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Month: March 2026
Interview with Jayson Gaignard Why Relationships Are the Greatest Investment for Entrepreneurs with MastermindTalks Founder, Jayson Gaignard The best asset that most entrepreneurs overlook is relationships. It’s an investment that compounds over time, and when you surround yourself with curious, like-minded people who have your back, they help you take bigger swings, and shape…
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One of my core missions with The Lifestyle Investor is simple: to democratize what single-family offices do. After all, the right playbook won’t make you a billionaire, but it will make you an investor like one. That’s why I enjoy interacting with investors and entrepreneurs who have been on both sides of the table: entrepreneurs…
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Two weeks ago, I introduced the three forces reshaping the investment world that I see playing out right now, as we speak: The shift from public markets to private markets. The shift from investment advisor to family office paradigm. The shift from net worth to cash flow. Last week, we talked about the…
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Interview with Scott Lingle From a 9-Figure Exit to Inspiring the Next Generation of Entrepreneurs with Scott Lingle Building a successful career in the corporate world and reaching the pinnacle isn’t easy. Walking away from that success, with four kids and looming college bills, to bet on yourself is even harder. Most people never…
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There’s a moment very few people prepare you for: the day the hustle finally works. After a decade of relentless effort, the sacrifice pays off. Sleep, weekends, vacations — all traded for a future exit. Then it happens. The wire hits your account. The scoreboard flashes. You’ve won. You never have to work for money…
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In last week’s issue of the Lifestyle Investor Lens, I talked about the three forces that are colliding right now and reshaping the investment world. A quick recap: Shift #1: From public markets to private markets Shift #2: From investment advisor to family office paradigm Shift #3: From net worth focus to cash flow…
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How to Avoid Leaving Millions on the Table When Selling Your Business with Stephen Scoggins – EP 281
Interview with Stephen Scoggins The Playbook To Prepare for a Life-Changing Exit with Stephen Scoggins It’s crazy when you think about it, but less than 1% of entrepreneurs ever sell their companies. Even fewer do it intentionally, strategically, and on their terms. If you’re building a business without preparing for a future exit, you…
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When I wrote The Lifestyle Investor, I included a section about a private client I called “JJ.” Although I kept it cryptic at the time, the secret is finally out. JJ stands for Jay Jacobs, an OG Lifestyle Investor Mastermind member. He was also my first private coaching client. We have also been working together…
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I’ve been sitting on this idea for a while now. Every week inside the Lifestyle Investor Mastermind, I’m surrounded by some of the smartest investors I know. We’re having conversations that challenge conventional thinking, dissecting deals and debating strategies that most people will never hear about. And until now, those conversations have stayed inside the…
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Interview with Andrew Lassise How Niching Down Led to a 10x EBITDA Exit with Andrew Lassise One of the biggest reasons many entrepreneurs struggle to scale their businesses is that they focus on attracting more clients by casting a wide net and pouring money into marketing that doesn’t generate and convert enough leads. But…
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