Rethink money. Redefine success. Live on your terms.
Hosted by John "JMac" McDonough, this is where bold ideas meet real-world action.
Each episode pulls back the curtain on the raw stories, pivotal moments, and game-changing strategies of entrepreneurs, visionaries, and high achievers who live life on their terms.
It’s not just about building wealth—it’s about creating FREEDOM, PURPOSE, and a LEGACY.
From mindset shifts to tactical moves, you’ll get the tools, inspiration, and motivation to leave ordinary behind and start living uncommonly.
Oleg Bortman built significant wealth through entrepreneurship and real estate—but one of his biggest lessons is that being wealthy on paper doesn’t necessarily mean having access to cash when you need it.In this episode of the Uncommon Wealth Podcast, Oleg shares his journey from immigrating to the United States as a child, entering pharmaceutical sales, discovering real-estate investing through Rich Dad Poor Dad, experiencing the 2007–08 property downturn, and eventually leaving a six-figure career to build a business in Phoenix real estate.Today, Oleg is co-founder of The Brokery, but this conversation goes far beyond selling homes.Oleg explains why scaling a company can initially pay less than doing the work yourself, how higher income changed the kind of tax and financial advice he needed, why he creates access to liquidity before he needs it, and why entrepreneurs should prepare financially for the possibility that business conditions will eventually change.IN THIS EPISODE- Oleg’s immigration story- Starting his career in pharmaceutical sales- How Rich Dad Poor Dad changed his relationship with money- Buying his first investment property- Building a Las Vegas real-estate portfolio- Watching property values decline during the financial crisis- Leaving a six-figure career for Phoenix real estate- Building The Brokery with Tucker Blalock- Working in the business vs. working on the business- Why scaling through other agents initially pays less than personal production- What seven-figure income changed about Oleg’s financial thinking- Tax compliance vs. forward-looking planning- Why your advisor network changes as your financial life becomes more complex- LLCs, insurance, trusts, and specialized advisors- Diversifying beyond real estate- Oleg’s dream of eventually owning a soccer club- Why successful business owners can still have almost no liquidity- Establishing access to credit before you need it- Oleg’s current view of permanent life insurance- The future vision for The Brokery- Why Oleg believes founders need 12–18 months of reserves- Raising performance standards as a company grows- Why the founder cannot be CEO, CFO, COO, bookkeeper, and marketer forever- Oleg’s best investment- His morning walking routine- What people misunderstand about successCONNECT WITH OLEG BORTMAN🌐 Website: https://thebrokery.com💼 LinkedIn: https://www.linkedin.com/in/oleg-bortman/📺 YouTube: @olegbortman📸 Instagram: @olegbortman1#jmacwealth #jmacadvice #jmacstrategy #johnmcdonough #uncommonwealthpodcast #UncommonWealth #wealthbuilding #entrepreneurship #financialfreedom #realestate #realestateinvesting #luxuryrealestate #realestateagent #businessgrowth #generationalwealth #taxplanning #wealthmanagement #investing #businessstrategy #leadership
10 Oct 2026
The Poker Mindset Behind a $100M+ Business
What can a professional poker player teach entrepreneurs about building and protecting a company?For Jared Solomon, co-founder and CEO of Five Iron Golf, the answer is risk.Before Five Iron, Jared studied philosophy, earned a law degree, played professional poker and worked as an equity-options trader. Those experiences shaped how he thinks about probability, downside protection and making decisions when the outcome is uncertain.Five Iron Golf started in 2017 with four simulators in New York City. Today, Jared describes a business generating more than $100 million in revenue, with locations expanding internationally.In this episode of Uncommon Wealth, John McDonough and Jared go beyond the growth story.They discuss why Jared prefers reducing catastrophic downside over maximizing every dollar of upside, why he and his wife have taken money off the table during funding rounds, how Five Iron diversifies its revenue streams, and why successful founders can become so focused on their companies that tax, estate and succession planning fall behind.IN THIS EPISODE:- What professional poker taught Jared about risk- Why good decisions can still produce bad outcomes- Why entrepreneurs often overthink major decisions- How Jared evaluates downside when opening new locations- Why he has accepted dilution to reduce leverage- Why Five Iron takes operational details so seriously- Taking money off the table during funding rounds- Building personal financial security outside the company- Diversifying Five Iron's customers and revenue- Turning the home-simulator trend into another business- Jared's candid realization about estate and succession planning- How he and his wife think about their children's future- Giving children money vs. teaching them to steward wealth- Why your number two should be capable of eventually doing your job- Jared's definition of Uncommon WealthThe central lesson: taking intelligent risk doesn't mean risking everything.Connect With Jared Solomon: 🌐 Website: https://fiveirongolf.com/💼 LinkedIn: Jared Solomon | LinkedIn📸 Instagram: https://www.instagram.com/jaredbsolomon#jmacwealth #jmacadvice #jmacstrategy #johnmcdonough #uncommonwealthpodcast #UncommonWealth #wealthbuilding #entrepreneurship #financialfreedom #businessstrategy #riskmanagement #leadership #businessleadership #scalingbusiness #entrepreneurmindset #businessowners #generationalwealth #wealthmanagement #entrepreneurship #riskmanagement #businessgrowth #scalingbusiness #privateequity
9 Oct 2026
Can Your Wealth Survive Without You? | Building Lasting Wealth
Building wealth is one challenge. Keeping it, protecting it, and building a life around it is another.In this episode of the Uncommon Wealth Podcast, John McDonough sits down with John Casmon to explore what happens after an entrepreneur or investor starts achieving financial success.John Casmon shares lessons from his journey from corporate America to entrepreneurship and real estate investing, including how his definition of success evolved from simply making more money to gaining control over his time and lifestyle.They discuss why investors need to periodically rethink their portfolios, why a business that depends entirely on its owner creates risk, how systems and SOPs can make a company stronger, and why personal financial organization matters just as much as business organization.The conversation also dives deep into proactive tax planning—including the important difference between a tax preparer and a tax strategist—and why successful investors should understand the purpose of every investment in their portfolio.In this episode:- Why financial goals change as wealth grows• What “success” actually means beyond a dollar amount• Why too much equity in one asset can create opportunity cost• Building a business that can operate without you• Why entrepreneurs need systems and repeatable processes• Preparing your family for wealth and responsibility• Teaching children how money and business actually work• Tax preparer vs. tax strategist• Why proactive tax planning matters• Building a team of advisors around your wealthThe bigger question isn’t simply:“How do I make more money?”It’s:“How do I build wealth that gives me more control over my life?”Subscribe to the Uncommon Wealth Podcast for conversations about business, investing, wealth strategy, entrepreneurship, and building a life with greater freedom and control.Connect with John Casmon @JohnCasmonMultifamily (https://studio.youtube.com/channel/UCXOupf9--oWUmmg3RiIzXZQ) 🌐 Website: casmoncapital.com💼 LinkedIn: https://www.linkedin.com/in/multifamily-apartments-john-casmon/📺 YouTube: https://www.youtube.com/@JohnCasmonMultifamily📘 Facebook: https://www.facebook.com/p/John-Casmon-100028409780377📸 Instagram: https://www.instagram.com/jcasmon#UncommonWealth #wealthbuilding #entrepreneurship #financialfreedom #realestateinvesting #investing #realestate #taxplanning #wealthmanagement #personalfinance #passiveincome #businessowners #estateplanning #AssetProtection #generationalwealth #johnmcdonough #jmacadvice #jmac
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