The Rich Somers Report

Rich Somers sits down with Jack Delosa, Australian entrepreneur and founder of The Entourage, to break down what it really takes to scale a business from six figures to eight figures and beyond. Jack shares why most entrepreneurs struggle to reach $10 million in revenue, how to identify the biggest bottlenecks holding a business back, and why working harder isn't always the answer. They dive into building leadership teams, hiring for your weaknesses, mastering sales and marketing, and focusing on the few activities that actually drive growth.

Jack also opens up about losing 80% of his company's revenue practically overnight, facing losses of $500,000 per month, and spending four years fighting to rebuild the business. Rich and Jack discuss how to get your time back as a founder, eliminate distractions, structure your calendar for deep work, and avoid chasing opportunities that pull you away from your core business. Jack shares the lessons he's learned from building multimillion-dollar companies and why overcoming difficult challenges is often what creates the biggest breakthroughs in business and life.

If the viewers & listeners send Jack a Direct Message on Instagram, “Rich”, he will send you his full system for getting their time back, their profit up, and creating a business & life by design.

https://www.instagram.com/jackdelosa 

Connect with Rich on Instagram: @rich_somers

Rich Somers sits down with Ana Klein, also known as The Tax Boss, to break down the tax strategies wealthy investors and business owners use to reduce their tax bills. From the Augusta Rule and short-term rental loophole to cost segregation, bonus depreciation, and Section 179 vehicle deductions, Ana explains how the tax code can work in your favor.

They also discuss how high-income W-2 earners can leverage real estate, why business owners put their children on payroll, the power of self-directed IRAs, and how holding companies can fit into an asset protection strategy. Whether you're making $300,000 a year, scaling a business, or building a real estate portfolio, this conversation explores tax planning opportunities worth discussing with a qualified professional.

Disclaimer: This episode is educational and does not constitute tax, legal, or financial advice. Tax benefits depend on individual circumstances and eligibility requirements.

Ana shares that if you're a business owner or real estate investor making over $400K, and your CPA's only advice is "pay your estimated taxes," that's not a strategy. Last year they helped their clients save over $4M in taxes. Go to the-taxboss.com and fill out their short questionnaire to see if you qualify for a strategy call.

Connect with Rich on Instagram: @rich_somers

Why is Chick-fil-A one of the most successful restaurant businesses in America, even though it isn't open on Sundays? 

In this episode, Rich Somers sits down with hospitality expert Preston Lee to uncover the business strategies behind Chick-fil-A, Ritz-Carlton, and other world-class hospitality brands. Preston breaks down the difference between customer service and true hospitality, why most businesses struggle to retain customers, and how creating an exceptional guest experience can become your biggest competitive advantage.

They also discuss why A-players don't want to work with C-players, the leadership mistakes that destroy company culture, and how to build systems that consistently deliver five-star experiences. Preston shares why most managers are never properly trained to lead, how to create a culture of accountability through feedback, and what business owners can learn from the world's most successful restaurants and hotels. Whether you're running a restaurant, hotel, service business, or growing a team, this episode is packed with practical insights on leadership, customer loyalty, employee performance, and building a business people genuinely love.

Connect with Rich on Instagram: @rich_somers

Could residential assisted living be one of the biggest real estate investing opportunities of 2026? In this episode, Rich Somers sits down with Isabelle Guarino, residential assisted living investor and educator, to break down the massive opportunity being created by America's aging population and the growing demand for senior housing. Isabelle explains how investors can convert residential homes into assisted living facilities, why certain operators are generating $20,000 to $40,000 per month in cash flow, and which real estate markets offer the most attractive opportunities.

They also dive into the actual numbers behind operating assisted living homes, including financing with SBA loans, renovations, caregiver staffing, occupancy, marketing, and maximizing profitability. Isabelle reveals why she prefers purchasing existing care homes, how to identify the right demographics before investing, and what it takes to build a portfolio that institutional buyers may want to acquire. Whether you're an experienced real estate investor or exploring your first assisted living investment, this conversation provides a practical look at the opportunities, challenges, and business strategies behind residential senior care.

Ready to take the next step? Visit RAL101.com to grab your FREE book, sign up for an upcoming webinar, or book a call with Isabelle or her team! 

Connect with Rich on Instagram: @rich_somers

 In this episode, Rich Somers sits down with Devan Bonebrake, host of *The Golf Fix* on Golf Channel and founder of Studio Golf Club, to break down what it really takes to become a better golfer. Devan shares how to improve your game in just 30 days, fix your slice, hit longer drives, improve your iron shots, and use modern golf technology to get better results from every practice session.

They also dive into why entrepreneurs and professional athletes are obsessed with golf, how the sport has become one of the most powerful networking opportunities in business, and why indoor golf clubs could represent the future of the industry. From Tiger Woods and Steph Curry to building a growing golf business, this episode covers the intersection of golf, entrepreneurship, technology, and personal development.

Connect with Rich on Instagram: @rich_somers

Rachel Woods spent her career working in AI, including as a research data scientist at Facebook, long before ChatGPT brought artificial intelligence into the mainstream. In this episode, she breaks down how business owners should actually be thinking about AI—not as another collection of tools, but as a new way to operate a company. Rachel explains how she turns repeatable work into AI “playbooks,” why operations matter more than technical expertise, and how one command can kick off an entire AI-powered daily workflow.

We also dive into the four components every AI playbook needs, why companies should use AI to improve their product instead of simply cutting payroll, when to hire an AI operator versus an engineer, and how existing businesses can gain an advantage by integrating AI behind the scenes. Rachel even breaks down real examples involving email, proposals, project management, customer service, hotel operations, and influencer marketing to show how businesses can gradually automate more of their everyday work.

If this conversation sparked something, the best first step is to build your first playbook. 

Rachel made a free guide that walks you through turning one recurring task into a playbook that runs with AI. Get it here! 

Connect with Rich on Instagram: @rich_somers

Jacob Lawson invested $500,000 into a restaurant just before COVID, found himself facing nearly $1 million in debt, and was forced to rethink everything about the way he approached business. Today, his business generates roughly $5 million a year. In this episode, Jacob breaks down the decisions that helped him turn things around, why trying to operate multiple businesses nearly broke him, and the lesson that changed his trajectory: keep the main thing the main thing.

We also dive into Jacob’s flooring and real estate businesses, the mistakes he’s made with partnerships, why fast decision-making matters, and how he thinks about risk, accountability and investing in yourself. Jacob shares his daily gratitude practice, his four pillars for an extraordinary life—health, wealth, relationships and purpose—and why knowing your numbers, pushing beyond comfort and taking complete ownership of your results are essential to building a better business and life.

Join The Extraordinary Core — Jacob’s free men's community built around those four pillars. For anyone who wants to know exactly where they stand, take the Extraordinary Man Scorecard first — it scores you across all four pillars and shows you which one is quietly holding you back. 

Connect with Rich on Instagram: @rich_somers

Dylan Crane went from making $6,500 a month as a professional basketball player to building a life insurance business doing as much as $200,000 a month. In this episode, Dylan breaks down how the life insurance business actually works, how agents get paid, the difference between term and whole life insurance, and how he approaches infinite banking and using cash-value life insurance as a financial tool.

We also dive into what it takes to build a six-figure-a-month insurance business, the sales psychology and tonality Dylan teaches his agents, how he recruits and manages a team, the KPIs he tracks, and how commissions, annuities, leads, and appointment setters work behind the scenes. Dylan also shares the work ethic that took him from basketball into entrepreneurship, the lessons he's learned building his team, and why he believes life insurance remains one of the biggest opportunities for ambitious salespeople.

Connect with Rich on Instagram: @rich_somers

Employee healthcare benefits can become one of the largest expenses inside a growing business—but most owners don't fully understand what's driving those costs or what options they have to control them. Caleb Herndon breaks down why healthcare and insurance costs continue to rise, the role of pharmaceutical spending, insurance carriers and an aging population, and how employers can rethink the way they structure their benefit plans.

We also dive into self-funded and level-funded health plans, pharmacy benefit managers, strategies for controlling claims, and how Caleb helped a struggling municipality reduce expenses. Later, Caleb explains how AI is transforming the insurance industry, why he built Quote Map to automate time-consuming insurance analysis, and how technology could give brokers and business owners better information while saving hundreds of hours of administrative work.

Brokers & Agency Owners: See how AI can help you analyze benefits faster and uncover missed opportunities at QuoteMap.ai. Rich Somers listeners get their first month FREE ($200 value) at QuoteMap.ai/RichSomers.

Business Owners: Want to understand where your benefits dollars are going? Reach out to Benefits Blueprint to uncover opportunities and potential savings.

Connect with Rich on Instagram: @rich_somers

How much money do you actually need to own a private jet? Travis Lamance manages 24 private jets and helps clients buy, sell and operate aircraft. In this episode, he breaks down what first-time jet buyers spend, how to choose the right aircraft, what different jets cost to operate, and why private aviation may be more attainable for successful business owners than most people assume.

We cover everything from Citation, Hawker, Gulfstream, HondaJet and Cirrus aircraft to chartering your jet to offset expenses, pilot salaries, maintenance reserves, fuel costs, range, renovations and the hidden expenses buyers often overlook. Travis also explains how some owners can offset a significant portion of their operating costs and what you should understand before buying your first private jet.

Check out jetcowboy.com for exclusive information and special discounts available to listeners!

Connect with Rich on Instagram: @rich_somers