Episode Details

Private investing is having a moment - but should you actually be investing in startups?

Serial entrepreneur and investor Jaclyn Johnson joins Mary Holland to breakdown what you need to know before putting your money into a private company: who can invest, how much risk you should actually take, why your money could be tied up for years, and what really has to happen before an investment pays off.

And Jaclyn knows risk from both sides of the table. She built Create & Cultivate from scratch, sold the company for $22 million, and later made the unexpected decision to buy it back. She gets candid about:

- what a $22 million exit actually means for a founder

- what she did when the money hit her account

- how she thinks about knowing when “enough” is enough

-  why emotion isn't always the enemy when making big business decisions.

Plus, Jaclyn shares what she’s learned investing in companies like Away, Chillhouse, and Crown Affair—and what she looks for before writing a check today.

Whether you're curious about angel investing, building a company of your own, or just trying to understand how wealthy people think about risk, this episode will help you ask a better question: What kind of risk actually makes sense for me?

Keep Up With Mary Holland

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LinkedIn: ⁠@MaryHolland⁠

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DISCLOSURE: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. All investing involves risk, including loss of principal. Guests and the host may own securities discussed on this show, and nothing said here is a recommendation to buy or sell any security. Always do your own research and consult a licensed financial advisor before making financial decisions. This podcast is not produced, reviewed, or endorsed by Mary & Pip Investments LLC, a registered investment advisor, nor its affiliates. Nothing said here reflects the views, advice, or services of that firm.

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