you can’t raise private money to understanding you are a trustworthy steward of capital isn’t overnight. It’s a blend of honesty about your experience level, a willingness to learn from others—especially lenders who might have significant expertise—and the drive to keep improving. Early-stage investors are encouraged to start with simple transactions and work their way up, gradually building a track record they can leverage.

When it comes to educating private lenders about complex or creative deals, clarity is non-negotiable. Daniel Martinez advises simplifying deal presentations so partners can easily digest the risks and rewards. Automation tools help by generating clear, consistent summaries and analyses for each deal, supporting better communication and confidence all around.

Perhaps most inspiring is Daniel Martinez’s use of podcasting and content creation not merely as marketing but as credibility builders. Being visible, consistently present, and Googleable helps attract partners who are already halfway sold by the time they reach out.

For real estate investors seeking to elevate their business, embracing automation isn’t just about saving time—it’s abou

In the ever-evolving world of home services and small businesses, generating a steady stream of high-quality leads is key to scaling, maximizing revenue, and ultimately creating a sellable business asset. This challenge, however, trips up countless business owners, leaving them at the mercy of inconsistent work schedules and unpredictable growth.

The insights shared by Phil Risher, founder of Phlash Consulting, on the "Raising Private Money" podcast reveal the exact systems that have helped companies consistently fill their pipelines, triple profits, and achieve premium buyout multiples.

Phil Risher’s journey from paying off $30,000 in student loans and saving $60,000 by age 25, to leading a local duct cleaning company through explosive growth, and finally building a seven-figure digital marketing agency, provides invaluable lessons for service-based businesses.

His expertise has been acknowledged by outlets like Forbes, CNBC, and Business Insider, making his findings particularly noteworthy for anyone looking to scale their company.

At the heart of Phil’s approach is understanding that success is rarely tied to having the best product or the most talented team. It hinges on establishing robust systems for visibility, conversion, and follow-up.

Phil emphasizes that the most important growth levers for any home service company are: bringing in new customers, converting leads into paying clients, and retargeting past clients to maximize lifetime value. These three pillars are foundational for creating a business that is not only profitable but attractive to potential buyers and investors.

To start, getting new customers in the door is all about visibility. Most home service businesses rely heavily on Google searches, but being present in multiple search areas and advertising platforms is crucial. Many companies make the mistake of blindly spending money on digital ads without understanding their true return on investment.

Phil points out that without tracking the effectiveness of ad spend, businesses can throw away thousands each month, praying for leads rather than strategically cultivating them.

The second growth lever is conversion. Generating leads is just the beginning; converting those leads into actual sales requires a thoughtful and systematic approach. Phil’s team establishes lead nurture sequences that combine instant text and email follow-ups, turning cold website inquiries into engaged, warm prospects.

Automations like requesting a photo of the project or issue can immediately move the conversation forward and prompt action from the prospect, increasing booking rates dramatically. Data from Phil’s work suggests that setting up automated nurture sequences can boost booking rates from an industry average of 42% up to 62%, all without increasing spend on ads.

Retargeting is the third essential pillar and often the most overlooked. Businesses already possess a goldmine in their existing client database. These customers know, like, and trust the brand, making them ideal candidates for repeat business. Phil’s two-step email playbook involves monthly email newsletters tied to a seasonal content calendar, followed up by targeted offers to those who engage.

Coupled with occasional text message marketing, these tactics keep a business front-of-mind and drive extra revenue with minimal extra cost. In one case, a client implementing these strategies saw an additional $257,000 in revenue over a year, solely from email retargeting.

Beyond lead generation and conversion, Phil Risher highlights the importance of tracking key metrics: booking rate, close rate, average ticket size, and customer acquisition cost. For businesses aiming to double their sales, focusing on month-over-month improvements in these four areas provides clarity and direction. Phil recommends picking one metric each month to optimize, ensuring consistent