059: Sam Marks on Building a $100M Exit and Learning to Invest Like a Boss
The Lifestyle Investor - Investing, Passive Income, Wealth
From Bad Advisors to Invest Like a Boss
How losing trust in advisors led Sam to start Invest Like a Boss, learn investing publicly, and adopt core lessons: low fees, broad diversification, and avoiding stock-picking.
Today, I’m speaking with Sam Marks. At the age of 24, after some early setbacks (including 4 arrests while in College) Sam moved from the US to the UK and founded the e-cigarette company, SKYCIG. He bootstrapped the company initially out of the back of a rental car, and grew it into Europe’s largest e-cig brand in only 4 years. In 2013, the business was acquired for $100 million!
Sam had all this money, but no idea what to do with it. He gave 40% of his earnings from the sale of the business to a financial advisory team to manage—later realizing they were losing him money, even when the markets were up. He felt manipulated, duped, and frustrated by the entire process.
He decided it was time to take control of his money. Despite having zero investing experience, he started the Invest Like a Boss podcast, so he could interview and learn from the most experienced investors in the world—while also passing that knowledge on to others.
Sam is now an angel investor, serial entrepreneur, and his investment portfolio includes 400 self-storage units in Hong Kong, a microbrewery in Australia, rental properties across Thailand, and several early stage startups. He’s also visited more than 100 countries while living off passive income and pursuing his bucket list.
In our conversation, you’ll learn about Sam’s entrepreneurial journey, what it was like to negotiate and secure a $100 Million acquisition deal, and the passive income investments that allow him to travel the world and live life on his terms.
Here’s just some of what we get into:
- The early setbacks that led to Sam’s entrepreneurial journey
- How Sam’s various side hustles led to building an e-cigarette business out of the back of his car.
- Negotiating a $100 Million acquisition deal—and the problems he faced along the way.
- Why even the most successful exits are often a negative experience for entrepreneurs.
- Why letting an advisory team manage 40% of his earnings lost him money and ended up being a really horrible experience.
- Foundational investing principles you need to understand in order to master your money.
- How Sam diversified his portfolio and built a lifestyle around his investments—including residential property in Thailand and 400+ self-storage units in Hong Kong.
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